Homes for Sale in Winter Park

Under contract-accepting backup offers. Welcome to this professionally renovated Winter Park home with lots of attention to detail. Featuring a stunning custom kitchen, spacious island, ample cabinetry, quartz countertops, stainless steel appliances & custom breakfast nook, great for casual dining and gatherings. An open-concept living area that seamlessly flows from the family room & living room, to the expansive kitchen, creating an inviting atmosphere for relaxing and entertaining. Split plan with 4 Bedrooms and 2 Bathrooms. The Primary Bedroom has an updated ensuite bathroom with dual sinks and lighted & fog free mirror. Beautiful versatile Florida room that can serve as a playroom, game room, home office or where ever your imagination takes you. Outside enjoy the privacy of a fully fenced backyard with a beautiful deck. Additional updates include a new roof, all new flooring, interior and exterior paint, electric panel & new fixtures, ewer double pane windows, water heater and more. Great neighborhood, excellent Seminole county schools, walking distance to Eastbrook Elementary. Prime location, close to ample shoping, dining, UCF, Park Avenu and Orlando International Airport. Move in Ready

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!

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.

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.

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.

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.

Winter Park schools are highly regarded too: Brookshire Elementary School / Glenridge Middle School / Winter Park High School.

Let’s make your dream of owning this wonderful condo come true!

In a tranquil cul-de-sac in the heart of Winter Park, this welcoming three-bedroom, two-bath 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 bath with a walk-in shower and seamless glass doors. An enclosed sunroom, featuring its air-conditioning unit and accessible through French doors from the dining area, provides additional living space for enjoying serene views of the spacious backyard. The home also includes two additional bedrooms, a guest bath, a laundry room and a two-car garage with ample storage. Conveniently near Howell Branch Road and just minutes from shopping, diverse dining options and major freeways, this home offers the ideal blend of comfort and convenience for your lifestyle.

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.

Under contract-accepting backup offers. 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.

This spacious 2-bedroom, 2-bathroom condo in Cedarwood Village 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.

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.

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!

Remarkable Winter Park condo looking for new owner. Great opportunity 1st floor, overlooking pond, Includes covered carport and assigned open parking space. Totally renovated. 2 Bed 2 bath, inside laundry room. Don’t miss this beautiful condo. Kitchen counters redone 2023 with granite, real wood shaker cabinets, stainless steel stove and dishwasher. Main bath has been remodeled, granite vanity, redone shower with new shower pan, ceramic tile floors and glass barn door enclosure, new toilet. French Doors to lani and pond views. Second bath also redone with extra deep soaker tub, new tiled walls with decorative border and granite vanity, ceramic tile floor. AC just replaced 6/2024, 40 gal water heater. Crown molding throughout and all new ceilings fans. (KI, Living Rm, both bedrooms and patio) Charming screened patio with ceramic tile overlooking pond and storage closet. This is a delightful community with mature trees, pool, tennis court, clubhouse and inside bike storage room. Centrally located community in Winter Park near Full Sail, Cady Way Trail, Showalter Field, Ward Park, Winter Park Hospital, Wellness Center & YMCA. Walk to grocery or a short drive to Park Ave shopping and restaurants.

Under contract-accepting backup offers. 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.

Under contract-accepting backup offers. Turnkey 2 bedroom/2 bathroom condo unit! This would be great for a first home, for a Full Sail student, or as an investment unit! It offers an open living area with tile flooring throughout, with a split bedroom layout, and freshly cleaned carpets in the bedrooms. The hall bath was just remodeled- new tub, vanity, countertop, and sink. The living room opens up to a screened-in patio with a fenced in back yard. There are 2 assigned parking spaces, and a community pool! For investors- Rents for a 2/2 in the community are approximately $1500-1600/month! This unit is priced to sell, schedule your viewing today!

Welcome to the luxury of Winter Park condo living, just steps from the world famous Park Avenue! You will be delighted to step into elegance in this charming first-floor condo with 9' ceilings in the highly sought-after Villages of Winterset Condominiums. Picture this – a simple stroll from your doorstep leads you to Park Avenue's enticing shopping and dining delights, the Morse Museum's cultural treasures, the vibrant energy of Rollins College, the refreshing greenery of the Winter Park Golf course, and the convenience of Sun Rail's commuter train. Immerse yourself in the charm of Central Park, where art festivals, concerts, movies, and events unfold right before your eyes. The Winterset mid-rise building offers key-secured access and a convenient call box for welcoming visitors. The lobby extends a warm welcome with a lounge area, perfect for unwinding or greeting your guests. Indulge in the pristine amenities of this well maintained community – a generously sized private pool, sun deck, and a grilling area designed for your leisure. Now, let's talk about this freshly painted gem of a corner unit – bathed in natural light and adorned with stunning travertine floors. The fully remodeled kitchen (2024) features granite countertops, new cabinets, all new stainless steel appliances and overlooks the spacious dining space. The open-concept dining into living room leads you to the open-entry sunroom that features energy-efficient impact-resistant sliding glass doors that overlooks a paved patio and lush greenery. Both of the bedrooms feature brand new carpet and beautiful plantation shutters that offer privacy and energy efficiency. The welcoming primary suite, boasts a walk-in closet and elegant make-up vanity with a large walk-in tile shower, big enough for two! The guest bath exudes charm with warm wood cabinetry and a tub/shower combo. Live the carefree lifestyle you've been dreaming of in this exclusive Winter Park haven, surrounded by multi-million dollar condos and homes. A property like this will not be available long. Call for your private showing today!