Winter Park Homes with True Waterfront Description

Winter Park Homes with True Waterfront Description

Welcome to Winter Park, Florida – a picturesque gem nestled in Orange County, known for its enchanting landscapes, vibrant arts scene, and, of course, its stunning waterfront properties. This charming city boasts a rich history, with its roots tracing back to the late 1800s, and has blossomed into a sought-after destination for those seeking a blend of natural beauty and urban convenience.

Winter Park is renowned for its tranquil lakes, lush parks, and tree-lined boulevards, making it an idyllic setting for outdoor enthusiasts and families alike. The city is home to a variety of cultural attractions, including the Morse Museum of American Art, which houses the world’s most comprehensive collection of Tiffany glass, and the scenic Winter Park Chain of Lakes, perfect for boating, fishing, and leisurely strolls.

When it comes to real estate, Winter Park offers an array of homes with true waterfront descriptions. Imagine waking up to the gentle lapping of water against your private dock or enjoying sunset views from your backyard patio. These stunning properties not only provide direct access to the serene waters but also feature beautifully landscaped gardens and spacious living areas designed for both relaxation and entertainment.

Whether you're looking for a cozy cottage or an expansive estate, Winter Park's waterfront homes cater to every taste and lifestyle. With its vibrant community, top-rated schools, and proximity to downtown Orlando, Winter Park is not just a place to live; it’s a lifestyle. Come discover the charm of Winter Park and find your perfect waterfront oasis today!

Newest Winter Park Homes with True Waterfront Description

4 Beds ⋅ 3 Baths ⋅ O6442064 MLS

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

2 Beds ⋅ 2 Baths ⋅ O6442721 MLS ⋅ 7 BLDG.

LAKE KILLARNEY CONDO IN WINTER PARK! Enjoy the best of Winter Park living in this beautiful 2-bedroom, 2-bath corner condo in the private lakefront community of Killarney Bay. Featuring an open floor plan, stone and wood flooring, high ceilings, quartz kitchen countertops, stainless-steel appliances, generous storage, and a stunning stone-accented fireplace. Plus a utility room with a full size washer and dryer. The spacious primary suite offers an oversized walk-in closet and private bath, while the second bedroom features its own en-suite bath and access to the private screened patio. Relax outdoors while enjoying peaceful Lake Killarney sunset views. Community amenities include covered assigned parking, a lakefront dock, fishing, and swimming pool plus paddleboard & kayak storage. Ideally located near Winter Park Village, Trader Joe’s, shopping, restaurants, and entertainment, this property offers an unbeatable combination of convenience and lakefront lifestyle. Perfect for a Winter Park primary residence or seasonal second home. Come discover why Killarney Bay is one of Winter Park’s most desirable places to live! Also available for Lease (O6440361) or Lease Purchase, Ask about special financing incentive!

720 Killarney Bay Court Unit 7-6, Winter Park

3 Beds ⋅ 3 Baths ⋅ O6441437 MLS ⋅ Bldg. Number 1 BLDG.

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

4 Beds ⋅ 3 Baths ⋅ O6433534 MLS

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

1 Beds ⋅ 1 Baths ⋅ O6438724 MLS ⋅ Lakeside Manor BLDG.

It doesn't get much better than this: Living in a Lakefront and Winter Park community, that is convenient to I-4 providing easy access to points north and south, downtown Winter Park, shopping, fine dining, and the price can't be beat. The HOA dues includes water, trash pickup, a full package from Spectrum including internet. Lakeside Manor is situated on the north side of Lake Killarney, a 239 acre lake that is perfect for sailing, motor boating and skiing. The lush courtyard, lakeside pool, clubhouse and gazebo, updated dock and private boat ramp make this a serene place to enjoy the best of Central Florida in a noisy world. This one bedroom condo is in original condition, with 3 year old A/C unit, and is ready for your personal touches to make it your own.

2500 Lee Road Unit 143, Winter Park

3 Beds ⋅ 3 Baths ⋅ O6437639 MLS

A rare corner lot in one of Winter Park's most established, increasingly in-demand Lake Forest Park neighborhood. This mid-century home has been meticulously maintained. With beautiful hardwood floors and updated systems throughout, there's nothing left to do but move in. The lot is the story here. A stunning mature oak anchors the front yard, and the corner position with no north-facing neighbor gives you privacy that's hard to find this close to town. Out back, a covered porch overlooks Lake Forest, plus a private sauna and a large shed built for a workshop, storage, or a future ADU. Quiet, shaded, genuinely peaceful. The kind of backyard people forget exists in-town. The street is whisper-quiet and made for evening walks, with Lake Forest views most homes in the area can't touch. Move in as-is and enjoy a home that's already been cared for the right way. Or use the lot and elevation to add a second story and expand the lake views, or build new entirely. Lake Forest is in the middle of a real transformation, with new luxury construction going up throughout the neighborhood. This lot puts you ahead of that curve - schedule your private viewing today.

2227 Howard Drive, Winter Park

2 Beds ⋅ 1 Baths ⋅ O6437574 MLS ⋅ Lake Killarney Condominiums BLDG.

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

A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custom dream home while enjoying the privacy and tranquility of one of Central Florida's premier waterfront locations. Spanning nearly 400 acres, Lake Howell is a skiable lake ideal for boating, water skiing, fishing, kayaking, canoeing, paddleboarding, and endless outdoor recreation. With expansive acreage, breathtaking water views, and ample space to create your own private estate, the possibilities are endless. The value is in the land, making this an incredible opportunity for those seeking a premier homesite in a highly desirable location. Don't miss your chance to own one of the area's rare large-acreage lakefront parcels.

1133 Bella Lago Cove, Winter Park

3 Beds ⋅ 4 Baths ⋅ O6430343 MLS

Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water views, the home combines refined craftsmanship and extraordinary lakefront serenity with warm European Contemporary architecture influenced by Belgian design and Organic Modern principles. Expansive, minimalist-profile windows frame the water from nearly every principal living space, while a dramatic 12-foot sliding glass wall connects the open living area to approximately 1,500 square feet of additional outdoor living. Multiple terraces, an integrated outdoor kitchen and beautifully landscaped surroundings create an exceptional setting for waterfront entertaining or quiet mornings beneath the oak canopy. Inside, natural wood, matte black accents, architectural lighting and tactile materials establish a cohesive, warm and inviting aesthetic. Custom white oak wall panels made in Spain, hand-cut white oak beams and architectural transitions, a textured brick feature wall, built-in Sonos audio and a dedicated entertaining bar reflect the attention given to every detail. The European-inspired kitchen features full-height cabinetry incorporating materials imported from Portugal, extensive integrated pantry storage, a Thermador appliance suite with a 36-inch range and griddle, and a Miele steam oven. Positioned at the heart of the living area, the kitchen creates an effortless setting for everyday life and entertaining, always with the lake close at hand. Each of the home’s three bedrooms includes a private en-suite full bath, with an additional powder room serving the common areas. A flexible lake-view office—currently used as a fitness and sauna studio—offers an inspiring setting for work, wellness or creative pursuits. The primary suite opens through nearly eight feet of accordion-style glass doors to a private rooftop terrace, inviting morning coffee, yoga, sunbathing or evening movies beneath the sky. Beyond its architectural design, the comprehensive transformation includes a new roof and roof components, electrical wiring, plumbing and piping, four-zone HVAC system, windows, stucco, drywall, flooring, kitchen and bathrooms. The result combines the character, proportions and established setting of an Old Winter Park home with the quality, efficiency and peace of mind expected from a modern custom residence. Turnkey, distinctive and intimately connected to the water, this exceptional home brings together architectural vision, modern livability and the coveted Winter Park lifestyle on the shores of Lake Sylvan.

1420 Aloma Avenue, Winter Park

3 Beds ⋅ 4 Baths ⋅ O6426102 MLS ⋅ Lake Spier BLDG.

Welcome to Lake Spier Crossing with NO CDD and low HOA fees, an exclusive boutique lakefront community built by Winter Park's premier builder, Meridian Homes. Nestled between the peaceful shores of Lake Spier and Lake Compton, this intimate enclave of just 10 luxury townhomes offers architecturally distinctive modern contemporary design and low maintenance living in one of Winter Park's most desirable locations. Residents enjoy private access to three community docks on Lake Spier, perfect for paddleboarding, kayaking, fishing, or simply relaxing by the water. Built in 2023, this stunning residence showcases soaring ceilings, abundant natural light, wide plank hardwood flooring, designer lighting, custom cabinetry, stone countertops, premium Café appliances, and an open concept floor plan designed for both everyday living and entertaining. Every detail was thoughtfully selected to create a timeless aesthetic, blending luxury finishes with modern functionality. Since purchasing the home, the owner has thoughtfully enhanced the property with motorized electronic shades throughout the first floor, retractable roll away screens that seamlessly extend the indoor and outdoor living experience, and a custom built Murphy bed in the guest bedroom, creating a versatile space that easily functions as both a home office and comfortable guest suite. The spacious primary suite offers a luxurious retreat, while the additional bedrooms provide flexibility for family, guests, or remote work. An upstairs laundry room and attached two car garage complete the home's thoughtfully designed layout. Step outside to enjoy your private fenced backyard with premium wrought iron fencing overlooking a peaceful, wooded lake view setting, providing both privacy and a beautiful natural backdrop. Beyond the community, you'll love the unbeatable location. Walk or bike to Downtown Baldwin Park's popular restaurants, shops, parks, and weekly events, enjoy the nearby Cady Way Trail and Lake Baldwin Dog Park, and take a short drive to Park Avenue, Rollins College, Winter Park Village, AdventHealth Winter Park, and Downtown Orlando. Combining architecturally distinctive modern contemporary design, luxury finishes, thoughtful owner upgrades, exclusive lake access, and an exceptional Winter Park location, this remarkable residence offers the perfect blend of elegance, convenience, and the lock and leave lifestyle today's buyers are searching for.

1927 S Lakemont Avenue, Winter Park

3 Beds ⋅ 3 Baths ⋅ O6415977 MLS

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

4 Beds ⋅ 1 Baths ⋅ O6415950 MLS

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

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