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Homes for Sale with a Pool in Windermere, FL

Welcome to your dedicated resource for homes for sale with a pool in 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 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 with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Windermere, FL

$1,775,000
4 Beds 4 Baths Keenes Pointe SubDv. 34786 Zip Code
SIGNIFICANT PRICE IMPROVEMENT! MOTIVATED SELLER! Welcome to a truly exceptional custom home in Keene's Pointe, one of Windermere’s most sought-after guard-gated communities. Built by W. J. Sauerwine and set on a beautifully landscaped .43-acre homesite with mature oak trees, this residence offers a rare combination of privacy, thoughtful design, and extensive modern upgrades. This 4-bedroom plus office, 4-bath home features a highly functional, split floorplan layout with nearly all living space on the main floor, including the primary suite and main living areas, with one bedroom and full bath upstairs. The home has been extensively updated throughout, beginning with all new interior paint and continuing into a fully renovated kitchen with updated finishes and appliances. All four bathrooms have been completely reimagined from floor to ceiling with today’s luxury buyer in mind, creating a cohesive and elevated feel throughout the home. Attention to detail is evident in every space, from the custom built-ins in the office and family room to the all-new lighting and chandeliers installed throughout both the interior and exterior, all integrated with a Lutron system for seamless control. Sonos in-ceiling speakers have been installed throughout the home, creating a whole-home audio experience. What truly sets this home apart is its advanced energy efficiency and independence. Equipped with a Tesla solar system, multiple Powerwalls and electricity backup, the home is designed to operate seamlessly even during outages while significantly reducing long-term energy costs. With the ability to sell excess power back to the grid and the convenience of EV charging at the ready, this is a rare blend of luxury and forward-thinking functionality. The primary suite offers a private retreat with French doors leading to the lanai, ample space for a sitting area, and a spa-inspired bath with dual vanities, soaking tub, walk-in shower, and generous closet space. Secondary bedrooms are well-positioned with direct bath access, providing both comfort and functionality. Outdoor living is equally impressive, featuring a screened pool and an expansive covered lanai designed for both relaxation and entertaining. The rear patio is equipped with an outdoor refrigerator, sink, and TV, creating the perfect setting for year-round enjoyment. The home is also equipped with a Ring security camera system covering the exterior. Ideally located directly across from The Golden Bear Club members' driving range from the front, with golf course views to the rear, this home also provides access to Keene’s Pointe amenities, such as parks and playgrounds, including community boat ramp to Lake Burden, and access to the Butler Chain of Lakes for recreation. Membership at The Golden Bear Club further allows for access to the Jack Nicklaus-designed golf course, tennis courts, fitness center, and restaurant. Residents of Keene's Pointe enjoy a lifestyle that blends privacy, recreation, and convenience, all just minutes from the world's best theme parks and entertainment, Winter Garden Village, Restaurant Row, and top-rated schools. This is a rare opportunity to own a fully updated, energy-efficient custom home in Keene’s Pointe that truly stands apart from the rest. Furniture custom-designed specifically for the home is negotiable, offering a potential turnkey opportunity for the next owner.

6110 Keenes Pointe Drive, Windermere

$1,099,000
4 Beds 3 Baths Keenes Pointe SubDv. 34786 Zip Code
Reduced 50k! Seller motivated! Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartzite countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026), Driveway replaced 06/2026. This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!

8351 Bowden Way, Windermere

$724,900
4 Beds 3 Baths Summerport SubDv. 34786 Zip Code
Short Sale. Super Rare Opportunity! Tucked away in one of Windermere’s most desirable areas is the beautiful home on over 1 half acre homesite on a corner lot with no rear neighbors and a gorgeous lake view. Don't sleep 'on' this home if you want to sleep 'in' this home! New roof 2023. Interior features include a fully remodeled kitchen with white 42" cabinets with crown moulding and gold hardware, custom vent hood with a tile backsplash. In addition a huge quartz centerpiece island with upgraded stainless steel appliances including a gas range plus a farmhouse sink. All overlooking the huge family room, 3 gold pendant lights and gold chandelier. New vinyl plank flooring throughout the entire first floor plus the stairs and loft on the 2nd floor. Spacious master suite with double sink vanity with garden tub and separate shower. 2 walk in closets as well. Formal living room, independent den/office with storage closet, half bath with custom vessel sink and indoor laundry room round out the first floor. Upstairs you will find the aforementioned loft along with 3 additional bedrooms and full bath with updated floor to ceiling tile and glass door shower. As you walk out onto the covered patio, along with the tremendous screen enclosed pool and spa you will find plenty of green grass to run and play in the fully fenced yard and if you need even more, utilize the greenspace to the side of the home as well. Enjoy the tranquil views of the serene lake from the back or relax on the extended covered front porch on a rocker from Cracker Barrel and if your in the mood for some ice cream or coffee, just a 5 minute walk from the front door is Kelly's Ice Cream and Foxtail coffee and even a pizza shop, and on your way you will pace by the "A" rated Keene Crossing Elementary school. .Additional community amenities include clubhouse with pool, tennis and basketball courts, sand volleyball and a private pier. Location benefits include easy access to Horizon West Town Center and all the monthly activities, Windermere Prep, Foundation Academy private schools, numerous restaurants and shopping, SR 429, Florida Turnpike and so much more!

14255 Sonco Avenue, Windermere

$3,900,000
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

$1,854,000
6 Beds 6 Baths Balmoral SubDv. 34786 Zip Code
Located within the prestigious gated community of Balmoral Estates, this spectacular 6-bedroom, 5.5-bath 4 car garage luxury estate sits on an expansive ¾-acre homesite and has been completely renovated with exceptional custom upgrades throughout. From the moment you arrive, the property makes a striking impression with a brand-new circular paver driveway centered around a dramatic custom water fountain, creating a grand sense of arrival. The residence also features a spacious four-car garage equipped with two EV charging stations, offering modern convenience for today’s lifestyle. Custom front entry doors open to an impressive grand foyer with elegant marble tile flooring, introducing the refined finishes that define the home. Inside, the residence has been beautifully transformed with brand-new flooring throughout, custom recessed lighting, upgraded designer fixtures, and crown molding across the main level. At the heart of the home is a stunning designer gourmet kitchen featuring custom white cabinetry, granite countertops, a striking tile mosaic accent wall, and premium KitchenAid stainless steel appliances, including a built-in oven, microwave, and cooktop. Perfect for entertaining or multi-generational living, the home also features a fully rebuilt second kitchen with granite countertops, custom cabinetry, and stainless steel appliances with direct access to the outdoor entertaining area. The home offers two luxurious primary suites, each thoughtfully designed as a private retreat. The upstairs primary suite features a spa-inspired bathroom with dual vanities, custom cabinetry, a dedicated makeup vanity, an oversized jacuzzi soaking tub, and a beautifully tiled walk-in shower. Outdoor living is equally impressive with a custom outdoor kitchen complete with built-in grill, professional venting, and built-in speakers, creating the perfect setting for entertaining and relaxation. Three brand-new sliding glass doors upstairs open to a private balcony, enhancing the home’s seamless indoor-outdoor lifestyle. Recent upgrades provide comfort and peace of mind, including a new Carrier 5-ton air conditioning system, new 50-gallon water heater, whole-home water purification system, and a new pool pump installed within the last six months. With extensive renovations, luxurious finishes, and exceptional indoor-outdoor living, this remarkable residence offers the sophistication, comfort, and lifestyle expected of a premier luxury estate.

9057 Balmoral Mews Square, Windermere

$879,000
4 Beds 3 Baths Windermere Isle SubDv. 34786 Zip Code
Virtually Staged. Lake View Home with Private Pool & Fireworks Views – Minutes from Walt Disney World Imagine living in a home that perfectly combines comfort, elegance, and practicality in one of the most desirable areas of Windermere. This beautiful residence offers stunning lake views and magical nightly fireworks views from Walt Disney World, creating a truly unique living experience. From the moment you arrive, the well-maintained landscaping and inviting front porch set a warm and welcoming tone. The home features 4 bedrooms and 3 full bathrooms, with a thoughtfully designed open-concept layout that seamlessly connects the living room, kitchen, and dining area. The gourmet kitchen is a true highlight, equipped with stainless steel appliances, custom cabinetry, quartz countertops, a double oven, and a spacious pantry—perfect for those who love cooking and entertaining. Sliding glass doors open to the outdoor space, where a private pool and summer kitchen are currently being completed and will be ready within one month, creating the perfect setting for relaxing or entertaining guests while enjoying the lake view. The primary suite is spacious and comfortable, featuring vinyl flooring, a generous walk-in closet, and a beautifully designed bathroom with dual vanities. The additional bedrooms also feature vinyl flooring, providing both comfort and easy maintenance throughout the home. The two-car garage offers ample space and convenience. Located in the desirable Windermere Isle community, residents enjoy resort-style amenities including a community pool, cabana, playground, and scenic walking trails. The home is also located near top-rated schools, as well as shopping, restaurants, and all the attractions and magic of Walt Disney World just minutes away. If you are looking for quality of life, a prime location, and a beautiful home for your family, this is the perfect opportunity. Schedule your private showing today and come fall in love with this exceptional home.

13542 Gorgona Isle Drive, Windermere

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