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$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
$375,000
4 Beds ⋅ 3 Baths ⋅ O6423782 MLS
Under contract-accepting backup offers. **MULTIPLE OFFERS - SUBMIT YOUR HIGHEST AND BEST BY 5PM ON MONDAY 7/13** Bank-owned opportunity in Winter Park near Interlachen Country Club, Park Avenue, Full Sail, Rollins, and UCF. Set in Winter Woods, one of the area’s established neighborhoods, this 4/2.5 two-story home sits on a fenced lot w/pool and offers 1,776 sqft, block and brick construction, a 2-car garage, and a primary bedroom with a walk-in closet and private balcony overlooking the pool. The home needs a full renovation, including a new roof. Flooring, kitchen, and HVAC, and the property is priced accordingly. Optional HOA and flood zone X help keep carrying costs simple. Sold As-Is by the REO seller. Cash or renovation financing only.

2189 Sussex Road, Winter Park
$379,900
4 Beds ⋅ 2 Baths ⋅ O6423739 MLS
**This property qualifies for $5,000 Buyer Credit** Updated 4/2 with New Roof, New AC (x2), and New Dual-pane Windows | No HOA | Top-Rated Winter Park School Zone ... Welcome to low-maintenance Winter Park living at 4965 Orange Ave in 32792 with no HOA constraints or fees. Nestled on a quiet lot zoned for top-rated Orange County Public Schools Lakemont Elementary, Maitland Middle, and Winter Park High School, this move-in ready four-bedroom single-family home offers major high-ticket capital improvements already completed. Upgrades include a NEW Roof, two NEW A/C systems for dual-zone energy efficiency, NEW dual-pane insulated windows, fresh interior and exterior paint, and modern fixtures throughout. The carpet-free interior boasts easy-to-clean polished terrazzo and modern ceramic tile flooring, an updated galley kitchen with stainless steel appliances and solid wood cabinets, and two thoughtfully remodeled bathrooms. Designed with incredible layout versatility, the split four-bedroom floor plan includes direct exterior access through sliding glass doors, making it exceptionally well-suited for a multi-generational setup, in-law suite, private guest retreat, or dedicated home office. Outside, the expansive fully fenced backyard provides ample room for pets, outdoor entertaining, or a future pool, while the attached carport offers covered parking and a dedicated laundry utility storage room. Enjoy an unbeatable Central Florida location just minutes from Park Avenue dining, boutique shopping, local parks, and major Orlando commute routes. $5,000 Buyer Credit for qualified buyers. Call for details.

4965 Orange Avenue, Winter Park
$1,690,000
4 Beds ⋅ 3 Baths ⋅ O6423883 MLS
A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Substantial homesite, prime location, endless potential. Coming soon. Reach out to the listing agent if you would like more information about the property.

708 Balmoral Road, Winter Park
$639,000
4 Beds ⋅ 3 Baths ⋅ O6422937 MLS
Under contract-accepting backup offers. Welcome to this gorgeous 4-bedroom, 3-bathroom WINTER PARK home that perfectly blends elegance, comfort, and functionality. From the moment you step inside, you'll be impressed by the soaring 12–14-foot ceilings, beautiful CROWN MOLDINGS, and classic PLANTATION SHUTTERS that add timeless charm throughout. Designed with an exceptional flow, this home features formal living and dining rooms, along with a spacious family room centered around a charming fireplace, creating a warm and inviting space for relaxing or gathering with family and friends. The family room seamlessly connects to the heart of the home—a stunning CUSTOM chef's kitchen equipped with high-end appliances, thoughtfully designed cabinet organizers, and abundant workspace, making it a dream for cooking and entertaining. The desirable split floor plan offers both privacy and flexibility, with two bedrooms located in the right wing and two in the left, including a spacious primary suite. Every detail has been carefully considered to create a warm, inviting atmosphere that's ideal for everyday living and hosting guests. Step outside to your private backyard oasis, where a large swimming pool and spacious outdoor living area create the perfect setting for entertaining, weekend gatherings, or simply relaxing. The fully fenced yard provides both privacy and plenty of room to enjoy Florida living year-round. Additional highlights include a **NEW ROOF**installed in 2021**,** NEW LUXURY VYNIL PLANKS FLOORING** in 4 rooms, brand NEW interior painting offering added value and peace of mind for the next owner. This exceptional Winter Park home is a true showstopper that offers luxury, comfort, and timeless appeal. Don't miss the opportunity to make it yours!

1908 Cyril Court, Winter Park
$600,000
2 Beds ⋅ 2 Baths ⋅ O6423146 MLS
Under contract-accepting backup offers. Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom home! The yard is large. Large shed in the yard to store all of your yard essentials. You will love the area and the convenience to what makes this area special...steps from East End Market, lots of amazing restaurants, shopping, Leu Gardens, and so much more. Updates to the home include: Roof: 2020, HVAC 2019, Elecrical - new utility box, Plumbing: re-plumbed Kitchen and both bathrooms. Welcome Home.

2824 Woodside Avenue, Winter Park
$3,395,000
6 Beds ⋅ 8 Baths ⋅ O6422550 MLS
Come tour this brand new, elaborately finished luxury home in Winter Park! Designed and constructed by a well-established, award-winning custom home builder, no expense has been spared. This home is truly a leader in its class! Located just a short walk to the esteemed Audobon K-8 school, East End market, restaurants, shopping, Blue Jacket Park, Baldwin Park. Just a short drive to Park Avenue restaurants and shopping. As you pull up to this vast estate home, the dimensional architectural detail on the home on a huge lot boasts a commanding presence. The 12 foot ceilings on the first floor and 10 foot ceilings on the second floor give the home a voluminous feel throughout. The first floor features a huge master suite with an accessible washer and dryer off the giant walk-in closet, plus an additional full guest suite and separate office. The gourmet kitchen features luxury custom cabinets, an accent island with exotic granite counter tops. Thermador appliances outfit the main kitchen as follows: Large 30” refrigerator and 30” freezer towers, 48” dual oven gas range with ornamental hood, dishwasher and microwave drawer. Flanking the main kitchen is a spacious Butler’s pantry with its own sink, refrigerator and dishwasher. Just off the Butler’s pantry is both a mudroom just inside the garage, and additional air-conditioned storage room. Over the garage is a separate bonus/flex room with its own full bath and closet. Upstairs is a huge loft living area plus three full bedroom suites and laundry room. The home is ornamented with expensive fit and finishes as follows: extensive architectural ceiling detail with cove lighting, lighting fixtures, plumbing fixtures, hardware, tile, level 5 smooth drywall finishes, designer wallpaper, and more! Designed with energy efficiency in mind, Natural gas fuels two tankless water heaters, the kitchen range, summer kitchen grill and pool/spa heater. Elaborate landscaping provides beautiful accents and plenty of privacy in the rear outdoor living area. Outdoor living includes a huge covered lanai with retractable screens, summer kitchen, and heated salt-water swimming pool with integrated spa and pool deck, plus outdoor shower and separate pool bath. 10' tall pocket sliding glass doors can open the great-room wall completely to integrate your indoor and outdoor entertaining. Great fortune comes to those who TAKE IMMEDIATE ACTION when opportunity presents itself! Come tour your magnificent new luxury home today!

2905 Parkland Drive, Winter Park
$2,569,999
5 Beds ⋅ 5 Baths ⋅ O6421927 MLS
Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredible location come together on a quiet tree-lined street. Ideally positioned just a short golf cart ride from Park Avenue, the YMCA, and Interlachen Country Club, this home offers the perfect combination of privacy, convenience, and refined Winter Park living. From the moment you step inside, an impressive foyer greets you, showcasing intricate marble mosaic tile that sets the tone for the craftsmanship found throughout. The open-concept floor plan flows effortlessly into the main living spaces, where the spacious living room serves as the centerpiece of the home with elegant archways, custom shelving with LED underlighting, warm wood beam accents, and a stunning stone-wrapped fireplace creating the perfect balance of sophistication and comfort. Designed for both everyday living and entertaining, the dining room features a beautiful dry bar complete with a wine refrigerator, while the chef’s kitchen is truly the heart of the home. Outfitted with Calacatta quartz countertops, a paneled built-in refrigerator, a full suite of Thermador appliances, and a spacious walk-in pantry, every detail has been thoughtfully selected to deliver both style and functionality. The first-floor primary suite provides a private retreat with generous proportions and a spa-inspired bathroom featuring marble mosaic tile, dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large walk-in closet. A rare additional first-floor guest suite adds incredible flexibility for family and visitors. Upstairs, the home continues to impress with a spacious loft, a conveniently located laundry room, and three additional bedrooms, offering plenty of room for everyone. Step outside and experience your personal outdoor oasis with a spacious covered lanai featuring a full summer kitchen overlooking the sparkling pool and spa. The oversized backyard provides an abundance of green space, creating the perfect setting for relaxing, entertaining, or enjoying time with family. Additional highlights include impact-rated windows and doors, premium finishes throughout, and an unbeatable location surrounded by some of Winter Park’s most desirable amenities. This is a rare opportunity to own a brand-new home combining thoughtful design, exceptional craftsmanship, and one of Central Florida’s most sought-after lifestyles.

1754 Taylor Avenue, Winter Park
$315,000
2 Beds ⋅ 2 Baths ⋅ O6422583 MLS
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The two-bedroom configuration provides flexibility for residents, visitors, a home office, or a hobby room, while two full bathrooms add convenience for daily routines. Outdoor living includes a covered and screened patio, creating a comfortable space to enjoy fresh air, outdoor dining, or quiet downtime while staying shaded and protected from the elements. Located in Winter Park, the home is close to shopping, dining, parks, schools, and everyday conveniences. The area offers access to nearby destinations such as Winter Park Village, Park Avenue, local recreation, and major roadways connecting to Maitland, Orlando, and surrounding Central Florida communities.

5781 Shale Court, Winter Park
$625,000
4 Beds ⋅ 2 Baths ⋅ O6415387 MLS
Under contract-accepting backup offers. Nestled within the gated community of Hawks Crest, this thoughtfully designed single-story residence offers an exceptional blend of comfort, style and convenience in the heart of Winter Park. Spanning 1,920 square feet, this home features an open-concept floor plan that seamlessly connects the living, dining and kitchen areas, creating an inviting setting for both everyday living and entertaining. The kitchen serves as the centerpiece of the home, appointed with granite countertops, stainless steel appliances and a spacious center island with seating. The private owner's suite offers a walk-in closet and a well-appointed bath, while three additional bedrooms provide flexibility for guests, a home office or evolving lifestyle needs. A covered lanai overlooks the tranquil pond, creating the perfect backdrop for outdoor relaxation and year-round Florida living. Residents of Hawks Crest enjoy access to an impressive collection of amenities, including a clubhouse, fitness center, resort-style pool, splash pad, dog park, playgrounds, virtual guard gate and private access to Lake Howell for kayaking and paddleboarding. Ideally located just minutes from highways, Park Avenue, downtown Maitland, top-rated schools, Foxtail Coffee and Kelly's Ice Cream, this residence offers the opportunity to enjoy one of Winter Park's most sought-after gated communities.

2087 Laurelwood Way, Winter Park
$4,900,000
5 Beds ⋅ 6 Baths ⋅ O6413198 MLS
A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom build by Maroon Fine Homes and renovated in 2024 by Greg Hardwick, this estate blends timeless architecture with comfortable sophistication and functionality. A stone’s throw to the celebrated shops and dining of Park Avenue, Rollins College, Winter Park Golf Course, and the serene beauty of Kraft Azalea Gardens, the location is simply unrivaled. This extraordinary residence spans nearly 5,000 sf with a flowing floor plan designed for entertaining and everyday living. Solid wood artisan arched doors anchor the inviting foyer with porcelain marble tile, volume ceilings, and a sleek iron circular staircase as a focal point. An open dining and intimate living room layout are flanked by windows and clear view doors, which bring in natural light. The spaces share a unique temperature-controlled wine cellar finished with seamless glass and ambient lighting, adding a dramatic touch for the discerning enthusiast. The main level centers around a spacious kitchen that enjoys a dedicated eat-in space and counter seating, with a family room that overlooks the expansive backyard. A dedicated wet bar and first-floor bonus room make this home ideal for hosting at any scale. The outdoor living rivals a 5-star resort, recently reimagined in 2026 by Signature Landscaping. An immense new pool with a sun shelf anchors the outdoor living experience, surrounded by a lush turf courtyard, sport court, and a covered lanai with generous pavered decking and a summer kitchen. A cozy gas fire pit with casual seating invites you to take in the evening breezes. Privacy abounds with mature Japanese blueberry trees and Podocarpus hedges. A dedicated side yard dog run completes this outdoor haven. The main floor is home to the first-floor primary suite, with privacy doors separating this section of the home. It is a true retreat unto itself, offering a sunlit sitting area with doors leading to the backyard, a beautifully appointed bath, a dedicated home office, and two custom-fitted walk-in closets, one of which includes a secondary laundry area. The spa-inspired bathroom has it all, featuring a generous shower with a soaking tub within the enclosure for the ultimate relaxation experience. A first-floor guest suite, thoughtfully designed with a split-plan layout, provides privacy for visitors, while three additional ensuite bedrooms and a bonus landing are located upstairs. The oversized three-car side-loading garage is air-conditioned and features upgraded flooring, while a generous circular drive and mature front hedge offer a gracious arrival experience and an added layer of privacy. A rare convergence of premier location, architectural distinction, and meticulous renovation — this is Winter Park luxury living at its finest.

1180 Via Lugano, Winter Park
$2,549,000
5 Beds ⋅ 5 Baths ⋅ O6421690 MLS
Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!

1823 Sunset Drive, 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
$275,000
2 Beds ⋅ 2 Baths ⋅ O6422691 MLS ⋅ 18d BLDG.
Under contract-accepting backup offers. Welcome home to carefree lakefront living in the heart of Winter Park, where everyday life is complemented by breathtaking sunsets over beautiful Lake Killarney and one of Central Florida's most walkable locations. Nestled within the Chateaux Du Lac lakefront community, this beautifully updated second-floor condominium offers 2 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living. Stepping inside, plantation shutters throughout the home create a timeless look while allowing natural light to fill the space. The spacious living and dining areas flow seamlessly together, making entertaining both easy and enjoyable. The updated kitchen is sure to impress with quartz countertops, a center island, modern subway tile backsplash, stainless steel appliances, and recessed lighting that completes the contemporary design. The owner's suite provides a relaxing retreat complete with an updated ensuite bathroom featuring stunning floor-to-ceiling herringbone-style subway tile, an overhead rain showerhead, and modern finishes. The guest bedroom is generously sized and offers a large walk-in closet, while the second bathroom has been beautifully updated to match with the same designer tilework and rain showerhead. Sliding glass doors lead out to your private balcony, creating the perfect place to enjoy your morning coffee or unwind in the evening after a day on the lake. A brand-new water heater installed in 2026 provides added peace of mind. Residents of Chateaux Du Lac enjoy an exceptional lakefront lifestyle with access to a heated swimming pool, clubhouse, community deck overlooking Lake Killarney, private boat ramp, BBQ grilling area, saunas, kayak and paddleboard storage, and updated on-site laundry facilities. Whether you enjoy boating, skiing, paddleboarding, fishing, or simply taking in spectacular sunset views, this amenity-rich community offers everything you need to embrace the Florida lifestyle. Perfectly positioned just moments from Park Avenue, you'll enjoy easy access to locally owned restaurants, boutique shopping, cafés, Trader Joe's, the Winter Park Village, movie theater, farmers markets, and the nationally recognized Winter Park Sidewalk Art Festival. With convenient access to I-4, commuting throughout the Orlando area is effortless while still enjoying the charm and elegance that make Winter Park one of the area's most desirable communities. Schedule your showing today!

1500 Gay Road Unit 18D, Winter Park
$12,500,000
6 Beds ⋅ 10 Baths ⋅ A11776219 MLS
Lakefront estate featuring 6 bed, 7 full and 3 half baths. over 11,000 SqFt on 2,7 acres. Resort-style pool, summer kitchen, 6-car garage, fully fenced with a private gate. 120 feet of lake front on Winter Park Chain of Lakes, private boat dock, and boat lift. All bedrooms with en-suite bathrooms, fireplace, sauna, fitness room, office room, and expansive walk-in closets. Lutron system, crystal chandelier, marble and wood floors, dual soaring staircase, private elevator. Welcome to Maison du Lac – a breathtaking lakefront estate that epitomizes unrivaled luxury, timeless elegance, and an extraordinary lifestyle. Situated on an expansive 2.7-acre lot along the prestigious Winter Park Chain of Lakes, this extraordinary residence showcases over 120 feet of pristine lakefront with sweeping panoramic views of the longest stretch of Lake Maitland.Blending classic Mediterranean architecture with state-of-the-art modern enhancements, Maison du Lac is a stunning fusion of enduring charm and contemporary sophistication. Originally constructed with timeless materials – including stucco exteriors and expansive windows – the home has been meticulously transformed into an 11,668-square-foot architectural masterpiece. Clean lines and open-concept living harmonize with rich textures and refined details, resulting in an environment that is both stately and smart.Upon entering through the grand 14-foot custom iron door, you are greeted by soaring dual staircases and exquisite finishes in marble, granite, and intricate moldings that reflect the home’s bespoke craftsmanship. A showstopping, $250,000 crystal chandelier—custom-designed and operable at the touch of a button—crowns the expansive great room, setting a dazzling tone for the professionally curated interiors. A private elevator adds convenience and accessibility across all levels of the home.The fully reimagined kitchen is a culinary showpiece, featuring top-of-the-line Wolf appliances, gleaming Cambria countertops, a large walk-in pantry, and expansive prep space ideal for entertaining at any scale. Whether hosting a lavish dinner or a relaxed brunch, the kitchen delivers both impeccable style and everyday functionality.The private master wing is an indulgent retreat, complete with a cozy fireplace, executive office, sauna, fitness room, and dual custom walk-in closets. Five additional en-suite bedrooms are thoughtfully positioned for maximum privacy, offering luxurious accommodations for family and guests. With seven full bathrooms and three half baths, the residence is ideally equipped for both refined daily living and grand-scale entertaining.For effortless indoor-outdoor living, multiple entertainment spaces flow seamlessly onto a sprawling lakefront patio. The outdoor summer kitchen, complete with a powered screen enclosure, provides the perfect setting for alfresco dining while enjoying sunset views over the water. A brand-new dock with a boat lift invites leisurely days spent boating, fishing, or simply relaxing on the lake.Outside, the estate continues to impress. Two serene fishponds with fountains create a tranquil sense of arrival, while the fully fenced and gated grounds ensure ultimate privacy. The residence is equipped with a full-home LUTRON smart system, offering intuitive control of lighting, ambiance, and automation. Additional features include a six-car garage, a resort-style swimming pool, newly updated landscaping, and custom exterior lighting.Maison du Lac is more than a home, it’s a lifestyle of distinction, privacy, and effortless sophistication. This is the lakefront living at its finest.

570 Manor Road Unit Maitland, 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
$190,000
1 Beds ⋅ 1 Baths ⋅ R4911491 MLS ⋅ 109 BLDG.
Welcome to this beautifully updated one-bedroom, one-bath condo in the heart of Winter Park. Thoughtfully maintained and move-in ready, this inviting home offers a bright, clean interior with tasteful finishes and a functional layout designed for comfortable, low-maintenance living. A spacious screened porch overlooks a serene courtyard, creating the perfect spot to enjoy your morning coffee or unwind at the end of the day. Perfectly situated, this home is nestled between two beautiful parks—Mead Botanical Garden, just steps away, and Seven Oaks Park—offering easy access to nature, walking paths, and green space. You're also just minutes from Rollins College, the boutiques and restaurants of Park Avenue, AdventHealth Winter Park, and the vibrant Mills 50 District. Outdoor enthusiasts will appreciate the nearby Cady Way Trail, Orlando Urban Trail, Dinky Line Trail, and Baldwin Park, all just a short bike ride away. With convenient access to Orlando Avenue (US-17/92), I-4, and both the Winter Park and AdventHealth SunRail stations, commuting throughout Central Florida is effortless. Located in the desirable Mead Garden Condominiums community with a sparkling pool and beautifully maintained grounds, this charming condo offers an exceptional blend of comfort, convenience, and the best of the Winter Park lifestyle.

1250 S Denning Drive Unit 109, Winter Park
$280,000
2 Beds ⋅ 2 Baths ⋅ O6422366 MLS ⋅ Na BLDG.
Charming two-bedroom, two-bath condominium available in Winter Park. The reserve is fully funded, and monthly condominium fees are low. A comfortable foyer welcomes you inside, leading down the hallway to the second bedroom at the front of the home, where a large window overlooks the front green space. The kitchen opens to a bright, inviting space with skylights that bring natural light into the combined living and dining area. A fireplace adds warmth to the room, while sliding glass doors lead to a private screened enclosure overlooking additional green space at the rear of the property. Ideally positioned within the home, the kitchen features all-new appliances and an oversized pantry with spice shelving for easy organization. The primary bedroom offers an inviting entrance with closet space upon entry. Sliding glass doors fill the room with soft natural light, creating a calm and peaceful atmosphere. The primary bath includes a double vanity and additional deep closet space. From the bedroom, step out to the screened enclosure and enjoy quiet moments in the Florida breeze. Lazy Oaks Condominium is a charming, peaceful community in Winter Park. Conveniently located near shopping, restaurants, schools, and universities, it offers an inviting place to relax and call home.

5184 Lazy Oaks Drive, 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
$799,000
4 Beds ⋅ 3 Baths ⋅ O6422168 MLS
Under contract-accepting backup offers. Completely reimagined with an extensive top-to-bottom renovation, this stunning four-bedroom, three-bathroom pool home offers over 2,300 square feet of beautifully curated living space in one of Winter Park's most desirable locations. Every detail was thoughtfully selected to blend timeless design with modern functionality, creating a truly move-in-ready home. Inside, large wood-look plank tile flooring installed throughout in 2024 creates a seamless flow, complemented by recessed lighting, plantation shutters, all-new designer lighting and ceiling fans, and energy-efficient windows replaced in 2024. A cozy wood-burning fireplace provides character to the beautiful living space while French doors installed in 2024 provide effortless access to the outdoor living space. Additional upgrades completed in 2024 include blown-in insulation and a gas tankless water heater. The showstopping kitchen was completely remodeled in 2024 and is designed to impress. Custom hardwood cabinetry accented with elegant gold hardware is paired with luxurious quartz countertops and a dramatic full-height quartz backsplash. A large center island with seating for four, a black farmhouse sink, pot filler, and abundant prep space make this kitchen equally suited for everyday living and entertaining. Split from the secondary bedrooms for added privacy, the spacious primary suite is a peaceful retreat featuring French doors leading directly to the pool, a dedicated makeup vanity, walk-in closet, and a beautifully renovated ensuite bathroom with a double vanity and an oversized tiled shower enclosed by frameless glass. All three bathrooms were tastefully remodeled in 2024 with timeless, high-end finishes. The oversized laundry room is as functional as it is attractive, offering built-in cabinetry for exceptional storage along with an included washer and dryer. Step outside to your own private backyard oasis situated on a beautifully landscaped .26-acre lot. The screened in-ground pool was resurfaced with mini pebble finishes in 2025, while a custom flagstone outdoor shower with a decorative rock bed creates a true resort-inspired atmosphere. Additional exterior improvements completed in 2024 include new exterior doors, gutters, French drains, and an updated two-car garage featuring epoxy flooring along with new torsion springs and rollers. Ideally located just minutes from UCF, Rollins College, Full Sail University, AdventHealth Winter Park, the Crosby Wellness Center, Winter Park Pines Golf Club, and the Cady Way Trail, residents also enjoy access to Cady Way Park with its community pool, playground, beach volleyball courts, tennis courts, and pickleball courts. Zoned for highly rated Aloma Elementary, Glenridge Middle School, and Winter Park High School, this exceptional home combines a remarkable renovation with an unbeatable Winter Park lifestyle. ROOF - 2024 HVAC - 2024 ELECTRICAL - 2024 PLUMBING - 2024 TANKLESS WATER HEATER - 2024

729 Monmouth Way, Winter Park
$279,900
2 Beds ⋅ 2 Baths ⋅ O6421422 MLS ⋅ 19 BLDG.
Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, 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
$799,900
4 Beds ⋅ 3 Baths ⋅ O6421873 MLS
JUST REDUCED! Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-bathroom residence where true pride of ownership shines through every detail. Absolutely turn-key and loaded with premium updates throughout, such as new electrical panel, newer water heater, new pool pavers, upgraded engineered floors throughout & much more! This home offers the perfect blend of modern luxury and effortless entertaining.The heart of the home seamlessly connects to the outdoors with a brilliant kitchen pass-through window, serving an enormous covered patio. Step into your own private, tranquil backyard oasis featuring a freshly resurfaced pool surrounded by stunning new pavers & large Perolga. Whether you are hosting a summer barbecue or rinsing off in your convenient outdoor shower after a swim, this backyard is built for Florida living at its finest. Property is zoned for highly rated schools with convenient location just moments away from Cady Way Park & trails, Rollins, UCF, & Full Sail Colleges, just 4 miles from vibrant dining(Park Ave) & premier shopping.

722 S Ranger Boulevard, Winter Park
$142,500
1 Beds ⋅ 1 Baths ⋅ O6420915 MLS ⋅ 14 BLDG.
Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer ~ Recently UPDATED and ready for its next owner, this light-filled FIRST FLOOR condo unit offers LOW MAINTENANCE LIVING in the desirable Stratford community of Winter Park – with a monthly HOA that's lower than many comparable communities! Step inside through the semi-private INTERIOR ENTRY to an OPEN CONCEPT floor plan featuring updated bathroom finishes, WOOD LAMINATE & TILE FLOORING throughout, and a spacious living and dining area designed for everyday comfort and easy entertaining. The kitchen is equipped with STAINLESS STEEL APPLIANCES, breakfast bar seating, and a seamless connection to the main living spaces. A convenient IN-UNIT LAUNDRY closet adds to the home's functionality, while sliding glass doors lead out to a SCREENED LANAI overlooking a large green space for the perfect spot to enjoy your morning coffee or unwind at the end of the day. Stratford is a beautifully maintained community offering a park-like setting complete with a COMMUNITY POOL and peaceful surroundings thanks to the mature trees, making it easy to enjoy the Florida lifestyle without the upkeep of a single-family home. Ideally located at the corner of Lake Howell Road and Howell Branch Road with quick access to SR 436, you will appreciate being just minutes from abundant shopping, dining, medical services, parks, and everyday conveniences. Whether you are searching for your first home, a seasonal retreat, or an investment opportunity, this well-maintained Winter Park condo is one you won't want to miss. Call today to schedule a tour!

283 Lewfield Circle Unit 283, 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
$285,000
2 Beds ⋅ 2 Baths ⋅ O6421135 MLS ⋅ Bldg 16 BLDG.
Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile backsplash, abundant cabinetry, a pull-out spice rack, trash/recycling cabinet, and a built-in storage unit. Sliding glass doors open to the private front courtyard, filling the space with natural light. Conveniently located laundry area, complete with washer and dryer, is tucked within the kitchen. The spacious living room features a cozy wood-burning fireplace and flows seamlessly into the dining area beneath soaring vaulted ceilings accented by skylights. Sliding glass doors lead to a screened lanai with a slate tile floor and a storage closet—an ideal spot to relax and enjoy Florida living. The primary suite also opens directly to the lanai and offers a beautifully renovated en-suite bath with a luxurious walk-in shower, updated vanity, linen cabinet, and a custom walk-in closet with built-in organizers. The front bedroom also includes a generous walk-in closet. Enjoy added privacy with a picturesque, tree-lined green space across the street rather than neighboring condos directly in front. Two dedicated parking spaces are conveniently located just outside your door. Cedarwood Village offers an exceptional location directly across from Casselberry Commons Shopping Plaza and is just minutes from Full Sail University, UCF, and Rollins College. Residents enjoy a community swimming pool, tennis courts with pickleball lines, and designated dog-walking areas. Additional highlights include a new roof and skylights installed in 2020. Monthly HOA fees cover exterior maintenance, lawn care, and community amenities, making this the perfect opportunity to enjoy carefree living in one of the area's most desirable communities.

2372 Sun Valley Circle Unit 2372, 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
$575,000
2 Beds ⋅ 3 Baths ⋅ O6421299 MLS ⋅ 1122 BLDG.
Under contract-accepting backup offers. Completely reimagined in 2025, this stunning 2-bedroom, 2.5-bath townhome offers the perfect blend of modern luxury and an unbeatable Winter Park location. Just minutes from Rollins College, Park Avenue, boutique shopping, award-winning dining, and everything that makes Winter Park so desirable, this move-in-ready home has been thoughtfully renovated from top to bottom with timeless, designer-selected finishes. The heart of the home is the beautifully redesigned kitchen featuring Sarah Sherman Samuel cabinetry and hardware, gorgeous marble countertops, a custom marble ledge, and all-new appliances. Throughout the home, you'll find new flooring, smooth-finished walls, fresh interior paint, recessed lighting with dimmers, updated electrical, new interior doors and hardware, and new baseboards, creating a clean, sophisticated aesthetic. Upstairs, both spacious bedrooms feature beautifully updated en-suite bathrooms, while the primary suite includes a custom marble-top vanity and a thoughtfully designed built-in closet system. Every bathroom has been fully renovated with high-end finishes that elevate the home's overall design. Step outside to your own private outdoor retreat featuring a large covered patio with low-maintenance turf—perfect for entertaining, relaxing, or enjoying your morning coffee year-round. Major mechanical updates provide added peace of mind, including a 2023 air handler, 2024 water heater, all-new A/C ductwork, and added attic insulation for improved energy efficiency. With nearly every surface and major system thoughtfully updated, this exceptional Winter Park townhome offers luxurious, turnkey living in one of Central Florida's most sought-after neighborhoods.

1122 Washington Avenue Unit 7B, Winter Park
$695,000
O6420937 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