Windermere, FL Homes

/37
$622,000
- 4 Beds
- 2.5 Baths
- 2,981 Sq Ft
12925 Holdenbury Ln, Windermere, FL 34786

This splendid two-story home features four large bedrooms and 2.5 bathrooms. The true highlight of the home is its stunning, oversized kitchen, which has a huge amount of cabinet and counter space. Not one, but two islands provide a setting for casual dining and culinary creativity. The main floor offers a cozy first-floor bedroom for added convenience and flexibility, suitable for guests or as a

Eric Nelson SIGNATURE HOMES

12925 Holdenbury Ln, Windermere, FL 34786
/26
$2,900 per month
- 3 Beds
- 2 Baths
- 2,088 Sq Ft
- House for Rent
6728 Duncaster St, Windermere, FL 34786

Welcome to your new home in the desirable Lakes of Windermere community. This beautiful 3-bedroom, 2-bathroom house includes a large private office that can be easily converted into a 4th bedroom. It boasts a covered screened lanai and a 2-car garage. Freshly painted inside and out, with a new roof, sod, and landscaping in the front yard, this home is move-in ready. All three bedrooms have new

Steve Gayle SOUTHEASTERN REAL ESTATE SERV

6728 Duncaster St, Windermere, FL 34786
/2
$4,125,000 Sold Sep 05, 2025
- 4,783 Sq Ft
- $862/SF
- 103 Days On Market
- 5 Beds
- 6 Baths
- Built 1999
805 W 2nd Ave, Windermere, FL 34786

Welcome to perhaps the best outdoor location on the entire Butler Chain with a nearly 300 square-foot-enclosed boathouse, custom beach and a fully landscaped yard with plenty of space and enhancements for entertainment. The outside space includes hot tubs, 170 square-foot outdoor gym, uniquely designed pool with back of the home built around it, over 100+ outdoor lights (multiple underwater

Nick Cotton FOREVER MAGIC REALTY INC

805 W 2nd Ave, Windermere, FL 34786

/2
Est $506,949 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,984 Sq Ft
6315 Golden Dewdrop Trail, Windermere, FL 34786

6315 Golden Dewdrop Trail, Windermere, FL 34786

/36
$790,000
- 4 Beds
- 3 Baths
- 2,622 Sq Ft
11450 Arborside Bend Way, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to this well-maintained 4-bedroom, 3-bathroom home located in the gated community of Glenmuir. This traditional-layout residence offers a blend of classic elegance and modern comfort. Step inside to discover beautiful hardwood and tile flooring that flows seamlessly throughout the home.The heart of this home is its inviting living

John Callahan REDFIN CORPORATION

11450 Arborside Bend Way, Windermere, FL 34786
/17
$2,995 per month
- 4 Beds
- 3 Baths
- 2,925 Sq Ft
- House for Rent
12951 Overstreet Rd, Windermere, FL 34786

Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.This home features Progress Smart Home - Progress Residential's smart home app, which allows you to control the home securely from any of your devices. Learn more at Coming soon! This home is

12951 Overstreet Rd, Windermere, FL 34786
/45
$900,000 Sold Sep 05, 2025
- 2,868 Sq Ft
- $314/SF
- 104 Days On Market
- 4 Beds
- 3.5 Baths
- Built 2000
6125 Foxfield Ct, Windermere, FL 34786

Popular Keene's Pointe in Windermere! 24 Hour attendant gated community. Located on the 1st Fairway, this beautiful 4 Bedroom, 3 1/2 Baths Villa Style home will not disappoint. Primary Bedroom with a expansive bathroom, along with 2 other bedrooms with en-suite baths are all located on the 1st floor. 1 Bedroom with 1/2 bath upstairs. Large open Dinng and Living Room overlook the screened

Mary Ann Thompson RE/MAX Solutions

6125 Foxfield Ct, Windermere, FL 34786

/8
Est $749,299 Not Listed For Sale
1330 Lake Olivia Ln, Windermere, FL 34786

1330 Lake Olivia Ln, Windermere, FL 34786

/53
$660,000
- 4 Beds
- 2 Baths
- 2,555 Sq Ft
6139 Andreozzi Ln, Windermere, FL 34786

Here is your chance to own this spacious well-maintained one-story 4-bedroom waterfront home on a pond located in the desirable Providence neighborhood of Windermere. As you enter through the front porch and foyer you will immediately notice the high 10’ ceilings and inviting rooms to your well-thought-out floor plan. The living room is spacious with an elegant dining room overlooking the

Simon Simaan THE SIMON SIMAAN GROUP

6139 Andreozzi Ln, Windermere, FL 34786
/29
$2,900 per month
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
- House for Rent
11649 Black Rail St, Windermere, FL 34786

Spacious 3-bedroom, 2.5-bath townhome located in the heart of Windermere with 2,139 sq. ft. of open living space. The gourmet kitchen features a large island, perfect for entertaining, while the upstairs includes a convenient laundry room. Enjoy a private fenced backyard with a cozy patio, plus a 2-car covered garage in the rear. One of the top benefits of living in Windermere is access to highly

Vicente Virgilio ALTIS REALTY

11649 Black Rail St, Windermere, FL 34786
/2
$6,800,000 Sold Sep 05, 2025
- 8,691 Sq Ft
- $782/SF
- 141 Days On Market
- 5 Beds
- 6.5 Baths
- Built 2002
6126 Kirkstone Ln, Windermere, FL 34786

Nestled within the highly sought after, guard-gated community of Lake Butler Sound, this breathtaking lakefront estate has been completely remodeled with designer interior and exterior finishes, offering an unparalleled blend of sophistication and modern luxury. Positioned on an expansive corner lot, this home boasts breathtaking panoramic lake views from nearly every room, creating a serene and

Christopher Christensen COMPASS FLORIDA LLC

6126 Kirkstone Ln, Windermere, FL 34786

/2
Est $3,241,995 Not Listed For Sale
- 6 Beds
- 8 Baths
- 6,842 Sq Ft
4124 Isabella Cir, Windermere, FL 34786

4124 Isabella Cir, Windermere, FL 34786

/43
$949,500
- 5 Beds
- 5 Baths
- 3,285 Sq Ft
11096 Ledgement Ln, Windermere, FL 34786

This Windermere home proliferates in privacy, luxury, and modernconvenience. Tucked away on a third of an acre within the gated Glenmuircommunity and backing onto a protected conservation area, this stunninghome presents tranquil forested views and absolute peace with no rearneighbors, ever. The saltwater pool, complete with solar heating, child-safe fencing, LEDaccent

James Ellis CHARLES RUTENBERG REALTY ORLANDO

11096 Ledgement Ln, Windermere, FL 34786
/17
$3,185 per month
- 4 Beds
- 4 Baths
- 2,702 Sq Ft
- House for Rent
1456 Whitney Isles Dr, Windermere, FL 34786

Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3329.90. That covers your base rent, $3185.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

1456 Whitney Isles Dr, Windermere, FL 34786
/2
$8,500,000 Sold Sep 05, 2025
- 11,403 Sq Ft
- $745/SF
- 206 Days On Market
- 7 Beds
- 13 Baths
- Built 2013
5271 Isleworth Country Club Dr, Windermere, FL 34786

Welcome to this grand residence nestled on a sprawling 1.17 acre lot originally hand selected by golf legend Arnold Palmer. Perfectly positioned to capture breathtaking views of the first and tenth holes, this remarkable estate provides a lifestyle of unmatched elegance and comfort.Meticulously maintained, this grand estate encompasses 11,403 square feet of living space thoughtfully

Monica Lochmandy ISLEWORTH REALTY LLC

5271 Isleworth Country Club Dr, Windermere, FL 34786

/43
Est $531,629 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,139 Sq Ft
11650 Black Rail St, Windermere, FL 34786

11650 Black Rail St, Windermere, FL 34786

/40
$539,900
- 3 Beds
- 2.5 Baths
- 2,154 Sq Ft
8575 Lookout Pointe Dr, Windermere, FL 34786

This beautiful 3 bedroom, 2.5 bath home is nestled in the highly desirable Windermere Trails community. Enjoy the magic of theme parks just minutes away from Disney World with a direct view of the fireworks from your front porch! With over 2,000 SqFt, this home boasts an open floor plan that offers an upgraded kitchen, a large dining space, a spacious family room, and an upstairs loft. The

Thomas Weclew THE REALTY MEDICS

8575 Lookout Pointe Dr, Windermere, FL 34786
/24
$2,800 per month
- 4 Beds
- 2.5 Baths
- 2,024 Sq Ft
- House for Rent
13772 Summerport Trail Loop, Windermere, FL 34786

NO CARPET! This spacious and well-maintained home is nestled in the desirable Summerport community, offering a perfect blend of comfort and convenience. Close to top-rated schools, shopping, and major attractions (like Disney!), this is ideal for families or professionals. Home Features: 4 bedrooms & 2.5 bathrooms Plenty of space for everyone. 2,233 sq. ft. of thoughtfully designed living

Yukey Hoo U KEY REALTY

13772 Summerport Trail Loop, Windermere, FL 34786
/2
$2,400,000 Sold Sep 05, 2025
- 5,111 Sq Ft
- $470/SF
- 708 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1993
800 W 2nd Ave, Windermere, FL 34786

Detached Guest Suite overlooking Pool with Fireplace has Private Entrance in Courtyard - Courtyard Pool with Waterfall from the Heated Spa has the feel of an Olde World European Resort - Formal Living Room with Fireplace - Formal Dining Room with Fireplace - Family Room with Fireplace - Large Kitchen with Wine Cellar and Pantry in the Heart of the Home has incredible views of the Pool & Lake -

Darrell Nunnelley VINTAGE REALTY GROUP LLC

800 W 2nd Ave, Windermere, FL 34786

/59
Est $2,686,698 Not Listed For Sale
- 6 Beds
- 8 Baths
- 6,803 Sq Ft
13340 Bellaria Cir, Windermere, FL 34786

13340 Bellaria Cir, Windermere, FL 34786

/64
$1,300,000
- 4 Beds
- 3.5 Baths
- 2,791 Sq Ft
109 E 12th Ave, Windermere, FL 34786

Modern upgrades meet timeless Windermere charm in this fully reimagined four-bedroom, three-and-a-half-bath home, just steps from Lake Bessie. Set on a beautifully manicured corner lot with no HOA, this thoughtfully updated property blends luxury, comfort, and functionality in one of Central Florida’s most desirable communities.Every detail has been considered—NEW ROOF, NEW A/C, NEW

Robert Larkan EXECUTIVE PROPERTIES

109 E 12th Ave, Windermere, FL 34786
/18
$2,500 per month
- 3 Beds
- 2.5 Baths
- 1,480 Sq Ft
- Townhouse for Rent
7712 Rigby St, Windermere, FL 34786

Move-in ready and impeccably maintained, this spacious 3-bedroom, 2.5-bath townhome with a 2-car detached garage is located in the highly sought-after Wickham Park community.Inside, the gourmet kitchen boasts a large island with breakfast bar, granite countertops, 42" cabinets with crown molding, and all stainless steel appliances—perfect for both everyday living and entertaining. The

7712 Rigby St, Windermere, FL 34786
/2
$1,750,000 Sold Sep 04, 2025
- 5,284 Sq Ft
- $331/SF
- 2 Days On Market
- 6 Beds
- 4.5 Baths
- Built 2004
5137 Tildens Grove Blvd, Windermere, FL 34786

Discover refined luxury in the guard-gated Tildens Grove community. This custom-built, traditional-style residence spans approximately 5,300 sqft across a prime .64 acre lot backing to a serene conservation pond. Boasting 6 bedrooms and 41⁄2 baths, the home offers exceptional craftsmanship and thoughtful updates throughout. The gourmet kitchen is a chef’s dream—featuring a large center island,

Laura Senzamici ENGEL & VOLKERS ORLANDO DR PHILLIPS

5137 Tildens Grove Blvd, Windermere, FL 34786

/64
Est $788,919 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,694 Sq Ft
12851 Westside Village Loop, Windermere, FL 34786

12851 Westside Village Loop, Windermere, FL 34786

/42
$585,000
- 4 Beds
- 2 Baths
- 2,159 Sq Ft
11322 Rapallo Ln, Windermere, FL 34786

One or more photo(s) has been virtually staged. ***Back on Market due to Buyer not depositing Escrow*** “Mortgage savings may be available for buyers of this listing.” Located in the gated Windermere community of Belmere Village, this beautifully maintained 4-bedroom, 2-bathroom home offers both comfort and convenience. Residents enjoy low HOA fees and a wealth of amenities including a clubhouse,

John Callahan REDFIN CORPORATION

11322 Rapallo Ln, Windermere, FL 34786
/12
$2,900 per month
- 4 Beds
- 2.5 Baths
- 2,460 Sq Ft
- House for Rent
12647 Arley Dr, Windermere, FL 34786

Welcome to Lakes of Windermere. This spacious executive four-bedroom, two-and-a-half-bath home is in a great location. The home features a new roof replaced in May 2025, and a new HVAC system installed in June 2025, whilst the exterior is scheduled to be painted. The property has been decorated and is ready for occupancy, except for carpets, which will be steam cleaned before move-in. Call to

Susan Cook CENTURY 21 CARIOTI

12647 Arley Dr, Windermere, FL 34786
/2
$535,000 Sold Sep 04, 2025
- 2,230 Sq Ft
- $240/SF
- 25 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2005
6830 Mapperton Dr, Windermere, FL 34786

Wow, what a wonderful home to return to everyday that has Beautiful Views of the Pine Tree Forest located across the street. Enjoy sipping lemonade on your Front Porch with this Unobstructed View of Nature! Once inside you will be greeted by the Vibrant Colors throughout and an Abundance of Large Windows making this home Light and Bright. The split bedroom feature is ideal. With 2 bedrooms

Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

6830 Mapperton Dr, Windermere, FL 34786

/36
Est $460,686 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,769 Sq Ft
6506 Stoller Ave, Windermere, FL 34786

6506 Stoller Ave, Windermere, FL 34786

/100
$3,250,000
- 4 Beds
- 5.5 Baths
- 4,849 Sq Ft
6186 Louise Cove Dr, Windermere, FL 34786

A Masterpiece of Design in Isleworth – 6186 Louise Cove Drive. Stunning, design magazine-worthy residence nestled behind the exclusive 24-hour guard-gated community of Isleworth, one of Central Florida’s most prestigious neighborhoods. This exquisite estate sits on a spacious 0.75-acre corner lot, surrounded by mature landscaping and a stately circular driveway that sets the tone for the luxury

Simon Simaan THE SIMON SIMAAN GROUP

6186 Louise Cove Dr, Windermere, FL 34786
/20
$2,200 per month
- 3 Beds
- 2 Baths
- 1,442 Sq Ft
- Condo for Rent
8179 Maritime Flag St Unit 202, Windermere, FL 34786

Property Id: 453862Beautiful Lakeside at Lakes of Windermere 3 bedroom / 2 bath condo with open floor plan, large master walk-in closet, crown molding, 1st floor corner unit with, private screened lanai. Newly renovated condo with fresh paint, upgraded kitchen with premium quartz counter top, stainless steel appliances, upgraded bathrooms, upgraded premium flooring and NEW Samsung Washer

8179 Maritime Flag St Unit 202, Windermere, FL 34786
/2
$450,000 Sold Sep 04, 2025
- 1,904 Sq Ft
- $236/SF
- 74 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2018
11037 Bagley Alley, Windermere, FL 34786

Welcome to this 3bedroom, 2.5 bathroom, two-story home in the community of Westside Village in Windemere . This home features an open concept with a living, kitchen, and dining room. The kitchen boasts granite countertops, stainless steel appliances, backsplash, 42" upper cabinets, and a breakfast bar. The second floor features a spacious primary bedroom and a private bathroom with double vanity

Eric Jia NUMBER 1 BROKER, LLC

11037 Bagley Alley, Windermere, FL 34786

/56
Est $2,442,879 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,524 Sq Ft
13352 Bellaria Cir, Windermere, FL 34786

13352 Bellaria Cir, Windermere, FL 34786

/51
$745,000
- 4 Beds
- 3.5 Baths
- 2,745 Sq Ft
13519 Bicton Ln, Windermere, FL 34786

Live Just Minutes from the Magic – Stunning 4-Bedroom Home in Gated Windermere Community. Welcome to 13519 Bicton Dr, a beautifully maintained 4-bedroom, 3.5-bathroom home offering nearly 3,000 square feet of thoughtfully designed living space with countless upgrades in one of Windermere's most sought-after gated communities. With a 3-car garage, a new roof, and new windows, this home combines

Tiphany Weeks DIAMOND REAL ESTATE GROUP

13519 Bicton Ln, Windermere, FL 34786
/15
$2,800 per month
- 4 Beds
- 2.5 Baths
- 2,068 Sq Ft
- House for Rent
12058 Silverlake Park Dr, Windermere, FL 34786

Welcome to this beautiful 4 bedrooms and 2.5 bedrooms home. The main level features a bright and welcoming living room, a formal dining area, and a stylish kitchen with stainless steel appliances and plenty of counter space—perfect for both everyday living and entertaining. All four bedrooms are located upstairs, offering enhanced privacy and comfort. A generous loft area provides additional

Jeff Li CINO INTERNATIONAL INC

12058 Silverlake Park Dr, Windermere, FL 34786
/2
$490,000 Sold Sep 04, 2025
- 1,696 Sq Ft
- $289/SF
- 102 Days On Market
- 3 Beds
- 2 Baths
- Built 2012
12751 Calderdale Ave, Windermere, FL 34786

Beautiful home with park views offering maintenance free living with HOA dues covering roof replacement, exterior painting and front lawn/shrub maintenance. The interior has fresh paint, vinyl wood plank flooring was just installed, and the exterior has been painted recently. You'll love the open layout with a large great room opening out from the gourmet island kitchen with granite and stainless

Hojin Chang RE/MAX PRIME PROPERTIES

12751 Calderdale Ave, Windermere, FL 34786

/23
Est $461,405 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,912 Sq Ft
13736 Bravante Alley, Windermere, FL 34786

13736 Bravante Alley, Windermere, FL 34786

/40
$589,900
- 4 Beds
- 2 Baths
- 1,798 Sq Ft
9319 Woodbreeze Blvd, Windermere, FL 34786

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

Steven Looper CHARLES RUTENBERG REALTY ORLANDO

9319 Woodbreeze Blvd, Windermere, FL 34786
/20
$1,350 per month
- Studio
- 1 Bath
- 400 Sq Ft
- House for Rent
14451 Bluebird Park Rd, Windermere, FL 34786

Property Id: 1774804Discover this stunning, remodeled above-garage studio with a private, independent entrance in the peaceful and highly sought-after Summerport neighborhood of Windermere. Perfect for a single tenant, this rare gem offers high-end finishes, a spacious walk-in closet, and appliances, including a stove, fridge, 2-in-1 washer-dryer, and AC unit.Enjoy resort-style

14451 Bluebird Park Rd, Windermere, FL 34786
/2
$1,000,000 Sold Sep 03, 2025
- 3,646 Sq Ft
- $274/SF
- 64 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1989
1947 Broadleaf Ct, Windermere, FL 34786

One or more photo(s) has been virtually staged. Welcome to 1947 Broadleaf Court – a beautifully maintained 5-bedroom, 3.5-bath home located in the highly sought-after Windermere Downs community. Nestled on nearly half an acre in a peaceful cul-de-sac, this spacious 3,646 sq ft residence offers the perfect blend of comfort, elegance, and Florida lifestyle.Step inside to discover a light-filled

Kevin Sullivan LAKESIDE REALTY WINDERMERE INC

1947 Broadleaf Ct, Windermere, FL 34786

/36
Est $1,534,514 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,374 Sq Ft
1146 Estancia Woods Loop, Windermere, FL 34786

1146 Estancia Woods Loop, Windermere, FL 34786

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