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WINDERMERE 30 DAY MARKET SNAPSHOT

(NOV 05, 2025 - DEC 05, 2025)
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324 Properties

324 Properties Available In 34786

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Market Insights
6615 HELMSLEY CIR, Windermere, FL 34786
1/42 42

$799,900

Active

Single Family Home

5 Beds 4 Baths 3,390 SqFt

6615 HELMSLEY CIR, Windermere, FL 34786

Beautifully remodeled and impeccably maintained, this spacious 3,390 sq. ft. two-story home offers 5 bedrooms, 3.5 bathr...

Listed by Angela Gann KELLER WILLIAMS ELITE PARTNERS III REALTY

Stellar MLS
11438 ARBORSIDE BEND WAY, Windermere, FL 34786
1/62 62

$655,000

Active

Single Family Home

4 Beds 2 Baths 2,019 SqFt

11438 ARBORSIDE BEND WAY, Windermere, FL 34786

Welcome to The Enclave at Glenmuir, one of Windermere's most exclusive GATED communities — known for its tranquility, sa...

Listed by Zoe Attwood SERHANT

Stellar MLS
11819 VERMILLION AVE, Windermere, FL 34786
1/26 26

$2,800

Active

Townhouse

3 Beds 3 Baths 1,760 SqFt

11819 VERMILLION AVE, Windermere, FL 34786

Gorgeous 3-bedroom, 2.5-bathroom Townhouse for rent with 1,760 square feet of modern elegance and thoughtful design. The...

Listed by Juan Mejia CENTENNIAL REALTY GROUP LLC

Stellar MLS
12132 MONTALCINO CIR, Windermere, FL 34786
1/91 91

$4,199,000

Active

Single Family Home

6 Beds 7 Baths 5,709 SqFt

12132 MONTALCINO CIR, Windermere, FL 34786

Experience the essence of luxury lakefront living in this stunning contemporary Mediterranean estate, ideally positioned...

Listed by Caroline Perotti BELLA VIEW REALTY LLC

Stellar MLS
7211 STILL POND LN, Windermere, FL 34786
1/17 17

$4,490

Active

Single Family Home

4 Beds 4 Baths 3,091 SqFt

7211 STILL POND LN, Windermere, FL 34786

This property will be ready to be your home next January.Welcome to this former model home in one of Windermere's covete...

Listed by Victor Barroeta MBT REALTY LLC

Stellar MLS
8180 BOAT HOOK LOOP #304, Windermere, FL 34786
1/38 38

$2,400

Active

Condo

3 Beds 2 Baths 1,455 SqFt

8180 BOAT HOOK LOOP #304, Windermere, FL 34786

The perfect blend of comfort, convenience, and Central Florida lifestyle! This beautiful ground-floor residence offers e...

Listed by Hojin Chang RE/MAX PRIME PROPERTIES

Stellar MLS
12821 WESTSIDE VILLAGE LOOP, Windermere, FL 34786
1/42 42

$4,150

Active

Single Family Home

5 Beds 4 Baths 3,689 SqFt

12821 WESTSIDE VILLAGE LOOP, Windermere, FL 34786

This stunning home sits on a corner 5 bedrooms plus an office and huge bonus room. once you into the large foyer where y...

Listed by Marcos Paulo Nero, LLC LA ROSA REALTY KISSIMMEE

Stellar MLS
805 OAKDALE ST, Windermere, FL 34786
1/13 13

$2,800

Active

Single Family Home

3 Beds 2 Baths 1,710 SqFt

805 OAKDALE ST, Windermere, FL 34786

Live amongst the oaks in this 3BD/2BA large corner lot home in the heart of Olde Windermere. Just a short walk to the hi...

Listed by Ken Warren PREMIER MANAGEMENT GROUP INC

Stellar MLS
9733 CARILLON PARK DR, Windermere, FL 34786
1/75 75

$5,250,000

Active

Single Family Home

5 Beds 7 Baths 7,600 SqFt

9733 CARILLON PARK DR, Windermere, FL 34786

Redefine luxury living. Welcome home to an exceptional lifestyle with an estate that offers impeccable design and unpara...

Listed by Emily Lewis LAKESIDE REALTY WINDERMERE INC

Stellar MLS
11562 AMIDSHIP LN #208, Windermere, FL 34786
1/31 31

$2,095

Active

Condo

3 Beds 2 Baths 1,442 SqFt

11562 AMIDSHIP LN #208, Windermere, FL 34786

Freshly updated three bedroom, two full bathroom condo at Lakeside at Lakes of Windermere. Second floor unit with elevat...

Listed by Rafael Pierluisi ALFANO PROPERTY MANAGEMENT

Stellar MLS
14284 DESERT HAVEN ST #806, Windermere, FL 34786
1/27 27

$2,500

Active

Townhouse

3 Beds 3 Baths 1,840 SqFt

14284 DESERT HAVEN ST #806, Windermere, FL 34786

VACANT! Great location! Great Home! Move in this Great home inside the lovely Oasis Cove community in the very desirable...

Listed by Daniel Zheng CINO INTERNATIONAL INC

Stellar MLS
2943 MARQUESAS CT, Windermere, FL 34786
1/60 60

$4,200

Active

Single Family Home

4 Beds 3 Baths 2,145 SqFt

2943 MARQUESAS CT, Windermere, FL 34786

Come tour this incredible New England-style pool home in the Town of Windermere that sits on a meticulously manicured on...

Listed by Jessica Alicea INTEGRITY REAL ESTATE GROUP, LLC

Stellar MLS
2958 MARQUESAS CT, Windermere, FL 34786
1/32 32

$1,998,000

Active

Single Family Home

5 Beds 5 Baths 4,716 SqFt

2958 MARQUESAS CT, Windermere, FL 34786

This beautiful and elegant courtyard-style estate, complete with a PRIVATE GUEST HOUSE/IN-LAW SUITE, offers the ideal re...

Listed by Dianna Desboyaux EXP REALTY LLC

Stellar MLS
6507 ROSELLA CT, Windermere, FL 34786
1/92 92

$7,750,000

Active

Single Family Home

7 Beds 8 Baths 10,485 SqFt

6507 ROSELLA CT, Windermere, FL 34786

Luxury Living at its finest in one of Windermere's most unique Waterfront properties, with 2+ acres in the exclusive Kee...

Listed by DeAnna Sechrest DEANNA MARIE SECHREST

Stellar MLS
6626 BRIDGEWATER VILLAGE RD, Windermere, FL 34786
3D

$615,000

Active

Single Family Home

3 Beds 4 Baths 2,720 SqFt

6626 BRIDGEWATER VILLAGE RD, Windermere, FL 34786

--Beautiful Corner-Lot Home in The Vineyards of Horizons West-- <br>Welcome to one of Horizon West's most desirable nei...

Listed by David Dorman CENTURY 21 CARIOTI

Stellar MLS
8156 BOAT HOOK LOOP #303, Windermere, FL 34786
1/26 26

$2,095

Active

Condo

3 Beds 2 Baths 1,442 SqFt

8156 BOAT HOOK LOOP #303, Windermere, FL 34786

Third floor condo with three bedrooms, two full bathrooms at Lakeside at Lakes of Windermere. Private corner unit with e...

Listed by Rafael Pierluisi ALFANO PROPERTY MANAGEMENT

Stellar MLS
8265 MARITIME FLAG ST #101, Windermere, FL 34786
1/15 15

$2,375

Active

Townhouse

3 Beds 3 Baths 1,644 SqFt

8265 MARITIME FLAG ST #101, Windermere, FL 34786

Built in 2012, this spacious 3-bedroom, 2.5-bath townhouse offers the perfect blend of comfort, convenience, and communi...

Listed by Carissa Lawhun FLORIDA REALTY INVESTMENTS

Stellar MLS
13413 ZORI LN, Windermere, FL 34786
1/38 38

$675,000

Active

Single Family Home

4 Beds 3 Baths 2,830 SqFt

13413 ZORI LN, Windermere, FL 34786

Welcome to this Charming and stunning home located in a quiet Windermere neighborhood where the Lake Front homes with va...

Listed by Annie Kwan ORLANDO SUNSHINE REALTY

Stellar MLS
14217 BRIDGEWATER CROSSINGS BLVD, Windermere, FL 34786
1/34 34

$3,000

Active

Single Family Home

4 Beds 3 Baths 2,419 SqFt

14217 BRIDGEWATER CROSSINGS BLVD, Windermere, FL 34786

Don't miss out on this 4 bedroom 3 bathrooms in the tranquil Summerport community in Windermere. The first floor consist...

Listed by Azim Manji WEICHERT REALTORS HALLMARK PRO

Stellar MLS
5067 SAWYER COVE WAY, Windermere, FL 34786
1/48 48

$2,999,500

Active

Single Family Home

5 Beds 4 Baths 3,461 SqFt

5067 SAWYER COVE WAY, Windermere, FL 34786

STUNNING CUSTOM estate in the exclusive GATED community of Sawyer Sound - a private enclave of just 20 luxury homes, ide...

Listed by Denise Crabbe REVEL REALTY LLC

Stellar MLS
12136 CANYON SUN TRL, Windermere, FL 34786
1/76 76

$525,000

Active

Single Family Home

3 Beds 3 Baths 2,149 SqFt

12136 CANYON SUN TRL, Windermere, FL 34786

***The Veranda on Canyon Sun*** <br>A day in the life — where sunlight, serenity, and thoughtful design meet.*** <br>Mor...

Listed by Karan Wienker COLDWELL BANKER REALTY

Stellar MLS
5412 WATER CREEK DR, Windermere, FL 34786
1/73 73

$1,999,900

Active

Single Family Home

4 Beds 5 Baths 4,247 SqFt

5412 WATER CREEK DR, Windermere, FL 34786

Adjacent to the northwest corner of Lake Butler, beautifully set along the shores of Lake William Davis, this custom Med...

Listed by Kari Fleck THE REAL ESTATE COLLECTION LLC

Stellar MLS
8174 ENCHANTMENT DR #1601, Windermere, FL 34786
1/21 21

$3,000

Active

Townhouse

3 Beds 3 Baths 1,852 SqFt

8174 ENCHANTMENT DR #1601, Windermere, FL 34786

Welcome to your new home in beautiful Windermere! This charming 3 bedroom and 2.5 bath townhome offers a bright and open...

Listed by Vivian Branco MS LAND & BUILDING LLC

Stellar MLS
11714 DELWICK DR, Windermere, FL 34786
1/43 43

$850,000

Active

Single Family Home

4 Beds 3 Baths 2,764 SqFt

11714 DELWICK DR, Windermere, FL 34786

Just imagine yourself living in a pristine community with a long, impressive entrance that is guard gated like The Rese...

Listed by Veronica Davis-Lee RE/MAX 200 REALTY

Stellar MLS
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LPT Realty

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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Marcus E Smith PA License ID: 3187002

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

1400 S. International Pkwy Lake Mary, FL 3274

Get My App

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.