Orange County Homes with Sailboat Water Water Frontage

Orange County Homes with Sailboat Water Water Frontage

Welcome to Orange County, Florida – a vibrant gem nestled in the heart of the Sunshine State! Known for its stunning landscapes, rich cultural heritage, and a warm community spirit, Orange County offers an idyllic lifestyle for those seeking both adventure and tranquility. With its picturesque lakes, lush parks, and proximity to Orlando's world-famous attractions, this county is an ideal destination for families, retirees, and anyone looking to embrace the Florida lifestyle.

One of the most alluring features of Orange County is its breathtaking homes with sailboat water frontage. Imagine waking up each morning to the gentle sounds of water lapping against your dock, with the sun casting a golden hue over the serene landscape. These waterfront properties not only provide direct access to some of Florida's most beautiful waterways but also offer a unique lifestyle that blends relaxation with recreation. Whether you’re an avid sailor, a fishing enthusiast, or simply someone who appreciates the beauty of nature, these homes are perfect for you.

Living in a sailboat waterfront home means endless opportunities for outdoor adventures. Picture yourself cruising along the tranquil waters, exploring hidden coves, or enjoying a sunset sail with friends and family. Additionally, the vibrant communities surrounding these properties often host events, providing a sense of camaraderie and connection among neighbors.

In Orange County, you’ll find more than just a home; you’ll discover a lifestyle filled with sunshine, community, and the soothing embrace of nature. Come explore the possibilities and make your dream of waterfront living a reality!

Newest Orange County Homes with Sailboat Water Water Frontage

6518 Sawyer Shores Lane, Windermere
$2,190,000
5 Beds ⋅ 6 Baths ⋅ Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
Virtually Staged. Under Construction. Estimated completion: January 2027. Commanding architecture, soaring interiors and access to Lake Sawyer define this new contemporary residence in sought-after Windermere. Set on a wide 0.39-acre lot, its striking facade makes an immediate impression, while approximately 100 feet of canal frontage opens the door to a lifestyle on the water. As the first home along the canal from the lake, the property enjoys a short waterway connection to Lake Sawyer, with an existing floating platform designed for a personal watercraft. Offering 3,582 square feet of conditioned living space and 4,865 total square feet, the home features five bedrooms, each with an en-suite bathroom, plus a powder room, dedicated office and three-car garage. Twelve-foot ceilings on both floors and a dramatic double-height space create an exceptional sense of scale. The open layout connects the kitchen, dining and living areas for effortless everyday living and entertaining, while the main-floor primary suite offers a comfortable retreat with a walk-in closet and spacious bathroom. Extensive cabinetry and built-ins bring a tailored aesthetic throughout the home. Planned finishes include stone countertops, porcelain tile and warm wood-look flooring, complemented by a gas cooktop and an electric fireplace. The design balances contemporary presence with inviting spaces that feel comfortable to live in. Outside, a private heated pool and covered rear lanai with a grill and sink set the scene for relaxed afternoons and evenings with guests. Planned artificial turf around the pool, hardscape surfaces and landscaping complete an outdoor setting designed for enjoyment with easy upkeep. With no HOA, this property pairs the appeal of new construction with a waterfront setting close to the lake. Within walking distance of Windermere Preparatory School, ranked No. 1 among private high schools in Orange County by Niche for 2027, and conveniently located near Windermere High School. Public schools listed for this address are Windermere Elementary, Bridgewater Middle and Windermere High, all earning an A in Florida's 2026 school grades. Buyers should verify current school zoning. Limited personalization may be considered, subject to builder approval and construction timing. Discover a home where the arrival is memorable, the interiors feel expansive and time on Lake Sawyer can become part of everyday life. Images include architectural renderings and virtual staging; final materials and finishes may vary.

6518 Sawyer Shores Lane, Windermere

261 Zachary Wade Street, Winter Garden
$1,500,000
4 Beds ⋅ 4 Baths ⋅ Lakeview Reserve 46/149 SubDv. ⋅ 34787 Zip Code
Few homes make an entrance like this one: renovated, lakefront and minutes from downtown! Welcome to this exquisitely updated 4-bedroom, 3.5-bath pool home with 90 feet of frontage on Lake Apopka, the fourth-largest lake in Florida, in the gated, golf-cart-friendly community of Lakeview Reserve. Expansive open-water views, streaming natural light and a beautifully reimagined interior create an unforgettable first impression. LOCATION: Just 2 miles to historic Downtown Winter Garden, reachable by golf cart, with Plant Street's restaurants, boutiques, events and the famous Saturday Farmers Market. The West Orange Trail is right outside the community gate, six highly rated golf clubs are within a 5-mile radius, and top-rated elementary and middle schools are less than a mile away. Enjoy easy access to shopping, Florida's Turnpike, downtown Orlando and the theme parks. RENOVATION: An extensive whole-home renovation brings a polished contemporary feel, with large-format porcelain tile, fresh paint and striking new lighting. The living room's panoramic water views anchor an open-concept layout that flows into the oversized dining room and kitchen. The completely renovated kitchen features high-gloss white flat-panel cabinetry, frosted glass accents, quartz countertops, a full-height quartz backsplash, an oversized waterfall island, stainless steel appliances, abundant storage and a built-in bar with wine storage. Every bathroom is beautifully remodeled, and each has a window and exhaust fan. The first floor hosts the primary suite plus two additional bedrooms, all with 11-ft ceilings, and every bedroom in the home enjoys a lake view. The primary suite offers real hardwood floors, two walk-in closets and a private screened porch overlooking the lake. Its spa-inspired bathroom includes dual vessel sinks, a makeup area, jetted soaking tub and glass-enclosed shower with rainfall and body spray fixtures. A first-floor office or den adds a quiet place to work. Upstairs, real hardwood continues to an oversized loft/flex space with full bath, walk-in closet and separate HVAC, ideal for guests or entertainment. Two Florida rooms, one on each floor, each with its own mini-split system, offer year-round panoramic lake views. OUTDOORS: A fenced, private backyard opens to sweeping open-water views. The recently resurfaced saltwater pool (new pump and filter 2026) and freshly repainted pool deck lead to a private covered dock with a 5,000-lb electric boat lift, electricity and water. Spend afternoons swimming, boating or fishing, then watch brilliant Florida sunsets from the dock. An extensive driveway and freshly painted two-car garage with built-in storage add everyday convenience. ENERGY EFFICIENT: This solar-powered home also features all new windows (2024), a new main first-floor AC (2026) and mini-split systems in both Florida rooms. The seller currently pays only an approximately $30 monthly grid fee, compared to a previous $500-$600 monthly electric bill. The seller will pay off the solar loan at closing, OR the purchase price may be reduced if the buyer assumes the existing low-interest solar panel loan. Mornings of sunlight on the lake, afternoons by the pool or on the boat, evenings on the dock beneath a painted Florida sky, with downtown Winter Garden just a golf cart ride away. This is the feeling of being on vacation every day, without ever leaving home.

261 Zachary Wade Street, Winter Garden

515 W 2nd Avenue, Windermere
$3,300,000
4 Beds ⋅ 6 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code
Experience the extraordinary lifestyle of waterfront living in the heart of historic Windermere. Set on approximately 2/3rd of an acre with an impressive 100 feet of frontage on the renowned Butler Chain of Lakes, This home offers a rare combination of luxury, privacy, space, and direct access to one of Central Florida's most coveted boating destinations. This beautifully appointed custom residence offers nearly 4,000 square feet of living space with four bedrooms, soaring ceilings, elegant formal living and dining areas, a spacious kitchen and family room, game room, wet bar, and a thoughtfully designed split-bedroom floor plan. Rich wood and travertine marble flooring, refined architectural details, generous windows bath the main living areas with natural light, and multiple gathering spaces create an atmosphere that is both sophisticated and inviting. A whole house natural gas generator and city water provide peace of mind knowing your family is porotected during the worst Florida storms The primary suite is a private retreat, featuring a luxurious bath with spa-style amenities, a generous walk-in closet, and a serene connection to the surrounding grounds. The home's open living spaces are designed for effortless entertaining, while the separate formal areas provide an elegant setting for more intimate occasions. Outside, the property becomes a private resort. Enjoy the pool and spa surrounded by mature landscaping and expansive outdoor living areas. The private boathouse has a covered boat lift with a "Touchless" Canvas Boat cover that protects your boat from animals and the elements , 2 Jet Ski lifts, Sitting area with fan and mood lighting, Garden hose with city water for cleaning, seawall that has a small beach carved in to allow for playing in the sand of the crystal clear lake, and direct lake access make this an exceptional opportunity for boating, water sports, fishing, and sunset cruises throughout the Butler Chain. Life here extends beyond the property itself. Located on one of Windermere's most desirable paved streets, the home is just moments from the charm of historic downtown Windermere, with its tree-lined streets, local shops, restaurants, parks, community amenities, and small-town atmosphere. Residents enjoy the unique privilege of living among the lakes while remaining conveniently connected to Central Florida's premier dining, shopping, entertainment, and attractions. The Town of Windermere describes its lakes as a beloved community privilege, with the Butler Chain comprising a remarkable network of interconnected waterways. Whether you're enjoying coffee overlooking the water, entertaining beside the pool, stepping aboard your boat for an afternoon on the chain, or returning home to the peaceful canopy of mature trees, this home embodies the very best of Windermere lakefront living. Original house was built in 1961 but completely expanded and remodeled in 2000 - present owner made upgrades in 2023 - call for details

515 W 2nd Avenue, Windermere

3126 S Osceola Avenue, Orlando
$520,000
3 Beds ⋅ 3 Baths ⋅ Jewel Shores SubDv. ⋅ 32806 Zip Code
Price Change to $520,000. Great Location! Great Square Footage! Great Schools! Spacious South Orlando Home with an awesome Opportunity! Located in one of South Orlando’s most desirable areas, this 3-bedroom, 2.5-bath home with a den offers 2,739 heated square feet and sits on a generous 0.30-acre lot. You’ll enjoy convenient access to Downtown Orlando while being zoned for highly sought-after Boone High School and Blankner K-8 School. The home was substantially remodeled in 2008, creating a spacious and functional floor plan. The large kitchen features wood cabinetry and an extended island that provides an excellent gathering space between the kitchen and dining area. The home also offers a comfortable family room and a generously sized primary suite with a remodeled primary bath. At the front of the home, the living room features a classic wood-burning brick fireplace, creating a warm and inviting space for relaxing or entertaining. Additional features include inside laundry, a two-car garage, and two HVAC systems serving different areas of the home. The rear HVAC system dates to 2008, while the front HVAC system is brand new in 2025. The roof is approximately three years old, providing valuable peace of mind for the next owner. Step outside to the covered rear patio overlooking the large backyard. With approximately 0.30 acres, there’s plenty of space for outdoor living, gardening, recreation, a pool, or simply enjoying the privacy and room that larger lots provide. The backyard also includes two storage sheds for additional workspace or storage. This home may not be completely perfect or fully updated—and that’s exactly where the opportunity lies. The combination of nearly 2,800 square feet, a large lot, desirable schools, major improvements already completed, and an excellent South Orlando location creates tremendous potential for the right buyer. Whether you’re looking for a spacious home in a convenient location or a property where you can add your own personal touches and build equity, this is an opportunity worth seeing. Don’t let this one get away—text today to schedule a private showing and come see the possibilities for yourself!

3126 S Osceola Avenue, Orlando

2434 Trace Ave, Belle Isle
$460,000
3 Beds ⋅ 2 Baths ⋅ Nela Isle Island Sec SubDv. ⋅ 32809 Zip Code
Virtually Staged. Price improvement bringing this beautifully updated Belle Isle home to an attractive new price point. Welcome to 2434 Trace Ave, where timeless character, thoughtful renovations, and everyday functionality come together. From the moment you arrive, the paver driveway and front walkway create a polished first impression, while mature landscaping and the home’s established setting add to its inviting curb appeal. An attached two-car garage provides everyday convenience without taking away from the home’s charm. Upon entering, you’ll immediately appreciate the open layout, wood-look tile flooring throughout the main living areas, and an abundance of natural light. The beautifully remodeled kitchen serves as the heart of the home, featuring shaker cabinetry, granite countertops, stainless steel appliances, and a striking hammered copper farmhouse sink. Just beyond the kitchen, the spacious laundry room offers additional cabinetry, a utility sink, ample workspace, and its own dedicated mini-split system for added comfort. The primary suite includes a spa-inspired bathroom with a custom walk-in shower, floor-to-ceiling marble-look tile, a frameless glass enclosure, dual shower heads including a rainfall shower, and recessed niches with herringbone tile accents. Thoughtful updates continue throughout the rest of the home with updated windows, newer interior and exterior doors, fresh paint, custom shiplap details, updated trim, and recessed lighting, creating a cohesive, move-in-ready feel from room to room. Outside, the spacious paver patio and fully fenced yard offer plenty of room to relax, entertain, or enjoy with pets, while gutters and an irrigation system add practical everyday convenience. Beyond the home itself, Belle Isle offers the kind of community buyers are often searching for but rarely find. Enjoy the freedom of no HOA, quiet tree-lined streets, a golf-cart-friendly atmosphere, nearby access to the Conway Chain of Lakes, and highly regarded schools, including Cornerstone Charter Academy. You’re also just minutes from Downtown Orlando, Orlando International Airport, Lake Nona, shopping, dining, and major roadways, giving you the best of both worlds—peaceful neighborhood living with easy access to everything Orlando has to offer. If you’ve been searching for a beautifully updated home with character, functionality, and access to one of Central Florida’s most distinctive lake communities, 2434 Trace Ave is one you won’t want to miss. Schedule your private showing today and experience what makes Belle Isle such a special place to call HOME!

2434 Trace Ave, Belle Isle

2400 Lauderdale Court, Orlando
$545,000
3 Beds ⋅ 2 Baths ⋅ Isle Catalina SubDv. ⋅ 32805 Zip Code
Brand New Roof just installed in October! Beautifully Remodeled 4 Bedroom MID-CENTURY MODERN CANALFRONT Home with Private Pool! Direct access to CLEAR LAKE, Orlando's Most CENTRAL TRUE SKIABLE LAKE, only 4 Miles from Downtown Orlando! Keep your BOAT directly behind your home with easy no bridge access to the lake from your private seawall! This Backyard OASIS features a Private Swimming Pool with Pool Heater, Beautiful Paver Deck, Huge Covered Lanai area with built-in BBQ, all situated on nearly a 1/4 Acre fenced lot. Peaceful Canal Views where you can Relax, Listen to the Birds, and Soak in Nature every day. Inside, you'll love the Tastefully Updated Open Floor Plan featuring a Stunning Kitchen with Tall Soft Close Shaker Cabinets, Stainless Steel Appliances, and Gorgeous Granite Countertops throughout both the kitchen and bathrooms, perfectly blending style, function, and Timeless Elegance. The Wonderful Layout offers a Large Open Family Room, Vaulted Ceilings, Recessed Lighting, Plantation Shutters and Luxury Vinyl Plank Flooring throughout the home. There’s a 2nd additional Living Area and multiple areas for dining. The well located primary bedroom has access to the Lanai pool area and a walk-in closet with built-ins you’ve only dreamt of! All these Wonderful home features provide exceptional flexibility for both everyday living and entertaining your friends. This Iconic Mid-Century Design combines Premium Finishes with Modern Designer Upgrades to create an Impressive Home for you to enjoy! The Isle of Catalina community provides access to the Community-Owned Private Waterfront Complex featuring a Private Electronic Gated Boat Ramp, Recreational Building, Volleyball Court, Picnic Tables, and Incredible Views of the Downtown Orlando Skyline across the 358 acre Clear Lake, the Second Largest Lake in Orlando all for HOA dues of only $197 per year. Enjoy Boating, Water Skiing, Wakeboarding, Beautiful Sunsets, and a True Waterfront Lifestyle right in the heart of the city! This SUPER CENTRAL Location offers some of the Best Access to Orlando’s Restaurant and Entertainment Districts and I-4, only minutes from Universal Studios, CityWalk, , Mall at Millenia, SODO Shopping, LA Fitness, Planet Fitness, International Drive, SeaWorld, Walt Disney World, Sand Lake Restaurant Row, and Downtown Orlando. This is not only a home but a Lifestyle change, Boatable Opportunities like this are Rare!...don't miss your chance to own this GEM that perfectly combines a great Central location, Mid-Century Charm, Modern Luxury, and Unbeatable Orlando Waterviews and Sunsets!

2400 Lauderdale Court, Orlando

2009 Woody Drive, Windermere
$1,125,000
4 Beds ⋅ 3 Baths ⋅ Windermere Downs SubDv. ⋅ 34786 Zip Code
Welcome home to your own Florida retreat, nestled on a generous 0.74-acre lot along the canopy-shaded, oak-lined streets of highly sought-after Windermere Downs. With access to the famed Butler Chain of Lakes and an array of community amenities, this property offers a rare combination of privacy, space, and the Windermere lifestyle. Windermere Downs residents enjoy amenities such as a private beach recreation area with access to the Butler Chain of Lakes, complete with a boat ramp and dock, white sandy beach, roped-off swimming area, and playgrounds. Two additional neighborhood parks offer playgrounds and tennis courts, making it easy to enjoy everything this established community has to offer. A spacious paver driveway leads to the garages offering parking for four cars., while a flagstone walkway welcomes you through the double-door entry. Inside, the foyer opens to bright formal living and dining rooms framed by two large bay windows. The kitchen features travertine flooring, multiple French doors, stainless steel appliances, and a gas range, with convenient access to the dining and family rooms. The inviting family room centers around an authentic Old Chicago Brick fireplace and features three skylights that bring in an abundance of natural light. The spacious primary suite offers a private retreat of its own, with French doors opening directly to the screened pool lanai. The en-suite bathroom is finished with a Kohler clawfoot tub and high-end fixtures. Beyond the living spaces, the backyard is a private oasis surrounded by mature greenery. A screened-in pool with travertine decking provides the perfect place to relax, while the expansive open travertine patio offers plenty of room for gatherings and outdoor dining. Additional features include a whole-house propane generator, 1,000-gallon underground gas tank, hybrid water heater, irrigation well, and valuable 2026 updates including a whole-house re-pipe, fresh exterior paint, and new soffits. With an expansive homesite, four-car garage, pool, and coveted Windermere Downs amenities, this is Florida living at its best.

2009 Woody Drive, Windermere

2500 Lee Road Unit 220, Winter Park
$199,900
2 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms and 1 bathroom with a functional layout suited for everyday living. Thoughtfully updated throughout, this unit features a modern kitchen with stainless steel appliances, charcoal quartz countertops, and a spacious island with ample storage. The bathroom has also been updated with contemporary finishes, while the unit's clean, modern design creates an inviting atmosphere throughout. A new A/C installed in 2025 provides added comfort and peace of mind. The floorplan includes comfortable living and dining areas, while the secondary bedroom offers flexibility for guests, a home office, or additional storage. The unit overlooks a beautifully landscaped courtyard and is conveniently located near designated parking. Residents enjoy access to a variety of community amenities, including a clubhouse, pool, laundry facilities, park areas, and dock access on Lake Killarney. The lakefront setting provides a peaceful environment and an opportunity to enjoy the surrounding natural beauty. Located in the heart of Winter Park, the condo is close to shopping, dining, parks, and popular destinations such as Winter Park Village, Park Avenue, College Park, Maitland, and Downtown Orlando. With its desirable community amenities and prime Winter Park location, this move-in-ready condo offers exceptional value and convenience.

2500 Lee Road Unit 220, Winter Park

2406 Sweetwater Country Club Drive, Apopka
$530,000
3 Beds ⋅ 2 Baths ⋅ Sweetwater Country Club SubDv. ⋅ 32712 Zip Code
Welcome to Les Chateaux: a unique collection of elegant French/Mediterranean style golf villas perched on the serene fairway of Sweetwater Golf & Country Club. This beautiful villa backs up to the third hole putting green, perfect for enjoying the golf course views and expansive space. It even has an extra garage for your golf cart, in addition to its already ample two car garage. Come inside and explore the fun & functional flow of this lovely 3 bedroom home with many special features: smartly decorated entry foyer, large eat-in kitchen, walk-in pantry, inside laundry room with ironing board cupboard, plantation shutters throughout, open concept dining room/living room with a wood burning fireplace (piped for gas, if desired) and multiple French doors that open up to the gorgeous Florida room (also under heat & air). This home is made for entertaining with it’s unique wrap around corner bar complete with brass foot rails and bar fridge. Brand new beautiful barrel tile roof this year! Other mentionables: deluxe GE Refrigerator less than 2 years old; Bosch dishwasher; washer/dryer stays, PLUS a second full size fridge in the garage; AC replaced in 2021. Les Chateaux is a tasteful enclave of 20 tile roof villas nestled in the desirable & expansive neighborhood of Sweetwater Country Club. The Sweetwater area is flush with winding streets, mature trees, lush landscaping, and multiple trails & parks. Residents have legal access to Lake Brantley, a beautiful 287 acre freshwater spring-fed lake teaming with fish and other wildlife. Lake activities include fishing, swimming, sailing, water-skiing, jet-skiing, wake-boarding, etc. Lake access is via a community beach, dock, and boat ramp. Other recreational facilities include tennis, basketball, pickleball, beach volleyball and a clubhouse for gatherings. After your fun filled day, wind down at the newly renovated Sweetwater Country Club restaurant and bar: The Tuscan Lounge & Grill, or another neighborhood favorite: Wekiva Island. Wekiva State Park is just across the street, downtown Orlando only 10 miles away, theme parks 20-30 miles away, and gulf or ocean beaches just a short trip to the east & west. Please note there are two HOA fees: Les Chateaux @ 322/month that covers ground maintenance, landscaping, common areas, etc PLUS INTERNET & CABLE services! Then there is a master HOA for Sweetwater Country Club that is $420 twice a year ($840 per year or essentially $70/month) and includes all the community amenities listed above. So, TOTAL HOA expense for both associations COMBINED is $392/month which includes INTERNET & CABLE: a bargain in today’s world and a lot of bang for the buck!

2406 Sweetwater Country Club Drive, Apopka

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