Windermere Homes with Private Yard Exterior Features

Windermere Homes with Private Yard Exterior Features

Welcome to Windermere, Florida – a picturesque gem nestled in Orange County that perfectly balances serene suburban living with vibrant community spirit. Known for its stunning lakes and lush landscapes, Windermere boasts a tranquil atmosphere that attracts families, professionals, and retirees alike. With a rich history dating back to the 1880s and a commitment to preserving its natural beauty, this charming town offers a unique blend of old-world charm and modern conveniences.

One of the standout features of homes in Windermere is the abundance of properties with private yards. Imagine stepping into your own outdoor oasis, where you can enjoy morning coffee surrounded by nature, host summer barbecues, or create the perfect play area for children and pets. These private outdoor spaces not only enhance your lifestyle but also provide a serene retreat from the hustle and bustle of daily life.

Windermere’s real estate market offers a diverse range of homes, from elegant estates to cozy single-family residences, many of which feature beautifully landscaped yards that are perfect for entertaining or simply unwinding after a long day. The community is known for its excellent schools, upscale shopping, and recreational opportunities, including nearby golf courses and water sports on the stunning Butler Chain of Lakes.

Whether you’re looking to invest in a family home or a peaceful retreat, Windermere offers an idyllic setting that truly feels like home. Discover the charm and allure of this enchanting town, and let your dream of owning a home with a private yard become a reality in Windermere, Florida.

Newest Windermere Homes with Private Yard Exterior Features

7413 Lake Albert Drive, Windermere
$1,799,000
6 Beds ⋅ 7 Baths ⋅ O6451030 MLS
Lakefront living at its finest! This spectacular former model home on beautiful Lake Burden offers breathtaking waterfront views and an exceptional Florida lifestyle. Enjoy boating, water skiing, and fishing right from your own backyard, with a private boat dock and a beautiful swimming pool creating the ultimate outdoor retreat. This impressive 6-bedroom, 6-bathroom residence features a desirable double primary suite layout, oversized bedrooms, beautiful hardwood floors, upgrades throughout, and an oversized private office. The spacious second-floor loft provides additional flexible living space, while two second-floor balconies showcase premier lake views and offers the perfect setting to relax and take in the scenery. Entertain in style with a well-appointed outdoor kitchen and inviting pool area, ideal for gatherings and enjoying the Florida sunshine. Conveniently located near popular restaurants, shopping, and world-famous Disney attractions, this remarkable lakefront property combines space, comfort, and an unbeatable lifestyle. Experience the best of waterfront living in this extraordinary home!

7413 Lake Albert Drive, Windermere
9615 Windy Ridge Road, Windermere
$5,300,000
6 Beds ⋅ 8 Baths ⋅ O6449197 MLS
A palm-framed pool and spa, a balcony-connected game room and a dedicated theater give this Mediterranean-inspired estate a distinctive rhythm of outdoor relaxation and evenings at home. Set on 2.5 fully fenced acres with a private gated entrance, the residence welcomes you along a fountain-centered circular drive to 12-foot iron cathedral-style doors. Inside, marble flooring with decorative inlays flows through most first-floor living areas, while soaring ceilings and a two-story mitered glass window frame views toward the pool and covered terrace. A grand two-story marble staircase rises from the formal living room to an iron-railed interior balcony, with an elevator providing additional access between floors. Beneath coffered ceilings, the kitchen’s curved breakfast bar creates a gathering spot connected to the family room, where an entertainment center and sliding glass wall doors lead to a covered poolside terrace with a fireplace. An elaborately decorated vaulted ceiling gives the formal dining room its own character, complemented by a wine cellar with capacity for 500 bottles. Six oversized bedroom suites include two primary suites and a 19' × 25' suite configured as an executive office with a full bathroom. Decorative ceilings continue through the bedroom spaces, while an elaborate bathroom pairs separate vanities with a tub and walk-in shower. A separate study and mirrored 20-foot fitness studio provide spaces for work and exercise, while a 29' × 29' theater with reclining lounge chairs and tiered seating platforms gives movie nights their own dedicated setting. Upstairs, the 41-foot billiards, game and media room combines a refreshment bar with space for game tables and a pool table, opening through sliding glass walls to a covered stone balcony overlooking the grounds. The 45-foot pool’s shallow beach-style landing, raised spa and expansive terrace invite afternoons outdoors, with broad lawns and a sand volleyball area extending the recreation. Four oversized garages and abundant storage add practical space, while the acreage offers potential to expand the residence or build a detached guesthouse, subject to applicable approvals. Approximately 15 minutes from restaurants, hotels, shopping, Universal Studios and Disney attractions, this estate brings distinctive architecture and varied recreation together for an inviting experience at home.

9615 Windy Ridge Road, Windermere
4827 Flint Road, Windermere
$559,000
3 Beds ⋅ 2 Baths ⋅ O6449449 MLS
Thoughtfully updated and beautifully maintained, this single-story home is tucked along a quiet neighborhood street in Windermere's sought-after Summerport community. Offering a spacious, private lot with room for a future pool, a flexible floor plan, and valuable recent improvements, this home delivers the comfort, convenience, and lifestyle today's buyers are looking for. Featuring 3 bedrooms, 2 bathrooms, a dedicated office, and 2,085 square feet of living space, the thoughtfully designed floor plan offers an easy flow for everyday living and entertaining. The kitchen features granite countertops, a distinctive copper farmhouse sink, and a casual dining area, adding warmth, character, and functionality to the heart of the home. Plantation shutters, newer carpet, and fresh paint create a welcoming, move-in-ready feel throughout. The privately situated primary suite offers a peaceful retreat, thoughtfully separated from the secondary bedrooms, while the dedicated office with French doors provides an ideal space for working from home or enjoying a quiet escape. With dining space already incorporated into the kitchen, the separate formal dining room offers wonderful flexibility and is currently enjoyed as a game room—perfect for entertaining, hobbies, or creating a space that suits your lifestyle. Step outside to one of the home's standout features—a generously sized, professionally landscaped lot offering wonderful privacy, partial fencing, and plenty of room to create your dream backyard retreat, including space for a future pool. The covered rear porch is an inviting spot for morning coffee, outdoor entertaining, or simply enjoying the peaceful surroundings. Just as appealing are the important improvements already completed, including a roof replaced in 2020 and a new HVAC system installed in 2025, offering added peace of mind. Summerport is one of Windermere's most desirable established communities, known for its mature landscaping, neighborhood lakes, scenic walking paths, and wonderful amenities, including a community pool, clubhouse, fitness center tennis courts, and playgrounds. The community is also served by highly regarded local schools, with the shopping, dining, and entertainment of Hamlin and Winter Garden Village just a short drive away. Disney Fan? You can be on Disney property in 20 minutes. Convenient access to major roadways like the 429 makes exploring all of Central Florida a breeze. With its private, spacious lot, versatile single-story layout, meaningful updates, and inviting neighborhood setting, 4827 Flint Road offers a wonderful opportunity to enjoy the best of Windermere living.

4827 Flint Road, Windermere
7231 Sangalla Drive, Windermere
$1,348,000
5 Beds ⋅ 5 Baths ⋅ O6447329 MLS
Virtually Staged. Set behind the gates of Casa Del Lago, 7231 Sangalla Drive offers a fresh interpretation of Windermere living, pairing nearly 4,000 square feet of interior space with a private pool and a location remarkably connected to the destinations that define Southwest Orlando. Recently refreshed, the residence features newly painted interiors and new light white oak luxury vinyl flooring throughout the home, excluding the bathrooms. The result is a lighter, more contemporary palette that carries naturally from room to room and gives the home an entirely new point of view. At the center of the main level, the kitchen combines granite countertops, an oversized island, stainless steel appliances, gas cooking and generous cabinetry and pantry storage. It opens to the living and breakfast areas, creating one continuous space for daily living and entertaining. A formal dining room and dedicated office add definition to the floor plan without interrupting its openness. The first-floor primary suite offers a spacious retreat with a walk-in closet, dual vanities and oversized walk-in shower. Additional bedrooms provide flexibility for guests, work or creative space, while the approximately 448-square-foot upstairs bonus room adds another layer of versatility for a media lounge, game room, fitness space or secondary living area. Outside, the architecture gives way to a distinctly Florida setting. A screened swimming pool, covered lanai and expansive paver deck extend the living space outdoors, complemented by low-maintenance turf and additional backyard space. A three-car garage completes the residence. Casa Del Lago is positioned within Windermere’s Lake Burden area, placing the home near Lakeside Village, Hamlin, Downtown Windermere, Golden Oak, Four Seasons Resort Orlando, Walt Disney World Resort and the Sand Lake Road dining district known as Restaurant Row. The location offers convenient access to shopping, dining, entertainment and major roadways while maintaining the privacy of a gated residential setting. A refreshed interior, private outdoor living and a Windermere address positioned at the center of it all.

7231 Sangalla Drive, Windermere
11532 Waterstone Loop Drive, Windermere
$2,199,000
4 Beds ⋅ 6 Baths ⋅ O6444548 MLS
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
6126 Payne Stewart Drive, Windermere
$3,250,000
3 Beds ⋅ 4 Baths ⋅ O6444116 MLS
Welcome to 6126 Payne Stewart Drive, a beautifully renovated golf villa in Isleworth, just steps from the club house. This 2,848-square-foot home offers three bedrooms, each with its own full bathroom, plus a powder room for guests. Soaring ceilings and an open floor plan bring a sense of space to the main living areas, where travertine floors and new doors complement the recent renovations. The gourmet kitchen features a 10-ft center island and top of the line appliances. The primary suite includes a recently renovated bathroom with a generously sized shower and soaking tub. Outside, a fully fenced garden setting surrounds the pool and spa. A summer kitchen and fireplace make the space inviting for outdoor dining and relaxing in the Florida Sunshine.

6126 Payne Stewart Drive, Windermere
13101 Bellaria Circle, Windermere
$2,995,000
6 Beds ⋅ 9 Baths ⋅ O6434168 MLS
Set on nearly an acre within the prestigious guard-gated community of Bellaria, this remarkable estate combines grand-scale living, exceptional flexibility, and an unbeatable location. Impressive curb appeal creates an immediate sense of arrival, enhanced by a spacious U-shaped driveway and an oversized three-car garage. Beyond the entry, a dramatic formal living room welcomes you with soaring two-story ceilings, abundant natural light, and an elegant bar area complete with a wine refrigerator. The expansive kitchen serves as the heart of the home, featuring a massive center island, extensive cabinetry, generous prep space, and a full suite of stainless steel appliances. A formal dining room provides a refined backdrop for special occasions, while the adjoining breakfast nook offers a relaxed setting for everyday meals. The sprawling first-floor primary suite is a private retreat with impressive proportions and separate his-and-hers walk-in closets. Its spacious bathroom features dual vanities, an oversized walk-in shower, and a soaking tub designed for relaxation. An additional guest suite on the main level provides comfort and privacy for visitors, while a dedicated formal office creates an ideal space for working from home. Upstairs, five additional bedrooms provide tremendous flexibility for family and guests. A spacious loft offers another casual gathering area, while the separate bonus room could easily be transformed into a private home theater, game room, fitness studio, or additional entertainment space. With six bedrooms, multiple living areas, and thoughtfully designed spaces throughout, the home is exceptionally well suited for both everyday living and large-scale entertaining. Outside, an expansive covered patio extends the living space and features a full summer kitchen, making it ideal for dining, entertaining, and enjoying Florida’s year-round sunshine. The enormous backyard offers remarkable possibilities, with ample room to create a custom resort-style pool. Bellaria’s prime location places you just minutes from Winter Garden Village, charming Downtown Windermere, Restaurant Row, world-renowned theme parks, and an outstanding selection of shopping, dining, and entertainment. Offering extraordinary space, privacy, and potential in one of Windermere’s most sought-after gated communities, this impressive estate presents a rare opportunity to create the ultimate luxury lifestyle.

13101 Bellaria Circle, Windermere
5192 Vardon Drive, Windermere
$19,500,000
6 Beds ⋅ 10 Baths ⋅ O6441344 MLS
Timeless elegance and extraordinary privacy define this magnificent lakefront estate within the renowned Isleworth Golf & Country Club. Gracefully positioned on Lake Blanche along the coveted Butler Chain of Lakes. This exceptional residence is designed for the most discerning buyer seeking luxury, exclusivity, and resort-style living on approximately 2.5 acres. Encompassing over 13,494 square feet of refined living space and more than 20,476 total square feet, the estate features six luxurious bedroom suites, eight full baths, and two half baths. Every bedroom offers oversized walk-in closets, while the primary suite is a private sanctuary complete with a sitting room, hidden passage access to the study, private morning kitchen, and direct stairway access to the lower-level fitness retreat. Designed for both grand entertaining and intimate living, the home showcases vanishing glass sliders that seamlessly connect the living room, family room, and bar area to expansive outdoor living spaces and screened terraces overlooking breathtaking sunset views across Lake Blanche. The resort-inspired outdoor setting features a heated saltwater infinity-edge pool and spa, summer kitchen, outdoor shower, and tranquil waterfront ambiance. Exceptional amenities include a full theater room with private bath, elevator servicing all three levels, extensive storage throughout, lower-level gym with steam shower and sauna-ready space, dual laundry features including a dog shower and dog door, and a separate guest house complete with living room, kitchenette, and full bath. Equipped with all-new smart-home technology and integrated systems. The gourmet kitchen is thoughtfully appointed with dual ovens, six-burner gas range, steamer, warming drawer, freestanding refrigerator and freezer, two refrigerator drawers, dual full-size dishwashers, and two microwave ovens. Completing this remarkable offering is a five-car garage, private boat dock with electric lift and jet ski slip, and an unmatched combination of sophistication, comfort, and privacy in one Of Central Florida's most prestigious golf and country club communities along the Butler Chain of Lakes.

5192 Vardon Drive, Windermere
4243 Isabella Circle, Windermere
$3,290,000
5 Beds ⋅ 7 Baths ⋅ O6439995 MLS
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
12909 Cragside Lane, Windermere
$625,000
4 Beds ⋅ 3 Baths ⋅ S5157040 MLS
WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-square-foot single-story home in Lakes of Windermere. Located directly across from a neighborhood pond and fountain, the home offers a uniquely Central Florida setting with nightly views of the Magic Kingdom fireworks just steps from your front door. The exceptional location also provides convenient access to highly regarded public and private schools, childcare, Horizon West amenities and Walt Disney World. This move-in-ready home has been extensively updated, with many of the major expenses of homeownership already completed. Improvements include a new roof, HVAC system, water heater, Resideo smart WiFi thermostat, interior and exterior paint, hard-surface flooring throughout with no carpet, light fixtures and ceiling fans — all in 2021; new refrigerator, range/oven, dishwasher, washer and dryer, backyard fencing, paver outdoor-living area and gazebo in 2023; new kitchen countertops and guest-bath flooring, countertop, sinks and faucets in 2025; and refreshed front and rear landscaping and AT&T Fiber wiring in 2026. The fencing, paver improvements, gazebo and landscaping were reviewed and approved through the community HOA architectural-review process. Inside, the bright and spacious floor plan features an open kitchen and family room along with additional flexible living spaces ideal for a home office, recreation, entertaining or additional gathering space. Crown molding, architectural details and updated finishes complement the extensive mechanical and cosmetic improvements throughout. The fenced backyard provides an inviting extension of the living space with its paver patio, gazebo and refreshed landscaping, while the covered front porch faces toward the peaceful pond and fountain setting. Lakes of Windermere offers a community pool, parks, playgrounds, tennis and basketball courts, sidewalks and recreational spaces. The location is especially convenient to Sunset Park Elementary, Horizon West Middle School and Windermere High School, with Windermere Preparatory School also nearby, along with multiple daycare and early-learning options approximately a mile from the home. Shopping, dining and recreation throughout Horizon West are close at hand, while Walt Disney World and Magic Kingdom are just minutes away. With its water-view setting, nightly Disney fireworks, extensive renovations, newer roof and major systems, hard-surface flooring throughout, upgraded outdoor living spaces, excellent school access, fiber connectivity and highly convenient Windermere location, 12909 Cragside Lane offers an exceptional combination of lifestyle, location and move-in-ready condition.

12909 Cragside Lane, Windermere
5526 Marleon Drive, Windermere
$2,500,000
5 Beds ⋅ 5 Baths ⋅ S5156252 MLS
A rare opportunity to own one of just 18 custom estate homes in this exclusive Windermere enclave of Lake Davis Reserve. Set on more than half an acre, this impressive five-bedroom residence spans over 4,600 square feet, offering a remarkable sense of privacy and seclusion while remaining right in the heart of Windermere. From the moment you enter through the custom iron doors, the craftsmanship and attention to detail are unmistakable. Expansive living spaces, beautiful wood-look porcelain flooring, custom millwork and thoughtfully designed lighting create a home that feels luxurious yet exceptionally comfortable. Custom-designed fireplaces throughout the home provide striking focal points and give each living space its own sense of character and warmth. The chef's kitchen features abundant cabinetry, generous counter space, a large prep island, granite countertops, water softener and a vented cooktop, all opening seamlessly to the main living areas. The spacious primary suite is conveniently located on the first floor and offers a true private retreat, complete with its own custom fireplace, oversized walk-in shower and soaking tub. Additional generously sized bedrooms ensure everyone enjoys ample space, while upstairs, a large flex room with custom built-in cabinetry provides an ideal setting for entertaining, relaxing or movie nights. A dedicated gym adds even more versatility to the floor plan. Outside, the home's sense of privacy becomes even more apparent. A covered lanai, with wiring for remote-controlled screens, opens to a secluded backyard retreat framed by mature tropical landscaping. Completed in 2022, the heated saltwater pool features a PebbleTec finish, multicolor LED lighting, dual sun shelves and an illuminated pergola waterfall. An extended pool deck, outdoor audio, summer kitchen with natural gas, exterior bathroom and app-controlled pool and landscape lighting create an exceptional environment for entertaining or simply enjoying the Florida lifestyle in complete comfort. As evening approaches, the west-facing backyard provides beautiful sunset views in front of your patio gas fireplace. That feeling of seclusion is what makes Lake Davis Reserve so special. Despite its peaceful, private setting, the home sits in the heart of Windermere, with Windermere Preparatory School, Windermere High School and zoning for Windermere Elementary all close by. Disney, SR-429 and premier shopping and dining are just minutes away. Opportunities to purchase in Lake Davis Reserve are exceedingly rare, with only 18 custom estate homes behind its gates. Beautiful in photographs and even better in person, this is a home that simply needs to be experienced. The privacy, scale, custom finishes and atmosphere are difficult to fully capture in photographs. If your buyers are looking for luxury, security and seclusion without sacrificing the convenience of Windermere living, 5526 Marleon Drive deserves to be at the top of their viewing list.

5526 Marleon Drive, Windermere
9043 Horizon Pointe Trail, Windermere
$870,000
4 Beds ⋅ 3 Baths ⋅ O6436017 MLS
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
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