Homes for Sale in Winter Park

Nestled in Winter Park one of Orlando most sought-after neighborhoods, this exceptional 3-year-old home offers 5 spacious bedrooms and 4.5 beautifully appointed bathrooms, combining modern luxury with family-friendly functionality. With thoughtful design, high-end finishes, and an open-concept layout, this home is perfect for both comfortable living and elegant entertaining. As you step inside, you'll be welcomed by soaring ceilings, sleek hardwood floors, and abundant natural light throughout the expansive living areas. The gourmet kitchen is a chef’s dream, featuring top-of-the-line appliances, a large quartz central island, custom cabinetry, and a walk-in pantry. Whether hosting a dinner party or preparing family meals, this kitchen is equipped for it all. The primary suite is a true retreat, offering a generous walk-in closet and a spa-like en suite bath complete with a soaking tub, separate glass shower, dual vanities, and exquisite finishes. Each of the additional four bedrooms is spacious, with ample closet space and access to beautifully designed bathrooms, ensuring comfort and privacy for everyone. Upstairs features a large retreat surrounded by 2 of the bedrooms and 2 full baths. For those who love to entertain, the open living and dining spaces flow seamlessly to the backyard, where you can enjoy Florida's beautiful weather. The home is equipped with high-end fixtures and modern conveniences, from smart home technology to energy-efficient features. Located in the heart of Winter Park, known for its tree-lined streets, excellent schools, and vibrant dining and shopping scene, this home is just minutes from everything the area has to offer.

Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando.

Stunning residence in Winter Park! Experience luxury and convenience in this highly sought-after location, so close to everything, you can walk to Winter Park Village (.5 miles), Hannibal Square (.3 miles) and Park Avenue (.6 miles), and less than a block to the beautiful Lake Island Park. You will be the envy of all who visit. This home features a gourmet kitchen with waterfall island undermount farm sink and top-of-the-line GE Cafe' appliances. The generous open floor plan, soaring ceilings, and custom wood-tread stairway with iron spindles create a grand experience as you enter the home. Your master suite is set on the main level, offering seclusion from the upstairs bedrooms. The open living area seamlessly connects to your outdoor living space, making it perfect for entertaining. You'll love the custom bar area, complete with a wine refrigerator. As you arrive, you'll be greeted by the grand elegance of the architecture, beautiful landscaping, and a 1 1/2 car garage. Don't miss your chance to own this premier home in Winter Park!

Welcome home to this beautiful home located in the highly desirable Timberlane Shores. Situated on almost 1/3 of an acre, this corner lot home has endless possibilities. The 4- bedroom, 3.5 bath home has over 2700 sq feet of living space, including separate guest quarters that consist of 2 bedrooms and 1 shared bath, perfect for extended family, teens, or simply to have privacy for guests. As you enter the home, you will notice the large open concept that includes both dining and living space. The gourmet kitchen features white quartz countertops, 42-inch espresso cabinets, stainless steel appliances, and a large island that can accommodate 3 barstools. The master bedroom has an ensuite bath with a large walk-in shower, marble tile and textured subway tile in a tub/shower combo. The secondary bedroom in the main part of the home functions as a second master bedroom and also has an ensuite bathroom. A very private and serene patio area from which to watch the birds and hear tranquil sounds of nature, can be found through the living room sliders. The home’s 2-car garage is spacious and offers a tremendous amount of storage. This unique home is surrounded by multi-million-dollar homes, so there is also the opportunity to tear this down and build a brand-new home on the lot. Close to downtown and Winter Park Village and Park Avenue is less than 2 miles away. Beautiful parks, walking/bike trail and dog park are within walking distance. You don’t want to miss this one!

One or more photo(s) has been virtually staged. Nestled within the charming enclave of Winter Park, this captivating residence transcends the ordinary, offering an unparalleled living experience that seamlessly blends contemporary luxury with thoughtful design. From the moment you step into the spacious office space, it becomes evident that every aspect of this home has been meticulously crafted to cater to both productivity and relaxation. At the heart of the home lies the gourmet kitchen, a culinary enthusiast's dream come true. Boasting top-tier appliances, abundant quartz countertops, and a generously sized central island, it effortlessly marries style with functionality, setting the stage for culinary adventures and delightful gatherings alike. The seamless flow from the kitchen into the dining and living areas ensures that every shared moment becomes a cherished memory. Here, the ambiance of the space enhances the joy of connection and celebration, creating an inviting atmosphere where laughter and conversation abound. Step outside into the outdoor oasis, where a serene lanai awaits, beckoning you to indulge in moments of tranquility and outdoor entertainment, complete with a summer kitchen and a sparkling pool. Picture yourself hosting gatherings or enjoying al fresco dining, as the lush surroundings elevate your lifestyle to new heights. The four bedrooms have been thoughtfully designed with comfort and privacy in mind, offering ample closet space and large windows that bathe the rooms in natural light, including a complete guest suite on the main floor. Each floor has its own laundry (two washers and two dryers included!) as well as one AC unit per floor, maximizing comfort, practicality and energy efficiency. Situated in the heart of Winter Park, this home offers convenient access to an array of amenities, including top-rated schools, shopping centers, dining, and recreational facilities. Here, the location isn't just a backdrop but an integral part of the lifestyle. Custom-built in 2024 to perfection, this gem seamlessly combines modern living with timeless design, making it an exceptional residence for those who seek the perfect fusion of elegance and functionality. Don't miss the chance to turn this dream home into your own reality —schedule a private tour today and step into the lifestyle you've been envisioning. Your ideal home awaits!

HOLIDAY SPECIAL: Seller to pay up to $20,000 towards buyer's closing costs! ENTIRE INTERIOR HAS BEEN FRESHLY PAINTED!! Discover the epitome of Winter Park living in this exceptional Douglas Grand brownstone, ideally located between Park Avenue and Hannibal Square! This remarkable residence features a private two-car garage within the secure Douglas Grand parking facility and boasts a personal street-side entrance, providing easy access to a plethora of shops, restaurants, and the SunRail station. Meticulously renovated in 2020, this townhome offers a stunning, spacious kitchen with an island, in-wall speakers, and sleek wood floors upstairs complemented by elegant new tile downstairs. High ceilings and ambient lighting enhance the open and inviting atmosphere. The luxurious master suite features two walk-in closets, dual vanities, a walk-in shower with double shower heads and body spray, a garden bathtub with smart TV connections, and a linen closet. The second bedroom offers a private bathroom and walk-in closet, while the third bedroom is generously sized with a walk-in closet. All bedrooms are equipped with Cat5 cable for seamless streaming, and the second floor includes a laundry room with ample storage. A new water heater adds to the home's convenience and comfort. High-end finishes throughout include Pella windows and doors, Kohler® fixtures, Sub-Zero, Wolf, and Bosch appliances, quartz countertops, surround sound speakers, and dual AC units. Recent updates feature new light fixtures, wired in-wall speakers, and WiFi-enabled thermostats, ensuring a modern living experience. The Douglas Grand community combines the charm of historical architecture with contemporary amenities. Centrally located in Downtown Winter Park, it provides easy access to the SunRail station, Winter Park Farmers Market, and numerous local attractions. Schedule your private showing today. Property may be under audio and visual surveillance.

Discover an exceptional opportunity with this one-of-a-kind townhome that includes a private boat slip! Nestled in the picturesque Winter Park, Florida, this brand-new home boasts breathtaking views of Lake Killarney and offers a perfect blend of luxury and comfort. With 3 bedrooms and 3.5 baths spread across over 2,300 sq ft, you'll be greeted by a grand 17-foot foyer that leads into an expansive great room featuring soaring 11-foot ceilings. The floor-to-ceiling windows flood the space with natural light while framing stunning lake and nature views, creating an inviting atmosphere perfect for both entertaining and everyday living. The gourmet kitchen is a chef's dream, equipped with top-of-the-line Wolf and Subzero appliances, elegant double-stacked soft-close cabinetry, and designer lighting. Enjoy the convenience of a spacious walk-in pantry and motorized window shades. Step outside to the unique rear lanai, where you can savor serene lake vistas or stroll along the community sidewalk that encircles the property. Retreat to the luxurious second-level primary suite, thoughtfully positioned for tranquility. It features expansive storefront-style windows, dual walk-in closets, and a spa-inspired bath adorned with designer-selected tiles, a dual sink vanity, a frameless glass shower, and a private water closet. The versatile bonus loft area is perfect for a home office or a cozy reading nook, while the adjacent outdoor balcony with a cocktail kitchen offers unparalleled views of the lake. Two additional bedrooms, one with an en suite bath, ensure comfort and privacy for family or guests, complemented by a conveniently located laundry room that separates the primary suite from the secondary bedrooms. This townhome exemplifies modern living, complete with a desirable two-car garage featuring an epoxy-painted floor, an EV charging plug, and ample storage. Experience the pinnacle of elegance and comfort in this prime Central Florida location—your dream home awaits!

Discover the ideal space to grow and elevate your business with this prime C1-zoned property, perfectly situated on a bustling main street with high foot traffic and endless possibilities! This versatile LIVE/WORK property is perfect for an owner/operator seeking a seamless integration of business and personal life. Located in the vibrant Winter Park area of Orlando, your business will benefit from exceptional visibility, ample parking, and easy access to major transportation routes. Whether you envision a fitness studio, bridal gallery, photography studio, custom tailoring shop, legal or consulting practice, aesthetic services, or a pet grooming or daycare facility, medical office, dispensary, highest retail, real estate office, pawnshop, this space is ready to bring your vision to life with endless possibilities. In addition to the commercial potential, enjoy the luxury of a spacious 3-bedroom + den, 4.5-bath residence with a private grand entrance, a gourmet kitchen, and a private salt water pool. The flexibility of the property allows you to live on-site while keeping your business separate, just like the current owners operate from their office with a separate entrance, or to convert the entire building to suit your business needs. The expansive layout also offers easy opportunities for expansion, making this an excellent investment for future growth. A standout feature is the prominent plaza sign included with the sale, saving you thousands in signage costs. Plus, the property is not located in a flood zone, offering peace of mind for your investment. Your next business success story starts here, just minutes from downtown Orlando, with the privacy of your own backyard oasis. The possibilities are endless—don’t miss out on this incredible opportunity!

Luxury is a lifestyle, and this Winter Park modern bungalow on a cobblestone street, is full of natural light, clean lines and crisp open spaces. With three bedrooms and 2.5 baths in the main house, this home has been thoughtfully renovated with style and is a home that beckons the green of the outdoor lifestyle. Over 2,400 square feet in main house and the garage was converted to an additional dwelling unit, adding ADDITIONAL 400 sf or so, current use is a studio, can easily transform to a guest house, mother-in-law suite or back to a garage, whatever function fits your needs. Front motorcourt can accomidate lots of vehicles, easy in and out and includes electric car charging station. The kitchen is open to the gathering room with spacious volume ceilings. Home was recently renovated with stainless appliances, including a Thermador gas range, clean-line cabinets with glass door accents, Cambria Gold quartz countertops, counter seating, a farmhouse sink and gorgeous window to the outside. Main living space is anchored by warm wood floors, with marble floors in bedrooms, all generous in size, with fresh light walls and an extensive lighting package throughout. All baths are updated with marble-influenced accents and gold finishes. Primary suite enjoys sleek authentic Carrera marble seamlessly throughout with walk-in closet for great organization. A luxurious bath retreat showcases a soaking tub, dual sinks and a chic open shower with a frosted window. The natural light in this home adds to the beauty in all spaces. Glass slider doors invite you to the outdoor oasis with an expansive covered pergola, cover is waterproof with the Herculas roof system. Lush greenery and mature landscape and majestic oaks round out the space and topped off with an upscale bar for making entertainment simple. This home was extensively renovated including roof and gutters, re-pipe, newer air conditioners, electrical panels, gas tankless water heater, parking motor court, professional landscape and landscape lighting, the additional separate studio recently updated, paved courtyard, bistro lighting and more. Location is paramount near Winter Park Racquet Club, terrific schools, zoned for Winter Park High, close to Park Avenue, fantastic shopping and restaurants. A great investment opportunity to live among the finest homes in Winter Park and in well well-established neighborhood providing a lifestyle like no other.

Priced below appraisal! Highly desirable Lugano Terrace, 4-bedroom, 3.5-bath brick home offering timeless charm and modern amenities just steps from the serene shores of Lake Knowles. Set amidst lush, mature landscaping, providing excellent value in this sought-after location. Inside, you'll be greeted by real hardwood floors that flow throughout the main living areas, complementing the vaulted ceilings and spacious, open design. The inviting living room features a cozy wood-burning fireplace, while the formal dining room offers a peaceful view of the pool and backyard. The open kitchen is a chef's dream, with sleek granite countertops, white cabinetry, and an eat-in island that opens to the family room, which is anchored by a gas fireplace. Additional pantry space in a second pantry adds convenience for storage and organization. The expansive upstairs, primary suite is a true retreat, offering generous space for a sitting area and a stunning, spa-like bath with a dual-entry shower, standalone soaking tub, dual vanities, and ample storage. A light-filled office, a library/conservatory, and a loft added in 1993 provide flexible living spaces. Three nicely sized bedrooms are located downstairs, offering privacy and convenience for family or guests. The outdoor space is equally impressive, with a private backyard that includes a sparkling pool, a grassy area perfect for play, and a lovely porch ideal for entertaining or simply enjoying the tranquil surroundings. The home also features a roundabout in the front for easy access and abundant parking, along with a 2-car garage that includes a workshop for added functionality. Additional updates include a new roof (2021). Located just minutes from Winter Park’s iconic Park Avenue, the Winter Park Racquet Club, and within walking distance to top-rated schools—Dommerich Elementary, Maitland Middle, and Winter Park High. With its blend of classic design and modern updates, this home is an unforgettable opportunity in one of Winter Park's most coveted neighborhoods.

Walk to Park Avenue or take your boat on a sunset cruise through the canals! Experience upscale living in this fabulous condo with a DEEDED boat slip on the famous Winter Park Chain of Lakes. Located on the fifth floor, you will enjoy breathtaking tree-top lake views from this beautifully updated, one story unit covering almost 2100 square feet. The open layout features expansive living and dining areas that seamlessly transition to an outdoor screened-in porch. The stylish kitchen is well equipped with custom wood cabinets, granite countertops, stainless steel appliances and a center island with breakfast bar. The condo features a spacious guest suite with double closets, and a dramatic guest bath, complete with a custom designer vanity and a large walk-in shower. The generous owners suite offers a lounging area with radiant natural lighting. The spa-like bathroom includes custom vanities, soaking tub and a large walk in closet with built-ins. Additionally, features include automated blinds in the living room and an indoor laundry closet. The well maintained complex located on the shores of Lake Osceola offers underground parking, storage closet, and amenities such as pool and community laundry room. The property includes a deeded boat slip. Situated just steps away from vibrant Park Ave, residents will enjoy many fantastic restaurants, cafes, Museums, and Boat Tours, in addition to the convenience of the Sunrail/Amtrak station. The condo fee includes electricity, sewer, water, gas, maintenance, on-site manager, community pool, ground maintenance, roof, insurance, exterior and more.

Stunning, custom-built home in the Winter Park Tree Streets. This beautifully designed, Mediterranean-style home features 4 bedrooms, 3 full-baths, and an open layout complimented by engineered wood and travertine flooring, high ceilings, crown molding, and bright natural light. First floor layout includes a spacious living/dining room and open concept kitchen/family room. The kitchen offers stainless steel appliances, a built-it oven and microwave, gas range, granite counters, bar top seating, and a walk-in pantry. Off the family room are French doors that open to a screened patio which overlooks the perfectly manicured backyard. The first floor primary bedroom is very comfortably sized and has a private en suite with double vanities, a walk-in shower, and jetted tub. There’s an additional guest room with full bath on the first floor as well, ideal for visiting guests. Upstairs are two generously sized bedrooms, each with ample closet space, and a shared hall bath. Additional highlights include natural gas, a Rinnai tankless hot water heater system, paver walkways, a detached Tuff Shed, tile roof, and more. Located in Winter Park’s desirable “tree streets” neighborhood this home is zoned for the A-rated Winter Park School District and is close proximity to the Winter Park Raquet Club, Interlachen Golf & Country Club, Rollins College, Park Avenue, and all of the fantastic shops and dining the area has to offer. This charming home won't last so schedule your showing today.