Homes for Sale in Windermere, FL

By Jon Brooks, Co-Founder, Momentum Realty · Updated October 23, 2026

240 homes are for sale in Windermere, FL as of 2026-10-23, with 21 more under contract. The median list price is $950,000 ($326/sq ft), most homes list between $400K to $4.35M, and the median listing has been on the market 76 days. That is 197 houses, 10 condos and 33 townhouses. 19 homes came on the market this week and 449 sold in the last 12 months at a median of $640,000.

Newest homes for sale in Windermere

The most recently listed homes in Windermere, newest first, with photos. Each card opens the full listing with every photo, the community’s sales history and a tour request. Homes marked New listed in the last seven days.

$12.35M New

7 bd · 9.5 ba · 11,465 sq ft · built 2022

9312 BLANCHE COVE DR, 34786

Isleworth 5Th Amd

Listing courtesy of ISLEWORTH REALTY LLC

$3.25M New

4 bd · 5.5 ba · 4,200 sq ft · built 2021

12620 S LAKE SAWYER LANE, 34786

Windermere

Listing courtesy of SERHANT

$3.15M New

4 bd · 4.5 ba · 4,290 sq ft · built 2026

1815 WINDERMERE ROAD, 34786

Windermere

Listing courtesy of BALDWIN PARK REALTY LLC

$1.80M New

6 bd · 6 ba · 4,945 sq ft · built 2013

7413 LAKE ALBERT DRIVE, 34786

Lake Burden South Ph I

Listing courtesy of GOLFPARK PROPERTIES

$620,000 New

4 bd · 3.5 ba · 2,461 sq ft · built 2015

13019 GARRIDAN AVENUE, 34786

Windermere Sound

Listing courtesy of LA ROSA REALTY LLC

$2.90M New

7 bd · 8.5 ba · 7,042 sq ft · built 2006

4205 CLARICE COURT, 34786

Windermere

Listing courtesy of LAKESIDE REALTY WINDERMERE INC

$1.09M New

4 bd · 3.5 ba · 3,607 sq ft · built 1998

2009 WESTOVER RESERVE BOULEVARD, 34786

Windermere

Listing courtesy of STOCKWORTH REALTY GROUP

$709,000 New

4 bd · 3 ba · 2,749 sq ft · built 2003

14038 EDEN ISLE BOULEVARD, 34786

Bella Notte/Vizcaya Ph 03 A C

Listing courtesy of EXP REALTY LLC

$435,000 New

3 bd · 2.5 ba · 1,743 sq ft · built 2015

11267 GRANDER DRIVE, 34786

Windermere

Listing courtesy of AUTHENTIC REAL ESTATE TEAM

$535,000 New

4 bd · 3 ba · 2,361 sq ft · built 2004

4936 WISE BIRD DRIVE, 34786

Windermere

Listing courtesy of COLDWELL BANKER REALTY

$2.19M New

5 bd · 5.5 ba · 3,582 sq ft · built 2027

6518 SAWYER SHORES LANE, 34786

Sawyer Shores Sub

Listing courtesy of WRA BUSINESS & REAL ESTATE

$1.19M New

5 bd · 4.5 ba · 4,999 sq ft · built 2014

17538 BLACK RAIL STREET, 34786

Enclave

Listing courtesy of KARDOSH REALTY

$5.30M New

6 bd · 7 ba · 9,669 sq ft · built 2007

9615 WINDY RIDGE ROAD, 34786

Windsor Hill

Listing courtesy of KELLER WILLIAMS CLASSIC

$750,000 New

5 bd · 4 ba · 3,373 sq ft · built 2004

6208 TALARIA DRIVE, 34786

Windermere

Listing courtesy of OLYMPUS EXECUTIVE REALTY INC

$599,000 New

3 bd · 2 ba · 1,948 sq ft · built 2007

13125 PENSHURST LANE, 34786

Lakes/Windermere Ph 03 P & Q

Listing courtesy of CASTLE REALTY PROFESSIONAL GROUP LLC

$2.40M New

5 bd · 4 ba · 5,139 sq ft · built 2007

12722 S LAKE SAWYER LANE, 34786

Windermere

Listing courtesy of KELLY PRICE & COMPANY LLC

$615,000 New

4 bd · 3.5 ba · 2,628 sq ft · built 2009

7555 TATTANT BOULEVARD, 34786

Windermere

Listing courtesy of BUYER REBATES REALTY

$559,000 New

3 bd · 2 ba · 2,085 sq ft · built 2006

4827 FLINT ROAD, 34786

Windermere

Listing courtesy of COMPASS FLORIDA LLC

$405,000 New

3 bd · 2.5 ba · 1,382 sq ft · built 2021

8867 HERENCIA ALLEY, 34786

Legado

Listing courtesy of AAA GLOBAL VENTURES PA

$1.45M

7 bd · 4.5 ba · 4,443 sq ft · built 2025

14274 CREST PALM AVENUE, 34786

Windermere

Listing courtesy of DOUGLAS ELLIMAN

$1.35M

5 bd · 4.5 ba · 3,835 sq ft · built 2011

7231 SANGALLA DRIVE, 34786

Casa Del Lago

Listing courtesy of ONE LUXURY INTERNATIONAL LLC

$1.05M

4 bd · 3 ba · 2,984 sq ft · built 2004

5944 CAYMUS LOOP, 34786

Keene’s Pointe

Listing courtesy of SOUTHERN REALTY GROUP LLC

$324,900

3 bd · 2 ba · 1,455 sq ft · built 2007

8276 MARITIME FLAG ST #1204, 34786

Windermere

Listing courtesy of HOMEVEST REALTY

$2.39M

5 bd · 4.5 ba · 4,185 sq ft · built 2004

6544 CARTMEL LANE, 34786

Reserve At Lake Butler Sound

Listing courtesy of FLORIDA CONNEXION PROPERTIES

Windermere homes for sale by price

Every active listing in Windermere grouped by price, with the newest listings in each band. The median is $950,000; the busiest band is $1M and up.

$200K – $300K: 4 homes

• $299,997 · 2 bd / 2 ba / 1,161 sq ft · 8168 BOAT HOOK LOOP #302
• $290,000 · 2 bd / 2 ba / 1,161 sq ft · 11446 JASPER KAY TERRACE #202
• $295,000 · 2 bd / 2 ba / 1,161 sq ft · 8180 BOAT HOOK LOOP #102
• $299,500 · 2 bd / 2 ba / 1,161 sq ft · 8180 BOAT HOOK LOOP #109 (Lakeside/Lks)

$300K – $400K: 20 homes

• $324,900 · 3 bd / 2 ba / 1,455 sq ft · 8276 MARITIME FLAG ST #1204
• $350,000 · 3 bd / 2 ba / 1,332 sq ft · 8179 MARITIME FLAG STREET #206
• $399,000 · 3 bd / 2.5 ba / 1,651 sq ft · 14077 ANCILLA BOULEVARD
• $398,000 · 4 bd / 2.5 ba / 1,706 sq ft · 14350 BRIDGEWATER CROSSINGS BOULEVARD

$400K – $500K: 19 homes

• $435,000 · 3 bd / 2.5 ba / 1,743 sq ft · 11267 GRANDER DRIVE
• $405,000 · 3 bd / 2.5 ba / 1,382 sq ft · 8867 HERENCIA ALLEY (Legado)
• $430,000 · 3 bd / 2.5 ba / 1,676 sq ft · 11963 VERMILLION AVENUE (Windermere Trails)
• $400,000 · 3 bd / 2.5 ba / 1,545 sq ft · 12303 LANGSTAFF DRIVE

$500K – $750K: 56 homes

• $620,000 · 4 bd / 3.5 ba / 2,461 sq ft · 13019 GARRIDAN AVENUE (Windermere Sound)
• $709,000 · 4 bd / 3 ba / 2,749 sq ft · 14038 EDEN ISLE BOULEVARD (Bella Notte/Vizcaya Ph 03 A C)
• $535,000 · 4 bd / 3 ba / 2,361 sq ft · 4936 WISE BIRD DRIVE
• $599,000 · 3 bd / 2 ba / 1,948 sq ft · 13125 PENSHURST LANE (Lakes/Windermere Ph 03 P & Q)

$750K – $1M: 24 homes

• $750,000 · 5 bd / 4 ba / 3,373 sq ft · 6208 TALARIA DRIVE
• $799,000 · 4 bd / 3.5 ba / 2,996 sq ft · 12785 WESTSIDE VILLAGE LOOP (Westside Village)
• $950,000 · 4 bd / 3 ba / 2,680 sq ft · 8524 VIVARO ISLE WAY (Windermere Isle)
• $860,000 · 4 bd / 3 ba / 2,704 sq ft · 11727 DELWICK DRIVE (Reserve At Belmere)

$1M and up: 117 homes

• $1.80M · 6 bd / 6 ba / 4,945 sq ft · 7413 LAKE ALBERT DRIVE (Lake Burden South Ph I)
• $3.15M · 4 bd / 4.5 ba / 4,290 sq ft · 1815 WINDERMERE ROAD
• $3.25M · 4 bd / 5.5 ba / 4,200 sq ft · 12620 S LAKE SAWYER LANE
• $12.35M · 7 bd / 9.5 ba / 11,465 sq ft · 9312 BLANCHE COVE DR (Isleworth 5Th Amd)

Every home for sale in Windermere right now (240)

All 240 active Windermere listings with a detail page, newest first, refreshed twice a day from the MLS.

• $12.35M · 7 bd / 9.5 ba / 11,465 sq ft · 9312 BLANCHE COVE DR (Isleworth 5Th Amd)
• $3.25M · 4 bd / 5.5 ba / 4,200 sq ft · 12620 S LAKE SAWYER LANE
• $3.15M · 4 bd / 4.5 ba / 4,290 sq ft · 1815 WINDERMERE ROAD
• $1.80M · 6 bd / 6 ba / 4,945 sq ft · 7413 LAKE ALBERT DRIVE (Lake Burden South Ph I)
• $620,000 · 4 bd / 3.5 ba / 2,461 sq ft · 13019 GARRIDAN AVENUE (Windermere Sound)
• $2.90M · 7 bd / 8.5 ba / 7,042 sq ft · 4205 CLARICE COURT
• $1.09M · 4 bd / 3.5 ba / 3,607 sq ft · 2009 WESTOVER RESERVE BOULEVARD
• $709,000 · 4 bd / 3 ba / 2,749 sq ft · 14038 EDEN ISLE BOULEVARD (Bella Notte/Vizcaya Ph 03 A C)
• $435,000 · 3 bd / 2.5 ba / 1,743 sq ft · 11267 GRANDER DRIVE
• $535,000 · 4 bd / 3 ba / 2,361 sq ft · 4936 WISE BIRD DRIVE
• $2.19M · 5 bd / 5.5 ba / 3,582 sq ft · 6518 SAWYER SHORES LANE (Sawyer Shores Sub)
• $1.19M · 5 bd / 4.5 ba / 4,999 sq ft · 17538 BLACK RAIL STREET (Enclave)
• $5.30M · 6 bd / 7 ba / 9,669 sq ft · 9615 WINDY RIDGE ROAD (Windsor Hill)
• $750,000 · 5 bd / 4 ba / 3,373 sq ft · 6208 TALARIA DRIVE
• $599,000 · 3 bd / 2 ba / 1,948 sq ft · 13125 PENSHURST LANE (Lakes/Windermere Ph 03 P & Q)
• $2.40M · 5 bd / 4 ba / 5,139 sq ft · 12722 S LAKE SAWYER LANE
• $615,000 · 4 bd / 3.5 ba / 2,628 sq ft · 7555 TATTANT BOULEVARD
• $559,000 · 3 bd / 2 ba / 2,085 sq ft · 4827 FLINT ROAD
• $405,000 · 3 bd / 2.5 ba / 1,382 sq ft · 8867 HERENCIA ALLEY (Legado)
• $1.45M · 7 bd / 4.5 ba / 4,443 sq ft · 14274 CREST PALM AVENUE
• $1.35M · 5 bd / 4.5 ba / 3,835 sq ft · 7231 SANGALLA DRIVE (Casa Del Lago)
• $1.05M · 4 bd / 3 ba / 2,984 sq ft · 5944 CAYMUS LOOP (Keene’s Pointe)
• $324,900 · 3 bd / 2 ba / 1,455 sq ft · 8276 MARITIME FLAG ST #1204
• $2.39M · 5 bd / 4.5 ba / 4,185 sq ft · 6544 CARTMEL LANE (Reserve At Lake Butler Sound)
• $520,000 · 3 bd / 2 ba / 1,681 sq ft · 12679 CALDERDALE AVENUE
• $799,000 · 4 bd / 3.5 ba / 2,996 sq ft · 12785 WESTSIDE VILLAGE LOOP (Westside Village)
• $679,000 · 3 bd / 2.5 ba / 2,177 sq ft · 2053 WOODY DRIVE
• $620,000 · 4 bd / 3.5 ba / 2,661 sq ft · 8576 POWDER RIDGE TRAIL (Windermere Trails)
• $430,000 · 3 bd / 2.5 ba / 1,676 sq ft · 11963 VERMILLION AVENUE (Windermere Trails)
• $1.60M · 4 bd / 3.5 ba / 3,751 sq ft · 6533 CARTMEL LANE (Reserve At Lake Butler Sound)
• $399,000 · 3 bd / 2.5 ba / 1,651 sq ft · 14077 ANCILLA BOULEVARD
• $350,000 · 3 bd / 2 ba / 1,332 sq ft · 8179 MARITIME FLAG STREET #206
• $299,997 · 2 bd / 2 ba / 1,161 sq ft · 8168 BOAT HOOK LOOP #302
• $4.35M · 5 bd / 5 ba / 5,305 sq ft · 9602 MAYWOOD DRIVE (Lake Down Shores)
• $2.00M · 4 bd / 4 ba / 3,912 sq ft · 8229 TIBET BUTLER DRIVE (Keene’s Pointe)
• $595,000 · 3 bd / 2 ba / 2,115 sq ft · 6858 MERRICK LANDING BOULEVARD
• $649,000 · 4 bd / 2.5 ba / 2,455 sq ft · 7030 MAPPERTON DRIVE (Lakes Of Windermere)
• $550,000 · 5 bd / 3.5 ba / 2,268 sq ft · 9021 VIA DI CANTI
• $1.28M · 4 bd / 2.5 ba / 2,441 sq ft · 104 E 1ST AVENUE (Town of Windermere)
• $720,000 · 4 bd / 2 ba / 2,516 sq ft · 6243 ANDREOZZI LANE
• $950,000 · 4 bd / 3 ba / 2,680 sq ft · 8524 VIVARO ISLE WAY (Windermere Isle)
• $6.95M · 7 bd / 7 ba / 8,722 sq ft · 6113 GROSVENOR SHORE DRIVE (Keene’s Pointe)
• $860,000 · 4 bd / 3 ba / 2,704 sq ft · 11727 DELWICK DRIVE (Reserve At Belmere)
• $689,900 · 5 bd / 3 ba / 3,006 sq ft · 6614 BRIDGEWATER VILLAGE RD (Vineyards Of Horizons West)
• $2.20M · 4 bd / 5 ba / 4,169 sq ft · 11532 WATERSTONE LOOP DRIVE (Waterstone)
• $625,000 · 4 bd / 2.5 ba / 2,683 sq ft · 12809 HOLDENBURY LANE
• $398,000 · 4 bd / 2.5 ba / 1,706 sq ft · 14350 BRIDGEWATER CROSSINGS BOULEVARD
• $4.00M · 5 bd / 5 ba / 5,580 sq ft · 6120 GREATWATER DRIVE (Keene’s Pointe)
• $562,000 · 3 bd / 2 ba / 1,855 sq ft · 7271 LONDALE BOULEVARD (Enclave/Berkshire Park B G H I)
• $400,000 · 3 bd / 2.5 ba / 1,545 sq ft · 12303 LANGSTAFF DRIVE
• $1.90M · 4 bd / 4.5 ba / 2,868 sq ft · 930 EAST BOULEVARD
• $530,000 · 4 bd / 2 ba / 2,020 sq ft · 13738 EDEN ISLE BOULEVARD
• $1.49M · 4 bd / 4 ba / 3,763 sq ft · 12721 JACOB GRACE COURT (Tildens Grove Ph 01 47/65)
• $290,000 · 2 bd / 2 ba / 1,161 sq ft · 11446 JASPER KAY TERRACE #202
• $560,000 · 4 bd / 2.5 ba / 2,214 sq ft · 11543 CHARNOCK DRIVE (Westside Village)
• $549,990 · 3 bd / 2.5 ba / 1,699 sq ft · 13317 LUSH LIME ALLEY (Lake Cawood Cove)
• $7.45M · 7 bd / 9 ba / 8,362 sq ft · 9343 TIBET POINTE CIRCLE
• $3.00M · 6 bd / 8 ba / 7,321 sq ft · 13101 BELLARIA CIRCLE (Bellaria)
• $489,900 · 3 bd / 2 ba / 1,820 sq ft · 13535 BRAMHAM LANE (Lakes/Windermere-Peachtree)
• $649,000 · 4 bd / 3.5 ba / 2,750 sq ft · 13324 JERVEY STREET
• $945,000 · 4 bd / 3.5 ba / 3,264 sq ft · 9010 REFLECTION POINTE DRIVE (Windermere Trails)
• $19.50M · 6 bd / 9 ba / 13,494 sq ft · 5192 VARDON DRIVE
• $1.40M · 5 bd / 4 ba / 4,186 sq ft · 101 LEE STREET (Town of Windermere)
• $645,000 · 4 bd / 3 ba / 2,214 sq ft · 7252 BACKWOODS TRAIL (Ashlin Park)
• $379,900 · 3 bd / 2.5 ba / 1,480 sq ft · 8608 BROOKVALE DRIVE (Lakes/Windermere Lake Reams Twnh)
• $775,000 · 4 bd / 3 ba / 2,224 sq ft · 8291 PROCIDA ISLE LANE (Windermere Isle)
• $700,000 · 1 bd / 1 ba / 750 sq ft · 628 FOREST STREET (Marsh Sub)
• $500,000 · 4 bd / 3 ba / 2,190 sq ft · 13424 HOPKINTON CT (Lakes Of Windermere Peachtree)
• $625,000 · 4 bd / 2.5 ba / 2,460 sq ft · 12909 CRAGSIDE LANE
• $500,000 · 4 bd / 2 ba / 2,190 sq ft · 13424 HOPKINTON COURT (Lakes/Windermere-Peachtree)
• $449,000 · 3 bd / 2.5 ba / 1,919 sq ft · 12333 VIA DERNA PLACE (Carrington)
• $3.29M · 5 bd / 6 ba / 5,502 sq ft · 4243 ISABELLA CIRCLE (Casabella)
• $2.69M · 5 bd / 6.5 ba / 5,747 sq ft · 8142 TIBET BUTLER DRIVE (Keene’s Pointe)
• $1.27M · 6 bd / 4.5 ba / 4,585 sq ft · 14360 CREST PALM AVENUE
• $2.95M · 5 bd / 4 ba / 7,153 sq ft · 4301 DOWN POINT LANE (Down Point Sub)
• $359,000 · 2 bd / 2.5 ba / 1,311 sq ft · 12417 CRUXBURY DRIVE (Lakes/Windermere-Lk Reams Twhm)
• $445,000 · 3 bd / 2.5 ba / 1,727 sq ft · 11734 WATER RUN ALLEY
• $1.23M · 5 bd / 3 ba / 2,831 sq ft · 12085 SANDY SHORES DRIVE
• $450,000 · 2 bd / 1 ba / 1,216 sq ft · 9764 GOTHA ROAD (Gotha Town)
• $8.00M · 6 bd / 7.5 ba / 8,038 sq ft · 9317 GLADYS GARDEN COURT (Gardens/Isleworth)
• $1.16M · 4 bd / 3.5 ba / 2,665 sq ft · 12989 WESTSIDE VILLAGE LOOP (Westside Village)
• $755,000 · 4 bd / 3.5 ba / 3,161 sq ft · 7211 STILL POND LANE
• $7.50M · 6 bd / 7.5 ba / 6,874 sq ft · 724 W 2ND AVENUE
• $650,000 · 5 bd / 3.5 ba / 2,966 sq ft · 12912 DROXFORD ROAD
• $2.50M · 5 bd / 4 ba / 4,661 sq ft · 5526 MARLEON DRIVE
• $1.35M · 5 bd / 3 ba / 3,356 sq ft · 2540 HEMPEL COVE CT (Lake Down Cove)
• $645,178 · 3 bd / 2.5 ba / 1,714 sq ft · 13325 LUSH LIME ALLEY (Lake Cawood Cove)
• $445,000 · 3 bd / 2.5 ba / 1,748 sq ft · 13048 GARRIDAN AVENUE
• $1.29M · 6 bd / 4.5 ba / 4,564 sq ft · 14213 CREST PALM AVENUE (Palms At Windermere)
• $320,000 · 3 bd / 2 ba / 1,442 sq ft · 8168 BOAT HOOK LOOP #303
• $3.58M · 5 bd / 6.5 ba / 5,362 sq ft · 4302 ISABELLA CIR (Casabella)
• $880,000 · 4 bd / 2.5 ba / 2,648 sq ft · 6309 EARTHGOLD DRIVE (West Point Commons)
• $870,000 · 4 bd / 3 ba / 3,746 sq ft · 9043 HORIZON POINTE TRAIL (Windermere Trails)
• $354,900 · 2 bd / 2.5 ba / 1,412 sq ft · 7430 BENTONSHIRE AVENUE (Wickham Park 04 05 06 09 10 11 12 01 Windermere)
• $1.60M · 5 bd / 4.5 ba / 4,219 sq ft · 1480 HEMPEL AVENUE (Gotha Town)
• $950,000 · 4 bd / 3 ba / 2,728 sq ft · 1243 DINGENS AVENUE (Gotha Town)
• $575,000 · 4 bd / 3 ba / 2,064 sq ft · 6828 HELMSLEY CIRCLE (Preston Square)
• $3.60M · 5 bd / 6 ba / 5,342 sq ft · 3986 ISABELLA CIRCLE (Casabella)
• $1.57M · 4 bd / 4.5 ba / 3,396 sq ft · 11832 WATERSTONE LOOP DRIVE
• $939,000 · 5 bd / 4.5 ba / 3,797 sq ft · 9609 WESTOVER CLUB CIRCLE
• $410,000 · 3 bd / 2.5 ba / 1,881 sq ft · 11425 BROWNSTONE STREET (Lake Burden South Ph I)
• $2.30M · 5 bd / 5.5 ba / 4,094 sq ft · 11113 LAKE BUTLER BOULEVARD (Wauseon Ridge)
• $2.24M · 4 bd / 5.5 ba / 4,812 sq ft · 6102 S HAMPSHIRE CT (Keene’s Pointe)
• $528,000 · 3 bd / 2.5 ba / 1,853 sq ft · 8630 POWDER RIDGE TRAIL (Windermere Trails)
• $673,000 · 4 bd / 2.5 ba / 2,754 sq ft · 5421 GEMGOLD COURT
• $398,000 · 3 bd / 2.5 ba / 1,547 sq ft · 8860 HERENCIA ALLEY
• $1.87M · 6 bd / 6.5 ba / 5,140 sq ft · 7467 LAKE ALBERT DRIVE (Lake Burden South Ph I)
• $1.50M · 5 bd / 4 ba / 3,656 sq ft · 17526 BLACK RAIL STREET (Enclave)
• $5.50M · 6 bd / 7 ba / 6,442 sq ft · 1330 LAKE OLIVIA (Lake Olivia Reserve)
• $1.90M · 6 bd / 6 ba / 5,869 sq ft · 4282 MCKINNON ROAD
• $3.99M · 6 bd / 7 ba / 6,896 sq ft · 4201 ISABELLA CIRCLE (Casabella)
• $1.70M · 4 bd / 3.5 ba / 3,680 sq ft · 8241 TIBET BUTLER DRIVE (Keene’s Pointe)
• $365,000 · 3 bd / 2.5 ba / 1,579 sq ft · 5579 SOMERSBY ROAD
• $3.10M · 4 bd / 4.5 ba / 4,296 sq ft · 12102 MONTALCINO CIRCLE (Casa Del Lago)
• $1.49M · 4 bd / 2 ba / 2,627 sq ft · 212 W 1ST AVENUE (Town of Windermere)
• $6.90M · 5 bd / 5.5 ba / 7,158 sq ft · 6055 LOUISE COVE DRIVE (Isleworth West)
• $525,000 · 3 bd / 2 ba / 1,926 sq ft · 6679 DUNCASTER STREET
• $3.40M · 6 bd / 6.5 ba / 5,666 sq ft · 9679 WESTOVER ROBERTS RD
• $3.00M · 6 bd / 4.5 ba / 4,282 sq ft · 7720 FICQUETTE ROAD (Lake Hancock Shores)
• $675,000 · 5 bd / 4.5 ba / 2,963 sq ft · 7236 PENKRIDGE LANE
• $610,000 · 4 bd / 4.5 ba / 2,192 sq ft · 12749 GARRIDAN AVENUE (Wickham Park)
• $510,000 · 4 bd / 2.5 ba / 2,074 sq ft · 11938 SILVERLAKE PARK DRIVE (Windermere Trails)
• $395,000 · 3 bd / 2.5 ba / 1,335 sq ft · 7752 RIGBY STREET
• $438,000 · 4 bd / 2.5 ba / 1,631 sq ft · 8386 IRON MOUNTAIN TRAIL (Windermere Trails)
• $394,900 · 3 bd / 2.5 ba / 1,369 sq ft · 12744 LANGSTAFF DRIVE (Lakes/Windermere-Lk Reams Twnh)
• $379,900 · 3 bd / 2.5 ba / 1,644 sq ft · 12914 VENNETTA WAY
• $2.25M · 5 bd / 4.5 ba / 4,504 sq ft · 9904 BRENTFORD COURT (Keene’s Pointe)
• $1.06M · 4 bd / 4 ba / 3,646 sq ft · 8344 BOWDEN WAY (Keene’s Pointe)
• $350,000 · 3 bd / 2.5 ba / 1,644 sq ft · 7712 FORDSON LANE
• $1.59M · 4 bd / 3.5 ba / 3,166 sq ft · 12417 MONTALCINO CIRCLE (Casa Del Lago)
• $4.50M · 5 bd / 6 ba / 6,159 sq ft · 6719 VALHALLA WAY (Keenes Pointe 46 104 Windermere)
• $579,000 · 3 bd / 2 ba / 1,706 sq ft · 13231 ROXBORO ROAD
• $5.60M · 5 bd / 4.5 ba / 5,511 sq ft · 800 W 2ND AVENUE (Aladar On Lake Butler)
• $699,900 · 4 bd / 3 ba / 2,665 sq ft · 6363 SEDONA LEAF COURT
• $6.70M · 8 bd / 8.5 ba / 8,133 sq ft · 8342 BOYLA COURT
• $2.79M · 6 bd / 7.5 ba / 6,781 sq ft · 13250 BELLARIA CIRCLE (Bellaria)
• $325,000 · 3 bd / 2 ba / 1,442 sq ft · 11446 JASPER KAY TERRACE #103
• $659,000 · 4 bd / 3.5 ba / 2,610 sq ft · 7537 BROFIELD AVENUE
• $15.90M · 8 bd / 9.5 ba / 14,068 sq ft · 6119 GROSVENOR SHORE DRIVE (Keenes Point)
• $949,000 · 4 bd / 3 ba / 3,478 sq ft · 2512 TRYON PLACE
• $429,000 · 4 bd / 2.5 ba / 1,910 sq ft · 11429 BROWNSTONE STREET (Lake Burden South Ph I)
• $324,900 · 2 bd / 2.5 ba / 1,232 sq ft · 14030 SPARKLING COVE LANE #603
• $2.50M · 6 bd / 4 ba / 4,858 sq ft · 1629 HEMPEL AVENUE
• $798,000 · 5 bd / 5 ba / 3,373 sq ft · 4642 RIVER GEM AVENUE (Summerport)
• $539,900 · 3 bd / 2 ba / 1,819 sq ft · 9433 PALM TREE DRIVE (Silver Woods)
• $1.99M · 5 bd / 5 ba / 4,228 sq ft · 1118 ESTANCIA WOODS LOOP
• $1.15M · 4 bd / 3 ba / 3,540 sq ft · 2009 WOODY DRIVE
• $550,000 · 3 bd / 2 ba / 1,948 sq ft · 13137 PENSHURST LANE (Lakes/Windermere Ph 03 P & Q)
• $555,000 · 3 bd / 2 ba / 1,706 sq ft · 13219 CHARFIELD STREET
• $1.90M · 4 bd / 5.5 ba / 5,515 sq ft · 1238 LAKE WHITNEY DRIVE

Showing the newest 150 of 240; the price bands above and the map cover the rest.

Homes for sale in Windermere by ZIP code

Where the inventory is: active listings and the median asking price by ZIP. ZIPs link to their housing scorecard.

Windermere communities with the most homes for sale

The Windermere neighborhoods and subdivisions with active listings, the median asking price in each, and what homes there actually sold for over the last 12 months. Community names open the community guide with live inventory, sales history, HOA and schools.

What is for sale in Windermere: property types

• Single-family houses: 197
• Townhouses: 33
• Condos: 10

Browse by type: Condos for sale in Windermere (10) · Townhomes for sale in Windermere (33).

The Windermere real estate market right now

Over the last 12 months 449 homes sold in Windermere at a median of $640,000 (-0.6% year over year), $266 per square foot. Sellers received 95% of list price and homes took a median 39 days to go under contract. With 240 homes for sale against that sales pace, months of supply is 6.4, a buyer’s market by the six-month rule. Cash buyers accounted for 27% of sales. New construction was 4% of sales.

Windermere supply by price band

Windermere home prices by year

Median sold price, closed sales, days on market and sale-to-list ratio by year, from Momentum’s MLS record.

What a home in Windermere costs to own

Take the median $950,000 listing with 20% down at today’s 7.32% 30-year rate: principal and interest run about $5,221/month. Orange County’s typical millage of 16.67 puts property tax near $15,006/year after the $50,000 homestead exemption — and that is the reset bill a buyer pays, not the seller’s capped one. Citizens’ average premium in Orange County is about $1,409/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $6,589/month plus any HOA or CDD assessment.

Explore Windermere

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Homes for sale near Windermere

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• Homes for sale in Golden Oak, FL — 6 listings

Recently off market in Windermere

Homes in Windermere that left the market most recently, with their last list price and a public-record page for each address. Off-market pages keep the community, tax and sales-history context after a listing closes or expires.

• 9600 Ambleside Drive · last listed $975,000 · off market Oct 21, 2026
• 5746 Oxford Moor Boulevard · last listed $1,289,000 · off market Oct 21, 2026
• 9237 Mcdavid Court · last listed $749,000 · off market Oct 20, 2026
• 11942 Sheltering Pine Drive · last listed $939,000 · off market Oct 20, 2026
• 12085 Sandy Shores Drive #D · last listed $1,275,000 · off market Oct 19, 2026
• 11753 Vinci Drive · last listed $2,150,000 · off market Oct 19, 2026
• 8266 Bryce Canyon Avenue · last listed $470,000 · off market Oct 18, 2026
• 7723 Fairgrove Avenue · last listed $380,000 · off market Oct 18, 2026
• 13303 Penshurst Lane · last listed $669,900 · off market Oct 18, 2026
• 12826 Woodmere Close Dr · last listed $650,000 · off market Oct 18, 2026
• 12676 Salomon Cove Drive · last listed $1,300,000 · off market Oct 18, 2026
• 9349 Tibet Pointe Circle · last listed $6,995,000 · off market Oct 17, 2026

Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Windermere as of 2026-10-23 and refresh as homes list and sell. Listings courtesy of Stellar MLS as distributed by MLS GRID. The data relating to real estate for sale on this page comes in part from the Internet Data Exchange (IDX) program of the MLS(s) named above; listings held by brokerages other than Momentum Realty are marked with the listing brokerage’s name. Information is deemed reliable but not guaranteed. Estimates are not guarantees. Equal Housing Opportunity.