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Homes for Sale with a Pool in Windermere, FL

Welcome to your dedicated resource for homes for sale with a pool in Windermere, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Windermere, FL agent, The Nest Group specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Windermere, FL

$699,999
5 Beds 3 Baths Eden Isle SubDv. 34786 Zip Code
PRICED UNDER APPRAISED VALUE! Nestled behind the gated enclave of Eden Isle in Summerport, this stunning five-bedroom, three-bath residence blends modern updates with generous living space. Newly renovated in 2024, the home showcases luxury vinyl plank flooring throughout, a reimagined kitchen, and fully upgraded downstairs bathrooms. Step inside to soaring ceilings and an abundance of natural light that create an inviting first impression. The entryway opens to a spacious dining room, anchored by an eye-catching chandelier, ideal for hosting gatherings. The dining area transitions effortlessly into the open-concept kitchen, now beautifully updated with granite countertops, a waterfall island, abundant cabinetry, stainless steel appliances, and ample prep space. The expansive living room offers views of the backyard retreat, with direct access to a screened-in patio, private pool, and fully fenced yard, perfect for entertaining or unwinding. Designed with a split-bedroom layout, the home features two primary suites on separate levels. The main-floor primary suite, tucked just off the living area, includes a large walk-in closet and a spa-like bathroom with a rain shower, dual shower heads, floor-to-ceiling tile, double vanities and quartz counters. Two additional bedrooms and a fully renovated guest bath complete with quartz countertops, a new vanity, and a tiled floor-to-ceiling walk-in shower are also located on the first floor. The laundry room sits conveniently off the kitchen with direct garage access. Upstairs, a second primary suite offers a walk-in closet and private bath with dual sinks and a standalone shower, along with another generously sized bedroom just down the hall. Residents of Eden Isle enjoy exclusive amenities including a private boat ramp with access to Lake Speer, a playground, and added privacy. Notable upgrades include: UPGRADES: UPSTAIRS HVAC 2024! WATER HEATER 2023! TESLA CHARGER & BACK UP GATEWAY TO POWERHOUSE 2024! NEW POOL PUMP 2025! NEW POOL SCREENS WITH EXTRA PRIVACY 2024! PREMIUM LVP FLOORING & BASEBOARDS 2024! KITCHEN & DOWNSTAIRS BATHS FULLY RENOVATED 2024! POOL IS HEATED BY SOLAR! ROOF 2021! Conveniently located with easy access to major highways, Orlando’s world-renowned theme parks and attractions, downtown Orlando, Windermere, and Winter Garden, as well as Orlando International Airport, plus an abundance of nearby restaurants and shopping options. Don’t miss this opportunity to own a home in one of Central Florida’s most desirable areas, where lifestyle and convenience come together.

13842 Orange Crest Drive, Windermere

$655,000
4 Beds 2 Baths Providence Ph 01 50 03 SubDv. 34786 Zip Code
WELCOME to this STUNNING, BEAUTIFULLY UPDATED, MOVE-IN READY home in one of Windermere’s most desirable locations! From the moment you arrive, this exceptional property captures your attention with its BRICK-PAVED DRIVEWAY, CHARMING FRONT PORCH, BEAUTIFULLY ENHANCED FRONT AND BACK LANDSCAPING, and RAIN GUTTERS, offering outstanding curb appeal and a warm first impression. Boasting over 2,521 square feet of living space, this spacious home features 4 BEDROOMS, 2 BATHROOMS, a 2-CAR GARAGE, and a thoughtfully designed open layout that is perfect for both comfortable everyday living and effortless entertaining. Inside, you will find TILE FLOORING THROUGHOUT, SOARING 8-FOOT DOORS, ARCHED WALKWAYS, CROWN MOLDING, UPGRADED LIGHT FIXTURES, and RECESSED LIGHTING THROUGHOUT THE HOUSE, creating a bright, elegant, and inviting atmosphere. This home has been tastefully refreshed with FRESH INTERIOR PAINT THROUGHOUT, and the KITCHEN CABINETS HAVE BEEN RE-SURFACED AND PAINTED, giving the entire home a clean, stylish, and modern feel. The kitchen opens seamlessly to the family room and breakfast nook, making it the perfect central space for gathering, relaxing, and entertaining. Additional highlights include STAINLESS STEEL APPLIANCES, CEILING FANS, BUILT-IN SURROUND SOUND, EXTERIOR SPOTLIGHTS, CAMERA SECURITY SYSTEM, and an EV CHARGING PORT INSTALLED, adding both comfort and modern convenience. Major value-added improvements include a RE-ROOF COMPLETED IN SEPTEMBER 2020, SPRAY FOAM ATTIC INSULATION for enhanced energy efficiency, and a HIGH-QUALITY HVAC SYSTEM INSTALLED IN OCTOBER 2017, offering lasting comfort and peace of mind. The oversized PRIMARY SUITE serves as a private retreat, complete with a cozy sitting area, CEILING MOLDING, and sliding glass door access to the SCREENED LANAI. The spacious primary bathroom features a GARDEN TUB, WALK-IN SHOWER WITH FRAMELESS GLASS DOOR, DUAL VANITIES, and a LARGE WALK-IN CLOSET. Step outside and enjoy the SCREENED LANAI and spacious backyard, ideal for relaxing, entertaining, or simply enjoying the Florida lifestyle. The community also offers a RESORT-STYLE POOL and TOT LOT for residents to enjoy. Perfectly located just minutes from top-rated schools, Windermere Preparatory, Windermere High School, Publix, Aldi, shopping, dining, Winter Garden Village, the 429 Expressway, Butler Chain of Lakes, and world-famous theme parks, this home offers the perfect blend of LOCATION, STYLE, and VALUE. A rare opportunity to own a BEAUTIFULLY UPDATED home in Windermere that truly stands out. Schedule your private showing today! 3D TOUR AND FLOOR PLAN LINK ABOVE.

13226 Zori Lane, Windermere

$1,399,000
4 Beds 4 Baths Balmoral SubDv. 34786 Zip Code
Virtually Staged. Welcome to an exceptional opportunity in the exclusive gated enclave of Balmoral, home to just 32 distinctive custom residences, where privacy, timeless elegance, and the coveted Windermere lifestyle come together seamlessly. Situated on over half an acre, this beautifully landscaped property offers a serene and private retreat surrounded by mature greenery, lush tropical foliage, and a fully fenced yard thoughtfully designed for both peaceful relaxation and effortless entertaining. Step through striking 8-foot wrought iron and glass entry doors into a bright, light-filled interior featuring soaring 12-foot ceilings, impressive architectural details, and thoughtfully designed living spaces. This spacious 4-bedroom, 4-bath home with a dedicated office and large bonus room and 3-car garage offers an exceptionally flexible layout ideal for both comfortable everyday living and graciously hosting guests. Formal living and dining areas flow effortlessly into the kitchen and family room, creating a natural gathering space filled with warmth, character, and abundant natural light. The oversized first-floor primary suite serves as a tranquil private retreat, complete with direct access to the sparkling pool and covered lanai, along with dual custom closets that provide ample and beautifully organized storage. Upstairs, you’ll find generously sized secondary bedrooms, additional bathrooms, and a versatile bonus room perfect for a media room, home gym, game space, creative studio, or comfortable secondary living area. The outdoor setting is equally impressive, offering the privacy and space to enjoy Florida living throughout the year. Whether gathering around the pool, dining beneath the covered lanai, entertaining family and friends, or simply unwinding among the lush surroundings, the expansive backyard provides a peaceful extension of the home’s interior living spaces. Beyond the home, Windermere offers a distinctive lifestyle that is hard to match. Known for its majestic oak-canopied streets, sparkling lakes, natural beauty, and relaxed small-town atmosphere, the area offers a welcome retreat while remaining conveniently connected to everything Central Florida has to offer. Enjoy charming tree-lined streets, inviting local dining, boutique shopping, scenic parks, and beloved community traditions such as the weekly farmers market and festive seasonal events. Just minutes away, the renowned Butler Chain of Lakes invites you to experience boating, fishing, paddleboarding, watersports, and picturesque days spent on the water. Nearby public lake access makes it easy to take advantage of one of the area’s most celebrated natural features. Windermere’s convenient location also places you within easy reach of Restaurant Row, premier shopping, championship golf courses, world-famous attractions, upscale resorts, and the energy and entertainment of downtown Orlando. Experience refined living in one of Central Florida’s most sought-after communities, where custom architecture, generous homesites, lush surroundings, and an exceptional location create an elevated way of life. This is more than a home, it’s a lifestyle.

9119 Balmoral Mews Sq, Windermere

$2,349,000
4 Beds 3 Baths Lake Down Shores SubDv. 34786 Zip Code
Lakefront living on the Butler Chain of Lakes in the heart of Windermere. This rare offering on Lake Down presents 100 feet of direct frontage, expansive water views and a private setting on a quiet cul-de-sac with no HOA. Set across 1.35 acres, this two-story pool home captures the essence of Windermere’s enduring lakefront lifestyle, where space, privacy, and natural beauty come together in a setting that feels refined and relaxed. From sunrise to sunset, the backdrop is nothing short of extraordinary. Sweeping views stretch across Lake Down, where calm morning waters give way to vibrant evening skies, and a nightly Disney fireworks view adds a subtle sense of wonder to the horizon. The property is thoughtfully oriented to take full advantage of its surroundings, featuring a private beach area, a two-story dock and direct access to the Butler Chain, one of Central Florida’s sought-after and interconnected lake systems, known for its recreational appeal and timeless value. Inside, the home offers a layout designed for everyday living and effortless entertaining. Spacious living and family rooms are complemented by an open kitchen appointed with granite countertops and stainless steel appliances, creating a central gathering space that flows naturally to the outdoors. A dedicated office or den provides flexibility for work or quiet retreat, while an upstairs loft captures elevated, panoramic views of Lake Down, an ideal setting for a secondary lounge, media space or creative studio. The outdoor experience is equally compelling. A resort-style pool anchors the backyard, accompanied by a screened porch and expansive lawn that extends toward the water’s edge. The setting invites relaxed afternoons and large-scale gatherings, with ample room to further enhance or personalize the landscape. A greenhouse and additional storage add charm and functionality, supporting a variety of lifestyle needs. A second-story balcony offers yet another vantage point, where elevated lake views and evening fireworks create a memorable daily backdrop. Whether enjoying a quiet morning coffee or winding down at sunset, this space reinforces the home’s seamless connection to its environment. Positioned in a peaceful and private location, yet just moments from renowned restaurants, shopping and everyday conveniences, the property offers a rare balance of seclusion and accessibility. Its location on one of the desirable stretches of Lake Down further underscores its long-term appeal. This is a compelling opportunity to enjoy the home as it exists today or to reimagine the site as an exceptional custom waterfront estate. In a setting defined by natural beauty, established luxury and enduring demand, properties of this caliber and positioning are increasingly rare.

9620 Maywood Drive, Windermere

$370,000
3 Beds 3 Baths Lake Sawyer South Ph 3 SubDv. 34786 Zip Code
PRICE CORRECTION! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 2.5-bath townhouse located in the highly sought-after Lake Sawyer South in Windermere in close proximity to Disney World. Surrounded by picturesque, tree-lined streets, this well-maintained home welcomes you with a bright and open kitchen area featuring granite countertops, stainless steel appliances, and a walk-in pantry. The open living area with elegant French doors lead to a private, paved courtyard that seamlessly connects to the detached 2-car garage—perfect for indoor-outdoor living. The first floor is complete with a spacious laundry room and a half bath. Upstairs, the expansive primary suite offers a peaceful retreat with a dual vanity en suite bath, while two additional bedrooms share a full bathroom—ideal for family, guests, or a home office setup. A conveniently located downstairs laundry room adds everyday ease. Residents enjoy access to exceptional community amenities, including parks, scenic walking trails, playgrounds, tennis and basketball courts, and a resort-style swimming pool. The HOA provides added value by covering lawn care, exterior painting, and the roof—offering low-maintenance living and peace of mind. Ideally located just minutes from Walt Disney World, this home offers the perfect blend of comfort, convenience, and location. Enjoy the magic of Disney with a short distance to a nearby viewing spot where you can take in the spectacular nightly Disney fireworks. Whether you're looking for a primary residence, vacation home, or investment property, this exceptional townhome places you close to world-class attractions, shopping, dining, and top-rated schools in one of Central Florida's most desirable communities. Motivated seller! This is one of the best values in the area—schedule your private showing today!

12966 Vennetta Way, Windermere

$1,825,000
5 Beds 6 Baths Reserve At Lake Butler Sound SubDv. 34786 Zip Code
Discover an exceptional expression of modern luxury in the heart of Windermere. Welcome to 11051 Hawkshead Court, gracefully positioned within the prestigious Reserve at Lake Butler Sound—an exclusive guard-gated enclave renowned for its elegance, privacy, and lakefront lifestyle. Set on an expansive half-acre homesite at the end of a cul-de-sac, this fully reimagined contemporary estate offers a seamless blend of sophistication and comfort. Spanning a thoughtfully designed single-story layout, the residence features five bedrooms, four full baths, and two half baths, all curated with impeccable attention to detail. From the moment you enter, soaring ceilings and an abundance of natural light highlight exquisite porcelain marble flooring that flows seamlessly throughout the main living areas—completely carpet-free for a clean, modern aesthetic. The bedrooms feature rich hardwood flooring, adding warmth and contrast. The open-concept design creates an inviting yet refined atmosphere, ideal for both intimate living and grand entertaining. At the heart of the home, the gourmet chef’s kitchen is a true showpiece, appointed with premium Viking stainless steel appliances, rich granite countertops, and bespoke custom cabinetry. Whether hosting elegant gatherings or enjoying everyday moments, this space is designed to impress. Step outside to your private resort-style sanctuary. The covered lanai, complete with a fully equipped outdoor kitchen and grill, overlooks a beautifully redesigned pool framed by lush, mature landscaping—creating a serene and secluded backdrop for relaxation or entertaining under the Florida sun. This home has been extensively upgraded with no detail overlooked, including a complete pool renovation with new equipment, a new screen enclosure, fresh exterior paint and lighting, two new HVAC systems, updated garage interiors and openers, EV charging capability, a new septic system, and a reverse osmosis water treatment system. Residents of this distinguished community enjoy 24-hour guard-gated security, private fishing dock on Lake Butler, and impeccably maintained surroundings—all just minutes from world-class attractions, fine dining, upscale shopping, top-rated schools, and major thoroughfares. This is more than a home—it is a statement of refined living in one of Central Florida’s most coveted addresses. Schedule your private tour today and experience it for yourself.

11051 Hawkshead Court, Windermere

$5,500,000
4 Beds 5 Baths Isleworth SubDv. 34786 Zip Code
Set along Isleworth’s signature 12th fairway, this fully reimagined estate captures the essence of refined golf course living within the renowned Isleworth Golf & Country Club—recognized among the finest private club communities in the world. Encompassing more than 4,300 square feet, the single-story residence has been completely transformed inside and out. Thoughtfully redesigned interiors showcase all-new flooring throughout, beautifully renovated bedrooms and baths, and a striking glass-enclosed wine tower serving as a true centerpiece that is both functional and an unforgettable conversation element anchoring the main living spaces. Every detail throughout the home has been elevated, from designer lighting installations that bring character and sophistication to each room, to the seamless flow of living and entertaining spaces. The kitchen is a true showpiece, featuring all-new appliances—including a striking black range with matching hood, refrigerator, and microwave—all accented with elegant gold detailing for a bold, designer-forward statement. Custom cabinetry is paired with exquisite countertops, highlighted by a dramatic waterfall-edge island that anchors the space and seamlessly blends everyday functionality with elevated, modern style.The outdoor living area features a reimagined pool and all-new pool deck creating a resort-style setting, perfectly positioned to take in breathtaking sunsets over the golf course and water. The half-acre homesite has been thoughtfully cleared and fenced to maximize both privacy and panoramic views, offering an exceptional backdrop for everyday living and entertaining alike. Framed by the fairways, the residence captures views of Lake Brenda - also known as Hourglass Pond - a small, privately maintained 10-acre water body that serves as a peaceful and picturesque part of the community setting. Additional features include a home office, in-home laundry room, and a three-car garage. Residents of Isleworth enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes, with access to world-class golf, dining, and amenities, all just moments from Central Florida’s premier shopping, dining, and entertainment destinations.

5138 Fairway Oaks Dr, Windermere

$4,190,000
3 Beds 5 Baths Gardens/Isleworth Un #2 SubDv. 34786 Zip Code
Welcome to an exceptional opportunity within the gates of Isleworth, one of Central Florida’s most Acclaimed private golf communities. Perfectly positioned along a tranquil pond and scenic walking trail, this move-in ready residence offers a rare blend of privacy, natural beauty, and refined living in the heart of Windermere. Thoughtfully designed for both everyday comfort and elevated entertaining, the home features a versatile layout including a spacious primary suite, multiple guest bedrooms, an oversized office/playroom, and a dedicated theater room. Expansive living areas flow seamlessly, creating a warm yet Elegant atmosphere throughout—all easily accessible via a private elevator connecting the home’s levels. The home delivers a true turnkey experience with modern finishes and enhancements, including a fully upgraded Crestron smart home system providing whole-home audio and video distribution for effortless control and convenience. A standout feature is the exceptional garage capacity, offering four individual single-car garages two of which are equipped with vehicle lifts. The outdoor living experience is a true highlight, featuring a resort-style pool, generous covered entertaining spaces, and serene water views that create a peaceful and private backdrop. Whether enjoying quiet mornings by the water or hosting guests in the evening, the setting is both inviting and unforgettable. Located within Isleworth—renowned for its championship golf course, world-class amenities, and guard-gated privacy—residents enjoy an unparalleled lifestyle surrounded by the Butler Chain of Lakes and beautifully manicured grounds. This is a rare opportunity to own a fully updated, move-in ready home that seamlessly combines luxury, technology, and exceptional outdoor living in one of Orlando’s most sought-after communities.

4906 Aviva Garden Court, Windermere

$2,450,000
6 Beds 4 Baths Weatherstone On Lake Olivia SubDv. 34786 Zip Code
Set within the private gates of Weatherstone on Lake Olivia, this stunning spring fed lakefront residence offers a rare opportunity to enjoy refined living along the peaceful shoreline of Lake Olivia in Windermere. Situated on an expansive lakefront homesite, an increasingly rare find in this area, the property provides exceptional space, privacy, and unobstructed water views. Boasting 6 bedrooms and 4 full baths, the home blends classic design with thoughtful updates and an inviting, functional layout. A charming wraparound front porch creates a warm first impression, surrounded by mature landscaping and tranquil views, perfect for relaxing mornings or unwinding at the end of the day. Inside, natural light fills the home, highlighting soaring ceilings, rich wood flooring, plantation shutters, crown molding, and carefully curated designer details. The open concept design allows for effortless flow between the main living spaces, many of which capture picturesque lake views. At the center of the home, the updated kitchen serves as a true gathering place, featuring generous prep space, a large island, stainless steel appliances, and a spacious dining area. Two oversized walk in pantries, one with a concealed bar, offer both convenience and a touch of character. The primary suite is located on the first floor, offering serene lake views, a spacious custom closet, and a beautifully redesigned bathroom with dual quartz vanities, a soaking tub, and a walk in shower. The first floor also includes a private office with custom built ins, an additional family room, or optional formal dining space, and a full bath. Upstairs, a well planned layout provides flexibility and privacy with five secondary bedrooms, some connected by updated Jack and Jill baths, plus a dedicated workspace with built in features on the landing area. An additional oversized bonus room with closet can easily function as a media room or play space. The home previously had a large loft area which could quite easily be converted back. Additional highlights include a first floor laundry room, abundant storage throughout, an updated tile roof, refreshed exterior paint, and a three car garage with epoxy flooring and built in storage. Designed for entertaining, the outdoor living space features a covered lanai, summer kitchen, resort style pool, fire pit, artificial turf dog run, and a Trex dock with boat lift, all overlooking the calm waters of Lake Olivia, where you can water ski, have fun on your boat or jet ski’s or just enjoy a calm ride on your paddle boards, the fun is endless. The gently sloping homesite enhances the home’s elevated position, maximizing lake views while naturally directing rainwater away from the property, an often overlooked advantage in Florida lakefront living. It also adds character to the outdoor space, creating a more dynamic and enjoyable setting for both relaxation and play. With only 13 homes, Weatherstone Ct offers a boutique gated setting just moments from local favorites like The Yellow Dog Eats, parks, top rated schools, and the heart of Windermere. This is lakefront living at its finest, private, spacious, and beautifully appointed. Ideally located with direct access to all the major highways, the home provides seamless connectivity to destinations throughout Central Florida and beyond, while still maintaining a quiet, tucked-away feel.

9648 Weatherstone Court, Windermere

$12,999,999
9 Beds 16 Baths Windsor Hill SubDv. 34786 Zip Code
Under Construction. Under Construction. Experience unmatched privacy, prestige, and personalization with this brand-new mansion on 2.5 pristine acres in the heart of Windermere. Tucked against protected government land that can never be developed, this estate offers the serenity of untouched nature with the ultimate in luxury living.Two Pools one outdoor with a swim up bar and grill area and the other indoor pool with a spa and massage room ! Highlights: • Custom-built mansion in progress — secure it now to choose your colors, flooring, cabinetry, countertops, lighting, and finishes • Private helicopter pad for seamless arrival and departure • Luxury bowling alley in development — your private entertainment retreat of turn into extra car show storage garage area ! • Grand open floor plan, soaring ceilings, and estate-level architecture • Massive gourmet kitchen + walk-in pantry, ideal for chef-level entertaining • Space for home theater, gym, wine cellar, or guest quarters • Oversized garages and motor court • For our equestrian lovers, you are permitted one horse for each acre. Location Perks: • Situated in one of Windermere’s most coveted neighborhoods • Minutes to Lake Butler Chain, championship golf, and elite private schools • Close to Winter Garden Village and exclusive dining/shopping This is a rare opportunity to own a truly bespoke estate before completion — where every detail is yours to design, and your view is forever protected. Inquire now for private plans, customization walkthrough, and completion timeline. Step into your own private paradise with this one-of-a-kind resort-style property featuring every amenity for ultimate relaxation and recreation. Highlights include: • Lagoon-style pool with a swim-up bar, perfect for hosting or unwinding in luxury • Private spa sanctuary with a designated massage room and indoor heated pool, offering year-round wellness experiences • Full-size tennis court for active days and fun with friends or family • Charming barn – ideal for equestrian use, storage, or a stunning rustic event space Whether you’re dreaming of daily spa treatments, evening swims under the stars, or tennis matches followed by cocktails poolside, this property delivers the ultimate blend of luxury and leisure.

9621 Windy Ridge Road, Windermere

$510,000
3 Beds 3 Baths Lakes Windermere Ph 01 49 108 SubDv. 34786 Zip Code
Price Reduced 10K for a quick sale. Seller very Motivated ! Welcome to this stunning 2-story home in the highly desirable Lakes of Windermere, featuring 3 bedrooms, 2.5 bathrooms, and a spacious bonus room that can easily serve as a home office, gym, media room, or playroom. The expansive primary suite offers soaring vaulted ceilings, a large walk-in closet, and a spa-inspired in-suite bathroom with a relaxing jacuzzi tub. Upstairs, you'll find beautiful wood flooring throughout—no carpet—along with elegant plantation shutters that add warmth and timeless style to every room. Thoughtfully updated for comfort and peace of mind, this home features impact windows, stainless steel appliances, Laundry room with washer and dryer, and ceiling fans in both the living room and primary suite. Step outside to your private, fully fenced backyard—perfect for entertaining, family gatherings, or simply relaxing. Enjoy a mature mango tree, a charming pergola, and an irrigation system using reclaimed water to keep the landscaping lush while conserving resources. The extended rear driveway with alley access provides generous guest parking, while the 2-car garage offers epoxy flooring, built-in storage cabinets, an extra refrigerator, and a new garage door opener for added convenience. Located in the sought-after Lakes of Windermere community, residents enjoy beautifully maintained parks, Gazebo, scenic lake Sawyer View, playgrounds, and a Community Recreation Area with pool, tennis, volleyball and basketball. Nestled House on a quiet single-entry loop surrounded by elegant homes, this property is just minutes from shopping, dining, top-rated schools, Disney, and major roadways.

6820 Thornhill Circle, Windermere

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