Location: Windermere
Do Not Show Listings
11026 CONISTON WAY, WINDERMERE, FL 34786
$2,150,00014 Days on yellowkey MLS ID: O6391330
0 Days Off yellowkey (back on 3/29/2026)
Bed: 6 Bath: 7.5 Liv Area Sq Ft: 5783 Built: 2003Monthly Fee: $647 Tax: $20,701 (2025)Community: Reserve At Lake Butler SoundSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$20,701
Elementary School: Windermere Elem
High School: Windermere High School
Tax Year: 2025
Middle School: Bridgewater Middle
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged Step into this former Street of Dreams masterpiece, masterfully crafted by renowned builder David Konkol. Spanning nearly 6,000 square feet of timeless elegance, the home showcases a thoughtfully designed floor plan that prioritizes effortless first-floor living while bathing every space in abundant natural Florida sunshine. The moment you arrive, the circular driveway welcomes you with an ornate fountain and grand double entry doors. Inside, soaring ceilings and exquisite architectural details captivate, complemented by travertine stone floors and a striking stone-encased wood-burning fireplace in the formal living area. Expansive windows frame immediate views of the sparkling pool and private yard beyond. The updated kitchen impresses with premium appliances, including a massive Sub-Zero refrigerator, vented gas cooktop, warming drawers, and a generous prep island—ideal for both casual family meals and grand entertaining. Seamlessly blending sophistication with everyday warmth, the home features a main level billiard room complete with a full bar and half bath. Upstairs, a large bonus room serves the additional bedrooms, one of which functions as a second private suite, alongside a fully equipped home theater for unforgettable movie nights. The lavish first-floor primary suite offers true resort-style living with a convenient morning kitchen featuring pull-out drawer refrigerators, a luxurious Jacuzzi spa tub, bidet, oversized shower, and an enormous walk-in closet with custom built-ins. Outside, your own secluded paradise awaits, fully enclosed by a towering natural hedge that provides lush privacy and a breathtaking natural backdrop. Low-maintenance custom turf covers the yard, accented by a fun putting green. At the center sits a massive heated pool and spa, while the expansive covered lanai creates unparalleled outdoor living with a comfortable sitting area and a cozy wood burning fireplace as its focal point. A summer kitchen, outdoor cabana bath and remote controlled screen walls complete the ultimate Florida lifestyle experience. Additional highlights include a three-car garage and extended driveway for ample parking, EV charger, central vacuum and so much more. Located within The Reserve at Lake Butler Sound—one of Central Florida’s most prestigious 24/7 guard-gated communities. Home to numerous professional athletes, rockstars, and landmark estates like the House of Versailles, this enclave delivers unmatched privacy and security while remaining just minutes from world-class dining, shopping, and attractions. Rarely does a property offer this level of luxury, thoughtful design, and resort-style living at such an exceptional value. 6 bedrooms, 7.5 baths, 2 bonus rooms and a home theatre ! Every bedroom is oversized and has its own full bath.Come experience it for yourself and fall in love with your new home.
Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)
Listing Agent: Ronald Ziolkowski (407-592-7653)
11208 LEDGEMENT LN, WINDERMERE, FL 34786
$1,000,000192 Days on yellowkey MLS ID: O6325096
Bed: 5 Bath: 3.5 Liv Area Sq Ft: 2988 Built: 2002Monthly Fee: $140 Tax: $6,561 (2024)Community: Glenmuir 48 39Single Family
Taxes:$6,561
Tax Year: 2024
Remarks: Upgraded One-Story Pool Home in Gated Community on Oversized Corner Lot****NEW ROOF**** Welcome to this beautifully upgraded one-story home in a desirable gated community, offering nearly 3,000 sq. ft. of thoughtfully designed living space. With five bedrooms, 3.5 baths, and a three-car garage, this home blends comfort, style, and functionality. Upon entry, you’ll be captivated by the high-end finishes and open layout. The formal dining and living areas flow seamlessly together, while sliding glass doors bring the outdoors in, filling the space with natural light. The heart of the home is the oversized kitchen, featuring an island, coffee or wine bar, and direct access to the spacious family room—perfect for entertaining. Large sliding doors open to your own private oasis: a saltwater pool surrounded by lush palm trees, ideal for relaxing or hosting guests. Additional highlights include: • Split floor plan for added privacy • Second bedroom with full ensuite, perfect for guests • Fifth bedroom at the front of the home, ideal for a home office or flex space • Tankless water heater • New A/C system • New pool pump and water filtration system • Wood flooring throughout • Tile floors in the garage * Car Charger *. Surge Protector on Electrical Box *. Attic access via the floor trusses support attic flooring. • Located on an oversized corner lot * appliances 4 years old * * Smart home This move-in-ready home has it all—space, style, and modern upgrades—ready for you to enjoy.
Listing is courtesy of: REVEL REALTY LLC (407-876-6448)
Listing Agent: Ruthanne Martin (407-721-6420)
6315 CLEARMEADOW CT, WINDERMERE, FL 34786
$599,990258 Days on yellowkey MLS ID: O6330497
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2077 Built: 2002Monthly Fee: $170 Tax: $3,701 (2024)Community: Glenmuir 48 39Single Family
Taxes:$3,701
Remarks: ***Freshly painted throughout and new carpet as 0f 3/23 for this move in ready home.*** New photos coming this week. This must-see home is ready to welcome you to the exclusive and upscale gated subdivision of Glenmuir. This spacious property is in an A-rated school district just minutes from Disney, Universal, Sea World, Downtown Windermere, and Winter Garden. Located on a quiet cul-de-sac with nearly half an acre to customize to your taste, it has been over 10 years since one of these 2077 sq ft models has come on to the market. Enter through the double front doors to the open-concept great room that features a retractable sliding glass door to extend your space to the 350 sq ft covered and enclosed patio. The sizable kitchen is equipped with solid wood cabinetry, abundant storage, white quartz countertops (2022), stainless steel appliances, and an eat-in breakfast nook. The large primary suite has an expansive walk-in closet, an oversized bathroom with beautiful glass block window, separate vanities, garden tub, and private water closet. The remaining two bedrooms are a generous size with beautiful natural views. The guest bath is recently remodeled with an upgraded custom shower. The home is meticulously maintained by (original owner) with a BRAND-NEW Spanish tile roof installed in (JULY 2025), sprinkler system upgraded in (June 2025), hot water heater installed in (2020), and A/C replaced in (2017), along with all new blown insulation, new dishwasher (Oct 2025). You will also enjoy the long driveway which can fit at least 6 cars for entertaining. Enjoy the amenities of this well-established and treed neighborhood, including a community park with a playground, basketball courts, and covered picnic area. This home is perfectly situated nearby to major highways including the 408, 429, I-4, and Florida’s Turnpike, and is located near world-famous shopping outlets, golf, and attractions. Don’t miss out on this perfect opportunity to call Central Florida your home. ***Did we mention the new 50k roof ? There is an extra large drainfield added, and comfort height commode added in both bathrooms.
Listing is courtesy of: CORE REAL ESTATE GROUP (407-375-2849)
Listing Agent: Drew Wolski (407-697-7545)
9548 CROWN PRINCE LN, WINDERMERE, FL 34786
$1,460,00041 Days on yellowkey MLS ID: S5144606
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 3997 Built: 1999Monthly Fee: $108 Tax: $8,883 (2024)Community: Windsor HillSingle Family
Taxes:$8,883
Elementary School: None
High School: None
Middle School: None
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 is courtesy of: LA ROSA REALTY LLC (321-939-3748)
Listing Agent: Jessica Oliveira (407-925-9768)
11816 ANGLE POND AVE, WINDERMERE, FL 34786
$835,00035 Days on yellowkey MLS ID: O6388116
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 3391 Built: 2013Monthly Fee: $81 Tax: $10,010 (2024)Community: Windermere Trls Ph 1CSingle Family
Taxes:$10,010
Remarks: Under 15 minutes to Magic Kingdom. Fireworks on your drive home. Dinner at EPCOT on a Tuesday. Located in Windermere Trails, one of Windermere’s most sought-after communities, this home puts you minutes from Hamlin and Winter Garden Village while keeping you close enough to Disney to make everyday life feel anything but ordinary. The backyard is where this home really stands apart. Designed for living, not maintaining, it features low-maintenance faux turf, a fully fenced yard, and a private, open-air pool and spa with no cage, a rare find in Central Florida. The pool is finished with PebbleTec, a saltwater system, and an electric heater, along with a sun shelf with built-in umbrella holder and an extended paver deck for easy entertaining. Inside, the layout is open, functional, and flexible, with versatile spaces that adapt to how you live. The open-concept kitchen and main living area flow seamlessly, while thoughtful upgrades like plantation shutters, custom closets, and surround sound pre-wiring add a polished feel throughout. You are also walking distance to a top rated elementary school, with access to trails, parks, a community dog park with wash station, playground, and fitness area, making day to day life simple. A backyard you’ll actually use, a lifestyle that just works, and a home that fits the way you live.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Ken Pozek (407-813-2773)
713 MAIN ST, WINDERMERE, FL 34786
$2,235,000113 Days on yellowkey MLS ID: O6368185
Bed: 6 Bath: 5.0 Liv Area Sq Ft: 5031 Built: 2013 Tax: $9,559 (2025)Community: WindermereSingle Family
Taxes:$9,559
High School: Olympia High
Middle School: Gotha Middle
Remarks: Architecturally refined and thoughtfully designed, this custom built Transitional Craftsman residence blends timeless craftsmanship with modern luxury in the heart of Historic Olde Windermere. Rich wood detailing, exposed pecky cypress beams, and dramatic stonework create warmth and depth throughout. The chef’s kitchen is both functional and sculptural, featuring a stone-framed cooking alcove, premium JennAir® appliances, custom ceiling-height cabinetry, and a walk-in pantry designed for serious cooks and entertainers. The home offers six bedrooms and six bathrooms, with two main-level owner’s suites providing exceptional functionality and privacy. Multiple living spaces are anchored by a striking floor-to-ceiling stone fireplace and beautiful library with rolling ladder, while upstairs bedrooms and bonus room are thoughtfully designed for comfort and quiet, complemented by quality finishes throughout. Recent updates include a newly installed roof (2024), windows (2025), enhancing both peace of mind and long-term value. A spacious three-car garage adds both convenience and functionality. Outdoors, the home transitions easily to an entertainer’s retreat with covered porches, fireplace, outdoor kitchen, circular firepit, cabana bath, Tiki hut and lush landscaping. Deeded town resident access to the Butler Chain of Lakes and a prime location within Windermere’s vibrant town center with its new re-development complete this rare offering where architectural integrity meets a fun and functional Florida lifestyle.
Listing is courtesy of: THE REAL ESTATE COLLECTION LLC (407-656-7814)
Listing Agent: Kari Fleck (407-925-5283)
2125 KANE PARK WAY, WINDERMERE, FL 34786
$999,998126 Days on yellowkey MLS ID: O6358139
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2743 Built: 1992Monthly Fee: $118 Tax: $8,555 (2024)Community: Willows At Lake Rhea Ph 02Single Family
Taxes:$8,555
Remarks: Welcome to this beautifully updated single-story pool home on a rare 0.71-acre cul-de-sac lot in Windermere’s Willows at Lake Rhea, zoned for A-rated schools and offering exceptional privacy between homes. Surrounded by mature landscaping, the property provides a peaceful setting rarely found in newer communities while still offering convenient access to major roads, shopping, dining, and area attractions. Custom built by well-known local builder Richard Watson, this four-bedroom, three-bath home features a thoughtful layout with formal living and dining rooms, a spacious family room, and a custom pool — ideal for both everyday living and entertaining. Inside, high ceilings, Acacia wood flooring, and abundant natural light highlight the open floor plan with views of the pool and backyard. The formal living room features triple sliding glass doors for seamless indoor-outdoor living, while the formal dining room offers a double tray ceiling, crown molding, and bay window with convenient access to the kitchen and family room. The kitchen and family room feature vaulted ceilings and porcelain tile flooring, with French doors leading outdoors. The kitchen includes soft-close cabinetry, granite countertops, under-cabinet lighting, generous storage, and a stylish backsplash. A bright breakfast nook overlooks the pool, while the family room is anchored by a wood-burning fireplace with built-in shelving. The oversized owner’s suite offers direct access to the pool and a spa-inspired bathroom with a freestanding soaking tub, quartz dual vanities, a zero-entry walk-in shower, and dual custom closets. Two spacious bedrooms share a Jack-and-Jill bathroom with dual sinks, while the fourth bedroom with French doors and a bay window works well as an office, den, or playroom. A third updated bathroom also serves as a convenient pool bath. Outdoor living features a custom pebble-finish pool, spacious deck, and screened lanai with a coffered ceiling, sink, and cabinetry. The expansive backyard provides rare space and privacy between homes with room for recreation or future enhancements. Additional highlights include a laundry room with utility sink and storage, an expansive driveway, and a side-entry garage. The Willows at Lake Rhea is zoned for Windermere Elementary, Bridgewater Middle, and Windermere High, and offers community amenities including tennis and pickleball courts, basketball, playground, and park. Residents also enjoy the nearby library, farmers market, food truck nights, and seasonal events. Optional access to the Butler Chain of Lakes boat ramp provides entry to one of Central Florida’s most desirable boating destinations. Conveniently located near SR-429, SR-408, Florida’s Turnpike, Disney, Universal, Winter Garden Village, and the shopping and dining of Dr. Phillips. Recent improvements include a new air-conditioning system (2025), water heater (2024), new irrigation and pool pumps (2025), and septic drainfield completed in 2018. With its large private lot, quality construction, desirable school zoning, and recent price improvement, this home presents an outstanding opportunity in one of Windermere’s most sought-after communities. Schedule your private showing today.
Listing is courtesy of: INFINITY REALTY GROUP LLC (407-234-2256)
Listing Agent: Deb Schroeder (407-234-2256)
13742 BRAVANTE ALY, WINDERMERE, FL 34786
$455,00034 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)
6876 MERRICK LANDING BLVD, WINDERMERE, FL 34786
$620,00079 Days on yellowkey MLS ID: O6373037
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2781 Built: 2014 Tax: $8,591 (2024)Community: Vineyards/Horizons West Ph 1ASingle Family
Taxes:$8,591
Remarks: The Vineyards in Windermere is a newer, non-gated suburban community with a mix of single-family homes and townhomes, appealing amenities. The house is located on the main corner at the entrance to the community and has excellent garden spaces. Primary suite provides a private retreat with a walk-in closet and a well-appointed en-suite bathroom. Additional bedrooms are generously sized, offering flexibility for family, guests, or a home office. Enjoy outdoor living with a private backyard, perfect for relaxing, entertaining, or adding a future pool. Community pool, cabana, playgrounds, and green spaces for residents’ enjoymentQuick access to shopping, grocery stores, restaurants, services in Winter Garden Village, Restaurant and local centers. Property featuring a fully repainted interior, including kitchen and bathroom cabinets, creating a fresh and modern feel throughout. The home also offers brand-new carpeting, adding comfort and a move-in-ready appeal. A great opportunity for buyers seeking a well-maintained and updated residence.
Listing is courtesy of: INTERNATIONAL REAL ESTATE LLC (407-760-5150)
Listing Agent: Delia Lugo (407-760-5150)
6718 ROMNEY LN, WINDERMERE, FL 34786
$540,00093 Days on yellowkey MLS ID: O6371234
0 Days Off yellowkey (back on 3/28/2026)
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2460 Built: 2005Monthly Fee: $80 Tax: $4,904 (2024)Community: Lakes/Windermere Ph 02ASingle Family
Taxes:$4,904
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Well-maintained 4-bedroom, 2.5-bath home in the heart of Windermere featuring inviting curb appeal with a covered front porch and classic columns. The bright, open layout offers high ceilings, crown molding, and tile and wood-look flooring throughout the main living areas. The kitchen includes dark wood cabinetry, granite countertops, stainless steel appliances, recessed lighting, and a center island open to the living and dining spaces. The primary suite features tray ceiling detail, plantation shutters, and an en-suite bath with dual vanities, soaking tub, and separate glass-enclosed shower. Roof from 2023 and AC updated 2019. A fenced paver patio provides a private outdoor space, with the added convenience of a rear-entry garage and driveway, all located near shopping, dining, and major roadways.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Tyler Gibson Llc (877-366-2213)
7271 SUNNY MEADOW ALY, WINDERMERE, FL 34786
$675,00016 Days on yellowkey MLS ID: O6392619
1 Days Off yellowkey (back on 3/28/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2280 Built: 2015Monthly Fee: $107 Tax: $7,200 (2025)Community: Ashlin Park Ph 1Single Family
Taxes:$7,200
Elementary School: Sunset Park Elem
Middle School: Horizon West Middle School
Remarks: This meticulously maintained contemporary home is ideally situated on a premium FENCED corner lot just steps from the resort style community pool and clubhouse in sought after Ashlin Park in Windermere. Your family will enjoy the private and large fenced yard! This home is like new and features a long list of amazing upgrades - including recently installed luxury vinyl plank flooring and designer lighting. The entire home has a clean and contemporary design aesthetic with smooth walls and ceilings in serene colors, quartz countertops, flat panel 42” cabinets, tumbled marble and glass backsplash, and designer lighting. Tons of windows and double French doors provide abundant natural light for a bright and airy ambience. The kitchen is the heart of every home and this one offers a large island with seating, stainless appliances and an open flow into the family room, dining room and large screened lanai offering the ultimate space to entertain family and friends. The screened lanai is plumbed for a summer kitchen and offers a tranquil space to enjoy your outdoor oasis. The FENCED yard has mature privacy landscaping with room for your family and pets to run and play. Professionally landscaped with a well manicured lawn, the property is the envy of the neighborhood. Upstairs, the master suite is a harmonious retreat with French doors to a private balcony, a huge walk-in closet and a luxurious bath suite featuring a rain shower and jetted tub. The additional bedrooms are ample and elegantly appointed and ALL bedrooms feature luxury vinyl plank floors. The bathrooms are upgraded with premium cabinetry and quartz countertops. Ashlin Park is conveniently located for easy access to highways, theme parks, dining and shopping. The community pool and clubhouse are an easy walk from your front door and there are walking trails and park space throughout this tranquil neighborhood for exercise and leisurely strolls. Enjoy the charm of Windermere with easy access to the Butler Chain of Lakes, world class dining and entertainment, golfing, boating, fishing and more. Known for top-rated schools, Windermere truly offers a wonderful quality of life! This house is truly a MUST SEE! All information intended to be accurate but BUYER SHOULD VERIFY ALL MEASUREMENTS, SQ. FOOTAGE, HOA RESTRICTIONS AND FEES.
Listing Agent: Denise Crabbe (407-592-0692)
12879 EMERSONDALE AVE, WINDERMERE, FL 34786
$399,00051 Days on yellowkey MLS ID: O6383280
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1565 Built: 2010Monthly Fee: $185 Tax: $5,505 (2024)Community: Wickham Park 04 05 06 09 10 11 12 01Townhouse
Taxes:$5,505
Remarks: Under contract-accepting backup offers. Welcome home to this beautiful END-UNIT 3-bedroom, 2.5-bath townhome, thoughtfully designed to maximize space, comfort, and natural light. With abundant windows throughout, the home is filled with sunshine, creating a bright and inviting atmosphere from the moment you step inside. The open-concept floor plan is ideal for both everyday living and entertaining. Enjoy tile flooring in the kitchen, dining, and living areas, complemented by engineered hardwood floors in all bedrooms for a warm and cohesive feel. The spacious primary suite features a large walk-in closet with custom built-ins, while two additional bedrooms share a convenient Jack-and-Jill bathroom, perfect for family or guests. Step outside to your private patio, offering direct access to a detached 2-car garage—a rare and valuable feature. Additional peace of mind comes with a NEW AC system installed in 2025, adding value and energy efficiency. The community offers an impressive array of amenities, including multiple parks, scenic walking trails, a gazebo, clubhouse, and a resort-style pool, all while maintaining a LOW HOA. Ideally located minutes from shopping, dining, major roadways, and popular attractions, and zoned for top-rated schools, this home truly has it all. Schedule your private showing today and experience the perfect blend of comfort, convenience, and community living.
Listing is courtesy of: UNIONE REALTY INC (407-808-9080)
Listing Agent: Kyle Li (407-808-9080)
9319 WOODBREEZE BLVD, WINDERMERE, FL 34786
$574,99546 Days on yellowkey MLS ID: O6384930
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1798 Built: 1986Monthly Fee: $30 Tax: $3,384 (2024)Community: Silver WoodsSingle Family
Taxes:$3,384
Remarks: WONDERFUL WINDERMERE 4 BED/ 2 BATH HOME LOCATED IN THE CHARMING COMMUNITY OF SILVER WOODS. The moment you drive up to this home you are greeted by low maintence landscaping, paver driveway and a unique courtyard entry which makes this home standout. The courtyard is a perfect space to spend the evenings or start your mornings. Sliders from the kitchen lead onto the courtyard. Upon entering you will notice the details: beveled glass front door, split floorplan, large dining and living (open concept) and well-appointed kitchen. The kitchen overlooks the Livingroom and dining room, and boost upgrades you are sure to love. Cherrywood cabinets with pullout shelves, glass doors, pantry, under cabinet lighting, decorative lighting in cabinets, stainless steel appliances and upgraded granite counters. Additional cabinets were added to create workspace or an eat in kitchen space. Just off the kitchen if the laundry area with matching cabinets. The spacious living room is positioned with views of the kitchen and dining space with sliders leading to the massive patio space. Two additional bedrooms are located just off the living room with the hall bath set up for a pool bath if you decided to add one. Just off the dining room you will find the primary bedroom with French doors leading to a private patio space. The primary bath includes a walk in closet space, cherrywood cabinets and a walk in shower. The rear patio has just as many endless options as the front courtyard does...dining spaces or entertaining or both! All this in a home and still just minutes to restaurants, entertainment, shopping, the parks and so much more. Land, Site, and Tax Information
Listing is courtesy of: CHARLES RUTENBERG REALTY ORLANDO (407-622-2122)
Listing Agent: Steven Looper (321-662-3582)
6552 HELMSLEY CIRCLE, WINDERMERE, FL 34786
$479,00017 Days on yellowkey MLS ID: O6392752
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1980 Built: 2008Monthly Fee: $315 Tax: $3,248 (2025)Community: Preston SquareTownhouse
Taxes:$3,248
Remarks: Welcome home to Preston Square in beautiful Windermere! This stunning corner-unit townhome with 4 bedroom, 3 bathrooms offers the perfect blend of comfort, style, and convenience, with a new roof and fresh exterior paint. Step onto the cozy front porch and into a bright, inviting two-story home filled with natural light. The main living areas feature tile flooring throughout; great room showcases a mirror accent wall along with board and batten in the dining area. Kitchen features granite countertops, breakfast bar, stainless steel appliances, and stone backsplash. Sliding glass door leads to a private paver patio, perfect for relaxing or entertaining. Downstairs bedroom with full bath, inside laundry room plus a utility sink leads to the attached two-car garage with long driveway for additional parking. Upstairs you will find 3 additional bedrooms, stunning primary suite with balcony views. Primary bath features dual sinks, large garden tub, and separate shower. Preston Square offers amenities including a stunning community pool, playground, mature landscaping, basketball court, green space for events, and fitness stations. Ideally located near local dining, shopping, top-rated schools, golf courses, hospitals, and major roadways and attractions.
Listing Agent: Morgan Horsley (256-283-8747)
5538 W LAKE BUTLER RD, WINDERMERE, FL 34786
$3,495,00072 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!
Listing is courtesy of: STOCKWORTH REALTY GROUP (407-909-5900)
Listing Agent: Julie Bettosini, Pa (321-689-9594)
12784 GARRIDAN AVE, WINDERMERE, FL 34786
$550,00018 Days on yellowkey MLS ID: O6392486
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 1970 Built: 2012Monthly Fee: $243 Tax: $5,000 (2025)Community: Wickham ParkSingle Family
Taxes:$5,000
Remarks: Welcome to this well-maintained 4-bedroom, 2.5-bath home in the desirable Wickham Park community in Windermere. Offering 1,970 square feet of living space, this home is move-in ready and has been thoughtfully cared for. The layout is both functional and comfortable, making it easy to enjoy everyday living as well as time with family and friends. It’s a home that simply feels right from the moment you walk in. Enjoy low-maintenance living with an HOA that covers exterior maintenance for normal wear and tear, including roof, exterior painting, and landscaping. Residents also have access to a community pool and clubhouse. Additional features include a two-car garage, central air, and walkability to nearby Top rated schools, adding to the home’s overall convenience. Located just minutes from Walt Disney World Resort and close to Winter Garden Village, this home also offers convenient access to nearby grocery shopping, including Publix, along with a variety of dining and everyday essentials. This property offers the perfect balance of location, comfort, and ease of living. A/C was replaced in 2023.
Listing is courtesy of: ELITE GLOBAL REAL ESTATE LLC (407-758-2604)
Listing Agent: Maria Sarmiento Webel (305-793-6614)
8351 BOWDEN WAY, WINDERMERE, FL 34786
$1,199,00014 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)
12121 SILVERLAKE PARK DR, WINDERMERE, FL 34786
$509,00030 Days on yellowkey MLS ID: O6388109
Bed: 4 Bath: 2.5 Liv Area Sq Ft: 2035 Built: 2013Monthly Fee: $33 Tax: $7,699 (2025)Community: Windermere Trls Ph 1Single Family
Taxes:$7,699
Elementary School: Bay Lake Elementary
Remarks: Under contract-accepting backup offers. Enjoy over $35,000 in upgrades in this beautiful Windermere subdivision! This CORNER LOT home is move-in ready with FRESH INTERIOR AND EXTERIOR PAINT * REPLACED CARPETING * RENOVATED SECOND BATHROOM SHOWER * KITCHEN QUARTZ COUNTERTOP * APPLIANCES REPLACED * WASHER AND DRYER INLUDED * WATER SOFTENER/FILTRATION SYSTEM and more! Experience the bright and inviting atmosphere from the moment you enter. The updated kitchen features elegant quartz countertops, stainless steel appliances, and provides the perfect space for cooking, gathering, and entertaining. The secondary upstairs full bathroom has been updated with a newly renovated shower, offering a spa-like retreat within your own home. Additional upgrades include a water softener system, adding comfort and convenience to everyday living. This home is close to theme parks, major roadways, shopping, dining, and top area attractions! You'll enjoy the ideal balance of peaceful neighborhood living and easy access to everything Central Florida has to offer. From its stylish upgrades to its prime location, this home delivers exceptional value and comfort. Come experience everything this spectacular home has to offer!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Amy Moline (407-506-7447)
5036 LATROBE DR, WINDERMERE, FL 34786
$4,900,000189 Days on yellowkey MLS ID: O6346003
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 5548 Built: 1990Monthly Fee: $1,224 Tax: $17,326 (2024)Community: IsleworthSingle Family
Taxes:$17,326
Middle School: Chain of Lakes Middle
Remarks: Within the gates of the renowned Isleworth Golf & Country Club, this beautiful lakefront estate captures the essence of timeless luxury and gracious living. Poised on the shores of Lake Bessie, the 5,548 square-foot residence unfolds across two levels, designed to frame sweeping water views and create effortless spaces for both grand entertaining and quiet retreat. The upper level greets guests with custom French entry doors that flow into the open formal living and dining rooms, perfectly designed for gatherings. The kitchen is spacious and inviting, offering casual dining and seamless access to the main living areas. A richly appointed library adds warmth and refinement, while two en-suite bedrooms complete this floor, including the primary suite. With its oversized windows capturing endless lake vistas, a large sitting area, exterior balcony, and an en-suite bath featuring dual vanities, a soaking tub, and walk-in shower, the primary suite is a sanctuary of light and serenity. On the lower level, the estate offers two expansive bonus areas joined by a well-equipped kitchenette. Ideal for gaming, entertaining, or working from home, both spaces connect effortlessly to the sun-drenched pool terrace—seamlessly integrating indoor luxury and outdoor living. A stunning mature oak tree anchors the property's beautiful lakefront grounds, stretching gracefully toward the water’s edge—a signature of the property’s natural beauty. Beyond the oak tree, Lake Bessie shimmers in full view, offering a breathtaking backdrop to the estate. A rare combination of elegance, versatility, and iconic setting, this residence presents a lifestyle within one of Central Florida's finest communities.
Listing is courtesy of: ISLEWORTH REALTY LLC (407-909-9000)
Listing Agent: Monica Lochmandy (407-230-6888)
13106 ORANGE ISLE DR, WINDERMERE, FL 34786
$815,000123 Days on yellowkey MLS ID: O6361057
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3312 Built: 2022Monthly Fee: $95 Tax: $11,893 (2025)Community: Sanctuary/Lks/WindermereSingle Family
Taxes:$11,893
Remarks: Explore the WINTERSET model from Ryan Homes of the Sanctuary at Lakes of Windermere, a corner unit, this 5- bedroom, 4.5 bathroom in Windermere combines the modern elegance, and a touch of magic with its a DISNEY Fireworks view, offering a lifestyle of unparalleled comfort. Upon entering, you are greeted by those who appreciate a dedicated workspace, the home includes a spacious office and a serene atmosphere, allowing for maximum productivity while working from home. The expansive living room boasts soaring ceilings, allowing natural light to cascade through the large windows, creating an airy and inviting ambiance. The gourmet kitchen is a chef's dream, featuring stainless steel appliances, a large cabinetry, and a spacious island with granite countertops. The adjacent formal dining room is perfect for hosting intimate gatherings or grand dinner parties. The master suite is offering a sanctuary of tranquility, a enormous shower, and dual vanities. Each of the remaining four bedrooms is generously sized, providing comfort and privacy for family and guests. The highlight of the outdoor space is the breathtaking view of the nightly Disney fireworks display, visible from the comfort of your own home. This feature creates a magical atmosphere and makes every evening a celebration.
Listing is courtesy of: FLORIDA CONNEXION PROPERTIES (407-574-2636)
Listing Agent: Victor De Oliveira (321-393-2772)
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