Windermere Homes with Recreation Facilities Amenities

Windermere Homes with Recreation Facilities Amenities

Welcome to Windermere, Florida—a picturesque town nestled in the heart of Orange County. Known for its serene lakes and lush landscapes, Windermere offers a unique blend of small-town charm and modern conveniences. Surrounded by the stunning Butler Chain of Lakes, residents enjoy a tranquil lifestyle while being just a stone's throw away from the vibrant attractions of Orlando. With its tree-lined streets, friendly neighborhoods, and a strong sense of community, Windermere is the perfect place to call home.

But what truly sets Windermere apart is its array of homes featuring exceptional recreational facilities and amenities. Many properties in this enchanting area come equipped with private pools, fitness centers, and playgrounds, making it easy for families to stay active and engaged. Whether you prefer a leisurely afternoon by the pool or an invigorating workout at the gym, these homes cater to your every need.

Additionally, Windermere is a haven for outdoor enthusiasts. The town boasts numerous parks, walking trails, and access to water sports, allowing residents to embrace the sunny Florida lifestyle to the fullest. The close-knit community frequently hosts events and activities, fostering connections among neighbors and creating a warm, welcoming atmosphere.

If you're searching for a home that offers not only comfort and luxury but also a vibrant lifestyle filled with recreational opportunities, look no further than Windermere. Experience the perfect blend of tranquility and adventure in this charming Florida town, where every day feels like a vacation.

Newest Windermere Homes with Recreation Facilities Amenities

4936 Wise Bird Drive, Windermere
$535,000
4 Beds ⋅ 3 Baths ⋅ Summerport Creeks Run SubDv. ⋅ 34786 Zip Code
Welcome home to your immaculate and move in ready single story home in desirable Summerport with A-rated schools and the Keene's Crossing Elementary School conveniently located a bike ride away within the community and Windermere High School across the street. School commute convenience at its best!!! This light & bright functional floor plan has been recently painted inside and out with a brand new roof in 2025 and new HVAC in 2020, and is the ideal first home for a growing family, a vacation home to get away from those cold winters, or even a retirement home or investment property. From the minute you enter through the covered front porch you are greeted by upgraded Luxury Vinyl Plank flooring through all the living areas and bedrooms with ceramic tile floors in the kitchen and wet areas. The formal living and dining rooms are located across from one another and can serve as the desired flex space that you need making them ideal as a home office, media or game room, home theatre or play room. The kitchen is conveniently located adjacent to the formal living room and features upgraded Quartz counter tops with new appliances in 2021 with a natural gas stove and a brand new dishwasher in 2026. You will literally be cooking with gas in this home...The inviting family room opens up to the kitchen making this the ideal floor plan to entertain your guests and serve your favorite culinary creations on the breakfast bar. The breakfast nook offers serene views of your private wooded backyard. Your master retreat is privately tucked away in the back of the home and features serene wooded views of your private back yard, a spacious walk-in closet and an en suite bath with dual vanities, a garden tub, separate shower and bathrooms stalls. The adjacent bedroom with full bath is ideal for a close by nursery or home office. Bedrooms 2 and 3 are located on the opposite side of the home with a shared bath; ideal as guest bedrooms or the private space that your teenagers need. Long hot showers are as economical as it gets thanks to the natural gas water heater from 2020. Summerport community offers a clubhouse with a hall featuring a cozy fireplace and fully equipped kitchen, a well equipped gym, community swimming pool, tennis and basketball courts, lake front beach volleyball court, playgrounds and BBQ areas. All this in a excellent location conveniently located to grocery stores, shopping, hospitals and a short trip to the area attractions and the airport. MULTIPLE WRITTEN OFFERS RECEIVED

4936 Wise Bird Drive, Windermere
5944 Caymus Loop, Windermere
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene's Pointe, 24-hour gated/attended golf community. Tucked adjacent to the Butler Chain of Lakes this home offers 4 bedrooms, 3 baths, formal living and dining and an office/den. As you enter this one level home you will find 3-way split functional plan. Boasting the primary ensuite separate from the three additional bedrooms with a spacious bath and TWO WALK-IN CLOSETS, and access to the covered/screened lanai. Spacious kitchen with an abundance of cabinetry, convenient desk area and island. Newer stainless Steel appliances. The kitchen, dinette and great room feature two sets of French doors that give way to the covered screened lanai and back yard. Beyond the screened lanai is an oversized paved patio and custom pergola seating. Privacy is included with the 6 ft vinyl fence. New Roof ('20), AC units(’18/’19), Hot Water Heater (’21/Natural Gas), Exterior Paint(’20) Shallow well for irrigation, termite bond, 5 Camera Ring System (8/21) including Flood lights and doorbell, expanded paver driveway (2025) for additional parking, blinds and plantation shutters, central vacuum system, and new septic pump('22) are just a few of the great features of this home. Located close to dining, shopping, expressways, tourist attractions, and top-rated public and private schools, this home and community has it all!

5944 Caymus Loop, Windermere
8229 Tibet Butler Drive, Windermere
$1,999,000
4 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Gracious Golf-Course Living in Keene’s Pointe . Welcome to an exceptional retreat in the prestigious, 24-hour guard-gated community where refined interiors, resort-style outdoor living and the coveted Windermere lifestyle come together beautifully. Perfectly positioned on 0.35 acres overlooking the 8th fairway of The Golden Bear Club’s Jack Nicklaus Signature golf course, this extensively updated 4-bedroom, 4-bath residence offers 3,912 square feet of living space designed for both elegant entertaining and comfortable everyday living. From the moment you enter, thoughtful upgrades and sophisticated finishes set the tone. Rich wood floors, designer lighting, custom window treatments and beautifully renovated living spaces flow into the heart of the home: a show-stopping gourmet kitchen featuring quartz countertops, an impressive 9-foot island, six-burner gas cooktop, wine refrigerator and stand-alone ice maker. Whether hosting a celebration or enjoying a quiet evening at home, this kitchen was made to gather around. The home's flexible floor plan is one of its greatest luxuries. Three bedrooms and three full baths are conveniently located on the first floor, including an expansive primary suite with a spa-inspired bath, oversized walk-in jetted shower and spectacular 12x14 ft. closet. A generously sized secondary primary bedroom features its own en-suite bath, while a dedicated home office with French doors provides a private and polished work-from-home environment. Upstairs becomes a retreat of its own, with a spacious bonus/gathering room, full bath and large bedroom accommodating two queen beds—an ideal arrangement for extended family, older children, visiting guests or a private second living area. Then step outside to your own Florida resort. The screen-enclosed Gunite pool has been completely resurfaced with new inset tile and is complemented by a new pool heater, pump and motor. A covered outdoor kitchen and bar invite year-round entertaining, the perfect setting for evenings under the stars—all framed by peaceful views across the golf course. And the improvements go far beyond what you can see. Recent investments include a new Carrier HVAC system with Wi-Fi-enabled Ecobee smart thermostats and UV systems, a refurbished whole-house Briggs & Stratton generator, enhanced landscape lighting, whole-house water purification, automated electric blinds in the primary suite, an EV charging outlet and overhead garage storage. Country Club living at its membership opportunities at The Golden Bear Club offer golf, tennis, fitness, swimming, dining, clubhouse amenities and an active social lifestyle. This is more than a beautifully renovated home. It is a thoughtfully designed sanctuary offering the space to gather, the privacy to retreat, and an extraordinary setting in which to enjoy the very best of Windermere living. Turnkey luxury. Golf-course views. Resort-style outdoor living. Welcome home to Keene’s Pointe.

8229 Tibet Butler Drive, Windermere
6120 Greatwater Drive, Windermere
$3,999,000
5 Beds ⋅ 6 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Keene’s Pointe – 24-hour gated/attended community in Windermere, Florida. Experience refined luxury in this exceptional golf-front estate perfectly positioned along the 17th fairway of The Golden Bear Club. Fully renovated, architecturally refined and intentionally designed by Ashley Martin Home. From the moment you enter, an inviting foyer opens to a spacious living room framed by 12-foot ceilings, expansive windows, and views of the course, filling the home with natural light and warmth, as well as a functional dining room with built-in cabinetry, perfect for entertaining. Designed with both elegance and functionality in mind, the home features wide-plank hardwood flooring throughout, custom drapery and shades, and extensive upgraded lighting and finishes. The private office is a standout, complete with rich built-in cabinetry and a wood-accent ceiling that creates a sophisticated workspace. The primary suite is a true retreat, accessed through a private vestibule-style entrance offering a serene escape. Inside, enjoy access to the outdoors, a spa-inspired bath with a freestanding tub, an oversized walk-in shower, and a spacious custom walk-in closet with built-ins. The chef’s kitchen is thoughtfully appointed with built-in refrigeration and dishwasher, an appliance garage, a large center island, Butler’s pantry with wine refrigeration, and a generous breakfast nook. A mud area with built-ins adds everyday convenience, while the family room showcases custom built-ins for effortless living. The home offers a versatile and spacious layout, including two ensuite bedrooms with walk-in closets on the main level, and two additional bedrooms upstairs connected by a shared bath. The second floor also features a loft with built-ins that can easily function as a fifth bedroom, playroom or media room, along with a bonus space overlooking the golf course—currently used as a gym, but ideal for a game room or lounge. Outdoor living is equally impressive, featuring a saltwater pool and spa, fire pit, cabana with summer kitchen, and a private putting green. The fenced yard and retractable screened lanai create a seamless indoor-outdoor experience, while a convenient exterior-access half bath serves the pool area. Additional highlights include a well-appointed laundry room with stacked washer and dryer, and a four-car garage with high ceilings and custom flooring, and much more! This turn-key home can be purchased fully furnished and decorated. Conveniently located to shopping, dining, expressways, tourist attractions, and top-rated public and private schools, this is a rare opportunity to own a meticulously designed, luxury estate that blends comfort, style, location, and stunning golf course views into one extraordinary residence.

6120 Greatwater Drive, Windermere
11446 Jasper Kay Terrace Unit 202, Windermere
$290,000
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to easy Florida living in the desirable Lakeside community of Windermere! This beautifully maintained 2-bedroom, 2-bathroom condo offers a comfortable open-concept layout with plenty of natural light and a warm, inviting feel throughout. The spacious living and dining areas create an ideal setting for both everyday living and entertaining, while the well-appointed kitchen offers modern appliances, generous counter space, and plenty of room. The primary suite features a private en-suite bath and ample closet space, while the second bedroom offers flexibility for guests, a home office, or additional living needs. Step outside to your private balcony and enjoy your morning coffee or unwind at the end of the day while taking in the peaceful community surroundings. Residents of Lakeside enjoy a variety of amenities designed for an active and relaxed lifestyle, including a community pool, fitness center, and walking trails. Conveniently located near shopping, dining, entertainment, and highly sought-after Windermere-area schools, this home offers the perfect combination of comfort, convenience, and community. Whether you're looking for a low-maintenance primary residence, a place to settle into the Windermere lifestyle, or a smart addition to your real estate portfolio, this condo is ready to welcome you home.

11446 Jasper Kay Terrace Unit 202, Windermere
9010 Reflection Pointe Drive, Windermere
$945,000
4 Beds ⋅ 4 Baths ⋅ Windermere Trails SubDv. ⋅ 34786 Zip Code
Located in the desirable Windermere Trails and less than 15 minutes from Magic Kingdom, this immaculate four-bedroom 3.5-bath pool home offers an exceptional combination of style, comfort and Central Florida convenience. Unwind beside your own heated saltwater pool and spa while enjoying views of the Disney fireworks. Inside, tile flooring extends throughout the home, creating a clean and cohesive look that is both attractive and easy to maintain. Fresh interior paint in 2026 enhances the bright, welcoming atmosphere. The formal dining room makes a beautiful first impression with its gorgeous coffered ceiling, providing an elegant setting for holiday dinners, celebrations and evenings with friends. The kitchen is designed for anyone who appreciates generous workspace and exceptional storage. A substantial amount of cabinetry is complemented by expansive granite countertops, a tiled backsplash and an oversized walk-in pantry. Pendant lighting highlights the breakfast bar, creating a natural place for casual meals and conversation. Built-in stainless steel appliances and a Bosch Dacor refrigerator installed in 2022 complete this impressive space. A drinking water filtration system and a whole-house water softener add everyday convenience. The kitchen opens naturally to the spacious family room, where a stacked stone accent wall adds warmth, texture and architectural interest. Views of the pool create a beautiful backdrop and keep the indoor living areas connected to the outdoor setting. Whether hosting a crowd or enjoying a quiet evening at home, the open arrangement allows everyone to remain part of the conversation. Go outside to the heated saltwater pool and spa. With the propane heater, the pool can be enjoyed well beyond the traditional swimming season, while the space offers plenty of room for lounging, dining and entertaining. The pool filtration equipment was replaced in 2024. The thoughtfully planned four-bedroom, 3.5-bath layout provides flexibility for a family, guests or a home office. The washer and dryer (2022) are also included. A complete Bosch HVAC system, including interior and exterior equipment, was installed in spring 2024 and carries a 10-year parts/labor warranty w/required annual maintenance. The water heater is from 2019, and the exterior and tile roof were professionally power washed in 2024. An interior ADT security system and exterior CCTV camera system provide additional peace of mind. A separate two-car (with epoxy floor in 2023 and one-car garage epoxy in 2026) provides three total spaces for vehicles, storage or hobbies. Just inside one of the garages, a drop station features areas for phone charging, along with space for packages, bags and daily essentials. Windermere Trails offers a resort-style community pool, walking trails, playgrounds, pavilions, a dog park and fitness areas. Surrounded by the natural beauty of the Butler Chain of Lakes, the community is close to highly regarded A-rated schools, Lakeside Village, Hamlin Town Center, Winter Garden Village, Horizon West and the renowned dining of Dr. Phillips. Nearby SR 429 provides convenient connections to the Turnpike, SR 408 and I-4, while Walt Disney World, Disney Springs, shopping, golf, boating, restaurants and medical services are all nearby. Beautifully maintained and ready now, this home combines inviting interior spaces, a private pool retreat, recent improvements and a location that places the best of Central Florida at your doorstep.

9010 Reflection Pointe Drive, Windermere
628 Forest Street, Windermere
$700,000
1 Beds ⋅ 1 Baths ⋅ Marsh Sub SubDv. ⋅ 34786 Zip Code
Charming 1 Bedroom 1 Bath Craftsman Cottage on a spacious lot in Downtown Windermere * Whole House Natural Gas Generator keeps the lights and hot water on during all storms * Mature Oak Trees * The covered porches on the front and rear offer additional spaces to entertain, watch nature or read your favorite book while you slow down and truly experience the "Old Windermere" lifestyle * Home has been lovingly maintained and will impress even the most finicky Buyer * Don't miss this rare opportunity * Must see inside to really appreciate the home * A Garage can be added on the front and a Virtual Garage is in the pictures * there is enough room to add another Bedroom Suite in the backyard - Call for details

628 Forest Street, Windermere
9043 Horizon Pointe Trail, Windermere
$870,000
4 Beds ⋅ 3 Baths ⋅ Windermere Trls SubDv. ⋅ 34786 Zip Code
Windermere Custom Interior Pool Home, 4 bedroom, 2 Primary Suites, 3 full Bathrooms New Exterior and Interior paint 2026, New Hardwood Bamboo Floors 2025, Crown Molding, Coffered Ceilings. New Heated Salt Water Pool, New Air Conditioner 2025, New Hot Water Heater 2025, Gourmet Kitchen with Hand Cut European Backsplash, Butler Pantry and Walk In Pantry, New Dishwasher 2024. Remodeled Master Shower 2023. Custom Stair Railing, New Paver Front porch and Driveway. Double Pain Windows and Extra Insulated exterior Walls. Watch Disney Fireworks from your front porch. Community Pool with Cabana, walking trials, tot lot, outdoor physical fitness areas, 3 parks, dog park with washing station. Windermere High School voted top school in USA today. Elementary school in Neighborhood, Windermere Prep 3 miles, Close to Publix, Restaurants, and Theme Parks. Butler Chain Public Boat Ramp at Keene Point Park 5 minutes.

9043 Horizon Pointe Trail, Windermere
6102 S Hampshire Ct, Windermere
$2,240,000
4 Beds ⋅ 6 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Welcome to Keene’s Pointe - 24-hour gated/attended golf community situated around The Golden Bear Club, an 18-hole Jack Nicklaus golf course featuring golf, tennis, fitness, dining and swimming. This custom home positioned on a private lot overlooking the sixth hole offers single-story living with a split floor plan. Designed with function in mind, the primary suite and office are situated on one side for added privacy, while three additional bedroom en-suites and the laundry room are located on the opposite side. A double-door invites you into the formal living and dining room with wet bar. Quality finishes throughout, including 8-foot interior doors, custom woodwork and detailed ceiling designs, custom drapes and power blinds, camera system, and much more. The kitchen is equipped with stainless appliances, granite countertops, cooking island, spacious breakfast bar, a hidden walk-in pantry, and a built-in desk area. The family room features a stone gas fireplace with built-in cabinetry and flows naturally into the bonus room with half bath boasting beautiful wood paneled walls, perfect for use as a media room, playroom, or game room. The primary suite includes a sitting area, a 16x13 custom closet, and a well-appointed bathroom with jetted tub, walk-in shower, and dual vanities with makeup area. The office features built-in cabinetry and classic wood detailing. Outdoor living is designed for entertaining and functionality, with heated pool and spa with rock waterfall and fountains and summer kitchen with grill, sink and an area for a beverage refrigerator. The fenced back yard is private with a putting green, mosquito misting system and fire pit. Enjoy nightly Disney fireworks visible from the living room, primary bedroom, kitchen, and outdoor living space. The low-maintenance exterior combines stucco and stone finishes, complemented by a paver driveway and a three-car side-entry garage. Conveniently located to shopping, dining, expressways, tourist attractions and top-rated public and private schools, this highly desired community has it all!

6102 S Hampshire Ct, Windermere
8630 Powder Ridge Trail, Windermere
$528,000
3 Beds ⋅ 3 Baths ⋅ Windermere Trails Phase 1c SubDv. ⋅ 34786 Zip Code
This beautifully renovated 3-bedroom, 2.5-bath luxury home in a prime Windermere location offers the perfect blend of modern elegance, comfort, and peaceful Florida living. The bright open-concept layout creates a seamless flow between the living, dining, and kitchen areas, ideal for both everyday living and entertaining. Recent renovations include new stairs with sleek glass railings, beautifully updated bathrooms, a smart bidet toilet, and new appliances, giving the home a fresh feel, while the downstairs showcases beautiful high-gloss tile flooring that adds to the bright, upscale atmosphere. Upstairs, an additional flex/living area offers the perfect space for a home office, yoga studio, reading retreat, or lounge. One of the home’s standout features is the expansive upstairs balcony, accessible from two bedrooms and overlooking the lake, where you can enjoy your morning coffee or unwind surrounded by mature trees, birds, and nature in a wonderfully quiet setting. The home also features a two-car garage and is conveniently located near the best schools, shopping, dining, entertainment, major roadways, and everyday amenities. With its lake views, open-concept design, extensive updates, flexible living spaces, peaceful natural surroundings, and sought-after Windermere location, this move-in-ready home offers an exceptional combination of luxury, tranquility, and convenience.

8630 Powder Ridge Trail, Windermere
6055 Louise Cove Drive, Windermere
$6,900,000
5 Beds ⋅ 6 Baths ⋅ Isleworth West SubDv. ⋅ 34786 Zip Code
Stately and elegant lakefront estate showcasing the best of Isleworth West. This grand home spans more than 7,000 square feet with 5 bedrooms- of which, four are on the ground floor – plus office, gym, library, storage room, upstairs media room and downstairs bonus room, perched along Lake Louise, the only lake on the Butler Chain surrounded by Isleworth. Expansive formal and living spaces are highlighted by picturesque lake views. The seamless flow from room to room takes full advantage of a layout built for living. The chef’s kitchen with island, gas cooktop, stainless appliances, hidden walk-in pantry, and built-in hutch offer an abundance of space for entertaining or family gatherings. The primary retreat offers an escape from the ordinary with peaceful lake views, a master bath with jetted tub, garden and water view shower, and a showstopping two-story custom closet that will be the envy of all. The executive office with wood walls and built-in shelving offers a luxurious setting for attending to business from home. Three secondary bedrooms on the main floor are all spacious and feature ensuite bathrooms. Upstairs is a fourth bedroom, gym, library, and open media room with balcony. Outdoor amenities include a screened patio with summer kitchen, oversized resort-style pool with travertine decking, large green space, and private dock with covered boat lift plus dock-mounted jet-ski lifts, and 3-car garage. Home also includes a full-house generator. This coveted location within Isleworth West offers an intimate setting with a limited number of homesites and no pass-through traffic. Community is regarded as Central Florida’s most exclusive address with 24-hour manned gates, a full security force, and available on-site home services for carefree living. Isleworth Golf & Country Club is located within the community offering optional membership opportunities.

6055 Louise Cove Drive, Windermere
12914 Vennetta Way, Windermere
$379,900
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code
SELLER OFFERING $5000 FLEXIBLE CONCESSIONS- CAN BE APPLIED TOWARD CLOSING COSTS, RATE BUYDOWNS, PREPAIDS, OR PROPERTY ENHANCEMENTS. NEW ROOF TO BE INSTALLED WITIHIN UPCOMING MONTHS BY HOA. Privacy is hard to find in townhome living—and this Windermere home delivers it. Backing to peaceful conservation with no rear neighbors, this beautifully maintained 3-bedroom, 2.5-bath townhome in sought-after Berkshire Park offers 1,644 square feet, a private fenced courtyard, and a detached two-car garage—all in the heart of Windermere. Inside, the beautifully appointed kitchen features granite countertops, 42-inch cabinetry, stainless steel appliances, and a newly purchased refrigerator and microwave. A spacious dining area and walk-in pantry provide plenty of room for everyday living and entertaining, while French doors open directly to the private courtyard. Surrounded by picturesque views of mature trees and conservation, this outdoor space offers a peaceful setting for morning coffee, dining al fresco, entertaining, or simply unwinding at the end of the day. The kitchen flows seamlessly into the spacious living room, creating a comfortable and inviting gathering space highlighted by an electric fireplace that is included with the home. Upstairs, the spacious primary suite offers a walk-in closet, dual vanities, and an oversized walk-in shower. Two additional bedrooms and a full bathroom provide flexibility for family, guests, or a dedicated home office. Berkshire Park offers a true neighborhood lifestyle with a community pool, tennis and basketball courts, scenic walking trails, tranquil ponds, and mature landscaping. HOA services include landscaping, structural exterior maintenance, and pest control, adding to the ease of low-maintenance townhome living. Ideally located near Walt Disney World, Winter Garden Village, Hamlin Town Center, shopping, dining, major roadways, and area schools, this move-in-ready home combines privacy, convenience, and the Windermere lifestyle in one exceptional location. Come experience the peaceful setting and see what makes 12914 Vennetta Way feel like home.

12914 Vennetta Way, Windermere
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