34786 Zip Code FL Real Estate, Homes with Awning(s) for Sale

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

Virtually Staged. An exceptional new construction offering within The Gardens of Isleworth, this newly completed residence by premier custom homebuilder Goehring & Morgan presents a rare opportunity to enjoy the ease of modern luxury within one of the world's most distinguished golf club communities. Thoughtfully designed and never lived in, the home combines timeless architecture with professionally curated interiors by Design Specifications, creating a refined retreat where every detail has been carefully considered. Spanning more than 5,400 square feet, the five-bedroom residence unfolds through a series of light-filled living spaces distinguished by bespoke millwork, tailored cabinetry, and a sophisticated palette of designer-selected finishes. Clean architectural lines and expansive gathering areas create an atmosphere that feels both grand and inviting, while thoughtfully integrated design elements elevate everyday living. Throughout the home, custom cabinetry conceals a fully integrated Sub-Zero, Wolf, and Cove appliance suite, allowing the chef's kitchen to maintain its beautiful aesthetic while delivering professional-grade performance. Well-appointed entertaining spaces nearby transition effortlessly from intimate family gatherings to larger celebrations.Private bedroom retreats offer comfort and tranquility, while spa-inspired baths showcase carefully selected finishes, fixtures and materials that evoke exceptional craftsmanship. The primary suite serves as a sanctuary unto itself, complete with a private beverage bar and thoughtfully designed spaces that encourage both relaxation and retreat.Beyond the interiors, walls of glass open to an inviting outdoor environment designed for year-round enjoyment. A fully equipped summer kitchen anchors the outdoor living experience, creating a natural extension of the home's entertaining spaces and providing the perfect backdrop for gatherings beneath Florida's sunshine and tropical climate.Surrounded by lush landscaping, sparkling water features, and the natural beauty that defines The Gardens of Isleworth, the residence enjoys a setting that feels both private and refined. Residents of Isleworth enjoy access to a lifestyle renowned for championship golf, world-class amenities, exceptional service, and a level of privacy rarely found. Combining the freshness of brand-new construction with the prestige of an established luxury community, this is more than a home, it is an opportunity to experience Isleworth at its finest.

9316 Gladys Garden Ct, Windermere

$4,600,000

8 Beds ⋅ 6 Baths ⋅ West Lake Butler Estates SubDv. ⋅ 34786 Zip Code

Experience the pinnacle of lakefront luxury breathtaking acres in the heart of Windermere, offering an extraordinary 320 feet of pristine ski lake frontage and an unmatched resort-style lifestyle. This one-of-a-kind waterfront compound features a stunning 6-bedroom, 5-bathroom main residence encompassing 12,323 gross square feet with 7,000 heated square feet, thoughtfully designed to maximize comfort, elegance, and breathtaking water views from nearly every angle. Adding to the property’s exceptional versatility is a private 2-bedroom, 1-bathroom guest house and separate garage apartment, creating incredible multigenerational living potential or the ideal setup for extended guests, private offices, or luxury accommodations. The showstopping covered dock pavilion is truly in a class of its own, featuring an expansive over-water lounge, designer outdoor kitchen, bar seating, dining area, and private boat slip, creating the ultimate lakeside retreat. Every detail of this estate has been curated to deliver a private luxury resort experience unlike anything else on the market. The grounds are equally spectacular with a custom screened pool and heated spa overlooking the lake, a private sandy beach, mature canopy trees, waterfront firepit lounge, multiple entertaining spaces, and beautifully manicured landscaping that creates total serenity and privacy. The property’s incredible resort-style entertaining infrastructure makes it ideal for hosting intimate gatherings or large-scale events with ease. Perfectly positioned just minutes from charming downtown Windermere, and conveniently located near Horizon West and downtown Winter Garden, this extraordinary estate also offers easy access to Orlando’s world-renowned attractions — including approximately 25 minutes to Disney and Central Florida’s premier theme parks, and only 30 minutes to Orlando International Airport (MCO). Whether enjoying peaceful mornings on the water, sunset cruises from your private dock, or entertaining on a grand scale, this extraordinary Windermere estate offers a rare opportunity to own one of Central Florida’s most impressive waterfront compounds. A true WOW property that must be experienced in person to fully appreciate its scale, setting, and lifestyle.

5500 W Lake Butler Road, Windermere

$915,000

4 Beds ⋅ 4 Baths ⋅ Peachtree Park SubDv. ⋅ 34786 Zip Code

Come live in paradise!! Minutes from the Magic Kingdom with amazing fireworks view from front porch and private pool. This exceptional builder model offers an unmatched combination of luxury upgrades, thoughtful design, and a premier location in the coveted Peachtree Park community. Perfectly positioned with conservation views and no rear neighbors, this home delivers privacy, style, and a true Windermere lifestyle. Step inside to discover custom upgrades throughout the house, including beams, shiplap accents, built-ins, and designer finishes that elevate every room. The first-floor features engineered hardwood flooring and a beautifully upgraded powder room, while the second floor offers upgraded carpet, a spacious loft with custom built-in shelving and a cushioned bench overlooking the backyard, and a fully outfitted laundry room with soft-close cabinetry and a farmhouse sink. The gourmet kitchen is a showstopper with a quartz island, open shelving, built-in appliances, a stainless steel vent hood, and a stylish backsplash. A custom cushioned bench at the kitchen table seats 8+ and stays with the home. Retreat to the luxurious primary suite featuring a custom shiplap wall, large pendant lighting, and a mounted TV, along with a spa-inspired bath offering dual vanities and a large walk-in shower. The expansive California Closets–designed primary closet is large enough to function as a second office, and the desk remains with the home. Outdoor living shines with a heated electric pool with water fountains, upgraded landscaping including a turfed backyard, bamboo and hedging for privacy, and extensive black rock accents. The pavered lanai features a motorized awning, a mounted TV, and a cedar tongue-and-groove ceiling, mirrored on the charming front porch. Professional landscape lighting enhances both the front and back yards. Insulated garage door, quiet side-winder opener, and a temperature-controlled storage closet with a keypad lock. Epoxy flooring and ceiling storage racks in the garage. Custom plantation shutters, curtains, blinds, and motorized shades. The HOA also takes care of the lawn, trees, fertilizer and hedge trimming. This home is zoned for A+ Windermere schools and offers the rare opportunity to own a meticulously upgraded, model-quality residence in one of the area’s most desirable neighborhoods.

8796 Peachtree Park Court, Windermere

$4,475,000

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

Within the gates of Isleworth, on beautiful Lake Chase among the Butler Chain of Lakes, sits this exquisite estate offering the best of Florida waterfront living. The six-bedroom, five and a half bath home is located adjacent to the driving range and tennis center, and is in close proximity to the renowned Isleworth Golf & Country Club house. Boasting an updated interior spanning more than 5,800 square feet, the estate offers spacious, light-filled rooms showcasing a phenomenal mix of fine finishes which create a home that is chic, stylish and relaxing. From the formal foyer featuring breathtaking views, to the dining room, open kitchen, breakfast nook and large family room, the sprawling floor plan captures exquisite vistas at every turn. The second-floor primary suite overlooks an outdoor oasis with views of Lake Chase, and the primary bath holds an oversized walk-in shower as well as an additional laundry room. Two home offices has separate workspace options. A private guest suite opening to a kitchenette and loft area conveniently rounds out the additional spaces in the home. Enjoy numerous outdoor dining and lounging areas and summer kitchen, along with the grounds featuring an open-air swimming pool, heated spa and boat dock.

6474 Deacon Circle, Windermere

$630,000

4 Beds ⋅ 3 Baths ⋅ Ashlin Park Ph 2 SubDv. ⋅ 34786 Zip Code

Backwoods Trail, a beautifully designed 4-bedroom, 3-bathroom home that perfectly blends modern style with everyday comfort. The bright open-concept floor plan creates an inviting space ideal for both relaxing and entertaining. At the center of the home is a stunning chef’s kitchen featuring crisp white cabinetry, stainless steel appliances, designer backsplash, and an oversized quartz island with seating, seamlessly flowing into the spacious living area highlighted by a custom designer accent wall and media center. The generous primary suite offers a peaceful retreat, while the additional bedrooms provide flexibility for family, guests, or a home office. Step outside to enjoy a fully fenced backyard and an expansive screened-in lanai with paver flooring, offering the perfect space for entertaining, relaxing, or creating your own private fitness or outdoor lounge area. Conveniently located near shopping, dining, and major roadways, this home offers the perfect combination of style, space, and functionality. Don’t miss the opportunity to make this exceptional home yours.

7264 Backwoods Trail, Windermere

$634,994

4 Beds ⋅ 3 Baths ⋅ Lakes/Windermere SubDv. ⋅ 34786 Zip Code

Welcome to one of the best opportunities in Windermere's highly sought-after Lakes of Windermere community! This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect combination of comfort, convenience, and the Florida lifestyle buyers are searching for. Step inside to discover a thoughtfully designed floor plan featuring spacious living areas, abundant natural light, and stylish updates throughout. The well-appointed kitchen opens seamlessly to the main living spaces, creating an ideal setting for everyday living and entertaining. Upstairs, the generous primary suite provides a private retreat, while three additional bedrooms offer flexibility for family, guests, a home office, or fitness space. Outside, enjoy your own private backyard oasis with plenty of room to relax, dine, and enjoy Florida's year-round sunshine. Whether you're hosting friends, grilling on the patio, or simply unwinding after a long day, this outdoor space is designed for making memories. Located in the heart of Windermere, residents of Lakes of Windermere enjoy resort-style amenities including a community pool, playgrounds, parks, walking trails, sports courts, and scenic green spaces. Just minutes from Disney, Horizon West, Winter Garden Village, Hamlin Town Center, top-rated schools, championship golf, dining, shopping, and major highways, this location offers unmatched convenience while maintaining the charm and character that make Windermere one of Central Florida's most desirable places to live. Whether you're searching for a primary residence, relocating to Central Florida, or looking to enjoy the highly coveted Windermere lifestyle, this move-in-ready home delivers exceptional value in an unbeatable location. Schedule your private showing today and discover why so many buyers are choosing to call Windermere home. *** A/C and Water Heater replaced in 2024. Roof replaced in 2025. Exterior of home repainted in 2022 ***

13013 Overstreet Road, Windermere

$6,000,000

6 Beds ⋅ 6 Baths ⋅ Rosser Reserve Rep SubDv. ⋅ 34786 Zip Code

UNDER CONTRACT ACCEPTING BACKUP OFFERS! Luxury, architectural elegance, and an unparalleled lakefront lifestyle on the Butler Chain of Lakes in Windermere. Set on a sprawling lot of over one acre, this extraordinary waterfront estate offers direct access to the prestigious Butler Chain of Lakes — a rare interconnected system of 12 private lakes, providing one of the most exclusive boating lifestyles in Central Florida. From the moment you arrive, the home captivates with its contemporary architecture, expansive paver driveway, and striking façade. Clean lines, refined finishes, and manicured landscaping create an unforgettable first impression. Inside, soaring ceilings, exposed wood beams, and designer lighting enhance the open-concept layout. Oversized sliding glass doors frame breathtaking panoramic lake views while creating a seamless indoor-outdoor flow filled with natural light. The gourmet kitchen serves as the heart of the home, featuring an oversized quartz island, custom cabinetry, and premium stainless steel appliances — perfectly designed for both intimate gatherings and grand-scale entertaining. With 6 spacious bedrooms, 5 full bathrooms, and 1 powder room, the residence offers comfort and privacy for family and guests. Beyond the main living areas, this home delivers an exceptional lifestyle experience with a private gym, dedicated cinema room, game room, and playroom — thoughtfully designed for wellness, entertainment, and family enjoyment. Step outside into your private lakeside retreat. The resort-style pool with integrated spa is complemented by sleek glass railings that preserve unobstructed water views. The covered outdoor living area is a masterpiece, featuring a wood-paneled ceiling, oversized ceiling fan, stone fireplace, mounted TV, and a fully equipped summer kitchen with professional-grade stainless steel grill and hood — ideal for year-round entertaining. The private covered dock accommodates boats and jet skis and provides direct access to all 12 lakes of the Butler Chain, making this property a true paradise for boating enthusiasts. Additional features include: Whole-house water filtration system High-capacity generator capable of powering the entire residence Located within an exclusive gated community with meticulously maintained infrastructure Offering privacy, security, expansive outdoor space, and one of Windermere’s most coveted lakefront settings, this is more than a residence — it is a lifestyle defined by elegance, recreation, and exclusivity. Schedule your private showing and experience lakefront living at its finest.

1002 Down Reserve Court, Windermere

$900,000

3 Beds ⋅ 2 Baths ⋅ Windermere Town SubDv. ⋅ 34786 Zip Code

FULLY RENOVATED DREAM HOME. This home is located right in the heart of the Town of Windermere. Welcome to 4 Chase Rd, Windermere - a refined expression of luxury living where elevated design, privacy, and lifestyle converge. Set within one of Windermere’s most desirable areas, this exceptional residence delivers a seamless blend of sophistication and comfort. From its striking curb appeal to its thoughtfully curated interior spaces, every detail has been designed to create an atmosphere of understated elegance. Inside, expansive living spaces unfold beneath soaring ceilings and abundant natural light, creating a sense of openness while maintaining warmth and intimacy. The chef’s kitchen anchors the home, featuring premium finishes, generous workspace, and effortless flow into the main living and entertaining areas - ideal for both everyday living and elevated gatherings. The primary suite serves as a private sanctuary, offering a tranquil escape with a spa-inspired bath and spacious walk-in storage. Secondary bedrooms provide flexibility for guests, executive office space, or multigenerational living while maintaining the home’s refined aesthetic. Outdoors, the property transforms into a resort-style retreat designed for entertaining and relaxation. Thoughtfully designed outdoor living spaces create the perfect setting for evening gatherings, weekend hosting, or quiet moments of escape. Positioned in the heart of Windermere, the home offers convenient access to top-rated schools, amenities, dining, shopping, and major thoroughfares while preserving the exclusivity and lifestyle the area is known for.

4 Chase Road, Windermere

$426,000

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

Welcome to this well-maintained 3-bedroom, 2.5-bath home offering 1,583 square feet of comfortable living space in the well established Wickham Park community. The home is in excellent condition and has been thoughtfully cared for, making it truly move-in ready. Enjoy low-maintenance living with an HOA that covers exterior maintenance for normal wear and tear, including roof, exterior painting, and landscaping. Residents also have access to a community pool and clubhouse. Conveniently located approximately 5 miles from the Disney Parks and close to Winter Garden Village, this home offers easy access to shopping, dining, and entertainment while still providing a quiet residential setting.

12944 Garridan Avenue, Windermere

$1,550,000

5 Beds ⋅ 5 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Stunning Remodeled Golf Home in Keene’s Pointe – Windermere’s Premier Golf Community. Discover this unique, fully remodeled home in the highly sought-after Keene’s Pointe neighborhood, nestled in the picturesque lake community of Windermere. Offering privacy, breathtaking golf course views, and upgrades at every turn, this move-in-ready gem is the perfect blend of elegance and modern convenience. Home Features: • Total 4 suites Bedrooms, 5 Baths, a Gym & a Office. • 3 spacious suites on the first floor. • 1 converted in-law suite on the second floor. • Dedicated office space for work-from-home convenience. • 3 Car garage with a huge driveway/ parking. • Open-Concept Living with high-end finishes throughout including plantation shutters. Home also features a whole Home Water Filtration System. • Gourmet Kitchen: • Expansive granite island with seating. • Built-in appliances & wine bar. • Double-door dishwasher & trash compactor. • Touchless faucet & instant filtered boiling water. • Natural gas cooktop & pantry. Recent Replacements: • New Gas Water Heater (November 2024). • New Roof (September 2023). • Fairly New Air Conditioning Units (September/2019). Outdoor Oasis – Perfect for Entertaining! • Lanai with unobstructed picture screen for breathtaking views. • Heated pool with built-in bench & jets. • Full Summer Kitchen: • Ice maker, dishwasher, BBQ grill. • Hibachi Japanese grill & pizza oven. • Built-in Gas Fire Pit – perfect for cozy evenings • 5-Person Infrared Jacuzzi Sauna. • Outdoor Bath & Shower for convenience. Prime Location & Community Perks: • A-rated school zone. • Close to theme parks, fine dining, and shopping. • Keene’s Pointe Amenities: • Guarded gate, parks, trails, and clubhouse. • Optional Membership to The Golden Bear Club: • Championship golf course, tennis courts, gym, pool, restaurant & more. Stop searching—this home has it all! Experience luxury, privacy, and resort-style living in one of Windermere’s most exclusive communities. Schedule your private showing today! ****Feel free to Text Listing Agent asking the video of the property****

6001 Caymus Loop, Windermere

$500,000

3 Beds ⋅ 2 Baths ⋅ Lakes/Windermere-Peachtree SubDv. ⋅ 34786 Zip Code

Your opportunity to own a beautiful home in the sought-after gated community of Lakes of Windermere! This charming home offers a spacious and welcoming open floor plan, with the kitchen and dining areas flowing seamlessly into the living room, all filled with excellent natural light. Additional features include a separate laundry room, a breakfast nook, a two-car garage, a fully fenced yard, and a screened-in solar-heated pool. Recent upgrades add peace of mind, including: New AC (2023), New Roof (2021), New Water Heater (2021), New Pool Pump (2024), and Fresh Exterior Paint (2022). The home is conveniently located just steps from the community playground and minutes from Disney, shopping, dining, top-rated schools, and major roadways. Don’t miss this wonderful opportunity!

8726 Greenbank Boulevard, Windermere

$3,100,000

5 Beds ⋅ 7 Baths ⋅ Sawyer Sound SubDv. ⋅ 34786 Zip Code

Welcome to “The Sounding:” a captivating lakefront estate residence with inviting water views and a serene and peaceful setting offering the best of Florida living. Tucked inside this privately gated and intimate enclave of estate homes across the street from Windermere Prep, Sawyer Sound offers an escape from the ordinary and this showplace residence sets the standard for lakefront living. A welcoming entrance showcases style and elegance with a massive Great Room as the lake and massive saltwater pool beckons beyond. An impressive chef’s kitchen with island and stainless appliances are perfectly fitted for entertaining family and friends. Highlights include rich hardwood floors throughout plus Thermador appliances including 6-burner plus griddle stove and hood, custom-built cabinetry, hidden walk-in pantry, expansive built-in China cabinet, and an especially large dining room with picturesque window. Opposite is a primary retreat with sitting room, spa-like bath with soaking tub, walk-in shower, toilet closet, and separate den. Bathrooms just updated. Upstairs are four bedrooms, each with a private full bath, plus gathering room and separate gaming room. Distinct outdoor spaces are crafted for year-round enjoyment: covered cabana with bar and gas grill plus dining space, mammoth saltwater pool with hot tub, and outdoor family room with fireplace and disappearing screens. Boat house with boat lift puts your water toys within reach and offers easy access to Little Lake Sawyer. Also, enjoy nightly Disney World fireworks viewing from the dock. Boat, trailer, kayaks, and all furniture available for purchase separately. Home is fitted with automatic Generac generator plus 3-car garage (one single and one double). Home may be sold furnished if desired.

5024 Sawyer Cove Way, Windermere

$1,330,000

4 Beds ⋅ 4 Baths ⋅ Windermere Reserve SubDv. ⋅ 34786 Zip Code

NEW PRICE, NEW YEAR! Nestled in the TRUE TOWN of WINDERMERE is this Absolutely stunning, meticulously maintained pool home with TALL CEILINGS and lots of land surrounding on both sides! This HIDDEN GEM has majestic mature oaks on a private .74 ACRE CONSERVATION LOT in QUIET, highly desirable Windermere Reserve with access to the BUTLER CHAIN OF LAKES. This solid BLOCK one-story home features a high end NEW METAL ROOF, NEW WOOD LUXURY LAMINATE floors from SPAIN, completely RESURFACED POOL with NEW TILE, lighting & waterfall. NEW water heaters, NEW lighting inside and out, NEW canvas awnings, NEW double door garage opener system, NEW well tank for the updated irrigation system, NEW landscape and sod, NEW fencing, SHELL STONE ENTRY with Spanish tile inlay. Meticulously designed Mediterranean and Spanish updates throughout including the kitchen, baths, and much more! Spacious layout with high ceilings, open floor plan, TWO PRIMARY SUITES BOTH WITH POOL ACCESS, office (or 5th bed), large family room with FIREPLACE, and breakfast area all opening to a screened pool atrium and covered patio—perfect for entertaining and family gatherings! Oversized 3-car side-entry garage along with fenced pet area. As you enter through a canopy of trees, Windermere Reserve backs onto Lake Down and sits across from Isleworth Golf & Country Club. As a Windermere resident, enjoy 6 lighted tennis courts, parks, playgrounds, frisbee golf, lakefront beaches, and two private boat ramps—Lake Down is just around the corner! Golf-cart friendly town with quaint coffee shops, restaurants, a brewery, farmers market, and seasonal events. Minutes from Dr. Phillips, Bay Hill, Restaurant Row, and theme parks. Don't miss out as homes in this community rarely go to market! Don't wait any longer!! Seller Motivated! $146,000 reduction and PRICED to SELL. Let's gooo!

7135 Horizon Circle, Windermere

$615,000

4 Beds ⋅ 3 Baths ⋅ Lakes Windermere Ph 01 49 108 SubDv. ⋅ 34786 Zip Code

**LOCATION -- LOCATION -- LOCATION** **BRAND NEW ROOF -- APRIL 2025** **FRESHLY PAINTED EXTERIOR -- APRIL 2025** **4 BEDROOMS + 2.5 BATHROOMS -- ALL ON ONE LEVEL** **LARGE FULLY RENOVATED KITCHEN -- 2022** **UPDATED WOOD-LOOK TILE FLOORING** **AVAILABLE FOR QUICK CLOSE & MOVE-IN** **A+ SCHOOLS** **LOW HOA** Welcome to the highly desired Lakes of Windermere neighborhood -- with lovely homes, tree-lined streets and amenities galore, this is the place to call "HOME." Starting with great curb appeal on a premium lot located directly across from the community center (pool, park, playground, tennis, volleyball & MORE), this Ashton Woods home welcomes with a large front porch and is filled with unique character and charm. Purchase with CONFIDENCE & PEACE OF MIND…recent updates & special features include: brand new roof (April 2025), freshly painted exterior (April 2025), beautiful wood-look tile throughout all living areas (2022), full kitchen renovation (2022), new carpet (June 2025), extensive crown molding & custom trim work, plantation shutters, updated light fixtures & ceiling fans, 9’ ceilings…and MORE! The fantastic & FLEXIBLE open floor plan features FOUR bedrooms, TWO full bathrooms AND an additional half bathroom -- great for guests or entertaining -- all one ONE LEVEL. The incredible open kitchen was fully renovated in 2022 and features tons of beautiful cabinetry, quartz countertops, extra countertop prep or serving space, large butlers pantry & newer stainless appliances. All appliances STAY -- including washer & dryer. Enjoy the Florida lifestyle outdoors in the large paver patio -- complete with custom built pergola and privacy fencing. The LOW HOA includes a beautiful community pool & pool house, multiple parks, three playgrounds, sand volleyball court, tennis courts, public dock & pier, basketball courts, volleyball, gazebo & walkability -- all for just $80 per month. The PERFECT location - just minutes from Walt Disney World yet away from it all. Zoned for highly rated & desired WINDERMERE SCHOOLS. Conveniently located near HWY 429 access with direct connection to anywhere in Central Florida & beyond. Easy access to shopping and world-class restaurants in Windermere, historic downtown Winter Garden & Winter Garden Village at Fowler Grove. Minutes from access to the famed Butler Chain of Lakes…and MORE! WELCOME HOME!

12524 Aldershot Lane, Windermere

$3,250,000

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

Nestled at the end of a quiet cul-de-sac on 1.15 acres within the renowned Isleworth Golf & Country Club, this exceptional residence offers refined luxury, thoughtful design, and exceptional grounds designed for outdoor enjoyment all year round. Featuring five bedrooms, six full bathrooms, and a powder room, the home spans more than 6,300 square feet, with lovely architectural style and beautifully appointed interiors. The stunning great room is a true centerpiece, featuring soaring cathedral ceilings, exposed wood beams, and abundant natural light. Formal living and dining rooms provide ideal spaces for entertaining, while the chef’s kitchen boasts granite countertops, white cabinetry, and high-end Bosch and Sub-Zero appliances. The primary suite is a serene retreat, featuring a luxurious en-suite bath and direct access to the pergola and pool for seamless indoor-outdoor living. Upstairs, a versatile bonus room offers flexible space for a yoga studio, home gym, game room or creative retreat, complemented by a stylish loft office perfect for work-from-home needs. Step outside to discover the expansive backyard complete with modern pool is surrounded by low-maintenance artificial turf, expansive lanai spaces for alfresco dining, and multiple seating areas ideal for gatherings or quiet relaxation—all framed by a vast, fenced yard. This extraordinary home offers both comfort and sophistication in a community renowned for its golf, amenities, and lifestyle. A rare opportunity to live luxuriously in a premier setting.

9743 Chestnut Ridge Drive, Windermere

$3,100,000

4 Beds ⋅ 4 Baths ⋅ Metcalf Park Rep SubDv. ⋅ 34786 Zip Code

Under contract with contingencies and Backup Offers will be reviewed. Welcome to luxury on Lake Butler Blvd with stunning Wauseon Bay views. This estate spans nearly an acre of landscaped grounds, ideal for relaxation and entertainment. The property features a secondary oversized, air-conditioned garage that could be converted into a guest suite. The main home is a custom-built residence with high ceilings, new wood flooring and expansive lake-view windows. The first-floor primary suite offers a private sitting area and spa-like bath, with an additional bedroom suite on the second floor and two additional guest rooms with access to the hall bathroom. Ideal for entertaining, the formal dining room flows between formal living room and gourmet kitchen. The renovated kitchen is open to both the family room and a perfectly placed breakfast nook with views of the sparkling pool. Rounding out the features of the interior, this home offers first floor laundry room, mid floor storage room and second floor loft with balcony. Outdoors, enjoy a travertine lanai, pool deck, private beach and spacious dock with a sitting room and boat lift. Located in Downtown Windermere, this is tranquility on the Butler Chain of Lakes.

11018 Lake Butler Boulevard, Windermere

$3,000,000

5 Beds ⋅ 6 Baths ⋅ Sawyer Sound SubDv. ⋅ 34786 Zip Code

Experience refined modern living at 5023 Sawyer Sound Way, a luxurious home in the exclusive gated community of Sawyer Sound in Windermere. This 5-bedroom, 5.5-bathroom residence features expansive living spaces, an open-concept floor plan, and abundant natural light. Clean lines and warm, textured finishes create a soft, welcoming atmosphere rarely found in modern design. Enjoy a chef’s kitchen, seamless indoor-outdoor living, a private pool, and high-end finishes throughout—all just steps from Windermere Preparatory School, one of Central Florida’s top-rated private institutions.

5023 Sawyer Cove Way, Windermere

$598,000

3 Beds ⋅ 2 Baths ⋅ Enclave/Berkshire Park B G H I SubDv. ⋅ 34786 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home with a dedicated office, perfectly nestled in one of the area's most sought-after neighborhoods. With an open-concept layout and thoughtful updates throughout, this home offers the perfect balance of comfort, functionality, and style. Step into a bright and spacious living area featuring high ceilings, custom built-in shelves, and large windows that fill the space with natural light. The seamless flow from the living and dinette areas to the kitchen makes it ideal for both everyday living and entertaining. The kitchen features stainless steel appliances, abundant cabinet space, a pantry, and a breakfast bar—perfect for casual dining and conversation. Enjoy the flexibility of multiple living spaces, including a formal dining room perfect for hosting special occasions or family dinners, and a dedicated office that provides a quiet retreat for working from home, studying, or reading. The primary suite serves as a peaceful haven, showcasing elegant tray ceilings and crown molding, a generous walk-in closet, and a spa-inspired en-suite bath complete with dual vanities, a soaking tub, and a separate shower. Two additional bedrooms provide flexibility for guests, family, or hobbies. This home also features a BRAND NEW ROOF (April 2025), providing added peace of mind and long-term value. Step outside to your screened-in pool and private backyard oasis—perfect for relaxing, hosting gatherings, or enjoying the Florida lifestyle year-round. Situated just minutes from local parks, top-rated schools, shopping, dining, and major highways, this home places everything you need right at your fingertips. Don’t miss this incredible opportunity—schedule your private tour today and discover all the features that make this house your perfect forever home!

13609 Riggs Way, Windermere

$745,000

4 Beds ⋅ 3 Baths ⋅ Windermere Downs SubDv. ⋅ 34786 Zip Code

Welcome to Windermere Downs. Nestled in one of the most sought after neighborhoods in Windermere, this 70’s modern gem sits on a half acre lot. The U shaped layout of the house wraps around a generous screened lanai under a permanent roof with four skylights. The lanai is accessible from the foyer, primary bedroom, guest room, dining room, and family room and it opens up to the swimming pool and luxurious back yard. The foyer separate the living areas of the house from the bedrooms. The right side opens to the kitchen with its casual dining space, a large room that could be used as formal dining and/or living room, and an extra spacious family room paneled with the quite rare Pecky Cypress wood. The opposite side of the home is devoted to bedrooms and remains very quiet and separated from the rest of the house. The property is just a few homes from the private neighborhood beach lot that features a park, sandy beach, covered dock, and boat ramp. The park is regularly used for annual community gatherings and beach days to enjoy the great Florida sunshine. The boat ramp provides access to the renowned Butler Chain of Lakes. The Butler Chain of Lakes is a system of 13 interconnected lakes known for its excellent water quality, wildlife, and recreational opportunities, including boating, fishing, and water sports. The home features a fenced and covered boat parking spot. The canopy of mature oaks offers shade, privacy, and the charm of a true southern residence. Embrace the tranquillity of this established community as soon as you drive in the neighborhood. Tennis courts, playgrounds and beach lot blend perfectly between homes and the staggering landscape. Charm meets convenience in this delightful area which, being close and well connected to the major expressways, offers the ideal blend of style, community, suburban living, and urban accessibility. New roof and gutters January 2025. AHS Home Warranty included. Walking distance to Yellow Dog Eats and close Windermere Farmer’s Market & Food Truck Night.

9676 Wild Oak Drive, Windermere

$2,075,000

3 Beds ⋅ 3 Baths ⋅ Windermere Town Rep SubDv. ⋅ 34786 Zip Code

One or more photo(s) has been virtually staged. Back on market — buyer’s home sale contingency did not clear. Inspection and appraisal were completed satisfactorily, no fault of the seller or property. Welcome to an extraordinary lakefront retreat on the prestigious Butler Chain of Lakes in Windermere. On a rare 1.43-acre double lot with over 200 feet of prime shoreline on Lake Down, this exquisite residence offers a lifestyle defined by luxury, privacy and breathtaking natural beauty. Surrounded by century-old oak trees and lush tropical landscaping, this elevated single-story home combines timeless Florida architecture with sophisticated modern renovations, creating a unique offering in today’s Windermere real estate market. Spanning 2,681 square feet of impeccably designed living space, the home features an open concept floor plan enhanced by floor-to-ceiling windows that frame panoramic water views from nearly every room. The newly remodeled chef’s kitchen is a masterpiece, outfitted with custom cabinetry, stone quartz countertops, high-end stainless appliances and a generous walk-in pantry. Luxury vinyl plank flooring, designer fixtures, and a stunning wood-burning stone fireplace add warmth and character to the spacious living and dining areas. The luxurious primary suite is a private lakeside sanctuary, offering two oversized walk-in closets, floor-to-ceiling windows, and a spa-inspired contemporary bath with dual vanities and a glass-enclosed walk-in shower. Two additional bedrooms, a flexible home office, and expansive living spaces ensure comfort for family and guests. Every inch of this home is designed to celebrate Florida’s indoor-outdoor lifestyle, with sliding glass doors leading to a newly constructed oversized deck ideal for entertaining, dining and sunset watching. A standout feature of this property is the rare, grandfathered two-story boathouse complete with a private dock and boat lift, ideal for launching your watercraft onto the interconnected lakes of the famed Butler Chain. Enjoy world-class boating, fishing and watersports right from your backyard. No HOA restrictions provide the ultimate freedom to personalize your estate. Just minutes from downtown Windermere’s charming boutiques, cafes, farmers market and parks, and a short drive to Orlando’s luxury shopping, fine dining, championship golf courses and internationally renowned theme parks, this exceptional property delivers an unmatched blend of serenity and accessibility. Zoned for top-rated Orange County schools, including Windermere Elementary, Gotha Middle and Olympia High School, and positioned in proximity to Orlando International Airport and major highways. This once-in-a-lifetime offering is ideal for those seeking the ultimate Florida lakefront home, a rare Windermere double lot and access to the elite Butler Chain of Lakes lifestyle. Whether you are seeking a full-time residence or an exclusive vacation retreat, this Windermere luxury estate offers an extraordinary opportunity to live surrounded by natural beauty and unparalleled convenience.

647 Ridgewood Drive, Windermere

$4,350,000

6 Beds ⋅ 8 Baths ⋅ Isleworth 01 Amd SubDv. ⋅ 34786 Zip Code

PRICED TO SELL!!!! Your family simply must see this heavenly retreat! Nestled on a tranquil cul-de-sac, this Isleworth estate will steal your heart. From every corner of the house, you'll be captivated by the breathtaking views of Hourglass Pond. As you step into the living room, your eyes will be drawn to the sparkling water and the lush greenery of the golf course. With six spacious bedroom suites and a half bath, this home is designed for both luxury and comfort. It's a haven for entertaining, with outdoor areas that boast an exceptional summer kitchen, an oversized pool, and even a state-of-the-art synthetic soccer field. Imagine the joy of spending your evenings on the spacious upper deck, surrounded by the serenity of the pond, the beauty of the golf course, and the hues of a glorious sunset. And that's not all! The lower-level is a haven of fun, with a billiard room, a cozy kitchenette, a TV room for movie nights, guest quarters, a full pool bath, and a convenient laundry room. This house is a dream come true.

5410 Monterrey Club Court, Windermere

$4,250,000

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

Within the gates of Isleworth, on beautiful Lake Chase among the Butler Chain of Lakes, sits this exquisite estate offering the best of Florida waterfront living. The six-bedroom, five and a half bath home is located adjacent to the driving range and tennis center, and is in close proximity to the renowned Isleworth Golf & Country Club house. Boasting an updated interior spanning more than 5,800 square feet, the estate offers spacious, light-filled rooms showcasing a phenomenal mix of fine finishes which create a home that is chic, stylish and relaxing. From the formal foyer featuring breathtaking views, to the dining room, open kitchen, breakfast nook and large family room, the sprawling floor plan captures exquisite vistas at every turn. The second-floor primary suite overlooks an outdoor oasis with views of Lake Chase, and the primary bath holds an oversized walk-in shower as well as an additional laundry room. Two home offices offer separate workspace options. A private guest suite opening to a kitchenette and loft area conveniently rounds out the additional spaces in the home. Enjoy numerous outdoor dining and lounging areas and summer kitchen, along with the grounds featuring an open-air swimming pool, heated spa and boat dock.

6474 Deacon Circle, Windermere

$1,522,000

5 Beds ⋅ 4 Baths ⋅ Keenes Pointe SubDv. ⋅ 34786 Zip Code

Classic Florida lifestyle meets charming Southern Architecture in this bright and airy home featuring 3 cozy fireplaces, warm hardwood floors and a tropical grotto pool surrounded by Chicago brick paver decking. The versatile floor plan offers 5BR/4Full Baths PLUS Office PLUS Game room and Bar, with the Office doubling as a potential 6th Bedroom. You will find the Primary Retreat and two Bedrooms/2 Baths on the main floor and 2BR/1 Bath plus large storage closet/mini bonus room on the second floor. The nearly half-acre homesite boasts a brick privacy wall, creating intimacy in the pool area and a spacious side courtyard enclosed by mature landscaping. The screen enclosed pool lanai provides an entire open air living and dining space under waterproof cover -- complete with large cozy fireplace to warm things up on a cool night! With an oversized 3-Car garage, there’s room for a golf cart in this guard gated golf and lakefront community of Keene’s Pointe, home to the Golden Bear Club (GBC) and its 18-hole Jack Nicklaus Signature Golf Course. Membership is optional but desirable as the GBC has so much to offer members. Enjoy the timeless beauty of this classic home, customized by its current original owners with an enormous main floor game room featuring a walk bar adjoining the pool area. Recent upgrades include all new ACs, roof replaced in 2020, new water heater in 2023, a well for irrigation and over $50K in pool upgrades and landscape lighting enhance this charming home! That's just a few of the many upgrades. See feature sheet for more details! Better yet, come see for yourself!

8324 Tibet Butler Dr, Windermere

$830,000

5 Beds ⋅ 3 Baths ⋅ Windermere Downs 1st Add SubDv. ⋅ 34786 Zip Code

Price Improvement!!!! Discover the epitome of lakeside living at 1939 Broadleaf Ct, nestled in the highly desirable Windermere Downs community. This charming 5-bedroom, 2.5-bathroom home boasts deeded access to the coveted Butler chain, complete with a community boat ramp, dock, and private beach for endless waterfront adventures. Nestled on an expansive lot within a tranquil cul-de-sac, this residence offers the perfect blend of serenity and privacy. Cozy up by the wood-burning fireplace on cool evenings, or bask in the Florida sunshine by the inviting built-in pool, and expansive fenced patio area, ideal for private relaxation and entertaining. Inside, the home exudes warmth and elegance with stunning wood flooring, ceramic tile, and vaulted ceilings in the primary bedroom. The kitchen features upgraded solid wood cabinets with glass faces, granite countertops, and a layout designed for both functionality and style. Windermere Downs presents an array of amenities, from a community park to playgrounds and tennis/pickleball courts, all accessible by a leisurely golf cart ride. Embrace the vibrant growth of downtown Windermere, just a short drive away, where local businesses and the beloved Friday farmers market await. With easy access to major highways, theme parks, and shopping destinations, this home embodies convenience and leisure in one desirable package. Some Renovations currently being done! Don't miss this opportunity to experience the best of Windermere living - schedule your showing today! New Roof funds will be credited to buyer at closing

1939 Broadleaf Court, Windermere

$670,000

4 Beds ⋅ 3 Baths ⋅ Summerport Ph 05 SubDv. ⋅ 34786 Zip Code

This elegant Summerport pool home in Windermere offers a serene retreat with meticulous maintenance and thoughtful design, perfect for both relaxation and productivity. The property boasts modern amenities and convenient features, ensuring comfort and convenience for its residents. New Roof 2021, New HVAC 2020. As you step into the home, you're greeted by warm wood-tone floors and a versatile formal dining/living room combo, providing flexibility for various uses such as a home office or play area. The well-appointed kitchen features 42" wood cabinets, stainless steel appliances, solid surface countertops, and a breakfast bar, complemented by a convenient butler pantry for additional storage and a coffee bar. The adjacent generous family room overlooks the pool and features coffered ceilings and board and batten accents, creating a cozy yet stylish ambiance. Ascending to the second floor, you're greeted by a beautiful antique stained glass window, adding charm to the space. The oversized primary suite offers a luxurious retreat with a double-door entry, walk-in closet with built-ins, and an ensuite bathroom with dual vanities, a garden tub, and a shower. Three additional bedrooms and a shared bath with a shower/tub combo complete the upstairs living area, with a unique built-in library nook leading into one of the bedrooms. Outside, the backyard oasis beckons with an inviting pool, perfect for cooling off during hot summer days, and an in-ground hot tub for relaxing on cooler evenings. Mature landscaping, including a productive orange tree, surrounds the backyard, providing privacy and tranquility. A 6 ft privacy fence ensures seclusion and security. The Summerport community offers a wealth of amenities, including parks, a clubhouse, community pool, basketball court, and tennis courts, as well as resident events organized by the community manager for socializing and mingling with neighbors. Additionally, the neighborhood's well-established presence in Horizon West boasts ample green space, parks, and lakes with community docks. Neighborhood has ATT High-Speed fiber being installed at this moment. Conveniently located near top-rated schools—Keenes Crossing Elementary, Bridgewater Middle, and Windermere High School—the home is also close to major transportation routes such as the 429 and 535, making travel around Central Florida effortless. With its proximity to Disney property and various amenities, this Summerport home offers the perfect balance of comfort, convenience, and luxury living.

4349 Blue Major Drive, Windermere

$1,680,000

6 Beds ⋅ 5 Baths ⋅ Keenes Pointe Ut 06 50 95 SubDv. ⋅ 34786 Zip Code

New Price Adjustment! Don't miss this opportunity!! Welcome to a truly exceptional custom home nestled in the sought after Country Club community of Keene's Pointe. This exquisite residence boasts 4,189 square feet of meticulously designed living space, offering an extraordinary lifestyle in a premier location, featuring a total of 6 bedrooms and 5 bathrooms, including a loft with a bedroom and full bathroom, and a large 6th bedroom with its own full bathroom on the second floor providing ample space for family and guests. The home also includes newly installed SOLAR PANELS that will be paid off at closing with an acceptable offer and water filtration system throughout the home. As you enter, be captivated by the glass staircase that graces the foyer, along with the Decorative Paneling, and Crystal Chandelier at the entrance, all of which sets the tone for the contemporary elegance found throughout this home. The Spacious Master Bedroom is a sanctuary, at the touch of a button or simply asking Alexa to lower the Electric Blinds to darken the room sets the mood for relaxation. The completely re-modeled Master bathroom, which is a masterpiece in itself, features elegant marble accents and a soothing atmosphere. Whether you're unwinding in the luxurious soaking tub or getting ready for the day in the spacious vanity area, this bathroom provides a serene and opulent experience along with new custom Walk-in Closet. The Custom Kitchen the "Heart of the Home" is a culinary masterpiece, complete with Calacatta quartz, New Appliances, Gas Stove, Custom Wood Cabinets, making it a Chef's preference and perfect for Family and Friends to gather around and enjoy. The Open Floor Plan flows into the Covered and Fully Screened Lanai where you'll find a Summer Kitchen and Heated Salt-Water Pool, perfect for hosting gatherings and enjoying the Florida lifestyle. The backyard has been thoughtfully landscaped and includes a playground area creating a family-friendly oasis. This home has many new updates including an updated Kitchen, Lighting, Custom Drapes, Landscaping, New Pavers out front and Pool area, Water filtration system, and so much more! Just Minutes to Disney, Universal, Shopping, Hospitals, and top-rated Windermere public and private schools!

8537 Eagles Loop Circle, Windermere

$995,000

5 Beds ⋅ 4 Baths ⋅ Windermere Downs SubDv. ⋅ 34786 Zip Code

If You Have Inlaws or a Large Family and Need a 1 Story Home That is a True Split Plan Offering 2 Separate Living Areas Then You Must See This Home - Highly Sought After Golf Cart Friendly Windermere Downs Neighborhood with Access to the Butler Chain of Lakes From The Private Community Park With Ramp & Beach on Lake Down - Kitchen has Plenty of Storage with a Large Built In Granite Island with Plenty of Seating - 1 of The Entertainment Areas Has A 10’ Wet Bar with Granite Top and Beverage Fridge - Rear of the House Overlooking the Pool Has Floor To Ceiling Glass Windows & Doors the Lets The Natural Light Flood In - One Side of the Home has a Large Master Suite with Fireplace and a 15x13 Walk in Closet and 2 Bedrooms with a Family Room and Dining Area - Opposite Side of the Home Has 2 Bedrooms and its own Living Room and Dining Area - Most of the Rooms Wrap Around The Pool For Fantastic Views - Multizoned A/C - Oversized 36 x 25 Garage with Air Conditioned Half Bath & Workshop Provide Space For Projects or Home Office - Epoxy Granite Coating on Garage Floor - Ginormous Wood Deck By The Pool - Fenced Yard - Large Detached Shed - New Roof 2023 - New Carpet 2023 - Sewer Line 2018 - Decks 2018 - Custom Fence 2019 - Windermere Downs Hosts Family Friendly Neighborhood Events at Holidays - Community Park with Play Structure Across the Street - Tennis/Pickle Ball Courts - Must See Inside To Truly Appreciate What This Home Has To Offer

9712 Pleasance Circle, Windermere

34786 Zip Code Real Estate & Homes with Awning(s)

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