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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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FL >34786 >
Market Insights
12530 CLIMBING VINE CT, Windermere, FL 34786
1/73 73

$999,000

New

Single Family Home

5 Beds 4 Baths 3,407 SqFt

12530 CLIMBING VINE CT, Windermere, FL 34786

Tucked at the end of a quiet cul-de-sac in the sought after community of Windstone, this beautifully appointed Windermer...

Listed by Brian Hyser THE AGENCY ORLANDO

Stellar MLS
12661 CALDERDALE AVE, Windermere, FL 34786
1/44 44

$495,000

New

Single Family Home

3 Beds 2 Baths 1,696 SqFt

12661 CALDERDALE AVE, Windermere, FL 34786

Set in the desirable community of Wickham Park, this Windermere residence blends comfort, convenience, and everyday ease...

Listed by Brian Hyser THE AGENCY ORLANDO

Stellar MLS
13638 ANCILLA BLVD, Windermere, FL 34786
1/16 16

$3,750

New

Single Family Home

4 Beds 4 Baths 2,770 SqFt

13638 ANCILLA BLVD, Windermere, FL 34786

Discover this beautifully maintained two-story single-family home in the heart of Windermere, offering 4 spacious bedroo...

Listed by Jose Solano FUSION FLORIDA REALTY LLC

Stellar MLS
1626 WHITNEY ISLES DR, Windermere, FL 34786
1/8 8

$3,400

New

Single Family Home

4 Beds 4 Baths 2,645 SqFt

1626 WHITNEY ISLES DR, Windermere, FL 34786

4 Bedroom 4 bath rent home is in gated Community of Whitney Isles. The property has features 3 bedrooms and 3 bath downs...

Listed by Dewayne Smith CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
1804 MAPLE LEAF DR, Windermere, FL 34786
1/53 53

$1,025,000

New

Single Family Home

4 Beds 4 Baths 2,971 SqFt

1804 MAPLE LEAF DR, Windermere, FL 34786

Experience refined living at 1804 Maple Leaf Drive, an impeccably maintained corner-lot residence nestled in the highly ...

Listed by Anna McIntyre LAKESIDE REALTY WINDERMERE INC

Stellar MLS
2046 WESTOVER RESERVE BLVD, Windermere, FL 34786
1/29 29

$999,000

New

Single Family Home

5 Beds 4 Baths 3,516 SqFt

2046 WESTOVER RESERVE BLVD, Windermere, FL 34786

Welcome to Westover Reserve, a gated Windermere enclave celebrated for its tree-lined streets, strong community identity...

Listed by Hilary Hall COMPASS FLORIDA LLC

Stellar MLS
5723 OXFORD MOOR BLVD, Windermere, FL 34786
1/3 3

$8,500

New

Single Family Home

4 Beds 6 Baths 4,629 SqFt

5723 OXFORD MOOR BLVD, Windermere, FL 34786

For lease is a breathtaking dream home in Oxford Moor. This Windermere luxurious gated community is an upscale neighborh...

Listed by Hans Welbergen WINDERMERE INTERNATIONAL REALTY

Stellar MLS
6222 LECCO WAY, Windermere, FL 34786
1/51 51

$1,629,000

New

Single Family Home

5 Beds 4 Baths 3,967 SqFt

6222 LECCO WAY, Windermere, FL 34786

Custom Home in Prestigious Waterstone on Lake Butler. <br> <br>This stunning Mizner/Palm Beach–inspired residence offers...

Listed by Matty Castillo, PA EMPIRE NETWORK REALTY

Stellar MLS
Windermere, FL 34786
1/19 19

$3,539

New

Single Family Home

4 Beds 4 Baths 2,745 SqFt

Windermere, FL 34786

Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, 3.5 bathrooms, 3 car garage and appro...

Listed by Cathy Behe TAH FLORIDA LLC

Stellar MLS
Windermere, FL 34786
1/21 21

$3,309

New

Single Family Home

4 Beds 4 Baths 2,659 SqFt

Windermere, FL 34786

Take a look at this beautiful home, Clean and Move-In Ready, featuring 4 bedrooms, 3.5 bathrooms, 2 car garage and appro...

Listed by Cathy Behe TAH FLORIDA LLC

Stellar MLS
13927 BLUEBIRD POND RD, Windermere, FL 34786
1/38 38

$535,000

New

Single Family Home

4 Beds 3 Baths 2,345 SqFt

13927 BLUEBIRD POND RD, Windermere, FL 34786

Welcome to this beautifully renovated 3 bed, 2 bath plus office space property featuring modern vinyl flooring throughou...

Listed by Ayoub Aitelhaj THE SIMON SIMAAN GROUP

Stellar MLS
6920 HELMSLEY CIR, Windermere, FL 34786
1/22 22

$2,900

New

Single Family Home

3 Beds 2 Baths 2,156 SqFt

6920 HELMSLEY CIR, Windermere, FL 34786

Welcome to this stunning home located at 6920 Helmsley Cir, in the highly desirable community of Windermere. This spacio...

Listed by Xiaoguang Ruan AAA GLOBAL VENTURES PA

Stellar MLS
8436 GREENBANK BLVD, Windermere, FL 34786
1/19 19

$2,850

New

Single Family Home

3 Beds 2 Baths 1,894 SqFt

8436 GREENBANK BLVD, Windermere, FL 34786

Welcome to your dream home at 8436 Greenbank Blvd in Windermere! This single-family property features 3 bedrooms, 2 bath...

Listed by Daniel Colombo REALTY HUB

Stellar MLS
3103 SEIGNEURY DR, Windermere, FL 34786
1/64 64

$2,700,000

New

Single Family Home

8 Beds 6 Baths 5,607 SqFt

3103 SEIGNEURY DR, Windermere, FL 34786

Stunning 8BR/5BA Renovated Estate in Exclusive Windermere Community <br>Beautifully updated 7-bedroom, 5-bathroom home l...

Listed by Arletis Delarm NEW SOLUTIONS REALTY INC

Stellar MLS
9508 PINE TERRACE CT, Windermere, FL 34786
1/37 37

$3,700

New

Single Family Home

3 Beds 2 Baths 1,723 SqFt

9508 PINE TERRACE CT, Windermere, FL 34786

Recently renovated and move in ready, this beautiful and unique home is perfectly situated in the heart of Windermere. E...

Listed by Carlos Ladron de Guevara REAL BROKER, LLC

Stellar MLS
311 E 8TH AVE, Windermere, FL 34786
1/53 53

$6,750

New

Single Family Home

5 Beds 4 Baths 3,805 SqFt

311 E 8TH AVE, Windermere, FL 34786

One or more photo(s) has been virtually staged. Discover exceptional lakefront living in the heart of Windermere with th...

Listed by Karen O'Neil COLDWELL BANKER RESIDENTIAL RE

Stellar MLS
7028 VENTNOR DR, Windermere, FL 34786
3D

$520,000

New

Townhouse

4 Beds 3 Baths 1,980 SqFt

7028 VENTNOR DR, Windermere, FL 34786

PRISTINE 4 Bedroom 3 Bath End Unit Townhome in Beautiful Preston Square Windermere with Brand New Roof and exterior pain...

Listed by Amanda Black PA UPSIDE REAL ESTATE INC

Stellar MLS
8222 STONE MASON CT, Windermere, FL 34786
1/54 54

$2,895,000

New

Single Family Home

6 Beds 7 Baths 6,834 SqFt

8222 STONE MASON CT, Windermere, FL 34786

Welcome to 8222 Stone Mason Court—an exceptional J. Richard Watson estate perfectly positioned along the 8th green of th...

Listed by Jay Martin CORCORAN PREMIER REALTY

Stellar MLS
11738 CAMDEN PARK DR, Windermere, FL 34786
1/63 63

$1,125,000

New

Single Family Home

4 Beds 3 Baths 2,635 SqFt

11738 CAMDEN PARK DR, Windermere, FL 34786

Welcome to your dream home in the prestigious, guard-gated community of Keenes Pointe. This stunning 4-bedroom, 3-bathro...

Listed by Sherri Palmer EXP REALTY LLC

Stellar MLS
101 LEE ST, Windermere, FL 34786
1/100 100

$8,000

New

Single Family Home

5 Beds 4 Baths 4,186 SqFt

101 LEE ST, Windermere, FL 34786

A new long elegantly paved driveway leads up to this beautifully updated 5-bedroom, 4,200 sq. ft. home in the charming T...

Listed by Carey Sheffield ISLEWORTH REALTY LLC

Stellar MLS
12333 VIA DERNA PL, Windermere, FL 34786
1/57 57

$459,000

New

Townhouse

3 Beds 3 Baths 1,919 SqFt

12333 VIA DERNA PL, Windermere, FL 34786

Welcome to this beautifully updated 1,919 sq/ft townhome in the highly desirable Carrington community of Windermere. Thi...

Listed by Marco Romero YELLOW ROCK REALTY CORP

Stellar MLS
7625 SUTHERTON LN, Windermere, FL 34786
1/33 33

$439,000

New

Townhouse

3 Beds 3 Baths 1,505 SqFt

7625 SUTHERTON LN, Windermere, FL 34786

Welcome to this beautifully renovated and meticulously maintained 3-bedroom, 2.5-bath end-unit townhome in the highly so...

Listed by Sharon Six SOLD BY SIX REALTY, LLC

Stellar MLS
8145 SERENITY SPRING DR #GE, Windermere, FL 34786
1/31 31

$2,500

New

Townhouse

3 Beds 3 Baths 1,512 SqFt

8145 SERENITY SPRING DR #GE, Windermere, FL 34786

Beautiful townhome 3 BED, 2.5 BATH, 1 CAR GARAGE in resort style gated community. Stainless steel kitchen appliances, wa...

Listed by Isabel Sirizzotti SUNNY 365 REALTY GROUP

Stellar MLS
8746 CRESCENDO AVE, Windermere, FL 34786
1/56 56

$5,350

New

Single Family Home

4 Beds 4 Baths 3,050 SqFt

8746 CRESCENDO AVE, Windermere, FL 34786

Discover refined Florida living in this beautifully appointed premium corner-lot residence located in one of Windermere'...

Listed by Mariana Micheti M2M 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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LPT Realty

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.