Windermere, FL Homes

/52
$5,494,000
- 5 Beds
- 6.5 Baths
- 4,665 Sq Ft
5199 Latrobe Dr, Windermere, FL 34786

Nestled in the exclusive and coveted gated community of Isleworth, this fully remodeled, turn-key golf estate is positioned along Isleworth’s famed championship golf course. This remarkable golf-front property reveals a stylish and modern retreat you are sure to fall in love with. Spanning more than 6,600 square feet of indoor living and outdoor covered space, the estate blends warmth, elegance

Shane Croft COLDWELL BANKER RESIDENTIAL RE

5199 Latrobe Dr, Windermere, FL 34786
/2
$455,000 Sold Jun 25, 2025
- 2,001 Sq Ft
- $227/SF
- 86 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2019
13727 Bressler Alley, Windermere, FL 34786

Price Improvement! Now Listed at $458,500 – Turnkey Townhome in the Vineyards of Horizon West!Welcome to 13727 Bressler Alley, a beautifully upgraded townhome in the highly desirable Vineyards of Horizon West community in Windermere, FL. This meticulously maintained home combines modern luxury with functionality, offering an ideal living space in one of Central Florida’s most sought-after

Nicholas Vaseloff REAL BROKER, LLC

13727 Bressler Alley, Windermere, FL 34786

/52
Est $727,262 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,943 Sq Ft
12961 Holdenbury Ln, Windermere, FL 34786

12961 Holdenbury Ln, Windermere, FL 34786

/26
$1,000,000
- Land
- 0.5 Acre
- $2,000,000 per Acre
2504 Windermere Reserve Ct, Windermere, FL 34786

Final Opportunity – Last Lot Available in The Reserve at Windermere! Build your dream home in the exclusive community of The Reserve at Windermere with acclaimed custom builder Element Home Builders. This final remaining homesite of 8 offers a rare opportunity to craft a one-of-a-kind luxury residence in one of Central Florida’s most prestigious neighborhoods. Surrounded by the natural beauty of

Carolina Dumit CORCORAN PREMIER REALTY

2504 Windermere Reserve Ct, Windermere, FL 34786
/2
$2,500,000 Sold Jun 25, 2025
- 5,118 Sq Ft
- $488/SF
- 119 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2001
8148 Tibet Butler Dr, Windermere, FL 34786

Keene’s Pointe – exclusive 24-hour gated/attended community in highly desired Windermere, Florida. This stunning FULLY REMODELED overlooks the third green/fourth tee box of The Golden Bear Club, an 18 hole golf course designed by Jack Nicklaus featuring golf, tennis, fitness, dining and swimming, with beautiful pond and lake views. The entire home boasts hardwood flooring, designer touches,

Teresa Stewart SOUTHERN REALTY GROUP LLC

8148 Tibet Butler Dr, Windermere, FL 34786

/21
Est $512,141 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,222 Sq Ft
11019 Bagley Alley, Windermere, FL 34786

11019 Bagley Alley, Windermere, FL 34786

/100
$929,999
- 5 Beds
- 4.5 Baths
- 3,615 Sq Ft
9257 Outlook Rock Trail, Windermere, FL 34786

MOTIVATED SELLER!! Stunning 5-Bedroom, 4.5-Bathroom Home in the Highly Desirable Windermere Trails CommunityThis luxurious and spacious residence is located in one of Windermere’s most privileged and sought-after areas. It features open-concept living spaces, a gourmet kitchen with premium finishes, and a beautiful and cozy primary suite with a spa-style bathroom and a large walk-in

Macarena Jimenez ZARIA REALTY GROUP LLC

9257 Outlook Rock Trail, Windermere, FL 34786
/2
$1,685,250 Sold Jun 25, 2025
- Land
- 5.55 Acres
- $303,649 per Acre
- 214 Days On Market
10988 Down Park Ln, Windermere, FL 34786

Prime Residential Vacant Land on Lake Down, Windermere, Florida. Nestled in the desirable enclave of Windermere, Florida, awaits a rareopportunity to claim your slice of paradise. Presenting a newly, unanimously approved by the Town of Windermere, lakefront lot of residentialvacant land spanning a generous 5.55 acres, this property boasts unparalleled potential for crafting your dream

Alexis Anderson REGENCY REAL ESTATE LLC

10988 Down Park Ln, Windermere, FL 34786

/20
Est $788,988 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,677 Sq Ft
11722 Gray Rock Trail, Windermere, FL 34786

11722 Gray Rock Trail, Windermere, FL 34786

/96
$670,000
- 4 Beds
- 3.5 Baths
- 2,827 Sq Ft
13055 Overstreet Rd, Windermere, FL 34786

Prime Location – Resort-Style Living!Perfectly situated just minutes from Orlando’s world-famous attractions and vibrant downtown, this spacious 4-bedroom, 3.5-bath home offers unbeatable convenience with schools, shopping, dining, and major roadways all close by. Inside, enjoy a private living room, formal dining room, butler’s pantry, a dedicated office, and a large kitchen that opens to a

Luis Garcia HOMELUI REALTY

13055 Overstreet Rd, Windermere, FL 34786
/2
$320,000 Sold Jun 24, 2025
- 1,442 Sq Ft
- $222/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
8168 Boat Hook Loop Unit 201/718, Windermere, FL 34786

**Video Tour Available** Welcome to Lakeside Condos at Lakes of Windermere! Enjoy RESORT-STYLE AMENITIES in an unbeatable A+ location. Residents have access to a community pool, fitness center with kid’s room, clubhouse with billiards, beach volleyball, outdoor fireplace and BBQ areas, plus access to Lake Burden's tennis courts, playground, and fishing dock. This neighborhood ties to HIGHLY

Tennille Biggers KELLER WILLIAMS ELITE PARTNERS III REALTY

8168 Boat Hook Loop Unit 201/718, Windermere, FL 34786

/45
Est $827,972 Not Listed For Sale
- 5 Beds
- 4.5 Baths
- 3,680 Sq Ft
7016 Kiwano Way, Windermere, FL 34786

7016 Kiwano Way, Windermere, FL 34786

/45
$979,000 Open Sat 12PM - 2PM
- 3 Beds
- 2 Baths
- 2,272 Sq Ft
111 Main St, Windermere, FL 34786

Prime Windermere Location! Fully Renovated and Move-In Ready!Don’t miss this beautifully updated 3-bedroom, 2-bath home nestled in the heart of Windermere. Situated on an oversized, fully fenced lot, this property offers spacious living with two cozy fireplaces and generously sized rooms—perfect for comfortable family living and entertaining.Recent Upgrades Include: Fresh interior and

Sammy Nakhleh SUNDIAL REAL ESTATE LLC

111 Main St, Windermere, FL 34786
/2
$708,000 Sold Jun 24, 2025
- 2,585 Sq Ft
- $274/SF
- 10 Days On Market
- 4 Beds
- 3 Baths
- Built 2002
1448 Glenwick Dr, Windermere, FL 34786

Welcome to your dream home in the highly sought-after Reserve at Belmere—a 24/7 guard-gated community located in beautiful Windermere, Florida. This stunning neighborhood features two picturesque lakes, scenic walking paths, and unforgettable sunsets over Lake Whitney. Stay active with resort-style amenities including a lakeview fitness center, tennis, basketball, volleyball courts, a playground,

Jose Fleming PREFERRED REAL ESTATE BROKERS

1448 Glenwick Dr, Windermere, FL 34786

/25
Est $390,049 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,028 Sq Ft
14343 Oasis Cove Blvd Unit 2002, Windermere, FL 34786

14343 Oasis Cove Blvd Unit 2002, Windermere, FL 34786

/42
$1,359,000
- 4 Beds
- 3 Baths
- 3,014 Sq Ft
11721 Camden Park Dr, Windermere, FL 34786

11721 Camden Park Drive | Keene’s PointeWelcome to a home where every detail has been lovingly renewed for both beauty and peace of mind. Tucked within the guard-gated sanctuary of Keene’s Pointe, this 4-bedroom, 3-bath residence has been completely reimagined in 2024, blending the confidence of thoughtful upgrades with the grace of timeless design.From the moment you arrive, you’ll sense

Shelley Dawson RE/MAX PRIME PROPERTIES

11721 Camden Park Dr, Windermere, FL 34786
/2
$490,000 Sold Jun 23, 2025
- 1,852 Sq Ft
- $265/SF
- 17 Days On Market
- 3 Beds
- 2 Baths
- Built 2006
7201 Halton Ct, Windermere, FL 34786

Welcome to 7201 Halton, a beautiful and move-in-ready 3-bedroom, 2-bathroom home located in the heart of Windermere. This home has a great layout, a fantastic location, and recent updates that give you peace of mind—the roof is only two years old, and the A/C system is five years old, so the big things are already taken care of.Inside, you’ll find a spacious and open floor plan with high ceilings

Shawn McCormick ERA GRIZZARD REAL ESTATE

7201 Halton Ct, Windermere, FL 34786

/15
Est $378,226 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,046 Sq Ft
Unlisted Address

Unlisted Address

/31
$1,630,000
- 3 Beds
- 2 Baths
- 2,238 Sq Ft
11923 Lake Butler Blvd, Windermere, FL 34786

Nestled on one of Windermere’s most desirable streets, this charming home offers a rare opportunity to enjoy small-town living on a beautifully wooded one-acre lot. The property features a welcoming covered entry with double doors that open into a light-filled foyer and spacious family room with soaring vaulted ceilings and a cozy wood-burning fireplace. The open-concept kitchen includes a large

Michael Julian JULIAN PROPERTIES, INC.

11923 Lake Butler Blvd, Windermere, FL 34786
/2
$720,000 Sold Jun 23, 2025
- 3,239 Sq Ft
- $222/SF
- 69 Days On Market
- 4 Beds
- 4 Baths
- Built 2016
9227 Outlook Rock Trail, Windermere, FL 34786

Beautiful home in Windermere Trails, where luxury and convenience come together in the heart of one of Central Florida's most desirable communities. This stunning 4-bedroom, 4-bathroom home is ideally situated just a short stroll from Lakeside Village Center, offering easy access to Publix, charming local restaurants, and boutique shops. Perfectly zoned for top-rated Windermere schools, including

Steve Healy CORCORAN PREMIER REALTY

9227 Outlook Rock Trail, Windermere, FL 34786

/51
Est $388,491 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,852 Sq Ft
8212 Tranquility Way Unit 3008, Windermere, FL 34786

8212 Tranquility Way Unit 3008, Windermere, FL 34786

/54
$895,000
- 5 Beds
- 4 Baths
- 3,151 Sq Ft
1638 Whitney Isles Dr, Windermere, FL 34786

Welcome to luxury living in the highly desirable gated community of Belmere, located in Windermere. This beautifully upgraded 5 bedroom, 4 bath pool home offers the perfect blend of elegance, comfort, and functionality. Featuring new luxury vinyl flooring, upgraded appliances, and an open concept split floor plan, the home is flooded with natural light that enhances its spacious and inviting

Morgan Horsley THE REAL ESTATE COLLECTION LLC

1638 Whitney Isles Dr, Windermere, FL 34786
/2
$1,020,000 Sold Jun 23, 2025
- 3,372 Sq Ft
- $302/SF
- 19 Days On Market
- 5 Beds
- 5 Baths
- Built 1990
2140 Lilypad Ln, Windermere, FL 34786

Welcome to 2140 Lilypad Lane, a rare opportunity to own an impeccably maintained, estate home in the Willows at Lake Rhea. Nestled in a private cul-de-sac on over half an acre, this single-story home offers space and privacy. With over 3,300 square feet, this home features 5 bedrooms, 3 full bathrooms, 2 half bathroom, a large bonus room, and a private screened-in pool. As you step through the

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

2140 Lilypad Ln, Windermere, FL 34786

/28
Est $436,536 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,760 Sq Ft
11819 Vermillion Ave, Windermere, FL 34786

11819 Vermillion Ave, Windermere, FL 34786

/27
$386,000
- 3 Beds
- 2.5 Baths
- 1,786 Sq Ft
14025 Oasis Springs Ln Unit 901, Windermere, FL 34786

***3D Tour on Virtual Tour Link 1*** This immaculately kept, gated end unit townhome boasts 3 bedrooms and 2.5 bathrooms. Step inside to discover a spacious layout seamlessly connecting the kitchen to the family room. The kitchen shines with stainless steel appliances, elegant wood cabinetry, and a convenient breakfast bar. Upstairs, the master suite awaits with a walk-in closet, double vanity,

Jorge Martinez, Jr KELLER WILLIAMS CLASSIC

14025 Oasis Springs Ln Unit 901, Windermere, FL 34786
/2
$1,450,000 Sold Jun 20, 2025
- 2,996 Sq Ft
- $484/SF
- 11 Days On Market
- 4 Beds
- 3 Baths
- Built 1999
5950 Blakeford Dr, Windermere, FL 34786

Welcome to the exclusive gated golf community, Keene’s Pointe! Overlooking the fairway of Hole 11 at the Golden Bear Golf Club, this 4 bed/3 bath immaculate home has gone through extensive renovation totaling over $450,000 in the past 4 years. The open floor plan accentuates the custom outdoor space including a full outdoor kitchen with gas grill, griddle top, refrigerator, and duel

Jared Jones REVEL REALTY LLC

5950 Blakeford Dr, Windermere, FL 34786

/2
Est $680,780 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,895 Sq Ft
7985 Brofield Ave, Windermere, FL 34786

7985 Brofield Ave, Windermere, FL 34786

/70
$6,800,000
- 5 Beds
- 5.5 Baths
- 6,257 Sq Ft
9259 Tibet Pointe Cir, Windermere, FL 34786

Welcome to 9259 Tibet Pointe Circle, an extraordinary lakefront residence nestled within the highly sought after guard-gated community of Keene’s Pointe. Completely renovated in 2025, this exquisite home combines timeless elegance with modern luxury, offering breathtaking views and direct frontage on the pristine waters of Lake Tibet. This meticulously updated estate showcases high-end finishes

Teresa Stewart SOUTHERN REALTY GROUP LLC

9259 Tibet Pointe Cir, Windermere, FL 34786
/2
$475,000 Sold Jun 20, 2025
- 1,742 Sq Ft
- $273/SF
- 4 Days On Market
- 3 Beds
- 2 Baths
- Built 2012
12691 Calderdale Ave, Windermere, FL 34786

FANTASTIC PARK VIEW SINGLE STORY WINDERMERE HOME IN DESIRABLE WICKHAM PARK! Maintenance free Florida living at its best as HOA covers exterior home maintenance, roof, ground keeping and much more! This is the popular Ashton Woods Lancaster model featuring a great bright, open and airy split floor plan. The expansive Kitchen/Dining/family room combo opens perfectly to the rear covered lanai and

Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

12691 Calderdale Ave, Windermere, FL 34786

/16
Est $330,110 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
8156 Boat Hook Loop Unit 308, Windermere, FL 34786

8156 Boat Hook Loop Unit 308, Windermere, FL 34786

/58
$1,225,000
- 4 Beds
- 3.5 Baths
- 3,419 Sq Ft
11707 Hampstead St, Windermere, FL 34786

Welcome to this stunning Thoreau floor plan by Meritage Homes, nestled in The Enclave in the heart of Windermere—one of Central Florida’s most desirable areas. This expansive 3,500 sq ft residence offers 4 bedrooms, 3 full bathrooms, a dedicated half pool bath, a downstairs den serving as an office and an upstairs oversized media room that could easily serve as a fifth bedroom. From the moment

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

11707 Hampstead St, Windermere, FL 34786
/2
$855,000 Sold Jun 20, 2025
- 2,823 Sq Ft
- $303/SF
- 33 Days On Market
- 4 Beds
- 3 Baths
- Built 2021
9248 Legado Dr, Windermere, FL 34786

WOW! Don’t miss this stunning 4 bedroom / 3 bathroom home tucked away on a quiet cul-de-sac with no rear neighbors and incredible fireworks views! This beautifully maintained Windermere home in the Legado neighborhood offers the perfect blend of comfort, privacy, and entertainment-ready features. From the moment you step inside, you’ll feel welcomed by the warm and open layout, complete with a

Ken Pozek KELLER WILLIAMS ELITE PARTNERS III REALTY

9248 Legado Dr, Windermere, FL 34786

/44
Est $390,233 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,840 Sq Ft
14241 Desert Haven St Unit 3501, Windermere, FL 34786

14241 Desert Haven St Unit 3501, Windermere, FL 34786

/31
$589,000
- 3 Beds
- 2.5 Baths
- 1,925 Sq Ft
11316 Rapallo Ln, Windermere, FL 34786

PRICE IMPROVEMENT!! Discover the allure of this beautiful Mediterranean-style residence located in Windermere's highly sought-after gated Belmere Community. This 3 Bedroom,2.5 bath home offers a spacious split floor plan featuring formal living and dining rooms, along with an open-concept kitchen and family room. The expansive screened patio is ideal for outdoor living and entertaining. A

Sherry Hutchins PREMIUM REALTY ADVISORS LLC

11316 Rapallo Ln, Windermere, FL 34786
/2
$2,160,000 Sold Jun 19, 2025
- 5,030 Sq Ft
- $429/SF
- 231 Days On Market
- 6 Beds
- 5 Baths
- Built 2004
11227 Macaw Ct, Windermere, FL 34786

This amazing residence in Keene’s Pointe overlooking the picturesque 4th fairway of the Golden Bear Club has everything you could want or need in a custom home. This flexible floorpan allows the home to be a 6 bedroom with an office, or a 5 bedroom home with two offices. And even beyond that flexibility, you do have 5 full bathrooms, an upstairs suite that is like its own apartment with bedroom,

Shane Croft COLDWELL BANKER RESIDENTIAL RE

11227 Macaw Ct, Windermere, FL 34786

/50
Est $666,623 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,203 Sq Ft
9283 Patrimonio Loop, Windermere, FL 34786

9283 Patrimonio Loop, Windermere, FL 34786

/37
$1,895,000
- 5 Beds
- 4.5 Baths
- 5,704 Sq Ft
6161 Blakeford Dr, Windermere, FL 34786

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. $50K SELLER CREDIT FOR IMPROVEMENTS!!! Currently the LOWEST PRICE per sq ft in Keene’s Pointe for sale this home screams VALUE!!! This 5BR/4.5BA Goehring & Morgan estate blends timeless craftsmanship with resort-style living in one of Central Florida’s most prestigious guard-gated communities. Features

Pat Hancock THOMAS LYNNE REALTY GROUP LLC

6161 Blakeford Dr, Windermere, FL 34786
/2
$418,000 Sold Jun 18, 2025
- 1,588 Sq Ft
- $263/SF
- 10 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2016
11746 Water Run Alley, Windermere, FL 34786

Welcome to this modern townhouse designed for luxurious living in the heart of Windermere’s sought-after Ashlin Park community!This 3-bedroom, 2.5-bathroom home offers 1,588 sq ft of thoughtfully designed space, with top-of-the-line ceramic tiles on the first floor, an open-concept floor plan, and subway tile accents in the chef-inspired kitchen. The oversized quartz kitchen island is perfect for

Kris Ibrahim HOME WISE REALTY GROUP, INC.

11746 Water Run Alley, Windermere, FL 34786

/64
Est $699,757 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 3,009 Sq Ft
6704 Bridgewater Village Rd, Windermere, FL 34786

6704 Bridgewater Village Rd, Windermere, FL 34786

/99
$3,200,000
- 5 Beds
- 8 Baths
- 6,753 Sq Ft
4071 Isabella Cir, Windermere, FL 34786

Welcome to Casabella at Windermere, a beautiful gated community where luxury and elegance converge. This stunning 6-bedroom, 5.5-bath estate sits on a sprawling one-acre lot and showcases refined architectural details, soaring ceilings, expansive windows, and light-filled open spaces designed for both grand entertaining and everyday comfort. The resort-style backyard is a private oasis, featuring

Noor Masri LA ROSA REALTY PREMIER LLC

4071 Isabella Cir, Windermere, FL 34786

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