Quick Winter Park FL MLS Search

Browse All Winter Park FL 3 Bedroom Properties for Sale

$435,000
3 Beds ⋅ 3 Baths ⋅ O6424623 MLS
Move-in-ready Winter Park gem in top-rated Seminole County schools! This 3BR/2BA home features a private split-bedroom layout. The home features laminated wood flooring in all the bedrooms and beutiful tile in the kitchen and bathrooms. Both bathrooms feature newly updated toilets. The expansive eat-in kitchen is a chef's delight, boasting premium granite countertops, solid light maple cabinets with elegant glass upper doors, and a breakfast bar opening to the large family room. Enjoy total peace of mind with extensive 2023 upgrades, including a BRAND NEW ROOF, new electrical panel, new energy-efficient windows, new French doors, and a new garage door for the 2-car garage.The HVAC system was manufactured in 2019 and installed in 2020 Step outside to a massive, fully fenced backyard featuring a large covered lanai with a brand-new aluminum frame and fresh screens—perfect for outdoor entertaining. Truly a turnkey property optimized for insurance savings and modern comfort. Schedule your tour today!

5225 Albert Drive, Winter Park
$625,000
3 Beds ⋅ 3 Baths ⋅ O6424399 MLS ⋅ 786 BLDG.
Under contract-accepting backup offers. Virtually Staged. Welcome to 786 McIntyre Avenue, Winter Park, FL 32789—a serene retreat perched on a picturesque tree-lined brick street in one of Winter Park's most desirable neighborhoods. Just a short stroll from Rollins College and the renowned shops, restaurants, and charm of Park Avenue, this exceptional single-family townhome offers the perfect blend of comfort, style, and location—SINGLE FAMILY TOWNHOME with NO HOA! A charming driveway leads to the attached two-car garage and private front entrance. Inside, you'll be welcomed by a bright, airy interior featuring soaring ceilings, dramatic high windows, abundant natural light, and a cozy wood-burning fireplace. The spacious living room is surrounded by two private patios, creating a seamless connection between indoor and outdoor living. The updated kitchen boasts modern cabinetry, an open breakfast bar, and a cheerful eat-in dining area with direct access to one of the patios. The formal dining room, currently used as a home office, opens to the second patio, making it the perfect setting for al fresco dining or entertaining. Upstairs, the impressive 23' x 12' primary suite offers a peaceful retreat, complete with a spacious 20' x 8' ensuite bathroom. Two additional guest bedrooms share a convenient Jack-and-Jill bathroom, providing comfort and privacy for family or visitors. Meticulously maintained, this home features numerous recent updates, including a new HVAC system (2025) and beautiful wood shutters throughout. Located in the highly sought-after Audubon K-8 and Winter Park High School districts, this exceptional home combines timeless character, modern updates, and an unbeatable location. WELCOME HOME!

786 Mcintyre Avenue, Winter Park
$569,000
3 Beds ⋅ 3 Baths ⋅ O6423829 MLS
Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, a private full fenced backyard with a pool designed for year-round enjoyment, and a location that's just minutes from everything that makes Winter Park one of Central Florida's most desirable communities. The heart of the home is a bright, open living space where the kitchen, dining, and living areas flow effortlessly together around a wood-burning fireplace. Filled with natural light and designed for connection, it's a space that feels equally suited for lively gatherings, holiday celebrations, or quiet evenings at home. Step outside and discover what truly sets this property apart. A sparkling private pool and a fully fenced quarter-acre yard that creates an outdoor retreat that's increasingly hard to find. Whether you're entertaining friends, watching children or pets play, or simply enjoying a peaceful morning by the pool, this backyard offers the space and privacy to enjoy Florida living the way it was meant to be. Thoughtful updates—including a new roof (2022), HVAC system (2022), fresh interior paint, and updated lighting—provide peace of mind while leaving opportunities for the next owner to make the home uniquely their own. Ideally located just minutes from Park Avenue's dining and boutiques, Lake Killarney, Hillstone, College Park and major commuter routes, this home offers exceptional convenience without sacrificing the character and charm that make Winter Park so special. With a private pool, two-car garage, generous outdoor space, and an open floor plan that truly lives for entertaining, 2803 Riddle Drive offers a rare opportunity to enjoy the Winter Park lifestyle at an exceptional value.

2803 Riddle Drive, Winter Park
$255,000
3 Beds ⋅ 2 Baths ⋅ O6418973 MLS ⋅ 2450 BLDG.
Rare end units like this don't come around often! Welcome to 2450 Grand Teton Circle, tucked away in the well-maintained, established community of Cedarwood Village in Winter Park. This 3-bedroom, 2-bath home is filled with natural light thanks to its end-unit location, and the open layout makes it easy to relax, entertain and enjoy everyday living. The spacious living and dining areas flow together nicely, while the kitchen offers plenty of room to cook, gather, and stay connected with family and friends. Over the past several years, this home has been thoughtfully updated, giving the next owner peace of mind. Major improvements include a new roof, skylights, HVAC system, water heater, kitchen appliances, washer and dryer, updated LED lighting, and fresh interior paint. Both bathrooms have been beautifully remodeled, the home has been replumbed by the HOA, and the primary closet has been enhanced with custom shelving. Additional updates include new flooring in the secondary bedrooms, updated window blinds, and thoughtful finishing touches throughout. The private screened lanai has been transformed into a cozy outdoor retreat with fresh paint, a ceiling fan, new screens and screen door, string lighting, and decorative greenery—making it the perfect place to enjoy your morning coffee or unwind after a long day. Life here is easy. Cedarwood Village is a beautifully maintained, established community featuring a community pool and Clubhouse for your special events, tennis courts, and pickleball courts. The HOA has also recently repainted the exterior of the buildings, helping keep the neighborhood looking fresh and inviting. Best of all, this home is value priced, giving you an incredible opportunity to own in desirable Winter Park without the premium price tag. You're just minutes from Winter Park's shopping and dining, Full Sail University, UCF, major employers, and convenient access to SR-417 and downtown Orlando. If you've been looking for a move-in-ready home in a fantastic location with years of thoughtful updates already completed, this rare end unit is definitely worth a look!

2450 Grand Teton Circle Unit 2450, Winter Park
$575,000
3 Beds ⋅ 2 Baths ⋅ O6420140 MLS
Under contract-accepting backup offers. Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenience. From the moment you arrive, the freshly installed, vibrant green front lawn and attractive landscaping create an inviting first impression. Inside, the cathedral ceiling enhances the spacious feel of the open floor plan, complemented by luxury vinyl flooring and ceramic tile throughout. The well-appointed kitchen features white cabinetry, granite countertops, and a new stainless steel appliance package that adds a modern touch. The home's versatile layout offers plenty of room for everyday living and entertaining, including a separate family room, a bright Florida Room, and a dedicated office or exercise room equipped with an energy-efficient mini-split system and convenient access to the carport. The inside utility room includes a full-size washer and dryer, as well as a second side-by-side refrigerator for added storage and convenience. The spacious primary bedroom provides a comfortable retreat with a private bath featuring maple cabinetry, ample vanity storage, and a roomy walk-in shower. The guest bath offers a tub/shower combination. Step outside to enjoy the spacious, fully fenced backyard—perfect for relaxing, entertaining, gardening, or enjoying the Florida sunshine. Additional features include a storage shed, sprinkler system supplied by a separate well, and a one-car carport with parking for up to three additional vehicles. Major updates include an AC system replaced in 2017, a new roof and electrical panel in 2019, and replumbing completed in 2019. Best of all, you are walking distance to Winter Park High School and just minutes from local dining, shopping, and everyday conveniences. With its spacious floor plan, flexible living areas, attractive updates, generous outdoor space, and prime Winter Park location, this home is a must-see. Schedule your private showing today! Buyer/buyer's agent to verify all schools and room measurements. Appliances convey as is. Brio Management LLC, Seller, is owned by 2 Florida Licensed Real Estate Brokers.

2010 Summerfield Road, Winter Park
$849,000
3 Beds ⋅ 3 Baths ⋅ O6422949 MLS
Under contract-accepting backup offers. Life is simply better when everything is just around the corner. Perfectly positioned in the heart of Winter Park, this beautifully maintained David Weekley home offers the rare opportunity to enjoy one of Central Florida's most desirable lifestyles. Located just four blocks from Park Avenue and one block from Winter Park Village, you'll also enjoy close proximity to Hannibal Square, Central Park, Publix, the Winter Park Farmers' Market, acclaimed restaurants, boutique shopping, museums, cafés, and everyday conveniences. Built in 2017, this thoughtfully designed home blends timeless architecture with modern luxury across a spacious and functional floor plan. The first floor features three generously sized bedrooms and two full bathrooms, including a private primary suite complete with a spa-inspired bath and an expansive walk-in closet. Upstairs, the home's open-concept living spaces are designed for both everyday comfort and effortless entertaining. Natural light fills the expansive living and dining areas, while the chef's kitchen serves as the centerpiece of the home. Featuring premium Jenn-Air stainless steel appliances, a natural gas cooktop, generous cabinetry, beautiful countertops, and a large center island, it's a space equally suited for hosting friends or preparing a quiet dinner at home. Sliding glass doors extend the living area to an oversized balcony with Trex decking, creating an inviting outdoor retreat for morning coffee, evening cocktails, or dining under the stars. Built with quality and efficiency in mind, the home includes double-pane windows, great insulation, and a gas tankless water heater. The homeowners association further enhances the low-maintenance lifestyle by providing lawn and shrub care, irrigation water, and maintenance of the community perimeter wall, allowing you to spend more time enjoying your home and less time maintaining it. More than just a beautiful residence, this home offers an exceptional opportunity to experience the very best of Winter Park. Enjoy dinner on Park Avenue, spend Saturday mornings at the Farmers' Market, explore the boutiques of Hannibal Square, relax in nearby parks, or meet friends for coffee, all just moments from your front door. This is a home where luxury, convenience, and one of Winter Park's most sought-after locations come together beautifully.

439 N Capen Avenue, Winter Park
$179,900
3 Beds ⋅ 2 Baths ⋅ A11902103 MLS
This is a 3 bedroom and 2 bathroom condo. This condo has had everything replaced. Don't miss out on this opportunity. Call listing agent today for more information and to schedule a showing.

7340 Daniel Webster Drive, Winter Park
$415,000
3 Beds ⋅ 2 Baths ⋅ S5153086 MLS
Discover the perfect place to call home! This beautiful 4-bedroom, 2-bath residence offers a spacious layout, a 2-car garage, and the freedom of no HOA. Conveniently located near top-rated schools, shopping, dinning and major highways, it provides the ideal balance of comfort, convenience, and value. Whether you're a first time homebuyer or looking to upgrade, this home is an excellent opportunity you won't want to miss.

3621 Hawthorne Lane, Winter Park
$449,000
3 Beds ⋅ 2 Baths ⋅ O6422197 MLS
Under contract-accepting backup offers. Tucked away on a quiet dead-end street just off Lake Killarney, this solid block 1960's ranch at 2611 Lotafun Avenue offers over 1,800 SF of living space with room to make it your own. Featuring 3 bedrooms and 2 full baths, this home boasts a charming front living room with a wood-burning fireplace, PLUS a spacious family room/sunroom with its own fireplace — perfect for cozy nights or entertaining. The primary bedroom features an en suite bath, while the hall bath charms with original tilework. Step outside to your private pool, set on a generous 0.24-acre lot with a backyard shed for extra storage. Additional highlights include an attached 2-car garage with bonus storage room, interior laundry, and a 2022 roof. All new electrical was just installed in June 2026 by Skolfield Homes, giving buyers peace of mind on one of the big-ticket items. Enjoy the tranquility of this established neighborhood while staying close to major roadways, shopping, and dining. Homes with this much character and potential in Winter Park don't come around often — bring your vision and make this one shine!

2611 Lotafun Avenue, Winter Park
$299,900
3 Beds ⋅ 2 Baths ⋅ TB8525179 MLS
Multiple OFFERS.. highest and best due by 10pm Sunday July 5th, Seller to review offers on Monday. Seller is a corporation and has never occupied the home. Seller does not disclose. It is Buyer and Buyers brokers responsibility to verify all information. Seller chooses Mainstay National Title. 5 day inspection period max. Closing date on or before 45 days from effective date. All appliances stay in home but not warranted by seller. SOLD AS-IS. See offer instructions. AC 10/2020. WH and Roof ages unknown.

7500 Waunatta Court, Winter Park
$499,500
3 Beds ⋅ 2 Baths ⋅ O6421887 MLS
Welcome to this charming home nestled at the end of a quiet cul-de-sac in the desirable Glenmoor community. Featuring 2,067 sq ft of inviting living space, this property offers a perfect blend of comfort and convenience. The open floor plan includes an eat-in kitchen and a spacious family room, ideal for entertaining. Relax in the living room with a cozy wood-burning fireplace. Enjoy outdoor living with a sparkling pool, raised gardens galore, and a fenced yard backing to a tranquil retention pond — no rear neighbors! The home boasts a large driveway, a 2-car garage, and a dedicated RV power hookup. Recent updates include all new vinyl windows to be installed in the enclosed lanai and remodeled bathrooms. This home is situated in a prime location with top-rated schools, close to dining, shopping, and entertainment options, including Winter Park, Baldwin Park, and easy access to highways 408 and I-4. Commuting is a breeze — just 25 minutes to Orlando International Airport, 20 minutes to Downtown Orlando, and within an hour of Cocoa Beach, Disney World, and Universal Studios. Schedule your private tour today and make this fantastic Orlando area home yours!

7509 Glenmoor Lane, Winter Park
$549,000
3 Beds ⋅ 2 Baths ⋅ O6421731 MLS
Welcome home to this beautifully updated 3-bedroom, 2-bath move-in ready home living on a spacious quarter-acre lot in one of Winter Park’s established neighborhoods. From the moment you arrive, you’ll appreciate the home’s inviting curb appeal with refreshed landscaping, and gutters. Inside, the open, light-filled layout features luxury vinyl plank flooring and tile throughout, creating a cohesive and modern feel that’s both beautiful and easy to maintain.The heart of the home is the thoughtfully renovated kitchen, complete with quartz countertops, soft-close cabinetry, Whirlpool and KitchenAid stainless steel appliances - including an induction stove top and double ovens. Major home features have recently been updated giving buyers confidence and peace of mind. The roof was replaced in 2020, the HVAC system in 2023, the water heater in 2019, and windows plus the sliding glass door were replaced in 2025 to improve energy efficiency and comfort. Step outside to your own private backyard retreat. The fully fenced yard offers exceptional space for pets, play, gardening, or even a future pool. An oversized extended paver patio creates the perfect setting for outdoor dining, entertaining friends, or simply relaxing on a Florida evening.

1956 Japonica Road, Winter Park
$695,000
3 Beds ⋅ 2 Baths ⋅ O6420928 MLS
Exceptional opportunity to build new or renovate and expand on this desirable lot in Winter Park. Situated on a charming tree lined street and in a neighborhood that is experiencing a great deal of new development. The existing 1950s residence features parquet wood flooring and open living and dining spaces, which overlooks the backyard and open wooden deck. With generous space to work with, there are great possibilities to create your own custom residence. The property is zoned for long-established schools - Lakemont Elementary, which is just down the street from the property, as well as Maitland Middle and Winter Park High. Plus, ideally located within a short stroll to the Winter Park Y, Phelps Park, and minutes to downtown Park Ave's shopping and dining! Property is being sold AS IS.

1622 Arbor Park Drive, Winter Park
$135,000
3 Beds ⋅ 2 Baths ⋅ O6420863 MLS ⋅ . BLDG.
Welcome to this charming first-floor 3-bedroom, 2-bath condominium located in the beautiful city of Winter Park! Featuring laminate flooring throughout the main living areas, this inviting home offers an open-concept layout with a combined living and dining room that overlooks the kitchen, creating the perfect space for everyday living and entertaining. Each bedroom is equipped with a ceiling fan for added comfort, while the private rear patio provides a peaceful outdoor retreat complete with a bench—ideal for relaxing and enjoying Florida's beautiful weather. Whether you're searching for a primary residence, a seasonal getaway, or an investment opportunity, this condo offers exceptional value. HOA dues include pest control, basic cable, basic internet, exterior maintenance, and additional storage, providing convenience and peace of mind. Residents also enjoy access to community amenities including a swimming pool, playground, and clubhouse, all in a desirable Winter Park location close to shopping, dining, parks, and major roadways. Don't miss the opportunity to make this wonderful property your own!

1695 Lee Road Unit A116, Winter Park
$599,000
3 Beds ⋅ 2 Baths ⋅ O6418164 MLS
Under contract-accepting backup offers. Nested on a spacious, tree lined lot just steps from Lake Killarney, 2361 Roxbury Road offers a rare opportunity to create your dream home in one of Winter Park’s most convenient locations. Ideally situated just off Fairbanks Avenue with quick access to I-4 , this 3 bedroom, 2 bath residence features 1723 square feet of living space, solid plaster walls and mid century character. Built in 1951, the home showcases an original pine paneled ceiling in the living room, adding warmth and architectural charm. Two large, new Anderson windows fill the room with natural light and highlight the pool view. New Anderson exterior doors improve the homes security and efficiency. The expansive Florida room provides flexible space for entertaining or future updates. Major improvements include a resurfaced Gunite pool in pebble finish (2024), exterior paint (2024), new paver driveway (2024), roof (2020) and HVAC system (2019). The garage has been enclosed and currently serves as storage and utility space. Outside you’ll find a fully fenced backyard with plenty of room to enjoy the Florida lifestyle. Located on a large lot with sidewalks and mature trees, this home presents an excellent opportunity for buyers looking to personalize a property in a desirable Winter Park location. The septic system was pumped in 2026, providing peace of mind. Bring vision and make this home your own!

2361 Roxbury Road, Winter Park
$353,000
3 Beds ⋅ 2 Baths ⋅ S5152746 MLS
Under contract-accepting backup offers. Welcome home to this beautifully maintained 3-bedroom, 2-bathroom residence in the desirable Winter Park area! From the moment you arrive, you'll appreciate the long driveway, inviting curb appeal, and numerous recent upgrades that provide both style and peace of mind. Step inside to find updated bathrooms, newer appliances, and a functional layout designed for comfortable everyday living. Major improvements include a new roof and gutters (2023) and a newer water heater, making this home truly move-in ready. One of the standout features is the spacious, fully fenced backyard that backs up to preservation land, offering the privacy and tranquility of having no rear neighbors. Enjoy Florida living year-round from the large screened-in patio, perfect for entertaining, relaxing, or enjoying your morning coffee. Gardening enthusiasts will love the three raised garden beds, ready for planting your favorite flowers, herbs, or vegetables. Conveniently located near major highways, shopping, grocery stores, restaurants, and everyday conveniences, this home also offers easy access to the University of Central Florida (UCF), Valencia College, parks, and a variety of local attractions and family-friendly activities. Whether you're a first-time homebuyer, growing family, or simply looking for a home that combines comfort, privacy, and an unbeatable location, this Winter Park gem is one you won't want to miss. Schedule your private showing today!

2022 Eastbrook Boulevard, Winter Park
$439,900
3 Beds ⋅ 1 Baths ⋅ O6420660 MLS
Seller is highly motivated. Competitively priced for a quick sale. Don't miss your opportunity to own this beautiful home! First time on the market in over 60 years! Filled with decades of cherished family memories, this beloved home is ready for its next chapter. Located in the highly desirable Winter Park 32789 ZIP code, 2041 Jewell Avenue offers an unbeatable location just minutes from Dubsdread Golf Course, College Park, and downtown Winter Park, with quick access to I-4, making commuting throughout Central Florida a breeze. Lovingly maintained and thoughtfully updated over the years, the home features a 2024 roof, central air conditioning, and a large, wheelchair-accessible walk-in shower, providing enhanced comfort and accessibility. The spacious, fully fenced backyard offers plenty of room to relax, entertain, garden, or play. Situated on a quiet dead-end street, you'll enjoy minimal traffic and a peaceful neighborhood setting. The original fourth bedroom has been converted into a generous laundry room, adding convenience and extra storage while offering flexibility for future customization if desired. Whether you're looking to move right in, renovate, or create your dream home in one of Central Florida's most sought-after neighborhoods, this property presents an exceptional opportunity. Now it's your turn to create a lifetime of memories and make this treasured home your own.

2041 Jewell Avenue, Winter Park
$1,025,000
3 Beds ⋅ 3 Baths ⋅ O6420090 MLS ⋅ Virginia Heights BLDG.
Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining areas, beautiful wood floors, crown molding, plantation shutters, a butler bar with custom cabinetry & wine refrigerator. Cooking inspired Kitchen with a lengthy granite island and sitting bar overlooks the Family room. Upgraded stainless appliances, including gas cooktop with griddle, microwave/convection oven, hanging pot rack with lighting, and soft close cabinets with pullouts. French doors to the covered 'English Garden' courtyard with pavers & stainless grill for entertaining. Guest suite or home office with a custom closet and full bath overlooks brick street, Pennsylvania Ave. Large laundry room near the garage with granite countertops, cabinets & utility sink, plus washer & dryer. Upstairs is a spacious Primary bedroom with French doors to a private covered balcony; also, 2 large walk-in closets with closet systems, Jacuzzi tub, huge walk-in shower, dual vanities with granite countertops & more. An additional ensuite bedroom, more wood floors, plus a built-in dehumidifier. Attached 2-car, rear alley access garage, plus an additional side parking pad. Walk to Park Ave. for dining, shopping, WP Tennis Center, outdoor park & Rollins College. Neighborhood Lake Virginia access for paddleboard & kayak launching to the Winter Park Chain of Lakes. Top schools, Audubon K-8 seconds away, and WPHS. NEW TPO membrane roof w/ metal coping March 2026. HOA maintains: landscaping, irrigation, building maintenance & outdoor lighting. Won't last!

1138 S Pennsylvania Avenue, Winter Park
$579,900
3 Beds ⋅ 2 Baths ⋅ O6418278 MLS
Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell for under $600,000. Tucked away in a peaceful, private setting, yet just minutes from Winter Park’s famed Park Ave, Winter Park Village, College Park and Downtown Orlando with numerous shopping and dining options making this property the perfect blend of seclusion and convenience. Built in 1957, this classic Florida ranch features 3 bedrooms and 2 bathrooms within 1,837 SF of living space. Major updates include a new roof in 2024 and HVAC in 2019. Step inside off the covered front porch to find spacious living and dining areas highlighted by charming built-in features and abundant natural light. At the heart of the home, the kitchen offers easy access to a generous walk-in pantry/utility room/laundry area. The adjoining family room opens to a covered back porch overlooking the expansive backyard and tranquil canal. Situated on a .40-acre lot, the property extends beyond the canal, creating a natural wooded buffer that enhances privacy and provides a serene backdrop. Whether you envision a pool, outdoor kitchen, garden, or entertaining space, the backyard offers endless possibilities to create your dream outdoor oasis (subject to municipal review and approvals). Lake Bell is a 36-acre spring-fed ski lake with an average depth of 12 feet, ideal for boating, skiing, kayaking, paddle boarding and enjoying the Florida lifestyle. Fishing enthusiasts will also appreciate the lake’s reputation for largemouth bass and bluegill. Other notable exterior highlights include fenced in backyard, covered front entry, two rear porches and 1-car carport. The home is on septic that has been well maintained and serviced annually. The location also offers quick access to Interstate 4 and close proximity to area hospitals, parks and cultural centers. Don’t miss this exceptional opportunity to own waterfront property in Winter Park/3789 at an incredible value!

1003 Lake Bell Drive, Winter Park
$459,900
3 Beds ⋅ 2 Baths ⋅ O6419225 MLS
Beautifully renovated three-bedroom, two-bath home in desirable Winter Park 32789. Extensively updated throughout, this move-in-ready home offers the perfect blend of modern style, comfort and convenience. Filled with natural light, this home features a stunning renovated kitchen with an open pass-through breakfast bar and seating, ideal for entertaining and everyday living, a large stainless sink beneath a window and plenty of stunning quartz countertop space. Both baths have been tastefully remodeled, and nearly every aspect of the home has been thoughtfully updated to create a fresh, contemporary feel. Major improvements provide added peace of mind, including a new roof in October 2023, an HVAC system in 2023 and a water heater in 2024. Enjoy the convenience of a large covered carport with built-in storage, plus a huge backyard with endless possibilities for gardening, pets, play or future expansion. An additional storage shed, added in 2018, offers even more space for tools, hobbies and outdoor equipment. Ideally located with quick access to Interstate 4 and 17-92 and just minutes from Park Avenue, Winter Park Village, College Park and Downtown Orlando, you'll enjoy some of Central Florida's finest shopping, dining, entertainment and cultural attractions right at your fingertips. Best of all, no HOA. Combining extensive renovations, major system updates, an oversized backyard and an unbeatable location, this exceptional Winter Park home is truly move-in ready and waiting for its next owner. Call to schedule your appointment today!

259 Orange Terrace Drive, Winter Park
$2,800,000
3 Beds ⋅ 4 Baths ⋅ O6419377 MLS ⋅ 660 BLDG.
Hidden Gem! Designed and built by the acclaimed Phil Kean Design Group, this exceptional luxury townhome offers modern living in one of Downtown Winter Park’s most desirable locations. Situated in the heart of Hannibal Square and just three blocks from Park Avenue, this residence places premier dining, shopping, galleries, museums, Central Park and year-round community events within easy walking distance. Thoughtfully designed with both style and functionality in mind, the home showcases high-end finishes throughout including rich Brazilian walnut flooring, oversized 24 x 48 ceramic tile, coffered ceilings, quartz countertops, custom cabinetry and premium stainless-steel appliances. The chef’s kitchen is anchored by an eight-burner Wolf gas range and a Sub-Zero refrigerator, paired with a hidden pantry discreetly concealed behind custom cabinetry. A striking metal staircase serves as a central architectural feature, adding a contemporary design element that complements the home’s clean lines and sophisticated aesthetic. The open-concept floor plan is filled with natural light, enhanced by expansive windows throughout that frame peaceful green views and mature tree-lined surroundings. The main living areas extend seamlessly to the outdoors, where a first-floor entertaining wet bar with a wine refrigerator opens directly to the private courtyard, creating an effortless indoor-outdoor flow ideal for hosting. The courtyard features a fire pit surrounded by greenery, while the balcony off the main living area includes a summer kitchen. A fenced yard offers privacy and space for pets to enjoy. Designed for today’s lifestyle, the home includes a PRIVATE ELEVATOR servicing all three floors, dual HVAC systems, two tankless water heaters hardwired security cameras and a spacious three-car garage with an electric vehicle charging station and generous storage space. RARELY AVAILABLE in Downtown Winter Park, the oversized THREE CAR GARAGE offers exceptional functionality and flexibility. The private driveway provides additional parking while abundant guest parking nearby makes entertaining easy, an uncommon convenience in a downtown setting. The primary suite occupies the third floor, offering a private retreat with separation from the main living areas. It features a very large owner’s closet filled with natural light and a dedicated vanity area, creating a functional yet refined dressing space. Two additional bedrooms and a dedicated office or den provide flexibility for working from home, accommodating guests or creating additional living space. Each bathroom has been thoughtfully appointed with quality finishes and timeless design. Tucked within a quiet enclave , this residence offers a unique balance of privacy and walkability. The property is adjacent to the recently completed $6.1 million residence of internationally respected architect Kamal Rizk further underscoring the caliber of the surrounding neighborhood. Homes of this quality and location rarely come to market, presenting a truly limited opportunity to own in one of Winter Park’s most sought-after addresses. Combining the architectural vision and craftsmanship of Phil Kean Design Group with luxury finishes, modern conveniences and an exceptional location, this residence offers sophisticated low-maintenance living in the heart of Winter Park’s most vibrant neighborhood. Furniture may convey and pricing upon request. New 10 yr. termite bond will convey with the sale.

660 W Morse Boulevard, Winter Park
$549,000
3 Beds ⋅ 2 Baths ⋅ O6419831 MLS
POOL HOME WITH A WOOD-BURNING FIREPLACE, HOME OFFICE, AND PRIME WINTER PARK LOCATION! This single-family home is packed with the features today's buyers are looking for, including a private pool, spacious backyard, dedicated office/den, and a cozy wood-burning fireplace. Inside, you'll find a versatile floor plan designed for both everyday living and entertaining. The family room is warm and inviting, featuring a beautiful wood-burning fireplace that adds character and charm. A separate office/den provides the flexibility needed for remote work, a playroom, home gym, or additional living space. Step outside to your private backyard oasis, complete with a sparkling swimming pool and plenty of room for outdoor entertaining, family gatherings, pets, and play. The expansive yard offers endless opportunities to create the outdoor lifestyle you've been dreaming of. Situated on a cul-de-sac in a desirable Winter Park neighborhood and zoned for sought-after schools, you'll enjoy easy access to Park Avenue's renowned restaurants, boutique shopping, community events, parks, and entertainment. Conveniently located near Downtown Orlando, major highways, hospitals, and top employers, this home offers the perfect combination of location, comfort, and lifestyle. If you're searching for a Winter Park pool home with a home office, fireplace, large backyard, and exceptional location, this home deserves a spot at the top of your list.

4053 Cool Water Court, Winter Park
$350,000
3 Beds ⋅ 3 Baths ⋅ O6419329 MLS ⋅ Na BLDG.
Welcome to this beautifully maintained townhome located in the heart of Winter Park, Florida. From the moment you arrive, the charming exterior draws you in with its classic stucco finish, attached one-car garage, manicured landscaping, and a welcoming shaded entry framing the front door. Step inside to an inviting foyer featuring high ceilings, modern lighting, and a striking staircase that sets a stylish tone for the rest of the home. The main level transitions into an expansive, light-filled open concept floor plan seamlessly connecting the living room, dining area, and kitchen. Rich wood-look LVP flooring runs throughout the entire lower level, perfectly complementing the crisp neutral walls and providing a cohesive, contemporary aesthetic. The spacious living and dining areas offer an exceptional layout for both daily living and effortless entertaining. Large sliding glass doors at the rear of the home flood the living space with natural light and open directly to a private, screened-in back patio, making it easy to enjoy the Florida breeze. Overlooking the dining area is a spacious kitchen, which features a half-wall cutout that keeps the chef connected to the conversation. Equipped with plenty of warm wood cabinetry, neutral countertops, a deep double sink, and a suite of white appliances, this kitchen is as ample as it is welcoming. A convenient guest half-bathroom with a pedestal sink completes the well-designed ground floor layout. Head upstairs to discover the private living quarters, where the beautiful wood-look flooring continues through the hallway and into each spacious bedroom. The expansive primary suite serves as a true retreat, boasting high vaulted ceilings, an elegant modern ceiling fan, a massive walk-in closet with built-in wire shelving, and a trio of large windows that fill the space with cheerful morning light. This main bedroom easily accommodates king-sized furniture and offers the luxury of an attached en-suite bathroom with dual sinks. The additional bedrooms are equally impressive, each featuring soaring vaulted ceilings, updated stylish ceiling fans, and generous closet space near the dedicated upper-level laundry closet, which comes equipped with a washer and dryer. The outdoor and utility spaces add tremendous value and convenience to this efficient property. The attached garage features an open, clean layout perfect for secure parking, extra storage, or a small home workshop area. At the back of the home, the deep screened-in patio is an ideal spot for outdoor dining, grilling, or relaxing in the shade. The patio steps out onto a beautiful community green belt with pristine lawns and mature shade trees, offering a peaceful residential backdrop. Nestled in a premium, tree-lined enclave, the community boasts pristine, winding roads, manicured privacy hedges, and a scenic retention pond complete with a flowing water fountain feature. This idyllic neighborhood setting perfectly balances the tranquility of nature with outstanding proximity to nearby lakes, parks, major roadways, and local shopping centers. Don't miss the opportunity to own this pristine, move-in ready retreat in one of Central Florida's most highly sought-after locations.

2521 Galliano Circle, Winter Park
$465,000
3 Beds ⋅ 2 Baths ⋅ TB8519391 MLS
Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed for both everyday living and entertaining. The well-appointed kitchen features stainless steel appliances, granite countertops, and ample cabinetry, creating a functional and stylish space for preparing meals and gathering with family and friends. The home's well-maintained interior reflects pride of ownership throughout, offering a warm and welcoming atmosphere from the moment you arrive. The spacious living areas and comfortable bedrooms provide plenty of room to relax and unwind, while the thoughtful layout maximizes both comfort and convenience. Whether you're hosting guests, working from home, or simply enjoying a quiet evening in, this home is designed to fit a variety of lifestyles. Located in the heart of Winter Park, you'll enjoy easy access to the area's renowned dining, shopping, parks, and cultural attractions. Spend weekends exploring the boutiques and cafés along Park Avenue, enjoying a scenic boat tour through Winter Park's picturesque lakes, or visiting nearby gardens, museums, and recreational trails. With convenient access to Downtown Orlando, major employers, top-rated schools, and world-famous attractions, this location offers the perfect balance of suburban charm and urban convenience. Don't miss this opportunity to own a well-cared-for home in one of Central Florida's premier neighborhoods. Schedule your private showing today and discover everything this wonderful Winter Park property has to offer!

3641 Hawthorne Lane, Winter Park
$319,900
3 Beds ⋅ 2 Baths ⋅ TB8522073 MLS
Beautiful 3 bedroom 2 bath duplex in Winter Park in the Winter Park school district on a quiet dead end street near the Winter Park Pines Golf Course. Your new home is freshly painted inside and out, has updated kitchen and bathrooms, stainless steel appliances, new A/C system, new roof, and a new hot water heater. There is no need to worry about your yard, your bushes, or your fence, they are all covered under an inexpensive HOA, what a great deal! This updated home is move in ready and the neighbors are a pleasure! Come see your new home today!

751 Warrenton Road, Winter Park
$899,000
3 Beds ⋅ 4 Baths ⋅ O6416926 MLS ⋅ 1411 BLDG.
Built in 2023 by SGC Homes, this exceptionally livable modern Mediterranean townhome blends comfort and convenience in a classic architectural package, offering 3 bedrooms, 3-1/2 baths, and no shared internal walls, for perfect privacy. There is so much to love here. Situated on a tree-lined brick street in the walkable, convenient area of Minnesota Row, this beauty has been lightly occupied as a second home, and it has never been rented. It is truly a blank slate to make your own. Features that make it special include an open yet cozy floor plan, with a roomy ground floor primary suite which includes a walk-in closet, designer bath with 2 sinks, soaking tub and separate shower, as well as Electrolux washer and dryer, for main-floor convenience. The chef's kitchen with high-end appliances looks into the combined living and dining space. Direct access from the 2-car garage into the kitchen and a very private garden complete the ground floor. Upstairs you'll find two bedrooms, both en suite, separated by an open sitting area for a little extra living space, and a second floor larger laundry with a sink and cabinets for additional storage. Large windows make the rooms light and bright, and the house is ideally situated for maximum privacy. You're going to love the finishes in this unit, including the engineered wood floors, fans in all bedrooms and high end light fixtures, as well tankless hot water, and pavers on the outdoor areas. Easy access to all the options in charming Winter Park including Park Avenue, Winter Park Village, Rollins College and the many parks and green spaces, as well as more shops and dining in College Park. I-4 is minutes away, to get to any place in and around Orlando.

1411 Miller Avenue, Winter Park
$299,999
3 Beds ⋅ 2 Baths ⋅ O6415345 MLS
Enjoy abundant natural light throughout this beautifully maintained one-story, 3-bedroom, 2-bath home, enhanced by soaring vaulted ceilings and an inviting open layout. The kitchen features natural wood cabinetry, stainless steel appliances, and a charming breakfast nook with access to the front patio. The spacious primary suite offers a walk-in closet and private access to the patio. A desirable split-bedroom floor plan provides added privacy, with two guest bedrooms and a full guest bath situated at the front of the home. The bright and versatile patio can be accessed from both the living room and primary suite, creating the perfect space to relax, entertain, or enjoy year-round Florida living. Roof 2023, A/C 2020, Water Heater 2020, pex piping upgrades include pavered driveway, bathrooms updated, patio doors updated, and vinyl fencing in backyard.

2339 Inagua Way, Winter Park
$535,000
3 Beds ⋅ 3 Baths ⋅ O6417190 MLS
Welcome to this beautifully maintained pool home in the highly desirable Lost Creek community, where comfort, functionality, and location come together perfectly. This spacious residence features three generously sized bedrooms and a thoughtfully designed floor plan offering both formal and casual living spaces, including a living room, formal dining room, and a large family room that flows seamlessly into the kitchen beneath soaring vaulted ceilings. The private primary suite serves as a true retreat, dual vanities, a relaxing garden tub, and a separate glass-enclosed shower. The secondary bedrooms are well-proportioned and share a convenient Jack-and-Jill bathroom. Step outside and enjoy Florida living year-round from the covered patio overlooking the screened pool enclosure, creating the perfect space for entertaining or unwinding in privacy. Ideally located in Winter Park's Lost Creek community, residents enjoy easy access to top-rated Seminole County schools, abundant shopping and dining options, major commuter routes, and popular recreational destinations including Red Bug Lake Park with its sports fields, playgrounds, walking trails, tennis courts, and family-friendly activities. This is an exceptional opportunity to enjoy the lifestyle and convenience that make Lost Creek one of the area's most sought-after communities.

1232 Valley Creek Run, Winter Park
$1,399,000
3 Beds ⋅ 3 Baths ⋅ O6417375 MLS ⋅ Vilasa/512 BLDG.
Vilasa Homes — Winter Park’s Expression of Modern Luxury. Perfectly positioned just steps from Park Avenue, this architecturally stunning residence blends refined design with the effortless elegance of Winter Park living. Crafted by Nasrallah Architectural Group, Ted Maines Interiors, and Jordan Builders, this home showcases an Alys Beach–inspired aesthetic with warm wood accents, wrought iron detailing, and two-story block construction for enduring quality. Interiors exude sophistication: soaring 13' ceilings on the main level, 10' upstairs, level-four wall finishes, all-wood flooring, Pella double pain windows and curated designer lighting. The chef’s kitchen is a showpiece— high-end flat panel cabinetry, quartz surfaces, Thermador appliances, and an expansive quartz waterfall island overlooking lush greenery. A private in-unit elevator provides effortless access to the second-floor, enhancing both convenience and sophistication. The second-floor primary retreat offers a serene escape with a loft for office or wellness space, a spa-caliber bath with soaking tub and oversized shower, and generous closet options. Two additional bedrooms provide versatile accommodation for guests, a private office, or fitness space, complemented by a thoughtfully designed shared bath. Outdoor living is exceptional with an expansive 40' x 20' private fenced-in backyard, including a covered patio which extends from the sliding glass doors. A 2-car garage with insulated doors completes the residence. Moments from Winter Park’s finest dining, boutiques, museums, lakes, Hannibal Square and Rollins College. Vilasa Homes offers a rare opportunity to live at the center of it all—wrapped in luxury, design, and timeless style.

512 W Swoope Avenue, Winter Park
$1,849,900
3 Beds ⋅ 4 Baths ⋅ O6416927 MLS ⋅ Douglas Grand BLDG.
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park
$2,350,000
3 Beds ⋅ 3 Baths ⋅ O6414891 MLS ⋅ 140 BLDG.
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.

140 E Morse Boulevard Unit J, Winter Park
$389,000
3 Beds ⋅ 2 Baths ⋅ O6417098 MLS
SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!

1605 Puritan Avenue, Winter Park
$849,000
3 Beds ⋅ 3 Baths ⋅ O6414283 MLS
Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle that defines one of Central Florida’s most coveted communities. Leave the car behind and enjoy easy access to award-winning restaurants, boutique shopping, coffee shops, art galleries, Rollins College, the Winter Park Farmers’ Market, and the Chain of Lakes, all just moments from your front door. Built in 2017 by David Weekley, this thoughtfully designed home combines modern luxury with effortless everyday living. Soaring ceilings, oversized windows, and an open-concept floor plan fill the home with natural light and create an inviting atmosphere throughout. The first-floor primary suite offers a private retreat complete with a spa-inspired bath and spacious walk-in closet, while two additional bedrooms, a full bath, and a dedicated laundry room provide flexibility and convenience. Upstairs, the expansive living and entertaining space serves as the heart of the home. The chef’s kitchen is outfitted with custom cabinetry, granite countertops, premium stainless-steel appliances, a large center island, and a natural gas cooktop—perfect for everything from weeknight dinners to hosting friends and family. Sliding glass doors lead to a spacious balcony with new Trex decking, creating the ideal setting for morning coffee, outdoor dining, or evening cocktails overlooking the neighborhood. With professional landscaping maintained by the HOA, this home offers the ultimate low-maintenance, lock-and-leave lifestyle without sacrificing location or luxury. Opportunities to own in such a highly walkable, centrally located Winter Park setting are exceptionally rare. Experience the convenience, charm, and energy of Park Avenue living while enjoying the privacy and comfort of a beautifully appointed residence. This is Winter Park at its finest.

437 N Capen Avenue, Winter Park
$435,000
3 Beds ⋅ 2 Baths ⋅ C7527235 MLS
Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and dining areas that flow seamlessly into the kitchen, creating a great setup for everyday living and entertaining. The primary suite includes a private bathroom and generous closet space, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to your own private backyard retreat featuring a pool and fully fenced yard, perfect for relaxing, entertaining, and enjoying the Florida lifestyle. Located in a quiet residential neighborhood, this move-in ready home is easy to show and ready for its next owner.

1535 Lawndale Circle, Winter Park
$849,900
3 Beds ⋅ 4 Baths ⋅ O6415981 MLS ⋅ Na BLDG.
Virtually Staged. Welcome to 1265 Arlington Place, a beautifully appointed townhome nestled in the heart of Winter Park's coveted College Quarter - just steps from Rollins College, Park Avenue, and all the dining, shopping, and culture that downtown Winter Park provides. The main level features an open living area flowing into a well-equipped kitchen with granite countertops and solid wood cabinetry, a wet bar for effortless entertaining, a dining room, and a convenient half bath - all finished with rich hardwood floors. French doors lead to a private, fenced yard with two deck spaces, one covered with an awning, perfect for outdoor entertaining or quiet mornings outside. Also on the main level, the spacious primary suite offers an oversized walk-in closet and direct yard access. The luxurious primary bath features double vanities, a soaking tub, and a separate standing shower. Upstairs, a generous bonus living space is flanked by two additional bedrooms, one of which includes an en-suite bath and two walk-in closets - ideal for guests or a home office setup. A full hall bath completes the upper level. Throughout the home, storage has been thoughtfully considered, with generous closet space at every turn. Smart home features including remote-controlled outdoor lighting, garage door, irrigation, and alarm system make this the ultimate lock-and-leave lifestyle home. Residents also enjoy exclusive access to Virginia Heights Park, a private lakefront park reserved for neighborhood use only - a rare amenity in the heart of Winter Park. Come see what makes this property so special!

1265 Arlington Pl, Winter Park
$524,990
3 Beds ⋅ 2 Baths ⋅ O6414677 MLS
Under contract-accepting backup offers. Welcome to Winter Park Pines, one of Winter Park's most desirable and established neighborhoods! Situated on nearly a quarter-acre lot, this beautifully maintained home with fresh interior paint combines modern updates, everyday comfort, and an unbeatable location. The stunning recently updated kitchen serves as the heart of the home, featuring stylish finishes and an inviting space for cooking, entertaining, and gathering. Throughout the home, you'll find attractive flooring with no carpet, offering both a clean, modern look and easy maintenance. Major improvements provide peace of mind, including a new roof and complete re-plumbing completed in 2023. The spacious lot offers plenty of room to enjoy outdoor living, gardening, pets, or future possibilities. Location is everything, and this home delivers. Just steps from Cady Way Pool and the popular Cady Way Trail, you'll enjoy easy access to recreation, fitness, and outdoor activities. Residents also love the convenient proximity to restaurants, shopping, parks, golf, and the charm of Downtown Winter Park. Best of all, there is no HOA, providing added flexibility and freedom. With significant recent updates, a generous lot, and a prime location in highly sought-after Winter Park Pines, this move-in-ready home is a wonderful opportunity to enjoy the very best of Winter Park living.

528 Saint Dunstan Way, Winter Park
$494,900
3 Beds ⋅ 2 Baths ⋅ O6415084 MLS
GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-in porch. Located in desirable Winter Park, 3 blocks from parks, cycling trails, and a public pool, plus minutes from Park Avenue’s shops and restaurants. Enjoy top-rated schools and a lovely, walkable neighborhood. Zoned for BROOKSHIRE ELEMENTARY which is 3 blocks away. New roof (12/2021), New water heater (12/2021), Re-piped (1/2022, no polybutylene), New garage door and opener (2/2022), New AC evaporator coil (6/2022) and New French drain system (6/2023). The home has an irrigation system and irrigation well and New gutters (2/2022). OWNER FINANCING available for owners or flippers. All room dimensions must be independently verified by the buyer.

2715 Prince John Road, Winter Park
$2,695,000
3 Beds ⋅ 4 Baths ⋅ O6412134 MLS ⋅ 1 BLDG.
LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!

413 W Morse Boulevard, Winter Park
$500,000
3 Beds ⋅ 2 Baths ⋅ O6412851 MLS
One or more photo(s) has been virtually staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. This is the kind of home buyers hope to find but rarely do — a beautifully updated mid-century modern with the character of the 1960s and the peace of mind that comes from extensive major improvements already being completed. From the moment you arrive, the oversized 76x133 lot, inviting front porch, and clean curb appeal set the tone. Inside, original terrazzo floors, vaulted ceilings, and a bright open great room create warmth, charm, and livability. French doors open to a screened porch overlooking the spacious backyard. The split-bedroom floor plan features two renovated bathrooms, while the redesigned kitchen offers brand-new appliances, cabinetry, and quartz countertops. A spacious 19x12 family room with tile flooring connects to a large inside laundry room with abundant storage and flexible workspace options. Beyond the visible updates, this home stands apart because so many of the expensive and often-overlooked improvements have already been done, including roof, plumbing re-pipe, electrical updates and full-house rewire, hurricane-impact windows, impact front and rear doors, new mini-split HVAC systems, cast iron drain replacement, interior and exterior paint, and more. A rare opportunity to own a thoughtfully improved home in one of Winter Park’s most desirable locations — with no HOA. WELCOME HOME!

2974 Chantilly Avenue, Winter Park
$384,900
3 Beds ⋅ 2 Baths ⋅ 1079250 MLS
Back on the Market - Buyer Financing fell through. Turnkey and move-in ready! This beautifully updated 3-bedroom, 2-bath home offers modern finishes and an ideal floor plan in a fantastic location! Recent improvements include fresh interior and exterior paint, new flooring throughout, a fully renovated kitchen, and updated bathrooms. Roof (2022) Enjoy comfortable living with thoughtfully updated interiors and flexible living space. The spacious primary suite features an attached bonus room that is perfect for a home office, nursery, fitness space, or private retreat. The community amenities include a playground, tennis courts, and private lake access with a dock, providing plenty of opportunities for recreation and relaxation. Don't miss this opportunity to own this beautifully updated home with outstanding community amenities and convenient access to everything the area has to offer!

1662 Tremont Lane, Winter Park
$384,900
3 Beds ⋅ 2 Baths ⋅ O6414180 MLS
Under contract-accepting backup offers. Back on the Market - Buyer Financing fell through. Turnkey and move-in ready! This beautifully updated 3-bedroom, 2-bath home offers modern finishes and an ideal floor plan in a fantastic location! Recent improvements include fresh interior and exterior paint, new flooring throughout, a fully renovated kitchen, and updated bathrooms. Roof (2022) Enjoy comfortable living with thoughtfully updated interiors and flexible living space. The spacious primary suite features an attached bonus room that is perfect for a home office, nursery, fitness space, or private retreat. The community amenities include a playground, tennis courts, and private lake access with a dock, providing plenty of opportunities for recreation and relaxation. Don’t miss this opportunity to own this beautifully updated home with outstanding community amenities and convenient access to everything the area has to offer!

1662 Tremont Lane, Winter Park
$449,900
3 Beds ⋅ 2 Baths ⋅ O6413717 MLS
Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski lake featuring navigable access to Lake Martha. Reserved primarily for neighborhood residents and their guests, this unique amenity provides an incredible opportunity to enjoy biking, boating, waterskiing, and lakeside recreation just moments from home. This meticulously maintained residence stands out with fresh exterior paint, updated landscaping, and inviting curb appeal. Inside, soaring vaulted ceilings and abundant natural light create an open, airy atmosphere, enhanced by fresh interior paint throughout. The thoughtfully designed split-bedroom floor plan makes excellent use of every square foot, offering comfortable living with no wasted space. An indoor laundry room, spacious 2-car garage, and desirable semi cul-de-sac location add to the home's appeal. Beyond the lake, residents enjoy a community pool, playground, boat launch, and dock along with being located directly across the street from the Cross-Seminole Bike Trail, creating a true lifestyle community. Conveniently located with easy access to SR 417, shopping, dining, and everyday essentials, this home offers the perfect blend of recreation, convenience, and value. Experience the rare opportunity to enjoy private lake-access living in one of the area's most desirable neighborhoods.

5340 N Lake Burkett Lane, Winter Park
$430,000
3 Beds ⋅ 3 Baths ⋅ O6409433 MLS
Under contract-accepting backup offers. "Price Improvement" This charming two-story home situated on a serene conservation lot within the highly sought-after Trinity Bay community in Winter Park. The inviting entrance showcases a covered portico with decorative beams and brick accents. Inside, the spacious living room boasts soaring cathedral ceilings, distinctive round-top windows, and a cozy wood-burning fireplace. A second-story loft overlooks the living area, creating an open and airy feel. Tile flooring graces the foyer, formal dining room, and kitchen, while the eat-in kitchen includes a bright breakfast nook enveloped by bay windows for abundant natural light. The private backyard oasis features a large screened porch, mature shade trees for natural privacy, an automatic irrigation system, and beautifully established landscaping that minimizes maintenance. Residents enjoy an exceptional lifestyle without leaving the neighborhood. Relax by the community pool, take leisurely strolls through the park, or visit the nearby playground. The community also provides direct access to the pristine waters of Lake Burkett (approximately 75 acres) and the connected Lake Martha chain (approximately 30 acres), ideal for boating, fishing, and recreation. The water heater was replaced in 2025, the AC was replaced in late 2021, and the roof in 2017. Trinity Bay is conveniently located adjacent to Trinity Preparatory School, the location is zoned for highly rated Seminole County public schools and offers easy access to major roadways, including SR 417, as well as proximity to the University of Central Florida (UCF), Full Sail University, premier shopping, and fine dining. This well-maintained residence offers a rare combination of character, comfort, and community amenities in a prime Winter Park location.

5530 S Lake Burkett Lane, Winter Park
$649,900
3 Beds ⋅ 2 Baths ⋅ O6412754 MLS
Fully renovated 2 bedroom and 2 bathroom home with a bonus room, ideally located in the heart of Winter Park. Every detail has been updated, including new mechanical systems, electrical, plumbing, custom doors and windows, gutters, stucco finishes, fixtures, fresh landscaping, and new sod. Inside, you'll find an open-concept floor plan with professionally installed luxury vinyl plank flooring (2026) backed by a transferable 10-year warranty. The designer kitchen features butcher block countertops, a farmhouse sink, tile backsplash, and premium stainless steel appliances, including a ZLINE 36" six-burner gas range, ZLINE dishwasher, and KitchenAid refrigerator. A spacious bonus room with vaulted ceilings offers flexible living space for a home office, gym, media room, or playroom. The primary suite includes a spa-inspired bath with floor-to-ceiling porcelain tile, quartz vanity, touch-free LED mirror, and custom doors. Additional upgrades include copper plumbing already installed for a future tankless water heater. Step outside to a fully fenced backyard with gates on both sides and a private patio perfect for entertaining. Located just minutes from Winter Park Village, Park Avenue, Central Park, shopping, dining, entertainment, and Downtown Orlando, this low-maintenance Winter Park home offers exceptional rentability and walkability, and is situated in one of the area's most sought-after locations. Schedule your private showing today.

840 W Canton Avenue, Winter Park
$399,990
3 Beds ⋅ 2 Baths ⋅ S5151098 MLS
No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus room perfect for remote work, creative studio, or guests—functionality of four spaces without the 4-bedroom price premium.Enjoy zero HOA restrictions, significant monthly savings, and peace of mind with a 3-year-old roof (transferable documentation included). Features include updated flooring throughout (no carpet), fully fenced backyard, and 2-car garage. Zoned for desirable Seminole County schools (Eastbrook Elementary/Lake Howell High) with quick access to SR-436, shopping, and downtown Winter Park. Ideal for remote professionals, small families, or savvy buyers seeking low-maintenance ownership with room to work and grow. Quick closing available. Schedule today!

5503 Albert Drive, Winter Park
$550,000
3 Beds ⋅ 4 Baths ⋅ O6412954 MLS ⋅ Bldg 1 BLDG.
Modern living meets unbeatable location in this stunning 3 bedroom, 3.5 bathroom home nestled in the highly sought-after Urban Green Community. Built in 2022, this move-in ready residence showcases sleek, contemporary finishes throughout all three levels. Step up to a welcoming covered and pavered front porch, fenced-in front yard, and into a thoughtfully designed layout. The first floor offers a private bedroom with its own walk in closet and ensuite—perfect for guests or a home office. On the second floor, enjoy open-concept living with a bright and airy great room featuring high ceilings, recessed lighting, and seamless access to an oversized balcony through sliding glass doors. The modern kitchen is a showstopper, complete with quartz countertops, stainless steel appliances, a walk-in pantry, white shaker cabinets and a large center island with breakfast bar seating. Upstairs, you'll find two additional bedrooms, including the spacious primary suite with a walk-in closet, double vanity, glass-enclosed shower, and built-in shelving. The third bedroom also includes its own ensuite for added privacy and comfort. Additional highlights include an oversized rear-entry 2-car garage, laundry room, ample storage, and low-maintenance living. Enjoy unbeatable proximity to I-4, Downtown Orlando, Dubsdread Golf Course, Rollins College, Park Avenue, and Winter Park Village—offering endless dining, shopping, and entertainment options. This modern gem offers the best of both worlds: a turnkey home in a central, vibrant location. Don’t miss your chance to own in one of Orlando’s most desirable areas!

1250 Formosa Avenue, Winter Park
$360,000
3 Beds ⋅ 2 Baths ⋅ O6412514 MLS
Under contract-accepting backup offers. Virtually Staged. FABULOUS 3 bedroom 2 bath RENOVATED home with a 1 car garage located in a PRIME LOCATION!! Perfect for the first time homebuyer, investor or someone looking to downsize. The large family room benefits from natural lighting provided by the NEW WINDOWS installed(2024) throughout the ENTIRE house. The open kitchen overlooks the covered porch and large, FULLY FENCED backyard. The primary bedroom has LPV flooring with an UPDATED bathroom. NEWER carpets in the other two bedrooms. Second bath has a new toilet with a bidet, a tile bath/shower combo, and an updated vanity. NEW lighting, outlet and switch plate covers throughout. A NEW roof ridge vent was added for extra ventilation! NEW LANDSCAPING in the front. NEW DRAINFIELD (2026), water heater (2023), roof(2021). It is in Seminole County school district, 15 minutes to UCF, 5 minutes to shopping, and 10 minutes to the highway. HURRY, you don't want to miss this opportunity!!

7577 Dockside Street, Winter Park
$3,500,000
3 Beds ⋅ 5 Baths ⋅ O6411141 MLS ⋅ Park Hill BLDG.
Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.

649 N Park Avenue, Winter Park
$1,599,000
3 Beds ⋅ 5 Baths ⋅ O6412554 MLS
Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private courtyard entrance sets the tone, creating a serene arrival and sense of retreat from the moment you step onto the property. Inside, polished concrete floors and an open, light-filled layout define the home's contemporary aesthetic, with clean lines and seamless flow designed for everyday living and effortless entertaining. Step outside to your own private oasis- complete with a pool and tranquil outdoor spaces- perfect for enjoying Florida living year-round. The home's prime location allows for an exceptional lifestyle- just a short stroll to Park Avenue's renowned shops and dining and an even shorter stroll to the golf course. Offering a unique combination of modern design and in-town convenience, this is Winter Park living at its most elevated.

641 Northwood Circle, Winter Park
$699,900
3 Beds ⋅ 3 Baths ⋅ O6412589 MLS
**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2022. Taken to the slab and studs, this Winter Park residence was entirely rebuilt with new roof trusses, all-new electrical, new AC system (inside and out), tankless water heater, new plumbing, and smart irrigation — delivering true new construction quality in an established neighborhood. Located steps from Winter Park Village, Park Avenue, Whole Foods, Starbucks, Publix, cinema, restaurants, and more. Arrive home to a grand 51' custom driveway flanked by mature Italian cypress trees, sculptural landscaping, and elegant iron railing — pulling directly to your covered front porch entry. No garage means no wasted space — just a clean, architectural arrival experience designed to impress. Inside, light-filled interiors with soaring 6" baseboards, full custom tile flooring, and an abundance of natural light create a gallery-like aesthetic that feels curated, not cookie-cutter. Custom liner windows in the dining room and primary suite flood the home with natural light while adding unmistakable architectural character. **The Kitchen:** - Designer floating shelves - Smart range and under-counter built-in microwave - Under-cabinet and island LED lighting - Decorative pendants and ambient lighting throughout **The Primary Suite:** A private retreat with ceiling-mounted rain shower and spa-like finishes designed to decompress after a walkable night out on Park Avenue. **Smart Home Ready:** - New AC system (inside and out) with smart thermostat - Tankless water heater and fully new plumbing - Smart lock entry - Google Nest doorbell with two-way audio - Smart soffit exterior lighting - Weather-monitored smart irrigation **Out Back:** A fully private PVC-fenced backyard sanctuary — spacious enough for pets, entertaining, and room to roam. A covered porcelain tile patio plus a separate fire pit slab make this an outdoor living extension you'll actually use year-round in the Florida lifestyle. Over 300 sq ft of additional space was added to accommodate two additional bathrooms, interior laundry, and a layout built for real life — including a new stacked washer and dryer. Properties combining true gut-renovation quality, luxury designer touches, smart technology, and this rare walkable Winter Park address don't last. Move-in ready — and built to last for decades.

860 N Denning Drive, Winter Park
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