Location: Windermere , 34786
Do Not Show Listings
8375 BOWDEN WAY, WINDERMERE, FL 34786
$1,369,000184 Days on yellowkey MLS ID: S5137385
1 Days Off yellowkey (back on 4/4/2026)
REDUCED by $1,000 (0.1%) on 03/31/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3809 Built: 1999Monthly Fee: $283 Tax: $9,709 (2025)Community: Keenes Pointe Unit 1Single Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$9,709
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: The kitchen has been recently upgraded with brand-new white quartz (Calacatta Belardo) countertops and backsplash, creating a bright, modern, and spacious feel. This charming four-bedroom, three-and-a-half-bath home in the highly sought-after Keene’s Pointe community perfectly combines elegance, comfort, and character. Designed with a timeless French-inspired décor, every space feels warm, inviting, and beautifully curated. The highlight of this home is its backyard oasis — a peaceful retreat overlooking the sparkling pool and tranquil pond views, creating the perfect setting for relaxation and entertainment. A nice added air-conditioned covered patio area allows you to enjoy the outdoors year-round, even on the warmest Florida days. Inside, you’ll find beautifully appointed living spaces, elegant finishes, and a floor plan designed for both comfort and functionality — ideal for families or those who love to host. Recent Updates Include: A/C Unit: 2025,A/C Unit: 2016,Roof: 2018,Pool Heater: 2020, Irrigation Well: 2022 Water Heater: 1999 Life in Keene’s Pointe is truly exceptional. Residents enjoy a gated, golf-course lifestyle surrounded by nature, scenic lakes, and the renowned Golden Bear Club, designed by Jack Nicklaus. This exclusive Windermere community offers an active, social, and family-friendly atmosphere unlike anywhere else. Don’t miss the opportunity to make this stunning French-style home your own — a perfect blend of elegance, comfort, and Florida charm.
Listing is courtesy of: B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE (407-217-7573)
Listing Agent: Oscar Rodriguez (321-297-7264)
3138 SEIGNEURY DR, WINDERMERE, FL 34786
$1,350,00050 Days on yellowkey MLS ID: O6387397
0 Days Off yellowkey (back on 4/4/2026)
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3831 Built: 1997Monthly Fee: $250 Tax: $11,794 (2024)Community: Harbor IsleSingle Family
Taxes:$11,794
Elementary School: Thornebrooke Elem
High School: Olympia High
Tax Year: 2024
Middle School: Gotha Middle
Remarks: Under contract-accepting backup offers. Timeless style and classic design unfold behind the gates of Harbor Isle, one of Windermere’s most sought-after communities. This custom-built estate residence offers captivating views of Lake Down on the pristine Butler Chain of Lakes. Featuring all living areas on the first floor except for a bonus room upstairs, this thoughtfully crafted home offers separate formal and living spaces and a private den. The generously-sized primary retreat has a gas fireplace and large bath including oversized shower. Clerestory windows bathe the home in an abundance of natural sunlight. Three secondary bedrooms on the first floor include a guest room with pool bath and a pocket door feature to create a private suite. The additional bedrooms on the first floor are joined by a jack-and-jill-style bathroom. A multi-use space on the second floor is mammoth in size and is a perfect retreat for working from home, game room, or playroom. With an adjacent full bath, the space is large enough to be converted into two additional bedrooms. The screen enclosed pool and spa with patio offers a tranquil escape with lake views in the distance. 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.
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Rob Rahter (407-497-4526)
14217 BRIDGEWATER CROSSINGS BLVD, WINDERMERE, FL 34786
$600,00026 Days on yellowkey MLS ID: O6396155
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2419 Built: 2006Monthly Fee: $131 Tax: $8,205 (2026)Community: SummerportSingle Family
Taxes:$8,205
Elementary School: None
High School: None
Tax Year: 2026
Middle School: None
Remarks: Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consists of the Kitchen, dining, family room, living room, the Master bedroom and the 3 other bedrooms and the guest bathroom. The second floor consists of the large loft, closets and a full bathroom. Don’t miss your chance to experience exceptional living very close to Keenes Crossing Elementary, Bridgewater Middle and Windermere high
Listing is courtesy of: WEICHERT REALTORS HALLMARK PRO (407-585-0500)
Listing Agent: Azim Manji (407-342-3548)
9323 GLADYS GARDEN CT, WINDERMERE, FL 34786
$12,500,00075 Days on yellowkey MLS ID: O6381880
REDUCED by $1,495,000 (10.7%) on 04/03/2026
Bed: 6 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 9770 Built: 2026Monthly Fee: $1,099 Tax: $21,279 (2025)Community: IsleworthSingle Family
Taxes:$21,279
Middle School: Chain of Lakes Middle
Remarks: Brand new construction and fully furnished! Architecturally refined and intentionally designed by Ashley Martin Home, this custom estate is a masterclass in proportion, craftsmanship, and quiet luxury. European-inspired stonework, dramatic gabled rooflines, and a custom metal arched front door set a tone of understated elegance from the moment of arrival. Concrete tile roofing, four-car garage plus golf cart garage, and a friends-and-family entry with covered parking. Inside, discover Sierra Pacific casement windows with stained interior mullions flood the home with natural light, highlighting warm beams, wide-plank floors, and curated details. Lutron lighting, Sonos audio, and powered draperies enhance modern comfort without compromising design. The formal dining room features a stained white oak arched opening, classic dentil molding, and built-in wine display. The living room is anchored by a gas Isokern fireplace with precast surround, custom built-ins, stained beams, and sculptural custom one off lighting, while an interior glass breezeway subtly defines the transition to the private primary wing. The primary suite offers a serene retreat with custom arch detailing, a nickel joint ceiling, and stained beams. The spa-inspired bath includes a marble soaking tub and a dramatic solid limestone staircase leading to a hidden upper-level flex space, ideal for an office or gym, complete with beverage refrigeration and powered Roman shade. The boutique-style closet features dual islands and an integrated wash tower. At the heart of the home, the chef’s kitchen stuns with soaring 18-foot ceilings, exposed beams, a curved reeded island, and custom Urban Electric pendants designed specifically for the residence. Sub-Zero refrigeration, freezer, and wine column, a 60-inch Wolf range, dual integrated dishwashers, and a fully equipped back kitchen ensure effortless entertaining. Indoor and outdoor living connect seamlessly to a private courtyard-style retreat featuring a resort-inspired pool with copper scupper water features, a summer kitchen with Wolf grill, powered screens, and multiple lounging areas designed for year-round enjoyment. Additional highlights include four upstairs en-suite bedrooms, including a secondary primary suite, an upstairs laundry with linen towers and folding station, a third-level bonus floor with theater, bar, powder bath, and storage, elevator-ready construction, and an advanced security system with AI-enabled cameras and window vibration sensors. Designed with architectural intention, this home pairs refined craftsmanship with warmth, creating spaces that feel both elevated and deeply livable.
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Steve Healy (407-230-1441)
5130 SUN PALM DR, WINDERMERE, FL 34786
$525,00027 Days on yellowkey MLS ID: O6390875
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1723 Built: 1987Monthly Fee: $30 Tax: $8,032 (2025)Community: Silver Woods Ph 04Single Family
Taxes:$8,032
Remarks: Welcome to 5130 Sun Palm Drive, located in the heart of WINDERMERE! This beautifully maintained 3-bedroom, 2-bath home offers 1,723 sqft of living space on a spacious ¼-acre FULLY FENCED lot — perfect for outdoor enjoyment and privacy. Recent upgrades include a new ROOF (2022) and a new AC SYSTEM (2020). ALL FLOORING HAS BEEN UPDATED. The carpet was removed and replaced with Mohawk Pergo luxury vinyl plank. The original tile was replaced with fresh ceramic tile throughout the rest of the house—NO MORE POPCORN CEILING, all was removed, and now it has a beautiful finished ceiling. A brand NEW SLIDING GLASS DOOR opens to the NEW PATIO DECK recently installed. Ideal for indoor-outdoor living. Just minutes from the famous Sand Lake Restaurant Row, conveniently located near the distinguished Bay Hill Golf Community, and backing up to the exclusive Isleworth Court private community. Zoned for top-rated schools, and ideally situated just 20 MINUTES from Walt Disney World and 10 minutes from Universal Studios — this location truly offers the best of Central Florida living!
Listing is courtesy of: JASON MITCHELL REAL ESTATE FLO (754-307-0607)
Listing Agent: Elle Walters (407-431-4600)
6712 THORNHILL CIR, WINDERMERE, FL 34786
$680,000198 Days on yellowkey MLS ID: O6351284
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2976 Built: 2002Monthly Fee: $80 Tax: $4,096 (2024)Community: Lakes Windermere Ph 01 49 108Single Family
Taxes:$4,096
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: With timeless curb appeal and a front porch built for slow mornings, this Windermere home blends classic charm with the upgrades that make everyday life easier. Step inside and the ceilings rise, sunlight floods through, and hardwood floors (2021) lead you through open living and dining spaces that flow seamlessly into a remodeled kitchen with quartz countertops, updated cabinetry, and dual pantries that actually hold it all. The primary suite sits privately on the main floor with with a large walk in closet, and ensuite, while three additional bedrooms offer room to spread out — perfect for guests, a home office, or both. The main-level guest bath keeps accessibility in mind with a sleek zero-entry shower, while a nearby half bath makes life easier for everyday traffic. Upstairs, a full suite with its own bath creates the ideal spot for visitors, multi-generational living, or a tucked-away retreat when you need a breather. Covered porches in both the front and back extend your living outdoors, while a rear-entry two-car garage keeps the curb appeal clean. Inside the garage, a wheelchair ramp provides easy access from the garage — and can be removed by the seller if not needed. Major updates are already handled: newer roof (2021), water heater (2018), and one of two HVACs replaced in 2021. Low HOA dues get you high-return perks — a resort-style pool, lake pier for fishing and star-gazing, tennis, volleyball, basketball, playgrounds, and open green space for everything else. All of it just minutes from Windermere’s shops, dining, and top-rated schools. High ceilings, natural light, updates for modern comfort — this is the Windermere vibe, done right.
Listing is courtesy of: HOMEVEST REALTY (407-897-5400)
Listing Agent: Brad Young (407-897-5400)
8180 BOAT HOOK LOOP #108/301, WINDERMERE, FL 34786
$325,000104 Days on yellowkey MLS ID: TB8465266
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1442 Built: 2006 Tax: $4,422 (2024)Community: Lakeside/Lks/Windermere Ph 3Condo
Taxes:$4,422
Remarks: Discover the best of Windermere living in this meticulously maintained 3-bedroom, 2-bath CORNER UNIT condo in Lakeside at Lakes of Windermere. An expansive wrap-around screened porch embraces tranquil views and Florida breezes while providing an ideal space for morning coffee or evening relaxation. Inside, the open-concept layout features silestone countertops, cherry cabinets, and stainless appliances (2023 microwave, and upgraded dishwasher) lending a modern flair to the chef’s kitchen. Additional recent upgrades include a **2024 Carrier 15 SEER HVAC system** for comfort and energy efficiency throughout the year and **BRAND NEW 2025 new wood look porcelain tile** in all three bedrooms (NO CARPET). The generous primary suite and two additional bedrooms are thoughtfully separated for privacy. This floor plan features the closet OUTSIDE of the bathroom in the primary bedroom. Located just steps from the clubhouse and pool, this unit offers easy access to community amenities. Lakeside at Lakes of Windermere residents enjoy a fitness center, clubhouse and resort-style pool. The neighborhood is nestled near Lake Burden with access to a shared private dock and its own man-made lake. As a gated community, it also features a billiards room, walking paths around a central pond, and sports courts and fields. This home is just a few minutes drive from Walt Disney World (and neighboring parks) and boasts a view of the Disney fireworks EVERY night!! The combination of a well-appointed interior, wrap-around porch and enviable location near neighborhood amenities and Orlando's best entertainment make this corner-unit condo an exceptional opportunity.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Erin Aaron (727-422-1688)
11450 ARBORSIDE BEND WAY, WINDERMERE, FL 34786
$749,901189 Days on yellowkey MLS ID: O6354816
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2622 Built: 2002Monthly Fee: $170 Tax: $4,856 (2024)Community: Glenmuir 48 39Single Family
Taxes:$4,856
Remarks: Beautifully maintained 4BR/3BA pool home in gated Glenmuir, Windermere. Open floor plan with high ceilings, formal dining, and spacious family room. Kitchen with breakfast nook overlooks screened pool/lanai. Primary suite features dual closets, spa bath, and pool access. Home includes water softener system, water heater from 2022 and air handler from 2020. Enjoy a private 0.25-acre lot in a tree-lined community. Glenmuir provides a community park with playground, basketball courts, soccer field, pavilion, and picnic areas. Conveniently located near Winter Garden Village, Lakeside Village, and Walt Disney World, the neighborhood is also zoned for top-rated Orange County schools and less than a mile from Windermere Preparatory School.
Listing is courtesy of: LOKATION (954-545-5583)
Listing Agent: David Sanchez (321-262-2322)
13411 LEMON ORCHARD BND, WINDERMERE, FL 34786
$562,09527 Days on yellowkey MLS ID: TB8493546
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1649 Built: 2026Monthly Fee: $280 Tax: $8,670 (2026)Community: Lake Cawood CoveTownhouse
Taxes:$8,670
Remarks: Under Construction. This stylish two-story townhome features three spacious suites, including a second-floor primary suite and two additional bedrooms. The open-concept first floor offers a bright living area and a gourmet kitchen with 42” cabinets, quartz countertops, stainless steel appliances, and luxury vinyl plank flooring. Enjoy a private courtyard and detached two-car garage. Located in the heart of Windermere near top-rated schools, Winter Garden Village, and charming downtown, with community amenities including a pool and playground.
Listing is courtesy of: ASHTON WOODS FLORIDA REALTY LLC (813-918-4491)
Listing Agent: Reed Williams (813-918-4491)
11537 CLAYMONT CIR, WINDERMERE, FL 34786
$1,400,00028 Days on yellowkey MLS ID: O6395210
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3164 Built: 2002Monthly Fee: $283 Tax: $16,031 (2024)Community: Keenes Pointe Ut 04 Sec 31 48 82Single Family
Taxes:$16,031
Remarks: Stunning transitional home in sought after manned gated Keene’s Pointe Community of Windermere! This beautifully renovated home offers a modern, neutral palette with high-end finishes throughout. Step inside to a grand foyer leading to the formal dining room, where coffered ceilings and tall windows flood the space with natural light. The open-concept kitchen and living area is a chef’s dream, featuring a seamless quartz waterfall peninsula, stainless steel appliances, and abundant countertop and cabinet space. The first-floor master suite is a serene retreat, boasting soaring tray ceilings, stylish furnishings, and pull-down shades for added privacy. The ensuite bathroom offers a custom-organized walk-in closet, dual vanities, a spacious garden tub, a large walk-in shower, and a private water closet. Also on the first floor are three generously sized secondary bedrooms, two of which share a Jack-and-Jill bathroom—ideal for multi-generational living or visiting guests. Upstairs, a versatile loft space with elegant laminate flooring provides the perfect setting for a game room, playroom, or home gym. A full bathroom and a spacious fourth secondary bedroom complete the second level. Step outside to enjoy Florida’s year-round sunshine in the private backyard, featuring a sparkling pool and a covered patio—perfect for lounging or entertaining. The home is just steps away from the community park, offering even more outdoor recreation opportunities. As a resident of Keene’s Pointe, you’ll enjoy 24-hour gated security, a fitness center, community docks and boat ramps, and the option to join the exclusive Jack Nicklaus-designed Golden Bear Club (membership not included; buyer to inquire independently). Conveniently located near top-rated schools, Publix, and Lakeside Village Center for all your shopping and dining needs. Don't miss this opportunity to live in one of Windermere’s most sought-after communities—schedule your showing today!
Listing Agent: Julie Bettosini, Pa (321-689-9594)
9940 GROSVENOR POINTE CIR, WINDERMERE, FL 34786
$3,195,00079 Days on yellowkey MLS ID: O6380812
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5071 Built: 2014Monthly Fee: $283 Tax: $29,036 (2024)Community: Keenes PointeSingle Family
Taxes:$29,036
Remarks: Welcome to an extraordinary custom residence located within the prestigious guard-gated golf community of Keene’s Pointe, one of Windermere’s most sought-after luxury enclaves. Built in 2014 and set on an expansive 0.51-acre, this estate offers over 5,000 square feet of refined living space, thoughtfully designed to balance elegance, comfort, and modern functionality. The property enjoys a rare premium setting with serene pond views wrapping both the rear and side of the home, creating a private, picturesque backdrop rarely found within the community. The residence features 5 bedroom suites, including a luxurious primary suite on the main level along with an additional first-floor guest suite, ideal for multigenerational living or extended visitors. Three spacious ensuite bedrooms are located upstairs, each offering comfort and privacy. At the heart of the home, the chef’s kitchen is a true showpiece, appointed with top-of-the-line appliances, custom cabinetry, an oversized island, and seamless flow into the main living and entertaining areas. Expansive windows and sliding glass doors flood the interiors with natural light while framing tranquil water views. Outdoor living is equally impressive, highlighted by a beautiful pool and spa, an extended brick-paver lanai, and a fully equipped summer kitchen, all designed for year-round Florida entertaining. The oversized yard, enhanced by the half-acre lot and pond frontage, provides both privacy and space rarely available in Keene’s Pointe. Additional highlights include: • 3-car garage • High ceilings & architectural detailing • Hidden pantry • Office on the 1st floor • Gas fireplace in the family room and outdoors • Modern transitional finishes throughout Residents enjoy 24-hour guard-gated security, lush landscaping, private roads, and optional membership to the Golden Bear Club, featuring golf, dining, fitness, tennis, and social amenities. Ideally located near top-rated Windermere schools, fine dining, shopping, and major roadways, this exceptional estate represents the pinnacle of luxury living in one of Central Florida’s premier golf communities.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
2958 MARQUESAS CT, WINDERMERE, FL 34786
$1,885,000177 Days on yellowkey MLS ID: O6357302
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4716 Built: 1984Monthly Fee: $215 Tax: $15,228 (2024)Community: Lake Crescent ReserveSingle Family
Taxes:$15,228
Remarks: Recently appraised - Pricing adjusted to reflect current appraised value. This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal retreat for multi-generational living within one of the most exclusive gated communities in the Town of Windermere. Designed for comfort, refinement, and privacy, this home embodies Florida luxury living at its finest, where indoor grace meets outdoor serenity. The split floor plan offers a grand entry foyer, bedrooms on one side and open living/entertaining areas on the other, all wrapped around the screen-enclosed, completely private pool with a built-in summer kitchen. Through the courtyard, you’ll find the spacious guest house, complete with its own living room, bedroom, bathroom on the main floor, and a large upstairs flex room with a screened balcony overlooking the expansive backyard. This property has just undergone a modern renovation, featuring: * A brand-new primary bathroom with dual vanities, oversized shower, dedicated makeup/dressing area, and a custom walk-in closet. * A remodeled kitchen with new flooring, cabinetry, and striking quartz countertops. * Fresh interior and exterior paint, new flooring throughout half the home, and the guest house. * Additional Highlights: • 4.5 bathrooms • Generator • Water softener system • New pavers (front and pool area) • Two new A/C units — 2023 and 2025 • Plantation shutters on all windows • New paint inside & out • Two-car garage • Outdoor summer kitchen • Guest house with full kitchen. This residence is walking distance to Windermere Elementary and the Windermere Recreation Center, offering the best of both convenience and community.
2844 MARQUESAS CT, WINDERMERE, FL 34786
$3,700,000202 Days on yellowkey MLS ID: O6350786
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 5365 Built: 1985Monthly Fee: $215 Tax: $17,334 (2024)Community: Lake Crescent ReserveSingle Family
Taxes:$17,334
Remarks: Welcome to your private sanctuary, where every sunrise and sunset dances over the shimmering waters of Lake Crescent. Nestled within the exclusive gated community of Lake Crescent Reserve, this lakefront masterpiece offers just under 6,000 square feet of newly remodeled, reimagined luxury living. Positioned on a pristine oversized lot surrounded by lush landscaping and majestic oak trees, the home enjoys unobstructed 270-degree lake views with no visible neighbors—a rare combination of privacy, serenity, and natural beauty. Completely transformed inside and out, the home showcases a 2023 roof, stunning exterior renovation, and an open-concept floor plan that enhances both light and flow. The dining area was thoughtfully opened up to create a larger, more connected entertaining space, beautifully complemented by modern light fixtures and exquisite custom finishes throughout. Your resort-style backyard oasis includes a beach tennis court, sparkling pool with waterfalls, relaxing spa, and a fully equipped summer kitchen beneath a wood-look aluminum pergola—perfect for hosting unforgettable gatherings. Step through custom metal doors with glass inlays into a grand entry crowned with a wood-barrel ceiling. The formal living room frames breathtaking views of the pool and lake, while high-end craftsmanship shines throughout—from the stone-arch kitchen with a 15-foot island and glass wine wall to the great room’s 33-foot glass wall, soaring 17-foot wood-beamed ceilings, and elegant gas fireplace. The luxurious primary suite is a true retreat, featuring a two-sided coral stone fireplace, window bench overlooking the lake, and a spa-inspired bath with courtyard views, soaking tub, glass shower, and custom walk-in closet. Step outdoors to an expansive covered lanai ideal for "al fresco" dining and lounging. Whether you’re gathered around the firepit, enjoying sunset cocktails by the infinity-edge pool, or watching native wildlife from your private dock, every corner of this property radiates tranquility and sophistication. Thoughtfully updated with major system enhancements—including two newer A/C units, a new septic tank (2025), new irrigation and lake pump (2022), new hybrid water heater, updated pool motor (2022), salt system, and lighting (2025)—this home delivers the ultimate blend of luxury and comfort. Located just minutes from the Town of Windermere, Downtown Winter Garden, and Winter Garden Village, with easy access to major highways and world-class attractions—this lakefront estate defines Florida luxury living at its finest.
8438 TIBET BUTLER DR, WINDERMERE, FL 34786
$1,650,00064 Days on yellowkey MLS ID: O6378352
4 Days Off yellowkey (back on 4/2/2026)
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3464 Built: 1999Monthly Fee: $298 Tax: $18,880 (2025)Community: Keenes Pointe Unit 01Single Family
Taxes:$18,880
Remarks: Under contract-accepting backup offers. Located within the prestigious golf community of Keene’s Pointe, this elegant residence by renowned builder David Weekley Homes offers a refined blend of sophistication, comfort, and privacy in one of Windermere’s most sought-after addresses. Featuring 5 bedrooms and 4 full bathrooms, this two-story home presents a thoughtfully designed and versatile layout, ideal for both everyday living and effortless entertaining. Set on an oversized homesite, the property stands out with its impressive curb appeal, extended driveway, and 3-car garage. The interiors are filled with natural light and defined by a seamless open-concept design that connects the main living areas with a sense of flow and warmth. The recently renovated kitchen serves as the heart of the home, showcasing an expanded center island, contemporary finishes, high-end appliances, and natural gas connectivity—perfect for gathering and entertaining. The outdoor living experience is equally compelling, featuring a beautifully designed pool, travertine deck, covered patio, and screened lanai, all complemented by a spacious fenced backyard with mature landscaping that enhances both privacy and ambiance. The floor plan offers exceptional flexibility, including a private office that may serve as a library or formal living space, a first-floor primary suite overlooking the pool area, and an additional guest suite on the main level. Upstairs, a dedicated loft/retreat area complements the secondary bedrooms, including a well-designed Jack-and-Jill configuration. Recent updates further elevate the home’s appeal, including a fully renovated kitchen and island, as well as the complete removal of carpet throughout, resulting in a clean, modern, and cohesive aesthetic. Additional highlights include: Interior wall insulation (R-30) for enhanced comfort and quietness Natural gas connection, including outdoor capability Pool views from key living areas Functional and adaptable layout Residents of Keene’s Pointe enjoy 24-hour guard-gated security and access to the exclusive Golden Bear Club, featuring a Jack Nicklaus-designed golf course, resort-style pool, fitness center, tennis courts, and premier amenities. A distinguished residence that embodies elevated living, privacy, and timeless appeal.
Listing is courtesy of: WRA BUSINESS & REAL ESTATE (407-512-1008)
Listing Agent: Daniel Pavel (407-747-3408)
8272 BRYCE CANYON AVE, WINDERMERE, FL 34786
$515,00050 Days on yellowkey MLS ID: O6389547
REDUCED by $15,000 (2.8%) on 04/02/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1888 Built: 2016Monthly Fee: $71 Tax: $7,459 (2024)Community: Windermere Trls Ph 3BSingle Family
Taxes:$7,459
Elementary School: Bay Lake Elementary
Remarks: 3BR/2.5BA bungalow-style home in the Windermere Trails community. This well maintained residence offers an open floor plan with high ceilings, and premium tile flooring throughout the main level. The home includes a gourmet kitchen, upgraded cabinetry in the laundry room. Upstairs, a versatile loft provides the perfect space for an office or media room, alongside a spacious master suite and two additional bedrooms. Perfectly located near Publix, dining, and banking, and zoned for A-rated schools with Bay Lake Elementary situated right at the community entrance.
Listing is courtesy of: CELEBRITY GLOBAL REALTY LLC (407-530-9264)
Listing Agent: Eduardo Pavone (407-232-1241)
5317 KEENES PHEASANT DR, WINDERMERE, FL 34786
$360,00033 Days on yellowkey MLS ID: O6394104
0 Days Off yellowkey (back on 4/2/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1155 Built: 2005Monthly Fee: $213 Tax: $5,412 (2025)Community: Summerport Phase 4Townhouse
Taxes:$5,412
Elementary School: Keene Crossing Elementary
Remarks: Under contract-accepting backup offers. SINGLE-STORY, END-UNIT TOWNHOME WITH BRAND NEW CARPET AND PAINT! Step into this move-in ready Summerport townhome, complete with 2 large bedrooms, covered and screened lanai, spacious kitchen, and updated AC (2025) and roof (2018)! As you enter, you are greeted by a large open concept living and dining space with tons of natural light. The kitchen connects seamlessly to the living area, and features tons of cabinetry, stainless steel appliances, pantry, bar top seating, and additional eat-in kitchen space. The primary suite has a huge walk-in closet, stunning tray ceiling, large vanity with tons of storage, and relaxing soaking tub. The guest bedroom is set away from the primary for added privacy and features its own guest bathroom. Stunning glass French Doors take you out to the covered and screened-in patio, perfect for enjoying the lovely Florida weather! The home also features an attached 2-car garage, large laundry room with included washer and dryer (plus room for storage!), and all exterior maintenance (including roof replacement and painting) and landscaping included! The popular Summerport community features a clubhouse with fitness center, community pool, playgrounds, tennis courts, basketball courts, volleyball court, and walking trails. The location is also prime, with direct access to Keene's Crossing Elementary School, Foxtail Coffee, Kelly's Homemade Ice Cream, and Marco's Pizza right across the street! Centrally located with easy access to CR-535, Walt Disney World, Disney Springs, Winter Garden Village, and Hamlin Shopping, you will never run out of things to do and see. Come see this home before it is gone!
Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)
Listing Agent: Matthew Gordon (732-754-3377)
11658 HAMPSTEAD ST, WINDERMERE, FL 34786
$1,349,90096 Days on yellowkey MLS ID: O6376140
0 Days Off yellowkey (back on 4/1/2026)
Bed: 7 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4563 Built: 2015Monthly Fee: $167 Tax: $11,115 (2025)Community: EnclaveSingle Family
Taxes:$11,115
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 11658 Hampstead Street, a refined Windermere showpiece tucked inside the highly sought-after Enclave community, zoned for Orange County’s top-rated schools. This home defines elevated Florida living, offering 4,563 square feet of thoughtfully designed space created for both effortless entertaining and everyday comfort. Featuring 7 bedrooms plus a dedicated office (with flexibility for a second office or bonus use), 4.5 bathrooms, and an open-concept layout, the home flows seamlessly from room to room—and even better, from indoors to out. The heart of the home opens directly to a massive covered lanai, creating a true indoor-outdoor lifestyle that Florida living is known for. Step outside to your custom resort-style pool with sun shelf, recessed table, and tranquil waterfall. The space is anchored by a fully equipped outdoor kitchen and bar complete with bar seating, keg, grill, smoker, and sink—ideal for hosting game days, celebrations, or quiet evenings at home. Inside, the primary suite on the main level serves as a private retreat, featuring a spa-inspired bath and a custom walk-in closet with built-ins. A secondary primary suite upstairs provides exceptional flexibility for guests or multigenerational living, while the remaining bedrooms and bonus spaces offer endless options for work, play, or relaxation. A rare bonus, the 3-car garage features an 18,000 BTU Bluetooth-controlled AC, making it ideal for a climate-controlled home gym, hobby space, or car enthusiast’s workshop. A three-car garage, beautifully maintained finishes throughout, and access to the community neighborhood park complete the offering. Located in Enclave, you’ll enjoy tree-lined streets, a strong sense of community, and proximity to everything Windermere has to offer—including access to the Butler Chain of Lakes. This is more than a home, it’s a lifestyle.
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)
Listing Agent: Thomas Nickley, Jr (407-629-4420)
3026 PORTO LAGO CT, WINDERMERE, FL 34786
$4,500,00062 Days on yellowkey MLS ID: O6381606
Bed: 5 Bath: 8.0 Gar: 3 Liv Area Sq Ft: 8714 Built: 2003Monthly Fee: $375 Tax: $42,672 (2024)Community: Lake Down Pointe 50 42Single Family
Taxes:$42,672
Remarks: Welcome to an extraordinary 8700+ SQ FT estate located within the GATED COMMUNITY of Marbella in Windemere. This estate offers 40 feet of frontage on Lake Down complete with a private dock and boat lift. Access to Lake Butler & Situated on 2.17 acres, this custom-built pool home blends timeless architecture with superior craftsmanship and premium finishings throughout — including stone, wood, iron, granite, and travertine. A grand entrance featuring custom wrought iron doors opens to a dramatic two-story foyer framed by a stunning wall of windows overlooking the backyard oasis. Elegant formal living and dining spaces are complemented by an oversized wet bar, perfect for entertaining. The gourmet kitchen is designed for both beauty and performance, showcasing custom cabinetry, a six-burner gas cooktop, dual side-by-side refrigerator and adjacent butler's pantry. It seamlessly flows into the impressive great room with cathedral ceilings, exposed beam millwork, fireplace, and expansive glass doors leading outdoors. The luxurious primary suite features volume ceilings with exposed beams, a private sitting area, walk-in closet, and a newly renovated spa-inspired bath with soaking tub and multi-jet walk-in shower. This estate offers four additional en-suite bedrooms, two dedicated offices, media/movie room, craft room, a detached gym and a three-car garage — providing exceptional space and flexibility. Designed for true indoor-outdoor living, the backyard retreat includes a resort-style pool with rock waterfall and slide, spa, pool house, summer kitchen, volleyball court, and lush garden setting — ideal for entertaining or peaceful relaxation. A rare opportunity to own a private lakefront sanctuary in one of the area’s most desirable gated communities.
Listing is courtesy of: SERHANT (786-296-8626)
Listing Agent: Ashley Mccoy (561-758-2155)
1826 WINDERMEREDOWN PL, WINDERMERE, FL 34786
$1,295,00041 Days on yellowkey MLS ID: O6391963
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3856 Built: 1995Monthly Fee: $83 Tax: $11,183 (2025)Community: Windermere Downs Ph 03Single Family
Taxes:$11,183
Remarks: If you need a Separate 1st Floor In-Law Apartment with a Private Entrance overlooking the Screened Pool and Covered Lanai then here it is * Beautifully maintained and updated 5 Bed 4.5 Bath 1 Story Home nestled in one of Windermere’s most desirable Lakefront Communities * This Exceptional Home offers the perfect blend of Comfort, Elegance, and Florida Lifestyle Living * Step inside to discover a bright and open floor plan featuring spacious living areas, high ceilings, and abundant natural light * The gourmet kitchen is a Chef’s dream, complete with modern appliances, ample cabinetry, and a convenient breakfast bar—ideal for entertaining or everyday living * The primary suite provides a peaceful retreat with generous space, a luxurious en-suite bathroom, and a walk-in closet * The Pass Thru from the Primary Suite to the Den with substantial Closets makes the perfect Nursery, Craft Room or Home Office * Additional bedrooms are well-sized and versatile, perfect for family or guests * The Oversized Laundry Room exceeds all expectations * The Massive Covered Lanai provides plenty of space for entertaining in all weather conditions with a backyard the size of a football field * The Conservation Pond out Back feels like you are in the Country even though you are just minutes from every Restaurant, Bank, Hospital, Offices, Retail Store or Mom & Pop Shop that could ever need * Plenty of Biking, Walking & Exercising Opportunities Throughout Windermere * The Neighborhood Park & Boat Ramp to Lake Down & the Famed Butler Chain of Lakes will provide years of family fun * Friday Farmer’s Market & Monthly Food Trucks provide opportunities to meet the wonderful folks in our Community * Easy access to Florida Turnpike, 408, 429 & Interstate 4 make this the perfect place to call home * Solar Electric Panels Provide a Major Savings - Details Available
Listing is courtesy of: VINTAGE REALTY GROUP LLC (407-217-5458)
Listing Agent: Darrell Nunnelley (407-467-8069)
13161 LAKE BUTLER BLVD, WINDERMERE, FL 34786
$3,200,000247 Days on yellowkey MLS ID: TB8421056
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4500 Built: 2001 Tax: $16,201 (2024)Community: Lake Roper PointeSingle Family
Taxes:$16,201
Remarks: Extraordinary lake front opportunity in Windermere on 1.75 acres! PRIVATE GATES! NO HOA! SPECTACULAR LAKE VIEWS, PRIVACY, SPORTS COURT, AND GAZEBO ON LAKE ROPER - A WATER SKI FRIENDLY LAKE! A grand entryway leads you to magnificent two story ceilings and welcomes you into a separate living and family room. Beautiful 5-bedroom, 3/2-bathroom Mediterranean-style home with inlaid marble medallion foyer floor design, coffered ceilings, crown molding, and European-style ironwork boasts spectacular views of Lake Roper. The upstairs master bedroom has a beautiful view of Lake Roper. Master bath features an oversized tub and walk-in closet. This Grand Retreat has plenty of outdoor amenities including a basketball court, boat dock and boat lift. Heated family pool and spa. For all your family entertainment, a large open backyard leads to the dock with plenty of land. Stunning cedar and cypress trees surrender the property reminding you of FLORIDA living at its best. The ideal setting for privacy and serenity! Entertainment and fine shopping just minutes away. Close to major highways such as 429, 408 & the Turnpike. Easy access to the airport and Downtown Orlando yet secluded enough to give you a unique home in the heart of Windermere! Close to Windermere Prep school. Convenient to major highways, shops, restaurants, historic sites, major hospitals, and theme parks! Privacy awaits you! Schedule showing!
Listing is courtesy of: EPIQUE REALTY, INC. (888-893-3537)
Listing Agent: Karolina Taylor (813-702-5478)
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