Displaying: For Sale
Location: Windermere
Property Type(s): Single Family
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Windermere - 280 properties found
9725 CHESTNUT RIDGE DR, WINDERMERE, FL 34786
$6,000,000158 Days on yellowkey MLS ID: O6370294
REDUCED by $150,000 (2.4%) on 05/01/2026
Bed: 7 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 8000 Built: 1999Monthly Fee: $1,043 Tax: $29,046 (2024)Community: IsleworthSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$29,046
Elementary School: Windermere Elem
High School: Olympia High
Tax Year: 2024
Middle School: Chain of Lakes Middle
Remarks: Newly renovated, this private Isleworth residence offers a rare balance of architectural authority, thoughtful design, and quiet indulgence. Spanning approximately 8,000 square feet, the home unfolds with intention. Rich walnut cabinetry and wood detailing create warmth and continuity throughout, while the fireplace and wine cellar anchor the living spaces with understated elegance. Every room feels deliberate, refined, and composed. The kitchen is a statement of both form and performance; finished with Taj Mahal quartzite countertops, a 60-inch Wolf gas cooktop, Dacor refrigerator and freezer, two warming drawers, a steam oven, and a discreet hidden pantry designed for seamless entertaining. Dual dishwashers and two laundry areas support effortless daily living behind the scenes. Designed for both privacy and flexibility, the home features six bedrooms, a dedicated office, a bonus room with a closet suitable as an additional bedroom, and an elevator for ease across levels. Bathrooms are equally considered, with five full and 2 half baths, all executed with a calm, modern sensibility. Outdoors, the residence enjoys full privacy and tranquil pond views, complemented by a gas-heated pool and jacuzzi, and summer kitchen; a serene backdrop for both quiet mornings and refined gatherings. Mechanically, the home has been comprehensively updated with four new A/C units (2025), two tankless water heaters, and recently replaced garage doors and motors, ensuring modern efficiency beneath the elegance. It is a residence restored with intention, where discretion, craftsmanship, and comfort converge. Private showings are easily accommodated, including same-day requests. Some photos (4 rooms on the second floor) have been virtually staged.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
9319 WOODBREEZE BLVD, WINDERMERE, FL 34786
$554,555106 Days on yellowkey MLS ID: O6384930
REDUCED by $20,440 (3.6%) on 04/30/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1798 Built: 1986Monthly Fee: $30 Tax: $3,384 (2024)Community: Silver WoodsSingle Family
Taxes:$3,384
Elementary School: None
High School: None
Middle School: None
Remarks: WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you will notice the details: beveled glass front door, split floorplan, large dining and living (open concept) and well-appointed kitchen. The kitchen overlooks the Livingroom and dining room, and boost upgrades you are sure to love. Cherrywood cabinets with pullout shelves, glass doors, pantry, under cabinet lighting, decorative lighting in cabinets, stainless steel appliances and upgraded granite counters. Additional cabinets were added to create workspace or an eat in kitchen space. Just off the kitchen if the laundry area with matching cabinets. The spacious living room is positioned with views of the kitchen and dining space with sliders leading to the massive patio space. Two additional bedrooms are located just off the living room with the hall bath set up for a pool bath if you decided to add one. Just off the dining room you will find the primary bedroom with French doors leading to a private patio space. The primary bath includes a walk in closet space, cherrywood cabinets and a walk in shower. The rear patio has just as many endless options as the front courtyard does...dining spaces or entertaining or both! All this in a home and still just minutes to restaurants, entertainment, shopping, the parks and so much more. Land, Site, and Tax Information
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Steven Looper (321-662-3582)
5036 LATROBE DR, WINDERMERE, FL 34786
$4,900,000249 Days on yellowkey MLS ID: O6346003
1 Days Off yellowkey (back on 3/28/2026)
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 5548 Built: 1990Monthly Fee: $1,224 Tax: $17,326 (2024)Community: IsleworthSpa: NoSingle Family
Taxes:$17,326
Remarks: Under contract-accepting backup offers. Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the property's beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Florida's finest communities.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
8323 LOOKOUT POINTE DR, WINDERMERE, FL 34786
$590,00069 Days on yellowkey MLS ID: O6393407
0 Days Off yellowkey (back on 4/28/2026)
REDUCED by $9,999 (1.7%) on 04/24/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2633 Built: 2016Monthly Fee: $75 Tax: $9,688 (2025)Community: Windermere Trls Ph 3BSingle Family
Taxes:$9,688
Elementary School: Bay Lake Elementary
High School: Windermere High School
Tax Year: 2025
Middle School: Horizon West Middle School
Remarks: Under contract-accepting backup offers. Beautiful 4 bedroom, 3.5 bath home located in the highly sought-after subdivision of Windermere Trails. The first floor has tile flooring and a spacious kitchen equipped with granite countertops, 42'' cabinets, a center island, and a walk-in pantry. Step through the dining room to a beautifully finished courtyard, complete with a private fence and elegant stone pavers. Upstairs, you'll find an additional room with double doors, perfect for a gathering space or home office. The primary bedroom features a large walk-in closet for ample storage. All interior has recently been painted, all carpets upstairs in the main home are new, as well as the AC unit is brand new, ensuring comfort and efficiency. This beautiful home layout provides the opportunity to convert this four bedroom home into six bedrooms. One of the rooms downstairs can easily be converted, as it’s already closed off; you just need to add a closet. Additionally, the loft upstairs is also closed off and simply missing a closet, offering another potential bedroom. This home has a separate private one - bedroom apartment above the garage, featuring a kitchenette, walk in closet, private entrance, and its own washer and dryer with a four month old A/C unit. Conveniently located off Winter Garden Vineland Rd. This home provides easy access to I-4, 429, and is just a short distance from all Disney Theme Parks. Enjoy the benefits of low HOA fees and being close to exceptional A+ schools.
Listing is courtesy of: WEST ORLANDO PROPERTY MANAGEMENT REALTY, LLC (407-922-9169)
Listing Agent: Ricardo Diaz (407-922-6196)
9639 WESTOVER ROBERTS RD, WINDERMERE, FL 34786
$5,900,000274 Days on yellowkey MLS ID: O6341883
REDUCED by $495,000 (7.7%) on 04/28/2026
Bed: 5 Bath: 8.5 Gar: 7 Liv Area Sq Ft: 11861 Built: 2017 Tax: $50,738 (2024)Community: Gotha TownSpa: YesSingle Family
Taxes:$50,738
Elementary School: Thornebrooke Elem
Middle School: Gotha Middle
Remarks: Welcome to a residence that transcends even the highest expectations of luxury living! This is a once-in-a-lifetime estate where architecture, scale, and location combine to create an experience that is as rare as it is breathtaking. From the moment you arrive, the home commands attention with a grand, Mediterranean-inspired façade that opens to interiors of soaring scale and meticulous marble craftsmanship. Light cascades through walls of glass, illuminating a series of living spaces designed for entertaining at the highest level. Every detail speaks of refinement: bespoke millwork, hand-selected stone, intricate ceiling treatments, and custom finishes curated with an uncompromising standard. The expansive chef’s kitchen blends culinary excellence with artful design, while the bar, wine room, and multiple gathering spaces ensure that every occasion, from intimate family dinners to grand celebrations, is unforgettable. The state-of-the-art theater begs you to slow down and enjoy the latest movie release. Conveniently adjacent to the theater is a home gym and lakefront cardio room that rivals most commercial gyms! Once the day winds down, the private retreats within the home offers warmth and convenience so you never have to leave. The first floor conveniently offers a full guest suite, and the second floor boasts an additional four bedrooms all with en-suite bathrooms. Additionally located on the second floor is a kid’s study, playroom, guest apartment and handsome cigar room. Outdoors, the estate transforms into a private resort. A sweeping terrace frames an oversized resort style pool and spa, surrounded by gardens, fountains, and tranquil seating venues. Enjoy the piece of your surroundings, from al fresco dining beneath the pergola to evenings spent overlooking Lake Olivia, one of Central Florida’s most sought-after ski lakes. Beyond the main residence, a detached guest retreat and showcase garages offering space for up to 14 cars will satisfy the most serious car collector. Set on a significant 4.43 acre parcel of land, the estate is both sanctuary and statement, offering numerous spaces to live, create, and entertain. Enjoy living in the heart of it all without compromising your privacy. Plus, with easy access to major highways, theme parks, downtown Windermere, and less than 10 minutes from Whole Foods, Restaurant Row, and championship golf courses, you’re never far from the very best of what Central Florida has to offer. Perfectly positioned with easy access to Windermere Prep, Lake Highland, and Montverde Academy...this location does not get any better! Rarely does a property of this magnitude become available. This is not simply a home — it is an heirloom, a landmark, and an invitation to experience luxury on a level few will ever know. Call today for an exclusive private showing.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
11410 RAPALLO LN, WINDERMERE, FL 34786
$760,000536 Days on yellowkey MLS ID: O6265256
Bed: 6 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3336 Built: 2003Monthly Fee: $130 Tax: $8,434 (2023)Community: Belmere Village G2 48 65Single Family
Taxes:$8,434
Elementary School: Lake Whitney Elem
High School: West Orange High
Tax Year: 2023
Middle School: SunRidge Middle
Remarks: This stunning 6-bedroom Park Square home in Windermere combines elegance and functionality. The first floor features formal living and dining areas, a gourmet kitchen with stainless steel appliances and a gas stove, and a custom-designed patio garden with a water fountain and remote-controlled fans. Upstairs, enjoy luxury vinyl flooring, an oversized master suite with a walk-in closet, and spacious additional bedrooms. Located in the gated Belmere Village, residents benefit from low HOA fees and exceptional amenities, including a clubhouse, fitness center, resort-style pool, playground, basketball, volleyball courts and newly added pickleball courts. Conveniently near major highways and Orlando's theme parks, this home offers the perfect blend of luxury and location. Don't miss this opportunity—schedule a showing today!
Listing is courtesy of: ORLANDO BROTHERS REAL ESTATE LLC (407-925-2221)
Listing Agent: Rebeca Lima (407-800-5654)
17538 BLACK RAIL ST, WINDERMERE, FL 34786
$1,390,000249 Days on yellowkey MLS ID: O6349325
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4522 Built: 2014Monthly Fee: $167 Tax: $16,404 (2024)Community: EnclaveSingle Family
Taxes:$16,404
Remarks: Spacious 6-bedroom, 4-bath Windermere home with dual master suites, pond views, and a fenced yard. Built in 2014, this residence features an open layout with a gourmet kitchen, granite counters, stainless steel appliances, and 42” cabinets. Upstairs includes a loft/media room and generously sized bedrooms. Enjoy serene water views, a private backyard, and a 3-car garage. Located in a desirable community with easy access to schools, shopping, and major highways.
Listing is courtesy of: GARCIA REALTY GROUP (407-920-3616)
Listing Agent: Elaine Garcia (407-920-3616)
9259 TIBET POINTE CIR, WINDERMERE, FL 34786
$6,499,000378 Days on yellowkey MLS ID: O6312645
2 Days Off yellowkey (back on 4/26/2026)
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 6257 Built: 2007Monthly Fee: $298 Tax: $35,727 (2024)Community: Keenes PointeSpa: NoSingle Family
Taxes:$35,727
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. Welcome to 9259 Tibet Pointe Circle, an extraordinary lakefront residence nestled within the highly sought after guard-gated community of Keene’s Pointe. Completely renovated in 2025, this exquisite home combines timeless elegance with modern luxury, offering breathtaking views and direct frontage on the pristine waters of Lake Tibet. This meticulously updated estate showcases high-end finishes throughout, with no detail overlooked. Enjoy a brand-new gourmet kitchen equipped with top-of-the-line appliances, custom cabinetry, and designer fixtures. The open-concept layout flows seamlessly into spacious living and dining areas, perfect for entertaining or relaxing while taking in panoramic lake views. The home’s thoughtfully reimagined floor plan features luxurious bedrooms, spa-inspired bathrooms, and refined touches such as wide-plank hardwood flooring, quartz countertops, and designer lighting. Expansive windows and glass doors fill the home with natural light and lead to a private outdoor retreat with fireplace and summer kitchen - ideal for enjoying Central Florida sunrises over the water. Additional improvements include hardwood and porcelain flooring, tankless gas water heater, updated AC units (2), water softener, new pool heater, and much more. A 4-car garage completes this amazing property. Located in the heart of Windermere, Keene’s Pointe offers world-class amenities including the renowned Golden Bear Club with golf, tennis, fitness, swimming and dining. Don’t miss this rare opportunity to own a move-in ready, lakefront masterpiece on the Butler Chain of Lakes. Schedule your private tour today and experience luxury lakefront living at its finest.
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
14255 SONCO AVE, WINDERMERE, FL 34786
$849,90080 Days on yellowkey MLS ID: O6392262
REDUCED by $25,000 (2.9%) on 04/25/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2698 Built: 2006Monthly Fee: $130 Tax: $11,194 (2025)Community: SummerportSpa: YesSingle Family
Taxes:$11,194
Elementary School: Keene Crossing Elementary
Remarks: Super Rare Opportunity! Tucked away in one of Windermere’s most desirable areas is the beautiful home on over 1 half acre homesite on a corner lot with no rear neighbors and a gorgeous lake view. Don't sleep 'on' this home if you want to sleep 'in' this home! New roof 2023. Interior features include a fully remodeled kitchen with white 42" cabinets with crown moulding and gold hardware, custom vent hood with a tile backsplash. In addition a huge quartz centerpiece island with upgraded stainless steel appliances including a gas range plus a farmhouse sink. All overlooking the huge family room, 3 gold pendant lights and gold chandelier. New vinyl plank flooring throughout the entire first floor plus the stairs and loft on the 2nd floor. Spacious master suite with double sink vanity with garden tub and separate shower. 2 walk in closets as well. Formal living room, independent den/office with storage closet, half bath with custom vessel sink and indoor laundry room round out the first floor. Upstairs you will find the aforementioned loft along with 3 additional bedrooms and full bath with updated floor to ceiling tile and glass door shower. As you walk out onto the covered patio, along with the tremendous screen enclosed pool and spa you will find plenty of green grass to run and play in the fully fenced yard and if you need even more, utilize the greenspace to the side of the home as well. Enjoy the tranquil views of the serene lake from the back or relax on the extended covered front porch on a rocker from Cracker Barrel and if your in the mood for some ice cream or coffee, just a 5 minute walk from the front door is Kelly's Ice Cream and Foxtail coffee and even a pizza shop, and on your way you will pace by the "A" rated Keene Crossing Elementary school. .Additional community amenities include clubhouse with pool, tennis and basketball courts, sand volleyball and a private pier. Location benefits include easy access to Horizon West Town Center and all the monthly activities, Windermere Prep, Foundation Academy private schools, numerous restaurants and shopping, SR 429, Florida Turnpike and so much more!
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Carmen Aridas (407-299-6942)
6149 GROSVENOR SHORE DR, WINDERMERE, FL 34786
$10,900,000211 Days on yellowkey MLS ID: O6356355
Bed: 6 Bath: 7.0 Gar: 7 Liv Area Sq Ft: 6783 Built: 2013Monthly Fee: $298 Tax: $57,807 (2023)Community: Keenes PointeSpa: YesSingle Family
Taxes:$57,807
Remarks: Keene's Pointe - Stunning lakefront home on Lake Tibet of the famed Butler Chain of Lakes. No detail was spared in this completely renovated home boasting formal living and dining rooms, family and media room, 2 offices, 6 full/2 half baths and 6 bedrooms - one of which could serve as a in-law suite with separate entrance from the outside. From the moment you enter this impeccably designed home ALL ON ONE FLOOR, you are greeted with style and elegance. Featuring built in cabinets, shelving, and wall panels, powered blinds and drapes, lighting controls, designer features and modern decor. The formal living and piano room spotlights a lighted onyx wall and two-sided gas fireplace opening up to the family room and formal dining which leads to the kitchen and media room. The primary suite with two spacious closets and spa-like bath is located privately away from the secondary bedrooms. The house was designed to maximize views of the lake and access to the enclosed lanai which has a sitting room with fireplace, dining area, half bath and kitchen with grill, sink, ice maker and refrigeration. This home has 7 garages, a 4-car garage with EV charging station and air conditioning adjoins the house and a separate 3-car garage on the opposite side of the courtyard which could also be renovated into a separate guest house if needed. There is plenty of deck space around the pool and spa for entertaining and the spacious back yard leads the way to the covered boat dock with boat and jet ski lifts. Located in Windermere, Florida, with top-rated public and private schools, shopping, dining, close to tourist attractions and expressways. This home is your dream come true!
7137 BEEK ST, WINDERMERE, FL 34786
$550,00054 Days on yellowkey MLS ID: O6398814
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1910 Built: 2013Monthly Fee: $120 Tax: $7,932 (2025)Community: Windermere TerraceSingle Family
Taxes:$7,932
Elementary School: Sunset Park Elem
Remarks: Under contract-accepting backup offers. BUYER FAILED TO DEPOSIT ESCROW - BACK ON MARKET - Welcome to Windermere Terrace. This home offers a rare combination of privacy, location, and lifestyle that is difficult to find in Central Florida. Set on a premium lot, the property overlooks a pond with a conservation area beyond that means you will never have rear neighbors! This buffer creates a peaceful and private setting that enhances everyday living. This well-designed home features 3 bedrooms, 2 bathrooms, and approximately 1,910 square feet of living space. The kitchen is both functional and stylish and includes 42-inch cabinets, granite countertops, stainless steel appliances, pendant lighting, and ample pantry storage. The split-bedroom floor plan offers privacy and flexibility. The primary suite features dual vanities, a walk-in shower, and a spacious closet. Meanwhile, the secondary bedrooms and full bathroom are positioned on the opposite side, making them ideal for guests or family members. Step outside to a screened patio that extends your living space. Here, you can relax while enjoying tranquil water and conservation views. Residents of Windermere Terrace enjoy community amenities that include a pool and scenic walking paths. Perfect location too with convenient access to shopping and dining at Winter Garden Village, as well as outdoor recreation at Tibet-Butler Nature Preserve. Major roadways are also easily accessible, simplifying your daily commute. This home delivers a rare blend of privacy, views, and proximity to Central Florida’s top attractions, including Universal Orlando Resort and SeaWorld Orlando. Schedule your private showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Jacquie Sosa (407-340-9793)
6956 TRELLIS VINE LOOP, WINDERMERE, FL 34786
$650,00048 Days on yellowkey MLS ID: O6401639
0 Days Off yellowkey (back on 4/22/2026)
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3015 Built: 2019Monthly Fee: $161 Tax: $10,719 (2025)Community: WindstoneSingle Family
Taxes:$10,719
Remarks: This is a gorgeous two-story home with five bedrooms, four baths, and a two-car garage. This home offers an open floor plan with an expansive great room featuring an elegant display of windows to create a naturally luminous home, casual dining area, and kitchen. The casual dining area allows outdoor access to a lanai and the kitchen provides plenty of counter space as well as an oversized island and a walk-in pantry. The first floor also includes a den with coffered ceilings, second bedroom, and a laundry room. The second floor includes a master suite with coffered ceilings, a master bath with large shower and walk-in closet, and three bedrooms and two baths. Windstone is a new community conveniently located in highly desirable Windermere, near the popular Butler Chain of Lakes. The community is perfectly situated to provide convenient access to the high-end retail and dining amenities of the Windermere area and is just minutes away from all of Central Florida's major theme parks, sports, and cultural opportunities.
Listing is courtesy of: EAST PEARL REALTY (407-802-6859)
Listing Agent: Dan Li (407-808-1859)
9713 ENDICOTT CT, WINDERMERE, FL 34786
$5,250,00053 Days on yellowkey MLS ID: O6393891
1 Days Off yellowkey (back on 4/21/2026)
Bed: 6 Bath: 7.0 Gar: 6 Liv Area Sq Ft: 7818 Built: 2007Monthly Fee: $313 Tax: $66,793 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$66,793
Remarks: Experience elevated lakefront living in this beautifully updated estate, within the prestigious guard gated golf community of Keene’s Pointe, offering direct access to the Butler Chain of Lakes. With over $850,000 in upgrades, this home is perfectly positioned to capture breathtaking sunset views and nightly Disney fireworks from the primary suite. This home delivers a rare combination of privacy, luxury, and lifestyle. Thoughtfully designed for both everyday living and effortless entertaining, the residence features water views from multiple living spaces, a layout that balances open gathering areas with private retreats, and dedicated spaces for both relaxation and recreation. The primary suite is a true retreat, featuring a private balcony overlooking the tranquil backyard and lake. A dedicated lounge with a beverage bar, updated spa-inspired bathroom, and custom walk-in closet create a refined and relaxing escape. Every bedroom is an ensuite, providing exceptional comfort for family and guests, while two fully remodeled junior suites showcase modern bathrooms and expanded custom closets. On the main level, enjoy formal dining complemented by a wine cellar, while a double-sided gas fireplace connect the family and game rooms which adds warmth and ambiance. The spacious game room and media room ensure there is always something to enjoy indoors. Step outside to your private oasis, where a resort-style pool and spa, fully equipped outdoor kitchen, covered dining area, and outdoor fireplace set the stage for year-round enjoyment. Retractable screens provide shade and comfort during the summer months, while the updated dock and boat lift make lake access effortless. A private canal connects you to Lake Tibet and the greater Butler Chain, offering the best of true lakefront living. For extended stays or multi-generational living, the apartment above the detached garage offers a private, fully functional space complete with a kitchenette, full bath, walk-in closet, and laundry. Positioned on a quiet cul-de-sac, this estate offers enhanced privacy along with an expansive driveway and turnaround for effortless arrivals and guest parking. The impressive five-car garage, along with a dedicated golf cart garage, provides exceptional space for collectors, storage, and embracing the Keene’s Pointe golf lifestyle. This is more than a home—it’s a complete lifestyle experience. From lake days and sunset views to golf, dining, and the best of Central Florida just minutes away, this property delivers the elevated living today’s luxury buyer expects.
Listing Agent: Amy Moline (407-506-7447)
6799 HELMSLEY CIR, WINDERMERE, FL 34786
$658,000204 Days on yellowkey MLS ID: O6361417
3 Days Off yellowkey (back on 4/20/2026)
REDUCED by $12,000 (1.8%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2615 Built: 2011Monthly Fee: $129 Tax: $9,339 (2024)Community: Preston SquareSingle Family
Taxes:$9,339
Remarks: Windermere Lake View Home with Disney Fireworks - Best Value in the Area! Recent price improvement - now one of the best opportunities in Windermere. Welcome to your dream home! This beautiful 4-bedroom, 3.5-bathroom residence offers the perfect blend of elegance, comfort, and convenience — ideally located in one of Windermere’s most sought-after communities with top-rated “A” schools. Enjoy breathtaking views of the lake and conservation area right from your spacious covered screened lanai, with a large backyard ready for your future pool. The open-concept kitchen flows seamlessly into the living and dining areas, creating an inviting space for family gatherings and entertainment. On the first floor, you’ll find a guest suite with a full bath, a private office, and a welcoming foyer. Upstairs features a massive loft — perfect as a media room, playroom, or second family room — along with the master suite and two additional bedrooms. The home also features a newer air conditioning system replaced just two years ago, offering added comfort and peace of mind. Enjoy the exclusive community amenities, including a clubhouse, pool, playground, and sports court. From your backyard, you can even watch the Disney fireworks at night! Conveniently located near shopping centers, dining, and entertainment, this home truly combines luxury, location, and lifestyle — the perfect place for your family in Windermere! Seller willing to consider offers.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Maqueli Gewehr (863-258-5656)
13622 DARCHANCE RD, WINDERMERE, FL 34786
$629,90080 Days on yellowkey MLS ID: S5146266
REDUCED by $19,100 (2.9%) on 04/20/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2147 Built: 2007Monthly Fee: $81 Tax: $5,403 (2025)Community: Enclave/Berkshire Park B G H ISingle Family
Taxes:$5,403
Remarks: Welcome home to Berkshire Park. This 3bedroom, 2bath residence offers a balance of comfort and convenience in a quiet residential setting. Ideally located just minutes from world-class attractions including Walt Disney World, as well as shopping, dining, and major highways, this property places you at the center of Central Florida living. The community is surrounded by nearby schools, adding everyday practicality for families. Whether you’re searching for a primary residence, vacation home, or investment opportunity, this home delivers strong value through location, accessibility, and long-term growth potential. Schedule your private tour today.
Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)
Listing Agent: Javin Lopez (407-873-6606)
918 ALGARE LOOP, WINDERMERE, FL 34786
$585,00063 Days on yellowkey MLS ID: O6396400
5 Days Off yellowkey (back on 4/18/2026)
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2553 Built: 2002Monthly Fee: $138 Tax: $4,190 (2025)Community: Belmere Village G3 48 70Single Family
Taxes:$4,190
Remarks: Under contract-accepting backup offers. Short Sale. Short sale opportunity in gated Belmere of Windermere. Situated on a large corner lot, this home features a split-bedroom floor plan, formal living and dining rooms, private office, and open kitchen overlooking the family room with fireplace. Additional highlights include wood-look flooring, high ceilings, abundant natural light, spacious primary suite with walk-in closet and large bath, covered and screened porch, tile roof, solar system, central vacuum, and side-entry 3-car garage. Great opportunity to own below market value in a community with excellent amenities. Short sale subject to lender approval.***Sellers will make the decision by Sunday 04/12/26. Please be advised that we have multiple offers.****
Listing is courtesy of: SOUTHERN PRESTIGE REALTY INC (407-614-3873)
Listing Agent: Abdul Aitboukil (863-521-2067)
5926 BLAKEFORD DR, WINDERMERE, FL 34786
$2,149,00094 Days on yellowkey MLS ID: O6388716
1 Days Off yellowkey (back on 4/17/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3906 Built: 1999Monthly Fee: $298 Tax: $12,674 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$12,674
Remarks: Keene's Pointe - 24 hour gated/attended golf community in Windermere, Florida. This fully renovated home is situated on one of the most beautiful lots in the community. Located on the 11th fairway of The Golden Bear Club with golf and pond views, as well as golf and pond views of the 12th green from the front porch. Boasting an open floor plan with a dining room large enough to hold a table of 12, 3 bedrooms downstairs including the primary. The kitchen is functional with an island seating 4 with quartz waterfall edges, coffee bar, stainless KitchenAid appliances, Dacor panel refrigerator and pantry. The great room has a wall of windows overlooking the patio and stone fireplace. There is also a spacious office with desk and built-ins, and a second office/bar with built-ins that can be easily converted to a 5th bedroom. The primary suite is spacious with a wall of windows overlooking the pond/golf course, bathroom with 2 vanities with lighted mirrors, free-standing tub, and shower with rain head and 6 body jets, and large walk-in closet. The second floor features the 4th bedroom, perfect as an in-law suite, media or game room with 2 walk-in closets and a bath with shower and tub. Enjoy the view from the large covered patio with stone fireplace and summer kitchen overlooking the updated screened salt water pool and spa (new pump and heater in 2025), as well as the expansive and private back yard. The side entry garage features two parking spaces and an additional golf cart parking area, as well as epoxy coated floor and built-in cabinets and overhead racks. There is also steps to the attic over the garage with wood flooring for extra storage. Everything in this home has been tastefully updated in 2025. Wood-look tile and plantation shutters throughout, elegant lighting, tankless gas water heater (2025), pavered driveway and porch, new roof in 2021, AC's (2025/2018). This home has everything that country club living has to offer. Conveniently located to shopping, dining, expressways, tourist attractions and top-rated public and private schools. Call for your private showing today.
4812 ALEXANDRA GARDEN CT, WINDERMERE, FL 34786
$3,699,000279 Days on yellowkey MLS ID: O6339134
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4262 Built: 2007Monthly Fee: $1,146 Tax: $45,888 (2024)Community: IsleworthSpa: YesSingle Family
Taxes:$45,888
Remarks: Luxury villa living within the exclusive Gardens of Isleworth, part of the Isleworth Golf & Country Club. This exceptional Southpoint built residence boasts a captivating courtyard floor plan that provides breathtaking views from every corner of the home. The rear of the residence presents serene views of a picturesque pond and the tranquil Isleworth Gardens, while interior windows reveal a private courtyard featuring a glistening pool adorned with a cascading waterfall from the pergola. An expansive covered patio houses a summer kitchen, pool bath, and attached third bedroom accessed only from the courtyard. The heart of this home is a chef's dream, with a gourmet kitchen featuring top-of-the-line Wolf appliances, striking custom cabinetry, and an open design that seamlessly connects to the family room and dining areas. The grand primary suite offers a private sitting area overlooking the peaceful pond, double walk-in closets, and a spa-like bath complete with a Jacuzzi tub and an expansive walk-in shower. The third garage was converted into a gym with air conditioning and can be converted back to additional garage space. Garden villas offer carefree living with exterior grounds maintenance included in the separate monthly fees. The 600-acre Isleworth community, surrounding the Butler Chain of Lakes, is a residential enclave that sets the standard of excellence for Central Florida living. Isleworth Golf & Country Club, which is located within the community, is recognized as one of the Top 100 Platinum Clubs of the World offering separate membership opportunities that provide access to golf, tennis, fitness, Clubhouse dining and social events, swimming in the resort-style pool and sundeck, dock, and an abundance of activities. Enjoy a lifestyle defined by casual elegance in a setting that sets the standard for luxury living.
Listing Agent: Rob Rahter (407-497-4526)
12488 PARK AVE, WINDERMERE, FL 34786
$15,500,00055 Days on yellowkey MLS ID: O6395291
Bed: 10 Bath: 14.5 Gar: 9 Liv Area Sq Ft: 13425 Built: 1996Monthly Fee: $633 Tax: $56,672 (2025)Community: Chaine Du LacSpa: YesSingle Family
Taxes:$56,672
Remarks: Commanding a rare 2.75-acre lakefront setting on the coveted Butler Chain of Lakes, this extraordinary Windermere estate is a true work of art. Recently completed after a meticulous, ground-up transformation, the residence showcases a level of craftsmanship, design integrity, and finish quality that is simply unrivaled in Central Florida. From the moment you arrive, the estate announces itself with undeniable presence. Grand entry doors open to a breathtaking interior defined by soaring 30-foot ceilings, dramatic architectural volumes, and a sleek, contemporary aesthetic softened by warm, bespoke materials. Walls of glass frame panoramic lake views, creating a seamless dialogue between indoor elegance and the natural beauty beyond. Designed for both refined living and grand-scale entertaining, the interior amenities rival those of a world-class resort. Highlights include a private spa sanctuary, fully equipped fitness center, state-of-the-art home theater, and an expansive game and entertainment lounge. The chef’s kitchen is a showpiece, thoughtfully designed for culinary excellence, intimate gatherings, or catered events, anchored by Wolf & Miele appliances, custom cabinetry, and flawless detailing throughout. The primary suite is nothing short of spectacular: a serene retreat offering commanding lake views, spa-inspired bath accommodations, and an atmosphere of complete privacy and indulgence. Every element of the home is enhanced by cutting-edge smart home technology, delivering effortless control, comfort, and security. A thoughtfully designed separate guest wing allows for exceptional flexibility, making the estate equally suited as a private family residence, an entertainer’s dream, or an inspired corporate retreat. Outdoors, the property unfolds into a private resort oasis. Impeccably manicured grounds lead to a private boat dock on the Butler Chain, a hidden garden retreat, and a stunning resort-style pool ideal for both relaxation and large-scale gatherings. Additional features include a putting green, a nine-car garage, and a detached guest house complete with its own kitchen, living area, and bedroom, perfect for extended guests or staff accommodations. A rare opportunity to own one of Central Florida’s most iconic and impressive lakefront compounds, where every detail has been elevated to the highest standard.
Listing is courtesy of: ONE LUXURY INTERNATIONAL LLC (407-312-8003)
Listing Agent: Julie Christensen (407-592-2055)
11162 LEDGEMENT LN, WINDERMERE, FL 34786
$995,000237 Days on yellowkey MLS ID: O6346461
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3248 Built: 2002Monthly Fee: $170 Tax: $7,747 (2024)Community: Glenmuir Ut 02 51 42Single Family
Taxes:$7,747
Remarks: NEW TILE ROOF INSTALLED BEFORE CLOSING! Welcome to Glenmuir—one of Windermere’s most sought-after gated communities. This 4 bedroom, 3 full bath, plus 2 half bath home includes a dedicated office and an upstairs bonus room within a primarily single-story layout—a thoughtful blend of functionality and comfort. Double doors open to a bright foyer with immediate views of the custom 2021 saltwater pool and serene greenspace—no rear neighbors. A private office with French doors and a closet sits just off the foyer. The formal living and dining rooms open directly to the covered lanai and pool, offering seamless indoor–outdoor living. The kitchen provides abundant cabinetry, extensive counter space, a butler’s pantry, and a café area overlooking the pool and outdoor spaces. The kitchen and dining nook flow into a spacious family room—an ideal gathering place. The family room provides lots of windows for natural light. The primary suite is a true retreat with direct pool access and a spa-style bath featuring dual vanities, a soaking tub, a walk-in shower, and an oversized walk-in closet. On the opposite wing, three secondary bedrooms and two full baths— including one en suite—offer excellent flexibility for family or guests. Upstairs, a large bonus room with a half bath functions beautifully as a game room, media space, lounge, or studio. Outdoor living shines with the 2021 custom saltwater pool and generous patio space to enjoy evening views of the Disney fireworks. A dedicated exterior half bath for pool access adds convenient hospitality. The fully fenced yard offers privacy and ample room for pets, gardening, or play. A three-car garage and extended driveway provide generous parking. A new tile roof will be installed prior to closing. Recent updates include two new A/C units (Nov 2024), a new water heater (2025), a new irrigation timer and well pump, fresh exterior paint, and a newly painted garage floor. Glenmuir offers a park, playground, basketball court, and picnic pavilion. Zoned for Windermere Elementary, Bridgewater Middle, and Windermere High, and convenient to Windermere Prep. Prime location near the Lake Butler public boat ramp (Butler Chain of Lakes), SR-429, the Florida Turnpike, and nearby shopping, dining, and world-class attractions including Disney, Universal, and SeaWorld. Schedule your private tour today!
Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)
Listing Agent: Deb Schroeder (407-234-2256)
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