Windermere, FL Homes

/73
$5,900,000
- 4 Beds
- 4.5 Baths
- 7,491 Sq Ft
9826 Laurel Valley Dr, Windermere, FL 34786

Tucked within the gates of Isleworth Golf Community and Country Club lies a residence that feels more like a private lakeside retreat than a home. Here, more than 7,000 square feet of elegance unfolds across a premium homesite on the shores of Lake Butler, where the water is clear, the sandy beach is pristine, and the sunsets spill across the horizon in dazzling color every evening.The

Dianna Desboyaux SOUTHERN REALTY GROUP LLC

9826 Laurel Valley Dr, Windermere, FL 34786
/28
$4,900 per month
- 4 Beds
- 4 Baths
- 3,144 Sq Ft
- House for Rent
11445 Vicolo Loop, Windermere, FL 34786

Gorgeous pool home ready for tenant in desirable gated Belmere community with private pool and spa. Solid flooring throughout. Primary bedroom and additional bedrooms on first floor. Bonus room/bedroom and bath on second floor. 3 car garage; tile roof; paver driveway. Community has tennis, playground amenities and very walkable. Pool and lawncare included in rent. Bike ride to downtown

Dawn Briggs BLUE MAGNOLIA REALTY LLC

11445 Vicolo Loop, Windermere, FL 34786
/2
$850,000 Sold Aug 15, 2025
- Land
- 0.26 Acre
- $3,269,231 per Acre
- 19 Days On Market
0 Gladys Garden Ct, Windermere, FL 34786

Within the gates of Isleworth, this beautiful home site is positioned within the Gardens of Isleworth - an intimate enclave of custom homes surrounded by lush gardens, water features, bridges, and walking paths. The home site will feature a beautiful estate celebrating the best of indoor-outdoor living to be built by leading luxury custom home builder Goehring & Morgan Construction.

Wayne Sheffield ISLEWORTH REALTY LLC

0 Gladys Garden Ct, Windermere, FL 34786

/38
Est $774,847 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 3,598 Sq Ft
13327 Charfield St, Windermere, FL 34786

13327 Charfield St, Windermere, FL 34786

/82
$725,000 Open Fri 4:30PM - 7PM
- 4 Beds
- 3 Baths
- 3,103 Sq Ft
12880 Holdenbury Ln, Windermere, FL 34786

Immaculate, beautifully upgraded, 4 bed, 3 full bath, Victorian style home brimming with charm and character, nestled on a corner lot of just under 1/4 acre in the highly desirable Lakes of Windermere community. Situated on a beautiful tree-lined street with over 3100 sq ft of living space, the property welcomes you with pretty wrap around porch and mature landscaping. Upgrades include - NEW

Sue Webb WATSON REALTY CORP.

12880 Holdenbury Ln, Windermere, FL 34786
/22
$2,800 per month
- 3 Beds
- 2.5 Baths
- 1,768 Sq Ft
- Townhouse for Rent
8620 Wellington Blue Ln, Windermere, FL 34786

Beautiful townhome in Windermere Trails with first floor master bedroom. Excellent location - walking distance to Bay Lake Elementary, as well as shopping and dining. This well maintained unit offers 3 bedrooms (master down with 2 closets) and two bedrooms with full bath, bonus/loft area and laundry located on the second floor. Tastefully decorated throughout with gray and white accents. Kitchen

Teresa Stewart SOUTHERN REALTY GROUP LLC

8620 Wellington Blue Ln, Windermere, FL 34786
/2
$635,000 Sold Aug 15, 2025
- 2,020 Sq Ft
- $314/SF
- 44 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1985
4833 Palm Tree Ct, Windermere, FL 34786

Welcome to your Oasis at 4833 Palm Tree Ct. a beautifully maintained single-story residence nestled in the heart of Windermere's most desirable community. This charming 4-bedroom 2.5-bathroom home offers the perfect blend of comfort style & convenience creating an idyllic Florida lifestyle for you and your family.Step inside and be greeted by a sense of light and spaciousness. The tile

Charles Kohlinger BHHS FLORIDA REALTY

4833 Palm Tree Ct, Windermere, FL 34786

/34
Est $473,177 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,904 Sq Ft
13829 Ingelnook Dr, Windermere, FL 34786

13829 Ingelnook Dr, Windermere, FL 34786

/18
$788,000
- 4 Beds
- 3.5 Baths
- 3,091 Sq Ft
7211 Still Pond Ln, Windermere, FL 34786

Attention investors, this property has a tenant and is ready to be your rental income.Welcome to this former model home in one of Windermere's coveted communities. This custom-designed model is situated on a premium corner lot and offers a combination of luxury, convenience and comfort. As you drive down beautifully manicured streets and past serene lakes, you will arrive at this charming home

Victor Barroeta MBT REALTY LLC

7211 Still Pond Ln, Windermere, FL 34786
/59
$6,500 per month
- 3 Beds
- 2.5 Baths
- 2,851 Sq Ft
- House for Rent
8399 Bowden Way, Windermere, FL 34786

This stunning waterfront home with a pool in the desirable 24-guard gated neighborhood of Keene’s Pointe is available for immediate occupancy! Welcome home to your exquisite single-story remodeled home spanning 2,851 sq ft with an open-concept design, featuring wood floors with contemporary style throughout. Highlights include spacious bedrooms, a separate study, living room, dining room, and a

Simon Simaan THE SIMON SIMAAN GROUP

8399 Bowden Way, Windermere, FL 34786
/2
$1,655,000 Sold Aug 15, 2025
- 3,104 Sq Ft
- $533/SF
- 112 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1975
1424 Kelso Blvd, Windermere, FL 34786

Welcome to 1424 Kelso Boulevard, a stunning luxury waterfront estate that seamlessly blends elegance and modern comfort. This 4-bedroom, 2.5 bathroom masterpiece offers unparalleled craftsmanship and breathtaking water views, creating the perfect sanctuary for refined living. Upon approaching the home you are greeted by the recently brick paved circular driveway with ample parking for all the

Carmen Aridas RE/MAX PRIME PROPERTIES

1424 Kelso Blvd, Windermere, FL 34786

/45
Est $440,567 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,881 Sq Ft
7432 Ripplepointe Way, Windermere, FL 34786

7432 Ripplepointe Way, Windermere, FL 34786

/63
$1,100,000
- 4 Beds
- 5 Baths
- 3,425 Sq Ft
7545 Lake Albert Dr, Windermere, FL 34786

Welcome to 7545 Lake Albert Drive. Where timeless architecture meets modern luxury. Nestled on an expansive lot in one of Windermere's most sought after communities, this stunning estate offers the perfect balance of privacy, comfort, and resort-style living just minutes from Walt Disney World and the best of Central Florida.Arrive via a long, elegant driveway, framed by lush

Nicole Mickle OLYMPUS EXECUTIVE REALTY INC

7545 Lake Albert Dr, Windermere, FL 34786
/37
$2,950 per month
- 4 Beds
- 2.5 Baths
- 2,028 Sq Ft
- Condo for Rent
Unlisted Address

Townhouse in gated community near Disney. furnished, 4 bed/2.5 bathroom 2 cars garage.Water, basic cable included.

Adriana Amorim INT'L PROFESSIONAL REALTY INC

Unlisted Address
/2
$1,755,000 Sold Aug 15, 2025
- 3,680 Sq Ft
- $477/SF
- 108 Days On Market
- 5 Beds
- 4.5 Baths
- Built 2011
11856 Vinci Dr, Windermere, FL 34786

Beautiful Keene's Pointe custom mediterranean home featuring 5 bedrooms, 4-1/2 bathrooms and a 3 car side garage on a large homesite. As soon as you enter through the oversized double wood doors, you will immediately be greeted by the spacious formal living room with an oversized covered lanai with views of the pool. The primary bedroom is bathed in light from the extra tall windows and high

Oscar Rodriguez B LIVE COMMERCIAL AND RESIDENTIAL REAL ESTATE

11856 Vinci Dr, Windermere, FL 34786

/2
Est $1,879,621 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,228 Sq Ft
5608 Marleon Dr, Windermere, FL 34786

5608 Marleon Dr, Windermere, FL 34786

/48
$920,000
- 5 Beds
- 4 Baths
- 3,640 Sq Ft
9335 Westover Club Cir, Windermere, FL 34786

Welcome to Westover Club, one of Windermere's most desirable gated communities where tree-lined streets and a perfect location set the stage for your dream home!This beautifully maintained 5-bedroom, 4-bath home sits on an expansive one-third acre lot and offers the perfect blend of comfort, style, and functionality. Step inside to an inviting foyer that opens to a formal dining room and

Megan Hedrick Mark Spain Real Estate

9335 Westover Club Cir, Windermere, FL 34786
/13
$2,800 per month
- 4 Beds
- 2.5 Baths
- 2,139 Sq Ft
- House for Rent
11661 Black Rail St, Windermere, FL 34786

well located 4 bedroom house. Great community with pool and high rated school. Convenience location with lot of amenities around it.

Mengshi Lu JOY ESTATE ENTERPRISE INC

11661 Black Rail St, Windermere, FL 34786
/2
$1,075,000 Sold Aug 14, 2025
- 2,976 Sq Ft
- $361/SF
- 6 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1999
6054 Caymus Loop, Windermere, FL 34786

Welcome to 6054 Caymus Loop in the 24-hr gated/attended community of Keene's Pointe. One of the most desired communities in Orlando. This updated home has 5 bedrooms, 3 1/2 baths, office/den and formal dining/living, and is located on the 13th fairway of The Golden Bear Club. The first floor features the office/den and bedroom with walk-in closet, as well as functional kitchen with updated

Teresa Stewart SOUTHERN REALTY GROUP LLC

6054 Caymus Loop, Windermere, FL 34786

/2
Est $1,761,141 Not Listed For Sale
- 5 Beds
- 6 Baths
- 4,675 Sq Ft
5566 Marleon Dr, Windermere, FL 34786

5566 Marleon Dr, Windermere, FL 34786

/67
$689,000
- 4 Beds
- 3 Baths
- 2,644 Sq Ft
4837 Indian Deer Rd, Windermere, FL 34786

Welcome Home to One of the Best Floorplans in Summerport! This beautifully maintained single-story home offers 4 bedrooms, 3 full bathrooms, and a spacious 3-car garage with plenty of parking—all in one of Summerport’s most desirable and functional layouts.Extensively renovated in 2021, this home showcases all-new kitchen cabinets, bathroom vanities, and elegant quartz countertops

Michael Chen LA ROSA REALTY LLC

4837 Indian Deer Rd, Windermere, FL 34786
/31
$5,000 per month
- 4 Beds
- 3 Baths
- 2,384 Sq Ft
- House for Rent
11585 Claymont Cir, Windermere, FL 34786

Welcome to Keene's Pointe! You will love calling this exclusive 24-hour guard gated community your home! Step through the front doors into the tiled foyer of this spectacular 4 bedroom, 3 bath home in pristine condition. A bright and airy formal dining room sits left of the foyer and a formal living room to the right. A spacious kitchen features upgraded 42-inch cabinets, includes side by side

Todd Henry SUMMERSIDE REALTY LLC

11585 Claymont Cir, Windermere, FL 34786
/67
$1,250,402 Sold Aug 13, 2025
- 4,443 Sq Ft
- $281/SF
- 6 Beds
- 4.5 Baths
- Built 2025
14249 Crest Palm Ave, Windermere, FL 34786

The Sweetwater floorplan offers expansive living with its thoughtfully designed two-story layout. This home features six spacious bedrooms and four and a half bathrooms, perfectly accommodating larger households or guests. With over 4,400 square feet of living space, the Sweetwater includes both a flex room and multiple bonus spaces, offering flexibility for hobbies, workspaces, or entertainment

Dream Finders Homes

14249 Crest Palm Ave, Windermere, FL 34786

/22
Est $418,583 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,466 Sq Ft
11637 Water Run Alley, Windermere, FL 34786

11637 Water Run Alley, Windermere, FL 34786

/48
$975,000
- 5 Beds
- 3 Baths
- 4,169 Sq Ft
1924 Katie Hill Way, Windermere, FL 34786

Welcome to your dream home in the exclusive gated community of Westover Club, ideally situated in highly sought-after East Windermere and zoned for top-rated Thornebrooke Elementary, Gotha Middle, and Olympia High School. This expansive 5-bedroom, 3-bathroom executive residence offers over 3,600 square feet of elegantly upgraded living space, perfectly blending comfort, functionality, and

Andy Neal MAXIM REALTY ORLANDO

1924 Katie Hill Way, Windermere, FL 34786
/39
$2,700 per month
- 3 Beds
- 2 Baths
- 2,058 Sq Ft
- House for Rent
13324 Longacre Dr, Windermere, FL 34786

Gorgeous & Spacious One Story Home with 3 bedrooms, 2 baths, plus spacious office/den and approximately 2058 Sq. Ft. This house offers Stainless Steel Appliances, 42" wood cabinets with crown molding, and granite countertops. The house is located in the community of Windermere Terrace in Windermere. Community Features: Swimming Pool with Cabana, Playground, Close to Lake Buena Vista

Amanda Yuan MULTI CHOICE REALTY LLC

13324 Longacre Dr, Windermere, FL 34786
/2
$560,000 Sold Aug 13, 2025
- 2,265 Sq Ft
- $247/SF
- 19 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2007
6539 Chagford Ln, Windermere, FL 34786

Welcome to 6539 Chagford Lane located within the beautiful community of Lakes of Windermere! This charming and well-maintained single-story home features 3 bedrooms and office with spacious closets, fenced-in backyard, new roof (2021) and numerous thoughtful upgrades throughout including custom closet systems by Closets by Design installed in the office, laundry room, and primary bedroom. The

Lori Lucente-Nelson RE/MAX PRIME PROPERTIES

6539 Chagford Ln, Windermere, FL 34786

/97
Est $2,271,825 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,500 Sq Ft
Unlisted Address

Unlisted Address

/57
$12,995,000
- 7 Beds
- 10 Baths
- 16,257 Sq Ft
9935 Lake Louise Dr, Windermere, FL 34786

Experience the pinnacle of luxury living in this extraordinary lakefront estate located in the world-renowned Isleworth Golf & Country Club. Positioned on 2.14 private acres along Lake Louise, part of the Butler Chain of Lakes, this 24,950 sq ft masterpiece (16,259 under air) blends timeless craftsmanship, modern amenities, and a warm, inviting design that makes even the most expansive spaces

Jill Irwin IRWIN REALTY GROUP LLC

9935 Lake Louise Dr, Windermere, FL 34786
/43
$2,990 per month
- 3 Beds
- 2.5 Baths
- 2,211 Sq Ft
- House for Rent
11235 Rapallo Ln, Windermere, FL 34786

Perfect beautiful 3 bed 2.5 bath home for rent. This beautiful home is located in the gated community of Belmere Village. Featuring laminate flooring in the bedrooms,otherwise tiled,formal dining/living and a large family room, large screened patio and nicely landscaped. The master bedroom features a bonus room off to the side which has a closet and could be a small childs room, separated by

D'Anne KinCannon IN TOUCH REAL ESTATE LLC

11235 Rapallo Ln, Windermere, FL 34786
/2
$4,100,000 Sold Aug 13, 2025
- 6,196 Sq Ft
- $662/SF
- 41 Days On Market
- 5 Beds
- 7 Baths
- Built 2018
3428 Chaine Du Lac Blvd, Windermere, FL 34786

From the moment you arrive, this home makes a statement. Meticulous architectural details like rafter tails, handcrafted corbels, and a bell cast roof flare immediately set the tone for the craftsmanship within. Subtle soffit LED lighting and artfully placed landscape lighting create an evening ambiance that feels both welcoming and cinematic.Step through the grand double doors and enter

Mauro Costa CORCORAN PREMIER REALTY

3428 Chaine Du Lac Blvd, Windermere, FL 34786

/36
Est $354,119 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
14335 Oasis Cove Blvd Unit 2004, Windermere, FL 34786

14335 Oasis Cove Blvd Unit 2004, Windermere, FL 34786

/30
$798,100
- Land
- 0.49 Acre
- $1,628,776 per Acre
1516 Hempel Ave, Windermere, FL 34786

Vacant Land – 1⁄2 Acre in WindermereBuild your dream home or secure a smart investment in one of Central Florida’s most highly desired communities—Windermere!Spacious 1⁄2 acre lot with endless possibilitiesPrime location in the heart of WindermereSurrounded by A+ rated schoolsEasy access to shopping, dining, and major highwaysRare opportunity in a highly desirable

Matthew Hughes REAL BROKER, LLC

1516 Hempel Ave, Windermere, FL 34786
/7
$1,500 per month
- 1 Bed
- 1 Bath
- 800 Sq Ft
- House for Rent
2156 Merrybells Dr, Kissimmee, FL 34746

Welcome to this beautifully appointed mother-in-law suite featuring a spacious bedroom with ample natural light, a full bathroom, and a separate living area ideal for relaxing or entertaining. The suite also includes a kitchenette with modern cabinetry, a dedicated entrance for added privacy, and direct access to the main home when desired. Thoughtfully designed with neutral finishes and tile

Mayling Marrero KELLER WILLIAMS ADVANTAGE III

2156 Merrybells Dr, Kissimmee, FL 34746
/2
$1,450,000 Sold Aug 13, 2025
- 3,319 Sq Ft
- $437/SF
- 64 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1999
8430 Woburn Ct, Windermere, FL 34786

Waterfront Luxury in Keene’s Pointe – Fully Renovated & Priced to MoveWelcome to resort-style living in one of Windermere’s most exclusive 24/7 guard-gated communities. Set on a quiet cul-de-sac with peaceful lake views, this bold, fully renovated masterpiece in Keene’s Pointe blends timeless elegance with modern design—and it’s move-in ready.Inside, you’ll find high-end imported

Mauricio Penha VOLKE REAL ESTATE LLC

8430 Woburn Ct, Windermere, FL 34786

/37
Est $532,702 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
11607 Black Rail St, Windermere, FL 34786

11607 Black Rail St, Windermere, FL 34786

/65
$6,395,000
- 5 Beds
- 8.5 Baths
- 11,861 Sq Ft
9639 Westover Roberts Rd, Windermere, FL 34786

Welcome to a residence that transcends even the highest expectations of luxury living! This is a once-in-a-lifetime estate where architecture, scale, and location combine to create an experience that is as rare as it is breathtaking.From the moment you arrive, the home commands attention with a grand, Mediterranean-inspired facade that opens to interiors of soaring scale and meticulous marble

Julie Bettosini STOCKWORTH REALTY GROUP

9639 Westover Roberts Rd, Windermere, FL 34786
/18
$2,500 per month
- 3 Beds
- 2.5 Baths
- 1,712 Sq Ft
- Townhouse for Rent
11692 Water Run Alley, Windermere, FL 34786

Welcome to this beautiful 3-bedroom, 2-bathroom home located in the highly sought-after area of Windermere, FL. This property offers a spacious layout with plenty of room for entertaining and relaxation. Inside you will find 10-foot ceilings, rich laminate wood flooring, upgraded interior doors, and expansive windows that flood the home with natural light. Crown molding accents and custom blinds.

Greg Mann BETTER HOMES AND GARDENS REAL ESTATE MANN GLOBAL P

11692 Water Run Alley, Windermere, FL 34786
/2
$910,000 Sold Aug 12, 2025
- 2,897 Sq Ft
- $314/SF
- 5 Days On Market
- 4 Beds
- 3 Baths
- Built 2004
13838 Bluebird Park Rd, Windermere, FL 34786

Waterfront Living in Windermere! Welcome home to this exquisite one-story pool home in Summerport, ideally positioned with sweeping water and sunset views—and nightly Magic Kingdom fireworks from your backyard. With elevated views of Walsh Pond in the rear and sunrise water views in the front, this property offers a rare and serene setting. Walsh Pond is a spring-fed lake known for bass fishing,

Deb Schroeder INFINITY REALTY GROUP LLC

13838 Bluebird Park Rd, Windermere, FL 34786

/41
Est $326,147 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
Unlisted Address

Unlisted Address

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