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WINDERMERE 30 DAY MARKET SNAPSHOT

(JUN 09, 2026 - JUL 09, 2026)
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316 Properties

316 Properties Available

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8316 LOOKOUT POINTE DR, Windermere, FL 34786

$1,075,000

New

Single Family Home

5 Beds 4 Baths 4,332 SqFt

8316 LOOKOUT POINTE DR, Windermere, FL 34786

Located in the highly desirable Windermere Trails community, this impressive residence offers 5 bedrooms, 4 full bathroo...

Listed by Gian Balsamo LA ROSA REALTY KISSIMMEE

Stellar MLS
6119 PAYNE STEWART DR, Windermere, FL 34786
1/22 22

$15,000

New

Single Family Home

3 Beds 4 Baths 2,836 SqFt

6119 PAYNE STEWART DR, Windermere, FL 34786

Among the shores of beautiful Lake Chase within the gates of Isleworth Golf & Country Club, this modern golf villa offer...

Listed by Michelle Corbin ISLEWORTH REALTY LLC

Stellar MLS
7023 KIWANO WAY, Windermere, FL 34786
1/45 45

$4,980

New

Single Family Home

5 Beds 5 Baths 3,136 SqFt

7023 KIWANO WAY, Windermere, FL 34786

Welcome to this beautiful, spacious two-story home located in the highly sought-after Sanctuary at Lakes of Windermere. ...

Listed by Wendy Fischer PREMIER SOTHEBYS INT'L REALTY

Stellar MLS
7516 BENTONSHIRE AVE, Windermere, FL 34786
1/18 18

$2,400

New

Townhouse

2 Beds 3 Baths 1,250 SqFt

7516 BENTONSHIRE AVE, Windermere, FL 34786

Welcome to this beautifully maintained 2-bedroom, 2.5-bathroom townhome located in the highly desirable Wickham Park com...

Listed by Bekah Burke BELLA TRAE REALTY

Stellar MLS
8764 POWDER RIDGE TRL, Windermere, FL 34786
1/43 43

$4,750

New

Single Family Home

4 Beds 4 Baths 3,144 SqFt

8764 POWDER RIDGE TRL, Windermere, FL 34786

LOCATION!! LOCATION!!! This stunning house has a large kitchen with a large central island, with quartz and also has a ...

Listed by Gilson Rodrigues KARDOSH REALTY

Stellar MLS
11564 MIZZON DR #102, Windermere, FL 34786
3D

$295,000

New

Condo

2 Beds 2 Baths 1,161 SqFt

11564 MIZZON DR #102, Windermere, FL 34786

**Windermere Renovated First-Floor Condo | Resort-Style Amenities | Minutes from Disney & Winter Garden Village** <br> <...

Listed by Jose Rojo URBAN-O REAL ESTATE SOLUTIONS

Stellar MLS
7231 SANGALLA DR, Windermere, FL 34786
1/58 58

$1,300,000

New

Single Family Home

5 Beds 5 Baths 3,835 SqFt

7231 SANGALLA DR, Windermere, FL 34786

Tucked away within the private gates of Casa Del Lago, one of Windermere's most desirable communities, this exceptional ...

Listed by Andy Neal THE AGENCY FL

Stellar MLS
8327 BRYCE CANYON AVE, Windermere, FL 34786
1/21 21

$2,800

New

Single Family Home

4 Beds 3 Baths 2,052 SqFt

8327 BRYCE CANYON AVE, Windermere, FL 34786

Beautiful 4-bedroom, 2.5-bath two-story home situated on a desirable corner lot in a highly sought-after community. This...

Listed by Andrea Pointon POINTON REALTY INC

Stellar MLS
8342 BOYLA CT, Windermere, FL 34786
1/93 93

$6,700,000

New

Single Family Home

8 Beds 10 Baths 8,133 SqFt

8342 BOYLA CT, Windermere, FL 34786

Virtually Staged. Welcome to an extraordinary new construction waterfront estate built by Element Home Builders, located...

Listed by Simon Simaan THE SIMON SIMAAN GROUP

Stellar MLS
12210 LANGSTAFF DR, Windermere, FL 34786
1/29 29

$2,799

New

Townhouse

3 Beds 3 Baths 1,480 SqFt

12210 LANGSTAFF DR, Windermere, FL 34786

Experience comfortable living in this beautifully upgraded 3-bedroom, 2.5-bathroom townhome located in one of Windermere...

Listed by Sina Albekord CORCORAN PREMIER REALTY

Stellar MLS
2009 WOODY DR, Windermere, FL 34786
1/43 43

$1,200,000

New

Single Family Home

4 Beds 3 Baths 3,540 SqFt

2009 WOODY DR, Windermere, FL 34786

Nestled within the highly sought-after Windermere Downs community this Lake-Access Residence, sitting on .74 acres, offe...

Listed by Rebekkah Boskovich REVEL REALTY LLC

Stellar MLS
2053 WOODY DR, Windermere, FL 34786
1/49 49

$679,000

New

Single Family Home

3 Beds 3 Baths 2,177 SqFt

2053 WOODY DR, Windermere, FL 34786

Welcome to 2053 Woody Drive, where timeless Windermere charm meets modern updates. From the moment you arrive, you'll ap...

Listed by Vivian Saavedra LPT REALTY, LLC

Stellar MLS
6241 BLAKEFORD DR, Windermere, FL 34786
1/59 59

$1,795,000

New

Single Family Home

4 Beds 4 Baths 3,556 SqFt

6241 BLAKEFORD DR, Windermere, FL 34786

Something unexpected! Something unique! An amazing space! Welcome to 6241 Blakeford Drive, where the charm, character, ...

Listed by Angela Durruthy KEENE'S POINTE REALTY

Stellar MLS
7449 ELLA LN, Windermere, FL 34786
1/31 31

$2,800

New

Single Family Home

3 Beds 3 Baths 1,982 SqFt

7449 ELLA LN, Windermere, FL 34786

Move into this fabulous 2-story home. 3 bedrooms and 2.5 bathrooms. Beautiful kitchen with granite countertops, a center...

Listed by Paul Moscoso SHINING OAK REALTY

Stellar MLS
8404 IRON MOUNTAIN TRL, Windermere, FL 34786
1/36 36

$2,650

New

Townhouse

3 Beds 3 Baths 1,760 SqFt

8404 IRON MOUNTAIN TRL, Windermere, FL 34786

Virtually Staged. AMAZING 3 BEDROOM TOWNHOME AT THE BEAUTIFUL WINDERMERE TRAILS! <br>Marketing DescriptionWelcome home t...

Listed by Jacob Hara TRANSCEND REALTY

Stellar MLS
12820 STRODE LN, Windermere, FL 34786
1/28 28

$2,900

New

Townhouse

3 Beds 3 Baths 1,617 SqFt

12820 STRODE LN, Windermere, FL 34786

ONE MONTH FREE RENT! Move in by August 1st with an approved application and signed lease to receive one month free rent....

Listed by Mariana Haddad LA ROSA REALTY LLC

Stellar MLS
12912 DROXFORD RD, Windermere, FL 34786
3D

$650,000

New

Single Family Home

5 Beds 4 Baths 2,966 SqFt

12912 DROXFORD RD, Windermere, FL 34786

Welcome to this beautifully maintained two-story home in the highly sought-after Lakes of Windermere, offering 5 bedroom...

Listed by Phat Nguyen LPT REALTY, LLC

Stellar MLS
13845 BRIDGEWATER CROSSINGS BLVD, Windermere, FL 34786
1/26 26

$489,000

New

Single Family Home

3 Beds 3 Baths 1,636 SqFt

13845 BRIDGEWATER CROSSINGS BLVD, Windermere, FL 34786

Welcome to this beautifully maintained home in the highly desirable community of Summerport Trail in Windermere. This sp...

Listed by Daniel Grieb KELLER WILLIAMS REALTY AT THE PARKS

Stellar MLS
2512 TRYON PL, Windermere, FL 34786
1/69 69

$1,230,000

New

Single Family Home

4 Beds 3 Baths 3,478 SqFt

2512 TRYON PL, Windermere, FL 34786

Welcome to a rare opportunity in the highly sought-after The Manors at Butler Bay, in the heart of Windermere. This cust...

Listed by Jamie Stolinas Crame, LLC CENTURY 21 CARIOTI

Stellar MLS
7060 VENTNOR DR, Windermere, FL 34786
1/34 34

$444,900

New

Townhouse

3 Beds 3 Baths 1,642 SqFt

7060 VENTNOR DR, Windermere, FL 34786

BEST VALUE TOWNHOUSE IN WINDERMERE! OUTSTANDING HOME AND LOCATION in the desirable community of Preston Square in Winder...

Listed by Lidia Barberini AGENT TRUST REALTY CORPORATION

Stellar MLS
11446 JASPER KAY TER #103, Windermere, FL 34786
1/32 32

$330,000

New

Condo

3 Beds 2 Baths 1,442 SqFt

11446 JASPER KAY TER #103, Windermere, FL 34786

Welcome to 11446 Jasper Kay Terrace, Unit 103, a beautifully updated first-floor condominium offering comfortable, low-m...

Listed by Jay Stewart SOUTHERN REALTY GROUP LLC

Stellar MLS
13219 CHARFIELD ST, Windermere, FL 34786
3D

$565,000

New

Single Family Home

3 Beds 2 Baths 1,706 SqFt

13219 CHARFIELD ST, Windermere, FL 34786

Welcome to this charming and inviting home nestled in the highly desirable Lake Sawyer South community in Windermere. As...

Listed by Patricia Schraiber DENIZ REALTY PARTNERS LLC

Stellar MLS
8411 WOBURN CT, Windermere, FL 34786
1/30 30

$7,850

New

Single Family Home

4 Beds 3 Baths 2,562 SqFt

8411 WOBURN CT, Windermere, FL 34786

Welcome to this 4-bedroom, 3-bathroom home located on a quiet cul-de-sac in the guard-gated community of Keene's Pointe....

Listed by Jessica Cueva PA CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
11249 RAPALLO LN, Windermere, FL 34786
1/37 37

$750,000

New

Single Family Home

5 Beds 3 Baths 2,366 SqFt

11249 RAPALLO LN, Windermere, FL 34786

BRAND NEW TILE ROOF. Nestled within the prestigious gated community of Belmere in Windermere, Florida, this exceptional ...

Listed by Joseph Sipp KELLER WILLIAMS WINTER PARK

Stellar MLS
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LPT Realty

Marcus E Smith PA License ID: 3187002

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1400 S. International Pkwy Lake Mary, FL 3274

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Marcus E Smith PA License ID: 3187002

+1(407) 323-7320 marcus@marcusesmith.com

1400 S. International Pkwy Lake Mary, FL 3274

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