A highly sought after place to live, Windermere, FL is steeped in a rich history that helps give the town its modern charm. 

Founded in 1887, Windermere prides itself on many of its historical sites, from its Town Hall (built from 1922-1924), which began as The Women's Club, to Cal Palmer's office Building (completed in 1911), to the Parramore House, also known as the Historic 1890 Windermere Schoolhouse, which became the first school in the Town of Windermere.

$1,270,000
6 Beds 5 Baths Palms/Windermere SubDv. 34786 Zip Code
Experience elevated Florida living in this extraordinary 4,585-square-foot estate, ideally positioned in the heart of Windermere and just 2 miles from Magic Kingdom. Built in 2025 and presented in pristine, like-new condition, this remarkable residence offers an exceptional combination of sophisticated design, expansive living spaces, and an enviable location. Every detail has been thoughtfully considered to create a home that is as impressive as it is functional. From the moment you enter, the scale and elegance of this residence are immediately apparent. The expansive floor plan features six generously sized bedrooms, a dedicated private office, and a substantial bonus room, providing an extraordinary level of flexibility for today's lifestyle. The separate office is ideal for working from home, while the spacious bonus room can easily be transformed into a home gym, media room, children's playroom, or additional entertainment space. Upstairs, an impressive nearly 600-square-foot loft creates an entirely separate living and entertainment experience. Complete with a built-in wet bar, this remarkable space is perfectly suited for movie nights, game days, entertaining guests, or simply relaxing with family. Designed with modern luxury and everyday convenience in mind, the home features a dedicated laundry room on each floor, an abundance of additional closets, a large walk-in pantry, and generous garage space. There is no shortage of room for storage, hobbies, vehicles, and everything that comes with an elevated lifestyle. Perhaps the most exceptional feature is the location. Situated just minutes from Walt Disney World, you can enjoy the convenience of being only 2 miles from Magic Kingdom while even taking in the spectacular nightly Disney fireworks from your own home. The community also offers a playground, providing a wonderful space for children to play and enjoy the outdoors. At the same time, you'll be close to the highly sought-after Windermere school district, shopping, dining, golf, and everything Central Florida has to offer. Impeccably maintained, exceptionally spacious, and truly move-in ready, this stunning Windermere residence delivers a rare combination of luxury, convenience, and location. With six bedrooms, a dedicated office, a massive bonus room, an expansive loft with wet bar, two laundry rooms, and extraordinary storage, this is a home designed to accommodate both grand entertaining and effortless everyday living.

14360 Crest Palm Avenue, Windermere

$639,500
4 Beds 3 Baths Lakes/Windermere Ph 02a SubDv. 34786 Zip Code
WATER-VIEW SETTING + NIGHTLY MAGIC KINGDOM FIREWORKS + PRIME WINDERMERE LOCATION! Welcome to 12909 Cragside Lane, a beautifully renovated 4-bedroom, 2.5-bath, 2,460-square-foot single-story home in Lakes of Windermere. Located directly across from a neighborhood pond and fountain, the home offers a uniquely Central Florida setting with nightly views of the Magic Kingdom fireworks just steps from your front door. The exceptional location also provides convenient access to highly regarded public and private schools, childcare, Horizon West amenities and Walt Disney World. This move-in-ready home has been extensively updated, with many of the major expenses of homeownership already completed. Improvements include a new roof, HVAC system, water heater, Resideo smart WiFi thermostat, interior and exterior paint, hard-surface flooring throughout with no carpet, light fixtures and ceiling fans — all in 2021; new refrigerator, range/oven, dishwasher, washer and dryer, backyard fencing, paver outdoor-living area and gazebo in 2023; new kitchen countertops and guest-bath flooring, countertop, sinks and faucets in 2025; and refreshed front and rear landscaping and AT&T Fiber wiring in 2026. The fencing, paver improvements, gazebo and landscaping were reviewed and approved through the community HOA architectural-review process. Inside, the bright and spacious floor plan features an open kitchen and family room along with additional flexible living spaces ideal for a home office, recreation, entertaining or additional gathering space. Crown molding, architectural details and updated finishes complement the extensive mechanical and cosmetic improvements throughout. The fenced backyard provides an inviting extension of the living space with its paver patio, gazebo and refreshed landscaping, while the covered front porch faces toward the peaceful pond and fountain setting. Lakes of Windermere offers a community pool, parks, playgrounds, tennis and basketball courts, sidewalks and recreational spaces. The location is especially convenient to Sunset Park Elementary, Horizon West Middle School and Windermere High School, with Windermere Preparatory School also nearby, along with multiple daycare and early-learning options approximately a mile from the home. Shopping, dining and recreation throughout Horizon West are close at hand, while Walt Disney World and Magic Kingdom are just minutes away. With its water-view setting, nightly Disney fireworks, extensive renovations, newer roof and major systems, hard-surface flooring throughout, upgraded outdoor living spaces, excellent school access, fiber connectivity and highly convenient Windermere location, 12909 Cragside Lane offers an exceptional combination of lifestyle, location and move-in-ready condition.

12909 Cragside Lane, Windermere

$1,399,900
5 Beds 3 Baths Lake Down Cove SubDv. 34786 Zip Code
Virtually Staged. Set on just over an acre in Windermere, this updated 5-bedroom, 3-bath pool home offers 3,356 square feet of living space, plus a separate flex/bonus room that can be used as a media room, game room, office or additional living space. Located on a cul-de-sac in Lake Down Cove, the property offers something increasingly hard to find in Windermere: an updated home with a private pool, a flexible floor plan and more than an acre of land. Inside, high ceilings and large windows bring in plenty of natural light, while large-format marble-look porcelain tile runs throughout the main living areas. The spacious family room features a modern linear electric fireplace and opens to the kitchen and casual dining area, with views of the pool and backyard. A separate dining room is located just off the entry, and an interior Juliet balcony from the second floor overlooks the family room. The updated kitchen features dark shaker-style soft-close cabinetry, quartz countertops, a large island, farmhouse sink and glass tile backsplash. A six-burner ZLINE gas range with griddle, pot filler and stainless steel hood anchors the cooking area, along with double ovens, a microwave drawer and stainless steel appliances. Three of the five bedrooms are located downstairs, including the primary suite. The primary bedroom overlooks the pool and features crown molding, two walk-in closets and double doors leading outside. The primary bathroom includes dual vanities with quartz countertops, a freestanding soaking tub and a large frameless glass shower finished with marble-look porcelain tile. Two additional bedrooms and a second full bathroom are also downstairs, with one bedroom well suited for use as a home office. The second bathroom has direct access to the pool area. Upstairs are two additional bedrooms, a full bathroom and a separate flex room that could be used as a media room, game room, office or additional living area. The upstairs bathroom features a dual vanity with quartz countertops, a tub/shower combination and updated finishes. One of the upstairs bedrooms also features a private outdoor balcony and an interior Juliet balcony overlooking the family room below. Outside, the 1+ acre lot provides plenty of room to enjoy the property. The private pool is surrounded by a large patio with a partially covered area, while the fenced backyard offers mature trees and generous open space. The outdoor kitchen includes a built-in grill, refrigerator, sink, stone surround and counter space, and a wood-burning fire pit adds another gathering area in the backyard. Additional features include a downstairs laundry room with quartz countertops, sink and extensive cabinetry, plus an oversized two-car garage with workspace and additional storage. With five bedrooms plus a flex room, 3,356 square feet, an updated interior, private pool and more than an acre of land, this Windermere home offers an uncommon amount of space both inside and out. Conveniently located near shopping, dining, community events and major roadways, with easy access throughout Windermere and the greater Orlando area.

2540 Hempel Cove Ct, Windermere

$710,999
4 Beds 4 Baths Lake Sawyer South Ph 01 SubDv. 34786 Zip Code
*This home can be purchased with NO INCOME VERIFICATION.* Welcome to 13239 Jervey Street, an elegant 4-bedroom, 3.5-bath residence offering 2,745 square feet in the highly sought-after Lake Sawyer South community of Windermere. A grand entry with soaring ceilings, crown molding, and refined formal living and dining spaces sets a sophisticated tone from the start. The chef-inspired kitchen showcases granite countertops, 42-inch cabinetry, stainless steel appliances, a breakfast bar, and casual dining nook, seamlessly opening to the expansive family room—an ideal setting for both entertaining and everyday comfort. Abundant natural light extends to the screened lanai and private backyard, enhancing indoor-outdoor living. The main-level owner’s suite is a private retreat featuring generous proportions, a large walk-in closet, and a spa-style bath with dual vanities, soaking tub, and separate glass-enclosed shower. Upstairs, three additional bedrooms and a versatile loft provide flexible space for work, media, or relaxation. Additional highlights include an interior laundry room, three-car garage, extended driveway, and ample storage throughout. Residents of Lake Sawyer South enjoy community amenities including a pool, playground, sidewalks, and beautifully maintained surroundings. Ideally positioned near Horizon West, Winter Garden, premier shopping and dining, major highways, and Central Florida attractions, this home offers both convenience and lifestyle appeal. A refined Windermere address with spacious design, upscale finishes, and exceptional versatility—13239 Jervey Street delivers elevated Florida living at its finest.

13239 Jervey Street, Windermere

$600,000
4 Beds 3 Baths Summerport Phase 1 SubDv. 34786 Zip Code
Fresh interior/exterior paint and HVAC serviced! Residing in Summerport, this delightful home features a practical design with spacious room sizes and a tranquil pond view, providing the ideal atmosphere for everyday living and entertaining guests. Four comfortable bedrooms in tandem with multiple living areas and two covered patios offer ample space for any occasion, while granite countertops, extensive cabinetry, and custom accents throughout add an elegant touch to the interior. Summerport offers residents a list of amenities, including a clubhouse, community pool, sports courts, and multiple trails, parks, playgrounds, and dog parks for endless fun without leaving the neighborhood. Beyond these exceptional amenities, the location provides easy access to daily necessities, medical services, recreation activities, and major highways. The Summerport Village, Winter Garden Village, Shoppes at Lake Butler, and Shoppes at Windward Cay are moments away, placing numerous dining and retail needs right at your fingertips. Nearby Braddock Park and Tibet-Butler Nature Preserve provide natural beauty and outdoor activities close by, while just moments from Disney and Universal, making it ideal for those seeking both tranquil residential living and entertainment accessibility. This combination of a practical design, peaceful pond view, quality amenities, and strategic positioning creates the ideal living experience. Don't let this exceptional opportunity slip away – schedule your private showing today!

13844 Amelia Pond Drive, Windermere

$550,000
5 Beds 4 Baths Royal Estates SubDv. 34786 Zip Code
Welcome to this beautifully appointed corner-unit townhome in the highly sought-after area of Windermere, Florida! Ideally located just 15 minutes from Walt Disney World, Hamlin Town Center, and an incredible selection of shopping, dining, entertainment, and everyday conveniences, this home offers the perfect combination of comfort, location, and lifestyle. As a desirable corner unit, the home provides added privacy and an abundance of natural light throughout. Featuring 5 bedrooms and 3.5 bathrooms, this spacious townhome offers a thoughtfully designed open-concept floor plan perfect for both everyday living and entertaining. The first floor includes a dedicated office, ideal for working from home, along with generous living and dining spaces that flow seamlessly into the kitchen. One of the home's standout features is the beautiful in-law suite, complete with its own private entrance, providing an ideal space for extended family, guests, or additional flexibility. Upstairs, the spacious primary suite offers a peaceful retreat along with a versatile loft area that can be used as a secondary living space, playroom, media area, or home gym. With three additional bedrooms upstairs, there is plenty of room for everyone. A two-car garage provides ample parking and storage, while the home's prime Windermere location puts you close to everything Central Florida has to offer. Whether you're looking for a primary residence, multigenerational living, or a fantastic investment opportunity, this townhome is a must-see!

9021 Via Di Canti, Windermere

$1,159,000
4 Beds 4 Baths Westside Village SubDv. 34786 Zip Code
Beautifully upgraded 4-bedroom residence featuring a thoughtfully designed floor plan, custom finishes, and exceptional indoor-outdoor living. The main level offers a private en-suite bedroom, ideal for guests or multigenerational living, along with a dedicated home office, spacious living areas, and a beautifully designed custom kitchen featuring tailored cabinetry, a large center island, integrated lighting, and generous storage. A separate TV/media room provides the perfect space for movie nights, entertainment, or relaxing with family. Upstairs, the spacious primary suite offers a private retreat with a truly special feature: Disney fireworks can be enjoyed right from the comfort of your bed. The suite also includes a generous walk-in closet and a spa-inspired primary bathroom featuring a freestanding soaking tub, dual vanities, and an oversized shower with separate his-and-hers shower fixtures. Extensive custom details can be found throughout the home, including Italian wallpaper, custom window treatments, bespoke cabinetry, decorative wall paneling, wood accents, designer lighting, and integrated LED lighting. Every element has been thoughtfully selected to create a comfortable contemporary interior. Designed for the Florida lifestyle, the outdoor living space features a spacious covered lanai with plenty of room for dining and lounging, overlooking the private heated pool and landscaped backyard. The seamless connection between the indoor and outdoor spaces makes this home equally suited for everyday living and entertaining. With a first-floor en-suite bedroom, dedicated office, media room, custom-designed kitchen, extensive interior upgrades, heated pool, and Disney fireworks views from the primary suite, this home offers an exceptional combination of style, comfort, and functionality. Thoughtfully customized and beautifully maintained, this is a home designed to be enjoyed inside and out.

12989 Westside Village Loop, Windermere

$529,000
3 Beds 2 Baths Summerport Ph 05 SubDv. 34786 Zip Code
Don’t miss the opportunity to make this beautiful home in the highly sought-after Summerport community your own! Known for its A-rated schools, picturesque surroundings, and outstanding amenities. This well-maintained 3-bedroom, 2-bath home features a versatile office/den, offering flexible space to accommodate a home office, or guest room. The home features vinyl flooring throughout with no carpet, providing a clean, stylish, and low-maintenance living environment. The kitchen is equipped with a natural gas stove, perfect for those who enjoy cooking with gas. Recent improvements include a newer roof, newer A/C system, and freshly painted exterior, offering added comfort and peace of mind. From the moment you enter the welcoming foyer, you’ll appreciate the bright and open floor plan. Two secondary bedrooms are conveniently located toward the front of the home, providing separation and privacy from the primary suite. Continue down the hallway to the spacious formal living room and flexible additional living space, perfect for adapting to your family’s needs. The private primary suite offers a relaxing retreat with a walk-in closet, dressing area, and ensuite bathroom featuring dual sinks and a spacious standing glass shower. The kitchen seamlessly connects to the bright family and dining areas, creating an inviting space filled with natural light and perfect for everyday living and entertaining. The natural gas stove adds an extra touch of convenience for the home chef. Sliding glass doors open to the covered porch, extending the living space outdoors and overlooking the spacious backyard—an ideal setting for relaxing, entertaining, or enjoying the Florida lifestyle. Summerport offers an impressive array of resort-style amenities, including a community pool, fitness center, parks, playgrounds, fishing pier, and scenic walking trails. The community’s desirable location provides easy access to Windermere, Winter Garden, and Clermont, with an abundance of shopping, dining, entertainment, recreation, and highly rated schools nearby. Commuters will appreciate the convenient access to major roadways, including Highway 429, the Florida Turnpike, SR 408 (East-West Expressway), and I-4, making it easy to travel throughout Central Florida. Walt Disney World and many of Orlando’s world-renowned attractions are also just a short drive away. For Disney enthusiasts, enjoy the added bonus of being just minutes from Walt Disney World, with the opportunity to catch the nightly fireworks from select areas within the community. With vinyl flooring throughout and no carpet, a natural gas stove, a newer roof, newer A/C, freshly painted exterior, flexible living spaces, spacious backyard, desirable location, and exceptional community amenities, this home offers an outstanding opportunity in Summerport. Schedule your private showing today and come see all this home has to offer!

4844 Flint Road, Windermere

$1,895,000
4 Beds 5 Baths Windermere Town SubDv. 34786 Zip Code
Set along the shores of Lake Bessie in the heart of Downtown Windermere, this contemporary lakefront residence pairs clean architectural design with effortless single-story living. Completed in 2024, the home offers 2,868 square feet with four bedrooms, each featuring a private en-suite bath, along with a dedicated home office and an open-concept layout designed around the water views. Inside, wide-plank white oak hardwood floors, soaring ceilings and expansive black-framed glass doors create a bright, modern aesthetic while drawing the lake into the main living areas. The European-inspired kitchen anchors the home with an oversized island, quartz countertops, sleek cabinetry and smart appliances, flowing seamlessly into the dining and living spaces for easy everyday living and entertaining. The primary suite continues the home's refined design with a spa-like bath featuring a freestanding soaking tub, floating wood vanity, dual sinks and an oversized walk-in shower. Contemporary finishes and a light, neutral palette carry throughout the residence. Outdoors, a private heated pool and spa create a resort-like retreat, while the lakefront setting offers approximately 100 feet of frontage on Lake Bessie with the option to add a private dock. There is also a two car covered parking area with EV Charger. From morning sunrises and lake breezes to afternoons spent boating or fishing, the setting captures the relaxed lifestyle that makes Windermere so desirable. Just a short walk or golf cart ride from Downtown Windermere, the home places the weekly farmers market, parks, tennis courts, boat ramp to Lake Butler and Bessie, dining, local shops and a brewery within easy reach. Modern architecture, direct lake frontage and an exceptional in-town location come together for a rare opportunity to experience contemporary waterfront living in Windermere

930 East Boulevard, Windermere

$410,000
3 Beds 3 Baths Lakes Of Windermere Lake Reams Townhomes Phase 3 SubDv. 34786 Zip Code
Beautiful end-unit townhome in Windermere featuring the larger floor plan in the Lake Reams Townhomes community. This well-maintained 3-bedroom, 2.5-bath home offers plenty of natural light and a spacious open-concept kitchen, dining, and living area combo. The kitchen features granite countertops, tiled travertine back splash 46" wood cabinetry, and ceramic tile flooring, with kitchen and laundry appliances included. Upstairs, feel the new plush padded carpeting in the bedrooms, hallway and stairs. The spacious primary suite includes dual vanities, quartz counter top, a large walk-in closet, and walk-in shower. The guest bathroom also has a tub and shower, a single sink with a quartz counter top. Outside, enjoy a private Vinyl fenced in courtyard leading to an oversized rear-entry 2-car garage. The HOA provides low-maintenance living and includes exterior and roof maintenance, landscaping, exterior pest control, and access to the community’s Junior Olympic-size pool. Located approximately 5 minutes from Walt Disney World’s Magic Kingdom, with the added fun of being able to hear and see the Magic Kingdom fireworks each evening. Convenient to Lakeside Village, Horizon West, Winter Garden Village, shopping, dining, major roadways, and highly rated local schools. A great opportunity to enjoy a spacious Windermere townhome in an incredibly convenient location.

8641 Brookvale Drive, Windermere

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