Explore Keenes Pointe, Windermere, FL Homes for Sale

5 Bedroom Homes for Sale in Keenes Pointe, Windermere, FL

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Welcome to your dedicated resource for 5 bedroom homes for sale in Keenes Pointe, Windermere, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Keenes Pointe, Windermere, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the 5 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 5 Bedroom Homes for Sale in Keenes Pointe, Windermere, FL

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

Exceptional Keene's Pointe Pool Home with Rare Multi-Generational Layout with a Pond View! Welcome to this exceptional 5-bedroom, 4.5-bath residence nestled on one of the most peaceful cul-de-sacs in the Keene's Pointe community. Perfectly positioned on a stunning water-view homesite with an expansive backyard and exceptional privacy, this home offers an incredibly flexible floor plan rarely found in today's market. The thoughtfully designed layout places the main living areas, private office, and spacious primary suite all on the first floor, creating the perfect setup for everyday living. Upstairs, three generously sized bedrooms and a large bonus room are tucked away, providing an ideal retreat for family or guests. Adding even more versatility, a completely separate detached in-law suite features a spacious bedroom and full bath, making it perfect for extended family, guests, a private home office, or live-in accommodations. Major updates provide peace of mind for years to come, including a brand-new roof, new glass sliders and windows, new septic system and drain field, A/C in 2024, and 2021 water heater. Keene's Pointe is one of Central Florida's premier 24-hour guard-gated communities, set along the pristine Butler Chain of Lakes. Residents enjoy beautifully maintained parks, playgrounds, walking trails, private boat launch access to Lake Burden, fishing piers, and a vibrant community atmosphere. Optional membership to the renowned Golden Bear Club provides access to a Jack Nicklaus Signature golf course, tennis and pickleball courts, a resort-style swimming pool, fitness center, and more. Families will also appreciate the community's proximity to top-rated schools, upscale shopping, fine dining, world-famous attractions, and Orlando International Airport.

9904 Brentford Court, Windermere

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

5 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

*** One of the lowest $/SF in Keene's Pointe *** Welcome to this updated, move-in ready luxury home in Keene’s Pointe, one of Windermere’s premier 24-hour guard-gated golf communities and home to the Golden Bear Club. Offering 5 bedrooms, 4 bathrooms, and 3,358 square feet of living space, this beautifully upgraded residence combines luxury finishes, functional design, and an exceptional Central Florida lifestyle just minutes from Disney, top-rated Windermere schools, shopping, dining, and major highways. Situated on an oversized homesite with a large driveway accommodating up to nine vehicles and a three-car garage, this home makes an immediate impression. Inside, the open-concept floor plan features commercial-grade porcelain tile flooring, crown molding, updated lighting, designer finishes, and spacious living areas designed for both everyday living and entertaining. Just off the entry, a custom wet bar with wine refrigerator and beverage fridge flows seamlessly into the dining area and main living space. The updated chef’s kitchen overlooks the family room and showcases quartz countertops, a large center island with additional 36-inch cabinetry storage, a farmhouse sink, soft-close dovetail cabinetry, stainless steel appliances, a natural gas range with vent hood, and an ideal layout for entertaining guests or hosting family gatherings. The spacious first-floor primary suite serves as a private retreat and features a large custom walk-in closet along with a beautifully updated spa-style bathroom complete with dual vanities, soaking tub, oversized walk-in shower with multiple spray features, and custom tile details. Three additional bedrooms and two updated bathrooms are located on the main level, while all bedrooms include custom closet systems and updated ceiling fans. Upstairs, newly finished stairs lead to a versatile loft with luxury vinyl plank flooring, an additional bedroom, and a full bathroom, creating flexible space ideal for a media room, home office, guest suite, or multigenerational living setup. The outdoor living space is designed for Florida entertaining with an approximately 900-square-foot paver patio, natural gas firepit, spacious backyard, and nightly Disney fireworks views. The rear yard is also prewired with 50-amp power for a future pool installation if desired by the next owner. Additional improvements include a 2021 roof replacement, extensive updates throughout the home, a new natural gas meter installed in 2025, and a meticulously maintained septic system with annual servicing over the past 10 years, a new septic alarm box and meter installed in 2021, and a new septic float installed in early 2025. The property also offers exceptional storage with three overhead garage storage racks rated for 600 pounds each, along with a fully planked, lighted, and walkable attic space above the entire three-car garage. Residents of Keene’s Pointe enjoy access to private boardwalks to Lake Tibet and the Butler Chain of Lakes, two community boat ramps, four playgrounds, and year-round neighborhood events. Optional Golden Bear Club membership offers access to championship Jack Nicklaus-designed golf, tennis courts, resort-style pool, fitness center, dining, and social activities. This updated Windermere luxury home offers a rare opportunity to own in one of Central Florida’s most desirable gated golf communities. Schedule your private showing today.

11524 Claymont Circle, Windermere

5 Beds ⋅ 8 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Set along the pristine shores of Lake Tibet Butler, this exceptional estate within Keene's Pointe is a masterclass in timeless design, refined craftsmanship, and elevated lakefront living. Spanning over 7,500 square feet, every detail has been thoughtfully curated to balance grandeur with comfort. This home is meticulously cared for with improvements which recent improvements such as a new tile 250k roof (August 2024) and upgraded dock system, ensuring both beauty and peace of mind for years to come. A dramatic foyer makes a lasting first impression, overlooking formal living and dining spaces defined by architectural ceilings, designer lighting, and rich travertine flooring. At the heart of the home, the gourmet kitchen is both stunning and functional—featuring professional-grade appliances, custom cabinetry, stone countertops, and an expansive island that seamlessly connects to the dining area and inviting family room. Designed for entertaining, a showstopping game room features a 2,000-gallon saltwater aquarium—famously showcased in The Wall Street Journal—while French doors throughout the main living areas open to a fully screened resort-style patio. Here, a spa, fireplace, and summer kitchen create the ultimate indoor-outdoor living experience. The owner’s suite offers a true private retreat, complete with a fireplace, sitting area, wet bar, and dual dressing rooms—including a two-story boutique-style closet with an adjoining massage room. The spa-inspired bath features a soaking tub and steam shower, delivering a serene, resort-like escape. The main level also includes a private guest suite, a dedicated office with built-in safe, and an oversized laundry and utility space designed for both efficiency and versatility. Upstairs, a fully equipped fitness room and three additional en-suite bedrooms with sleek, modern finishes provide comfort and privacy for family and guests. Outdoors, lush landscaping and mature trees frame a tranquil setting designed for both relaxation and connection to nature. Meandering pathways lead past fountains and gardens to a secluded fire pit beside a gentle stream, while a charming bridge guides you to a private dock on the lake—enhanced with a Trex system for lasting durability. Located within the guard-gated community of Keene’s Pointe—home to the Jack Nicklaus Signature Golf Course at Golden Bear Club and offering direct access to the Butler Chain of Lakes—this residence represents a rare opportunity to own a true legacy property.

9349 Tibet Pointe Circle, Windermere

5 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Luxury Pond-View Home in Keene’s Pointe – Windermere Located in the highly sought-after gated golf community of Keenes Pointe, this beautiful 5-bedroom, 4-bathroom residence offers an exceptional combination of space, comfort, and scenic surroundings. The home features a thoughtfully designed floor plan with a private den/office, formal living and dining rooms, and expansive living areas perfect for both everyday living and entertaining. Large windows and sliding doors allow natural light to flow throughout the home while showcasing the peaceful pond views. The spacious kitchen opens to the family room and overlooks the outdoor living area, creating the perfect setting for gatherings and family time. Step outside to enjoy your private screened pool and spa, ideal for relaxing while enjoying the tranquil waterfront setting. Additional highlights include: 5 spacious bedrooms 4 full bathrooms Private den / home office Formal living and dining rooms 3-car garage Beautiful pond views Private pool and spa Brand new roof (2024) Situated in the prestigious Keenes Pointe community, residents enjoy 24-hour guard-gated security, tree-lined streets, and proximity to world-class golf, shopping, dining, and top-rated schools. This is a rare opportunity to own a spacious home with water views in one of Windermere’s most desirable communities.

11339 Camden Park Drive, Windermere

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