Winter Park Homes with Lake Front Water Frontage

Winter Park Homes with Lake Front Water Frontage

Located in the beautiful state of Florida, Winter Park is a charming city that offers a unique blend of natural beauty and urban amenities. Situated in Orange County, Winter Park is known for its picturesque lakes, historic architecture, and vibrant cultural scene.

One of the standout features of Winter Park is its stunning homes with lakefront water frontage. True to its name, this city is home to a plethora of properties that offer direct access to the glistening waters of its numerous lakes. Whether you're looking for a peaceful retreat or an active waterfront lifestyle, Winter Park has something to offer.

Imagine waking up to the serene views of Lake Virginia or enjoying a leisurely boat ride on Lake Osceola. With homes boasting lakefront water frontage, residents in Winter Park can indulge in a variety of water activities such as fishing, kayaking, and paddleboarding right from their own backyard.

In addition to the natural beauty, Winter Park also offers a vibrant downtown area filled with boutique shops, art galleries, and award-winning restaurants. Residents can explore the city's rich history by visiting the Charles Hosmer Morse Museum of American Art or strolling through the beautiful Rollins College campus.

With its idyllic lakeside living and a thriving cultural scene, Winter Park is a truly remarkable place to call home. Whether you're looking for a permanent residence or a vacation retreat, Winter Park's homes with lakefront water frontage provide the perfect opportunity to enjoy the best of Florida living.

Newest Winter Park Homes with Lake Front Water Frontage

$6,995,000
5 Beds 5.5 Baths Sicilian Shores SubDv. 32789 Zip Code
Luxurious lakefront living with unparalleled view of Lake Maitland, part of the famed Winter Park chain of lakes with 180 feet of water frontage. Enjoy tranquil views from the lake from almost every room. This custom home is located in the Via's of Winter Park and is close distance to downtown Park Ave and the Winter Park Racquet Club. This home was built by Gallimore and features five bedroom, five & one half bath. As you enter the foyer, you are immediately greeted by high ceilings, open floor plan and panoramic views of the lake. The family room is a fantastic place for entertaining, featuring a gas fireplace, wet bar with refrigerator and opens to the screened pool and gorgeous lakefront. The gourmet kitchen is a chef’s dream featuring a large center island, custom cabinetry, quartz surfaces, top of the line Thermador appliances, and walk-in pantry. The spacious master bedroom is a retreat of its own with amazing views of the lake and a sitting area. The master bathroom has custom cabinets with dual sinks, makeup vanity, modern stand alone tub, walk-in shower and a large walk around closet. There is a guest suite on the first floor with en suite bathroom and walk in closet. Two additional bedrooms upstairs with en suite bathrooms and a huge bonus room or fifth bedroom. This home also features a 3 car garage, a home office, laundry room and walk-in storage room with a large wine refrigerator. Step outside to the backyard paradise, where the pool, heated spa and sun shelf beckons you to relax and unwind. The large covered boat dock is a perfect place to watch the colorful sunset at night and has a separate enclosed storage room. Bring your boat and all your toys and enjoy lakefront living at its best! Roof and boathouse roof updated 2022.

1761 Pinetree Road, Winter Park

$1,070,000
4 Beds 3 Baths Lakeside Estates SubDv. 32792 Zip Code
One or more photo(s) has been virtually staged. Welcome to this luxurious 4-bedroom, 3-bathroom home nestled in the upscale neighborhood of Lakeside Estates. Built in 2015, this meticulously designed home spans 3,057 square feet of exquisite living space, boasting a perfect blend of elegance and functionality. Upon entering, you are greeted by a grand foyer leading to an expansive living room and dining room adorned with high ceilings and abundant natural light. The heart of the home is the gourmet kitchen, featuring a butler's pantry, granite countertops, stainless steel appliances, double oven, and a walk-in pantry, making it a chef's delight and an entertainer's dream. Adjacent to the kitchen is the family room featuring an accent wall and views of the outside patio. The master suite is a sanctuary unto itself, boasting a luxurious ensuite bathroom with soothing soaking tub, separate shower, his and hers vanities and a spacious walk-in closet. The additional bedrooms, split from the master, are generously sized and offer walk-in closets. Step outside to the resort style oasis, where a sun soaked salt water pool with a captivating waterfall and heated spa awaits. The pool, controlled by a Pentair automation system, adds an element of tranquility and elegance to the outdoor space. The residence also offers a dedicated office space, ideal for remote work or study. This energy-efficient home boast a solar panel system for electricity, ensuring sustainability and cost savings. Additional features include a three car garage with a Gladiator storage system for ample storage space, along with a 12 camera security system for added peace of mind. Lakeside is a beautiful gated community featuring a lake and boat dock and it is located close to Seminole County parks. Don't miss the opportunity to own this extraordinary property. Schedule a showing today and experience the beauty of this remarkable home!

1473 Via Sangro Place, Winter Park

$1,695,000
4 Beds 3.5 Baths Charmont SubDv. 32789 Zip Code
Welcome to your new Winter Park retreat! This custom home boasts exquisite craftsmanship, from its intricate custom woodworking to its elegant crown moldings and hardwood floors. As you step onto the beautiful brick walkway and through the front door, you're greeted by a sense of warmth and luxury. The main floor features a formal living room/den and a dining room which leads to a butler's pantry and a spacious kitchen with a 6 burner gas range with exterior exhaust hood, making this a Chef's Dream Kitchen. Natural light floods the home through numerous windows, creating a bright and inviting atmosphere. The primary bedroom, located on the main floor, offers a peaceful sanctuary with its luxurious ensuite bathroom, complete with dual sinks, a soaking tub, and a stand-up shower. A huge walk-in closet provides ample storage space. Upstairs, you'll find a grand loft, an office with built-in desk and cabinetry, and three additional bedrooms with two bathrooms. The home has been meticulously maintained and features a new roof, new HVAC system, whole house water filtration system, and a new tankless on-demand hot water heater. Outside, a sparkling pool awaits, surrounded by a beautifully landscaped yard. A 2-car detached garage with new flooring in the attic provides additional storage space, along with a shed. Located just outside of Baldwin Park, this home is situated on one of Winter Park's most desirable streets. Enjoy the beauty of Lake Virginia just a short stroll away. With its fantastic location and proximity to excellent Winter Park schools, this home is sure to be in high demand. Schedule your private showing today before it's SOLD!

1931 Laurel Road, Winter Park

$945,000
3 Beds 2.5 Baths Casa Jardin Condo SubDv. 32789 Zip Code
In a prime Winter Park location, between Mead Gardens & Lake Virginia, welcome to the Villas of Casa Jardin with look and intimate feel of an Old World Spanish Village * An architectural gem with exterior features including Spanish stucco finishes, turrets, balconies and arched doorways * Interior features include an elegant hardwood and wrought-iron spiral staircase rising to the top of the turret and providing access to the treetop terrace a hidden room and bonus storage space * Admire the beautiful winding staircase but don’t want to walk up it? Use the private, in-house elevator instead – it makes 3 story living, like one story! * The original owner of this exclusive residence has meticulously maintained it and enjoyed the lock-and-leave lifestyle for over 17 years! Enter through a covered porch with a gorgeous hand stained & arched front door into a foyer with synthetic stone that runs throughout the main level * Living room, with 17’ ceilings, enjoys abundant natural light as a result of a floor-to-ceiling wall of glass overlooking two story, screened atrium * Columned walkway leads to the family room and eat-in kitchen with center island * Expansive white quartz countertops with counter-to-ceiling subway tile make this very light, bright and inviting informal living space overlooking the atrium with pavers and glass sliding door access * Kitchen has butler’s pantry, bar fridge, closet pantry and overlooks delightful private garden area with access to natural gas for grilling * The second level of the staircase opens to an expansive balcony with hardwood floors overlooking living room & atrium * Hardwood floors extend from the balcony/hallway into the owner’s bedroom suite with luxurious bath including expansive double vanity, oversize Kohler jetted tub, glass shower, dual walk-in closets and private balcony * Secondary bedrooms are separate from primary bedroom & share a hall bath * 3rd bedroom, set up as a studio, has 16’ vaulted ceiling, is light & bright and has a sliding glass door leading to a private balcony * Washer & Dryer are conveniently located to all 3 bedrooms * In addition, there is a third-level featuring a secluded tree-top terrace and hidden office, exercise or media room with a window (approximately 200 additional square feet of air-conditioned space not included in the county records) * This romantic and private treetop hideaway provides secluded space for morning coffee, sunbathing and candlelight dinners (sunsets to the West - space launches to the East) * A 2 car garage has epoxy floors, a utility sink and extensive Closets by Design work and storage space * Since 2021, extensive exterior renovations include a new roof, painting, roof top terrace resealing, new screens, new light fixtures * Interior renovations include painting throughout, kitchen countertops, backsplash, solid oak stairs, solid oak flooring on the second level (including primary bedroom), LED lighting and fixtures * Association maintains exterior, irrigation, pest control, landscaping, termite bond * Amenities all within walking & biking distance include Park Avenue and deeded access to Lake Virginia with private neighborhood park including a dock, spacious grassy area, benches overlooking the lake, and canoe, kayak & paddleboard storage * Park overlooks beautiful Lake Virginia & Rollins College * Nearby are Mead Gardens, Winter Park Tennis Center, Azalea Park playground and the brand new 7 Oaks Park * Old Republic Home Warranty

1264 S Pennsylvania Avenue Unit 10, Winter Park

$2,199,999
5 Beds 4 Baths College Place Rep SubDv. 32789 Zip Code
Nestled in the beautiful heart of Winter Park, where the charm of Savannah meets the vibrant energy of sunny Florida, this exceptional property at 817 Antonette Ave is a masterpiece of architectural artistry. From the moment you arrive, you'll be captivated by the meticulous attention to detail and the seamless fusion of luxury and timeless elegance. The Georgian exterior facade sets the tone for what awaits inside. Handcrafted door arches, trim and exquisite fixtures throughout the home showcase the unparalleled craftsmanship that defines every aspect of this residence. Step through the grand entrance to discover a world of sophistication and refinement. High ceilings, intricate moldings, custom millwork, and artisanal touches adorn every room, creating a sense of luxury and charm. The living spaces are bathed in natural light, with oversized windows framing picturesque views of the lush surroundings. The centerpiece of the home is the atrium ceiling with 12 large skylights strategically placed to flood the whole home with natural light. Every corner of this residence is bathed in a warm, inviting glow at any time of day, creating a serene and uplifting atmosphere. The Bistro-style gourmet kitchen is a culinary delight, featuring top-of-the-line appliances, designer cabinetry, and a large banquette that blends modern convenience with old-world charm. Entertain guests in the elegant dining room or gather in the Moroccan-inspired family room with a fireplace. The primary suite is a private zen like sanctuary, offering a spa bath, large walk-in closet, and an office. Step outside to the enchanting courtyard. Just down the street, you'll find Lake Virginia, where residents of Antonette Avenue are included in access to a private dock, offering opportunities for boating, fishing, and leisurely strolls along the waterfront. This property also features a two-car garage, and an in-law suite with a full kitchen, bath, and a private entrance with its own yard. Located in one of Winter Park's most historic, tight-knit, and eclectic neighborhoods, College Quarter, this home offers a coveted blend of luxury, privacy, and convenience. With its architectural integrity, handcrafted details, central location, enchanting central skylight, and minutes’ walk to Lake Virginia and Park Avenue, it is a rare find that epitomizes the art of living in sunny Florida.

817 Antonette Avenue, Winter Park

$239,900
2 Beds 2 Baths Chateaux Du Lac SubDv. 32789 Zip Code
This charming second-floor unit presents an exquisite blend of modern updates and serene lakefront living. Nestled within a welcoming community, this condo boasts a meticulously updated kitchen adorned with solid wood cabinets and elegant stone countertops, complemented by sleek stainless steel appliances. The warmth of wood flooring flows throughout, enhancing the inviting ambiance of the space. Residents will find themselves in a picturesque lakefront community, complete with a range of amenities designed for leisure and social activities. The clubhouse serves as a hub for gatherings, while the community pool offers a refreshing escape under the sun. For those who enjoy outdoor cooking and dining, the lakefront grill stands ready for memorable meals against the backdrop of tranquil waters. Furthermore, the location is unbeatable, with the convenience of being within a short distance to the vibrant Winter Park Village, where shopping, dining, and entertainment options abound. The unit itself features two bedrooms and two bathrooms, providing ample space and privacy. The primary bedroom is a true retreat, featuring an en-suite bathroom for added convenience and a spacious walk-in closet to accommodate a range of wardrobe needs. This residence combines the best of modern living with the peacefulness of a lakefront community, making it an ideal home for those seeking comfort, style, and a touch of nature's beauty. This unit comes with parking space #50…. Come check out this charming condo today!!

1500 Gay Road Unit 9-C, Winter Park

$825,000
2 Beds 2 Baths Cloisters Condo SubDv. 32789 Zip Code
LAKE VIEW! Discover a haven of sophistication and tranquility in the heart of Winter Park with this extraordinary two-bedroom, two-bath condominium. Situated on the serene shores of Lake Osceola, this inviting residence offers a prime location paired with luxurious amenities, embodying the essence of refined downtown living. Spanning 1,351 square feet, the residence is a masterpiece of light and serenity, boasting an abundance of natural light that accentuates the artful design and tranquil views. The primary suite, a harmonious retreat, features an en-suite bath, a spacious dressing area with ample closet space, and the potential for an added washer and dryer, ensuring both comfort and convenience. The separate kitchen, a chef's delight, opens to a generous living and dining area, creating an ideal setting for intimate gatherings or quiet evenings at home, with vistas overlooking glistening Lake Osceola. More than just a place to call home, this condominium is a gateway to a lifestyle of elegance and ease. Amenities such as covered parking, an elevator, and proximity to daily conveniences enhance the living experience, while boat docks, a gym, and an elegant community room within the complex offer exclusive leisure options. Managed expertly by FirstService Residential, this property promises a seamless and harmonious living experience. Located just steps from the vibrant shopping and dining of Park Avenue, the charm of Winter Park Village, nearby fitness centers, and the intellectual allure of Rollins College, this home places you at the center of Winter Park's most coveted attractions. Embrace the opportunity to create lasting memories in this sophisticated sanctuary. Schedule your private viewing today and explore how this exceptional unit can become your canvas for an extraordinary life.

106 S Interlachen Avenue Unit 317, Winter Park

$1,050,000
3 Beds 3.5 Baths Mondrian/Winter Park Twnhms SubDv. 32789 Zip Code
Unparalleled Luxury Living: Modern townhomes on Lake Killarney where contemporary design meets lakeside tranquility! Experience waterfront luxury living at Mondrian Winter Park, an exclusive collection of 30 contemporary townhomes situated on the serene shores of Lake Killarney. Each meticulously designed residence boasts exquisite finishes, expansive storefront-style windows, and 11' ceilings to flood the interiors with natural light. This brand-new contemporary townhome with charming brownstone elements is a sophisticated residence boasting a unique layout, featuring the main living space on the second level for ultimate convenience and privacy. Revel in the seamless flow of the modern kitchen, dining room, and great room. A stylish primary bedroom and spa-inspired bath are located in the secluded rear of the home. This retreat includes two walk-in closets, a sitting area, beautifully appointed bath with designer tile, a frameless glass shower, and private water closet - thoughtfully designed for your comfort. Additionally, our highly advantageous split bedroom design offers two additional bedrooms with en suites on the first level, providing ample space and flexibility for your lifestyle. With the added convenience of a full-size laundry room, this townhome redefines elegance and functionality. A rooftop oasis complete with an outdoor kitchen, pergola, hot tub spa, and breathtaking lake views can be found on level three, this thoughtfully crafted space offers the ideal blend of comfort and sophistication. Located in the picturesque Winter Park just north of downtown Orlando, residents can indulge in lakeside living with access to a private boat slip, community kayaks, and a lakefront Pavilion. Whether you seek serene relaxation or vibrant entertainment, this prime location places you moments away from top-tier dining, shopping, and recreational amenities, ensuring a lifestyle of unparalleled convenience and luxury.

1760 Mondrian Circle, Winter Park

$935,000
3 Beds 2.5 Baths Casa Jardin Condo SubDv. 32789 Zip Code
Nestled within the tranquil confines of the Virginia Heights Neighborhood lies a truly exceptional property. Boasting three bedrooms and two and a half bathrooms, this unit is a testament to both luxury and practicality, providing residents with a haven of comfort and convenience. One of the standout features of this residence is its exclusive access to a private lake access park, a serene oasis where one can unwind amidst the beauty of nature. Additionally, the proximity to various amenities further enhances the appeal of this location. Residents can enjoy leisurely strolls to the WP Tennis Center, Park Ave, or take in the scenic surroundings at Azalea Playground Park, all just moments away from the doorstep. Step inside, and you'll be greeted by an interior that exudes sophistication and elegance. The kitchen is a chef's delight, featuring custom wood cabinets, sleek granite countertops, and a convenient walk-in butler's pantry. The living spaces are equally impressive, with designer lighting fixtures illuminating the hardwood floors and accentuating the elegant spiral staircase with decorative wrought iron. The allure of this residence extends beyond its interior. Step outside to discover a private South screened atrium, perfect for quiet relaxation or entertaining guests in style. Alternatively, ascend to the spacious rooftop terrace, complete with a heated and cooled bonus room. Recent upgrades to the building, including fresh paint and a brand-new roof, offer peace of mind and ensure that this residence stands the test of time. Positioned away from the street, this unit provides a sense of seclusion and privacy. Casa Jardin offers easy access to Lake Virginia, where residents can enjoy a variety of recreational activities such as paddle boarding and kayaking, facilitated by new storage racks. And with the vibrant Orange Avenue Shops & Dining just a short stroll away, the possibilities for entertainment and relaxation are endless.

1276 S Pennsylvania Avenue Unit 12, Winter Park

$2,200,000
4 Beds 4 Baths Windsong Lookout Landing 43/79 SubDv. 32789 Zip Code
Welcome to a Mediterranean masterpiece (.34 acres) crafted by IBK Construction, nestled in the prestigious Windsong neighborhood. This captivating residence boasts four spacious bedrooms, including a luxurious primary suite conveniently located on the main level. Expansive chef’s kitchen, adorned with top-of-the-line amenities and ample space for entertaining. Real oak wood floors and travertine complementing the inviting living spaces, complete with a cozy gas fireplace, perfect for intimate gatherings. Relish in the Florida sunshine with your private pool and large lanai, offering the ultimate outdoor oasis. Long driveway and a roundabout leading to a three-car garage, this home effortlessly combines convenience and luxury. HVAC- 2015-2016. Experience unparalleled comfort with abundant storage options and meticulously designed millwork features and solid doors throughout. Walk in attic storage as large as a basement. Enjoy the Windsong first class amenities- lakefront clubhouse and pool, kid pool and water park, playground, WP Chain of Lakes access, kayaks, paddleboards, fishing and parks. Scenic views surround you as you walk, ride bikes and look for peacocks native to the neighborhood. Top rated schools and minutes from Park Avenue and shopping. Close to hospital, Wellness Center and easy drive to schools. Don’t miss the opportunity to call this exquisite Windsong home yours. Schedule your showing today and envision your lifestyle in this remarkable sanctuary. Don’t miss the opportunity to call this exquisite Windsong home yours. Schedule your showing today and envision your lifestyle in this remarkable sanctuary.<div style="padding:56.25% 0 0 0;position:relative;"><iframe src="https://my.matterport.com/show/?m=LufH1cWiLS7&mls=1" frameborder="0" allow="autoplay; fullscreen" allowfullscreen style="position:absolute;top:0;left:0;width:100%;height:100%;"></iframe></div>

1610 Lookout Landing Circle, Winter Park

$2,250,000
4 Beds 3 Baths J Kronenberger Sub SubDv. 32789 Zip Code
WELCOME TO 820 MAYFIELD AVENUE! This pristine home sits on a .30 acre lot on a beautiful tree-lined brick street in the heart of Winter Park, offering a PRIVATE BOATHOUSE on the amazing Winter Park Chain of Lakes. This is a rare opportunity to to own a deeded boathouse on 50X25 lot with just steps away from the main house on Alabama Drive, nestled between Lake Osceola and Lake Maitland. The location is unparalleled, with everything Park Avenue has to offer within walking distance. Kraft Azalea Garden is just around the corner, adding to the charm and convenience of this address. Upon arrival, you'll be greeted by a charming brick driveway and immaculate landscaping that leads to the inviting front porch. Step inside to discover this light & bright home that will impress at every turn. The soaring ceilings create a sense of space and tons of natural light, complemented by architecturally delightful details such as open staircase, hardwood floors, crown molding and plantation shutters throughout. The updated kitchen is a chef's dream, featuring stainless steel appliances, an island breakfast bar, and a charming eat-in nook that overlooks the family room. The family room is perfect for gatherings with french doors leading to to an expansive wrap around rear screened porch with motorized screens. Step into the backyard and discover a true oasis. A sparkling pool, hot tub, trellised brick patio, meandering walkways create a serene retreat right at home. The elegant primary suite is a sanctuary with vaulted ceilings, a gas fireplace and large walk-in closet. It opens to luxurious bath featuring a soaking tub, a separate shower and dual sinks. Two additional bedrooms, connected by jack & jill bath, offer comfort and privacy. The cozy loft provides additional flex space. The fourth bedroom, currently being used as a home office, is attached to a full bath and is conveniently located on the first floor. Extras include: two TRANE AC units installed in 2023, Pella windows 2017, closet organizers throughout, 2 car garage, and natural gas. This home offers a rare blend of location, luxury, PLUS PRIVATE BOATHOUSE! WELCOME HOME to the the Winter Park lifestyle at its finest!

820 Mayfield Avenue, Winter Park

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