Homes for Sale in Winter Park

Welcome to this newly completed 4-bedroom, 3.5-bathroom home, located in the Lakemont Heights neighborhood of Winter Park. Spanning 2,843 square feet and built by the renowned Barefoot Brothers Construction, this home exemplifies the warm minimalistic style, blending modern elegance with a serene ambiance. With 10-foot ceilings throughout, spacious insulated casement windows, and wide plank engineered French oak flooring, the home offers a bright and open atmosphere bathed in natural light. The inviting covered front entry leads into an expansive interior, where the kitchen is a true showpiece. Custom millwork, floor-to-ceiling inset cabinets, and a premium Thermador appliance suite set the stage for both everyday meals and gourmet entertaining. The integrated butler’s pantry, complete with a wine cooler, microwave, and built-in shelving, adds even more luxury to the space. The open floor plan seamlessly connects the kitchen to the dining and living areas, which overlook the lush backyard oasis. Step outside to the large covered lanai, featuring a built-in summer kitchen and ample space for outdoor dining. A custom pool with a water feature is surrounded by tropical landscaping and an automated sprinkler system, creating a tranquil retreat perfect for both relaxation and entertainment. The first-floor primary suite is a luxurious escape, featuring sliding glass doors that open to the backyard and a spa-inspired bathroom with a zero-entry walk-in shower, double sinks, a makeup station with an LED mirror, and a custom walk-in closet. Upstairs, you’ll find a second master suite with its own ensuite bathroom, boasting double vanities and a standing shower. Two additional upstairs bedrooms share a Jack-and-Jill bathroom, with one offering a walk-in closet and an oversized fourth bedroom/flex space complete with a large walk-in storage room. This home is designed with both style and function in mind, offering built-in shelving in the upstairs hallway, a dedicated laundry room on the main floor, and smart home wiring with integrated in-ceiling speakers and stair lights. Two AC systems—one for each floor—keep the home comfortable year-round, while the tankless water heater, gas range, spray foam insulation, and an Aerobic treatment septic system add energy efficiency and environmental sustainability. Additional highlights include a spacious two-car garage with an epoxy floor finish, a feature wall with acoustic slat wood paneling, and a tropical landscape that provides privacy and tranquility. The property backs up to a protected, non-buildable area, offering a green sanctuary that enhances your sense of peace and seclusion. Located just a short walk from Phelps Park, the YMCA, and Lakemont Elementary, and only a quick drive from Winter Park’s top shops and restaurants, this Barefoot Brothers masterpiece presents a rare opportunity to own a thoughtfully designed, luxurious home in a prime location.

Lovely updated, pristinely maintained downtown Winter Park unit with pool and LAKE VIEW. This 2 bed 2 bath large unit offers 1267 square feet of living space. Enjoy your expansive views of the picturesque lawn, pool, and LAKE OCSEOLA. Your updated kitchen boasts beautiful upgraded granite, white solid wood cabinets, stainless steel Kitchen Aid appliances, instant hot water dispenser, Ferguson fixtures, and Casablanca fan. All the bathrooms have been updated as well with granite, glass doors, heater/exhaust fans, Ferguson fixtures and safety bars. The secondary bedroom includes a built-in queen size murphy bed for added functionality. The Bosch washer/dryer are located in the primary bedroom closet area. Add hurricane windows, Primus bump-proof locks, burglar bars, a covered parking space, a 2022 CARRIER AC system to the fact that unit can be purchased FURNISHED- including high-end, newer, furnishings make this a true move-in-ready property. The Cloister's is a well manicured and maintained community, located in downtown Winter Park. It offers a heated pool, putting green, fitness center, on site manager, clubhouse, not to mention private lake front park, dock and boat slips on the Winter Park chain of lakes. All this combined with your downtown Winter Park neighborhood. Two blocks from Park Avenue shops, restaurants, Art Festivals, concerts, farmers markets, and events equals the dream lifestyle.

**Investment Opportunity:** (TENANT IN PLACE. UNTIL MARCH 31, 2025. DO NOT DISTURBE THE TENANT!!!) Welcome to 618 Saint Johns Ct, Winter Park, FL 32792 – Attention All investor, this property offers a solid income potential. Winter Park's high demand for rentals, combined with the area's steady appreciation, ensures long-term value. Its proximity to local universities, shopping, and medical centers makes it highly attractive to renters, offering you an excellent opportunity to generate passive income. This charming 2-bed, 2-bath condo offering 1,037 sq. ft. of well-designed living space. Built in 1981, this home combines comfort with convenience in one of Central Florida’s most desirable locations. Situated in a peaceful community, the property boasts an open floor plan, spacious bedrooms, and ample natural light. Don't miss the chance to own or invest in this fantastic Winter Park condo! More photos coming soon.

Under contract-accepting backup offers. Welcome to 1851 Maywood Road, a beautiful 3 bedroom, 2 bathroom home located in the highly sought after city of Winter Park! With just under 1,500 SqFt of living area and almost a 1/3rd acre of land, this home features an additional LARGE PRIVATE OFFICE AREA, a NEWER HVAC SYSTEM (2023), and tons of renovations including a completely REMODELED KITCHEN (2022), NEW LUXURY VINYL PLANK FLOORING (2022), and RENOVATED BATHROOM! Let's walk through the home: as you walk through the front door, you'll notice the renovated kitchen with all modern updates, stainless steel appliances, and separate dining room space. The office space is split from the other three bedrooms and could continue to be used as an office, a den/bonus room, or even potentially converted to a FOURTH BEDROOM. After the passing the spacious living room, you'll reach the beautifully updated full bathroom with upgraded vanity, tile flooring, tiled shower, and barn door style linen closet. The three bedrooms further down the hall offer a generous amount of private living areas, with the primary bedroom additionally having its own full bathroom. As mentioned before, the yard is oversized - containing almost 1/3rd acre of land, huge backyard with mature landscaping, and 2 storage sheds (one of which with electricity). The location is amazingly convenient! You'll be in very close proximity to Historic Downtown Winter Park & Baldwin Park which offers some of Orlando's best restaurants, shopping, parks, dog parks, nature trails, museums! Fast access to highways / major roads to get around to other areas of Orlando as well. This home will not last long on the market! Call now to schedule your private showing today!

*MORE PICTURES TO COME* Welcome to your dream opportunity in Winter Park! This charming 3-bedroom, 2-bathroom home is nestled on a spacious, buildable lot, perfect for those looking to expand or create their ideal living space. The current residence features an inviting floor plan, filled with natural light and offering a cozy living area, a well-equipped kitchen, and comfortable bedrooms. The highlight of this property is the large lot, providing ample room for outdoor activities, gardening, or even the possibility of future development. The seller includes plans from a reputable local custom builder, allowing you to seamlessly design your dream home or add value with a new construction project. Situated in a treelined neighborhood, you'll enjoy easy access to Winter Park’s charming shops, restaurants, and outdoor recreation. Don’t miss this rare chance to invest in a property with both immediate comfort and exciting potential for the future!

Under contract-accepting backup offers. Welcome to this renovated traditional home, ideally situated on a corner lot in one of the most desirable neighborhoods in all of Central Florida. This charming, white-washed brick exterior Winter Park home offers everything a family could need. This two-story, 3 car garage, residence showcases the finest upgrades and provides an unparalleled living experience. As you enter the front door, the first floor welcomes you with a formal dining room that provides the perfect setting for entertaining guests with a custom-built wine display at arm's reach. Conversely, you also have an office that doubles as a sitting room with an exterior door leading to a charming cigar porch. As you continue down the hall, you enter an elegant living room featuring a gas fireplace, custom built-ins, and accordion stacking doors that open to a picturesque outdoor living area. The large chef's kitchen is equipped with a gas cooktop, farm sink, stainless appliances, quartz countertops, a butler's pantry, lots of cabinet storage, and a breakfast nook overlooking the pool. Opposite the kitchen, you have the first-floor primary bedroom with custom built-in closets and a large bathroom. Venture upstairs through one of the two staircases to an additional four bedrooms, three full bathrooms, and a bonus/theatre room, including two oversized storage closets that can be multifunctional. This is an excellent house for entertaining and enjoying the Florida sunshine with the expansive backyard, where you'll find a large pool, a covered sitting area, and a fully equipped summer kitchen with a grill, Green Egg, sink, and fridge. Located in the premier neighborhood of Winter Park, this home is minutes from Park Avenue, with numerous top restaurants, shops, and yearly events to enjoy. You can also easily access major roadways, top golf clubs, and tennis facilities such as the Winter Park Racquet Club and Interlachen Golf and Country Club. This home is zoned for highly rated Winter Park schools, including Dommerich Elementary, Maitland Middle, and Winter Park High School. This exquisite residence epitomizes elegant living in a prime location. Don't miss the opportunity to make this stunning home your own.

THIS GORGEOUS 2 BED/2.5BATHS MID-CENTURY MODERN ARCHITECTURALLY DESIGNED SINGLE FAMILY HOME IS NEWLY REMODELED AND NESSELED IN WINTER PARK COMMUNITY OF HIDDEN OAKS. THIS ELEGANT HOME FEATURES 1,031 SQ. FT. OF LIVING SPACE, A MODERN SWEDISH KITCHEN FEATURING CRYSTAL COUNTER TOPS WITH FUNCTIONAL DRAWERS, PORCELEN TILE FLOORS. STAINLESS STEELE APPLIANCES INCLUDE RANGE, RANGE HOOD, REFRIGIRATOR AND MICROWAVE/CONVECTION OVEN. BEAMED CIELING THAT FLOWS TO THE BEAUTIFUL LAMINANTE WOOD FLOORS. LOVELY DESIGNED MASTER AND QUEST BATHROOMS WITH STAINLESS STEELE FIXTURES AND WOOD LAMINATE CIELING FANS IN MASTER BEDROOM, LIVING ROOM AND FAMILY ROOM. BRAND NEW ROOF 2023, NEW 40 GALLON HOT WATER HEATER IN THE GARAGE. UPDATED PLUMBING, NEW ELECTRICAL PANEL AND UPDATED AC HANDLER, CONDENSER AND NEW AIR DUCTS. WONDERFULLY LANDSCAPED TO GIVE ULTIMATE CURB APPEAL. THIS HOME IS 10 MINUTES FROM DOWNTOWN ORLANDO, 15 MINUTES TO ORLANDO INTERNATIONAL AIRPORT, 10 MINUTES TO RETAIL SHOPPING AND RESTUARANTS, 15 MINUTES TO VALENCIAL STATE COLLEGE, 25 MINUTES TO UCF AND 30 MINUTES TO DISNEY WORLD.

***MOTIVATED SELLER***Come see this diamond in the rough located in the sought-after city of Winter Park! This home boasts a dining area, a separate family/lounge room, a spacious living room, which includes a fireplace as well as French doors that provides access to a covered patio and screened pool. Also it has 4 bedrooms, in which 2 are primary bedrooms, each with its own en-suite. There is also a bonus room that can be used as an office. Some TLC needed, but this home will be great for entertaining. Also, you have the benefit of accessing nearby amenities.

Great 1 bedroom condo located on the first floor! This cute condo offers newer kitchen cabinets and granite counter tops and a new dishwasher, new luxury vinyl flooring in the living and dining rooms, new tile flooring and cabinet in the bath and new carpet in the bedroom. The back porch is screened in and has a storage closet. The master bedroom has two closets plus a closet with hookups for a washer and dryer. The community is well maintained with a reasonable association fee. It offers 2 pools, a gym, laundry facilities and a clubhouse. The Strattford is located close to shopping and major highways. This is a great opportunity to have a mainteance free lifestyle at an affordable price!

Welcome home to Winter Park Woods! Charming 2 bed 2 bath condo! Open living and dining area. Updated kitchen features stunning stainless appliances and a breakfast bar. Master suite is complete with private bath and double closets. Additional bedroom is a great size and shares a hall bath. Back terrace a laundry room outside. Conveniently located near Full Sail, UCF, Valencia College and Downtown Orlando.

One or more photo(s) has been virtually staged. Welcome to Your Dream Home at The Enclave at Hawk's Crest! Discover this beautifully maintained 3-bedroom, 2.5-bathroom townhome in the sought-after gated community of The Enclave at Hawk's Crest. This move-in-ready home boasts an open floor plan with spacious living areas, perfect for modern living and entertainment. Upon entry, you are greeted by the stunning natural light filling the large living room, which flows seamlessly into the dining area and gourmet kitchen. The kitchen features granite countertops, stainless steel appliances, and a large center island, perfect for preparing meals or hosting friends and family. A half bath on the main level adds to the convenience of this floor plan. Upstairs, you’ll find a luxurious primary suite with tray ceilings, a spacious walk-in closet, and an ensuite bathroom featuring dual vanity, granite countertops, and a large walk-in shower. The other two bedrooms share a modern full bathroom. The bedrooms are ideal for an office, home gym, or playroom. Explore endless possibilities with your imagination. The home has thoughtful upgrades, including ceiling fans in all rooms, ample storage, and upgraded fixtures. Step outside to the screened-in lanai, perfect for morning coffee or relaxing in the evening while enjoying the privacy of your backyard. Additional features include a two-car garage and an upstairs laundry room with high-efficiency appliances. Residents enjoy access to resort-style amenities, including a sparkling community pool, fitness center, playground, and picnic area. The community also offers serene views of the lakes and ponds with walking trails, making staying active and connected with nature easy. This townhome offers the perfect combination of luxury, convenience, and community. Situated in a prime location near schools, shopping, dining, and major highways, this property won’t last long! Don't miss the opportunity to make this townhome your own!

Fixer upper! Priced to sell! Great investor opportunity. Property needs a little love and care. Another listing in the same community also vacant and available O6218059