Windermere Homes with Pool Amenities

Windermere Homes with Pool Amenities

Welcome to Windermere, Florida—a picturesque gem nestled in Orange County, just a stone’s throw away from the vibrant city of Orlando. Known for its serene lakes, lush landscapes, and charming community, Windermere offers a tranquil escape while keeping you close to the excitement of Central Florida. With its quaint downtown area, adorned with boutique shops and delightful eateries, this town is a perfect blend of small-town charm and modern convenience.

Windermere is renowned for its stunning homes, many of which boast luxurious pool amenities that transform your backyard into a private oasis. Imagine stepping out onto your patio, the sun shining down as you dive into your sparkling pool, or hosting summer barbecues with friends and family while the kids splash nearby. Homes with pool amenities in Windermere are designed for both relaxation and entertainment, featuring spacious layouts, contemporary designs, and beautifully landscaped yards.

Living in Windermere means embracing a lifestyle filled with outdoor adventures. With numerous parks, scenic trails, and access to the pristine Butler Chain of Lakes, you’ll find endless opportunities for boating, fishing, and enjoying nature. The community is also known for its top-rated schools and friendly neighborhoods, making it a perfect place for families to thrive.

Whether you’re looking for a peaceful retreat or a vibrant community, Windermere’s homes with pool amenities provide the ideal setting for your next chapter. Dive into the Windermere lifestyle and discover the perfect blend of comfort, luxury, and community spirit. Your dream home awaits!

Newest Windermere Homes with Pool Amenities

8214 Serenity Spring Drive Unit 2405, Windermere
$350,000
3 Beds ⋅ 3 Baths ⋅ Oasis Cove 2/Lakeside Village Ph X SubDv. ⋅ 34786 Zip Code
Live about as close to the magic as you can get without a Disney address. This home in gated Oasis Cove sits just 3 minutes from Disney property, so park days, dinner reservations, and fireworks nights are a quick drive instead of a trip. The 3 bed, 2.5 bath layout offers 1,512 sq ft and a 1-car garage, with upgraded flooring on the stairs and throughout the upper level. The HOA covers the roof, lawn care, and water, so electricity is your only utility bill, and the HVAC was replaced in 2024. Spend your free time at the resort-style pool and community amenities, or at the parks down the road, instead of maintaining a home. It works equally well for full-time residents and seasonal owners. Zoned for A-rated schools from elementary through high school. Buyer to verify school assignment, HOA coverage.

8214 Serenity Spring Drive Unit 2405, Windermere
5638 Nectarine Drive, Windermere
$1,550,000
5 Beds ⋅ 5 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code
BEAUTIFUL LAKE CAWOOD VIEWS AND WATER ACCESS SET THE SCENE FOR THIS NEWLY BUILT WINDERMERE HOME! Situated on a PREMIUM LOT in Lake Cawood Cove, this residence welcomes you with a SPACIOUS COVERED FRONT PORCH, thoughtfully selected upgrades, and an elegant, spacious design. This Ashton Woods DUVAL FLOOR PLAN offers approximately 3,612 square feet of living space, 5 BEDROOMS, 4 FULL BATHROOMS, 1 HALF BATHROOM, and a 3-CAR TANDEM GARAGE, with the opportunity to build your own PRIVATE BOAT DOCK. Inside, 10-FOOT FIRST-FLOOR CEILINGS, 9-FOOT SECOND-FLOOR CEILINGS, and 8-FOOT DOORS enhance the spacious feel. LUXURY VINYL PLANK FLOORING extends throughout the living areas, bedrooms, and staircase, while the bathrooms and laundry room feature tile flooring. At the heart of the home, the GOURMET KITCHEN showcases UPGRADED CABINETRY EXTENDING TO THE CEILING, creating a beautifully finished appearance with abundant storage. A SPACIOUS ISLAND with additional cabinetry on the back, an upgraded appliance package, and a customized pantry layout combine style with everyday functionality. The kitchen connects seamlessly to the breakfast area and an impressive GREAT ROOM WITH A SOARING 2-STORY CEILING. Windows welcome natural light and capture views toward the lake, creating an inviting setting for everyday living and entertaining. A separate dining room provides additional space for special gatherings. The FIRST-FLOOR BEDROOM SUITE includes a closet and private full bathroom, offering a comfortable retreat for guests. Upstairs, the spacious PRIMARY SUITE features a TRAY CEILING, a LARGE WALK-IN CLOSET, separate vanities, and a walk-in shower. An additional bedroom suite includes its own full bathroom, while two more bedrooms share another full bathroom. A versatile LOFT offers space for a lounge, study, or recreation area, and the conveniently located upstairs laundry room completes the second floor. Carefully selected enhancements include UPGRADED BATHROOM TILE with wall tile extending to the ceiling, LIGHTING UPGRADES, and wood stair railings. Additional features include sound insulation in selected walls, FOAM INSULATION in the block walls of the living space and garage, and prewiring for ceiling fans, security, and two additional wireless access points. An UPGRADED FRENCH DOOR opens to the COVERED LANAI, where beautiful water views and a conservation area toward Lake Cawood create a peaceful, natural backdrop. At the rear of the home, BEAUTIFUL SUNSET VIEWS OVER THE WATER provide a picturesque setting for relaxing evenings and outdoor gatherings. SUMMER KITCHEN PLUMBING AND ELECTRICAL PROVISIONS provide the flexibility to personalize your outdoor entertaining space. Enjoy convenient access to Windermere Preparatory School, Windermere High School, Publix, Aldi, shopping, dining, Winter Garden Village, the 429 Expressway, and Central Florida’s world-famous theme parks. With its premium setting, distinctive finishes, and generous living spaces, this newly built residence offers an exceptional opportunity to enjoy the Windermere lifestyle. Schedule your private showing today! VIDEO, 3D TOUR, AND FLOOR PLAN LINKS ABOVE.

5638 Nectarine Drive, 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
8325 Vivaro Isle Way, Windermere
$799,900
4 Beds ⋅ 3 Baths ⋅ Windermere Isle SubDv. ⋅ 34786 Zip Code
Virtually Staged. **POND VIEWS & DISNEY FIREWORKS!** Prepare to be impressed by this beautifully appointed 4-bedroom, 3-bath home in sought-after Windermere Isle, offering an inviting blend of stylish living, thoughtful upgrades, and a picturesque pond backdrop with a fountain and conservation views. Designed for both everyday comfort and entertaining, the open floor plan is enhanced by a decorative coffered ceiling in the dining room and a custom built-in entertainment feature that adds architectural interest and a polished focal point to the family room. The kitchen is equally impressive with granite countertops, tile backsplash, stainless steel appliances, abundant cabinetry, and a large center island, complemented by an adjacent informal dining area for casual meals. Everyday functionality is thoughtfully incorporated with a built-in drop zone just inside the garage entry, conveniently positioned near the walk-in pantry and kitchen. A first-floor bedroom with a full bath nearby provides wonderful flexibility for guests, while a creative nook beneath the stairs features a built-in desk, storage, and chalkboard wall, offering a fun space for homework, crafts, or play. Upstairs, **laminate flooring** extends throughout the stairs and entire second floor, where a spacious loft provides another inviting gathering space. The primary suite offers a relaxing retreat with two large walk-in closets and a beautifully appointed bath featuring dual vanities, a freestanding soaking tub, and glass-enclosed shower. The outdoor setting truly sets this home apart. A screened lanai with summer kitchen overlooks the fenced backyard and tranquil pond with fountain, creating the perfect backdrop for dining, entertaining, or simply unwinding while enjoying Disney fireworks in the distance. The home is also equipped with solar panels, while the two-car garage features an EV charger and overhead storage. Upgraded landscaping enhances the home’s curb appeal. Residents of Windermere Isle enjoy a resort-style community swimming pool with poolside cabana and playground, while HOA fees include lawn care, cable TV, and internet. Conveniently located near Walt Disney World, world-class shopping, dining, and major roadways. With its generous living spaces, versatile floor plan, beautiful pond setting, and desirable community amenities, this exceptional home offers an outstanding opportunity to enjoy the Windermere lifestyle!

8325 Vivaro Isle Way, Windermere
13731 Calera Alley, Windermere
$465,000
3 Beds ⋅ 3 Baths ⋅ Vineyards/Horizons West Ph 2b SubDv. ⋅ 34786 Zip Code
Welcome home to this highly upgraded, move-in ready outside end unit in the Vineyards of Horizons West. This unit features a fenced side yard with patio, walkway to garage, front porch and landscaping, pond and open views. The front of the unit has a quiet courtyard setting. Inside you will find a beautiful large gourmet kitchen w/upgraded cabinets and sink, including a large kitchen island. A very large open great room and dining area. The first floor is wood look "porcelain tile" with sealed grout for minimal upkeep. Downstairs also features a spacious half bath and a large storage area under the stairs and separate laundry area. The garage is oversized with a finished floor. Upstairs are three bedrooms and a loft. Bath in the primary has been upgraded to frameless glass, a large spacious closet with extra racks added. $48K in upgrades from the builder when new. Pond and open space views from the first and second floor make the setting of this unit even more appealing. A quiet community with a park-like atmosphere, community pool and playground, and walking distance to Windermere High School.

13731 Calera Alley, Windermere
5021 Carillon Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ Summerport SubDv. ⋅ 34786 Zip Code
Welcome to this beautiful home in a highly desirable community known for its top-rated schools and beautifully maintained surroundings. Lush landscaping, graceful palm trees, and a covered front porch create a warm welcome. Inside, the foyer opens to a formal dining room with an elegant chandelier and a home office enclosed by glass French doors. Neutral tones, arched walkways, and wood laminate flooring are found throughout the main living areas. The spacious, open floor plan flows into the kitchen featuring shaker cabinets, granite countertops, a decorative backsplash, stainless steel appliances, a wine rack, and a large custom pantry with built-in storage. A dedicated laundry area with folding space adds convenience. The light-filled living room opens to a breakfast nook with a stylish rattan light fixture, bay window seating, and sliding glass doors leading to the pool. The private primary suite features double-door entry, a custom walk-in closet with extensive built-ins, and a spa-inspired bathroom with dual vanities, a large soaking tub, and a separate glass-enclosed shower. Three additional bedrooms and two full guest bathrooms with tub/shower combinations provide plenty of space for family and guests. Step outside to your own tropical retreat, complete with a screened-in pool, shaded gazebo, and vinyl fencing for added privacy. Updates include HWT 2023, HVAC 2019, and roof replacement in 2020. Conveniently located near entertainment, shopping and dining at Winter Garden Village, Walt Disney World, and major roadways including Florida's Turnpike, this home offers both comfort and accessibility. Schedule your private showing today!

5021 Carillon Lane, Windermere
14038 Bluebird Park Road, Windermere
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Summerport Ph 02 SubDv. ⋅ 34786 Zip Code
Rare Windermere opportunity with water on TWO sides... Direct waterfront on one, and premium scenic water views on the other. Set on a premium 1.08-acre homesite with pond access and only one neighboring residence, this 4-bedroom, 4-bath home offers privacy, panoramic views, a private pool and spa, and nearly 3,400 square feet of living space. With more than $70,000 in recent improvements, the property combines an expansive indoor layout with exceptional outdoor living. Inside, soaring ceilings, designer finishes, and a grand staircase create a striking first impression. Designed for both everyday living and entertaining, the home features two spacious living areas, a well-appointed kitchen, formal dining room, butler’s pantry, dedicated office, and a custom home theater. Outfitted with a Sony 4K projector, Philips 110-inch film screen, Dolby Atmos surround-sound speakers, and seating for eight, the theater delivers an exceptional cinematic experience at home. Recent improvements include fresh interior paint, custom accent walls, a striking fireplace feature wall, updated designer lighting, a built-in Sub-Zero/Viking refrigerator, an undercounter ice maker, and reverse-osmosis water filtration. Additional highlights include a 2021 architectural roof and gutters, two HVAC systems replaced in 2020, and a split three-car garage with a climate-controlled third bay currently configured as a fitness space. Step outside to a private waterfront retreat with a pool and spa, stone firepit, expansive brick-paver lanai, and custom MegaView screen enclosure. The outdoor setting showcases panoramic water views with minimal visual obstructions, while the spacious driveway and welcoming front porch add to the home’s functionality. The backyard also provides views of Disney fireworks. Summerport amenities include a neighborhood park, playground, community beach, dock, walking and biking paths, clubhouse, community pool, fitness center, tennis and basketball courts, and gathering spaces. This Windermere residence offers a rare combination of acreage, privacy, direct waterfront, scenic water views, and resort-style outdoor living.

14038 Bluebird Park Road, Windermere
14500 Bridgewater Crossings Boulevard, Windermere
$400,000
4 Beds ⋅ 3 Baths ⋅ Tennyson Pk/Summerport SubDv. ⋅ 34786 Zip Code
Morning coffee at Foxtail, an evening walk for Kelly’s Homemade Ice Cream, and a move-in-ready home waiting when you get back. At 14500 Bridgewater Crossings Boulevard, that can be your everyday routine. Located in Windermere’s Summerport community, this 4-bedroom, 2.5-bath townhome combines a convenient neighborhood setting with fresh interior paint throughout, new luxury vinyl plank flooring upstairs, and no carpet anywhere in the home. A main-floor primary suite is a standout feature, offering the convenience of having your bedroom and private bathroom downstairs, with three additional bedrooms, a full bathroom, and a loft upstairs. Whether you need room for guests, a dedicated home office, or a second gathering space, the layout gives you options. Downstairs, the living and dining areas, kitchen, and guest half bath keep everyday activities on the main level. A courtyard provides an outdoor spot for plants, coffee outside, or unwinding at the end of the day, while a covered walkway connects the home to the two-car garage. And the neighborhood gives you plenty of reasons to step outside. Walk across the street for your favorite coffee or a scoop of ice cream, enjoy nearby Summerport Park, and appreciate the convenience of having Keene’s Crossing Elementary close by. Summerport’s community pool, clubhouse, fitness center, tennis courts, playgrounds, and walking paths make it easy to fit recreation into your routine without planning an entire day around it. Beyond the neighborhood, Publix at Cornerstone at Summerport keeps grocery runs convenient, while Winter Garden Village and Hamlin offer nearby shopping, restaurants, and entertainment. Walt Disney World is also within easy reach, whether your plans call for a full park day or a spontaneous evening out. With fresh updates already completed, a main-floor primary suite, and neighborhood favorites just a walk away, this home is ready for you to settle in and start enjoying everything beyond the front door. Schedule your private showing today.

14500 Bridgewater Crossings Boulevard, Windermere
5650 Nectarine Drive, Windermere
$1,475,000
5 Beds ⋅ 5 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code
NEWLY BUILT HOME WITH LAKE CAWOOD ACCESS ON APPROXIMATELY 1.70 ACRES! Discover refined lake living in this Ashton Woods Duval residence in Lake Cawood Cove, Windermere, with the opportunity to build your own PRIVATE BOAT DOCK. With approximately 3,612 square feet of living space, 5 BEDROOMS, 4 FULL BATHROOMS, 1 HALF BATHROOM, and a 3-CAR TANDEM GARAGE, this home combines generous space with thoughtfully selected upgrades. 10-FOOT CEILINGS ON THE FIRST FLOOR, 9-FOOT CEILINGS ON THE SECOND FLOOR, and 8-FOOT DOORS enhance the spacious feel. NEW LUXURY VINYL PLANK FLOORING extends throughout the home, including the staircase, while the bathrooms and laundry room feature tile flooring. The impressive great room features a SOARING 2-STORY CEILING, creating an open, airy atmosphere that connects seamlessly to the GOURMET KITCHEN and breakfast area. Designed for everyday enjoyment and entertaining, the kitchen features a SPACIOUS ISLAND, an upgraded appliance package, UPGRADED CABINETRY, additional storage cabinets at the back of the island, and a customized pantry layout. A separate dining room provides space for special gatherings. The FIRST-FLOOR BEDROOM SUITE includes a closet and private full bathroom, creating a comfortable retreat for guests. Upstairs, the spacious PRIMARY SUITE features a TRAY CEILING, a LARGE WALK-IN CLOSET, and a private bathroom with separate vanities and a walk-in shower. An additional bedroom suite includes its own full bathroom, while 2 more bedrooms share another full bathroom. A versatile LOFT and conveniently located laundry room complete the second floor. Carefully selected enhancements include UPGRADED BATHROOM TILE with wall tile extending to the ceiling, upgraded toilets, LIGHTING UPGRADES, and wood stair railings. Additional features include sound insulation in selected walls, FOAM INSULATION in the block walls of the living space and garage, and prewiring for ceiling fans, security, and 2 additional wireless access points. An UPGRADED FRENCH DOOR opens to the COVERED LANAI, creating an inviting connection to outdoor living. SUMMER KITCHEN PLUMBING AND ELECTRICAL PROVISIONS provide the flexibility to customize your outdoor entertaining space. A conservation area toward Lake Cawood provides a peaceful, natural backdrop. Enjoy convenient access to Windermere Preparatory School, Windermere High School, Publix, Aldi, shopping, dining, Winter Garden Village, the 429 Expressway, and world-famous theme parks. With its desirable Windermere location, stylish finishes, and spacious layout, this newly built home provides an exceptional opportunity to enjoy the Florida lifestyle. Schedule your private showing today! VIDEO, 3D TOUR, AND FLOOR PLAN LINKS ABOVE.

5650 Nectarine Drive, Windermere
11267 Grander Drive, Windermere
$435,000
3 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph 2 #35 36 SubDv. ⋅ 34786 Zip Code
Stunning modern townhome in the desirable Lake Burden community of Windermere! This beautifully designed 3-bedroom, 2.5-bathroom corner-lot townhome offers 1,743 sq ft of living space with all bedrooms upstairs, including a primary suite with walk-in closet. The modern kitchen features dark wood cabinets, granite countertops, a spacious island with room for three barstools, and slate stainless steel GE appliances. High ceilings and an open floor plan create a bright, inviting space perfect for entertaining. Two-car garage. Currently tenant-occupied with a lease through 12/31/2026 - a great opportunity for investors seeking immediate rental income, or for buyers planning ahead. Short walk to the community clubhouse with a large resort-style pool, shaded seating and picnic areas. Lake Burden is a nature lover's paradise featuring a fishing pier, a scenic lake with a mile-long walking and biking trail, outdoor fitness stations, playground and tennis courts, with trails connecting to Downtown Windermere. Zoned for Sunset Park Elementary, Horizon West Middle and Windermere High School. Short-term rentals are not permitted. Schedule your showing today!

11267 Grander Drive, Windermere
8276 Maritime Flag St Unit 1204, Windermere
$324,900
3 Beds ⋅ 2 Baths ⋅ Lakeside/Lk/Windermere Ph 12 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome to this beautiful 3-bedroom, 2-bathroom first-floor condo in the desirable Lakeside at Lake Windermere community! Offering an attractive combination of location, comfort, and investment potential, this property is an excellent opportunity for both homeowners and investors looking for a rental property in the heart of Central Florida. Conveniently located near Walt Disney World, Windermere, shopping, restaurants, and major roadways including I-4 and the 429, this condo offers easy access to the area's top attractions, employment centers, and everyday conveniences. Its location also makes it an appealing option for renters seeking proximity to Disney, the Windermere area, and nearby schools. Inside, you'll find a functional open-concept split floor plan with quality laminate flooring throughout. The kitchen features beautiful wood cabinetry, granite countertops, modern appliances, and plenty of counter space. The spacious dining area and great room create an inviting setting for entertaining family and friends. The generously sized primary bedroom accommodates a king-size bedroom suite and features a walk-in closet. The primary bathroom includes dual sinks, ample cabinetry, and a bathtub/shower combination. Two additional bedrooms are situated on the opposite side of the condo, conveniently located near the second full bathroom and laundry closet. Step through the sliding glass doors to enjoy your private screened-in patio, perfect for relaxing and enjoying Florida's year-round outdoor lifestyle. Residents enjoy a variety of community amenities, including a gated entrance, valet trash service, a beautiful clubhouse, a resort-style destination pool, a sand volleyball court, and a barbecue area. An Excellent Investment Opportunity you don't want to miss!!

8276 Maritime Flag St Unit 1204, Windermere
12785 Westside Village Loop, Windermere
$769,000
4 Beds ⋅ 4 Baths ⋅ Westside Village SubDv. ⋅ 34786 Zip Code
NEW PRICE! MOVE-IN READY WINDERMERE HOME WITH PEACEFUL CONSERVATION VIEWS + $12,000 DECOR/RATE BUY DOWN CREDIT! Discover the perfect blend of comfort, style, and location in desirable Westside Village! This beautifully maintained 4-bedroom, 3.5-bath home features an inviting open-concept floor plan, classic tile roof, professionally landscaped yard, and spacious front porch. Enjoy tranquil conservation views from the backyard, creating a peaceful backdrop for relaxing or entertaining. The light-filled kitchen is designed for everyday living and effortless entertaining, featuring granite countertops, stainless steel appliances, and an oversized center island with abundant storage and seating. The kitchen flows seamlessly into the living room and breakfast nook, while French doors open to the patio for easy indoor-outdoor living. Enjoy a $12,000 decor credit toward a flooring upgrade and EV charger, offering an opportunity to personalize your home and add modern convenience. Westside Village offers an exceptional lifestyle with resort-style amenities, including a community pool, clubhouse, playground, paved walking trails, and scenic water features. Conveniently located near top-rated schools, shopping, dining, major highways, and just minutes from Walt Disney World, this home combines peaceful surroundings with easy access to everything Central Florida has to offer.

12785 Westside Village Loop, Windermere
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