Windermere Homes with Community Mailbox Community Features

Windermere Homes with Community Mailbox Community Features

Welcome to Windermere, Florida—a picturesque town nestled in the heart of Orange County, known for its stunning lakes, lush landscapes, and a welcoming community spirit. Just a stone's throw from the vibrant city of Orlando, Windermere offers a perfect blend of serene suburban living and convenient access to urban amenities. With its charming streets lined with oak trees and beautiful waterfront views, this idyllic town is a haven for families, retirees, and anyone seeking a peaceful lifestyle.

One of the standout features of Windermere is its diverse selection of homes, many of which boast community mailbox features. These thoughtfully designed neighborhoods foster a sense of camaraderie among residents, making it easy to connect with neighbors while enjoying the convenience of community amenities. Imagine stepping out of your front door to collect your mail in a friendly environment where you can greet fellow residents and share a smile.

Windermere is not just about beautiful homes; it also offers a wealth of recreational opportunities. Residents can explore numerous parks, enjoy scenic walking trails, or take advantage of the nearby lakes for fishing and boating. The local community is vibrant, with seasonal events, farmers' markets, and festivals that celebrate the town's rich heritage.

Whether you’re looking for a cozy family home or an elegant estate, Windermere's real estate market has something for everyone. Embrace the charm and warmth of this beautiful community, where every day feels like a vacation. Come and discover your dream home in Windermere today!

Newest Windermere Homes with Community Mailbox Community Features

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
8168 Boat Hook Loop Unit 302, Windermere
$299,997
2 Beds ⋅ 2 Baths ⋅ Lakeside/Lks/Windermere SubDv. ⋅ 34786 Zip Code
Welcome to this spacious 2-bedroom, 2-bathroom third-floor condo in an elevator building, meaning no noisy above neighbors, in a convenient Windermere location, situated within walking distance from the community clubhouse and its extensive resort-style amenities. Offering an open floor plan, generous living spaces, and a low-maintenance lifestyle, this home is well suited for a full-time residence, second home, or investment property. The open-concept living and dining areas create a comfortable space for everyday living and entertaining, while the spacious kitchen features a breakfast bar, tons of cabinet storage, and large pantry closet. Both bedrooms are generously sized with ample closet space. The primary suite includes a private en-suite bathroom and walk-in closet. An enclosed outdoor living area provides additional space to relax, enjoy your morning coffee, or unwind at the end of the day. The community clubhouse is located just steps away and offers a variety of amenities, including a large swimming pool, fitness center, library, fireplace gathering area, kitchen facilities for entertaining, volleyball court, and playground. Located in Windermere with convenient access to Walt Disney World, shopping, A rated schools, dining, entertainment, and major Central Florida attractions. Disney's Magic Kingdom is approximately 10 minutes away, making this property an attractive option for those seeking a primary residence, vacation home, or investment opportunity in the Orlando area. Schedule your private showing today and discover the convenience and lifestyle this Windermere condo has to offer.

8168 Boat Hook Loop Unit 302, Windermere
5092 Isleworth Country Club Drive, Windermere
$8,500,000
4 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth championship golf course with breathtaking views of Hole 6, this grand estate occupies an oversized lot along Isleworth’s main drive and has been beautifully reimagined with an extensive transformation over the last two years. The result is a sophisticated, move-in-ready home where timeless architectural character blends seamlessly with thoroughly modern style. Originally built by Pellegrini Homes and expanded to 7,100 square feet, the residence retains its signature architectural details, including custom ceilings, travertine floors with intricate tile inlays, and carefully crafted shell stone columns. The grandeur of the formal living room is accentuated by its soaring 20-foot ceiling, magnificent chandelier, and stately stone fireplace. A former bonus room has been thoughtfully transformed into the home's impressive new chef's kitchen, featuring custom cabinetry, an Italian-made 48-inch ILVE range, a luxury appliance collection, and elegant finishes. The original kitchen has been reimagined as a sophisticated entertaining bar with custom cabinetry, a built-in espresso cabinet, wine storage, and dedicated space for morning coffee and smoothies. Both spaces connect effortlessly to the casual dining area and formal dining room, creating an exceptional flow for everyday living and entertaining. The family room offers an open, airy setting with a built-in media display and effortless connection to the lanai. The main-level owner's suite provides a private retreat with a cozy fireplace, dual closets, and a lavish bath featuring dual vanities, a walk-in shower, and a luxurious soaking tub framed by elegant stone columns. A new main-level bedroom with private en-suite bath and an enlarged loft suite add flexibility for family and guests. Throughout the residence, new flooring, custom cabinetry and built-ins, designer lighting including bespoke Italian Murano glass fixtures, custom drapery, automated shades, and beautifully appointed furnishings create a cohesive, elevated aesthetic. Custom London-made closet lighting adds another layer of thoughtful detail, while modernized infrastructure, integrated technology, whole-home Wi-Fi, security, and smart-home features provide a seamless foundation for today's lifestyle. Outside, the residence has been transformed into an exceptional setting for both relaxation and entertaining. The pool has been resurfaced, outdoor living areas expanded, and a new outdoor kitchen and grilling area added, while a completely redesigned landscape, lighting, fencing, and fountain features enhance the grounds. Upstairs, the bedroom suites and expansive balcony capture panoramic views of the golf course and sparkling waters of Lake Bessie. The European-style lanai, with its graceful balustrade, creates an inviting setting for al fresco gatherings and captivating sunsets. This exceptional estate offers a rare combination of timeless architectural character, comprehensive modern improvements, sophisticated design, and an enviable golf-front setting within Isleworth.

5092 Isleworth Country Club Drive, Windermere
6113 Grosvenor Shore Drive, Windermere
$6,950,000
7 Beds ⋅ 8 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code
Set behind the guarded gates of Keene's Pointe, lies this masterfully crafted 7-bedroom, 8-bath lakefront estate by Stonebridge Custom Homes presenting an extraordinary opportunity for those seeking uncompromising elegance and everyday indulgence. Expertly designed to invite abundant natural light throughout its over 8700 sqft magnificent interiors while still offering complete privacy and astounding wooded and lake views over its 4+ acre grounds. A stately brick-paver drive, twin motor courts with garage parking for 4 cars and a golf cart, set the tone for the refined lifestyle that awaits within. Through 10-foot solid double doors, the foyer opens to a two-story travertine-tiled formal living area with dramatic stone fireplace and towering windows that frame views of the pool and lake. The kitchen is a culinary masterpiece, featuring a hidden walk-in pantry, Thermador commercial grade appliance suite, including full-size refrigerator and separate freezer, Bosch Dishwasher, Scotsman Ice maker, Busby cabinets, granite countertops, and a double island setup designed for effortless entertaining. A beverage bar connects the kitchen to the formal dining room and iron-gated wine room with 45 bottle Brisa wine refrigerator. The open-concept layout offers casual dining off the kitchen and a family room that flows seamlessly into theatre-style lounge. The first-floor primary suite is a study in calm sophistication, featuring sitting area, poolside terrace access, coffee bar, 2 custom walk-in closets, and a spa-inspired ensuite with dual granite topped vanities, soaking tub, and multi-head steam shower. An executive study, bonus storage, mudroom and laundry, 2 powder rooms, and a private ensuite for visiting guests, complete the first floor. Upstairs, a bonus room for exercise or crafting, an open area for study or reading, add’l laundry, and 5 spacious bedrooms complemented by 4 full baths, ensure every guest enjoys comfort and privacy. From hidden storage and bonus rooms to thoughtfully curated finishes, every detail has been considered with intention and care. Impeccably maintained and thoughtfully updated where it matters, delivering peace of mind as well as prestige (See feature sheet for a full list of updates). Five sets of wall-to-wall sliders open the beautifully appointed interiors to the private outdoor retreat where guests will want to linger. A summer kitchen and outdoor bar overlook the pool with rock waterfall and spa, while an outdoor gas fireplace anchors evenings that stretch long past sunset. The covered lanai areas are enhanced by electronically controlled invisible screens and a mosquito misting system. The beautifully landscaped grounds and fenced backyard extend to a private dock with covered boathouse and electronic lift, providing effortless access to the pristine waters of Lake Tibet and the interconnected Butler Chain of Lakes. Residents of Keene’s Pointe enjoy a country club lifestyle, with optional membership to the Golden Bear Club offering championship golf, tennis, pickleball, dining, and a vibrant social calendar. Positioned minutes (3.5 mi.) from historic Windermere with easy access to Orlando's attractions. Furnishings and Regal LS4 Power Boat are negotiable for a truly turnkey move.

6113 Grosvenor Shore Drive, Windermere
9310 Isleworth Gardens Drive, Windermere
$3,595,000
3 Beds ⋅ 5 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set within the Gardens of Isleworth, an intimate enclave of custom homes surrounded by lush gardens, water features, bridges and walking paths, this elegant single-story garden villa offers elevated garden views. The residence pairs timeless Mediterranean architecture with sophisticated finishes and a seamless indoor-outdoor design. Beautiful finishes throughout the interior include travertine flooring, wood-beamed ceilings and solid wood doors, creating a warm and gracious aesthetic. The expansive kitchen is designed for both everyday living and entertaining, with double islands, Quartzite countertops, a marble mosaic backsplash, Wolf appliances, a gas range, wet bar and butler’s pantry. A stone fireplace provides a focal point in the living room, while the spacious family room opens through panoramic sliding doors to a covered lanai, extending the living spaces naturally outdoors.The primary suite offers a private retreat with a morning bar, sitting area, spa-inspired bath and generous walk-in closet. A wood-floored study with custom built-ins provides an elegant setting for work, while additional bedrooms offer comfort and privacy for family and guests. Additional interior highlights include the laundry room, powder bath, and a three-car garage.Beyond the interiors, the home embraces its lush garden setting with tranquil pond views and an expansive outdoor living area. The covered lanai features a summer kitchen and pool bath overlooking a heated saltwater pool and spa, creating a private setting for relaxed afternoons and beautiful entertaining. The Gardens of Isleworth offer convenient living in a beautiful setting within Central Florida’s most iconic golf course community.

9310 Isleworth Gardens 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
11532 Waterstone Loop Drive, Windermere
$2,350,000
4 Beds ⋅ 6 Baths ⋅ Waterstone SubDv. ⋅ 34786 Zip Code
SINGLE STORY LIVING and PRIVATE PEDESTRIAN-GATED ACCESS to WINDERMERE PREPARATORY SCHOOL from within the community distinguish this custom Waterstone home. Built in 2014 and located behind a staffed, guard-gated entrance, the residence offers approximately 4,169 square feet, four bedrooms, four full baths, two half baths, and a three-car garage. Two stately palms welcome you to the beautifully landscaped 0.44-acre homesite, while landscape lighting highlights the grounds after sunset. From the moment you enter, the view opens to the CENTRAL COURTYARD, SALTWATER POOL, and SPA. Direct access from the kitchen, family room, and primary suite makes the courtyard part of daily life. Covered lanais, generous lounging areas, a summer kitchen with a full-size motorized screen, and an outdoor fireplace provide space to gather and dine outdoors. The courtyard has been freshly painted, and the travertine pavers were recently sealed. Inside, soaring ceilings, tray details, crown molding, and expansive windows bring light and courtyard views into the living spaces. The kitchen features Wolf and Sub-Zero appliances, rich wood cabinetry, dual islands, bar seating, and a concealed walk-in pantry. The spacious primary suite includes hardwood flooring, a sitting area, two expansive custom walk-in closets, and a bath with a soaking tub, oversized rainfall shower, and generous vanity space. An adjoining flex room can serve as a home office, gym, or private retreat. Additional features include two newer air-conditioning units serving the multizone HVAC system, a sound system throughout the indoor and outdoor living areas, a whole-house Lorex camera system, a porte-cochère, and an expansive paver driveway. Waterstone is near Windermere High School, with convenient access to Winter Garden Village, Lakeside Village, Walt Disney World, and major Orlando routes. Schedule a private showing to experience this distinctive Windermere courtyard home.

11532 Waterstone Loop Drive, Windermere
11446 Jasper Kay Terrace Unit 202, Windermere
$295,000
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
5186 Vardon Drive, Windermere
$4,395,000
6 Beds ⋅ 6 Baths ⋅ Isleworth SubDv. ⋅ 34786 Zip Code
Set along the front nine of Isleworth’s championship golf course, the 4,739-square-foot residence has been beautifully reimagined, pairing a grand architectural presence with contemporary interiors and expansive views across the course. Beyond the private entry gate to the property, a long, dramatic drive leads to the circular motor court anchored by a distinctive tiered fountain, creating an impressive arrival to this beautifully reimagined Isleworth estate. Inside, soaring ceilings and a dramatic two-story foyer introduce beautifully updated living spaces, where new flooring, refined architectural details and distinctive backlit feature walls create a fresh, elevated aesthetic. Primary living spaces include formal living and dining rooms, a kitchen with casual dining, and a home office. The six-bedroom residence offers two bedrooms on the main level, one on the lower level and three on the upper level. The expansive primary suite is includes a large bath finished with oversized floor-to-ceiling stone tile, a freestanding soaking tub, walk-in shower and dual-sink vanity. Designed for year-round enjoyment, the outdoor living experience begins in the enclosed Florida room and unfolds onto a sprawling pool deck overlooking the golf course. A large pool is complemented by an intimate oasis dining area surrounded by a pool moat, a separate sundeck and a covered outdoor grilling area, creating multiple spaces for entertaining, dining and relaxing. With its exceptional arrival, thoughtfully renovated interiors and expansive indoor-outdoor living, this distinctive estate offers a refined setting within one of Isleworth’s most sought-after golf-course locations.

5186 Vardon Drive, Windermere
13317 Lush Lime Alley, Windermere
$549,990
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. This Cawood floor plan features interior finishes from the AW Collection Coastal, blending clean lines and neutral tones and textures. Design upgrades include 42" cabinets, quartz countertops, tiled backsplash, pendant lighting and stainless steel appliances. 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 practical 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.

13317 Lush Lime Alley, Windermere
12934 Vennetta Way, Windermere
$369,000
3 Beds ⋅ 3 Baths ⋅ Lake Sawyer South Ph 03 SubDv. ⋅ 34786 Zip Code
Virtually Staged. Welcome home to this beautifully refreshed 3-bedroom, 2.5-bath end-unit townhome in one of Windermere’s most sought-after communities. Offering the added privacy of an end-unit location, a peaceful conservation backdrop, and a private courtyard, this home delivers the perfect blend of comfort, convenience, and easy Florida living. Freshly painted throughout with brand-new carpet, the home feels bright, clean, and move-in ready from the moment you walk through the door. The inviting layout is filled with natural light and offers plenty of space to relax, entertain, and enjoy everyday life. All three bedrooms are located upstairs, including a spacious primary suite featuring a walk-in closet, dual-sink vanity, and upgraded frameless-glass walk-in shower. Step outside to your private courtyard—a versatile outdoor space perfect for morning coffee, weekend gatherings, or unwinding at the end of the day. Beyond the courtyard, the rear of the home overlooks a conservation area, creating a peaceful natural setting with no immediate rear neighbors. It’s a rare combination of privacy and convenience. And there’s more to look forward to—a new roof is coming soon, adding another layer of value and peace of mind for the next owner. Ideally located near A-rated schools, parks, shopping, dining, and everyday conveniences, this Windermere townhome puts you close to everything while giving you a private place to call home. Come see why this one is worth making your next move!

12934 Vennetta Way, Windermere
5192 Vardon Drive, Windermere
$19,500,000
6 Beds ⋅ 10 Baths ⋅ Isleworth Amd 03 SubDv. ⋅ 34786 Zip Code
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
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