Homes for Sale in Winter Park

One or more photo(s) has been virtually staged. This is a diamond location home! New Construction built by the well respected Konkol Construction, located in the heart of beautiful Winter Park. 2024 Parade of Homes Winner, this home is warmly known as Biscayne Bay. This residence is a stunning 2-story Modern Farmhouse Style home that offers 3,652 sqft of total space, with 2,641 sqft under air. This 5-bedroom, 3-bathroom residence was built and designed with family-centric features, making it an ideal choice for those seeking both function and style. Inside, Biscayne Bay boasts luxurious finishes and thoughtful design elements. The interior features include Transitional style design, all hard surface flooring, white oak engineered hardwood floors, white oak stair treads, 1 x 6 baseboards, and four-panel interior shaker doors. The kitchen is equipped with white shaker style cabinets, quartz countertops throughout, and designer tile backsplash. The elegant primary suite boasts a stylish tray ceiling feature and a large custom walk in closet system. The gorgeous primary bathroom offers a soaking tub, large European sport shower with frameless doors, private water closet, and high-quality Kohler and Moen fixtures. The outdoor space is equally impressive, featuring a spacious rear porch, a generously sized backyard, professionally designed landscaping with a natural bamboo privacy wall, and an Optional pool plan that provides endless outdoor enjoyment. The exterior features sand smooth finished stucco with super acrylic paint, 30-year architectural shingles, and concrete paver driveway and walkways. Additional amenities include a 2-car garage with epoxy flooring, and Professional Wi-Fi with Cat 6 smart wiring. This home truly combines modern luxury with timeless farmhouse charm, making it a perfect in town retreat. This home is conveniently located just 5 minutes away from the popular Park Avenue, known for its upscale shopping, dining, and cultural attractions. The property is also within walking distance of Lake Killarney. For golf enthusiasts, Dubsdread Golf Course is only a 5-minute drive away. Plus this home's location provides easy access to I-4 and Orlando's world-famous theme parks, which are approximately 30 minutes away.

Experience Luxury and Charm! Discover an extraordinary residence nestled in the heart of Winter Park, where luxury meets location. This 2 bed / 2 bath (1,718 heated sq. ft.) is sure to charm you, spectacular wood parquet floors, Spanish/Mediterranean barrel roof tiles, inviting fireplaces, and walls of elegant French pane windows that flood the space with natural light. The impressive wood plank vaulted ceiling in the dining room adds a touch of European flair. The family room and dining room are adorned with floor-to-ceiling wood bookcases, adding to character and appeal. Tucked away for privacy: two charming patios overlook a secluded entryway, and meticulously re-paved brick paths wind through lush landscaping, ensuring utmost privacy and serenity. The expansive primary bedroom upstairs, offers views of Casa Feliz and the golf course. Plenty of space in large walk-in closet and its own cozy fireplace. Embrace the vibrant lifestyle of downtown Winter Park with a leisurely stroll to Park Avenue’s chic cafes, boutique shopping, and museums. The home is just steps away from the enchanting Charles H. Morse Park Moonlight Garden, known for its flower-covered archways and picturesque path leading to the historic Casa Feliz mansion. This property blends the best of both worlds: the privacy of a free-standing home and the convenience of condominium living. Recent high-end updates include a new water heater 2023, new electrical panel 2023, state-of-the-art Trane AC 2021, a stylishly remodeled kitchen with designer tile and stainless steel appliances, high-efficiency windows and doors, new tile roof 2021, and freshly painted exteriors. Trees have been trimmed and brick paths leveled as of May 2024. Only 6 distinctive units in this exclusive complex. All are unique with their own floorplans, personality, and charm. This home has two designated parking spots (1 covered parking) and offers unparalleled charm and sophistication. Maintenance-free lifestyle! Lock and leave for extended periods with no concerns. HOA handles maintenance and common areas. Don’t miss this rare opportunity—schedule your private tour today and make this Winter Park masterpiece yours!

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!

Welcome to your charming single-story ranch-style home nestled in a tranquil neighborhood. As you step through the front door, you're greeted by the spacious open floor plan seamlessly connecting the living room, dining area, and kitchen. Natural light floods the interior in the main living areas. Adjacent to the kitchen, the cozy family room invites you to unwind by the wood fireplace or gather with loved ones for movie nights. Sliding glass doors lead to the expansive backyard, featuring a sparkling pool perfect for hot summer days and a covered patio ideal for alfresco dining and entertaining. A principal suite and three additional bedrooms offer versatility for guests, home offices, or hobbies, while two more full bathrooms ensure convenience for everyone. Outside, the backyard with trees and a garden frames the pool area. With its desirable single-story layout, large outdoor space, and a corner lot, this ranch-style home offers a blend of comfort and functionality for today's lifestyle.

Located in the Tuscany Place neighborhood in the heart of Winter Park, this home offers endless potential for those looking to create their dream residence. With its classic ranch architecture and original features, this property is a blank canvas awaiting your personal touch, or provides a great opportunity to build new on its 0.39-acre corner lot. The home includes 3 bedrooms and 2 bathrooms, a formal living room, separate dining room, family room, sunporch, and kitchen with a breakfast nook. It also has a two-car rear entry garage. The spacious backyard provides room for outdoor gatherings and gardening, with mature landscaping. The location is excellent, within walking distance to Winter Park Racquet Club, and just moments from Winter Park and Maitland's vibrant dining, shopping, and cultural scene. Zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. This home is perfect for investors or homeowners seeking a project in a sought-after neighborhood. Being sold AS IS, please see Realtor Remarks for comments.

This light and bright, single-story, almost 3,000 square foot pool home features a split plan with four full bedrooms and three full baths. Your guests will immediately appreciate the expansive paver driveway, which allows easy, off-street parking. Once inside, they will admire the abundance of natural light provided by the new, large-format windows. Not only do the new windows (2022) illuminate the interior space, but they are also impact-resistant, energy-efficient, noise-reducing, and offer UV protection. The interior renovation was designed with minimal barriers between living areas, creating open, fluid spaces that enhance day-to-day living. The bedroom and bathroom layout is ideal, offering maximum privacy: two large bedrooms share one full bathroom on one side of the house, another bedroom with an en-suite bathroom (currently used as an office) is at the center, and the primary bedroom and bathroom are on the other side. Wood or natural stone flooring, extensive millwork, vaulted ceilings, new paint, updated lighting fixtures, and new fans enhance the spaces throughout. The kitchen was renovated to include an oversized, under-mount farmhouse sink, commercial-grade faucet, new LED lighting, and quartz countertops with a waterfall edge. The primary suite was updated by a former owner but was renovated by the current owner to add a second walk-in closet with custom organization. All bathrooms received light renovations, ranging from hardware and paint to new fixtures or vanities and countertops. In addition to the visually appealing renovations, the roof was replaced in 2019 and the house was re-plumbed in 2020. The outdoor improvements may be the most valued, as they created endless opportunities for outdoor living and entertaining on the newly constructed deck and enhanced landscape. All of the outdoor living benefits Florida provides are available here. A natural gas line was brought to the house as part of the renovation, allowing for easy future modifications such as a tankless gas-fueled water heater or gas-fueled outdoor grill. Located just one and a half miles from the notable retail stores and restaurants of Park Avenue and within a well-graded public school zone, there is nothing you won’t love about this home or its location.

Under contract-accepting backup offers. Welcome to this custom-built executive residence in Bear Gully Pointe, a prestigious gated community in Winter Park. This stunning pool home features a 3-way split plan that beautifully combines architectural details with stylish elegance, offering a spacious open-concept design that is both sophisticated and functional. Upon entering the foyer, your gaze is drawn to the sparkling pool and inviting outdoor entertainment area. The lovely living and dining rooms provide an ideal setting for formal entertaining. A very generous kitchen size, which boasts ample counter space, a walk-in pantry, a breakfast bar, rich granite countertops, and a private butler’s pantry with a sink and great storage, is a wonderful gathering space for lots of friends and family. It flows seamlessly into the eat-in area and family room, both of which offer picturesque views of the pool. The oversized primary bedroom suite is a true retreat, featuring a cozy sitting area with pool views and a recently updated bathroom that includes dual sinks, granite countertops, a soaking tub, a large walk-in shower, and a generous walk-in closet. The main floor also offers a home office, two additional bedrooms, an updated bath, and a spacious laundry room. Upstairs, you will find a sizable bonus room, a fourth bedroom, and an updated fourth bath. Set on nearly a half-acre cul-de-sac lot, the property showcases lush tropical landscaping. The screened lanai overlooking the pool and spa provides a welcoming space for entertaining and relaxation, perfect for enjoying the Florida lifestyle, complete with a splash pad for hours of enjoyment for the little ones. Recent improvements include a new roof (2020), exterior paint, new garage doors (2024), and recent replumbing (2024). The property also features a three-car side-entry garage. Residents of Bear Gully Pointe enjoy amenities such as a tennis court, children's park, and sidewalks. Located in Seminole County, this home is conveniently close to Winter Park’s amenities, top-rated schools, Trinity Prep, and major highways, providing easy access to downtown Orlando, the airport, theme parks, and Florida’s beautiful beaches. This property epitomizes luxurious Florida living, blending style, functionality, and a coveted location to create an exceptional living experience. Call today for your private viewing of this remarkable home.

Welcome to this stunning 4-bedroom, 2.5-bathroom POOL home with a NEW ROOF, offering a perfect blend of modern luxury and functionality, located in the desirable Sylvan Lake Shores neighborhood of Winter Park. The property boasts a thoughtfully designed open floor plan with dark oak wood floors and recessed lighting throughout, creating a bright and inviting atmosphere. The gourmet kitchen is a standout feature, equipped with a gas stainless steel range, pot filler, stainless steel hood, quartz countertops, a farmhouse-style sink, and a large island with seating—perfect for casual dining or entertaining guests. French doors open from the kitchen and living areas to a covered, paver lanai, where you’ll find an outdoor summer kitchen complete with a fridge, gas cooktop, grill with rotisserie feature, and vented hood. The outdoor living space also includes a TV, offering the ideal setup for year-round entertaining. Step into your private backyard oasis, fully fenced and surrounded by lush vegetation, a waterfall, and a water feature. The paver, heated pool provides a relaxing escape, while the expansive lanai runs the width of the home and features seating, dining, and lounge areas. Whether hosting a poolside gathering or enjoying a quiet evening, this backyard offers unparalleled privacy and tranquility. The home’s split floor plan ensures privacy for all, with the primary bedroom and two secondary bedrooms featuring French doors that open to their own private retreats. The primary suite has been fully remodeled and includes a spacious walk-in closet with built-ins and a safe, as well as private access to the pool deck. The luxurious en-suite bathroom boasts a dual-sink vanity, a throne room, and a large shower with a wand feature, creating a spa-like experience. Additional features include a Nest thermostat, Ring security system, a laundry room with a utility sink, and a 2-car garage. The office, which can be used as a fourth bedroom, offers built-in cabinets, shelves, and a closet, providing ample storage. The home also comes with a gas hot water heater and a new metal roof, ensuring energy efficiency and durability. Located just minutes from Winter Park's vibrant shopping, dining, and top-rated schools, this home offers a rare opportunity to enjoy modern living in one of Central Florida’s most sought-after areas. Schedule your private showing today and discover the perfect blend of comfort, luxury, and outdoor living!

This Winter Park investment opportunity is prime for Developers, Builders, & Investors for redevelopment. The Hawick Lane property currently has a single family house that is Tenant-Occupied and income producing. It is believed that the highest and best use of this property would be to tear down the current house and redevelop the property into four (4) detached single family homes in a courtyard style development or a lot split into three (3) fee simple single family lots (50’ wide). The total land area is approximately 19,698sf. (150ft street frontage by 140ft lot depth).

Discover the charm and downtown Winter Park ambiance with this two-bedroom plus office, two-bath Mediterranean villa, a true “hidden gem” out of the way to find off Interlachen Avenue! The quaint six-villa condominium community is adjacent to the historic Winter Park Golf Course & Casa Feliz. Just footsteps from the vibrant shopping and dining on Park Avenue, this peaceful, private retreat is a European style sanctuary right in the heart of downtown Winter Park. This 1,610-square-foot, two-level condominium is a unique find and wonderful opportunity to make it your own private oasis. On the main level there is a lovely kitchen open to dining room and gorgeous living area featuring vaulted wood ceilings, a wood-burning fireplace, and two walls of French doors opening to separate private courtyards, covered lanai and fountain... There is also a secondary bedroom suite that includes an ensuite bath, perfect for guests or family. Lastly, there is a secluded office/sunroom with gorgeous arched windows and a separate entrance that offers a versatile space for work or relaxation. Upstairs solely encompasses the spacious primary suite boasting a sitting area, French doors and windows and two balconies including an expansive covered balcony off the bedroom, a walk-in closet, and ensuite bath. Embrace the old-world feel of the Spanish/Mediterranean architecture, complete with a newer community tile roof, recent new exterior paint, and peaceful winding courtyards. A secretive brick drive leads to the unit's two designated parking spots including one in a covered carport. Enjoy the Lock and Leave lifestyle with the enjoyment of downtown living and the seclusion of this Winter Park treasure. Walk to the Winter Park Golf Course, Casa Feliz, and stroll through the iconic streets of downtown Winter Park. Don’t miss this incredible opportunity to own a piece of Winter Park's history.

*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!

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.