Windermere, FL Real Estate | Windermere, FL Properties between $3,000,000 and $4,000,000 for Sale

4 Beds ⋅ 6 Baths ⋅ Acreage SubDv. ⋅ 34786 Zip Code

Finding a MODERN, CUSTOM-BUILT LAKEFRONT HOME in Windermere, set on 1.15 ACRES with NO HOA or CDD, is an increasingly rare opportunity. Add exceptional PRIVACY, your own PRIVATE BOAT DOCK with TWO BOAT LIFTS, extensive high-end upgrades and beautiful lake views, and this home truly stands apart. Offering approximately 4,200 square feet of thoughtfully designed living space, this striking contemporary residence combines luxurious finishes with an effortless indoor-outdoor lifestyle, all within minutes of Windermere's everyday conveniences. From the moment you enter, the home's clean architectural lines, expansive windows and natural light create an immediate sense of space and connection to the outdoors. Beautiful PORCELAIN TILE flooring flows throughout the main level, while warm WOOD FLOORING upstairs complements the modern design. At the heart of the home is a stunning GOURMET KITCHEN featuring contrasting granite countertops, extensive CUSTOM BLUM BIRCH CABINETRY with premium aluminum detailing, and an impressive suite of WOLF APPLIANCES, including a six-burner gas range top, convection steam oven, dual-fan convection oven and warming oven. A built-in coffee station, generous pantry storage and cleverly concealed cabinetry complete this exceptional space. The adjoining living area is anchored by a dramatic 72-INCH GAS FIREPLACE, creating an inviting setting for both everyday living and entertaining. The MAIN-FLOOR PRIMARY SUITE is a peaceful retreat, with large windows framing beautiful lake views and direct access to the lanai. Two separate custom-fitted walk-in closets provide exceptional storage, while the luxurious en-suite bathroom features a freestanding soaking tub, separate oversized shower, dual vanities and elegant FLOOR-TO-CEILING PORCELAIN TILE. Upstairs, THREE ADDITIONAL EN-SUITE BEDROOMS provide excellent privacy and comfort for family and guests. The expansive LOFT area offers an additional living and entertaining space, complete with a fitted kitchenette, granite countertops and wine cooler. Multiple oversized patio doors open onto both a front balcony and a generous REAR TERRACE OVERLOOKING THE LAKE, creating a wonderful setting for morning coffee, evening drinks or simply enjoying the peaceful surroundings. Outside, the lifestyle is every bit as impressive. Approximately 80 FEET OF LAKEFRONT, a PRIVATE DOCK WITH TWO BOAT LIFTS and a beautifully secluded setting create your own waterfront escape. The spacious LANAI features MOTORIZED SCREENS, allowing indoor and outdoor living to flow seamlessly together. There's also ample room to create a spectacular POOL AND OUTDOOR ENTERTAINING AREA if desired. And as the sun goes down, enjoy views of the DISNEY FIREWORKS illuminating the evening sky. Beyond its beautiful design, this home has been built and equipped with exceptional attention to quality, comfort and efficiency. Notable features include IMPACT INSULATED WINDOWS AND DOORS, enhanced interior insulation, a WHOLE-HOUSE NATURAL GAS GENERATOR, TWO RINNAI TANKLESS WATER HEATERS, motorized window shades, extensive custom storage and a THREE-CAR GARAGE with insulated doors and RHINO garage storge shelves. The generous homesite also offers potential for future expansion. Perfectly positioned in WINDERMERE, the property offers a rare combination of PRIVACY, WATERFRONT LIVING and everyday convenience, with easy access to shopping, dining, schools, major roadways and Orlando's world-famous attractions.

12620 S Lake Sawyer Lane, Windermere

$3,150,000

4 Beds ⋅ 5 Baths ⋅ 34786 Zip Code

ONE-STORY, NEW CONSTRUCTION, MODERN FARMHOUSE ELEGANCE ON 1.3 PRIVATE ACRES IN WINDERMERE. Experience an unparalleled synthesis of modern luxury and tranquil, natural beauty. This remarkable custom estate, expertly crafted by Hanson Custom Homes, presents a rare opportunity in a secluded Windermere setting. Flanked by three mature oaks trees at the entrance this generous 1.3-acres of land offers a picturesque retreat from the hustle and bustle of the city while remaining conveniently close to urban amenities. Upon approach, you are immediately impressed by the home's striking modern farmhouse aesthetic. The architecture seamlessly blends classic board-and-batten siding with contemporary clean lines. The expansive, single-story residence is designed to make a statement, centered around a private courtyard that features rich, natural wood-framed doors and a matching header that creates a warm and inviting entrance. The Hawksnest design is expertly focused on maximizing natural Florida views throughout the entire property. Backing up to a dedicated conservation area, the home offers the ultimate in privacy, framed by mature native trees and lush vegetation. This private courtyard not only serves as a welcoming entrance but also provides convenient, private access to the home office. The meticulously planned interior includes custom kitchen cabinetry and unique design features that are perfect for entertaining friends and family. The chef’s kitchen blends modern organic design with high-end functionality. Floor-to-ceiling custom warm wood cabinetry creates a seamless aesthetic, integrating panel-ready 30" Thermador refrigerator and freezer units alongside built-in pantry storage. A premium 48" six-burner range takes center stage beneath a custom plastered range hood, complemented by a wall-mounted brass pot filler and sleek vertical sconce lighting embedded directly in the full-height quartzite backsplash. Thick, mitered-edge Taj Mahal quartzite countertops stretch across the perimeter and onto an expansive center island, which comfortably accommodates five counter stools. Walk-in pantry offers a secondary refrigerator, tons of additional storage and hidden Thermador microwave. A sophisticated split floor plan ensures the primary suite remains private and separate from the other bedrooms. This primary bedroom boasts a very large walk-in closet with custom lighted cabinetry and a master bath filled with natural light from large windows and an overhead skylight. With 4 Bedrooms, 4 Full Baths, 1 Half bath, and additional dedicated spaces for a Exercise/Theater Room, Office, and Game Room, this home offers endless versatility. The property also features a oversized pool with spa and an oversized 3-Car Garage. Located just a five-minute drive from downtown Windermere or Winter Garden Village, you are perfectly situated to major highways, shopping, employment centers, and Orlando's major theme parks.

1815 Windermere Road, Windermere

9310 Isleworth Gardens Drive, Windermere

$3,595,000

3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pantry. A stone fireplace provides a focal point in the living room, while the spacious family room opens through panoramic sliding doors to a covered lanai, extending the living spaces naturally outdoors.The primary suite offers a private retreat with a morning bar, sitting area, spa-inspired bath and generous walk-in closet. A wood-floored study with custom built-ins provides an elegant setting for work, while additional bedrooms offer comfort and privacy for family and guests. Additional interior highlights include the laundry room, powder bath, and a three-car garage.Beyond the interiors, the home embraces its lush garden setting with tranquil pond views and an expansive outdoor living area. The covered lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa, creating a private setting for relaxed afternoons and beautiful entertaining. The Gardens of Isleworth offer convenient living in a beautiful setting within Central Florida’s most iconic golf course community.

9310 Isleworth Gardens Drive, Windermere

$3,999,000

5 Beds ⋅ 6 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 17th fairway of The Golden Bear Club. Fully renovated, architecturally refined and intentionally designed by Ashley Martin Home. From the moment you enter, an inviting foyer opens to a spacious living room framed by 12-foot ceilings, expansive windows, and views of the course, filling the home with natural light and warmth, as well as a functional dining room with built-in cabinetry, perfect for entertaining. Designed with both elegance and functionality in mind, the home features wide-plank hardwood flooring throughout, custom drapery and shades, and extensive upgraded lighting and finishes. The private office is a standout, complete with rich built-in cabinetry and a wood-accent ceiling that creates a sophisticated workspace. The primary suite is a true retreat, accessed through a private vestibule-style entrance offering a serene escape. Inside, enjoy access to the outdoors, a spa-inspired bath with a freestanding tub, an oversized walk-in shower, and a spacious custom walk-in closet with built-ins. The chef’s kitchen is thoughtfully appointed with built-in refrigeration and dishwasher, an appliance garage, a large center island, Butler’s pantry with wine refrigeration, and a generous breakfast nook. A mud area with built-ins adds everyday convenience, while the family room showcases custom built-ins for effortless living. The home offers a versatile and spacious layout, including two ensuite bedrooms with walk-in closets on the main level, and two additional bedrooms upstairs connected by a shared bath. The second floor also features a loft with built-ins that can easily function as a fifth bedroom, playroom or media room, along with a bonus space overlooking the golf course—currently used as a gym, but ideal for a game room or lounge. Outdoor living is equally impressive, featuring a saltwater pool and spa, fire pit, cabana with summer kitchen, and a private putting green. The fenced yard and retractable screened lanai create a seamless indoor-outdoor experience, while a convenient exterior-access half bath serves the pool area. Additional highlights include a well-appointed laundry room with stacked washer and dryer, and a four-car garage with high ceilings and custom flooring, and much more! This turn-key home can be purchased fully furnished and decorated. Conveniently located to shopping, dining, expressways, tourist attractions, and top-rated public and private schools, this is a rare opportunity to own a meticulously designed, luxury estate that blends comfort, style, location, and stunning golf course views into one extraordinary residence.

6120 Greatwater Drive, Windermere

$3,250,000

3 Beds ⋅ 4 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Welcome to 6126 Payne Stewart Drive, a beautifully renovated golf villa in Isleworth, just steps from the club house. This 2,848-square-foot home offers three bedrooms, each with its own full bathroom, plus a powder room for guests. Soaring ceilings and an open floor plan bring a sense of space to the main living areas, where travertine floors and new doors complement the recent renovations. The gourmet kitchen features a 10-ft center island and top of the line appliances. The primary suite includes a recently renovated bathroom with a generously sized shower and soaking tub. Outside, a fully fenced garden setting surrounds the pool and spa. A summer kitchen and fireplace make the space inviting for outdoor dining and relaxing in the Florida Sunshine.

6126 Payne Stewart Drive, Windermere

$3,290,000

5 Beds ⋅ 7 Baths ⋅ Casabella SubDv. ⋅ 34786 Zip Code

Welcome to an exceptional luxury residence in the prestigious gated community of Casabella in Windermere. Set on a private 0.71-acre homesite, this stunning Toll Brothers residence offers approximately 5,502 square feet of beautifully appointed living space, featuring 5 private ensuite bedrooms and 2 half bathrooms. From the moment you enter, the home impresses with sophisticated architectural details, soaring ceilings, abundant natural light, and expansive spaces thoughtfully designed for both refined everyday living and effortless entertaining. The gourmet kitchen is equipped with premium appliances, custom cabinetry, an oversized island, ample counter space, and an open-concept design that flows seamlessly into the family room and dining areas. The first-floor primary suite offers a tranquil private retreat, complete with a spa-inspired bathroom featuring dual vanities, a spacious walk-in shower, and generous his-and-her closet areas. Also located on the first floor is an additional private suite and a dedicated office, while the second floor offers the remaining bedrooms, a secondary primary suite, a spacious loft, and versatile living areas. Step outside to an impressive outdoor living space featuring a private heated in-ground pool, upgraded covered lanai with a summer kitchen, and beautifully landscaped surroundings, creating an ideal setting for entertaining or relaxing in complete privacy. Additional features include a three-car garage, tile roof, elegant finishes, abundant storage, and carefully curated furnishings throughout. Offered fully furnished, this exceptional residence presents a rare opportunity to enjoy a turnkey Windermere lifestyle within one of Central Florida’s sought-after gated communities. Ideally positioned near premier shopping, fine dining, golf, entertainment, major roadways, and world-renowned attractions, this Casabella estate brings together luxury, privacy, comfort, and convenience.

4243 Isabella Circle, 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

5050 Isleworth Country Club Drive, Windermere

$3,189,000

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

$3,580,000

5 Beds ⋅ 7 Baths ⋅ Casabella SubDv. ⋅ 34786 Zip Code

Welcome to 4302 Isabella Circle, an exceptional 5-bedroom, 6.5-bath residence offering 5,362 square feet of living space on an expansive 0.88-acre homesite within the gated Casabella community of Windermere. Offered completely furnished, this Spanish-inspired home combines generous interior living spaces with an impressive outdoor setting and water views. Inside, soaring ceilings, hardwood flooring and an expansive living area with a full wet bar create an inviting environment for both everyday living and entertaining. The open-concept gourmet kitchen features granite countertops, KitchenAid stainless-steel appliances and a gas range. The spacious first-floor primary suite offers abundant closet space and a well-appointed en suite bath, while a secondary primary suite is located upstairs along with three additional en-suite bedrooms. The fully fenced backyard is a true extension of the home, featuring an infinity-edge pool, spa, firepit, multiple lounge areas and a glass-enclosed lanai with a full summer kitchen featuring Viking appliances and a dedicated dining area. The oversized homesite provides exceptional outdoor space while maintaining beautiful water views. Additional features include a study/office with built-ins, a converted garage space currently utilized as a media/game room with the ability to be converted back, and a fully paid-off solar panel system with no remaining lease obligation. Conveniently located near shopping, dining, schools and the many amenities of the Windermere area. The combination of nearly an acre of land, extensive outdoor entertaining areas, water views, furnishings and owned solar makes 4302 Isabella Circle a distinctive offering in Casabella.

4302 Isabella Cir, Windermere

$3,599,000

5 Beds ⋅ 7 Baths ⋅ Casabella Ph 2 SubDv. ⋅ 34786 Zip Code

EXCEPTIONAL LAKEFRONT LUXURY ESTATE IN CASABELLA AT WINDERMERE Discover an extraordinary luxury residence in the prestigious gated community of Casabella at Windermere, where elegant architecture, exceptional outdoor living, and one of the community’s most desirable lots come together. The true highlight of this property is its exceptional waterfront setting. The lake beautifully surrounds the rear of the home, pool, and outdoor living areas, creating a rare sense of privacy and tranquility. From the expansive covered lanai and upper-level balcony, enjoy breathtaking water views and a peaceful backdrop that makes this property truly special. Featuring two spacious levels and soaring ceilings, this magnificent home offers approximately 5,073 square feet of luxurious living space with 5 bedrooms, all featuring private en-suite bathrooms and walk-in closets. The primary suite is conveniently located on the first floor and offers a spa-inspired bathroom, large windows, and a serene connection to the outdoor surroundings. The gourmet kitchen combines functionality and elegance with modern wood cabinetry, stainless steel appliances, and generous counter space, creating an inviting space for both everyday living and entertaining. The open living areas feature impressive proportions and abundant natural light, perfectly complementing the home's sophisticated Mediterranean-inspired architecture. Step outside to your private resort-style retreat. The expansive outdoor living area features a private pool, heated spa, and spacious gourmet summer kitchen, creating the perfect setting for entertaining guests or enjoying relaxing evenings overlooking the lake. From the elegant façade and impressive two-story design to the spectacular waterfront setting and exceptional outdoor living spaces, this residence offers a rare combination of luxury, privacy, and breathtaking views. Located in Casabella at Windermere, a prestigious gated community known for its spacious homesites and elegant residences, the property is conveniently located near premier shopping, dining, top-rated schools, major roadways, and Orlando’s world-famous attractions. A truly remarkable opportunity to own a one-of-a-kind luxury estate in one of Windermere’s most desirable communities.

3986 Isabella Circle, Windermere

$3,990,000

6 Beds ⋅ 7 Baths ⋅ Casabella SubDv. ⋅ 34786 Zip Code

Welcome to this beautifully furnished luxury residence in the guard-gated community of Casabella in Windermere. Situated on a private half-acre homesite, this impressive Toll Brothers Villa Divina model offers approximately 6,881 square feet of thoughtfully designed living space featuring 6 bedrooms, and 7 full bathrooms. The home showcases elegant architectural details, soaring ceilings, abundant natural light, and expansive living areas designed for both everyday comfort and entertaining. The gourmet kitchen features premium appliances, custom cabinetry, an oversized island, generous workspace, and a seamless connection to the family room and dining areas. The first-floor primary suite provides a private retreat with a spa-inspired bathroom featuring dual vanities, a walk-in shower, and spacious closet areas. Additional bedrooms, a second-floor media room, loft, office, and flexible living spaces provide exceptional versatility. The outdoor living area features a private in-ground pool, covered lanai, and beautifully landscaped surroundings. Additional highlights include a three-car garage, tile roof, refined finishes, abundant storage, and carefully selected furnishings throughout. Offered fully furnished, this residence provides a seamless opportunity to enjoy Windermere living in one of Central Florida’s desirable gated communities. Conveniently located near premier shopping, dining, golf, entertainment, major roadways, and area attractions, this Casabella estate combines elegance, comfort, and convenience.

4201 Isabella Circle, Windermere

$3,500,000

4 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Welcome to the exclusive gates of Isleworth, golf front estate offers over 7,600 square feet of refined luxury living overlooking the fairway of the renowned Isleworth Golf & Country Club, one of the worlds most prestigious golf club communities, this championship course was designed by Arnold Palmer and set along the Butler Chain of Lakes. The neighborhood is defined by beautifully landscaped scenery, sweeping water views, and exceptional 24 hour guard gated privacy. This estate offers exceptional potential supporting four beds, six baths, a private office, inside gym, approached by a private driveway with ample guest parking and a 4 car garage. The two story residence opens with a regal marble foyer and fountain feature. Inside, vaulted ceilings, skylights, and wall to wall sliding glass doors fill the main living areas with natural light while framing views of the pool, sauna, golf views and rolling fairways beyond. A grand fireplace and wet bar create an inviting space for entertaining. The chef’s kitchen centers on a dramatic island and is highlighted by a striking copper range hood, warm cabinetry, and an open eat in layout designed for both everyday living and hosting. Above the garage, a private accessory dwelling unit provides flexible secondary living space or maids living. Each of the spacious bedrooms offers its own view and is finished with marble baths. A dedicated home gym adds further convenience. Exceptional amenities and sophisticated living in the world renowned community of Isleworth.

5524 Worsham Court, Windermere

$3,400,000

6 Beds ⋅ 7 Baths ⋅ 34786 Zip Code

Spectacular Private Lakefront Estate on Lake Olivia, Windermere Near The Grove Shops & Restaurants. Enter through custom Iron gates to this extraordinary Mediterranean estate set on 1.75 private acres along the shores of Lake Olivia. Featuring six bedrooms, all with ensuite baths, this exceptional home offers nearly 6,000 square feet of living space, mature landscaping, and no HOA. Ideal for multigenerational living, the attached one-bedroom in-law apartment features a private entrance, full kitchen, living area, and ensuite bedroom—perfect for extended family or guests. The chef’s kitchen is a showstopper, featuring double islands, granite countertops, a professional Wolf gas range with double ovens, a 48-inch Sub-Zero refrigerator/freezer, a wine fridge, and a butler’s pantry. Elegant finishes, formal living and dining rooms, and a private upstairs media/game room complete the interior. Enjoy Florida living in the expansive 1,200+ sq. ft. screened lanai with remote hurricane shutters, summer kitchen, stone fireplace, and a stunning lagoon-style saltwater pool with heart-shaped spa. The luxurious primary suite offers French doors overlooking the pool and lake, custom closets, and a spa-inspired bath. Boating enthusiasts will love the oversized boathouse, screened dock room, motorized boat lift, and direct access to Lake Olivia, a private spring-fed lake with no public access, ideal for boating, waterskiing, and fishing. Over $200,000 in recent enhancements include a whole-house generator, new A/C system, updated lighting and ceiling fans, remote hurricane shutters, Leaf Guard gutters, roof tile servicing and sealing, new side pavers, and fresh interior paint. A rare opportunity to enjoy privacy, luxury, and true multigenerational living on one of Central Florida’s most desirable private lakes. Convenient to shopping, major highways, and area attractions. Move-in ready! 360° virtual tour and floor plan available. Seller may consider a Lease Purchase Option.

9679 Westover Roberts Rd, Windermere

$3,100,000

Chaine Du Lac SubDv. ⋅ 34786 Zip Code

Set behind the gates of Chaine Du Lac, one of Windermere's most exclusive lakefront enclaves, this exceptional nearly one acre high and dry homesite presents a truly rare opportunity to create a legacy estate on the coveted Butler Chain of Lakes. Offering an expansive, level homesite with an extraordinary 200 feet of direct frontage on the western shores of Lake Butler, this is one of the finest remaining parcels of its kind. Beyond the shoreline, the Butler Chain of Lakes offers an unmatched lifestyle of boating, watersports, paddleboarding, and fishing, all accessible directly from your private backyard. From sunrise reflections across the water to unforgettable Florida sunsets, every day is defined by the serenity and elegance of lakefront living. More than a homesite, this is an invitation to create a waterfront estate in one of Windermere's most coveted addresses—where extraordinary design, an iconic setting, and an unparalleled lakefront lifestyle come together in a way that is rarely available.

12624 Park Avenue, Windermere

5237 Isleworth Country Club Drive, Windermere

$3,600,000

5 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Located along the 2nd tee of Isleworth's renowned championship golf course, this beautiful golf-front estate offers an exceptional location within the gates. The five-bedroom home features offers a spacious and open floor plan of more than 5,900 square feet overlooking the serene golf and water vistas. .

5237 Isleworth Country Club Drive, Windermere

$3,100,000

4 Beds ⋅ 5 Baths ⋅ Casa Del Lago Rep SubDv. ⋅ 34786 Zip Code

Virtually Staged. Welcome to 12102 Montalcino Circle, an exceptional custom built waterfront estate located in one of Windermere's most sought after gated communities, Casa Del Lago. Perfectly positioned at the end of a quiet cul-de-sac on 1.41 acres along the shores of Lake Burden, this extraordinary residence is offered fully furnished and showcases breathtaking water views, nightly Disney fireworks from the backyard, and a private boat dock complete with water, electric, and a boat lift. Designed for year round enjoyment, the outdoor living space features a heated pool and spa, a covered summer kitchen with a built in grill, sink, refrigerator, and bar seating, along with a fire pit, creating the ultimate lakefront retreat from the moment you arrive. Inside, timeless craftsmanship and thoughtful design are showcased throughout. Just beyond the foyer, the formal dining room welcomes guests with a coffered ceiling and is complemented by a wet bar with a dedicated wine closet, creating an elegant setting for entertaining. Nearby, a private office or den offers a quiet retreat for work or relaxation. The spacious living room is highlighted by a matching coffered ceiling, a gas fireplace, and pocket sliding glass doors that disappear completely, creating a seamless transition between the indoor living areas and the outdoor entertaining spaces. The beautifully appointed kitchen blends style and function with granite countertops, stainless steel appliances, a natural gas cooktop, a tile backsplash, and a breakfast nook overlooking the pool and sparkling waters of Lake Burden. The first floor primary suite is a private sanctuary with breathtaking lake views and direct access to the lanai. The primary bath features separate vanities, a soaking tub, an oversized walk in shower with dual shower heads, and an expansive walk in closet. A second first floor bedroom with its own en suite bath, walk in closet, and peaceful pond views provides an ideal space for guests or multigenerational living. Upstairs, a generous bonus room serves as the perfect gathering space, complete with a fireplace, wet bar, and sliding glass doors that open to a private balcony overlooking Lake Burden. One upstairs bedroom features its own en suite bath, while the second is conveniently located just steps from a full bath, providing comfortable accommodations for family and guests. Perfectly positioned just minutes from downtown Windermere, Winter Garden Vineland Road, Restaurant Row, Walt Disney World, and Orlando International Airport, this remarkable estate offers an exceptional combination of privacy, luxury, and convenience.

12102 Montalcino Circle, Windermere

$3,000,000

5 Beds ⋅ 5 Baths ⋅ Lake Butler Estates SubDv. ⋅ 34786 Zip Code

Incredible 1st Floor Inlaw Apartment with Full Bath, Sitting Room with Fireplace & Bedroom with Large Walk in Closet * Purchase before October 31, 2026 and receive a full size Pickleball & Sport Court * Welcome to this spectacular 5-bedroom, 5-bathroom custom home offering over 8,000 square feet of thoughtfully designed luxury living—spared no expense and crafted to perfection. * Nestled on a sprawling acre-plus level lot, this residence redefines your Florida lifestyle with elegance and comfort. * Step inside to discover more than 5,000 heated square feet filled with spacious rooms adorned with wide plank wood flooring, tongue & groove ceilings, and exposed timber beams that create a warm, inviting atmosphere. * The impressive 1st floor primary suite features a huge closet offering ultimate storage and style. * The gourmet kitchen is a chef’s dream, having Natural Gas & equipped with high-end Thermador appliances and crowned by stunning quartz countertops—perfect for preparing meals or entertaining. * Step outside to the fully appointed summer kitchen and enjoy the screen-enclosed swimming pool on your expansive wrap-around porch, enhanced by elegant stacked stone columns. * Car enthusiasts and hobbyists will appreciate the oversized 42 x 30 - 4 car garage with 10-foot tall doors, providing ample space for all your toys and vehicles. * Additional modern comforts include natural gas for efficiency and convenience throughout the home. Laundry Rooms on each Floor * Located on the most sought-after street in Windermere, this masterpiece offers privacy, style, and unparalleled craftsmanship. Truly, this is everyone’s dream home—ready for you to create lasting memories.

11539 Lake Butler Boulevard, Windermere

$3,750,000

5 Beds ⋅ 6 Baths ⋅ Gotha Town SubDv. ⋅ 34786 Zip Code

Under Construction. Experience unparalleled luxury in this custom-built Davila Homes estate, ideally located in the heart of Windermere. Showcasing the highly sought-after Stanford floor plan, this magnificent residence offers approximately 6,182 square feet of living space with 5 bedrooms, 5 full baths, 1 half bath, and a spacious 3-car garage. Designed for both elegant entertaining and comfortable everyday living, the home features a grand foyer with soaring ceilings, expansive living and family rooms, a private study, and a spectacular gourmet kitchen with an oversized island, walk-in pantry, and premium finishes throughout. The luxurious first-floor owner's retreat serves as a private sanctuary with a spa-inspired bath, oversized walk-in closets, and direct access to the outdoor living areas. Upstairs, you'll find additional en-suite bedrooms surrounding a spacious loft and bonus room, providing the perfect space for family gatherings, a media room, or guest accommodations. Large covered lanais seamlessly blend indoor and outdoor living, creating an ideal setting for entertaining while enjoying Florida's year-round lifestyle. Situated in prestigious Windermere, this exceptional estate combines timeless architecture, thoughtful design, and superior craftsmanship, all within close proximity to top-rated schools, world-class golf, fine dining, shopping, and the Butler Chain of Lakes.

9960 6th Street, Windermere

$3,800,000

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the stunning 4th fairway of the renowned Isleworth Golf & Country Club, this exceptional single-story estate offers four bedrooms and more than 5,300 square feet of meticulously crafted living space. Every detail of this residence reflects the owner’s exceptional craftsmanship, with bespoke woodwork woven throughout the home, culminating in the crown jewel: the primary suite’s expansive wardrobe, featuring a central island, tiger wood floors, and cherry birch built-in displays—a true collector’s dream. The elegant foyer sets the tone, leading to formal living and dining spaces, and flowing effortlessly past a private office into the heart of the home: an open-concept kitchen, casual dining area, and family room designed for both entertaining and daily living. The gourmet kitchen is appointed with anigre wood cabinetry, a center island, dual sinks, a walk-in pantry, and professional appliances by Sub-Zero, Dacor, and Kitchenaid, marrying style and functionality in perfect harmony. A spacious game room with a wet bar provides an ideal space for recreation or hosting, while four luxurious bedrooms and 4.5 spa-inspired baths ensure comfort and privacy for family and guests alike. Seamlessly blending indoor and outdoor living, the estate features a sparkling open-air pool set against serene golf course vistas—an idyllic setting for year-round leisure and entertaining. Additional highlights include a circular driveway and motor court, a three-car garage, and a separate workshop. This is a rare opportunity to acquire a residence where world-class craftsmanship, refined design, and premier golf-front location converge, offering an unparalleled lifestyle in one of Central Florida’s most coveted enclaves.

5151 Latrobe Dr, Windermere

$3,200,000

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Discover the effortless blend of luxury, privacy, and modern design in this lovely Gardens of Isleworth villa. Featuring timeless elegance, this beautiful four-bedroom, four-bathroom custom villa, where every detail has been thoughtfully curated to create a refined sanctuary for everyday living and entertaining. Beyond the stately arched main entry door lies a secluded courtyard oasis—a private retreat centered around a sparkling pool, serene waterfall feature, and generous lounging areas. Whether basking in the sun or relaxing beneath the stars, this outdoor haven sets the tone for the extraordinary spaces within. Designed to embrace indoor-outdoor living, the oversized courtyard welcomes you with a seamless open-plan layout connecting the pool, summer kitchen, and a charming guest cabana. Perfect for hosting or escaping, the cabana offers a private retreat for guests or a peaceful haven for the homeowner. Inside the main residence, a sense of contemporary sophistication flows through the light-filled kitchen, elegant dining room—highlighted by a statement chandelier—and the spacious grand room. French doors throughout invite the outdoors in, offering lush views from nearly every space and extending the living area to multiple porches and verandas. The living room, centered around a calming fireplace, is the perfect spot to unwind after a long day, while the spa and cascading waterfall nearby add to the sensory appeal. Retreat to the expansive master suite, where a private porch overlooks vibrant greenery, offering a peaceful start and end to each day. Additional property highlights include a cozy morning room, a dedicated office with custom Burl wood built-ins, and a series of intimate outdoor and indoor spaces designed to inspire comfort and connection.

4819 Alexandra Garden Court, Windermere

$3,950,000

5 Beds ⋅ 8 Baths ⋅ Metcalf Park Rep SubDv. ⋅ 34786 Zip Code

Price Adjustment! Lakefront Living in the Heart of Windermere – A Rare Opportunity for Multigenerational Luxury Situated along the tranquil, open waters of Wauseon Bay—part of the world-renowned Butler Chain of Lakes—this expansive estate on prestigious Lake Butler Boulevard is more than just a home: it’s a lifestyle destination, purposefully designed to inspire connection, relaxation, and recreation. With its flexible layout, multiple living spaces, and resort-style amenities, it offers the perfect setup for multigenerational living without compromise. From the moment you arrive, you’ll sense the pride and care that has gone into crafting this one-of-a-kind residence. Meticulously expanded and improved over decades, the home features five generously sized bedroom suites, including a luxurious owner’s retreat with fine finishes and boutique-style custom closets. Whether accommodating extended family, live-in help, or guests, everyone enjoys their own private space. For culinary enthusiasts and entertainers alike, two full gourmet kitchens—one upstairs and one downstairs—provide unmatched convenience and versatility. Host formal holiday gatherings, casual poolside brunches, or multiple family dinners with ease. Both kitchens are thoughtfully appointed with high-end appliances and stylish finishes that reflect the home’s refined character. The garage is a masterpiece in itself, built to accommodate your most ambitious lifestyle. Store your 45-foot Prevost RV with full hookups—sewer, water, cable, and power—or tuck away your 50-foot center console, classic cars, or workshop equipment in the four additional bays. Whether you’re an adventurer, collector, or weekend explorer, this space is a rare find in residential real estate. Outdoor living takes center stage. A private beach invites sunbathing and quiet reflection by day, while the oversized gas fire pit becomes a natural gathering point at night for family, friends, and unforgettable moments. The resort-style pool area includes a gas fireplace and summer kitchen, perfect for year-round entertaining. Speakers are integrated throughout both indoor and outdoor spaces, creating a seamless atmosphere of leisure and luxury. Inside, modern comforts abound: three zoned A/C units with Nest thermostats, two tankless gas water heaters, and a finished storage area above the garage offer functionality and peace of mind. Located in the highly coveted Town of Windermere, residents here enjoy more than just natural beauty—they cherish a community rooted in tradition, charm, and quality of life. Walk to the Farmer’s Market, explore local parks, or attend beloved events like food truck nights, craft festivals, and holiday parades. The town library, family-owned shops, and quaint cafes further enhance the walkable lifestyle. Minutes away, you’ll find world-class golf, upscale shopping, fine dining, and easy access to highways leading to Orlando’s top attractions, excellent schools, and international airport. As an added value, completed architectural plans by Dirk Arace of Arace Designs are available, offering an exciting opportunity to customize or expand the estate with one of Central Florida’s most respected designers. Whether you’re seeking a private lakeside sanctuary, a home for generations, or a place to live your dream by the water, this Windermere gem is truly extraordinary. Listing agent is owner of the property.

11002 Lake Butler Boulevard, Windermere

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