Location: Windermere
Do Not Show Listings
12411 MONTALCINO CIR, WINDERMERE, FL 34786
$1,550,0003 Days on yellowkey MLS ID: O6398677
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3399 Built: 2011Monthly Fee: $150 Tax: $11,027 (2025)Community: Casa Del LagoSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$11,027
Elementary School: Sunset Park Elem
High School: West Orange High
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: A custom home in the desirable Casa del Lago community. The Spanish-style exterior and elegant, clean transitional interior will surely catch your attention. This home offers 4 beds, 4.5 baths, plus an office, 3,400 sq ft under air, a saltwater pool and spa, an outdoor kitchen, and a gas fireplace near the pool. This home is full of upgrades! Porcelain floors, exotic granite throughout the home a full Carrera marble master bath with floating vanities, organize closet system in every bedroom, all bedrooms have their own private bath, $15,000 worth of plantation shutters, $5,000 security system with cameras with access from your smart phone, all of the wood in the home is African Sapele, 7.25" crown molding and base boards in every room, pre-wired surround sound, casement double pane windows as well as spray foam insulation. Too many extras to list. This home is a MUST SEE!!
Listing is courtesy of: CORCORAN PREMIER REALTY (407-965-1155)
Listing Agent: Mauro Costa (321-231-6800)
825 OAKDALE ST, WINDERMERE, FL 34786
$792,5009 Days on yellowkey MLS ID: O6396351
2 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1664 Built: 1935 Tax: $9,799 (2025)Community: Windermere TownSingle Family
Taxes:$9,799
Elementary School: Windermere Elem
High School: Olympia High
Middle School: Gotha Middle
Remarks: THE ONLY HOME ON WINDERMERE’S ICONIC SANDY STREETS UNDER $800,000 — DON’T MISS YOUR CHANCE. Back on the market and better than ever, this charming traditional cottage now features thoughtful exterior enhancements that further showcase its incredible homesite and future potential. Nestled along one of Windermere’s signature sandy streets, this property offers the perfect blend of nostalgia, community, and convenience—just steps from the Farmers Market, Town Hall, Windermere Library, the new Ace Hardware plaza, and beloved town events. Set on an expansive .38-acre lot beneath beautiful mature trees, this 3-bedroom, 2-bath home now features a freshly cleared and improved backyard. Select trees and brush have been professionally trimmed and removed, creating a more open, usable space ideal for recreation, entertaining, or future expansion. Whether you envision a pool, home addition, or simply the ultimate setting for flag football and weekend gatherings, the groundwork has been laid. Inside, the home welcomes you with a vaulted-ceiling great room and kitchen featuring newly refinished REAL wood floors, exposed beams, and abundant natural light. A cozy adjacent living room offers built-in shelving and a double closet. The quaint kitchen blends character and function with tile and wood countertops, vintage-style paneled appliances, and nearby laundry. A separate dining room with REAL wood floors comfortably seats eight and opens through French doors to a refreshed screened rear porch—perfect for relaxing evenings overlooking your newly enhanced backyard. From here, updated wood steps lead directly into the fully fenced yard. The bedroom wing includes two secondary bedrooms with a shared hall bath, while the private primary suite features its own en-suite bath and French doors opening to a secluded outdoor porch. Major updates provide peace of mind: Brand-New Roof & Skylights (11/2025), HVAC (May 2024), Natural Gas Water Heater (Oct 2021), Exterior Paint (Jan 2024), Wired for High Speed Fiber by ATT and more. The home also includes a transferable annual termite bond, recent septic service (June 2025), and ongoing maintenance including tree care and exterior improvements. An oversized carport with a large enclosed storage/workshop space completes this exceptional Windermere opportunity. BACK ON MARKET BY CHOICE — NOT CONDITION. YOUR SECOND CHANCE IS HERE.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Mildred Hershiser (407-758-5263)
5067 SAWYER COVE WAY, WINDERMERE, FL 34786
$2,315,00026 Days on yellowkey MLS ID: O6391750
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3461 Built: 2018Monthly Fee: $253 Tax: $21,824 (2025)Community: Sawyer SoundSingle Family
Taxes:$21,824
High School: Windermere High School
Remarks: STUNNING CUSTOM ESTATE in the EXCLUSIVE GATED community of Sawyer Sound - a private enclave of 20 luxury homes, ideally located across the street from Windermere Prep, and close to excellent dining and premiere entertainment. Built under the meticulous supervision of its owners, one of whom is an accomplished interior designer, this home showcases curated exceptional quality finishes and craftsmanship, and attention to detail. With natural MARBLE FLOORS, soaring ceilings adorned with real WOOD BEAMS, solid-core interior doors, designer lighting, thick crown moulding, beautiful CUSTOM window treatments and appealing color schemes, you'll find LUXURY in every detail. The chef's kitchen is a masterpiece with rare natural stone CRISTALLO QUARTZITE counters featuring under lighting for a warm dramatic glow, custom wood cabinets, a COPPER farmhouse sink, imported fixtures, and all THERMADOR appliances - including an 8 burner NATURAL GAS range and a built in STEAM OVEN that functions as microwave, convection oven, and air fryer. Gatherings in this home are show stoppers with STACKED SLIDING DOORS that disappear to create a seamless transition to the lanai, pool area with gorgeous NATURAL TRAVERTINE, REMOTE CONTROLLED RETRACTABLE SCREENS, NATURAL GAS FIREPLACE, SUMMER KITCHEN, SALT WATER HEATED POOL, and a LUSHLY LANDSCAPED backyard oasis with a tiki hut - LIVE EVERY DAY LIKE A VACATION! Enjoy the comfort of TWO PRIMARY SUITES, each with spa style luxury bathrooms offering large showers, soaking tubs and custom walk-in closets. The main suite has a bedroom in close proximity that would be an ideal nursery, library or office. Two more bedrooms share a beautifully designed bathroom and each has a walk-in custom closet. Rooms are adorned with real wood PLANTATION SHUTTERS and/or DESIGNER MADE WINDOW TREATMENTS, including silk lined drapes with darkening fabric in the primary suite. Practical luxury continues with a huge laundry room with granite counters, custom cabinets, closet, sink and a folding area. The pantry doubles as a thick concrete reinforced “SAFE ROOM" equipped with a phone line and additional security and safety features. ENTIRE HOME NATURAL GAS GENERATOR ensures no interruption to your comfort. Every detail has been thoughtfully considered - from the water softener, energy efficient foam insulation, and double paned windows to the climate controlled three car garage with an EV car charger, epoxy floor, custom storage, large safe, and bike racks. SMART HOME technology allows you to control all systems from your phone - the thermostat, pool, lighting, interior and exterior cameras, and music. COME SEE WHAT SETS THIS MASTERPIECE APART FROM THE REST! EVERY SPACE IN THIS HOMe TELLS A STORY OF LUXURY, DESIGN AND COMFORT - CRAFTED FOR THOSE WHO EXPECT THE BEST! All measurements should be verified by buyer.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Denise Crabbe (407-592-0692)
10577 DOWN LAKEVIEW CIR, WINDERMERE, FL 34786
$3,500,00079 Days on yellowkey MLS ID: O6377244
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 5273 Built: 1986Monthly Fee: $103 Tax: $28,092 (2025)Community: LakesSpa: YesSingle Family
Taxes:$28,092
Elementary School: Thornebrooke Elem
Remarks: Experience true lakefront living on the famed Butler Chain of Lakes. This exceptional custom home offers 137 feet of pristine shoreline and sits on nearly one acre of high, dry land with sweeping panoramic water views and nightly Disney fireworks. Arrive via a circular paved drive framed by mature oaks and step onto the covered porch through an impressive 8 inch solid cedar entry door with artisan leaded glass. Inside, the great room makes an immediate statement with soaring 23’ cathedral ceilings and a striking Tennessee river rock fireplace. Entertain in the showstopping formal dining room, where oversized picture windows perfectly frame the lake. Designed for everyday comfort, the majority of the living space including all bedrooms is located on the main level. The chef’s kitchen is fully equipped with solid wood cabinetry, granite countertops, Sub-Zero refrigerator, Thermador gas cooktop with exhaust, Bosch double ovens, wet bar, walk-in pantry, and a sunlit breakfast area with spectacular water views. The spacious primary suite is a private retreat with its own screened lanai and a spa-inspired bath featuring a shower, jetted tub, dual vanities, and three walk-in closets. Generous secondary bedrooms offer ample closet space and well appointed baths, including a steam shower. Outdoors is where this home truly shines. Enjoy mature landscaping and colorful gardens, plus a motorized screened lanai with a chef-worthy summer kitchen pizza oven, prep area, grill, refrigerator, and TV alongside the pool, heated spa, and gas firepit. The desirable southern exposure delivers refreshing lake breezes and comfortable outdoor living without harsh afternoon sun. The custom floor plan maximizes lake views throughout, and the partially enclosed dock is a rare find grandfathered in, with a boat lift and side jet-ski lift. Additional highlights include newer doors and windows and a tile roof. The Lakes neighborhood also offers a community boat ramp and tennis courts. Enjoy Windermere living on the Butler Chain without the traffic, just minutes from major roads, top schools, shopping, and dining. This rare, well-built lakefront home is ready to welcome you. Be sure to explore the virtual tours.
Listing is courtesy of: THE SIMON SIMAAN GROUP (407-558-1396)
Listing Agent: Simon Simaan (407-558-1396)
8648 POWDER RIDGE TRL, WINDERMERE, FL 34786
$499,00086 Days on yellowkey MLS ID: O6373065
REDUCED by $17,000 (3.3%) on 04/13/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1876 Built: 2014Monthly Fee: $81 Tax: $6,733 (2025)Community: Windermere Trls Ph 1CSingle Family
Taxes:$6,733
Elementary School: Bay Lake Elementary
Remarks: LOCATION, LOCATION, LOCATION! Welcome to this stunning bungalow-style single-family home located in the highly sought-after Windermere Trails community—where lifestyle, convenience, and charm meet at your front door. Built by Meritage Homes (consistently ranked among the best builders in Florida), this residence features the desirable Angelou floor plan offering 3 bedrooms, 2.5 bathrooms, a spacious loft, and 1,876 square feet of thoughtfully designed living space. The open-concept kitchen and living area create a warm, inviting flow—perfect for everyday living and entertaining. Upstairs, you’ll find a versatile loft, a spacious primary suite, and two additional bedrooms with a full bathroom conveniently located between them. Wood flooring throughout the main living areas and a wooden staircase. Step outside and enjoy Florida living at its finest. From the large front porch, take in breathtaking sunsets and the Magic Kingdom nightly fireworks, while the extra-wide private balcony offers peaceful sunrise views. The rear-entry 2-car attached garage and low-maintenance yard provide both functionality and ease of ownership. *** Owned solar panel system (paid in full—no lease) designed to offset most or all of your monthly electric bill.*** The location is truly unbeatable. The home is walking distance to Bay Lake Elementary, as well as top-rated daycare and middle schools—offering unmatched peace of mind for families. Everyday conveniences such as grocery stores, dining, gyms, and shopping are also just steps away, including the newly opened Lakeside Village shopping plaza. Windermere Trails residents enjoy resort-style amenities including a large community pool, playground, dog park, scenic lakes and preserves, and miles of biking and jogging trails surrounded by beautiful retention ponds and local wildlife—perfect for morning walks and outdoor living.
Listing is courtesy of: NOVA REAL ESTATE SERVICES INC (407-592-1744)
Listing Agent: Renan Serretiello (407-415-7317)
6957 NORTHWICH DR, WINDERMERE, FL 34786
$585,000107 Days on yellowkey MLS ID: A4676454
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2667 Built: 2007Monthly Fee: $100 Tax: $8,184 (2024)Community: Lakes/Windermere Ph 04Single Family
Taxes:$8,184
Tax Year: 2024
Middle School: Horizon West Middle School
Remarks: Beautiful two-story, 4-bedroom, 3.5-bathroom home in the highly desirable Lakes of Windermere Phase 4 community. Built in 2007, this well-maintained residence offers 2,667 sqft of living space on a 6,006 sqft lot. The home features a bright, open floor plan, spacious bedrooms, and a functional layout perfect for families and entertaining. Enjoy a serene backyard with privacy, while being conveniently located near top-rated schools, shopping, dining, and major roadways. With a shingle roof, two-car garage, and access to community amenities, this property combines comfort, style, and location in one of Central Florida’s most sought-after neighborhoods. Schedule your showing today!
Listing is courtesy of: FLATFEE.COM (954-965-3990)
Listing Agent: Cliff Glansen
715 MAGNOLIA ST, WINDERMERE, FL 34786
$1,250,0005 Days on yellowkey MLS ID: S5147648
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3390 Built: 1999 Tax: $5,631 (2024)Community: Windermere TownSpa: NoSingle Family
Taxes:$5,631
Remarks: ADU A beautiful home located in the heart of downtown Windermere offering 4-bedrooms, 3-bathrooms, with a perfect blend of comfort and convenience. The house features hardwood floors throughout, and large sliders that open to a beautiful backyard. This is a great home for entertaining or relaxing. This property features a fully equipped ADU with one-bedroom, one-bathroom space, ideal for in-laws, guests, or use as a private office. Located minutes from boat ramps and local amenities. Please schedule your viewing today.
Listing is courtesy of: IRIS INTERNATIONAL (407-448-5085)
Listing Agent: Robert Trien (407-484-8474)
5106 TILDENS GROVE BLVD, WINDERMERE, FL 34786
$1,700,0008 Days on yellowkey MLS ID: O6397273
Bed: 6 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 4572 Built: 2006Monthly Fee: $317 Tax: $12,584 (2025)Community: Tildens Grove Ph 02Spa: YesSingle Family
Taxes:$12,584
Remarks: PARADISE…FOUND. Welcome to this incredible custom-built executive home in Windermere’s esteemed & highly desired Tildens Grove community which welcomes you with 24-hour guard gated security and beautiful quiet tree-lined streets. Get ready for LUXURY around every corner of this home spanning nearly 6,000 square feet of indoor & outdoor living space. Starting with one-of-a-kind curb appeal, this gorgeous home sits on a large lot measuring ½ acre with endless views of beautiful greenspace & water, mature trees & extensive landscaping…peace, privacy & serenity are all yours. Live the Florida lifestyle OUTDOORS in your fully screened resort style saltwater pool & spa with an oversized travertine lanai patio complete with summer kitchen…an incredible outdoor living space ideal for entertaining or enjoying in solitude. The fantastic & flexible floor plan begins with solid wood six lite double entry doors into a grand welcoming foyer which flows directly into the large living spaces. Extremely tall ceilings on both first & second floors with stunning coffered trim details in each room and TONS of gorgeous windows & natural light throughout. The incredible gourmet kitchen is the HEART of this home featuring a large center island, custom cabinetry, recently upgraded quartz countertops & backsplash, built-in appliances including wood-panel refrigerator, wine/beverage cooler, Fisher and Paykel double dishdrawers, walk-in pantry…for the professional chef or amateur, you couldn’t ask for more! Interior & Exterior Neutral Paint in 2022. Custom Closet Built-ins. Plantation Shutters Throughout. This functional floor plan features SIX (6) large bedrooms, FOUR (4) full bathrooms and ONE (1) half bath (four bedrooms & three full baths on first floor -- two bedrooms & one full bath PLUS huge bonus room with half bath & wet bar plumbing on second floor). Large laundry room with tons of built-in cabinets & storage spaces, desk area plus full-sized fridge/freezer. Oversized three car garage with built-in storage and large paver driveway for plenty of parking space. Whole House Aquasana Water Filtration System. Pet-Free Home. The PERFECT location -- you can be tucked AWAY FROM IT ALL, yet located just minutes from shopping, dining, golf and major highways and roadways for easy access to anywhere in Central Florida & beyond -- 18 miles to Downtown Orlando, 25 miles to Orlando International Airport (MCO), 9 miles to world-famous “Restaurant Row” and Arnold Palmer’s Bay Hill, 7 miles to Walt Disney World. In addition to the 24-hour guard gated security (one gate only for entry/exit), Tildens Grove offers a beautiful community park area with large playground, tennis & pickleball courts, basketball court & soccer field. A+ public schools plus options for Windermere Prep & Foundation Academy within minutes. This is THE ONE you have been waiting for…WELCOME HOME!
Listing is courtesy of: TARA MOORE REAL ESTATE (407-738-5588)
Listing Agent: Tara Moore (407-765-3700)
1703 ROBERTS LANDING RD, WINDERMERE, FL 34786
$1,520,000208 Days on yellowkey MLS ID: O6346120
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3288 Built: 1996 Tax: $17,269 (2024)Community: Roberts LandingSingle Family
Taxes:$17,269
Remarks: This elegant and fully renovated lakefront home on Lake Olivia in Windermere offers the ultimate blend of luxury, comfort, and Florida lifestyle. Featuring three master suites plus a guest bedroom and bathroom, the spacious layout is designed for both entertaining and everyday living. Large windows fill the home with natural light and frame breathtaking views of the water, while recent upgrades—including a new roof, new insulation, new tile floors, new kitchen cabinets and countertops, new stainless steel appliances, fresh interior and exterior paint, and updated lighting fixtures-add modern elegance throughout. The east-facing design bathes every room in golden sunsets, creating a warm and inviting atmosphere. Set on 1.4 acres with no mandatory HOA, the property boasts a huge driveway with space for RV or boat parking, along with a twin boat slip dock and covered boat house. Perfectly located near top-rated schools, shops, restaurants, attractions, and major roads, this home is ideal for those seeking the Floridian way of life—where swimming, fishing, jet skiing, and year-round relaxation are just steps from your back door.
Listing is courtesy of: INTERNATIONAL NETWORK REALTY (407-963-8539)
Listing Agent: Wui Keong Goh (407-963-8539)
6840 HELMSLEY CIR, WINDERMERE, FL 34786
$719,99969 Days on yellowkey MLS ID: S5142930
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2847 Built: 2009Monthly Fee: $129 Tax: $5,044 (2024)Community: Preston SquareSpa: NoSingle Family
Taxes:$5,044
Elementary School: None
High School: None
Middle School: None
Remarks: Stunning Preston Square Windermere home — 4 beds, 4 baths and approximately 3,400 sq. ft. of heated living space in a functional two-story floor plan featuring multiple living areas, an open kitchen with an eat-in nook and architectural detailing, tray ceilings, custom built-ins, spacious walk-in closets and a versatile bonus room (ceiling fans throughout) that adapts to your lifestyle. Entertain outdoors in your private saltwater pool with outdoor kitchen sink and exhaust fan for effortless barbecues, enjoy peaceful pond views in front and nightly Disney fireworks from your porch, all within a fully fenced yard. Updates include a pool pump replaced ~2.5 years ago, a pool safety door alarm, and fresh paint about six months ago — an exceptional offering in a premier Windermere community. Owner relocated .motivated seller. Additional features include all appliances, washer and dryer, and a surround sound system in the downstairs family room.
Listing is courtesy of: IAD FLORIDA LLC (407-720-0020)
Listing Agent: Eleanor Desimone (845-796-6951)
14383 CREST PALM AVE, WINDERMERE, FL 34786
$1,166,99082 Days on yellowkey MLS ID: G5107222
Bed: 6 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3550 Built: 2026Monthly Fee: $245 Tax: $2,489 (2025)Community: Palms At WindermereSingle Family
Taxes:$2,489
Remarks: One or more photo(s) has been virtually staged. ELLINGTON II - Our beautiful, huge 2 story home, with 6 Bedrooms and 4 Baths. This great floor plan boasts an open concept family/dining/kitchen area along with a formal dining room, gourmet kitchen, extended 42" cabinets and an extended island. Primary Suite on 1st floor along with an additional bedroom & bath. The primary bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. Triple sliding glass doors and an extended covered lanai. 4 Bedrooms upstairs with 2 full baths and loft, overlooking wooded area.
Listing is courtesy of: OLYMPUS EXECUTIVE REALTY INC (407-469-0090)
Listing Agent: Nancy Pruitt, Pa (352-552-7574)
14354 CREST PALM AVE, WINDERMERE, FL 34786
$1,119,990100 Days on yellowkey MLS ID: G5106241
Bed: 6 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3542 Built: 2025Monthly Fee: $245 Tax: $1,309 (2025)Community: Palms At WindermereSingle Family
Taxes:$1,309
Remarks: One or more photo(s) has been virtually staged. *Images shown are for illustrative purposes only* TIDEWATER W/BONUS - Our beautiful huge 2 story home, located on a beautiful conservation lot, with 6 Bedrooms and 4.5Baths. This great floor plan boasts an open concept family/dining/kitchen area with a gourmet kitchen, extended 42" wrap around cabinets, and an extended island. The owner's bath also contains a spa package with upgraded 3/8" glass enclosure, an additional rainfall shower head, and wall niche. 9' hidden sliding glass doors and a covered lanai. Downstairs flex room works well as an office or study with 2 additional bedrooms and a laundry room. Common areas upstairs include a spacious bonus room and a 6th bedroom with full bath
8724 PEACHTREE PARK CT, WINDERMERE, FL 34786
$850,000195 Days on yellowkey MLS ID: S5135795
REDUCED by $49,000 (5.5%) on 04/07/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3315 Built: 2015Monthly Fee: $216 Tax: $9,856 (2024)Community: Peachtree ParkSingle Family
Taxes:$9,856
Remarks: Recent pricing adjustment creates an exceptional opportunity to own a thoughtfully designed home in one of Windermere’s most sought-after hidden gems. With bonus spaces including a loft, mudroom, screened outdoor patio that goes around the house and a well-appointed this residence offers both refined living and everyday practicality. Experience the magic of Windermere living at Peachtree Park, a boutique enclave of just 28 homes located directly across the street from Walt Disney World. This rare community blends exclusivity, charm, and convenience, offering the perfect setting for both everyday comfort and unforgettable moments. Crafted by Ashton Woods, this Bimini model radiates elegance and functionality at every turn. Step inside to discover wood floors throughout the first level, a private office with French doors, and a formal dining room enhanced with a butler’s pantry and wine cooler. Ideal for entertaining. The gourmet kitchen is the heart of the home, featuring quartz countertops, custom window seating in the breakfast nook, and premium appliances. Upstairs, the primary suite is a true retreat with French doors, a long shower, and a custom walk-in closet. Additional bedrooms include a second suite and a Jack-and-Jill layout, providing flexibility for family or guests. Outdoor living is exceptional, with over 1,000 sq. ft. of decking—including 600 sq. ft. under screen enclosure—overlooking a serene pond and untouched forest, perfect for morning sunrises or evening gatherings. Schedule your private showing today and experience firsthand why Peachtree Park is unlike anywhere else.
Listing is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Marcelo Machado (321-939-3748)
13124 FILLY CT, WINDERMERE, FL 34786
$1,575,000356 Days on yellowkey MLS ID: O6303140
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3300 Built: 1989Monthly Fee: $46 Tax: $15,459 (2024)Community: FarmsSpa: NoSingle Family
Taxes:$15,459
Remarks: Welcome to a rare opportunity in one of Windermere’s most exquisite communities where luxury living meets farmland feel. The Farms community consists of 12 properties of one or more acres each. The community also has a horse stable that homeowners can keep horses. Nestled at the end of a cul-de-sac, this gorgeous estate offers sophistication, premium finishes and a quaint feeling throughout.As you step up to the front entrance, you are greeted by beautiful water fountain. Once inside your living room with a wood burning fireplace welcomes you to your living room on the right. Continuing your way into the house, your inviting family room awaits with an eat in kitchen island completing the scene. The gourmet kitchen is a chef’s dream, outfitted with top-of-the-line appliances and plentiful cabinetry. Retreat to the oversized owner’s suite with double walk-in closets, a luxurious master bathroom and a private sitting area overlooking the pool area. Enjoy an enclosed pool area and expansive backyard. There is also a second master suite with private bathroom and walk-in closet. At the opposite end of the family room there is a hallway leading to another full bathroom and three additional bedrooms. Located just minutes from championship golf courses, downtown Windermere, Winter Garden Village, and top-rated schools, this home offers the perfect blend of tranquility and convenience. Don’t wait, schedule your showing today!
Listing is courtesy of: HOME N OFFICES INTERNATIONAL (407-864-4590)
Listing Agent: Marcelo Brandao (407-864-4590)
14347 CREST PALM AVE, WINDERMERE, FL 34786
$1,108,990393 Days on yellowkey MLS ID: G5094526
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3100 Built: 2025Monthly Fee: $275 Tax: $1,309 (2023)Community: Palms At WindermereSingle Family
Tax Year: 2023
Remarks: One or more photo(s) has been virtually staged. Under Construction. Step into refined living with this exceptional 4-bedroom, 4-bath residence spanning 3,123 square feet of impeccably designed space. Showcasing a sophisticated open-concept layout, this home offers the perfect balance of elegance and functionality. The main level impresses with soaring 10-foot ceilings and seamless laminate flooring, creating a bright, expansive ambiance. The gourmet kitchen is a true showpiece, featuring striking quartz countertops, an oversized island, and abundant custom cabinetry—ideal for both intimate gatherings and grand entertaining. Upstairs, a spacious bonus room with a full bath provides a private and versatile retreat, perfect for a media lounge, guest suite, or executive home office. Indulge in the beautifully designed primary bath, showcasing a spa-inspired walk-in shower with an oversized rain shower and a sophisticated dual vanity—creating the perfect blend of comfort and elegance. An oversized garage adds convenience and ample storage, completing this thoughtfully designed home that exudes modern luxury at every turn.
3328 WAX BERRY CT, WINDERMERE, FL 34786
$925,000170 Days on yellowkey MLS ID: O6355868
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2636 Built: 1984Monthly Fee: $21 Tax: $10,867 (2024)Community: Lake Butler EstatesSingle Family
Taxes:$10,867
Remarks: One or more photo(s) has been virtually staged. Located in Lake Butler Estates, one of Windermere’s most private established communities, this 4-bedroom, 4-bath single-family pool home sits on a 1-acre cul-de-sac lot surrounded by mature oak trees and lush landscaping, with only 11 neighboring homes and access to the Butler Chain of Lakes through the community’s private boat ramp. Built in 1959 and renovated in 2022, this single-story residence offers an open split floor plan, combining luxury finishes with functional everyday living. Interior features include marble flooring throughout the main living areas and engineered hardwood flooring in all bedrooms, high ceilings, crown molding, recessed LED lighting. The living room features a textured accent wall, skylights, and a wood-burning stone fireplace with gas connection that anchors the main living space. The kitchen was redesigned with sealed butcher block counters, stainless steel Samsung appliances, pantry storage, breakfast bar seating, reverse osmosis water treatment system, Samsung dishwasher, Samsung smart oven, pot filler, and a Fotile range hood with self-adjusting capture shield, with both kitchen water and irrigation supplied by well water. A dry bar adds additional entertaining appeal in the living room, while remote-controlled ceiling fans and lights are installed in every bedroom, with new chandeliers in the living and dining rooms. The spacious primary suite includes custom walk-in closet storage with overhead recessed lighting, sliding glass shower enclosure, Kohler rainfall shower, three-head body sprayers with jets, pebble flooring, marble backsplash, dual vanities, soft-close cabinetry, and bidet hookup. The shared bath offers dual sinks, LED anti-fog mirror, pool access, marble finishes, accent wall tile, pebble flooring, and dual shower heads. A newly added full guest bath includes Swiss Madison pedestal sink, Hansgrohe faucet, medicine cabinet, marble finishes, pebble flooring, and Kohler dual shower sprayers, while the en-suite bath in the first bedroom features sliding glass shower doors, marble backsplash, skylight, LED anti-fog mirror, and soft-close cabinetry. Smart-home and energy efficient features include Ecobee smart thermostat, myQ garage opener, smart front door lock, remote-controlled lighting systems and upgraded electrical outlets throughout. Exterior highlights include a screen-enclosed in-ground pool, covered lanai, outdoor workshop, circular driveway, side-entry two-car garage, extended parking pad, and additional rear concrete parking for RV or boat storage. The backyard offers expansion flexibility, allowing room for privacy fencing, a future mother-in-law suite, or an addition. The annual HOA is only $253 and includes access to the adjacent Windermere Recreation Center, offering 3 lighted tennis courts, fenced playground, pet parks, lakefront boardwalk, kayak launch, sand volleyball court, grills, picninc tables and large entertaining pavilion. Zoned for A-rated Windermere schools. Location second to none as this home is within 10 minutes of downtown Windermere where you can enjoy the weekly Farmers Market. Easy access to Interstate 4, Florida Turnpike, local hospitals, and within 30 minutes of Orlando International Airport, Disney World, and Universal Studios. This move-in-ready Windermere property delivers privacy, acreage, and premier community access in one of Central Florida’s most desirable residential corridors. Schedule your showing today!
Listing is courtesy of: PREFERRED REAL ESTATE BROKERS (407-440-4900)
Listing Agent: Ferris Kassar (407-284-8384)
8337 VIVARO ISLE WAY, WINDERMERE, FL 34786
$800,000204 Days on yellowkey MLS ID: O6332989
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3294 Built: 2018Monthly Fee: $268 Tax: $6,438 (2024)Community: Windermere IsleSpa: NoSingle Family
Taxes:$6,438
Elementary School: Castleview Elementary
High School: Horizon High School
Remarks: Discover your dream home in the highly sought Windermere Isle community, just minutes from the world-renowned Disney attractions. This stunning residence offers an unparalleled blend of comfort, convenience, and elegance, making it an ideal choice for families and those who love to entertain. Boasting five spacious bedrooms and four well-appointed bathrooms, this home provides ample space for family and guests. The thoughtful floor plan includes a first-floor bedroom and full bath, perfect for visitors seeking privacy. The oversized owner's suite offers a private retreat, while the loft area adds versatility to the living space. One of the home's standout features is its exceptional storage capacity, a rare find in Florida. The freshly painted exterior and meticulously maintained interior create a like-new ambiance, with elegant touches such as a separate dining room with a coffered ceiling, perfect for formal gatherings or as a flexible office space. The serene setting of this property is truly captivating, with a tranquil pond view that enhances the sense of retreat and relaxation. The extended lanai and expansive backyard provide the perfect backdrop for outdoor activities, entertaining, or simply unwinding in the Florida sunshine. The open floor plan seamlessly connects the gourmet kitchen, breakfast nook, and family room, offering a harmonious space for daily living and hosting guests. Windermere Isle offers a host of community amenities, including a neighborhood pool with cabana, playground, and walking paths. The HOA ensures easy living by providing lawn maintenance, internet, and cable services. Located near top-rated public and private schools, SR 429, and the vibrant dining and shopping options of Horizon West, this home offers the perfect balance of a peaceful neighborhood setting with the convenience of nearby urban amenities. This property is a rare gem in today's market, combining a desirable location, generous living space, and a picturesque setting. Don't miss your chance to call this exceptional residence your new home. Contact me today to schedule a private viewing before it's gone!
Listing Agent: Laurel Kellett (407-758-1136)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,450,00047 Days on yellowkey MLS ID: S5144606
REDUCED by $10,000 (0.7%) on 04/12/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $8,883 (2024)Community: Windsor HillSingle Family
Taxes:$8,883
Remarks: Situated on a premier half-acre lot in highly desirable area of Windermere, this fully renovated 4-bedroom, 4-bath home offers a hard to find 'like-new' living experience. Every detail has been thoughtfully updated, featuring a chef’s kitchen with brand-new Thermador appliances, custom cabinetry, luxury vinyl plank flooring, and designer lighting throughout. The versatile floor plan includes an oversized upstairs bonus room, perfect for a media retreat or home office. Modern systems provide complete peace of mind, including a 2021 roof, dual high-efficiency A/C units, new water heater, and new sliding doors opening to the expansive backyard. An epoxy-finished garage adds style and convenience. Just minutes from the Butler Chain of Lakes, top-rated schools, and world-class golf, this move-in-ready home blends refined design with modern comfort.
Listing Agent: Jessica Oliveira (407-925-9768)
6133 S HAMPSHIRE CT, WINDERMERE, FL 34786
$3,150,0007 Days on yellowkey MLS ID: O6397043
0 Days Off yellowkey (back on 4/11/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 6335 Built: 2000Monthly Fee: $298 Tax: $35,657 (2025)Community: Keenes PointeSpa: YesSingle Family
Taxes:$35,657
Remarks: Under contract-accepting backup offers. Sophisticated Elegance best describes this stunning remodeled 5 Bedroom/5FULL Bath/2 Half bath Golf Course Estate Home in Keene’s Pointe. Upon entering this residence built by master custom builder J. Richard Watson, you will discover the seamless beauty of the 48 x 24 tiles that grace the entire main floor and set the tone for this gorgeous interior space filled with abundant natural light. Your eyes are drawn to the impressive living and dining rooms that meld together in this open concept while already eyeing the dramatic Family Room view through a graceful arched cast stone passage into the “heart of the home”. The remodeled kitchen and family room display an elevated level of design rarely seen today, equipped with new cabinetry and accent lighting accentuating the Cambrian custom countertops and back splash areas and new appliances by Wolf, Sub-Zero and Cove. The adjacent Family Room has a clever hospitality bar hidden behind tall double doors so discreet and refined that you are delightfully surprised when you open them to see the mirrored walls and lighted cabinets storing sparkling glasses and a wine refrigerator! Attractive fireplace framed out in a custom Cambria surround is flanked by matching accent walls to feature your most cherished collectibles. From the foyer to the kitchen, you note several coordinated glass and gold chandeliers that highlight the ivory walls, fresh interior paint and new can lighting and ceiling fans throughout. You will also find a large study, the primary retreat and a guest-ensuite bedroom on the main floor. Just off the kitchen, a lovely staircase beckons you up to a mid-level reimagined home theatre with the latest in sight, sound and special effects. New plush red leather recliners are enhanced with vibrations that mimic the main event on the screen to make you feel like you are in it – not just watching! Other rewards include the private half bath, beverage bar, professional popcorn machine and extra seating to enjoy the ambiance without leaving the room! Continuing up the staircase you will discover the second floor featuring 3 bedrooms, 2 Full Baths: (1 ensuite and 2 bedrooms sharing an oversized bathroom with dual vanities, and soaring ceiling with skylight!) Both the enormous bonus room and the ensuite bedroom open to a screened balcony overlooking the pool, golf course and the nature preserve in the distance. Second floor is all engineered hardwood throughout and all bathrooms are renovated. The spacious outdoor screened living area is impressive as well, with a large pool with pebble tec finish tucked within so easy to maintain its pristine sparkle keeping nearby oak tree leaves out of bounds! Enjoy the built-in fire pit and conversation area, along with a separate wet bar under the covered lanai. There is an additional summer kitchen featuring a natural gas grill and built in “Green Egg” allowing you to manage most any cookout gathering! Finally, light up any event you host any day of the year with the custom Massey Outdoor Landscape Lighting color carousel that allows you to choose your color for any seasonal holiday simply by pressing your app! So, sit back and enjoy the view of the wide eighth fairway of the renown Jack Nicklaus Signature Golf Course in Keene’s Pointe. Come live the lifestyle for which Keene’s Pointe is famous and add just an extra splash of refined elegance to the mix!
Listing is courtesy of: KEENE'S POINTE REALTY (407-876-8879)
Listing Agent: Angela Durruthy (407-496-5811)
13734 LAKE CAWOOD DR, WINDERMERE, FL 34786
$1,390,00071 Days on yellowkey MLS ID: G5107723
2 Days Off yellowkey (back on 4/11/2026)
REDUCED by $110,000 (7.3%) on 04/08/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 4437 Built: 2006Monthly Fee: $172 Tax: $11,421 (2024)Community: Lake Cawood EstatesSingle Family
Taxes:$11,421
Elementary School: Keene Crossing Elementary
Remarks: Under contract-accepting backup offers. NEW PRICE - SELLER MOTIVATED! Welcome to this stunning single-story luxury estate located in the highly sought-after gated community of Lake Cawood Estates in Windermere, Florida. Situated on nearly a full acre at the end of a cul-de-sac, this beautifully maintained four-bedroom, three-and-a-half-bathroom home offers over 4,400 square feet of spacious, thoughtfully designed living with a three-car garage and exceptional privacy. A long driveway and inviting covered front porch create a warm welcome, while soaring ceilings and tranquil pool views greet you the moment you step inside. The open floor plan is ideal for entertaining and everyday living, featuring a grand living room with gas fireplace, formal dining room with wet bar, expansive family room, and a versatile game or bonus room perfect for a media space, home office, or guest retreat. The gourmet kitchen opens seamlessly to the breakfast nook and family room and is beautifully appointed with granite countertops, stainless steel appliances, built-in double ovens, and a large center island. The luxurious primary suite offers tray ceilings, a private fireplace, sitting area, and abundant natural light, along with a spa-inspired ensuite featuring dual vanities, a jacuzzi tub and two spacious walk-in closets. Three additional bedrooms are generously sized with large closets and a convenient cabana bath provides direct access to the outdoor living area. Step outside to your private resort-style retreat featuring a screened heated pool and spa, expansive paver patio, and a fully equipped summer kitchen designed for year-round Florida living and entertaining. Large sliding doors provide seamless indoor-outdoor flow, enhancing the home’s open and airy feel. Built in 2004 and extensively upgraded for modern comfort and peace of mind, this move-in-ready home features a brand-new roof (2024), new A/C system (2024), new well system (2025), new water filtration system, new saltwater pool system (2025), fresh interior paint (2025), updated lighting and fans (2024), and new kitchen and laundry appliances including a GE Café refrigerator and dishwasher and Samsung washer and dryer. The property operates on well and septic, providing efficiency and long-term value. Ideally located near top-rated dining, shopping, and everyday conveniences, this exceptional home is approximately 15 minutes from Walt Disney World and less than 30 minutes from Orlando International Airport. This rare opportunity combines luxury, space, and major system upgrades in one of Central Florida’s most desirable communities. Schedule your private showing today and experience the lifestyle you’ve been dreaming of.
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Angela Schifano (407-953-7476)
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