Winter Park Homes with Boatable Water Water Frontage

Winter Park Homes with Boatable Water Water Frontage

Winter Park, a charming city nestled in the heart of Florida, offers a unique blend of natural beauty, cultural attractions, and a thriving real estate market. Located in the Sunshine State, Winter Park is a vibrant community that attracts residents and visitors alike with its picturesque landscapes and boatable water frontage.

Situated in the state of Florida, Winter Park is known for its stunning lakes and waterways, making it a haven for those seeking homes with boatable water frontage. Whether you're an avid boater or simply enjoy the tranquility of living near water, Winter Park offers a variety of options to suit your needs. From luxurious waterfront estates to cozy cottages, there is a home for every lifestyle and budget.

Living in a home with boatable water frontage in Winter Park means enjoying direct access to the city's pristine lakes and waterways. Imagine waking up to panoramic views of the shimmering water, spending your weekends boating, fishing, or simply relaxing by the waterfront. With true boatable water frontage, you can easily dock your boat at your doorstep and explore the beauty of Winter Park's natural surroundings.

In addition to its natural beauty, Winter Park boasts a vibrant downtown area filled with shops, restaurants, and cultural attractions. From the renowned Morse Museum of American Art to the historic Winter Park Farmers' Market, there is always something to do and explore in this charming city.

If you're looking for a place that offers the perfect blend of natural beauty and urban amenities, Winter Park is the ideal destination. With its boatable water frontage and a wide range of real estate options, this city has something to offer everyone. Experience the best of Florida living in Winter Park, where the beauty of nature meets the comforts of home.

Newest Winter Park Homes with Boatable Water Water Frontage

2821 Chantilly Avenue, Winter Park
$415,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Manor SubDv. ⋅ 32789 Zip Code
WELCOME TO WINTER PARK LIVING! Situated on an expansive 0.76-acre lot in the established Winter Park Manor neighborhood, this charming 3-bedroom, 2-bathroom home offers a wonderful combination of space, comfort, and a peaceful waterfront setting. With approximately 250 feet of frontage along the small body of water identified as Lake Vella, the property provides a scenic backdrop and plenty of room to enjoy the outdoors. Inside, you'll find 1,440 square feet of heated living space featuring an open floor plan, vaulted ceilings, and a spacious living and dining area. The kitchen offers granite countertops, stainless steel appliances, ample storage, and a convenient breakfast bar. The primary bedroom includes its own en-suite bathroom. Step outside to the screened rear porch, where you can unwind and enjoy the surrounding greenery and water views. The generous lot offers plenty of possibilities for outdoor activities, gardening, or simply enjoying the extra space. Additional features include a one-car carport, central air conditioning, and NO HOA fees. Conveniently located near Winter Park's shopping, dining, parks, and everyday amenities, this property offers a unique opportunity to enjoy a spacious lot in a desirable Central Florida location. Schedule your private showing today!

2821 Chantilly Avenue, Winter Park
Winter Park
$2,100,000
4 Beds ⋅ 5 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code
Experience elevated living in this exceptional two-story Winter Park residence featuring 4 bedrooms and 4.5 bathrooms, custom designed with comfort, style, and entertaining in mind. Enjoy your own private outdoor oasis with a heated wading pool and outdoor kitchen with a gas grill, sink and two refrigerated drawers, perfect for relaxing or hosting family and friends year-round. Mature podocarpus line the outdoor space for added privacy. The luxurious primary suite offers a spa-inspired steam shower, along with custom closets and beautifully appointed custom vanities. The kitchen features custom cabinetry with both electric and manual operating cabinets, built-in coffee/espresso maker and walk in pantry adding a distinctive touch of convenience and functionality. Additional highlights include a Ring camera security system and a professionally coated garage floor. A rare opportunity to enjoy access to the private waters of Lake Killarney, adding an extra element of lifestyle and recreation. This exceptional home combines stylish features, indoor comfort, and outdoor entertaining in a desirable Winter Park location.

Winter Park
1500 Gay Road Unit 26-C, Winter Park
$255,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

1500 Gay Road Unit 26-C, Winter Park
2500 Lee Road Unit 123, Winter Park
$159,900
1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
NEW PRICE! REDUCED $10,000 — NOW ONLY $159,900! LIVE THE WINTER PARK LAKEFRONT LIFESTYLE WITHOUT THE LAKEFRONT PRICE TAG! This UPDATED, GROUND-FLOOR 1-bedroom, 1-bath condo offers 645 SF of move-in-ready living in desirable Lakeside Manor on beautiful Lake Killarney. Enjoy easy first-floor access, peaceful park-like grounds, a sparkling lakefront pool, clubhouse, community boat access and docks—all just steps from your door. The location is exceptional—minutes from Winter Park Village, Park Avenue, Rollins College, shopping, dining and entertainment, with quick access to I-4 and Downtown Orlando. Perfect as a primary residence, second home or low-maintenance getaway. UPDATED. GROUND FLOOR. LAKEFRONT COMMUNITY. PRIME WINTER PARK LOCATION. Come discover why Lakeside Manor remains one of Winter Park’s best-kept secrets! The current owners love this community so much, they purchased a larger unit and moved just steps away! Now this beautifully updated condo is ready for its next owners to call home.

2500 Lee Road Unit 123, Winter Park
533 Country Club Drive, Winter Park
$1,599,000
4 Beds ⋅ 4 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code
Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

533 Country Club Drive, Winter Park
120 Broadview Avenue, Winter Park
$1,250,000
3 Beds ⋅ 2 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE UNIQUE OPPORTUNITIES: Option 1 — $1,250,000 115' x 65' property + 65' lakefront. Option 2 — $1,450,000 155' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park
825 Palmer Avenue, Winter Park
$5,195,900
5 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of Lakes. Thoughtfully designed and being built by FG Schaub Custom Homes, this exceptional property offers the character of a timeless estate with the amenities and craftsmanship expected in a luxury new construction home. The residence will feature five bedrooms, a dedicated office, five full bathrooms, and two half bathrooms, with beautifully appointed living spaces designed for both refined entertaining and comfortable everyday living. The striking exterior showcases classic French Country influences, stone accents, decorative brick detailing, crisp stucco, expansive windows, and multiple gabled rooflines, creating an elegant and welcoming architectural presence. Outdoor living is equally impressive, with a private pool and spa, covered outdoor living area with roll away screens, and a full summer kitchen creating a resort-style retreat. A brand-new private boathouse, included with the property, is positioned directly on the canal and provides access to the Winter Park Chain of Lakes, offering the opportunity to enjoy boating, water sports, fishing, and so much more. Final plans, specifications and finishes are subject to change.

825 Palmer Avenue, Winter Park
2622 Lake Howell Lane, Winter Park
$3,400,000
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, water sports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property features a full 50 amp RV hookup with water and sewer hookups. The property is Agriculture zoned and allows horses. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating—the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home—it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

2622 Lake Howell Lane, Winter Park
151 N Orlando Avenue Unit 242, Winter Park
$269,000
2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Experience lakefront living at its finest in this exceptional Winter Park Condominium Community overlooking beautiful Lake Killarney. Hidden gem complete with access to a community dock, private boat ramp, and a fenced lakeside pool perfect for relaxing and entertaining. Ideally located just minutes from the heart of Winter Park, this home offers unparalleled walkability. Stroll to Park Avenue's renowned boutiques, restaurants, and nightlife, catch a movie at Regal Cinemas, or conveniently shop at Publix and Trader Joe's. With countless restaurants, bars, and everyday amenities just steps away, you'll enjoy the perfect blend of tranquil waterfront living and vibrant urban convenience. Whether you're boating on the lake, lounging by the pool, or taking in the spectacular evening sunsets, this is a rare opportunity to enjoy one of Winter Park's most desirable waterfront lifestyles.

151 N Orlando Avenue Unit 242, Winter Park
240 Killarney Drive, Winter Park
$1,175,000
3 Beds ⋅ 3 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.

240 Killarney Drive, Winter Park
230 Killarney Drive, Winter Park
$1,150,000
4 Beds ⋅ 1 Baths ⋅ Killarney Estates SubDv. ⋅ 32789 Zip Code
Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.

230 Killarney Drive, Winter Park
1500 Gay Road Unit 3C, Winter Park
$235,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
NEW PRICE/Seller Motivated! WINTER PARK LOCATION ALERT with AMAZING WALKABILITY to SO MANY shopping and dining options! Across from the newly renovated WP Shopping Village that includes top-rated restaurants, a movie theater, boutiques, grocery store and more! This 2bedroom/2 bathroom attractive second-story unit offers an updated kitchen and bathrooms with solid countertops. All solid flooring throughout - tile and laminate for easy care...no carpet. Enjoy the dining space that opens to the large great room and balcony where you'll love sitting in the evenings to relax. SPACIOUS BEDROOMS - Primary bedroom has an attached full bathroom and bedroom 2 has a LARGE walk-in closet. The 2nd Full Bathroom is accessed via a common hallway. The Chateaux Du Luc LAKEFRONT COMMUNITY offers FABULOUS AMENITIES that include an oversized heated pool, clubhouse, community deck, BBQ grill, 2 on-site saunas, updated on-site laundry facilities, and a resident-only boat ramp on skiable Lake Killarney. There's even storage for your Kayak or paddleboard! Roof 2025. Reach out today for your personal showing!!

1500 Gay Road Unit 3C, Winter Park
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