Winter Park

Winter Park was the first centrally planned community in Florida; since its early beginnings as a 19th century resort destination, the city has always been a perfect place for both relaxation and recreation. With a number of wealthy and notable families residing in areas of Winter Park, this lovely city is generally considered to be one of the richest in Florida.

Located just northeast of Orlando, Winter Park is a place of parks, trails and lakes, of brick avenues, historic architecture and tree canopied streets. Nestled among the beautiful Winter Park Chain of Lakes (popular destinations for boating, fishing, and water-skiing enthusiasts), Winter Park is also known for its quaint shopping areas, its museums, and its popular festivals.

Winter Park's 30,000 residents are proud of their town's history, with several buildings over a century old. Few Central Florida communities can claim such a heritage. Community spirit is also evident in the variety of wonderful annual festivals, including the Bach Festival and the acclaimed Sidewalk Art Festival. Winter Park neighborhoods reflect this sense of community and history. The average price for a home here is $456,656 - this includes everything from sun-bleached haciendas in the $250K range, to exquisite Tudor style homes just under $1 million.

Winter Park Parks and Attractions

Parks, museums, bike trails, shopping - Winter Park has everything you could ever need, just minutes from home. Here we have just a small sampling of the attractions you'll find in the Winter Park area.

Winter Park Parks: Kraft Azalea Garden, Dinky Dock, Phelps Park, Howell Branch Preserve, Shady Park, Lake Island Park, Azalea Lane,Fleet Peeples Park, Cady Way

Winter Park Other Attractions: Park Avenue and many great restaurants.

Hot Winter Park Properties

3 Beds ⋅ 2 Baths ⋅ Four Seasons Condo SubDv. ⋅ 32792 Zip Code

One or more photo(s) has been virtually staged. I’m excited to share an incredible opportunity that you won’t want to miss—a spacious 3-bedroom, 2-bath condo in Winter Park at a fantastic price. Imagine closing on your new home before the Holidays! </p> This rare find comes with all appliances included, even the washer and dryer, making your move-in seamless. The community is packed with amenities, featuring three pools, tennis courts, laundry rooms, and a pet-friendly environment. Plus, the clubhouse has just been remodeled to include a brand-new fitness room for your convenience.</p> Four Seasons was designed with you in mind—blending traditional charm with a warm community feel that truly feels like home. Inside the condo, you’ll be impressed by the large rooms and thoughtful details such as remodeled Bathrooms, new windows and sliding door wall, an abundance of closets and even a outdoor storage closet. This quiet first-floor unit boasts great views and a spacious floor plan that invites comfort.</p> Located within the city limits of Winter Park often referred to as its best-kept secret—you’re just minutes away from downtown Orlando’s vibrant parks, entertainment options, fine dining experiences, and top-notch shopping. Educational institutions like Rollins College, Full Sail University, and UCF are also nearby.</p> Enjoy casual conversations with neighbors by the pool or simply relax in the serene environment of beautiful Winter Park. With a low HOA fee of only $430 covering water, trash removal, sewer services, pest control, building insurance and more—this is an opportunity you can’t afford to overlook.</p> Winter Park schools are highly regarded too: Brookshire Elementary School / Glenridge Middle School / Winter Park High School.</p> Let’s make your dream of owning this wonderful condo come true!

200 Saint Andrews Boulevard Unit 1402, Winter Park

3 Beds ⋅ 2 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Say hello to this Orwin Manor cutie! This unique bungalow is being offered fully furnished and is on an expansive lot, combining charm with convenience. Featuring three bedrooms, two baths and a spacious open floor plan, this adorable property welcomes you with sunlit living areas, gleaming hardwood floors and an inviting atmosphere that feels like home from the moment you step inside. The charming kitchen boasts new appliances, granite countertops and cabinets that beautifully complement the cottage-style aesthetic. The original hardwood floors enhance the home's warmth and character, flowing effortlessly from room to room. The dining area overlooks the sparkling pool, an ideal backdrop for entertaining. An additional living area, centered around a cozy fireplace, offers the ideal space to relax or host guests. Step outside to your private backyard oasis, providing endless opportunities for outdoor enjoyment and creativity. Ideally just minutes from renowned Park Avenue, with easy access to gourmet dining, boutique shopping, hospitals and Interstate 4, this enchanting property is a rare find with endless possibilities. Don’t miss your chance to make sweet Suffolk yours.

1331 Suffolk Road, Winter Park

3 Beds ⋅ 2 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code

The home is a tear down. City allows up to 4,071 sq feet that includes garage.

2837 Wright Avenue, Winter Park

2 Beds ⋅ 1.5 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code

PRIME LOCATION! Explore the ideal fusion of coziness and convenience in this modernized home, conveniently situated near esteemed educational institutions like Full Sail University, Barry Law School, Stratford, Keiser University, and UCF. Nestled within the coveted Winter Park community, this residence boasts freshly painted interiors, exuding a welcoming atmosphere. The chic kitchen showcases resilient granite countertops, a haven for culinary enthusiasts! With HOA covering water, sewer, and trash, enjoy hassle-free living. A brand-new roof installed in 2023 offers lasting peace of mind. Seize the opportunity to call this enchanting property yours. Arrange a viewing today and discover the unparalleled comfort and convenience of residing in one of Winter Park's most sought-after locales.

210 Scottsdale Square Unit 210, Winter Park

3 Beds ⋅ 2 Baths ⋅ Woodcrest Unit 5 SubDv. ⋅ 32792 Zip Code

Nestled in a tranquil cul-de-sac in the heart of Winter Park, this welcoming 3-bedroom, 2-bathroom home offers a serene lifestyle, enhanced by the absence of HOA fees. The expansive, fully fenced backyard, adorned with majestic mature oak trees, creates an idyllic setting for relaxation and entertaining. The open-concept layout features a bright living room that seamlessly connects to the dining area, ideal for family gatherings. The thoughtfully designed galley kitchen is equipped with stainless steel appliances and ample cabinetry for all your storage needs. The split-bedroom floor plan ensures privacy for the primary suite, which includes a large window that floods the room with natural light, a spacious walk-in closet, and an en-suite bathroom with a walk-in shower and seamless glass doors. An enclosed sunroom, featuring its own A/C unit and accessible through French doors from the dining area, provides additional living space perfect for enjoying serene views of the spacious backyard. The home also includes two additional bedrooms, a guest bathroom, a laundry room, and a 2-car garage with ample storage. Conveniently located near Howell Branch Road and just minutes from shopping, diverse dining options, and major freeways, this home offers the perfect blend of comfort and convenience for your lifestyle.

7420 Barnacle Court, Winter Park

2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code

This spacious 2-bedroom, 2-bathroom condo combines versatility and cozy comfort. The open floor plan is enhanced by soaring high ceilings and abundant natural light, creating a spacious and airy atmosphere throughout. Skylights brighten the living areas, making the space feel even more inviting. The kitchen features a separate bar and plenty of storage, seamlessly flowing into the dining and living areas—ideal for entertaining. A second-story loft offers a versatile space for a home office or hobby area. The fully enclosed back porch provides a private, year-round retreat. Additional features include ample storage, updated flooring, and a serene master suite. Perfectly situated in a peaceful community, this condo is the epitome of comfort and functional living. *PLEASE NOTE this home is being sold as-is*

2309 Sun Valley Circle, Winter Park

3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code

Discover luxury living in this exquisite single-story condominium, located on the second floor of the highly sought-after Douglas Grand. This elegant three-bedroom, three-bath residence seamlessly blends entertaining and everyday comfort, featuring an inviting open floor plan filled with natural light, beautiful crown molding and stunning French Oak hardwood flooring. The gourmet kitchen is a chef's dream, complete with a spacious breakfast bar island, custom wood cabinetry, granite countertops, and top-of-the-line Sub-Zero, Wolf and Bosch appliances, along with a generous walk-in pantry. The primary suite serves as a serene sanctuary, showcasing an indulgent soaking tub, dual vanities with granite surfaces, and two expansive walk-in closets. A second ensuite bedroom offers a private bath and generous walk-in closet. Additional features include a large utility room with new LG washer and dryer, updated light fixtures throughout, freshly painted interior, changing color hue can lighting, google smart carbon monoxide/fire detectors and nest thermostats and a new 81 gallon water heater (December, 2023). Enjoy the convenience and the unique advantage of a private entry to the unit from the secure, gated garage, with two reserved parking spaces. Situated in the heart of Winter Park, Douglas Grand grants easy access to Park Avenue, the Farmer's Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, the WP Tennis Center, and Winter Park Village. Embrace the effortless downtown lifestyle at Douglas Grand!

100 S Virginia Avenue Unit 201, Winter Park

3 Beds ⋅ 3.5 Baths ⋅ Mondrian/Winter Park Twnhms SubDv. ⋅ 32789 Zip Code

Introducing an exceptional opportunity at The Mondrian Winter Park, a stunning waterfront community featuring 30 contemporary townhomes elegantly situated along the serene shores of Lake Killarney. This remarkable residence is truly a standout, showcasing top-tier finishes that exemplify both quality and value. As you enter, you'll be greeted by fresh interior paint and updated flooring that enhance the home's modern appeal. Enjoy the added comfort of privacy shades, stylish light fixtures, and ceiling fans that enhance the overall ambiance. The chef-inspired kitchen is a culinary dream, equipped with a natural gas cooktop and a wine refrigerator, perfect for entertaining. Retreat to the luxurious master suite, which offers a walk-in glass shower, a separate water closet, and ample closet space for all your storage needs. Your own personal oasis awaits on the expansive rooftop terrace, complete with a hot tub spa, grilling station, and generous lounge area, ideal for hosting gatherings or relaxing under the stars. With soaring 10'6" ceilings on the second level and expansive storefront-style windows, natural light floods the living space, creating a bright and inviting atmosphere. Each of the three spacious bedrooms comes with its own bath, ensuring privacy and comfort for family members or guests. Nestled in the heart of beautiful Winter Park, just north of downtown Orlando, this luxury enclave offers an unparalleled lifestyle. Experience breathtaking views of Lake Killarney from the newly constructed dock or unwind in the lakeside Pavilion as you watch the sunset. For those who enjoy water activities, a private boat slip is available for purchase, allowing you to cruise across the lake to visit Trader Joe’s or enjoy a meal at Shake Shack. Outdoor enthusiasts will appreciate the community’s kayak and paddleboard racks, providing easy access for fishing, exercising, or simply soaking in the tranquil waters. Nearby, Winter Park Village boasts a variety of shopping and fine dining options, while the vibrant Farmer’s Market and renowned Enzian Theater offer an array of local culture and entertainment. Discover the ultimate blend of luxury, comfort, and convenience at The Mondrian Winter Park—where every detail is meticulously crafted for your enjoyment and every moment holds the potential for adventure. Welcome to your new home.

1818 Mondrian Circle, Winter Park

2 Beds ⋅ 1 Baths ⋅ Aloma SubDv. ⋅ 32792 Zip Code

Here is a great opportunity to build new or renovate/update current home in a quiet Winter Park neighborhood. Builder Potential! Lot Size is 60 front feet and 140 feet deep, lot expands outward to almost 77 feet in the rear of property. Great Location! This 1950s ranch, features 2 bedrooms and 1 bath facing Ward Memorial Park, a beautiful wooded park. Eat in kitchen, 1 car carport. This home is offered As Is. Winter Park area Schools! Numerous nearby cultural community amenities, Park Avenue, UCF Campus, Cady Way Trail, Winter Park Pines Golf Course and so much more. Winter Park’s finest dining is minutes away! Close access to major highways, minutes from downtown Winter Park, Advent Hospital & Orlando and UCF cultural and sporting events. Call today to see this property.

2151 Loch Lomond Drive, Winter Park

3 Beds ⋅ 2 Baths ⋅ Casa Aloma SubDv. ⋅ 32792 Zip Code

One or more photo(s) has been virtually staged. This beautiful Winter Park home boasts a split floor plan with three bedrooms, two baths, a Florida room and a den/office/flex space. Thoughtfully designed to offer sanctuary and spaciousness. This quaint and quiet neighborhood is a hidden gem. Step inside and be greeted by spacious, light-filled living and dining rooms, showcasing freshly painted walls and gorgeous wood laminate flooring that exude style and durability. Anchoring the home is a beautifully remodeled kitchen, complete with wood cabinets and stainless appliances. Natural gas is in the neighborhood and ideal for cooking on the gas stove. Water heater is also natural gas! Spanning over 2000 square feet, this residence welcomes you with an airy open floor plan that is flooded with natural light. In addition to three spacious bedrooms, this home also features a large Florida room and a bonus room/flex space, ideal for a home office, game room or home gym. Step outside to discover an expanded 16-by-40-foot screen-enclosed patio that allows you to entertain guests effortlessly and enjoy the Florida sunshine year-round, while overlooking the large fenced yard with attractive landscaping! Conveniently just minutes from Interlachen Country Club, Orlando International Airport, major roads, top-rated schools, shopping and dining. Enjoy the best of Winter Park in an affordable home where convenient living is guaranteed, allowing you to focus on enjoying the comforts of your dream home.

1332 Monte Lane, Winter Park

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