Winter Park Real Estate

Winter Park Real Estate

Located in Orange County, Florida, Winter Park is a charming city that offers a unique blend of natural beauty, cultural attractions, and a vibrant community. Known for its picturesque lakes, tree-lined streets, and historic architecture, Winter Park is a highly sought-after destination for both residents and visitors alike.

One of the main draws of Winter Park is its stunning chain of lakes, which provide endless opportunities for outdoor activities such as boating, fishing, and paddleboarding. Lake Virginia, Lake Osceola, and Lake Maitland are just a few of the many lakes that dot the city's landscape, offering breathtaking views and a tranquil atmosphere.

In addition to its natural beauty, Winter Park is home to a thriving arts and culture scene. The city is renowned for its prestigious Rollins College, which boasts a top-ranked liberal arts education and hosts various cultural events throughout the year. The Charles Hosmer Morse Museum of American Art is another notable attraction, housing the largest collection of Louis Comfort Tiffany's works, including his famous stained glass.

With its close proximity to downtown Orlando, Winter Park offers the perfect balance between a peaceful suburban lifestyle and easy access to urban amenities. The city's Park Avenue district is a popular shopping and dining destination, featuring a wide array of boutiques, restaurants, and cafes.

Whether you're looking for a serene place to call home or a delightful vacation spot, Winter Park's natural beauty, cultural attractions, and vibrant community make it an ideal choice.

Newest Listings in Winter Park

$649,000
2 Beds ⋅ 2.5 Baths ⋅ O6241728 MLS ⋅ 1120 BLDG.
Welcome to your new residence in Winter Park! This home is practically perfect with its oversized owner’s suite (with walk-in closet and jetted tub), guest room (split bedroom plan), bonus room/office/den/loft and breakfast bar on the upper floor. Indulgent bathrooms, Rinnai tankless water heater, tile and wood flooring (no carpet to replace in this one) upgrades everywhere! Granite countertops, wood kitchen cabinets with stainless appliances, range hood and a gas range top the list of creature comforts in you “culinary enthusiast’s” kitchen. The openness from the 9’ 4” ceilings and 8’ door continues to the outdoor space with French doors leading out to a screened and covered patio overlooking the beautiful backyard. This concrete block home also features a single car garage, concrete tile roof, and new turf backyard. The location is conveniently close distance to grocery stores, pharmacy, banks, restaurants, churches, and couldn’t be more convenient to Rollins College, Winter Park’s world-famous Park Avenue, Winter Park Village, and downtown Orlando, as well as I-4 or 17-92 for access to just about anywhere in Central Florida. NO HOMEOWNER ASSOCIATION/DUES!!

1120 Aragon Avenue, Winter Park
$160,000
2 Beds ⋅ 1 Baths ⋅ S5112332 MLS ⋅ D BLDG.
Investment and Lifestyle Opportunity in Winter Park! Discover the charm of Winter Park in this cozy and well-located condo! perfect for investors and buyers looking for a relaxed, safe, and convenient lifestyle. Spacious Condo 2 bedrooms with roomy closets, 1 large bathroom with double sink, bathtub, Ceramic tile and a new a/c unit, enjoy the confortable 881 square feet of living space with new Laminated floor throughout the property. Kitchen equipped with modern appliances with a dishwasher, microwave, refrigerator, oven, a pantry for extra storage, a new stackable washer & dryer is also included for your convenience. Living room with large windows and community views, first floor unit with a conveniente fenced terrace to enjoy the beautiful Florida weather, few steps from the community pool and recreational areas. Located in the heart of Winter Park, near Full Sail University, Rollins College and Wekiwa Springs State Park, in a quiet and safe area, this condo offers easy access to parks and is just minutes from renowned shops in winter park village, restaurants, hospital, great schools and profesional offices and much more places. The community offers a range of high-end amenities, including a community pool and bbq areas , fitness center and meeting room, 24/7 security and assigned parking recreational areas, playground and hiking trails, all designed to elevate your living experience. The strategic prime location next to I4 express and main roads and quality of the property ensure excellent profitability potential, being ideal for both owners who want to establish themselves in the area and for investors looking to generate passive income. Don't miss the opportunity to acquire this gem in Winter Park. This stunning home offers an ideal combination of tranquility and functionality, making it an attractive investment for those seeking quality of life in one of the most desirable areas of Florida. Schedule a private tour today! This condo is the perfect place to call Home Sweet Home or make a smart investment in a growing market!

1695 Lee Road Unit D113, Winter Park
$6,975,000
5 Beds ⋅ 7.5 Baths ⋅ O6240628 MLS
Distinctive. Inspirational. Timeless. Casa K is the ultimate in luxury and location. Designed by internationally respected architect, Kamal Rizk and constructed in 2022, it is a sanctuary in the heart of our city. The unique fusion of innovative design, superior craftsmanship & luxury finishes shaped this almost 9,000 SF, 5 bedroom, 7.5 bathroom residence w/ guest suite into the contemporary estate that it is today. Upon entry, the retreat-like elegance of the great room is remarkable. This commodious space incorporates the foyer, formal living, dining, bar & family rooms. It seamlessly opens to the outside via a Pella made “wall of sliding glass.” Italian wood flooring & elaborate millwork are appreciated features, as well as modern lighting, custom window treatments & sound operated w/ ease via Lutron. Beyond the family room is the kitchen & hidden scullery where livable luxury resides. Poliform cabinetry, Cambria countertops & top of the line appliances complete these exceptionally versatile spaces. The showcase glass enclosed floor to ceiling wine refrigeration anchors the kitchen & artfully displays up to 975 bottles. The outdoor living is a natural extension of the interior spaces & features a courtyard style pool complete w/ a hand carved, granite rear wall & 16’ linear in-pool fire feature. The kitchen terrace offers a DCS grill, motorized screens, cooling misters & more. A private office, lounge & 1.5 bathrooms complete the downstairs. Bathrooms on both levels showcase elevated selections from Boffi, Zucchetti, Poliform, Inbani, Paffoni & other iconic brands that enforce the refined, contemporary style & quality throughout. Notable lighting in the office, lounge & throughout include artistic fixtures by FLOS, Moooi, Serge Mouille & more. Access to the 2nd floor is provided via the elevator or stairwell. The upper floor is composed of the primary suite, 2 alternate bedroom suites, a 2nd office/flex room w/ en-suite bath, laundry room, gym & flex use guest apartment. The dreamy primary bedroom was designed with a soft entry, private terrace & hidden closets. The closets are part luxury boutique, part meticulously organized space w/ Poliform customization, motion activated light & windows w/ motorized shades made w/ UV protection to shield the interior spaces. The elegant approach to the primary bathroom includes floating vanities secured to stone covered walls, glass enclosed shower, standalone tub, custom-made dressing table & private water closets. Set apart from the primary, the alternate suites & living areas are finished w/ consistent quality & design. With flawless connection, the guest apartment may be used as an extension of the main home or it can be securely separated at a point just beyond the gym. The current owners use one of the bedroom suites as a craft room, which opens to the guest apartment’s main living spaces; the family room, a full kitchen w/ island seating, laundry & a final bedroom suite. Above is a magical roof top terrace with fireplace & bar. The owner’s entry is at the rear of the property, via a concealed driveway that leads to the 4-car garage, from which a hidden door opens directly into the kitchen. Guest parking is available. In this haven of opulent serenity, you may live the life you want, where you want.

654 W Morse Boulevard, Winter Park
$675,000
O6241478 MLS
Come build this one story dream home on this picturesque, spacious lot with breathtaking views in the heart of Winter Park. We have assembled a team of professionals to work with you to complete the interior and exterior design of this home. Not liking what you see? No problem! If you have a different style home in mind, we are prepared to build whatever you wish. With your vision and our experience, together, we will create a dream, resort style, pool, home overlooking the serene water. This opportunity allows you direct access to Lake Killarney making surfing, boating, and brunch at Hillstone a possibility. This rare canal front property, just under half an acre, is a perfect blend of city convenience on a private lake.

2139 Blossom Lane, Winter Park
$1,990,000
5 Beds ⋅ 4 Baths ⋅ O6241493 MLS
Pre-Construction. To be built. Here is the build you have been waiting for! This stunning one-story, 4-bedroom + office, 4-bathroom residence in Winter Park offers 3,174 sq ft of canal-front luxury. Maybe you have a different vision for your home? Set on an expansive 0.5-acre (Approximately) lot, you have the opportunity to create a custom masterpiece up to 6,000 sq ft. Our team of experts are ready to collaborate with you on designing both the interior and exterior to bring your vision to life. Imagine a resort-style retreat overlooking a serene canal, with direct access to private Lake Killarney for surfing, boating, and dining at Hillstone. This exceptional property blends urban convenience with the peacefulness of a private lake. Contact us today to schedule your appointment!

2139 Blossom Lane, Winter Park
$570,000
4 Beds ⋅ 3 Baths ⋅ O6241497 MLS
This Nicely updated home was completely Renovated in 2011 down to the studs to include New fixtures, drywall, flooring, electrical, plumbing, kitchen, cabinets, appliances, bathrooms, solid surface counters, roof, and front entry way/porch. The curb appeal is enhanced by a paver driveway, walkway and porch. More recent updates include New Dishwasher 9/2021, Septic Tank and Drain Field 06/2022, Water heater 02/2022, HVAC System 12/2017 and Luxury Vinyl Flooring 09/2020. This inviting home has 4 bedrooms, 3 full bathroom, 3 way split bedroom plan, offering plenty of open space for entertaining. The fenced backyard includes a large lanai, perfect for outdoor gatherings. Its Winter Park location provides convenient access to Winter Park Village, Downtown Orlando, and Major Highways.

1008 Dupont Avenue, Winter Park
$995,000
3 Beds ⋅ 2.5 Baths ⋅ O6240812 MLS ⋅ 1417.5 BLDG.
Pre-Construction. To be built. Enjoy a luxury, low maintenance lifestyle that you can just lock and leave! This brand new Transitional townhome from FG Schaub features three bedrooms and two and a half bathrooms with custom curated finishes within a functional open floor plan. When you approach the front door, you'll notice the spacious porch with tongue and groove ceilings. Entering the home, you'll be treated to extensive natural light, hardwood floors, 10’ ceilings, energy efficient LED lighting, 8' solid core doors and Level 4 drywall finish - no orange peel here!! The well appointed kitchen has a large island with seating, quartz countertops, tile backsplash, Thermador appliance package and custom cabinetry. As you ascend the staircase with solid wood treads and custom metal railing you'll discover the private owner’s retreat featuring a tray ceiling, crown molding, an en-suite bathroom with large walk-in shower and an oversized closet with custom built ins. On the opposite side of the second floor are 2 more spacious bedrooms with carpet flooring, a shared bathroom with dual sinks and a conveniently located laundry room. The exterior is designed to be easily maintained with a shingle and standing seam metal roof, custom board and batten shutters, and a 2 car garage with epoxy flooring and dedicated EV charger outlet. Energy efficiency items include: LED lighting, high performance, Low-E windows and block and stucco construction. Enjoy peace of mind with the 1 year builders warranty and the manufacturer's warranty on most major appliances. No HOA fees and just moments from Publix, Trader Joe’s, Park Avenue, Mills/50, the Science Center, Winter Park Events Center, Advent Health and a fantastic array of restaurants and coffee shops.

1417.5 Miller Avenue, Winter Park
$995,000
3 Beds ⋅ 2.5 Baths ⋅ O6240798 MLS ⋅ 1417 BLDG.
Pre-Construction. To be built. Enjoy a luxury, low maintenance lifestyle that you can just lock and leave! This brand new Transitional townhome from FG Schaub features three bedrooms and two and a half bathrooms with custom curated finishes within a functional open floor plan. When you approach the front door, you'll notice the spacious porch with tongue and groove ceilings. Entering the home, you'll be treated to extensive natural light, hardwood floors, 10’ ceilings, energy efficient LED lighting, 8' solid core doors and Level 4 drywall finish - no orange peel here!! The well appointed kitchen has a large island with seating, quartz countertops, tile backsplash, Thermador appliance package and custom cabinetry. As you ascend the staircase with solid wood treads and custom metal railing you'll discover the private owner’s retreat featuring a tray ceiling, crown molding, an en-suite bathroom with large walk-in shower and an oversized closet with custom built ins. On the opposite side of the second floor are 2 more spacious bedrooms with carpet flooring, a shared bathroom with dual sinks and a conveniently located laundry room. The exterior is designed to be easily maintained with a shingle and standing seam metal roof, custom board and batten shutters, and a 2 car garage with epoxy flooring and dedicated EV charger outlet. Energy efficiency items include: LED lighting, high performance, Low-E windows and block and stucco construction. Enjoy peace of mind with the 1 year builders warranty and the manufacturer's warranty on most major appliances. No HOA fees and just moments from Publix, Trader Joe’s, Park Avenue, Mills/50, the Science Center, Winter Park Events Center, Advent Health and a fantastic array of restaurants and coffee shops.

1417 Miller Avenue, Winter Park
$950,000
3 Beds ⋅ 2.5 Baths ⋅ O6238453 MLS
This stunning David Weekly home, built in 2017, perfectly captures the luxurious Winter Park lifestyle, just four blocks from the sophistication of Park Avenue and one block from the vibrant Winter Park Village. Stroll to renowned restaurants, boutique shops, and entertainment venues, all steps from your front door. Designed for the ultimate in hosting and entertaining, the open-concept living space is adorned with elegant finishes and designer touches, offering a seamless blend of style and comfort. The first floor boasts three generously sized bedrooms and two full baths, including a primary suite with a spa-like bathroom and spacious walk-in closet. Upstairs, the expansive living and dining areas invite effortless gatherings, with a gourmet kitchen featuring high-end stainless steel appliances, granite countertops, an island, and a natural gas cooktop—perfect for preparing gourmet meals while entertaining guests. Sliding glass doors open to a large balcony with new trek decking, ideal for alfresco dining or evening cocktails under the stars. The HOA provides complete lawn/shrub care, maintenance of the perimeter wall, and water for the irrigation system, ensuring your outdoor spaces are always pristine without the hassle. Built for both beauty and energy efficiency, the home includes double-pane low-E windows, R-38 insulation, and a tankless water heater..This move-in-ready masterpiece offers not just a home but an elevated lifestyle in one of Winter Park’s most sought-after locations. Schedule your private tour today!

439 N Capen Avenue, Winter Park
$1,798,000
4 Beds ⋅ 3.5 Baths ⋅ O6241123 MLS
**Stunning New Construction in Lake Killarney Shores** Welcome to your dream home in the highly sought-after Lake Killarney Shores! This exquisite 4-bedroom, 3.5-bathroom residence boasts a spacious 2,857 square feet of luxurious living space, complete with a charming casita featuring its own private bathroom. Enjoy the ultimate outdoor lifestyle with a refreshing saltwater pool, sun bench, and an outdoor kitchen perfect for entertaining. As you enter through the grand solid wood front door, you are greeted by luxury wood flooring in Captiva Maple and an abundance of natural light that fills the open-concept living areas. The home features 11-foot ceilings on the first floor, level 5 drywall, and 7.5-inch baseboards, creating an elegant and airy atmosphere. The gourmet kitchen is a chef's delight, showcasing a stunning marble backsplash, quartz countertops with a waterfall feature, and top-of-the-line Electrolux appliances, including a refrigerator, dishwasher, microwave, and a custom pot filler. A wine cooler adds a touch of sophistication, while the custom electric fireplace by Dimplex provides warmth and ambiance. Step outside to your private oasis, where a beautifully paved patio with seashell accents surrounds the saltwater pool. The summer kitchen is equipped with a gas grill, sink, refrigerator, and quartz countertops, making it ideal for alfresco dining. A privacy wall adorned with lush greenery ensures tranquility and seclusion from neighbors. Additional features include premium Pella windows with SunDefence for energy efficiency, a Dixie Pools tankless water heater, and two Daikin HVAC systems for optimal comfort. All door hardware is from Emtek and Richelieu, while stunning chandeliers and sconces from Light Style of Orlando and LBL Lighting add a touch of elegance throughout. With private lake access to Lake Killarney and proximity to Park Avenue's shopping and dining options, including Trader Joe's, this home offers the perfect blend of luxury and convenience. Don’t miss your chance to own this exceptional property—schedule your private tour today!

501 Country Club Drive, Winter Park
$1,650,000
4 Beds ⋅ 4 Baths ⋅ O6237059 MLS
One or more photo(s) has been virtually staged. Discover the perfect blend of elegance and functionality in this meticulously renovated single-story gem in one of the most sought-after neighborhoods in Winter Park. This chic transitional home, spanning 3,237 heated square feet, offers a seamless combination of contemporary design with a BRAND NEW ROOF, September ‘24. Inside, you'll find an open, airy layout with high-end finishes and smart touches throughout. The home features four spacious bedrooms, including two luxurious primary suites. The main suite boasts a spa-like bathroom with double vanities, striking granite countertop, an oversized frameless shower with dual shower heads, and a free-standing soaking tub. The second primary suite has a private entrance, washed brick accent wall, along with dual vanities and upgraded Kohler fixtures. At the heart of the home is a gourmet kitchen that’s truly a chef’s dream. It features a sleek granite island, European-style soft-close cabinetry, Jenn-Air appliances, including stainless steel gas cooktop with Zephyr hood and articulating pot filler, French door refrigerator, combo wall oven/microwave, and reverse osmosis system for purified water. Adjacent is the generous walk-in pantry with chrome shelving providing more than ample storage for all your culinary needs. Relax in the bright great room, where a soaring ceiling and stylish whitewashed brick wood burning fireplace creates a warm and welcoming ambiance. Sliding doors with electric shades seamlessly connect to an outdoor oasis featuring a paver patio, summer kitchen complete with a bar sink, built-in gas grill, hood, and refrigerator — perfect for al fresco dining and entertaining. Additional highlights include energy-efficient Vinyl Low E glass windows and doors, a Rennai tankless gas water heating system, programmable 15 SEER Carrier heat pump system, and security system. The indoor laundry room’s thoughtful design includes matching cabinetry, a Maytag washer, and matching gas dryer. The outdoor space features a wood-fenced yard for added privacy, and plenty of room for a pool. With no HOA and zoned for top-rated schools, this home is located within walking distance of Winter Park’s finest schools, Blue Jacket Park, East End Market, and more. Don’t wait to elevate your lifestyle with this stunning Winter Park property!

660 Arjay Way, Winter Park
$165,000
O6240801 MLS
LOCATION - LOCATION - LOCATION!!! The most coveted area of town has an EXCEPTIONAL BUSINESS OPPORTUNITY!!! An upscale - highly successful salon, known for its extraordinary customer service and top-notch beauty treatments is waiting for you. Ratings on Google and Yelp are solid 4.9 stars This turnkey operation has an established clientele. From Day One - you will be making money without having to invest in startup or development fees. Phenomenal walk-in traffic, especially going into the Winter season in the most coveted high end part of town - providing a village-like atmosphere, wonderful restaurants and a beautiful park in the center. The sale includes not only the good will, but also furniture, fixtures and equipment. The cost to build-out, furniture, fixtures and inventory was in excess of $50,000. The current owner is willing to remain and work part-time. The salon also has 5 stylists. Please call the listing agent to view this property. Additional services such as eyebrow threading, facials and make up can be added. It is fully operational which guarantees you income. This salon has a reputation of high volume clientele. Schedule your visit now. Do not miss this opportunity. Come and bring your offer right away. DOES NOT INCLUDE THE REAL ESTATE ***PLEASE do NOT approach any of the Employees or Clients of this Business. This Sale is Strictly Confidential.***

Winter Park
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