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 ⋅ 2 Baths ⋅ Marsh Sub SubDv. ⋅ 34786 Zip Code

Professional Pics Coming Soon - They say Good Things Come in Small Packages & This Proves It * Must see this Gem to really appreciate the craftsmanship and attention to detail throughout * Completely renovated in 2020 & 2023, this exceptional Windermere property seamlessly blends timeless character with modern luxury, offering thoughtfully designed spaces, quality finishes, and an impressive level of care in every detail. From the beautifully appointed kitchen featuring Kitchenaid Fridge, Miele Dishwasher, Sub Zero Gas Range, to the versatile in-law apartment with Sub Zero Double Drawer Fridge, every aspect of this home has been designed for comfort, functionality, and effortless Florida living * Everything was improved, the Roof, AO Smith Water Heater, Septic, A/C, Hardwood Flooring, Tile * Fireplace * Natural Gas * 1 Block from the Boat Ramp to Lake Butler and the Chain of Lakes * Downtown Windermere offers many fun events and the New Frescos Italian Restaurant, Dixie Cafe' and the Windermere Brewery are just a few places you can walk to get a great meal * Mature Landscaping and Oak Trees * 2 Covered Carports for Boat or Auto * Storage Shed with Electric provides ample room for a workshop * Book your Private Tour Now

611 Butler Street, Windermere

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

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

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 ⋅ Jewel Shores SubDv. ⋅ 32806 Zip Code

Spacious South Orlando Home with Great Location & Opportunity Great South Orlando location, spacious floor plan, excellent schools, and plenty of room to make this home your own! 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

2 Beds ⋅ 2 Baths ⋅ Fairview Vista Condo Ph 02 SubDv. ⋅ 32804 Zip Code

Enjoy lakefront living in this beautifully positioned third-floor condo overlooking Lake Fairview! Just north of Orlando’s Packing District and minutes from College Park and Downtown Orlando, this home offers peaceful views with convenient city access. The interior features a brand new AC system, tall ceilings, spacious primary suite with an en-suite bath, walk-in closet, and direct access to the screened balcony overlooking the lake. Community amenities include a pool, tennis court, lakefront beach, grills, clubhouse, private boat ramp, and boat/trailer parking, subject to availability. Covered parking and elevator access add convenience. HOA dues include 1G high-speed internet, hundreds of TV channels, and cloud DVR. Don’t miss this opportunity to enjoy comfortable lakefront living in a desirable Orlando community!

4109 Fairview Vista Point Unit 315, Orlando

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

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

Brand New Roof being installed this Week! 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

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 ⋅ 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

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