Orange Homes with Sailboat Water Water Frontage

Orange Homes with Sailboat Water Water Frontage

Welcome to the sun-drenched paradise of Orange County, Florida, where vibrant communities and breathtaking natural beauty intertwine. Nestled in the heart of Central Florida, Orange County is renowned for its rich history, lush landscapes, and a plethora of recreational opportunities. From the bustling attractions of Orlando to the serene charm of its surrounding suburbs, this county offers an ideal blend of urban excitement and tranquil living.

One of the most coveted features of Orange County is its stunning homes with sailboat water frontage. Imagine waking up to the gentle lapping of waves and the soft glow of sunrise reflecting off the water. These exquisite properties provide direct access to the sparkling waterways, allowing you to sail away into the sunset right from your backyard. Whether you’re an avid sailor, a fishing enthusiast, or simply someone who appreciates the peacefulness of waterfront living, these homes are a dream come true.

The neighborhoods surrounding these sailboat water homes are as inviting as the properties themselves. Enjoy leisurely strolls along scenic waterfront parks, partake in community events, or indulge in the culinary delights of nearby eateries. With excellent schools and family-friendly amenities, Orange County is a fantastic place to plant roots and create lasting memories.

Discover the enchanting lifestyle that awaits you in Orange County, where the allure of sailboat water living meets the vibrant pulse of Florida life. Your dream home is just a sail away!

Newest Orange Homes with Sailboat Water Water Frontage

3 Beds ⋅ 3 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Timeless Charm in the Heart of Downtown Windermere. Nestled beneath a canopy of majestic oak trees on one of Windermere’s most picturesque streets, this beautifully maintained three bedroom, two and half bath residence offers the perfect blend of classic Florida charm and modern comfort. Situated on a spacious 0.38 acre fenced homesite, this exceptional property features 2,795 square feet of living space and 4,163 total square feet, providing plenty of room to live, work, and entertain. From the moment you arrive, you will appreciate the peaceful setting and inviting curb appeal that make Oakdale Street one of the town’s most desirable locations. Inside, thoughtful craftsmanship is evident throughout with custom trim work, rich stone and wood flooring, double pane windows and doors, and a warm family room centered around a natural gas fireplace. The well appointed kitchen features a natural gas range, while the expansive air conditioned Florida room offers the perfect place to relax year round as you overlook the private backyard. Car enthusiasts, hobbyists, and those needing extra space will love the 4 car garage along with the detached air conditioned building, ideal as a home office, fitness studio, art studio, workshop, guest retreat, or whatever your heart desires. Recent improvements provide peace of mind, including: Roof replaced in 2019, newer HVAC system and water heater (4 years old) and a newer well pump (9 months old). Living in the Town of Windermere is more than owning a home, it’s embracing a lifestyle. Enjoy the beloved weekly farmers market, monthly food truck nights, festive holiday celebrations, and a charming downtown just a short walk away featuring a new Italian restaurant, breakfast café, coffee shop, wine bar, tennis courts, and more. Residents also enjoy exclusive access to community boat ramps on both Lake Butler and Lake Bessie, making it easy to experience the renowned Butler Chain of Lakes. If you have been searching for a home that offers character, generous space, exceptional flexibility, and one of Central Florida’s most treasured small town lifestyles, this is an opportunity you won’t want to miss. Be sure to click on the virtual tour links.

725 Oakdale Street, Windermere

3 Beds ⋅ 2 Baths ⋅ Isle Catalina SubDv. ⋅ 32805 Zip Code

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

4 Beds ⋅ 3 Baths ⋅ Windermere Downs SubDv. ⋅ 34786 Zip Code

Nestled within the highly sought-after Windermere Downs community this Lake-Access Residence, sitting on .74 acres, offers the ultimate Florida lifestyle surrounded by canopy-shaded, oak tree-lined streets. A walkway lined with custom pavers leads to the front door, where you're welcomed by the formal living and dining rooms on the right. Large bay windows let in plenty of natural light, creating a bright and inviting space. A barn door opens to the kitchen, which features travertine flooring, a gas stove, and stainless steel appliances—great for home cooking or entertaining. The living room is a cozy gathering space, with three skylights bringing in extra light and an Authentic Old Chicago Brick fireplace that adds warmth and character. The primary bedroom is spacious, with French doors that open to the screened-in pool lanai, offering easy access to outdoor living. The primary bathroom includes a Kohler clawfoot tub and Kohler fixtures, adding a touch of quality and comfort. Out back, the screened-in pool with travertine deck and patio provides a great spot to relax, while the larger open travertine patio off of the kitchen is perfect for hosting family and friends. The backyard is full of greenery, offering both beauty and privacy and an irrigation well. Home includes a 1,000 Underground Large Gas Tank and Full House Propane Generator and a hybrid water heater. A two-car attached garage is complemented by a large detached deep second two-car garage, perfect for extra parking, storage, or keeping your favorite lake-living toys. Living in Windermere Downs means access to a private community boat ramp, where you can launch your boat and explore Lake Down and the Butler Chain of Lakes. The community amenities include a dock with a roped-off swim area, tennis courts, pickleball courts, community park, playground—plenty of options for outdoor fun. Recent updates include whole house re-pipe (2026), freshly painted exterior and new soffit (2026).

2009 Woody Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Davis Shores SubDv. ⋅ 34786 Zip Code

Welcome to 20 Oakdale Street, an exceptional waterfront luxury residence in the highly sought-after Town of Windermere with direct access to Lake Down and the Butler Chain of Lakes offering an ideal blend of elegance, privacy, and Florida lifestyle, this beautiful home is perfectly positioned to enjoy the area's charming small-town atmosphere while remaining just minutes from world-class dining, shopping, golf, and attractions * Incredible backyard * Summer Kitchen with Pizza Oven * Firepit with Stone Seating * Boathouse * Viking 6 Burner Gas Cooktop * Viking Fridge * Built in 2004 * 2 Suites on 1st Floor * Step inside to discover spacious living areas filled with natural light, soaring ceilings, and thoughtfully designed spaces perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into inviting gathering spaces, while the generous bedrooms provide comfort and privacy for family and guests. * Outside, enjoy your own private retreat with beautifully landscaped grounds, ample outdoor living space, and the opportunity to experience everything that makes Windermere one of Central Florida's most desirable communities. Whether relaxing by the pool, hosting friends, or taking advantage of nearby lakes and recreation, this home offers the lifestyle you've been searching for. * Located within close proximity to top-rated schools, renowned golf courses, the Butler Chain of Lakes, and just a short drive to downtown Orlando and major theme parks, this is a rare opportunity to own a premier property in one of Florida's most coveted addresses.

20 Oakdale Street, Windermere

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

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

4 Beds ⋅ 5 Baths ⋅ Lake Nona Estates SubDv. ⋅ 32827 Zip Code

Nestled within the exclusive gated enclave of Lake Nona Golf & Country Club, 10348 Kensington Shore Drive presents a rare 2022-built modern masterpiece that redefines sophisticated living. As you enter, your eye is immediately drawn to the exquisite marble flooring that flows throughout the 3,964 square feet, complemented by custom warm lighting that bathes every room in an elegant glow. The gourmet kitchen serves as the heart of the home, boasting an oversized waterfall island, premium stone countertops, and extensive custom cabinetry — an entertainer’s dream perfectly suited for intimate family dinners or grand gatherings. This seamless open-concept design flows into sophisticated living spaces, where a sleek electric fireplace creates an intimate ambiance. Expansive sliding glass doors invite abundant natural light and effortlessly connect the indoors to the breathtaking outdoor sanctuary. Each of the four generously proportioned bedrooms features its own luxurious en-suite bath. The main-level primary suite is an exceptional private retreat, complete with a spa-like bathroom, oversized walk-in closet, and private laundry. An upstairs loft provides versatile space for a refined home office, media room, or additional gathering area. Discerning details abound, including a sophisticated smart home system, dual upgraded refrigerators, dual dishwashers, dual washers and dryers, and designer ceiling fans throughout. The private quarter-acre lot offers unparalleled tranquility, overlooking two serene ponds with no rear neighbors. This resort-style backyard oasis features a heated pool and spa, a fully equipped screened outdoor kitchen, two custom fire pits, an elegant outdoor fireplace, and meticulously landscaped gardens — creating the ultimate setting for both intimate evenings and unforgettable entertaining. Situated in the community’s most desirable walkable location, residents enjoy effortless access to the championship golf course, resort-style pool, world-class fitness center, tennis and pickleball courts, and the exclusive clubhouse with fine dining. This premier gated community provides 24/7 manned security, round-the-clock concierge services, and a secure, family-oriented lifestyle where children can safely explore by foot or golf cart. This is Lake Nona living at its absolute finest! Ready to experience this exceptional home? Let’s schedule your private tour today.

10348 Kensington Shore Drive, Orlando

5 Beds ⋅ 5 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

Pre-Construction. To be built. Positioned along the coveted Butler Chain of Lakes, this waterfront residence offers an exceptional opportunity to live in the Town of Windermere. Boasting approximately 85 feet of private frontage, The property captures sweeping views across Wauseon Bay. Permits have been approved including a 900 sf covered boat dock with lift. There are 2 primary suites, one on the 1st floor and one on the 2nd that open to a private balcony and patio respectively overlooking the water creating a serene retreat. All secondary bedrooms have lake views and balconies. Open floor plan with 2 story great room and massive windows throughout. Just moments from Windermere’s parks, tennis courts, farmers market, and private boat ramp, this home embodies the charm and lifestyle of lakefront living in one of Central Florida’s most desirable communities. ** Also listed as vacant land MLS S5147532 for $1,650,000

212 W 1st Avenue, Windermere

4 Beds ⋅ 3 Baths ⋅ Almond Tree Estates SubDv. ⋅ 32835 Zip Code

Experience the best of Central Florida living in this **stunning waterfront pool home**, where serene views and thoughtful upgrades create the perfect private retreat. From the moment you enter through elegant double French doors, you’re welcomed by breathtaking sightlines that extend from the formal living room across the screened lanai and sparkling pool to a tranquil, spring-fed pond—ideal for birdwatching, fishing, and everyday relaxation. This spacious 4-bedroom, 3-bath residence offers a versatile and well-designed layout with both formal and casual living areas. The family room features soaring vaulted ceilings and a cozy wood-burning fireplace, creating a warm and inviting atmosphere for gatherings. The beautifully renovated kitchen (2026) showcases brand-new appliances, Uba Tuba granite countertops, ample cabinetry, and an open design that seamlessly connects to the living spaces while overlooking the pool and water views. Throughout the home, you’ll appreciate the value of **major upgrades that provide true peace of mind**, including a brand-new A/C (Sept 2025) for energy efficiency, a full home repipe completed in 2019, a newer water heater (Aug 2020), and fully remodeled bathrooms (2025) with modern finishes—along with the completely upgraded kitchen featuring all new appliances (2026), offering both style and functionality. The primary suite is a true sanctuary, offering direct access to the pool, peaceful waterfront views, a large walk-in closet, and a spa-inspired bathroom with dual vanities, a garden tub, and a separate shower. The fourth bedroom is perfectly suited as a home office or guest suite, enhanced by calming fountain views. Step outside to your private, screened lanai—pre-wired for cable and designed for year-round enjoyment, whether hosting guests or unwinding in your own tropical setting. Additional features include an interior laundry room with washer, dryer, and utility sink, plus a convenient pool-access guest bathroom. Combining **breathtaking water views, modern upgrades, and exceptional indoor-outdoor living**, this move-in ready home is a rare opportunity to own a true Florida paradise. Don’t miss it!

1125 Almond Tree Circle, Orlando

2 Beds ⋅ 2 Baths ⋅ West Cove Condo SubDv. ⋅ 32751 Zip Code

TURN KEY AND RENOVATED IN SOUGHT-AFTER WEST COVE!! Wake up to breathtaking sunrises with a stunning, unobstructed view stretching across Lake Maitland—the largest lake in the highly sought-after Winter Park Chain of Lakes—from this beautifully renovated, truly turnkey condominium. All flooring, bathrooms, fixtures, paint, AC, water heater, sliding door to balcony, kitchen/appliances, and closet systems have been painstakingly updated to the highest level, making for an unparalleled opportunity to simply move right in and begin enjoying immersive lake views. The primary suite has been reimagined and has its own ensuite bath and a new built-in closet with copious storage, complete with signature views of Lake Maitland. This spacious residence offers an ideal central location, just moments from an array of dining options, Lake Lily Park, Enzian Theater, and convenient access to Interstate 4 via Lee Road or Maitland Boulevard. The monthly association fee—lower than most lakefront communities—provides exceptional value and includes access to lakefront docks (with boat slips available on a first-come basis), a fitness center, an inviting lobby for entertaining, a heated pool and spa, a grilling area with seating, storage for canoes, kayaks, and paddleboards, assigned and guest parking, laundry facilities on every floor, Spectrum cable and internet, as well as water, sewer, and trash services. This property may be under audio/visual surveillance.

1100 S Orlando Avenue Unit 306, Maitland

3 Beds ⋅ 2 Baths ⋅ Isle Catalina SubDv. ⋅ 32805 Zip Code

FINALLY…..The WOW factor you’ve been searching for! WATERFRONT! METAL ROOF! NEW A/C! NEW KITCHEN! Walk into light, bright and open thanks to a brand new kitchen featuring stainless steel appliances, slow-close cabinets, quartz counters, a snack bar, a copper sink, bonus cabinets ready for your coffee or wine bar. Continue back into the formal dining room featuring coffered ceilings and then back again to the best part….the bonus room. Tons of windows bring the outside in with a view of the 80 feet of water frontage. The home’s primary bedroom includes an en suite bathroom with a spacious shower offering bench seating and a rainfall bonus shower head. The hall bathroom’s tub and shower are reglazed. There is also a new vanity, mirror and light fixture. Out back, take your boat, kayak, canoe or paddleboard directly to Clear Lake, a 357 square foot, freshwater lake known for wakeboarding, skiing, and fishing. The optional HOA provides residents with a sand volleyball court, lake house for rent for parties, picnic tables, pavilion, BBQ grills, and a private boat launch ramp. This is truly a hidden gem in downtown Orlando! Easy access to all of the best of central Florida: theme parks, beaches, restaurants, shopping and more!

2801 Gulfstream Road, Orlando

3 Beds ⋅ 3 Baths ⋅ Hacindas Bon Del Pinos SubDv. ⋅ 32757 Zip Code

Envision the arrival of your private lakefront estate on the storied shores of Lake Beauclair with direct access to Lake Dora, the crown jewel of the Harris Chain of Lakes, a vast and celebrated waterway offering endless miles of lock and river cruising for days defined by leisure and adventure. Life on the lake unfolds at a gentler, more inspired pace as mornings begin with coffee on the dock while mist rises from the water, afternoons invite boating, paddleboarding and fishing along scenic shorelines, and evenings conclude with unforgettable sunset cruises beneath painted skies. Just moments away, the charm of Mount Dora enriches the lifestyle even further. Known for its storybook streets, vibrant arts scene and year-round calendar of festivals, residents enjoy boutique shopping, waterfront dining, antique markets, boat shows, food and wine celebrations, and lively community gatherings that make every season feel like an occasion. Across a remarkable eight-acre parcel, 6136 Dora Drive commands hundreds of feet of pristine shoreline, ideally oriented to the west for breathtaking sunset vistas that paint the water in gold each evening. This extraordinary canvas invites limitless possibilities such as design a grand equestrian compound, cultivate a private orchard, create an inspired guest residence with an expansive collector’s garage or explore opportunity to thoughtfully subdivide. Within a canopy of mature trees, a sprawling single-story residence spans approximately 4,000 square feet under roof, offering three bedrooms, two and a half baths, walls of windows, a screened pool and spa, and a newer tile roof. Completing this rare offering is an enclosed boathouse with private doors, an increasingly scarce luxury along the chain. With no HOA restrictions and boundless space to create, this is a legacy lakefront setting where vision meets lifestyle, a place where lake days, sunset evenings and timeless charm of Mount Dora define life at its most exceptional.

6136 Dora Drive, Mount Dora

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