5 Beds ⋅ 4 Baths ⋅ Lakes/Windermere Ph 02a SubDv. ⋅ 34786 Zip Code

Welcome to this beautifully maintained two-story home in the highly sought-after Lakes of Windermere, offering 5 bedrooms, 3.5 bathrooms, a private screened pool, and a brand-NEW ROOF currently being installed for added value and peace of mind. Designed with both comfort and functionality in mind, the home features a bright, open floor plan with spacious living and dining areas, tile flooring throughout the main living spaces, and flexible room to accommodate everyday living, entertaining, working from home, or hosting guests. The well-appointed kitchen showcases wood cabinetry, granite countertops, stainless steel appliances, a center island, and seamless flow into the main living areas, making it the heart of the home. The spacious primary suite serves as a relaxing retreat with a large walk-in closet, dual vanities, a soaking tub, and a separate walk-in shower. Step outside to enjoy Florida living year-round in the screened lanai overlooking the private pool, brick paver deck, and fully fenced backyard—perfect for entertaining, family gatherings, or simply unwinding in your own backyard oasis. Located in the desirable Lakes of Windermere community, residents enjoy access to a playground, covered picnic area, and convenient proximity to top-rated schools, shopping, dining, Disney, major highways, and everything Southwest Orlando has to offer.

12912 Droxford Road, Windermere

$2,960,000

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

Located within the prestigious guard gated community of Keene’s Pointe, this extraordinary estate offers a rare combination of luxury, privacy, and breathtaking views. Positioned on a premier lot with combined water and golf course frontage, this one-of-a-kind residence captures stunning vistas from every angle. On arrival, the expansive, multi-car, circular driveway provides ample parking for all, blending grand scale with ultimate convenience and estate-style privacy. Enter through custom wrought-iron gates into a private courtyard oasis, which makes for an unforgettable first impression. Boasting nearly 6,000 square feet of thoughtfully designed living space, the home features 5 bedrooms, including a detached casita/in-law suite with separate entrance, full bathroom, fridge and microwave. In addition, there is an equipped media room with half bathroom, also with microwave and fridge. A bonus room that can be used as a home office or gym is located off the downstairs primary suite. The gourmet kitchen is the heart of the home, showcasing custom cabinetry, granite countertops, premium appliances including a built-in Miele coffee machine, Wolf range, double oven, an incredible center island, wine cellar and generous gathering spaces. Expansive living and dining areas, with soaring ceilings, exquisite features such as, Venetian plaster, travertine floors, wood beams and custom built ins. The luxurious primary suite offers a private sanctuary with elegant finishes, dual custom closets, one with an additional washer and dryer set, a beautifully designed bathroom and private access to the office/gym/bonus rm. Three 2nd floor guest rooms include a potential second primary suite which provides exceptional accommodations for multigenerational living or visiting guests. Recently remodeled, this spacious suite has a full bathroom, walk-in closet and double door access to the balcony with its glorious golf course and water views. Outside, an oasis awaits. Floor to ceiling glass sliders in the living room offer uninterrupted views and provide access to the resort-style screened lanai featuring an expansive pool, sauna and outdoor fireplace. Indoor/outdoor speakers, security cameras, app controlled pool system with multi light show. A private sports court further enhances the lifestyle offered by this exceptional property. Keene’s Pointe is in the heart of Windermere and offers 24-hour manned security, access to the community boat ramp and optional membership to the Golden Bear Golf & Country Club, where golf, tennis, pickleball, gym, restaurant and events are included in the membership fee. Close to state-of-the-art medical facilities, theme parks, shopping, restaurants and high achieving schools, this exceptional estate represents a rare opportunity to own one of Windermere's most distinctive luxury residences.

6417 Lake Burden View Drive, Windermere

$6,500,000

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

Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan presents a rare opportunity to enjoy the ease of modern luxury within one of the world's most distinguished golf club communities. Thoughtfully designed and never lived in, the home combines timeless architecture with professionally curated interiors by Design Specifications, creating a refined retreat where every detail has been carefully considered. Spanning more than 5,400 square feet, the five-bedroom residence unfolds through a series of light-filled living spaces distinguished by bespoke millwork, tailored cabinetry, and a sophisticated palette of designer-selected finishes. Clean architectural lines and expansive gathering areas create an atmosphere that feels both grand and inviting, while thoughtfully integrated design elements elevate everyday living. Throughout the home, custom cabinetry conceals a fully integrated Sub-Zero, Wolf, and Cove appliance suite, allowing the chef's kitchen to maintain its beautiful aesthetic while delivering professional-grade performance. Well-appointed entertaining spaces nearby transition effortlessly from intimate family gatherings to larger celebrations.Private bedroom retreats offer comfort and tranquility, while spa-inspired baths showcase carefully selected finishes, fixtures and materials that evoke exceptional craftsmanship. The primary suite serves as a sanctuary unto itself, complete with a private beverage bar and thoughtfully designed spaces that encourage both relaxation and retreat.Beyond the interiors, walls of glass open to an inviting outdoor environment designed for year-round enjoyment. A fully equipped summer kitchen anchors the outdoor living experience, creating a natural extension of the home's entertaining spaces and providing the perfect backdrop for gatherings beneath Florida's sunshine and tropical climate.Surrounded by lush landscaping, sparkling water features, and the natural beauty that defines The Gardens of Isleworth, the residence enjoys a setting that feels both private and refined. Residents of Isleworth enjoy access to a lifestyle renowned for championship golf, world-class amenities, exceptional service, and a level of privacy rarely found. Combining the freshness of brand-new construction with the prestige of an established luxury community, this is more than a home, it is an opportunity to experience Isleworth at its finest.

9316 Gladys Garden Ct, Windermere

$765,990

5 Beds ⋅ 3 Baths ⋅ Windermere Sound SubDv. ⋅ 34786 Zip Code

Welcome to one of the most desirable communities in Windermere! This beautifully designed home offers 5 spacious bedrooms, 3 full bathrooms, and an exceptional floor plan featuring a large family room on the main level and an additional loft upstairs, providing the perfect balance of comfort, functionality, and flexible living space. Boasting approximately 3,285 square feet of living area, this is one of the builder’s most popular and highly sought-after floor plans. Every room has been thoughtfully designed to maximize space, natural light, and everyday convenience, making it ideal for growing families, entertaining guests, or working from home. The community offers outstanding amenities and a welcoming neighborhood atmosphere. Residents enjoy convenient access to major highways, shopping centers, supermarkets, restaurants, and everyday essentials. Located in the heart of Central Florida, this home is just a short drive from Disney World, Universal Orlando Resort, SeaWorld Orlando, and many of the area’s world-famous attractions, while also providing easy access to Orlando International Airport and Downtown Orlando. If you’re looking for a spacious, move-in-ready home in one of Windermere’s most sought-after communities, this is an exceptional opportunity you won’t want to miss.

7409 Fairgrove Avenue, Windermere

$1,075,000

5 Beds ⋅ 4 Baths ⋅ Windermere Trls Ph 3b SubDv. ⋅ 34786 Zip Code

Fully Furnished- Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathrooms, a media room, loft, gym, and game room, providing plenty of space for both everyday living and entertaining. The home features elegant iron stair railings, formal living and dining areas, and an open-concept layout designed for comfort and functionality. The gourmet kitchen showcases stainless steel appliances, a 36-inch cooktop, 42-inch cabinetry with crown molding, quartz countertops, upgraded backsplash, and a spacious walk-in pantry. The primary suite includes a large walk-in closet and a luxurious bathroom with dual vanities and a private water closet. An upgraded home theater with fiber-optic illuminated ceiling and wall panels creates a unique entertainment experience. Step outside to enjoy a beautifully landscaped, fully fenced backyard with dual gate access, a tranquil water feature, and an extended covered lanai perfect for relaxing or entertaining. Residents enjoy access to community amenities including walking trails, a resort-style pool, playground, dog park, pavilions, and fitness areas. The property is being offered partially furnished, with many of the furnishings and features shown in the photos included in the sale.

8316 Lookout Pointe Drive, Windermere

$1,569,000

5 Beds ⋅ 4 Baths ⋅ Reserve At Lake Butler Sound SubDv. ⋅ 34786 Zip Code

Exceptional value in Lake Butler Sound! Welcome to 11027 Hawkshead Court, a beautifully updated luxury home in Windermere, FL offering 4 bedrooms, a dedicated office, 4 bathrooms, approximately 3,500 square feet, and a private 0.4-acre corner lot within one of Central Florida's premier guard-gated communities with 24-hour roving security. Extensively renovated between 2022 and 2026, this move-in-ready pool home blends timeless design, quality craftsmanship, and high-end finishes throughout. The open-concept floor plan is anchored by a chef's kitchen featuring upgraded countertops, a 7-foot built-in Dacor refrigerator with dual ice makers, 5-burner Dacor gas cooktop, double wall ovens with steam cooking, and abundant prep and storage space. New flooring throughout creates a seamless flow, while 12-foot ceilings in the main living areas and primary suite enhance the home's spacious feel. Designed for both everyday living and entertaining, the home showcases custom built-ins with a rolling library ladder, a striking entertainment wall with fireplace and built-in lighting, and a thoughtfully designed split floor plan. A private office with custom built-in shelving offers the perfect work-from-home space. The spacious primary suite is privately positioned away from the secondary bedrooms and features dual California Closets and a spa-inspired bath with marble tile, a custom vanity, and a freestanding soaking tub. Two secondary bedrooms share a Jack-and-Jill bathroom, while the fourth bedroom has its own full bath, making it ideal for guests, teens, or multigenerational living. Step outside to your own private backyard retreat featuring a gas-heated pool and raised spa, multiple covered and open-air entertaining areas, a turfed putting green, and an additional fenced grassy side yard. Situated on a premium corner lot bordered by two quiet cul-de-sacs, the outdoor living spaces provide exceptional privacy and tranquility. Additional upgrades include premium Pella doors, interior and exterior paint, a whole-home owned water softener system, new flooring throughout, a new septic drain field, custom California Closet systems, and numerous additional improvements that make this home truly move-in ready. Located in the Reserve at Lake Butler Sound, this exceptional property offers luxury, privacy, and convenience just minutes from downtown Windermere, top-rated schools, world-class golf, fine dining, shopping, and Orlando's premier attractions. A rare opportunity to own a meticulously updated luxury home in one of Windermere's most sought-after communities.

11027 Hawkshead Court, Windermere

$6,900,000

5 Beds ⋅ 7 Baths ⋅ Down Acres Estates SubDv. ⋅ 34786 Zip Code

A rare architectural statement on Lake Down, this extraordinary contemporary waterfront estate redefines luxury living in the heart of Windermere. Positioned on the prestigious Butler Chain of Lakes, this stunning residence offers 5 bedrooms, 5 full baths, 2 half baths, and a private elevator, seamlessly blending sophisticated design with effortless lakefront living. Constructed to Miami coastal specifications, the home was engineered with exceptional attention to quality, durability, and structural integrity while maintaining its striking modern aesthetic. Floor-to-ceiling glass walls frame breathtaking water views and flood the home with natural light, while soaring ceilings and open-concept living spaces create a dramatic yet inviting atmosphere. Every detail has been thoughtfully curated, from the designer finishes and statement lighting to the seamless integration of indoor and outdoor spaces. Luxury wellness amenities, including a steam shower, further enhance the home's resort-inspired appeal. The outdoor living experience is equally impressive, featuring a spectacular pool, expansive covered entertaining areas, and a fully equipped outdoor kitchen designed for gatherings both intimate and grand. Above it all, the rooftop terrace offers panoramic views of Lake Down and the surrounding landscape, creating the perfect setting for morning coffee, sunset cocktails, or evenings under the stars. As night falls, enjoy a truly magical experience as Disney fireworks illuminate the horizon from the comfort of your private rooftop retreat. Whether spending the day on the Butler Chain, entertaining guests poolside, or relaxing while taking in the waterfront views, this residence delivers an unparalleled lifestyle defined by elegance, comfort, and connection to the water. Ideally located just minutes from Restaurant Row, Downtown Orlando, the Mall at Millenia, Disney, Universal Studios, Orlando International Airport, and major thoroughfares including SR-408, this exceptional property combines the serenity of premier lakefront living with unmatched convenience. From sunrise over Lake Down to Disney fireworks dancing across the night sky, this is a home designed to inspire, impress, and elevate everyday living.

9061 Ron Den Lane, Windermere

$930,000

5 Beds ⋅ 5 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code

Virtually Staged. Enjoy the best of Central Florida living in a highly sought-after neighborhood, just minutes from local schools, shopping, great restaurants, and magic of Disney. This 5-bedroom, 4.5-bathroom pool home is clean, well-maintained, and ready for move-in, featuring a freshly painted interior along with a newly painted exterior stucco, patio, and doors. THE FIRST FLOOR Walking in from the two-car garage and paver driveway, the covered front porch opens into a bright floorplan with high ceilings and tile floors. Right off the entrance is a formal sitting room that works perfectly as a quiet reading nook or music space. Down the hall, there's a convenient half-bath and a coat closet, leading into a large formal dining room made for family dinners. The kitchen connects right to the family room and comes with a large island and breakfast bar, plenty of counter and cabinet space, a big pantry, stainless steel appliances, recessed lighting, and a hidden back scullery. Tucked away at the back of the main floor is a guest bedroom and full bath, which is great for a mother-in-law suite or a playroom. THE SECOND FLOOR Upstairs, a large loft gives you a flexible second living area or media space. The laundry room is also on this level, making laundry a lot easier. The primary suite is set apart for privacy and includes separate individual vanities, a soaking tub, a glass shower, and a walk-in closet big enough to be a small room on its own. On the left side of the house, bedrooms 3 and 4 share a Jack-and-Jill bathroom. Across the way, bedroom 5 sits directly next to the home's fourth full bath. OUTDOOR LIVING Out back, the home looks out over a quiet pond. The covered, screened patio leads to a heated pool, giving you a great spot to hang out during the day and watch the nightly Disney fireworks from your own backyard

12929 Westside Village Loop, Windermere

$699,000

5 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 05 SubDv. ⋅ 34786 Zip Code

Virtually Staged. Enjoy exceptional privacy with beautiful conservation views behind & expansive green space beside the home, creating a peaceful setting rarely found in the community. Tucked away on a desirable homesite, 7906 Jailene Drive offers 2,618 SF, 5 bedrooms, 3 full bathrooms, 2-car garage, all filled with thoughtfully designed living spaces & ample dedicated guest parking conveniently located nearby. A welcoming front porch sets the tone as you enter the home, where a custom wood accent wall in the foyer creates a warm and inviting first impression. The open-concept layout offers spacious living & dining areas that flow seamlessly into the kitchen & family room. A dramatic two-story ceiling in the family room fills the space with natural light creating an impressive sense of openness, making it the perfect place to gather & entertain. The kitchen features granite stone countertops, abundant solid wood cabinetry, ample prep space, a kitchenette area & a functional layout overlooking the main living areas. Fresh interior paint, luxury vinyl flooring throughout & charming designer light fixtures add style and warmth throughout the home. The versatile floor plan includes a first-floor study/den which can also be used as a 5th bedroom with full bathroom. This space is ideal for a home office, family, guests, or multi-generational living. Upstairs, you’ll find four additional bedrooms, including the spacious primary suite, along with two full bathrooms & a conveniently located laundry room. Step outside to the screened lanai with tranquil conservation views, embracing nature at its best with exceptional privacy. Enhanced by a hand-painted decorative concrete finish, this outdoor retreat provides the perfect space for morning coffee, outdoor dining, or relaxing evenings, especially with a fully-fenced backyard. Located in the highly desirable Lake Sawyer community, residents enjoy access to a community pool, playground, park, and scenic sidewalks throughout the neighborhood. The home is zoned for sought-after schools, including Sunset Park Elementary, Horizon West Middle School, and Windermere High School. Just minutes from Horizon West and Hamlin Town Center, you’ll enjoy convenient access to shopping, dining, entertainment, and everyday conveniences. Major roadways are nearby, providing easy access to Walt Disney World, Disney Springs, downtown Orlando, Orlando International Airport, and all that Central Florida has to give. Combining privacy, functionality, thoughtful updates, and an exceptional location, this move-in-ready home presents a rare opportunity in one of Windermere’s most sought-after communities. Additional highlights include a brand-new roof (June 2026), HVAC 2024, abundant storage & a desirable location close to shopping, dining, schools, & major roadways. Combining privacy, functionality, & modern updates, this move-in-ready home is ready to welcome its next owners!

7906 Jailene Drive, Windermere

$3,800,000

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

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. Guests will enjoy complete privacy in the generously sized 1st floor guest suite. 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

$1,400,000

5 Beds ⋅ 4 Baths ⋅ Butler Bay,Windermere Club SubDv. ⋅ 34786 Zip Code

Welcome to this exceptional luxury residence offering 5 spacious bedrooms, 4 beautifully appointed bathrooms, and 3,929 square feet of refined living space on an expansive homesite of over half an acre. Perfectly positioned in a highly sought-after location, this stunning property combines elegance, comfort, and privacy with resort-style outdoor living. Surrounded by lush, mature landscaping, the home makes a striking first impression and provides a serene setting for everyday living. Inside, thoughtfully designed interiors feature generous living and entertaining spaces, abundant natural light, and sophisticated finishes throughout. The spacious layout seamlessly accommodates both intimate family gatherings and large-scale entertaining. The outdoor retreat is equally impressive, highlighted by a sparkling pool and expansive patio areas ideal for relaxation and year-round enjoyment. The oversized lot offers exceptional privacy while providing ample space for outdoor activities and future enhancements. Residents enjoy access to outstanding community amenities and the convenience of a prime location close to premier shopping, dining, entertainment, top-rated schools, and major transportation routes. Offering an unparalleled blend of luxury, space, and lifestyle, this remarkable property presents a rare opportunity to own a distinguished home in one of the area’s most desirable communities. You're also nestled within a well-established community, this property enjoys an enviable location close to major highways, ensuring convenient access to all amenities. Just minutes away, residents can indulge in excellent shopping opportunities, dine at a variety of luxury and casual eateries, and explore nearby theme parks for entertainment. The neighborhood benefits from proximity to brand-new, state-of-the-art hospitals and a top notch school system, providing peace of mind for residents seeking quality healthcare services and high end education for their family. This vibrant community offers an abundance of options to suit every lifestyle need and preference. Call today to schedule a private tour.

1700 Lake Roberts Court, Windermere

$2,474,000

5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Positioned on a corner homesite along the 18th hole of the Golden Bear Club within the guard-gated community of Keene's Pointe, this thoughtfully updated custom home offers five bedrooms, four full bathrooms, and three half bathrooms, combining exceptional golf-front living with breathtaking views of the golf course, pool, and surrounding landscape. A grand foyer welcomes guests with a soaring 22-foot ceiling, while oversized tile flooring extends throughout the first floor. Expansive windows fill the home with natural light while creating a seamless connection to the outdoor living spaces. The well-designed floor plan features a dedicated office with a coffered ceiling, spacious living and dining areas, and a beautifully appointed kitchen with beautiful cabinetry, granite countertops, a professional-grade gas range, center island, and abundant storage. Just off the kitchen and family room is a spectacular custom entertainment bar featuring extensive cabinetry, generous serving space, and four under-counter refrigerators, creating the ultimate setting for entertaining. The first-floor primary suite serves as a private retreat with direct access to the lanai and pool area. The updated spa-inspired bath features designer cabinetry, quartz countertops, a freestanding soaking tub, oversized walk-in shower, premium fixtures, and elegant floor-to-ceiling tilework. Completing the owner's retreat are two spacious walk-in closets, including a large walk-in closet directly off the bedroom and an additional oversized walk-in closet conveniently located off the bathroom, providing exceptional storage and organization. The secondary bedroom layout offers both comfort and privacy for family and guests. Two bedrooms feature en-suite bathrooms, while two additional bedrooms are connected by a Jack-and-Jill bathroom. The expansive second-floor bonus room serves as a versatile gathering space, ideal as a media room, game room, lounge, or secondary family room. A dramatic vaulted tongue-and-groove wood ceiling creates architectural interest and warmth, while large windows and French doors fill the space with natural light and provide direct access to the covered second-floor terrace overlooking the pool and golf course. A conveniently located half bath serves the bonus room and outdoor terrace, making the space perfectly suited for entertaining family and guests. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers an abundance of covered outdoor living space. The resort-style outdoor area features a covered lanai, summer kitchen, pool, spa, dedicated pool bath, and multiple gathering spaces thoughtfully positioned to capture views of the Golden Bear Club's signature finishing hole. An expansive covered second-floor terrace with a tongue-and-groove wood ceiling is accessible from multiple bedrooms as well as the bonus room, providing stunning views of the pool and golf course. A spiral staircase leads to a private third-story observation deck featuring a wet bar and panoramic views across the fairways and surrounding treetops, creating the perfect setting for entertaining, enjoying evening sunsets, or watching play unfold along the Golden Bear Club's signature finishing hole.

6288 Blakeford Drive, Windermere

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