Winter Park Homes with Lake Front Water Frontage

Winter Park Homes with Lake Front Water Frontage

Welcome to Winter Park, a charming city located in the beautiful state of Florida. Known for its picturesque landscapes, vibrant community, and rich cultural heritage, Winter Park is a sought-after destination for homebuyers looking for a perfect blend of tranquility and modern amenities.

One of the most coveted features of homes in Winter Park is their lakefront and waterfront locations. Imagine waking up to stunning views of crystal-clear lakes or enjoying a relaxing evening by the water – living in a home with lakefront water frontage in Winter Park offers a unique and serene lifestyle that many dream of.

Whether you're looking for a cozy lakeside cottage, a modern waterfront estate, or a stylish condo with water views, Winter Park has a diverse range of properties to suit every taste and budget. From luxurious waterfront homes with private docks to charming lakefront bungalows with lush gardens, there's something for everyone in this idyllic city.

With its top-rated schools, thriving local economy, and abundance of recreational opportunities, Winter Park is not just a place to live – it's a place to thrive. Come and explore the real estate options in Winter Park, and find your perfect home with lakefront water frontage in this enchanting city.

Newest Winter Park Homes with Lake Front Water Frontage

100 S Interlachen Avenue Unit 401, Winter Park
$850,000
3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park
2139 Blossom Lane, Winter Park
$699,000
32789 Zip Code
Rare opportunity to build your custom waterfront home in the heart of Winter Park's 32789. This cleared, ready-to-build lot sits on a canal with boating access to Lake Killarney, one of the area's most sought-after ski lakes. Spend your days skiing and cruising, then boat up to the dock at Hillstone Restaurant for lunch or dinner with sunset views over the water. All this comes with the convenience and prestige of a Winter Park address, just minutes from Park Avenue, dining, and shopping. Some photos have been virtually staged.

2139 Blossom Lane, Winter Park
2500 Lee Road Unit 123, Winter Park
$169,900
1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
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 see why Lakeside Manor remains one of Winter Park’s best-kept secrets!

2500 Lee Road Unit 123, Winter Park
1602 Alabama Drive Unit 107, Winter Park
$1,150,000
2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code
Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

1602 Alabama Drive Unit 107, Winter Park
5303 Pine Lily Circle, Winter Park
$659,000
3 Beds ⋅ 2 Baths ⋅ Sanctuary At Aloma SubDv. ⋅ 32792 Zip Code
POOL HOME IN WINTER PARK! Beautifully maintained 2015-built one-story in the quiet, gated community of Sanctuary at Aloma, offering 2,265 sq ft with 3 spacious bedrooms, a dedicated den/flex/home office, and a separate formal dining room, all on one level with no stairs. The open-concept great room flows into a light-filled kitchen featuring a large center island, stone countertops, a sleek backsplash, and abundant cabinetry, perfect for entertaining. The private primary suite is a true retreat with a separate soaking tub and shower plus plenty of storage. Secondary bedrooms are well sized with great closet space. Step outside to your screen-enclosed in-ground pool, added in 2020, with a covered sitting area and a fully fenced, beautifully landscaped backyard, privacy rarely found at this price point. Additional features include tile and laminate flooring, an owned security system, an attached 2-car garage, public water and sewer, and excellent curb appeal with stucco exterior and carriage-style garage door. Low quarterly HOA and NO CDD. Minutes from SR-417 at Aloma Ave, placing UCF, Research Park, Oviedo, and downtown Orlando within an easy commute. Close to Winter Park Village, historic Park Avenue, Full Sail, Rollins College, and Orlando International Airport. All information deemed reliable but not guaranteed; buyer and buyer's agent to verify all measurements and features. Schedule your private showing today!

5303 Pine Lily Circle, 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
120 Broadview Avenue, Winter Park
$1,450,000
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 — $1,450,000 155' x 65' property + 65' lakefront. Option 2 — $1,250,000 115' 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
555 E Lake Sue Avenue, Winter Park
$2,095,000
4 Beds ⋅ 4 Baths ⋅ Lake Virgina Shores SubDv. ⋅ 32789 Zip Code
Welcome to the Timberlane Shores area, one of Winter Park's most desirable and established neighborhoods. This beautifully updated home sits on over a third of an acre with deeded access to Lake Virginia. Impeccably maintained, the 4-bedroom, 4-bath home offers 3,776 square feet of heated living space, including an office and sunroom. Inside, a welcoming foyer opens to a traditional floor plan with large formal living and dining rooms on either side. Straight ahead, the spacious family room with fireplace flows into the kitchen, where new quartz countertops and backsplash, upgraded appliances, and gorgeous travertine floors make this a true chef's kitchen. Beyond the kitchen, a light and bright sunroom looks out over the inviting pool and patio with outdoor kitchen. The downstairs office could easily be converted to a first-floor bedroom with an adjacent full bath. Upstairs, you'll find a large primary suite and three additional bedrooms. One of the home's most inviting features is the expansive upper balcony stretching the length of the house and overlooking the pool, perfect for entertaining or enjoying a quiet evening outdoors. Recent updates include a newly renovated kitchen, 2017 roof, and newly reimagined landscaping. Zoned for Audubon Park K-8 and Winter Park High School, and close to Winter Park's historic restaurant and shopping district, this is the perfect location to enjoy everything the area has to offer.

555 E Lake Sue Avenue, Winter Park
1803 Barker Drive, Winter Park
$2,190,000
4 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury finishes and appliances, expansive hurricane-impact windows, all-new HVAC and a whole-house water filtration system, along with double master suites with vaulted ceilings and distinctive architectural details throughout. Step outside, where 158 feet of lakeshore and your private dock invite you to enjoy the water at its best, from boating and waterskiing to beautiful sunrises and sunsets on the water. With approximately 3,400 square feet, four bedrooms, three baths, a detached garage/workshop and no HOA, this is a truly unique offering in one of Winter Park's most desirable locations.

1803 Barker Drive, Winter Park
7302 Swallow Run Unit 7302, Winter Park
$134,900
2 Beds ⋅ 2 Baths ⋅ Whisperwood SubDv. ⋅ 32792 Zip Code
Welcome to 7302 Swallow Run! This beautiful, move-in ready 2-bedroom, 2-bathroom condo offers the highly sought-after first-floor location and a prime setting directly across from both community pools. Nestled within the desirable Whisperwood community in Winter Park, this single-story condo features a wonderful split-bedroom floor plan and an open living concept with plenty of space to relax and entertain. Enjoy the convenience of NO CARPET throughout the home, along with a spacious living area that opens to a private balcony—perfect for enjoying your morning coffee or unwinding at the end of the day. The beautiful kitchen features gorgeous cabinetry, ample counter space, plenty of storage, and a full suite of appliances, all overlooking the open living area. A convenient breakfast bar provides additional seating, making everyday living and entertaining a breeze. The unit also includes a stackable washer and dryer for added convenience. Whisperwood is a quiet, welcoming condominium community with friendly neighbors and plenty to enjoy. Residents can take advantage of the community amenities and beautifully maintained grounds, all included in the affordable HOA fee. This particular unit enjoys an especially desirable location directly across from both community pools, a beautiful pond, and the community mailboxes. Beyond the community, you’ll enjoy all that the charming city of Winter Park has to offer. Located just three miles north of downtown Orlando, Winter Park is celebrated for its strong sense of community, beautiful parks, scenic chain of lakes, elegant homes, brick-lined streets, and mature tree canopy. The city offers an exceptional blend of historic charm and modern conveniences, with an array of shopping and dining destinations, museums, cultural attractions, and the renowned Rollins College. Conveniently located near Full Sail University and just a few miles from Rollins College, this home also provides easy access to major roadways including SR 408, SR 417, and SR 436. Come see 7302 Swallow Run and experience the convenience, charm, and lifestyle that make Winter Park such a wonderful place to call home!

7302 Swallow Run Unit 7302, Winter Park
311 E Morse Boulevard Unit 1-5, Winter Park
$2,475,000
3 Beds ⋅ 3 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two blocks from Park Avenue. Residence 1-5 is located on the quiet, private NE corner of the Whispering Water complex, and it offers the largest floor plan within Whispering Waters at 2,316 sq. ft. under A/C (plus two step-out balconies). This light-filled residence offers an open floor plan and raised ceiling heights. From the moment you enter, you are drawn to the breathtaking lake views and understated elegance of this spacious home. The lakefront great room includes a large living area with adjacent bar and dining areas. The living area opens to the kitchen allowing the lake view to be enjoyed in all main living areas. The kitchen has been updated with white wood cabinetry, a built-in stainless Bosch oven, Bosch glass induction cooktop, Bosch microwave, Subzero refrigerator with two freezer drawers and two additional built-in refrigerator drawers. The custom mirrored backsplash adds a luxury feel, and the flexible center console provides additional work space. The primary suite offers a large walk-in closet and en-suite bathroom with a large walk-in shower, custom floating vanity and elegant fixtures. Bedroom #2 includes two closets and is directly across the hall from a large full bathroom with tub/shower. The 3rd bedroom is currently configured as a large Family Room and includes built-in cabinetry, a private door to the South hallway, two closets and an adjacent alcove ideal for office space. In the photos you'll see a floor plan virtually depicting bedroom #3 with a wall and doorway to the main hallway and living areas. Bathroom #3 is just across the hall and features a large walk-in shower. Wait, there's more! Residence 1-5 includes your own covered boat slip (#1). The entire residence features new seagrass floor covering in all the main living areas. This neutral, organic flooring makes for the perfect contemporary, elegant foundation for your furnishings and for showing off your own custom carpets and rugs. Additional features include plantation shutters throughout, additional storage closet in the garage, and a designated parking space in the gated under-building garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. Residence 1-5 is the jewel of Whispering Waters. This home provides the very finest of Lakefront "lock and Leave" living in the heart of Winter Park. All measurements are approximate and Buyer to verify all dimensions. Please see attached Disclosures and Governing Documents.

311 E Morse Boulevard Unit 1-5, Winter Park
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