Location: Windermere
Keyword(s): Bridgewater Middle
Keyword(s) Middle School: Bridgewater Middle
Do Not Show Listings
11455 CLAYMONT CIR, WINDERMERE, FL 34786
$1,249,00021 Days on yellowkey MLS ID: O6396381
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2262 Built: 2003Monthly Fee: $298 Tax: $7,673 (2025)Community: Keenes PointeSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,673
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Better-Than-New Fully Renovated Pool Home in 24-hour gated/attended Keene's Pointe. Home to The Golden Bear Club an 18-hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, dining and swimming. Welcome to your dream home—completely renovated and truly move-in ready! This stunning residence offers the perfect blend of modern upgrades, thoughtful design, and luxurious indoor-outdoor living. Step inside to discover a spacious, light-filled layout featuring three bedrooms, three full bathrooms, formal dining room, and a dedicated office, ideal for working from home or creating a private retreat. A formal dining room with arched window greets you at the entrance, while the heart of the home opens into an expansive great room with an open-concept floor plan, seamlessly connecting the living, dining, and kitchen areas—perfect for entertaining. The low maintenance wood-look tile carries throughout the home.The beautifully updated kitchen boasts a large island that seats 6 comfortably and provides additional storage. White and oak shaker cabinets, Verona quartz on the counters and backsplash, and new stainless steel appliances, create a warm and inviting atmosphere for gatherings both large and small.The primary suite offers two custom closets and bathroom with dual vanities, free-standing tub and zero entry shower. On each side of the kitchen are the two additional bedrooms with full baths to service each offering custom tile detailing and decorative free-standing vanities. From the great room through the triple-panel sliding door you enter the patio overlooking your own private oasis with an oversized pool and spa, recently resurfaced and enhanced with a new pool motor and heater—perfect for year-round relaxation and entertaining. Throughout this home you will find quality features such as designer lighting, crown moldings, and coffered and tray ceilings. Additional highlights include: 3-car garage with ample storage space, tankless gas water heater for energy efficiency and endless hot water, new roof (2022), professionally designed landscaping and much more. Every detail has been thoughtfully updated, offering the feel of new construction without the wait. Located in close proximity to shopping, dining, major tourist attractions, expressways and top-rated public and private schools - space, style and upgrades in every corner, this home truly has it all!
Listing is courtesy of: SOUTHERN REALTY GROUP LLC (407-217-6480)
Listing Agent: Teresa Stewart (407-493-3057)
8375 BOWDEN WAY, WINDERMERE, FL 34786
$1,369,000180 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
Taxes:$9,709
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)
11450 ARBORSIDE BEND WAY, WINDERMERE, FL 34786
$749,901185 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
Tax Year: 2024
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)
11537 CLAYMONT CIR, WINDERMERE, FL 34786
$1,400,00024 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 is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
6130 GROSVENOR SHORE DR, WINDERMERE, FL 34786
$3,500,000154 Days on yellowkey MLS ID: O6361099
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4676 Built: 2010Monthly Fee: $283 Tax: $24,892 (2024)Community: Keenes PointeSingle Family
Taxes:$24,892
Remarks: Remarkable Waterview Estate in Keene’s Pointe! Heated Saltwater Pool, Main-Floor Living, and Expansive Outdoor Living Space. Discover an exceptional custom Goehring & Morgan home offering the perfect blend of functionality and breathtaking outdoor living, located in a cul-de-sac of the exclusive Grosvenor Village within Keene’s Pointe, known for its privacy, guard-gated security, and Golden Bear Club lifestyle. Key Features & Lifestyle Amenities: Heated & Saltwater Resort-Style Pool with travertine decking, water feature, automatic water-fill system, and updated equipment (2022). Spacious Outdoor Living with full summer kitchen, huge covered lanai with automatic screens, fire pit, fenced yard, water views, and sunset orientation. Game / Media Room with Full Bar plus second-floor bonus room, ideal for entertaining, home theater or multigenerational use. Wine Cellar + bar area. Hidden walk-in pantry, custom cabinetry and high-end Wolf 48” gas cooktop. Primary bedroom on the main floor with lanai access + spa-style bath. Office with built-ins off the foyer. 3 bedroom suites on main level each with walk-in closets and private bath access. Newer HVAC systems replaced in Nov 2022 + dehumidifier system (4 units total, serviced Oct 2024). Outdoor elevated garden shed (2024) + premium Vego metal garden beds (50-year durability). Oversized 3-car garage. Interior Highlights: Luxury finishes include travertine flooring, soaring ceilings, extensive trim detail, picture-frame windows, custom lighting, and seamless indoor-outdoor living through 10-ft sliders connecting the family room, game room, and lanai spaces. The open dining room features a signature chandelier and architectural ceiling detail. Primary Suite Retreat: coffered ceiling, large walk-in closet, dual vanities, soaking tub & walk-in shower. All living areas on the first floor create an intuitive and highly desirable floor plan, with the upstairs bonus/game room as the perfect flexible space. Mechanical / System Upgrades: 4 HVAC units (2 replaced Nov 2022; serviced Oct 2024) Dehumidifier located in the bonus room closet Pool equipment updated approx. 2022 Original pool heater in excellent working condition Roof cleaned, repaired & inspected 2023 Community & Location: Keene’s Pointe offers 24-hour guard-gated security, Golden Bear Club golf, tennis, fitness + dining, boat access to the Butler Chain of Lakes, nature trails, and a warm community feel. Minutes to Windermere Prep, Disney, and Universal.
Listing is courtesy of: DOUGLAS ELLIMAN (561-655-8600)
Listing Agent: Dianna Desboyaux (407-920-4601)
9940 GROSVENOR POINTE CIR, WINDERMERE, FL 34786
$3,195,00075 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.
11044 HAWKSHEAD CT, WINDERMERE, FL 34786
$1,359,99949 Days on yellowkey MLS ID: O6388401
REDUCED by $40,001 (2.9%) on 04/02/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4257 Built: 2004Monthly Fee: $634 Tax: $11,066 (2025)Community: Reserve At Lake Butler Sound Ut 2Single Family
Taxes:$11,066
Remarks: Stunning home in the Reserve at Lake Butler Sound-Windermere. This luxury living at its finest located in the prestigious 24 hour guarded community. The property features 5 bedrooms, 4.5 bathrooms, a 3-car garage, and a private heated pool, perfect for relaxing or entertaining. The owner has invested more than $100,000 upgrades..... newly renovated kitchen boasts brand new cabinetry and countertops., creating a modern and stylish space for cooking and gathering. Upstairs, the loft includes brand new hardwood flooring and a full bathroom, making it ideal as a guest suite, media room, office, or versatile multi purpose space. The 3 car garage offers a Tesla charger, Epoxy flooring, Storage Racks, and Shelves..... Enjoy the comfort, elegance, and security of one of Windermere's most sought-after communities.Roof (2023). Air conditions (2020 and 2022). ... No rear neighbor... Please schedule your private viewing today ....
Listing is courtesy of: MAY HO REALTY (407-923-8903)
Listing Agent: Jennie Ho (407-923-8903)
8438 TIBET BUTLER DR, WINDERMERE, FL 34786
$1,650,00060 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)
5317 KEENES PHEASANT DR, WINDERMERE, FL 34786
$360,00029 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)
11821 WATERSTONE LOOP DR, WINDERMERE, FL 34786
$1,548,90037 Days on yellowkey MLS ID: O6390961
5 Days Off yellowkey (back on 3/31/2026)
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3447 Built: 2012Monthly Fee: $442 Tax: $21,545 (2025)Community: WaterstoneSingle Family
Taxes:$21,545
Remarks: Under contract-accepting backup offers. WWaterstone is guard-gated, well-established, and home to something most neighborhoods can't match: a private pedestrian gate with direct access to Windermere Preparatory School, ranked the #1 private K–12 in Orange County. For families, that detail alone tends to end the search. The home itself is a custom Silliman Homes courtyard design, single-story, built with the kind of attention to detail that holds up over time. Wrought-iron courtyard gates and a solid wood entry door set the tone before you ever step inside. Beamed ceilings, hardwood floors throughout the main living areas, custom built-ins, and a gas fireplace. The separate dining room has detailed ceiling work that elevates it beyond most you'll see at this price point. The kitchen delivers at this level. Five-burner gas cooktop, built-in oven, a proper working island, exotic granite countertops, custom cabinetry, and a walk-in pantry that actually fits a household. It opens to the family room with stone accents and a wall of windows looking out to the pool. Good flow, good light. The primary suite is privately tucked away with an oversized walk-in closet and a bath with dual granite vanities, garden tub, and walk-in shower. Four bedrooms, four and a half baths in total, every bedroom with its own private full bath. Secondary bedrooms are generously sized and thoughtfully positioned relative to the rest of the home. Outside: a heat pump heated pool and spa, a full summer kitchen with built-in grill and refrigerator, and a gazebo with its own gas fireplace. Two gas fireplaces, one in the living room and one in the gazebo, mean the ambiance follows you inside or out. The kind of setup that actually gets used. Two whole-house gas water heaters and smart home features keep everything running effortlessly year-round. 24-hour guard-gated security, five minutes to Windermere's dining, shopping, and golf, and in the heart of Central Florida's most iconic attractions. On clear evenings, you don't even have to leave. The Magic Kingdom fireworks are visible right from the backyard. One gate leads to the best school in the area. The other view is Disney. Not many addresses can say both.
Listing is courtesy of: VOLKE REAL ESTATE LLC (407-502-2383)
Listing Agent: Mauricio Penha (561-866-1917)
13742 BRAVANTE ALY, WINDERMERE, FL 34786
$455,00049 Days on yellowkey MLS ID: O6388651
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1912 Built: 2017Monthly Fee: $254 Tax: $6,654 (2024)Community: Vineyards/Horizons West Ph 2BTownhouse
Taxes:$6,654
Elementary School: Independence Elementary
Remarks: Welcome to low maintenance living in the heart of Windermere’s sought after Vineyard Square community. A modern townhome built in 2017 with an OPEN FLOOR PLAN designed for easy everyday living and entertaining. Step inside to a bright and airy oasis with soaring ceilings on the main level, tile flooring throughout the first floor living areas, and generous windows that fill the home with natural light. At the heart of the home, the kitchen features stylish, spacious countertops, ample cabinet storage, and a large functional island that flows seamlessly into the living and dining spaces, perfect for gatherings or a quiet night in. Upstairs, all three bedrooms are thoughtfully arranged to maximize privacy and comfort, with a spacious primary suite, well sized guest bedrooms, and convenient double-vanities in both bathrooms . With 3 beds and 2.5 baths, this townhome offers flexible spaces for a HOME OFFICE, guest room, or media space to fit a variety of lifestyles. Enjoy true Florida indoor/outdoor living with a PRIVATE COURTYARD style outdoor area off the main living space, ideal for grilling, container gardening, or relaxing with morning coffee. Hoa provided LAWN MAINTENANCE means you can spend more time enjoying your home and less time on yard work, creating a truly LOCK AND LEAVE lifestyle. Residents of Vineyard Square enjoy outstanding COMMUNITY AMENITIES including a COMMUNITY POOL, CABANA, TOT LOT PLAYGROUND, and PET PARK areas, giving you resort style recreation just steps from your front door. The tree lined streets and thoughtfully planned common areas create a welcoming neighborhood feel that is perfect for evening walks or bike rides. The location is a major highlight, placing you minutes from world class CENTRAL FLORIDA ATTRACTIONS including WALT DISNEY WORLD, UNIVERSAL ORLANDO RESORT, and ORANGE COUNTY NATIONAL GOLF CENTER AND LODGE, along with nearby shopping and dining. You are also a short drive to WINTER GARDEN VILLAGE with its outdoor events, festivals, and retail, plus access to walking and biking at TIBET BUTLER NATURE PRESERVE, making this an ideal base to enjoy the best of the Orlando area. With it's modern construction, appealing perks, and community feel, this move in ready townhome offers an exceptional blend of comfort, convenience, and lifestyle in the heart of Windermere.
Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)
Listing Agent: Dustin Bragg (407-970-3279)
5538 W LAKE BUTLER RD, WINDERMERE, FL 34786
$3,495,00087 Days on yellowkey MLS ID: O6376859
Bed: 6 Bath: 5.5 Liv Area Sq Ft: 6000 Built: 1982Monthly Fee: $67 Tax: $25,546 (2025)Community: Kelso On Lake ButlerSingle Family
Taxes:$25,546
Remarks: Welcome to 5538 W Lake Butler Road—an expansive, newly renovated estate set on 1.9 acres of lush, lakefront land in arguably one of Central Florida’s most coveted locations, Kelso on Lake Butler. What distinguishes this property is its remarkable dual lake access. Your own private boat dock provides direct skiable waterfront on Lake Davis, while exclusive community privileges grant you gated access to Kelso's private boat ramp on the prestigious Butler Chain of Lakes. This convergence of private waterfront with chain-of-lakes connectivity creates unparalleled boating and recreational opportunities found in few lakefront estates. The expansive grounds and recent outdoor enhancements create an entertainer's paradise that is second to none! A newly upgraded outdoor bar and grill area, resort-caliber pool and spa, and sweeping lawn frame breathtaking sunset views over the water. Boasting 6 bedrooms, 6 bathrooms, 3 car garage, and more than 6,000 square feet of living space, this custom estate offers privacy, scale, and unforgettable lakefront views from nearly every room. From the moment you arrive, the chic coastal architecture, circular drive, and sprawling presence command attention. Step inside to dramatic 25-foot ceilings in the living room with a two story stacked stone fireplace and walls of glass that dissolve the boundary between interior luxury and lakefront beauty. An adjacent sun-filled flex room provides tranquil views of Lake Davis, while the completely remodeled chef's kitchen, with its oversized island, custom cabinetry, high end appliances, adjacent indoor bar and generous family room, is designed for both intimate moments as well as large scale entertaining. The main level's thoughtfully designed primary suite offers serene seclusion with a private sitting area, spa-inspired bathroom, and expansive walk-in closet, complemented by a convenient main-floor office. Upstairs, five additional oversized bedrooms, a versatile loft, dedicated gym, and stunning rooftop deck provide space for every lifestyle need. Recent upgrades give you the ultimate peace of mind, including upgraded lighting throughout, a new roof with GAF Golden Pledge 20 year workmanship warranty, three newer A/C units, updated water heater, Hayward pool heater, new dock motor, new sprinkler system with a lake-fed pump, and a transferable Massey termite bond. Minutes from Disney's back gates, top-tier schools, and Windermere's celebrated shopping and dining, yet completely private and serene—this is lakefront living without sacrifice. Your Kelso compound awaits!
8351 BOWDEN WAY, WINDERMERE, FL 34786
$1,199,00029 Days on yellowkey MLS ID: O6393659
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2599 Built: 2001Monthly Fee: $283 Tax: $8,252 (2025)Community: Keenes PointeSingle Family
Taxes:$8,252
Remarks: Nestled within the highly acclaimed guard-gated community of Keene’s Pointe, this completely remodeled Windermere home offers a 4-bedroom, 3-bathroom estate that showcases timeless architectural details, curated modern finishes, and a seamless indoor-outdoor luxury lifestyle. Step inside to discover a light-filled open layout with tall coffered ceilings, custom-laid wood tile flooring, formal dining, family room, and separate sitting area, all anchored by a gourmet chef’s kitchen featuring quartz countertops, premium stainless steel appliances, and custom cabinetry—effortlessly flowing into expansive living and dining spaces ideal for both everyday comfort and refined entertaining. The luxurious primary suite offers a tranquil retreat with a sitting area, a spa-inspired en-suite bath, and a spacious walk-in closet. 2 of the additional bedrooms are split from the main suite, providing comfort and flexibility with a jack-n-jill bathroom. While a separate 4th bedroom is set apart from the others and can be used as a guest suite or office, it's in a perfect space for remote work or study. Outside, your private oasis awaits—a covered lanai overlooks a sparkling pool and lushly landscaped backyard, creating a serene setting for alfresco dining or lounging under the Florida sun. This residence is also zoned for A-rated schools, within minutes of Windermere’s charming shops, fine dining, and world-renowned attractions. (Roof Replace 2026). This exceptional home invites you to experience the very best of Central Florida living. Schedule your showing today!
Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)
Listing Agent: Sharon Brandt (407-310-3623)
6109 ORTA CT, WINDERMERE, FL 34786
$4,495,000100 Days on yellowkey MLS ID: O6374125
1 Days Off yellowkey (back on 3/27/2026)
Bed: 5 Bath: 6.0 Liv Area Sq Ft: 5895 Built: 2016Monthly Fee: $442 Tax: $65,510 (2025)Community: WaterstoneSingle Family
Taxes:$65,510
Remarks: Under contract-accepting backup offers. Within the gates of the Waterstone community, this exceptional lakefront estate offers approximately 5,895 square feet of refined living space, seamlessly blending modern elegance with timeless sophistication. The thoughtfully designed floor plan features five bedrooms, five full bathrooms, and two half bathrooms, with the primary suite conveniently located on the main level. At the heart of the home is an expansive gourmet kitchen appointed with premium Thermador appliances and granite countertops, perfectly balancing form and function. The kitchen opens effortlessly to the grand family room, creating an ideal setting for both everyday living and entertaining. Soaring ceilings and clean, contemporary finishes throughout the residence underscore the home’s elevated design. Additional highlights include a dedicated wine room, ideal for showcasing a curated collection, and a private office suite that offers a quiet, productive retreat. Outdoor living is equally impressive, featuring a resort-style pool and spa, an outdoor kitchen, and a fireplace—designed for year-round enjoyment. Set on a generous 2.16-acre cul-de-sac lot, the property offers sweeping views of the ski-able Lake Cypress and includes a private dock capable of accommodating jet skis, delivering a truly exceptional waterfront lifestyle.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
11536 CLAYMONT CIR, WINDERMERE, FL 34786
$1,250,00030 Days on yellowkey MLS ID: O6392958
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2882 Built: 2002Monthly Fee: $298 Tax: $8,766 (2025)Community: Keenes Pointe Ut 04 Sec 31 48 82Single Family
Taxes:$8,766
High School: Winter Park High
Remarks: One or more photo(s) has been virtually staged. Welcome to luxury living inside the guard-gated community of Keene’s Pointe, home to the renowned Golden Bear Club and its Jack Nicklaus Signature golf course. Perfectly positioned within one of Windermere’s most sought-after neighborhoods, this exceptional single-story residence offers a refined blend of elegance, comfort, and lifestyle. Beautifully remodeled throughout, this is truly move-in ready, showcasing a fresh, modern aesthetic while maintaining timeless architectural appeal. From the moment you enter, you’re welcomed by marble tile flooring, newly refinished wood floors, fresh interior paint, and thoughtfully selected modern light fixtures that elevate every space. The home features both a traditional dining room and formal living room, complemented by custom window treatments that add warmth and sophistication. At the heart of the home, the completely remodeled kitchen shines with all-new appliances, a gas stove, double oven, quartz countertops, and a large walk-in pantry, all wrapped in a clean, contemporary design that seamlessly opens to the family room—where a decorative modern fireplace creates the perfect gathering space. The expansive primary suite is a true retreat, featuring wood floors, direct pool access, a dedicated mini-split system for enhanced comfort and efficiency, and a spa-inspired bathroom with a stunning new garden tub, separate shower, and an oversized walk-in closet. Additional bedrooms lend to stylish comfort with new herringbone tile flooring and share a convenient Jack-and-Jill bathroom. All bathrooms throughout the home have been fully remodeled with high-end finishes. A large private office with a built-in desk provides the ideal work-from-home environment. Step outside to a spacious, fenced backyard featuring a newly repainted pool and patio—perfect for enjoying Florida living year-round. Additional highlights include a 2020 roof, paver driveway, and an oversized 3-car garage. Every detail has been thoughtfully updated, making this home completely turn-key. Residents of Keene’s Pointe enjoy 24-hour guard-gated security and a lifestyle centered around both recreation and natural beauty. The community offers private access to the Butler Chain of Lakes, ideal for boating, skiing, and sunset cruises, along with scenic walking paths, tranquil green spaces, and a peaceful, well-maintained setting throughout. There is even the opportunity for boat storage, adding convenience for those looking to fully embrace the lake lifestyle. Optional membership to the Golden Bear Club unlocks a premier lifestyle experience with championship golf, tennis, fitness, a resort-style pool, dining, and a vibrant calendar of social events. The neighborhood also features community parks, playgrounds, and gathering spaces, creating a welcoming environment that blends luxury living with everyday convenience and community connection through regular neigborhood events. Whether you're relaxing poolside, entertaining guests, or enjoying the unmatched lifestyle of this premier golf and lakefront community, this home delivers the very best of Central Florida living.
Listing is courtesy of: MATT ALLEN REAL ESTATE LLC (321-228-5555)
Listing Agent: Matt Allen (321-228-5555)
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