Windermere Homes with Pool View

Windermere Homes with Pool View

Welcome to Windermere, Florida, a picturesque gem nestled in Orange County that perfectly marries small-town charm with modern convenience. Known for its stunning lakes and lush landscapes, Windermere offers a serene lifestyle that attracts families, retirees, and everyone in between. With its friendly community atmosphere, delightful local shops, and top-rated schools, it's no wonder that Windermere has become one of Central Florida's most sought-after places to call home.

One of the standout features of Windermere is the abundance of homes with captivating pool views. Imagine waking up each morning to the gentle shimmer of water reflecting the sun, or enjoying a tranquil evening by your own private pool, surrounded by lush greenery. These homes not only provide a luxurious outdoor retreat but also create an inviting atmosphere for entertaining family and friends.

With a variety of architectural styles, from contemporary designs to charming Mediterranean-inspired villas, Windermere’s real estate market offers something for everyone. Many properties boast expansive patios and outdoor living spaces, perfect for soaking up the Florida sunshine or hosting summer barbecues.

Living in Windermere means embracing a lifestyle filled with outdoor activities, from boating on the nearby lakes to exploring the scenic walking trails. Plus, with easy access to Orlando's vibrant attractions, you can enjoy the best of both worlds—peaceful suburban living and thrilling urban entertainment.

Discover your dream home in Windermere today, where every day feels like a vacation with stunning pool views right outside your door!

Newest Windermere Homes with Pool View

8205 Stonemason Court, Windermere
$2,650,000
6 Beds ⋅ 6 Baths ⋅ Keenes Pointe Unit 3 SubDv. ⋅ 34786 Zip Code
Distinctive craftsmanship, open-concept interiors and expansive outdoor living distinguish this custom six-bedroom, six-full-bath residence in Keene’s Pointe. Built in 2016 on a nearly ½-acre homesite, the residence unfolds around a spacious great room appointed with custom dining and entertainment cabinetry. The main level encompasses the primary retreat, a guest bedroom with an ensuite bath, a full pool bath, an office, a kitchen, a generous breakfast nook and a walk-in pantry. Upstairs, three bedrooms with ensuite baths accompany a sixth bedroom suited to use as a studio, playroom or flexible living space, along with a spacious loft featuring a hospitality bar. A mini elevator provides a practical way to transport items between floors, simplifying housekeeping. Custom millwork lends continuity throughout the interiors, from integrated bedroom desks and storage drawers to the great-room entertainment center and a full-wall display case in the study/office. Thoughtfully designed dining cabinetry accommodates table linens, dinnerware, silverware and décor, complemented by a substantial custom china cabinet for glassware near the corner wine room. An integrated buffet offers an elegant setting for serving or displaying fresh flowers and collectibles. Solid-wood interior doors and elaborate custom cabinetry in every closet and the oversized walk-in pantry carry this attention to detail throughout the home. Double-pane windows and sliding doors complement a modern, outward-swinging steel double entry door edged in wood. Additional appointments include upgraded Monogram stainless steel kitchen appliances, whole-house water purification and softening, tankless natural gas water heaters, Lutron lighting controls in the main living areas and a dedicated irrigation well. The generous covered outdoor living area extends the entertaining experience with a complete summer kitchen, including a dishwasher, dinnerware storage, a gas grill and a double-burner cooktop integrated into an oversized island. Positioned beside an oversized conversation pit, the island anchors a lounge-like setting for outdoor gatherings. The private backyard brings together a pool, spa and expansive paver deck in an inviting setting for outdoor entertaining. Just steps from the primary retreat, the spa offers a convenient escape, while an illuminated firepit gathering area provides another setting for evenings outdoors. A mini half-court basketball practice area introduces a recreational dimension, balancing spaces for relaxation, gathering and activity. Located in the highly sought after guard gated lakefront and golf course community of Keene’s Pointe and home of the Golden Bear Club, a private golf and tennis club, residents enjoy a host of amenities including a community boat ramp and a range of parks and playgrounds. Come live the Keene’s Pointe lifestyle!

8205 Stonemason Court, Windermere

703 E 6th Avenue, Windermere
$3,450,000
4 Beds ⋅ 5 Baths ⋅ Windermere SubDv. ⋅ 34786 Zip Code
Exceptional waterfront living on the prestigious Butler Chain of Lakes. Discover an extraordinary expression of waterfront luxury in the charming Town of Windermere, where timeless Tuscan and Mediterranean architecture meets the elegance of refined Florida living. Ideally along the shores of Lake Down, part of the desired Butler Chain of Lakes, this exceptional residence offers a rare opportunity to experience breathtaking water views, sophisticated interiors and an unparalleled boating lifestyle. From moment you arrive, exquisite stone detailing and custom wrought-iron double entry doors establish a sense of architectural distinction. Beyond the grand entrance, soaring ceilings, expansive living spaces, and thoughtfully curated design elements create an atmosphere of understated elegance and effortless sophistication. Designed for grand-scale entertaining and intimate gatherings, the home's gracious formal dining room provides an elegant setting for memorable occasions. At the heart of the residence, an expansive great room seamlessly integrates a gourmet kitchen, casual dining area, custom bar and inviting natural gas fireplace. Framed by captivating waterfront views, this exceptional gathering space offers the ideal balance of luxury, comfort and functionality. The main-level primary suite serves as a private sanctuary, offering serene views of Lake Down and a beautifully appointed en-suite bath featuring dual vanities, two spacious walk-in closets, a luxurious jetted soaking tub and an oversized travertine shower. An additional main-level bedroom provides exceptional versatility, ideally suited for guest accommodations, a private executive office, fitness studio or creative retreat. Upstairs, two generously proportioned bedrooms provide additional privacy and comfort. Thoughtfully reconfigured from the home's original three-bedroom upper-level layout, one of these bedrooms has been transformed into an exceptionally spacious retreat, complete with its private balcony. Abundant storage throughout the residence, a spacious laundry room with a recently updated washer and dryer, and a three-car garage further enhance the home's everyday convenience. Beyond the interiors, an extraordinary outdoor oasis awaits. An expansive covered and screened lanai, custom swimming pool, lush, mature landscaping and picturesque waterfront surroundings create a private resort-inspired setting. Whether hosting elegant outdoor gatherings, enjoying a leisurely afternoon poolside, or simply taking in the tranquil beauty of the lake, every moment invites relaxation and enjoyment. For boating enthusiasts, the property's enclosed boathouse offers a distinctive waterfront amenity, featuring a protected boat area and an inviting screened retreat. With direct access to the 13 interconnected lakes of the Butler Chain, an exceptional lifestyle of boating, waterskiing, wakeboarding, paddleboarding and waterfront exploration awaits just beyond your doorstep. Adding to its appeal is the timeless charm of Windermere itself. Enjoy the town's celebrated weekly farmers market, boutique shops, inviting restaurants, local brewery, wine market and cherished community events. All this is complemented by convenient access to Orlando's premier shopping, acclaimed dining destinations, world-renowned attractions and Orlando International Airport.

703 E 6th Avenue, Windermere

6024 Greatwater Drive, Windermere
$3,250,000
5 Beds ⋅ 6 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Ideally located within the highly desirable, guard-gated Keene’s Pointe community and situated on the 17th fairway of the Jack Nicklaus-designed Golden Bear Golf Course, this stunning, custom-built estate with 3-car garage has outstanding curb appeal and is cleverly designed to effortlessly surround a center courtyard whilst still availing of sweeping views of the golf course. On arrival, the residence is accessed via a double wrought iron gate with solid wooden doors leading to the California/Mediterranean-style courtyard immediately setting a scene of grandeur and providing both a welcoming entryway to the home as well as coveted al fresco living, dining & entertainment spaces. Featuring a tranquil water fountain, a spa anchored by a custom fireplace, and a summer kitchen with a full wet bar, enjoy the Florida lifestyle seamlessly blending indoor and outdoor living whilst retaining a true sense of privacy. The home itself spans 6,370 square feet of air-conditioned space and provides the ultimate in elegance and luxury living. A double door entrance opens to a 2-story foyer with impressive grand staircase. Elevated finishes are abound and include rich hardwood flooring, crown molding, plantation shutters, and elegant tongue-and-groove ceilings. The gourmet kitchen with separate breakfast area is a chef's dream, with ample cabinetry, sleek quartz countertops and backsplash, high-end Thermador appliances, a double oven, and a custom range hood, all perfectly situated opposite a fully equipped wet bar and generous family room with a double-sided fireplace enhanced by views over the golf course and with sliding glass doors providing direct access to the yard. A raised dining room provides a more formal eating space. The thoughtful layout features 5 bedrooms, including a secluded 1st-floor owner's retreat that spans an entire wing with full ensuite bathroom, a sitting area and its own completely private courtyard, a secondary 1st-floor guest suite with courtyard access (currently used as a music room), and an upstairs mother-in-law suite with balcony. Designed for modern living, the estate also boasts a private executive office, a home theater/media room, a large upstairs bonus room/flex space, a loft with a built-in entertainment center and wrap around balconies adorn both the front and back side of the house. The resort-style backyard is an outdoor oasis, showcasing a sparkling heated pool with water features, professional evening uplighting, and both covered & open outdoor lounge seating spaces overlooking the lush, mature landscaping of the yard and views of the fairway. Recent upgrades in the home include Anderson windows, 2 HVAC units and all HVAC units in the home have UV light system, 2 water heaters and water softener, new driveway & home side paths, newer pool, spa and fountain equipment and newer painted interior with freshly painted exterior Oct 2026. Residents enjoy exclusive neighborhood amenities, including community playgrounds, basketball courts, and private boat ramp access to Lake Burden, with optional club memberships available for the fitness center, clubhouse, swimming, tennis courts, and championship golf course.

6024 Greatwater Drive, Windermere

6518 Sawyer Shores Lane, Windermere
$2,190,000
5 Beds ⋅ 6 Baths ⋅ Sawyer Shores Sub SubDv. ⋅ 34786 Zip Code
Virtually Staged. Under Construction. Estimated completion: January 2027. Commanding architecture, soaring interiors and access to Lake Sawyer define this new contemporary residence in sought-after Windermere. Set on a wide 0.39-acre lot, its striking facade makes an immediate impression, while approximately 100 feet of canal frontage opens the door to a lifestyle on the water. As the first home along the canal from the lake, the property enjoys a short waterway connection to Lake Sawyer, with an existing floating platform designed for a personal watercraft. Offering 3,582 square feet of conditioned living space and 4,865 total square feet, the home features five bedrooms, each with an en-suite bathroom, plus a powder room, dedicated office and three-car garage. Twelve-foot ceilings on both floors and a dramatic double-height space create an exceptional sense of scale. The open layout connects the kitchen, dining and living areas for effortless everyday living and entertaining, while the main-floor primary suite offers a comfortable retreat with a walk-in closet and spacious bathroom. Extensive cabinetry and built-ins bring a tailored aesthetic throughout the home. Planned finishes include stone countertops, porcelain tile and warm wood-look flooring, complemented by a gas cooktop and an electric fireplace. The design balances contemporary presence with inviting spaces that feel comfortable to live in. Outside, a private heated pool and covered rear lanai with a grill and sink set the scene for relaxed afternoons and evenings with guests. Planned artificial turf around the pool, hardscape surfaces and landscaping complete an outdoor setting designed for enjoyment with easy upkeep. With no HOA, this property pairs the appeal of new construction with a waterfront setting close to the lake. Within walking distance of Windermere Preparatory School, ranked No. 1 among private high schools in Orange County by Niche for 2027, and conveniently located near Windermere High School. Public schools listed for this address are Windermere Elementary, Bridgewater Middle and Windermere High, all earning an A in Florida's 2026 school grades. Buyers should verify current school zoning. Limited personalization may be considered, subject to builder approval and construction timing. Discover a home where the arrival is memorable, the interiors feel expansive and time on Lake Sawyer can become part of everyday life. Images include architectural renderings and virtual staging; final materials and finishes may vary.

6518 Sawyer Shores Lane, Windermere

11532 Waterstone Loop Drive, Windermere
$2,199,000
4 Beds ⋅ 6 Baths ⋅ Waterstone SubDv. ⋅ 34786 Zip Code
SINGLE STORY LIVING and PRIVATE PEDESTRIAN-GATED ACCESS to WINDERMERE PREPARATORY SCHOOL from within the community distinguish this custom Waterstone home. Built in 2014 and located behind a staffed, guard-gated entrance, the residence offers approximately 4,169 square feet, four bedrooms, four full baths, two half baths, and a three-car garage. Two stately palms welcome you to the beautifully landscaped 0.44-acre homesite, while landscape lighting highlights the grounds after sunset. From the moment you enter, the view opens to the CENTRAL COURTYARD, SALTWATER POOL, and SPA. Direct access from the kitchen, family room, and primary suite makes the courtyard part of daily life. Covered lanais, generous lounging areas, a summer kitchen with a full-size motorized screen, and an outdoor fireplace provide space to gather and dine outdoors. The courtyard has been freshly painted, and the travertine pavers were recently sealed. Inside, soaring ceilings, tray details, crown molding, and expansive windows bring light and courtyard views into the living spaces. The kitchen features Wolf and Sub-Zero appliances, rich wood cabinetry, dual islands, bar seating, and a concealed walk-in pantry. The spacious primary suite includes hardwood flooring, a sitting area, two expansive custom walk-in closets, and a bath with a soaking tub, oversized rainfall shower, and generous vanity space. An adjoining flex room can serve as a home office, gym, or private retreat. Additional features include two newer air-conditioning units serving the multizone HVAC system, a sound system throughout the indoor and outdoor living areas, a whole-house Lorex camera system, a porte-cochère, and an expansive paver driveway. Waterstone is near Windermere High School, with convenient access to Winter Garden Village, Lakeside Village, Walt Disney World, and major Orlando routes. Schedule a private showing to experience this distinctive Windermere courtyard home.

11532 Waterstone Loop Drive, Windermere

5186 Vardon Drive, Windermere
$4,395,000
6 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence with contemporary interiors and expansive views across the course. Beyond the private entry gate to the property, a long, dramatic drive leads to the circular motor court anchored by a distinctive tiered fountain, creating an impressive arrival to this beautifully reimagined Isleworth estate. Inside, soaring ceilings and a dramatic two-story foyer introduce beautifully updated living spaces, where new flooring, refined architectural details and distinctive backlit feature walls create a fresh, elevated aesthetic. Primary living spaces include formal living and dining rooms, a kitchen with casual dining, and a home office. The six-bedroom residence offers two bedrooms on the main level, one on the lower level and three on the upper level. The expansive primary suite is includes a large bath finished with oversized floor-to-ceiling stone tile, a freestanding soaking tub, walk-in shower and dual-sink vanity. Designed for year-round enjoyment, the outdoor living experience begins in the enclosed Florida room and unfolds onto a sprawling pool deck overlooking the golf course. A large pool is complemented by an intimate oasis dining area surrounded by a pool moat, a separate sundeck and a covered outdoor grilling area, creating multiple spaces for entertaining, dining and relaxing. With its exceptional arrival, thoughtfully renovated interiors and expansive indoor-outdoor living, this distinctive estate offers a refined setting within one of Isleworth’s most sought-after golf-course locations.

5186 Vardon Drive, Windermere

4243 Isabella Circle, 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

8142 Tibet Butler Drive, Windermere
$2,685,000
5 Beds ⋅ 7 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Expansive golf course and water views abound from this impressive Keene’s Pointe estate residence, located on the 3rd green of the renowned Jack Nicklaus Signature Golf Course. Be welcomed by a grand foyer that flows seamlessly into a formal dining room: a refined, inviting space that blends timeless architectural character with luxury finishes. Framed by exposed wood beams, arched wall details, and wrought iron accents, the room feels warm yet grand. Nearby, the living room offers a more relaxed ambiance that elevates everyday living while providing a sophisticated backdrop for entertaining. An expansive primary bedroom and bathroom suite, office, and pool bath are located off the foyer. The chef’s kitchen feature stainless steel appliances—including a double oven and built in refrigerator—that create a seamless, upscale workflow, while the adjacent breakfast nook provides a sunlit place to enjoy morning coffee. A secondary suite on the first floor is perfect for visiting guests. Three upstairs bedroom suites share a common space for homework or socializing and a large bonus room with bar and balcony is a favorite place to entertain friends. A designated home theater is perfect for relaxing while enjoying favorite shows. Outside is a summer kitchen, fireplace, and lounge area for enjoying the Florida weather. The large resort-style pool and spa with waterfall complete the setting. Home is located across the street from the golf course driving range. Residents of Keene’s Pointe enjoy a sought-after country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, dining, and a vibrant social calendar—making this one of Central Florida’s most desirable places to call home.

8142 Tibet Butler Drive, Windermere

2540 Hempel Cove Ct, Windermere
$1,299,000
5 Beds ⋅ 3 Baths ⋅ Lake Down Cove SubDv. ⋅ 34786 Zip Code
Virtually Staged. Set on just over an acre in Windermere, this updated 5-bedroom, 3-bath pool home offers 3,356 square feet of living space, plus a separate flex/bonus room that can be used as a media room, game room, office or additional living space. Located on a cul-de-sac in Lake Down Cove, the property offers something increasingly hard to find in Windermere: an updated home with a private pool, a flexible floor plan and more than an acre of land. Inside, high ceilings and large windows bring in plenty of natural light, while large-format marble-look porcelain tile runs throughout the main living areas. The spacious family room features a modern linear electric fireplace and opens to the kitchen and casual dining area, with views of the pool and backyard. A separate dining room is located just off the entry, and an interior Juliet balcony from the second floor overlooks the family room. The updated kitchen features dark shaker-style soft-close cabinetry, quartz countertops, a large island, farmhouse sink and glass tile backsplash. A six-burner ZLINE gas range with griddle, pot filler and stainless steel hood anchors the cooking area, along with double ovens, a microwave drawer and stainless steel appliances. Three of the five bedrooms are located downstairs, including the primary suite. The primary bedroom overlooks the pool and features crown molding, two walk-in closets and double doors leading outside. The primary bathroom includes dual vanities with quartz countertops, a freestanding soaking tub and a large frameless glass shower finished with marble-look porcelain tile. Two additional bedrooms and a second full bathroom are also downstairs, with one bedroom well suited for use as a home office. The second bathroom has direct access to the pool area. Upstairs are two additional bedrooms, a full bathroom and a separate flex room that could be used as a media room, game room, office or additional living area. The upstairs bathroom features a dual vanity with quartz countertops, a tub/shower combination and updated finishes. One of the upstairs bedrooms also features a private outdoor balcony and an interior Juliet balcony overlooking the family room below. Outside, the 1+ acre lot provides plenty of room to enjoy the property. The private pool is surrounded by a large patio with a partially covered area, while the fenced backyard offers mature trees and generous open space. The outdoor kitchen includes a built-in grill, refrigerator, sink, stone surround and counter space, and a wood-burning fire pit adds another gathering area in the backyard. Additional features include a downstairs laundry room with quartz countertops, sink and extensive cabinetry, plus an oversized two-car garage with workspace and additional storage. With five bedrooms plus a flex room, 3,356 square feet, an updated interior, private pool and more than an acre of land, this Windermere home offers an uncommon amount of space both inside and out. Conveniently located near shopping, dining, community events and major roadways, with easy access throughout Windermere and the greater Orlando area.

2540 Hempel Cove Ct, Windermere

5524 Worsham Court, 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

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