Windermere Homes with Community Mailbox Community Features

Windermere Homes with Community Mailbox Community Features

Welcome to Windermere, Florida—a picturesque town nestled in Orange County that embodies the charm of a small community while offering proximity to the vibrant attractions of Central Florida. Known for its stunning lakes, lush landscapes, and friendly neighborhoods, Windermere is a haven for those seeking a tranquil lifestyle without sacrificing convenience.

One of the standout features of this delightful town is its array of beautiful homes, many of which are part of the Community Mailbox community. These homes are designed with a sense of community in mind, promoting neighborly connections and interaction. Picture yourself strolling through tree-lined streets, where neighbors gather at the community mailbox to catch up and share stories. This communal space fosters a warm, welcoming atmosphere that is often hard to find in today’s fast-paced world.

In addition to the charming homes, Windermere boasts an impressive array of amenities. Residents enjoy access to scenic parks, top-rated schools, and a variety of recreational activities, including boating and fishing on the pristine lakes. The town's close-knit community hosts numerous events throughout the year, from farmer’s markets to seasonal festivals, making it easy to forge lasting friendships and create cherished memories.

Whether you’re a first-time homebuyer or looking to settle down in a serene environment, Windermere offers an exceptional quality of life. Discover the magic of this enchanting town and explore the homes within the Community Mailbox community—where every day feels like a warm embrace from your neighbors. Welcome home to Windermere!

Newest Windermere Homes with Community Mailbox Community Features

5 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Impressively elegant NEW CONSTRUCTION Isleworth estate, prominently positioned on the 17th fairway of the championship golf course, with sweeping Lake Louise vistas beyond. This home was completely gutted and rebuilt with everything masterfully crafted to create a shimmering grand statement of luxury living on one of the most premier lots in the community. The spectacular 10-foot tall, 6-foot wide swinging front door sets the stage for a residence of distinction. A grand, light filled entry welcomes with soaring ceilings, polished marble floors, and a dramatic glass railed staircase that create an immediate sense of scale and sophistication. The open layout flows seamlessly through the dramatic great room toward a wall of floor to ceiling windows and accordion folding glass doors, inviting natural light and showcasing picturesque views of the just-completed saltwater pool and hot tub, golf course, and lake beyond. An elegant chandelier anchors the space, while the upper level glass balcony adds architectural interest and a modern, gallery style feel. Two bedroom suites on the first floor include an extraordinary primary retreat with double closets - one with a stackable washer and dryer - sitting room, and spa-like bath with glassed wet room with enclosed shower and tub. The stunning chef’s kitchen blends modern elegance with exceptional functionality, showcasing a stunning waterfall edge island wrapped in premium marble. Sleek, custom white cabinetry pairs with professional stainless steel appliances – which include WOLF 6-burner plus griddle cooktop, dishwasher, ice maker, and double ovens - create a clean, architectural aesthetic, while the rich wood flooring adds warmth and contrast. Designer pendant lighting highlights the generous prep and gathering areas, making the kitchen equally suited for intimate mornings or elevated entertaining. The open layout flows seamlessly into the surrounding living spaces, including a formal dining room with butler’s pantry, family dining room and secondary gathering space, enhancing the home’s sense of scale and sophistication. Every detail—from the integrated hood to the refined hardware—reflects a commitment to luxury craftsmanship and timeless style. Upstairs are three additional bedroom suites including one that could be a second master. Outdoor entertaining is inviting and refined with a sparkling pool and spa, expansive pool deck, and just-built cabana with summer kitchen. Full-house generator. The 600-acre Isleworth community is surrounded by the pristine Butler Chain of Lakes and is an exclusive residential enclave that sets the standard of excellence for Central Florida living, 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 golf and social membership opportunities.

5373 Isleworth Country Club Drive, Windermere

4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the 6th fairway of Isleworth Golf & Country Club, this thoughtfully updated single-story residence offers a rare combination of privacy, golf-course views and effortless everyday living. A welcoming circular drive and mature oaks set the stage, while inside, nearly 3,400 square feet unfolds in a light-filled collection of spaces designed to feel equally comfortable for quiet evenings at home or a house full of guests. Natural light pours through the glass entry into a dramatic foyer with a groin-vaulted ceiling, introducing the architectural character found throughout the home. Arched openings lead into the formal living room, where a striking stone fireplace creates a natural gathering place and walls of glass frame views of the garden and fairway beyond. The formal dining space provides an elegant backdrop for entertaining while remaining connected to the heart of the home. The renovated kitchen is both inviting and exceptionally functional, featuring a professional-style gas range, integrated appliances and a 40-bottle wine refrigerator. Custom cabinetry, marble countertops and a distinctive tile range hood complete the space, while additional cabinetry flows seamlessly into the family room to create a built-in entertainment center. Natural light reflects beautifully across the large-format tile floors, creating a bright, cohesive feel from room to room. The primary suite is privately positioned on the northeast wing, welcoming golden morning light into the space. The retreat features a distinctive dual-bath arrangement—one with a walk-in shower and the other with a freestanding soaking tub—along with a cedar-lined walk-in closet with custom built-ins. Three additional bedrooms provide comfortable accommodations for family and guests, including one with an ensuite bath, while the updated hall bath offers dual sinks and convenient pool access. A separate flex room easily adapts as an office, library, fitness room or additional retreat. Outside, a covered patio with fireplace extends the living space year-round, overlooking the open-air pool and spa with the manicured fairway beyond. A rear motor court, two-car garage and dedicated golf-cart parking complete the property. Recent improvements, including a 2020 slate roof, refreshed exterior paint, renovated kitchen and baths, complement the home’s established character. With its single-story footprint, private setting and half-acre golf-course homesite, the opportunity is as compelling as the lifestyle within the gates.

5050 Isleworth Country Club Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Summerport Edens Hammock SubDv. ⋅ 34786 Zip Code

Virtually Staged. There is something truly special about coming home to Summerport and this move-in-ready townhome captures that feeling perfectly. From the moment you arrive, the inviting front porch offers a peaceful spot to sit back and watch the sunset over Ancilla Pond. Inside, the functional main level features a highly desirable first-floor primary suite. The bright kitchen connects seamlessly to a private, fenced patio area. Upstairs, you will find an additional bedroom, a versatile loft area, and a secondary bedroom featuring a charming alcove that makes a wonderful home office or study nook. Out back, enjoy ultimate privacy with an attached garage accessed by a rear road and extended driveway. Because the property backs up to the tranquil marshland of Walsh Pond there are no rear neighbors and you are also just steps from the community playground! Summerport features resort-style amenities, including scenic walking paths, small lakes, a clubhouse pool, a fitness center, a fishing dock, volleyball, and a sand beach area right next to the tennis and basketball courts. Unbeatable Location & Convenience: * Top-Rated Schools: Just a short drive to Keene’s Crossing Elementary, Bridgewater Middle and Windermere High School. Elite private options like Windermere Preparatory School and Foundation Academy are also nearby. * Moments from Disney World and all major theme parks. * Easy Commute: Quick access to SR-429, SR-408, and the Florida Turnpike makes driving a breeze. * Shopping & Dining: Minutes from local restaurants, grocery stores, and the popular Winter Garden Village. Low-Maintenance Living, the HOA fully maintains the exterior including the lawn, exterior painting and roof replacements (new roof installed in 2022), allowing for a truly easy lifestyle. Schedule your showing today!

14077 Ancilla Boulevard, Windermere

3 Beds ⋅ 3 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code

Under Construction. Enjoy convenient, low-maintenance living in this two-story townhome featuring a private paver courtyard and two-car garage, perfectly located in the heart of Windermere. Designed for both comfort and functionality, this home offers a smart layout ideal for everyday living and entertaining. Interior finishes reflect the AW Collection Serene with upgrades including 42" kitchen cabinets, quartz countertops, tiled backsplash, stainless steel appliances and luxury vinyl plank flooring throughout the main living areas. Ideally situated, you’re just 30 minutes from Orlando International Airport and 15 minutes from world-famous Disney theme parks. The community is also zoned for great schools and is minutes from downtown Winter Garden, where charming streets, local history, shopping, dining, and community events create a vibrant lifestyle. Residents will also enjoy a community pool and playground area. With its prime location and elegant design, this townhome delivers the perfect blend of convenience, comfort, and Central Florida living. *Representation images and renderings are for illustrative purposes. Actual options and design finishes of home may vary.

13325 Lush Lime Alley, Windermere

3 Beds ⋅ 3 Baths ⋅ Lakes Of Windermere Lake Reams Townhomes Phase 3 SubDv. ⋅ 34786 Zip Code

Beautiful end-unit townhome in Windermere featuring the larger floor plan in the Lake Reams Townhomes community. This well-maintained 3-bedroom, 2.5-bath home offers plenty of natural light and a spacious open-concept kitchen, dining, and living area combo. The kitchen features granite countertops, tiled travertine back splash 46" wood cabinetry, and ceramic tile flooring, with kitchen and laundry appliances included. Upstairs, feel the new plush padded carpeting in the bedrooms, hallway and stairs. The spacious primary suite includes dual vanities, quartz counter top, a large walk-in closet, and walk-in shower. The guest bathroom also has a tub and shower, a single sink with a quartz counter top. Outside, enjoy a private Vinyl fenced in courtyard leading to an oversized rear-entry 2-car garage. The HOA provides low-maintenance living and includes exterior and roof maintenance, landscaping, exterior pest control, and access to the community’s Junior Olympic-size pool. Located approximately 5 minutes from Walt Disney World’s Magic Kingdom, with the added fun of being able to hear and see the Magic Kingdom fireworks each evening. Convenient to Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, major roadways, and highly rated local schools. A great opportunity to enjoy a spacious Windermere townhome in an incredibly convenient location.

8641 Brookvale Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Lake Cawood Cove SubDv. ⋅ 34786 Zip Code

Under Construction. This stylish two-story townhome features three spacious suites, including a second-floor primary suite and two additional bedrooms. The open-concept first floor offers a bright living area. Interior finishes feature the AW Collection Sapphire for a bold, modern style. This Cypress floor plan features a gourmet kitchen with 42” cabinets, quartz countertops, tiled backsplash stainless steel appliances, and luxury vinyl plank flooring. Enjoy a private courtyard and detached two-car garage. Located in the heart of Windermere near top-rated schools, Winter Garden Village, and charming downtown, with community amenities including a pool and playground.

13321 Lush Lime Alley, Windermere

2 Beds ⋅ 3 Baths ⋅ Wickham Park 04 05 06 09 10 11 12 01 SubDv. ⋅ 34786 Zip Code

Virtually Staged. SOME PHOTOS HAVE BEEN VIRTUALLY STAGED. MOVE-IN READY and listed below recent appraisal - ideally located in the highly desirable Wickham Park community of Windermere! This desirable END UNIT 2-bedroom, 2.5-bath townhome offers CAREFREE, LOW-MAINTENANCE LIVING with the added benefit of its end-unit location and an outstanding setting directly across the street from expansive OPEN GREEN SPACE and an ORANGE COUNTY COMMUNITY PARK. Designed for easy Florida living, the home features a recently painted interior and a comfortable, functional floor plan with two bedrooms, each offering its own private full bath. Step outside to the PRIVATE COURTYARD connecting the home to a DETACHED TWO-CAR GARAGE—creating an inviting outdoor space with added privacy and versatility. Major improvements have already been completed, making this home truly MOVE-IN READY: HVAC replaced in 2021, NEW ROOF in 2023, exterior painted in 2024, recently painted interior, and all toilets replaced in 2026. Wickham Park residents enjoy desirable COMMUNITY AMENITIES, including a COMMUNITY POOL and CLUBHOUSE, along with a sought-after Windermere location convenient to Walt Disney World, Orlando theme parks and attractions, shopping, dining, entertainment, schools, and major Central Florida roadways. Enjoy the best of the FLORIDA LIFESTYLE with the convenience and ease of low-maintenance townhome living. Whether you're searching for a PRIMARY RESIDENCE, SECOND HOME, or simply a low-maintenance Windermere home close to Disney and Orlando's world-famous attractions, this END-UNIT townhome delivers LOCATION, CONVENIENCE, OUTDOOR SPACE, and CAREFREE LIVING. With the big-ticket updates already completed, all that's left to do is move in and enjoy. Schedule your private showing today!

7430 Bentonshire Avenue, Windermere

3 Beds ⋅ 3 Baths ⋅ Lake Burden South Ph 2 SubDv. ⋅ 34786 Zip Code

Location, lifestyle, and move-in-ready convenience come together in this beautifully maintained 3-bedroom, 2.5-bath townhome in the highly desirable Windermere/Lake Burden community. Perfectly positioned directly across from the community pool, this home offers the ideal combination of comfort, style, and resort-inspired living. A charming covered front porch welcomes you inside, where you'll find a bright, open floor plan featuring tile flooring throughout the main level and a versatile flex room that makes the perfect home office, study, playroom, or additional living space. The spacious living room is filled with natural light and features elegant French doors that open to your private outdoor retreat. The well-appointed kitchen is designed for both everyday living and entertaining, showcasing solid surface countertops, stainless steel appliances, abundant cabinetry, and a large center island with breakfast bar that overlooks the main living area. Step outside to your own private, fenced brick-paver courtyard, an ideal space for morning coffee, evening gatherings, or relaxing outdoors. The detached two-car garage provides ample parking and additional storage. Living in Lake Burden means enjoying an exceptional lifestyle with amenities just moments from your door, including a resort-style community pool, clubhouse with kitchen and lounge, tennis courts, trails, fishing pier, boardwalk, playground, softball field, picnic areas, and beautiful Lake Burden. Whether you enjoy an active lifestyle or peaceful evenings by the water, this community truly has something for everyone. Conveniently located just minutes from Disney, Winter Garden Village, Downtown Windermere, top-rated schools, shopping, dining, and major highways, this home is ideal as a primary residence, second home, or investment property. Offering prime location, flexible living space, a private courtyard, two-car garage, this is a rare opportunity to own a move-in-ready home in one of Central Florida's most sought-after communities. Schedule your private showing today!

11425 Brownstone Street, Windermere

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

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

5 Beds ⋅ 7 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code

Positioned along the back nine of Isleworth’s renowned championship golf course, this exceptional estate spans nearly 7,000 square feet and has been thoughtfully reimagined through an extensive three-year renovation. Showcasing timeless architecture with a fresh, sophisticated aesthetic, the residence blends elegant European influences with light-filled interiors, superior craftsmanship and refined contemporary finishes. Custom French doors open to a breathtaking foyer, where soaring double-height ceilings introduce beautifully redesigned living spaces. Beautiful new flooring, designer lighting and a striking stone fireplace create an elegant backdrop, while expansive windows frame views of the sparkling pool, spa and outdoor living areas. Designed for both everyday living and effortless entertaining, the home's central gathering spaces include a warm and inviting family room with a fully modernized media display featuring handmade wooden slats and a custom fireplace, seamlessly connected to the spectacular new kitchen. Anchored by an oversized island, the kitchen features custom cabinetry, premium Wolf and Sub-Zero appliances and generous seating, creating a welcoming space for family and guests alike. The primary suite serves as a tranquil retreat, offering direct access to its own lanai along with a beautifully renovated spa-inspired bath featuring a walk-in shower, soaking tub and dual vanities. Four spacious en-suite guest bedrooms provide exceptional comfort and privacy, while the home office offers an ideal work-from-home setting. Upstairs, the original 19th Hole-inspired game room showcases a custom bar and opens to a private balcony overlooking the 16th green. Outside, meticulously manicured grounds provide a private resort-style setting. Offering an impressive sense of scale, the expansive covered lanai features soaring volume ceilings and beautiful new oversized stone tile flooring that elevate the space's timeless architecture. A fully equipped summer kitchen overlooks the custom swimming pool and spa, while generous areas for lounging and dining create an inviting extension of the home's beautifully reimagined interiors. Together, they create the perfect environment for year-round outdoor entertaining and relaxation in one of Central Florida's most prestigious golf communities.

9921 Lake Louise Drive, Windermere

3 Beds ⋅ 3 Baths ⋅ Lakes/Windermere-Lk Reams Twnh SubDv. ⋅ 34786 Zip Code

Located in one of Windermere’s most desirable communities, this beautifully updated 3-bedroom, 2.5-bath townhouse offers the perfect blend of style, comfort, and convenience. Just minutes from Disney, Horizon West, premier shopping, dining, and major highways Step inside to discover a bright, open-concept floor plan filled with natural light and designed for both everyday living and effortless entertaining. The modern kitchen features elegant quartz countertops, stainless steel appliances, ample cabinetry, and overlooks the spacious living and dining areas, creating the perfect gathering space for family and friends. One of the home’s standout features is the private fenced courtyard—an inviting outdoor retreat ideal for relaxing, grilling, entertaining, or simply enjoying Florida’s beautiful weather. The detached two-car garage provides added convenience and extra storage. Upstairs, the spacious primary suite offers a walk-in closet and private en-suite bathroom, while two additional bedrooms and a full bath provide flexibility for family, guests, or a home office. Residents enjoy a low HOA along with outstanding community amenities, including a resort-style swimming pool, playground, sidewalks, and scenic surroundings that make this neighborhood one of Windermere’s most sought-after communities. Zoned for highly desirable schools and located in the heart of the thriving Windermere/Horizon West area, this exceptional home combines modern updates, an unbeatable location, and outstanding value. Don’t miss this incredible opportunity to own a beautifully updated home in one of Central Florida’s most desirable locations. Schedule your private showing today!

12744 Langstaff Drive, Windermere

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