Location: Windermere
Do Not Show Listings
1316 ESTANCIA WOODS LOOP, WINDERMERE, FL 34786
$2,380,00024 Days on yellowkey MLS ID: S5146178
Bed: 5 Bath: 6.5 Gar: 2 Liv Area Sq Ft: 5108 Built: 2019Monthly Fee: $250 Tax: $1,982 (2025)Community: Estancia/WindermereSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,982
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Elegant and spacious home in the highly sought after Estancia at Windermere community, offering the perfect blend of luxury, comfort, and prime Central Florida living. This home is being offered fully furnished, providing a truly turnkey, move in ready experience. Built in 2019 on an oversized homesite, this beautifully appointed residence showcases modern architecture, generous living areas filled with natural light, and high end finishes throughout. The open concept layout is ideal for both everyday living and entertaining, with a gourmet style kitchen, elegant dining spaces, and seamless flow to the outdoor living area. Enjoy Windermere’s signature lifestyle just minutes from top rated schools, charming downtown Windermere, and world class Orlando attractions, including Walt Disney World and Universal Studios. Estancia is a boutique community of luxury homes featuring a private, serene atmosphere with conservation surroundings, while still offering quick access to major highways, shopping, dining, parks, and the Butler Chain of Lakes. This is an outstanding opportunity to own a stylish, fully furnished, move in ready home in one of Windermere’s most desirable neighborhoods.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Catalina Gomez (407-289-9029)
8520 GREENBANK BLVD, WINDERMERE, FL 34786
$549,90015 Days on yellowkey MLS ID: O6396673
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1726 Built: 2004Monthly Fee: $170 Tax: $6,960 (2025)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$6,960
Elementary School: Bay Lake Elementary
Middle School: Horizon West Middle School
Remarks: Beautiful and inviting home located in the heart of Windermere, nestled within a charming gated community. Enjoy the rare opportunity to watch Disney fireworks right from your own backyard. Designed for modern living, this home features an open-concept floor plan that flows seamlessly, perfect for both everyday comfort and entertaining. The fully fenced backyard offers privacy and the ideal space for family gatherings, barbecues, and outdoor enjoyment. Additional highlights include solar panels for enhanced energy efficiency, a spacious two-car garage, and a welcoming front porch perfect for relaxing. Residents enjoy access to community amenities including a sparkling swimming pool, playground, and beautifully maintained green spaces. Ideally located near top-rated A+ schools, as well as shopping, dining, and everyday conveniences, this home offers the perfect blend of comfort, efficiency, and location in one of Central Florida’s most desirable areas. Roof is 2024, Water Heater is 2025.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Umberto Da Cunha Neto (407-690-3539)
6315 CLEARMEADOW CT, WINDERMERE, FL 34786
$618,0009 Days on yellowkey MLS ID: O6398505
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2077 Built: 2002Monthly Fee: $170 Tax: $3,701 (2024)Community: Glenmuir 48 39Single Family
Taxes:$3,701
Tax Year: 2024
Remarks: One or more photo(s) has been virtually staged. Welcome to this beautifully maintained home in the gated community of Glenmuir in Windermere. Perfectly located just minutes from Walt Disney World, Universal Orlando Resort, SeaWorld Orlando, and the charming downtown areas of Winter Garden and Downtown Windermere, this location offers both luxury and convenience. Tucked away on a quiet cul-de-sac, this freshly painted 3-bedroom, 2-bath home offers 2,077 sq. ft. of move-in ready living space. The open-concept great room features retractable sliding glass doors that lead to a 350 sq. ft. covered and enclosed outdoor retreat, creating the perfect space for relaxing or entertaining. The spacious kitchen includes solid wood cabinetry, quartz countertops (2022), stainless steel appliances, and a new dishwasher (2025), along with a cozy breakfast nook. The primary suite offers a large walk-in closet and a spa-like bath with dual vanities, garden tub, and private water closet. Major upgrades include a brand-new Spanish tile roof (2025), sprinkler system upgrade (2025), hot water heater (2020), A/C (2017), new blown insulation, and new carpet throughout. The extended driveway fits six or more vehicles, ideal for hosting guests. Residents enjoy a beautiful tree-lined community with a park, playground, basketball courts, and convenient access to major highways including Interstate 4 and Florida's Turnpike. A rare opportunity to own a move-in ready home with luxury upgrades, a private cul-de-sac location, and an exceptional outdoor retreat in one of Windermere’s most desirable communities.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Jessica Otero, Pa (407-780-1663)
11334 CAMDEN LOOP WAY, WINDERMERE, FL 34786
$1,250,000127 Days on yellowkey MLS ID: O6367433
0 Days Off yellowkey (back on 4/22/2026)
REDUCED by $25,000 (2.0%) on 04/01/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3021 Built: 2005Monthly Fee: $298 Tax: $8,578 (2024)Community: Keenes PointeSingle Family
Taxes:$8,578
Remarks: Under contract-accepting backup offers. Nestled within the guard-gated community of Keene’s Pointe, this beautifully updated single-story home offers a well-designed, functional layout with tasteful upgrades throughout. Recent improvements include luxury vinyl flooring, updated lighting, fresh interior and exterior paint, and a new roof installed in 2024, making the home truly move-in ready. The open-concept kitchen and family room are filled with natural light and feature refinished cabinetry, granite countertops, stainless steel appliances, a gas range, and double ovens, flowing seamlessly through French doors to a screened pool and covered patio—perfect for both entertaining and everyday Florida living. The desirable split floor plan provides privacy, with a spacious primary suite overlooking the pool and offering multiple walk-in closets and a well-appointed en-suite bath with a soaking tub, large walk-in shower, and private toilet room, while three additional bedrooms and two full bathrooms are tucked away toward the rear of the home. Outdoors, the private pool area is enhanced with stacked river stone and a tranquil water feature, creating a serene retreat. Additional highlights include a laundry room conveniently located off the kitchen, an oversized three-car garage with freshly painted floors, and a welcoming front porch surrounded by mature oak trees. Residents enjoy 24-hour security, access to a community boat ramp on Lake Burden, scenic walking trails, and nearby parks, with optional membership available at the Golden Bear Club featuring golf, tennis, dining, and the Jack Nicklaus Signature Golf Course, all just minutes from top-rated schools and shopping at Lakeside Village Center.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
13420 BONICA WAY, WINDERMERE, FL 34786
$1,875,000209 Days on yellowkey MLS ID: O6347722
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4489 Built: 2006Monthly Fee: $297 Tax: $17,970 (2024)Community: Tildens GroveSpa: YesSingle Family
Taxes:$17,970
Remarks: Experience the Florida lifestyle in this stunning FULLY FURNISHED 5-Bed/4-Bath pool home on over 1/2-acre, with a welcoming open floor plan spanning 4,500 square feet, spectacular Theater Room, custom upgrades and designer accents throughout, and new AC system in August 2025. Situated across from the community park and tennis on one of the best waterfront lots in sought-after gated Tildens Grove, offering a perfect blend of privacy and serene panoramic views. Step into elegance in the light and bright formal Living Room enhanced by a stunning Fireplace, Pool and Lanai views, and high Coffered Ceiling. The equally exquisite Formal Dining Room is also adorned with a Coffered Ceiling and ample natural lighting. A beautiful open Island Kitchen at the center of this home, perfectly situated for accommodating and entertaining friends and family, boasts Granite Counters, built-in Wall Oven and microwave, granite back splash, abundant storage in 42" wood cabinetry with pull outs, 5 burner Gas Stove and high-end stainless appliances, built-in cabinet Pantry. The Kitchen opens to the Dinette area with large picture window overlooking the Lanai and Pool, and Family Room ideal for entertaining with Built-Ins, storage and gorgeous details with French Doors leading to the outdoor living space. Relax, play, or entertain outdoors in the voluminous Pool with Spa and expansive covered Lanai, providing shaded space perfect for enjoying refreshments as you gaze across the water. The spacious Owner’s Suite is a true retreat tucked away on one side of the home, including an elegant bedroom with Sitting Area, stately entertainment wall unit, Double-Tray Ceiling, handsome wood flooring, French Door access to Lanai, and a generous walk-in California Closet system with dressing space. The finely appointed, light-filled Ensuite Bath boasts split sink vanities, large walk-through dual-head shower, Jetted Garden Tub, and private water closet. On the opposite end, the 2nd and 3rd bedrooms share a convenient Jack and Jill bathroom. The private 4th bedroom with Ensuite Bath is perfect for your visiting guests. The 5th bedroom adjacent to the Foyer is currently utilized as a den/home office. Enjoy a home cinema experience in the fabulous 6-seat Theater Room, equipped with great acoustical audio, large movie screen, leather recliner seating, gorgeous Custom Millwork with concealed column storage, all overlooking the Scenic Pond. Located in the hallway between the Kitchen and Dining Room are 2 extravagant built-in Mahogany glass-front cigar Humidors including Wine Storage to display and preserve cherished collections. High ceilings and Crown Molding accents throughout exude a sense of grandeur. French Doors from multiple rooms let you open the home to the outdoors space. Large, covered Lanai with a built-in grill, sink and counter space, screen enclosed Pool and heated Spa with a panoramic pond view. The neighborhood is quiet and private, with 140 luxury homes, in the top school districts, centrally located for convenience to Windermere's dining, shopping and culture, local theme parks, 429, I-4, and Florida's Turnpike. Whether you're entertaining or seeking a peaceful retreat, this home delivers on every level.
Listing is courtesy of: FERRELL REALTY, INC. (407-628-3200)
Listing Agent: Frank Ferrell (407-227-2753)
2125 KANE PARK WAY, WINDERMERE, FL 34786
$975,000139 Days on yellowkey MLS ID: O6358139
REDUCED by $24,998 (2.5%) on 04/22/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2743 Built: 1992Monthly Fee: $118 Tax: $8,555 (2024)Community: Willows At Lake Rhea Ph 02Spa: NoSingle Family
Taxes:$8,555
Remarks: A rare opportunity to own a .71-acre pool home in the Town of Windermere for under $1 million—beautifully updated and truly move-in ready. Welcome to this beautifully updated single-story pool home on an oversized cul-de-sac lot in Windermere’s Willows at Lake Rhea, zoned for A-rated schools and offering exceptional privacy between homes. Surrounded by mature landscaping, the property provides a peaceful setting rarely found in newer communities while still offering convenient access to major roads, shopping, dining, and area attractions. Custom built by well-known luxury builder Richard Watson, this four-bedroom, three-bath home features a thoughtful layout with formal living and dining rooms, a spacious family room, and a custom pool — ideal for both everyday living and entertaining. Inside, high ceilings, Acacia wood flooring, and abundant natural light highlight the open floor plan with views of the pool and backyard. The formal living room features triple sliding glass doors for seamless indoor-outdoor living, while the formal dining room offers a double tray ceiling, crown molding, and bay window with convenient access to the kitchen and family room. The kitchen and family room feature vaulted ceilings and porcelain tile flooring, with French doors leading outdoors. The kitchen includes soft-close cabinetry, granite countertops, under-cabinet lighting, generous storage, and a stylish backsplash. A bright breakfast nook overlooks the pool, while the family room is anchored by a wood-burning fireplace with built-in shelving. The oversized owner’s suite offers direct access to the pool and a spa-inspired bathroom with a freestanding soaking tub, quartz dual vanities, a zero-entry walk-in shower, and dual custom closets. Two spacious bedrooms share a Jack-and-Jill bathroom with dual sinks, while the fourth bedroom with French doors and a bay window works well as an office, den, or playroom. A third updated bathroom also serves as a convenient pool bath. Outdoor living features a custom pebble-finish pool, spacious deck, and screened lanai with a coffered ceiling, sink, and cabinetry. The expansive backyard provides rare space and privacy between homes with room for recreation or future enhancements. Additional highlights include a laundry room with utility sink and storage, an expansive driveway, and a side-entry garage. The Willows at Lake Rhea is zoned for Windermere Elementary, Bridgewater Middle, and Windermere High, and offers community amenities including tennis and pickleball courts, basketball, playground, and park. Residents also enjoy the nearby library, farmers market, food truck nights, and seasonal events. Residents of the Town of Windermere enjoy access to the Butler Chain of Lakes boat ramp, offering entry to one of Central Florida’s most sought-after boating destinations. Conveniently located near SR-429, SR-408, Florida’s Turnpike, Disney, Universal, Winter Garden Village, and the shopping and dining of Dr. Phillips. Recent improvements include a new air-conditioning system (2025), water heater (2024), new irrigation and pool pumps (2025), and septic drainfield completed in 2018. With its large private lot, quality construction, desirable school zoning, and recent price improvement, this home presents an outstanding opportunity in one of Windermere’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)
Listing Agent: Deb Schroeder (407-234-2256)
6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786
$479,00030 Days on yellowkey MLS ID: O6392752
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1980 Built: 2008Monthly Fee: $315 Tax: $3,248 (2025)Community: Preston SquareTownhouse
Taxes:$3,248
Elementary School: Sunset Park Elem
Remarks: Welcome home to Preston Square in beautiful Windermere! This stunning corner-unit townhome with 4 bedroom, 3 bathrooms offers the perfect blend of comfort, style, and convenience, with a new roof and fresh exterior paint. Step onto the cozy front porch and into a bright, inviting two-story home filled with natural light. The main living areas feature tile flooring throughout; great room showcases a mirror accent wall along with board and batten in the dining area. Kitchen features granite countertops, breakfast bar, stainless steel appliances, and stone backsplash. Sliding glass door leads to a private paver patio, perfect for relaxing or entertaining. Downstairs bedroom with full bath, inside laundry room plus a utility sink leads to the attached two-car garage with long driveway for additional parking. Upstairs you will find 3 additional bedrooms, stunning primary suite with balcony views. Primary bath features dual sinks, large garden tub, and separate shower. Preston Square offers amenities including a stunning community pool, playground, mature landscaping, basketball court, green space for events, and fitness stations. Ideally located near local dining, shopping, top-rated schools, golf courses, hospitals, and major roadways and attractions.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Morgan Horsley (256-283-8747)
109 E 12TH AVE, WINDERMERE, FL 34786
$1,225,0008 Days on yellowkey MLS ID: O6394569
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2791 Built: 1989 Tax: $20,244 (2025)Community: Windermere TownSpa: YesSingle Family
Taxes:$20,244
High School: Olympia High
Middle School: Gotha Middle
Remarks: Modern style blends with Windermere charm. This totally renovated home is located just steps from Lake Bessie in the Town of Windermere. Set on a beautifully landscaped corner lot with no HOA, this home combines luxury and comfort in one of Central Florida’s most desirable communities. Every detail has been thoughtfully updated within the last 3 years to include roof, a/c, plumbing, flooring, drain field and water filtration system. Inside, sun drenched living and dining spaces flow seamlessly, anchored by a warm inviting fireplace setting the tone for relaxed living and effortless entertaining. The kitchen serves as the heart of the home, featuring soft gray shaker cabinetry, quartz countertops, a generous island with induction cooktop, hood, double wall ovens, mosaic glass backsplash and all new stainless appliances. Sliding doors open to a sparkling pool with sun deck and pergola, surrounded by lush landscaping in a private, fenced courtyard. Whether hosting gatherings or enjoying quiet evenings at home, this outdoor space delivers the true Florida lifestyle. Upstairs, the primary suite features a spa inspired bath with a freestanding soaking tub, rainfall shower, dual sinks, and elegant finishes. Additional bedrooms include an oversized fourth bedroom with its own fireplace and built-ins which easily can be used as a media room, office, or home gym. Located just a short walk or golf cart ride to Windermere shops, restaurants, lakefront parks, weekly farmers markets, library and more, this home places you at the center of it all. Surrounded by the Butler Chain of Lakes and close to renowned golf, fine dining and premium shopping. Windermere offers small town charm yet convenient to major roadways, area attractions and the International Airport. The location is as exceptional as the home itself. This is more than a residence; it is a refined Windermere lifestyle defined by comfort connection and enduring style.
Listing is courtesy of: UPSIDE REAL ESTATE INC (407-308-5750)
Listing Agent: Judy Black (407-810-1803)
13124 FILLY CT, WINDERMERE, FL 34786
$1,575,000363 Days on yellowkey MLS ID: O6303140
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3300 Built: 1989Monthly Fee: $46 Tax: $15,459 (2024)Community: FarmsSpa: NoSingle Family
Taxes:$15,459
Remarks: Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As you step up to the front entrance, you are greeted by beautiful water fountain. Once inside your living room with a wood burning fireplace welcomes you to your living room on the right. Continuing your way into the house, your inviting family room awaits with an eat in kitchen island completing the scene. The gourmet kitchen is a chef’s dream, outfitted with top-of-the-line appliances and plentiful cabinetry. Retreat to the oversized owner’s suite with double walk-in closets, a luxurious master bathroom and a private sitting area overlooking the pool area. Enjoy an enclosed pool area and expansive backyard. There is also a second master suite with private bathroom and walk-in closet. At the opposite end of the family room there is a hallway leading to another full bathroom and three additional bedrooms. Located just minutes from championship golf courses, downtown Windermere, Winter Garden Village, and top-rated schools, this home offers the perfect blend of tranquility and convenience. Don’t wait, schedule your showing today!
Listing is courtesy of: HOME N OFFICES INTERNATIONAL (407-864-4590)
Listing Agent: Marcelo Brandao (407-864-4590)
10870 BAYSHORE DR, WINDERMERE, FL 34786
$2,995,00083 Days on yellowkey MLS ID: O6371471
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4693 Built: 1999 Tax: $27,527 (2024)Community: Lake Down EstatesSpa: YesSingle Family
Taxes:$27,527
Remarks: Set against the shimmering waters of Little Lake Down, this extraordinary lakefront home offers an elevated expression of luxury living. Thoughtfully designed to maximize sweeping water views, the residence delivers a refined yet inviting atmosphere ideal for both intimate living and grand entertaining. As you step inside you are greeted by a spacious open floor plan, highlighted by a wood-burning fireplace, and captivating views of the pool, backyard, and lake. At the heart of the home, a chef’s kitchen stands as a true centerpiece, appointed with top-of-the-line appliances and two expansive center islands, it’s the perfect place for family gatherings. The kitchen opens to a large family room and breakfast nook providing effortless flow for daily living, enhanced by panoramic lake views that bring the outdoors in. The primary suite serves as a luxurious retreat, featuring peaceful water views and a spa-like bathroom with dual vanities, a walk-in shower, and an elegant soaking tub. Additional first floor amenities include a guest bedroom, a home office, and a pool bath. Upstairs, you will find two additional bedrooms, a spacious bonus room, and a private balcony overlooking the lake. Outdoor living rivals a private resort with a large, covered lanai, sparkling pool, spa, and an expansive backyard that leads to a private boat dock with a boat lift and jet ski parking. With direct access to the Butler Chain’s interconnected lakes there will be no shortage of things to do on the weekend. Enjoy being just minutes from Windermere A rated schools, the Friday farmers market, quaint eateries, and a short drive to world class shopping, fine dining, and the Disney and Universal theme parks. This is more than a home, it is a rare opportunity to own a private lakefront retreat on the Butler Chain of Lakes, where luxury, lifestyle, and location converge in one truly exceptional offering.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
3013 SEIGNEURY DR, WINDERMERE, FL 34786
$1,890,00080 Days on yellowkey MLS ID: O6377087
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 5130 Built: 2002Monthly Fee: $250 Tax: $24,337 (2024)Community: Harbor IsleSingle Family
Taxes:$24,337
Elementary School: Thornebrooke Elem
Remarks: Stylish and elegant with contemporary touches, welcome home to a magnificent and expansive retreat situated on a 1-acre lot, with full-size lighted sport court with double pickleball courts (or tennis or basketball), set inside the gated enclave of Harbor Isle. This spectacular residence is unduplicated for its secluded setting – yet so close to everything – while offering an abundance of amenities, right at home. Through the grand entrance, the formal living room is bright and chic, with ceiling niche lighting and picturesque windows to enhance the details of this beautifully-crafted estate. Formal living, wine bar, and fabulous chef’s kitchen with breakfast nook with built-ins, plus generously-sized family room enhance your largest gatherings and everyday living. The chef’s kitchen with island and preparation sink feature gas cooktop with hood, stainless appliances, and double ovens. The vast owner’s retreat spans the entire south wing of the house and includes a lovely sitting area, French doors to the patio, large walk-in closets, and a spa-like bath with double vanities, jetted tub, and large shower. Two additional bedrooms are located on the opposite side of the house on the first floor with a Jack and Jill bath and a secondary bed and bath are upstairs off a large game room. The resort-style pool and spa with mammoth paver patio decking and summer kitchen offers a private outdoor retreat under a large screen enclosure. New carpeting and new Plantation shutters just installed. Harbor Isle is an exclusive gated community of just 31 home sites, perched along the shores of Lake Down on The Butler Chain, and on the east side of Windermere offering easy access to downtown Orlando, theme parks, Restaurant Row, and the best shopping options in Central Florida.
9011 PINNACLE CIR, WINDERMERE, FL 34786
$2,250,0003 Days on yellowkey MLS ID: O6400872
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 6546 Built: 2002Monthly Fee: $172 Tax: $23,090 (2025)Community: Lake Down CrestSpa: YesSingle Family
Taxes:$23,090
Remarks: Majestic and stately, this castle inspired residence sits on a 1.2 acre homesite within the privately gated enclave of Lake Down Crest. Its commanding presence is defined by patterned stone and brickwork, gabled rooflines, slate accents, wooden beams, and a shimmering grand fountain that sets an unforgettable first impression. Double front doors open to an impressive foyer flanked by formal living and dining rooms, while a step down home theater or richly paneled den—with custom built ins—creates a dramatic focal point. The well appointed kitchen features an island with prep sink, stainless appliances, gas cooktop, pantry, and a bright breakfast nook, making it ideal for both entertaining and everyday living. The inviting family room showcases a fireplace, custom millwork, and wood flooring, with French doors that lead to a Travertine patio overlooking the pool, elevated spa with waterfall, iron fencing, and paver decking. The primary retreat is a sanctuary of its own, complete with a private entrance foyer, bedroom with ceiling niche, fireplace, alcove, separate den or nursery, and a luxurious bath featuring a double headed pass through shower, jetted tub, marble topped vanities, and a spacious walk in closet. A secondary guest suite is also conveniently located on the main level. Upstairs, three additional bedrooms accompany a massive bonus room over the garage—perfect as a game room, theater, sixth bedroom, or private guest wing. A rare Florida feature, the finished basement offers exceptional flexibility for a game room, office, or substantial storage. A four and a half car drive through garage provides entrances on both sides and abundant storage. The home is nestled within an exclusive 32 residence community in East Windermere, offering top tier schools and effortless access to SR 408, downtown Orlando, I 4, Mall at Millenia, Walt Disney World, Universal Orlando, and Central Florida’s premier attractions.
8632 ABBOTSBURY DR, WINDERMERE, FL 34786
$609,99993 Days on yellowkey MLS ID: O6374937
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2720 Built: 2004Monthly Fee: $167 Tax: $8,567 (2025)Community: Lakes/Windermere-PeachtreeSingle Family
Taxes:$8,567
Remarks: **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Welcome to 8632 Abbotsbury Drive, a beautifully situated 4-bedroom, 3.5-bath residence offering 2,720 square feet of heated living space in the heart of Windermere, one of Central Florida’s most desirable communities. This well-maintained home features an open floor plan that creates a bright, airy feel and allows for effortless flow between the main living areas, making it ideal for both everyday living and entertaining. Spacious rooms are filled with natural light, enhancing the home’s inviting atmosphere. The property includes a 2-car garage, providing convenience and ample storage. At the rear of the home, a screened-in patio offers a peaceful outdoor retreat, surrounded by mature trees and lush, well-maintained landscaping that delivers privacy and a serene setting. Located in a well-established neighborhood, this home offers easy access to top-rated schools, shopping, dining, and nearby attractions. With its open layout, mature landscaping, and prime Windermere location, 8632 Abbotsbury Drive is a wonderful opportunity to enjoy comfortable Florida living at its best.
Listing Agent: Thomas Nickley, Jr (407-629-4420)
5825 OXFORD MOOR BLVD, WINDERMERE, FL 34786
$1,500,0007 Days on yellowkey MLS ID: O6399697
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4319 Built: 2002Monthly Fee: $183 Tax: $16,530 (2025)Community: Oxford MoorSpa: YesSingle Family
Taxes:$16,530
Remarks: Completely Remodeled 2022 | Single Story |Gated Windermere Community | Set on nearly three-quarters of an acre in the gated Oxford Moor community, this fully remodeled single-story home delivers the kind of space and finish level that's genuinely hard to find. Wide-open living areas, high ceilings, oversized rooms, and a modern aesthetic. The kitchen provides a large island, full stone backsplash, Bosch appliances with induction cooktop and double ovens, and a dedicated coffee bar. The split floorplan separates the primary suite from the secondary bedrooms, each generously sized, while the living areas flow directly to the covered lanai and saltwater pool. The primary suite includes a sitting area, expanded closet, and a fully renovated bath. A large private office comfortably fits dual workstations. Outdoor living space includes the saltwater pool running on updated equipment and automation, surrounded by a spacious fenced yard framed by mature landscaping and fruit trees that actually produce. Oxford Moor is one of Windermere's quieter gated communities comprised of 85 Estate Homes. Top-rated schools including Windermere Elementary, Bridgewater Middle, Windermere High school, and less than 1 mile from Windermere Prep, convenient SR 429 access, and a short drive to Walt Disney World round out the location.
Listing Agent: Jeffrey Funk, Pa (407-285-9672)
14014 EDEN ISLE BLVD, WINDERMERE, FL 34786
$507,0001 Day on yellowkey MLS ID: O6400224
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1794 Built: 2004Monthly Fee: $93 Tax: $2,957 (2025)Community: Eden Isle 52/9 Lot 173Spa: NoSingle Family
Taxes:$2,957
Elementary School: Keene Crossing Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to your next chapter in one of Windermere’s most desirable gated communities. This beautifully maintained single-story home offers the perfect balance of comfort, functionality, and lifestyle. With 3 bedrooms, 2 bathrooms, and 1,794 sq ft, the layout is thoughtfully designed to feel open, bright, and effortlessly livable from the moment you walk in. Natural light fills the home, enhancing the spacious feel and creating a warm, inviting atmosphere that buyers instantly connect with. Every space flows seamlessly, making daily living and entertaining feel easy and intuitive. Step outside and you’ll discover one of the home’s most valuable features: a private backyard, surrounded by mature trees, offering both privacy and tranquility. Whether it’s morning coffee, family time, or simply unwinding at the end of the day, this outdoor space becomes a true extension of the home. Perfectly positioned, the home sits directly in front of the community playground, creating a unique sense of openness and convenience ideal for families, yet equally appealing for those who enjoy a peaceful, well-maintained environment without rear neighbors disrupting privacy. This home is especially well-suited for: - Buyers starting a family seeking safety, space, and community - Those looking to downsize without compromising comfort or outdoor living - Anyone who values a gated community lifestyle in a prime Windermere location Located just minutes from top-rated schools, shopping, dining, and major access roads, this is where convenience meets quality of life. Homes like this don’t just check boxes, they create a feeling. And this one feels like home. Contact us today for more information or to schedule a private showing! Attention: the home is not being sold furnished. The furniture shown is virtually staged only.
Listing is courtesy of: SELECTA REALTY LLC (407-777-7131)
Listing Agent: Marcella Reginato (407-725-9180)
1002 OAKDALE ST, WINDERMERE, FL 34786
$975,0009 Days on yellowkey MLS ID: TB8495717
1 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 3516 Built: 1973 Tax: $8,799 (2025)Community: Windermere TownSingle Family
Taxes:$8,799
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Set on a prominent corner lot in one of Windermere’s most sought-after enclaves, this thoughtfully updated residence blends timeless character with modern upgrades, enormous walk out bottom level, massive multiple garages and a lifestyle that is uniquely local to this area. Relax on the expansive front porch and take in the surroundings as neighbors and nature pass by. Recent improvements include a new roof, a fully renovated kitchen, a designer-inspired primary bath, fresh interior and exterior paint, and newer engineered wood flooring, creating a cohesive, move-in ready home with a refined, modern feel. The layout offers expansive living spaces filled with natural light, designed for both everyday comfort and effortless entertaining. The primary suite serves as a true retreat, highlighted by a beautifully reimagined bath featuring a freestanding soaking tub, custom tile work, and a double vanity. Additional living areas and a spacious lower level provide flexibility for a media room, home office, fitness space, or guest accommodations. A rare offering in this location, the property features an impressive 3 bay, 30' long garage on one end and an additional garage bay on the opposite end of the home., ideal for collectors, storage, or workshop needs. Positioned along historic Windermere’s signature tree-lined dirt roads, the setting offers a level of charm and privacy that is increasingly hard to find. Residents enjoy exclusive access to city tennis courts and a private dock with entry to the interconnected lake chain that surrounds this community, delivering a true lake lifestyle just moments from home. Seller is offering up to a $25,000 closing cost credit, providing added flexibility and value for buyers. A compelling combination of location, scale, and thoughtful updates—this is Windermere living at its best.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Frank Smith (401-644-4762)
11636 WATER RUN ALY, WINDERMERE, FL 34786
$425,000188 Days on yellowkey MLS ID: S5136888
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1584 Built: 2017Monthly Fee: $332 Tax: $5,634 (2024)Community: Ashlin Park Ph 2Townhouse
Taxes:$5,634
Remarks: This property is a beautifully maintained 3-bedroom, 2.5-bath townhouse located in the desirable Ashlin Park community of Windermere. Built in 2017, this home features an open-concept layout filled with natural light, a modern kitchen with quartz countertops, stainless steel appliances, and espresso cabinetry. The spacious primary suite offers a walk-in closet and an elegant ensuite bath. Enjoy a private interior patio between the main home and the detached two-car garage with epoxy flooring, perfect for relaxing or entertaining. Residents benefit from community amenities including a pool, clubhouse, playground, and walking trails. Conveniently situated near top-rated schools, shopping, dining, and major highways, this property combines modern comfort with an unbeatable location in the heart of Windermere.
Listing Agent: Jose Jimenez (407-394-6379)
12718 WINDERMERE ISLES PL, WINDERMERE, FL 34786
$1,490,0007 Days on yellowkey MLS ID: O6399958
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3487 Built: 1997Monthly Fee: $130 Tax: $6,661 (2025)Community: Isles WindermereSpa: YesSingle Family
Taxes:$6,661
Remarks: Welcome to 12718 Windermere Isles Place, a spectacular residence tucked away on a quiet cul-de-sac in the heart of Windermere. Situated on a sprawling nearly one-acre lot, this beautifully remodeled home offers an exceptional blend of privacy, space, and elegance. Enjoy serene views of the expansive backyard and picturesque koi pond from the spacious shaded patio or the screened rear porch. The outdoor living area is designed for true Florida living, featuring a sparkling pool and spa, perfect for relaxing or entertaining. Adding to the sense of tranquility, one side of the property has no direct neighbors—only beautifully maintained green space and a scenic bridge, creating gorgeous views and a rare feeling of serenity. Inside, the home features generously sized rooms filled with comfort and charm, including an oversized family room with a wood-burning fireplace. The primary suite is a private retreat, complete with a luxurious bath featuring dual sinks, a jetted garden tub, a large walk-in shower, and a full vanity area. Every detail has been thoughtfully updated with style and functionality in mind. Additional highlights include a three-car garage with ample space for parking and storage, as well as a prime location within a top-rated public school district, just minutes from Windermere’s premier shopping, dining, and recreation. A rare opportunity to own a beautifully updated home in one of Central Florida’s most desirable communities.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Patricia Zimath, Llc (321-318-1050)
4226 DOWNEAST LN, WINDERMERE, FL 34786
$10,500,000181 Days on yellowkey MLS ID: O6355233
REDUCED by $1,300,000 (11.0%) on 04/08/2026
Bed: 5 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 5316 Built: 1980 Tax: $10,926 (2024)Community: NaSingle Family
Taxes:$10,926
Middle School: Chain of Lakes Middle
Remarks: DRAMATIC PRICE IMPROVEMENT. Exceptional DEVELOPMENT OPPORTUNITY, currently R-CE zoning should allow for 3 Luxury Home Sites Discover over 5+acres of waterfront land with 300 feet of pristine shoreline on LAKE DOWN, part of the coveted BUTLER CHAIN of Lakes. This is a rare chance to create a premier LAKEFRONT ESTATE or subdivide to create three ideally sized lots with water frontage. At present, the property includes an older 5,000 sq ft home (5 bedrooms, 3.1 baths) and an oversized four car garage, which can serve as a temporary residence or teardown to make way for your vision. Why this property stands out, Unmatched location: Situated on the east side of Windermere, with convenient access from Conroy Windermere Road and Apopka Vineland. Windermere prestige, Offers the cachet of a WINDERMERE ADDRESS and proximity to luxury amenities. Prime access: Minutes to Isleworth Country Club, Bay Hill, and downtown Windermere. Development upside: Ready canvas for luxury estates in one of Central Florida’s most desirable waterfront corridors. Whether you’re a developer, custom builder, or investor, this is your opportunity explore and deliver truly exceptional homes in a highly sought-after market. Property is also listed as vacant land on MLS #O6367852.
Listing is courtesy of: COLDWELL BANKER RESIDENTIAL RE (407-647-1211)
Listing Agent: Thad Czapka (407-257-4253)
6752 TRELLIS VINE LOOP, WINDERMERE, FL 34786
$970,00090 Days on yellowkey MLS ID: O6376318
REDUCED by $30,000 (3.0%) on 04/22/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3820 Built: 2018Monthly Fee: $200 Tax: $10,983 (2024)Community: WindstoneSingle Family
Taxes:$10,983
Remarks: ONLY APPROXIMATELY 7 YEARS NEW, THIS HOME OFFERS MODERN DESIGN AND PEACE OF MIND. MAJOR PRICE DROP - $80,000 OFF! Designed for those who crave space, privacy, and elevated living, this exceptional newer home offers 5 BEDROOMS PLUS TWO BONUS ROOMS, including ALL 4 MAIN BEDROOMS with WALK-IN CLOSETS and a private guest suite featuring an EN-SUITE and WALK-IN CLOSET—all complemented by NO REAR NEIGHBORS and NO FRONT NEIGHBORS, creating extraordinary flexibility for refined living, entertaining, and everyday comfort. Have you ever dreamt of living close to Disney in an upscale neighborhood—where modern luxury meets peaceful surroundings? This is where that dream becomes reality. At the heart of the home, a gourmet kitchen that chefs will love anchors the OPEN-CONCEPT design. A Gas line is available for the stove. flowing effortlessly into the main living areas. Whether hosting celebrations or enjoying quiet evenings at home, the thoughtfully designed layout includes a living room, a family room, and expansive, light-filled spaces designed for connection. One of the large bonus rooms is currently being used as a MOVIE ROOM, offering a private, theater-style retreat ideal for entertaining or cozy nights in. The bedroom layout is equally impressive, offering space and privacy for everyone. ALL 4 MAIN BEDROOMS include WALK-IN CLOSETS, while the guest bedroom’s EN-SUITE and WALK-IN CLOSET create the perfect setup for visitors, multi-generational living, or a luxurious secondary retreat. Step outside to a truly rare outdoor setting—AN OVERSIZED BACKYARD with NO REAR NEIGHBORS and NO FRONT NEIGHBORS, where privacy and tranquility take center stage. This expansive space is ready to become your personal oasis, whether that includes a resort-style pool, outdoor kitchen, or serene garden escape. When the day winds down, retreat to the MASTER SUITE, an impressively spacious sanctuary designed for rest, relaxation, and renewal. Every detail throughout the home reflects thoughtful design, modern elegance, and effortless functionality. Ideally located VERY, VERY CLOSE TO DISNEY and ALL ATTRACTIONS in CENTRAL FLORIDA, this home offers the rare balance of privacy, space, and proximity—placing world-class entertainment, dining, and lifestyle experiences just minutes away. This is more than a home—it’s a lifestyle defined by luxury, location, and possibility.
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Candice Liceaga (407-861-7303)
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