Homes for Sale in Winter Springs, FL

By Jon Brooks, Co-Founder, Momentum Realty · Updated October 15, 2026

155 homes are for sale in Winter Springs, FL as of 2026-10-15, with 14 more under contract. The median list price is $419,900 ($242/sq ft), most homes list between $235K to $670K, and the median listing has been on the market 30 days. That is 115 houses, 8 condos and 32 townhouses. 36 homes came on the market this week and 267 sold in the last 12 months at a median of $444,997.

Newest homes for sale in Winter Springs

The most recently listed homes in Winter Springs, 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.

$205,000 New

2 bd · 2 ba · 1,224 sq ft · built 1987

499 CLUB DRIVE, 32708

Cypress Club

Listing courtesy of BLOOM HOME GROUP REALTY LLC

$2.50M New

6 bd · 5 ba · 6,132 sq ft · built 2026

1447 BIRD ROAD, 32708

Talis Crossing

Listing courtesy of SIMPLICITY: A RE BROKERAGE CO

$925,000 New

5 bd · 3.5 ba · 3,521 sq ft · built 1999

609 VIANA COURT, 32708

Seville Chase

Listing courtesy of WEMERT GROUP REALTY LLC

$849,900 New

4 bd · 3.5 ba · 2,597 sq ft · built 1993

1522 EAGLE NEST CIRCLE, 32708

Winter Springs

Listing courtesy of THE AGENCY FL

$775,000 New

5 bd · 3.5 ba · 3,273 sq ft · built 2021

957 TALON PLACE, 32708

Northern Oaks

Listing courtesy of ORANGE SLICE PROPERTIES

Winter Springs
photos on the listing

$559,000 New

3 bd · 2 ba · 2,292 sq ft · built 1982

1008 FOREST CIRCLE, 32708

Winter Springs

Listing courtesy of LIVE FLORIDA NOW LLC

$550,000 New

3 bd · 2 ba · 1,735 sq ft · built 1994

766 ANDOVER CIRCLE, 32708

Winter Springs

Listing courtesy of MILLENIUM REALTY GROUP

$489,000 New

3 bd · 2.5 ba · 1,680 sq ft · built 2019

154 WOODED VINE DRIVE, 32708

Tuskawilla Crossings 34'S

Listing courtesy of PINEAPPLE PLACE REALTY, LLC

$419,900 New

3 bd · 2 ba · 1,510 sq ft · built 1979

1120 DAPPLED ELM LN LANE, 32708

Winter Springs

Listing courtesy of ABSOLUTE REALTY GROUP, LLC

$375,000 New

3 bd · 2 ba · 1,812 sq ft · built 1984

867 BENCHWOOD DRIVE, 32708

Winter Springs

Listing courtesy of KELLER WILLIAMS ADVANTAGE 2 REALTY

$355,000 New

3 bd · 2 ba · 1,373 sq ft · built 1971

140 BOMBAY AVENUE, 32708

Winter Springs

Listing courtesy of FLORIDA REALTY OF MIAMI CORP

$350,000 New

2 bd · 2 ba · 1,502 sq ft · built 1985

321 KIRKCALDY DRIVE, 32708

Highland Village 1 Winter Springs

Listing courtesy of COLDWELL BANKER REALTY

$349,900 New

3 bd · 2 ba · 1,153 sq ft · built 1982

1361 SAN DIEGO COURT, 32708

Sunrise Village

Listing courtesy of OFFERPAD BROKERAGE FL, LLC

$349,000 New

3 bd · 2 ba · 1,406 sq ft · built 1991

408 LANCERS DRIVE, 32708

Mount Greenwood Unit 5 Of

Listing courtesy of LA ROSA REALTY LLC

$329,000 New

3 bd · 2.5 ba · 1,680 sq ft · built 2007

472 HARBOR WINDS COURT, 32708

Harbor Winds

Listing courtesy of SAND DOLLAR REALTY GROUP INC

$749,900 New

4 bd · 3 ba · 2,520 sq ft · built 2003

475 VERANDAH COURT, 32708

Barrington Estates

Listing courtesy of COLDWELL BANKER REALTY

$449,000 New

4 bd · 2 ba · 2,498 sq ft · built 1989

3600 BISCAYNE DRIVE, 32708

Hollowbrook

Listing courtesy of LPT REALTY, LLC

$995,000 New

4 bd · 3 ba · 2,974 sq ft · built 1990

704 IRONWOOD COURT, 32708

Winter Springs

Listing courtesy of COLDWELL BANKER REALTY

$499,900 New

3 bd · 2 ba · 1,947 sq ft · built 2003

1013 WALNUT CREEK COVE, 32708

Parkstone

Listing courtesy of HOME SOLD NETWORK LLC

$365,000 New

2 bd · 2 ba · 1,289 sq ft · built 1987

725 ADIDAS ROAD, 32708

Wedgewood Tennis Villas

Listing courtesy of EXP REALTY LLC

$350,000 New

4 bd · 2 ba · 1,312 sq ft · built 1980

113 LIDO ROAD, 32708

Winter Springs

Listing courtesy of REDFIN CORPORATION

$1.08M New

5 bd · 5 ba · 4,001 sq ft · built 1996

149 CHERRY CREEK CIRCLE, 32708

Winter Springs

Listing courtesy of RE/MAX TOWN & COUNTRY REALTY

$725,000 New

4 bd · 2.5 ba · 2,701 sq ft · built 1983

992 SLEEPING ROCK COURT, 32708

Tuscawilla

Listing courtesy of RE/MAX PRIME PROPERTIES

$670,000 New

4 bd · 2.5 ba · 2,729 sq ft · built 1986

4161 ALDERGATE PLACE, 32708

Winter Springs

Listing courtesy of RE/MAX CENTRAL REALTY

Winter Springs homes for sale by price

Every active listing in Winter Springs grouped by price, with the newest listings in each band. The median is $419,900; the busiest band is $300K – $400K.

Under $200K: 9 homes

• $199,000 · 3 bd / 1 ba / 945 sq ft · 141 N EDGEMON AVENUE
• $175,000 · 2 bd / 1.5 ba / 1,108 sq ft · 284 WOODGREEN LANE
• $166,000 · 2 bd / 2 ba / 936 sq ft · 417 SHEOAH BOULEVARD #17
• $178,900 · 2 bd / 1.5 ba / 1,080 sq ft · 70 MOREE LOOP #61

$200K – $300K: 24 homes

• $205,000 · 2 bd / 2 ba / 1,224 sq ft · 499 CLUB DRIVE (Cypress Club)
• $285,000 · 3 bd / 2 ba / 1,161 sq ft · 526 SEASONS COURT
• $220,000 · 2 bd / 1.5 ba / 896 sq ft · 130 RHODEN LANE (Moss Place)
• $279,900 · 3 bd / 2 ba / 960 sq ft · 711 THISTLE PLACE

$300K – $400K: 39 homes

• $329,000 · 3 bd / 2.5 ba / 1,680 sq ft · 472 HARBOR WINDS COURT (Harbor Winds)
• $349,000 · 3 bd / 2 ba / 1,406 sq ft · 408 LANCERS DRIVE (Mount Greenwood Unit 5 Of)
• $349,900 · 3 bd / 2 ba / 1,153 sq ft · 1361 SAN DIEGO COURT (Sunrise Village)
• $350,000 · 2 bd / 2 ba / 1,502 sq ft · 321 KIRKCALDY DRIVE (Highland Village 1 Winter Springs)

$400K – $500K: 39 homes

• $419,900 · 3 bd / 2 ba / 1,510 sq ft · 1120 DAPPLED ELM LN LANE
• $489,000 · 3 bd / 2.5 ba / 1,680 sq ft · 154 WOODED VINE DRIVE (Tuskawilla Crossings 34'S)
• $449,000 · 4 bd / 2 ba / 2,498 sq ft · 3600 BISCAYNE DRIVE (Hollowbrook)
• $499,900 · 3 bd / 2 ba / 1,947 sq ft · 1013 WALNUT CREEK COVE (Parkstone)

$500K – $750K: 32 homes

• $550,000 · 3 bd / 2 ba / 1,735 sq ft · 766 ANDOVER CIRCLE
• $559,000 · 3 bd / 2 ba / 2,292 sq ft · 1008 FOREST CIRCLE
• $749,900 · 4 bd / 3 ba / 2,520 sq ft · 475 VERANDAH COURT (Barrington Estates)
• $520,000 · 4 bd / 2 ba / 2,123 sq ft · 734 SENECA MEADOWS ROAD

$750K – $1M: 7 homes

• $775,000 · 5 bd / 3.5 ba / 3,273 sq ft · 957 TALON PLACE (Northern Oaks)
• $849,900 · 4 bd / 3.5 ba / 2,597 sq ft · 1522 EAGLE NEST CIRCLE
• $925,000 · 5 bd / 3.5 ba / 3,521 sq ft · 609 VIANA COURT (Seville Chase)
• $995,000 · 4 bd / 3 ba / 2,974 sq ft · 704 IRONWOOD COURT

$1M and up: 5 homes

• $2.50M · 6 bd / 5 ba / 6,132 sq ft · 1447 BIRD ROAD (Talis Crossing)
• $1.08M · 5 bd / 5 ba / 4,001 sq ft · 149 CHERRY CREEK CIRCLE
• $1.20M · 5 bd / 3.5 ba / 2,700 sq ft · 1281 NATURES WAY
• $2.30M · 3 bd / 3 ba / 3,657 sq ft · 4910 E LAKE DRIVE

Every home for sale in Winter Springs right now (155)

All 155 active Winter Springs listings with a detail page, newest first, refreshed twice a day from the MLS.

• $205,000 · 2 bd / 2 ba / 1,224 sq ft · 499 CLUB DRIVE (Cypress Club)
• $2.50M · 6 bd / 5 ba / 6,132 sq ft · 1447 BIRD ROAD (Talis Crossing)
• $925,000 · 5 bd / 3.5 ba / 3,521 sq ft · 609 VIANA COURT (Seville Chase)
• $849,900 · 4 bd / 3.5 ba / 2,597 sq ft · 1522 EAGLE NEST CIRCLE
• $775,000 · 5 bd / 3.5 ba / 3,273 sq ft · 957 TALON PLACE (Northern Oaks)
• $559,000 · 3 bd / 2 ba / 2,292 sq ft · 1008 FOREST CIRCLE
• $550,000 · 3 bd / 2 ba / 1,735 sq ft · 766 ANDOVER CIRCLE
• $489,000 · 3 bd / 2.5 ba / 1,680 sq ft · 154 WOODED VINE DRIVE (Tuskawilla Crossings 34'S)
• $419,900 · 3 bd / 2 ba / 1,510 sq ft · 1120 DAPPLED ELM LN LANE
• $375,000 · 3 bd / 2 ba / 1,812 sq ft · 867 BENCHWOOD DRIVE
• $355,000 · 3 bd / 2 ba / 1,373 sq ft · 140 BOMBAY AVENUE
• $350,000 · 2 bd / 2 ba / 1,502 sq ft · 321 KIRKCALDY DRIVE (Highland Village 1 Winter Springs)
• $349,900 · 3 bd / 2 ba / 1,153 sq ft · 1361 SAN DIEGO COURT (Sunrise Village)
• $349,000 · 3 bd / 2 ba / 1,406 sq ft · 408 LANCERS DRIVE (Mount Greenwood Unit 5 Of)
• $329,000 · 3 bd / 2.5 ba / 1,680 sq ft · 472 HARBOR WINDS COURT (Harbor Winds)
• $749,900 · 4 bd / 3 ba / 2,520 sq ft · 475 VERANDAH COURT (Barrington Estates)
• $449,000 · 4 bd / 2 ba / 2,498 sq ft · 3600 BISCAYNE DRIVE (Hollowbrook)
• $995,000 · 4 bd / 3 ba / 2,974 sq ft · 704 IRONWOOD COURT
• $499,900 · 3 bd / 2 ba / 1,947 sq ft · 1013 WALNUT CREEK COVE (Parkstone)
• $365,000 · 2 bd / 2 ba / 1,289 sq ft · 725 ADIDAS ROAD (Wedgewood Tennis Villas)
• $350,000 · 4 bd / 2 ba / 1,312 sq ft · 113 LIDO ROAD
• $1.08M · 5 bd / 5 ba / 4,001 sq ft · 149 CHERRY CREEK CIRCLE
• $725,000 · 4 bd / 2.5 ba / 2,701 sq ft · 992 SLEEPING ROCK COURT (Tuscawilla)
• $670,000 · 4 bd / 2.5 ba / 2,729 sq ft · 4161 ALDERGATE PLACE
• $589,900 · 4 bd / 2 ba / 2,050 sq ft · 1230 STONE HARBOUR ROAD
• $525,000 · 4 bd / 2.5 ba / 2,181 sq ft · 4038 BISCAYNE DRIVE (Hollowbrook)
• $520,000 · 4 bd / 2 ba / 2,123 sq ft · 734 SENECA MEADOWS ROAD
• $499,000 · 4 bd / 3 ba / 2,268 sq ft · 855 BENCHWOOD DRIVE
• $485,000 · 5 bd / 3.5 ba / 1,986 sq ft · 627 CLEARN COURT
• $394,900 · 3 bd / 2 ba / 1,463 sq ft · 1024 DINERO DRIVE
• $340,000 · 2 bd / 2 ba / 1,560 sq ft · 672 NIGHTHAWK CIRCLE
• $199,000 · 3 bd / 1 ba / 945 sq ft · 141 N EDGEMON AVENUE
• $635,000 · 4 bd / 2.5 ba / 3,046 sq ft · 201 BURGESS DRIVE
• $285,000 · 3 bd / 2 ba / 1,161 sq ft · 526 SEASONS COURT
• $650,000 · 4 bd / 2 ba / 2,644 sq ft · 4901 PETRA COURT
• $415,000 · 3 bd / 2 ba / 1,632 sq ft · 1067 CHOKECHERRY DRIVE
• $399,000 · 3 bd / 3.5 ba / 1,932 sq ft · 1436 WINTER WHARF LANE (Jesups Landing)
• $350,000 · 3 bd / 2 ba / 1,784 sq ft · 615 PEARL ROAD
• $409,900 · 3 bd / 2 ba / 1,663 sq ft · 519 PLEASANT GROVE DRIVE
• $309,000 · 3 bd / 2 ba / 1,101 sq ft · 414 HORIZON DRIVE (Seasons The)
• $785,000 · 5 bd / 3.5 ba / 3,660 sq ft · 337 TWELVE OAKS DRIVE (winding hollow)
• $665,000 · 4 bd / 3 ba / 2,422 sq ft · 674 VISTAWILLA DRIVE
• $574,900 · 4 bd / 2.5 ba / 1,917 sq ft · 632 TUSKAWILLA POINT LANE (Tuskawilla Point)
• $399,000 · 3 bd / 2.5 ba / 1,476 sq ft · 1406 BLUMBERG BOULEVARD (Hickory Grove Twnhms)
• $465,000 · 3 bd / 2.5 ba / 1,732 sq ft · 45 HAYES ROAD
• $279,900 · 3 bd / 2 ba / 960 sq ft · 711 THISTLE PLACE
• $220,000 · 2 bd / 1.5 ba / 896 sq ft · 130 RHODEN LANE (Moss Place)
• $419,900 · 3 bd / 3.5 ba / 2,068 sq ft · 1380 MILL STREAM LANE (Jesups Landing)
• $269,900 · 3 bd / 2 ba / 1,366 sq ft · 700 CASTLEWOOD DRIVE
• $269,900 · 3 bd / 2 ba / 1,366 sq ft · 728 RIDGEWOOD WAY
• $464,000 · 3 bd / 2 ba / 1,919 sq ft · 619 CORAL WAY
• $699,000 · 4 bd / 3 ba / 2,272 sq ft · 864 BENTLEY GREEN CIRCLE (Bentley Club At Bentley Green)
• $569,999 · 4 bd / 2 ba / 1,985 sq ft · 943 MARCH HARE COURT
• $330,000 · 2 bd / 2.5 ba / 1,558 sq ft · 512 PINEBRANCH CIRCLE
• $206,499 · 2 bd / 1.5 ba / 898 sq ft · 131 KRISTI ANN COURT (Moss Cove)
• $969,000 · 5 bd / 3.5 ba / 3,014 sq ft · 1041 NORTHERN WAY
• $175,000 · 2 bd / 1.5 ba / 1,108 sq ft · 284 WOODGREEN LANE
• $234,900 · 2 bd / 2.5 ba / 1,156 sq ft · 611 CASA PARK A COURT
• $210,000 · 2 bd / 1.5 ba / 898 sq ft · 113 KRISTI ANN COURT (Moss Cove)
• $497,500 · 4 bd / 3 ba / 2,256 sq ft · 909 DEVON CREEK ROAD (Parkstone)
• $486,900 · 4 bd / 2.5 ba / 1,992 sq ft · 1610 FOX GLEN COURT (Fox Glen At Chelsea Parc Tuscawilla)
• $442,000 · 3 bd / 2 ba / 1,450 sq ft · 107 PEREGRINE COURT
• $359,900 · 3 bd / 2 ba / 1,238 sq ft · 1350 PALO ALTO COURT (Sunrise Village)
• $166,000 · 2 bd / 2 ba / 936 sq ft · 417 SHEOAH BOULEVARD #17
• $410,000 · 3 bd / 2 ba / 1,748 sq ft · 205 INKWOOD COURT
• $350,000 · 3 bd / 2 ba / 1,616 sq ft · 717 LANCEWOOD DRIVE
• $239,900 · 2 bd / 1.5 ba / 1,156 sq ft · 1307 PARK VILLA PLACE
• $599,000 · 3 bd / 2.5 ba / 2,272 sq ft · 116 PARTRIDGE CIRCLE
• $549,000 · 3 bd / 3.5 ba / 2,523 sq ft · 1166 SPOTTED SANDPIPER LOOP
• $490,000 · 4 bd / 3 ba / 2,300 sq ft · 1142 ODAY DRIVE
• $409,000 · 3 bd / 2 ba / 1,658 sq ft · 744 BARRINGTON CIRCLE
• $499,999 · 3 bd / 2.5 ba / 1,732 sq ft · 1010 W PEBBLE BEACH CIRCLE
• $434,900 · 3 bd / 2 ba / 2,116 sq ft · 1298 MADELENA AVENUE
• $369,500 · 3 bd / 3.5 ba / 1,854 sq ft · 412 BLUE BAYOU LANE (Jesups Reserve Twnhms Rep)
• $559,900 · 4 bd / 3.5 ba / 2,566 sq ft · 731 SENECA MEADOWS ROAD (Parkstone)
• $450,000 · 3 bd / 2 ba / 1,700 sq ft · 288 RINGWOOD DRIVE
• $322,500 · 3 bd / 2 ba / 1,201 sq ft · 654 CYPRESS LANE
• $825,000 · 6 bd / 5 ba / 4,251 sq ft · 224 HUNTRIDGE WAY
• $505,000 · 3 bd / 2.5 ba / 1,702 sq ft · 1378 TARFLOWER DRIVE (Hickory Grove Twnhms)
• $344,900 · 3 bd / 2.5 ba / 1,605 sq ft · 1482 CREEKSIDE CIRCLE
• $520,000 · 4 bd / 2 ba / 1,941 sq ft · 324 RINGWOOD CIRCLE
• $439,900 · 3 bd / 2.5 ba / 1,730 sq ft · 625 PEARL ROAD
• $489,000 · 4 bd / 2.5 ba / 2,309 sq ft · 131 LISA LOOP (The Oaks Sub)
• $349,000 · 3 bd / 2 ba / 1,168 sq ft · 203 COTTONWOOD DRIVE
• $515,000 · 4 bd / 2 ba / 1,931 sq ft · 699 N ENDEAVOUR DRIVE
• $289,900 · 3 bd / 2.5 ba / 1,468 sq ft · 162 CONSTITUTION WAY (Heritage Park Twnhms)
• $284,000 · 3 bd / 2 ba / 1,101 sq ft · 412 HORIZON DRIVE
• $429,000 · 3 bd / 2 ba / 1,484 sq ft · 1714 FOX GLEN COURT (Fox Glen At Chelsea Parc Tuscawilla)
• $374,400 · 3 bd / 3 ba / 1,583 sq ft · 662 NIGHTHAWK CIRCLE (Greenspointe)
• $339,900 · 3 bd / 2.5 ba / 1,602 sq ft · 617 PINEBRANCH CIRCLE
• $435,000 · 3 bd / 2 ba / 1,887 sq ft · 806 BIG BUCK CIRCLE
• $425,000 · 3 bd / 2 ba / 1,574 sq ft · 1162 E WINGED FOOT CIRCLE
• $595,000 · 4 bd / 3 ba / 2,840 sq ft · 248 HUNTRIDGE WAY
• $178,900 · 2 bd / 1.5 ba / 1,080 sq ft · 70 MOREE LOOP #61
• $394,900 · 3 bd / 2 ba / 1,695 sq ft · 1224 ANDES DR
• $244,999 · 2 bd / 1.5 ba / 1,156 sq ft · 1453 CASA PARK CIRCLE
• $429,900 · 3 bd / 2 ba / 1,587 sq ft · 998 WHITE SPRINGS LANE
• $365,500 · 3 bd / 2 ba / 1,368 sq ft · 101 S FLAMINGO AVENUE (North Orlando 2Nd Add)
• $475,000 · 3 bd / 2 ba / 1,978 sq ft · 133 REDTAIL PLACE
• $199,000 · 3 bd / 2 ba / 1,187 sq ft · 429 SHEOAH BOULEVARD #9 (Baytree Village)
• $360,000 · 2 bd / 2 ba / 1,193 sq ft · 923 TORREY PINE DRIVE
• $600,000 · 5 bd / 3 ba / 2,523 sq ft · 1015 ANTELOPE TRAIL
• $525,000 · 4 bd / 3.5 ba / 2,164 sq ft · 424 FLATWOOD DRIVE
• $539,000 · 4 bd / 2 ba / 2,066 sq ft · 1114 SEAFARER LANE
• $665,000 · 4 bd / 3 ba / 2,724 sq ft · 223 BLUE CREEK DRIVE
• $369,900 · 4 bd / 3 ba / 1,680 sq ft · 212 S CORTEZ AVENUE
• $525,000 · 5 bd / 3 ba / 2,852 sq ft · 811 MAPLE LEAF LOOP
• $374,900 · 3 bd / 2 ba / 1,210 sq ft · 629 ALTON ROAD
• $605,000 · 5 bd / 2 ba / 2,355 sq ft · 216 TAVESTOCK LOOP (Parkstone)
• $379,000 · 4 bd / 3 ba / 2,150 sq ft · 758 N GRETNA COURT
• $529,900 · 3 bd / 2 ba / 1,616 sq ft · 1329 AUGUSTA NATIONAL BOULEVARD
• $499,000 · 4 bd / 2 ba / 2,056 sq ft · 1389 PONCE DE LEON BOULEVARD
• $387,500 · 3 bd / 3.5 ba / 1,872 sq ft · 227 MCLEODS WAY (Jesups Reserve Twnhms Rep)
• $489,900 · 2 bd / 2.5 ba / 1,926 sq ft · 1541 CORKERY COURT #1541 (Greens At Tuscawilla)
• $475,000 · 3 bd / 2 ba / 1,665 sq ft · 1055 CHESTERFIELD CIRCLE
• $355,000 · 4 bd / 2 ba / 1,425 sq ft · 142 BAYBERRY COURT
• $297,000 · 3 bd / 2 ba / 1,318 sq ft · 207 BIRCH TERRACE (North Orlando Terrace)
• $420,000 · 3 bd / 2 ba / 1,831 sq ft · 963 SEQUOIA DRIVE
• $214,000 · 2 bd / 1 ba / 1,148 sq ft · 120 N FAIRFAX AVENUE
• $424,990 · 4 bd / 2.5 ba / 1,678 sq ft · 221 SPINDLE PALM COVE (Hickory Grove)
• $344,000 · 3 bd / 2.5 ba / 1,792 sq ft · 830 DUNBAR TERRACE
• $225,000 · 2 bd / 2.5 ba / 1,156 sq ft · 605 CASA PARK COURT #H
• $399,900 · 2 bd / 2 ba / 1,812 sq ft · 717 ADIDAS ROAD (Wedgewood Tennis Villas)
• $389,900 · 3 bd / 2 ba / 1,609 sq ft · 1012 FOREST CIRCLE
• $140,000 · 1 bd / 1 ba / 710 sq ft · 220 MOREE LOOP #2 (Baytree Village)
• $384,000 · 3 bd / 2.5 ba / 1,606 sq ft · 1357 MILL STREAM LANE (Jesups Landing)
• $244,000 · 2 bd / 1.5 ba / 1,363 sq ft · 498 GREEN SPRING CIR
• $154,950 · 2 bd / 2 ba / 972 sq ft · 50 SHEOAH BOULEVARD #33
• $276,200 · 2 bd / 2.5 ba / 1,330 sq ft · 4113 HEDGE MAPLE PLACE (Heritage Commons)
• $475,000 · 3 bd / 2 ba / 1,857 sq ft · 629 RYAN COURT
• $272,000 · 3 bd / 2 ba / 1,425 sq ft · 600 NORTHERN WAY #1608
• $499,000 · 4 bd / 2.5 ba / 1,922 sq ft · 440 BUCKSKIN COURT
• $474,900 · 4 bd / 2.5 ba / 2,152 sq ft · 1304 ORTEGA STREET
• $557,900 · 4 bd / 2.5 ba / 2,415 sq ft · 268 TAVESTOCK LOOP (Parkstone)
• $349,900 · 3 bd / 2 ba / 1,161 sq ft · 108 SUNDANCE COURT (The Seasons Winter Springs)
• $324,900 · 3 bd / 2 ba / 1,178 sq ft · 335 KIRKCALDY DRIVE (Highland Village 1 Winter Springs)
• $1.20M · 5 bd / 3.5 ba / 2,700 sq ft · 1281 NATURES WAY
• $2.30M · 3 bd / 3 ba / 3,657 sq ft · 4910 E LAKE DRIVE
• $275,000 · 3 bd / 2.5 ba / 1,326 sq ft · 299 WOODGREEN LANE
• $170,000 · 3 bd / 2 ba / 1,187 sq ft · 240 MOREE LOOP #3 (Baytree Village)
• $479,000 · 3 bd / 2 ba / 1,978 sq ft · 107 GOLDEN CREST COURT
• $250,000 · 3 bd / 2 ba / 1,460 sq ft · 476 CLUB DRIVE (Cypress Club)
• $647,500 · 4 bd / 3 ba / 2,509 sq ft · 156 SEVILLE CHASE DRIVE (Seville Chase)
• $455,000 · 4 bd / 3.5 ba / 2,344 sq ft · 1128 SPOTTED SANDPIPER LOOP (Seminole Crossing Twnhms)
• $274,900 · 3 bd / 2 ba / 1,425 sq ft · 600 NORTHERN WAY #201
• $285,000 · 3 bd / 2 ba / 1,069 sq ft · 421 HORIZON DRIVE (Seasons The)
• $484,900 · 4 bd / 2.5 ba / 1,996 sq ft · 632 BLENHEIM LOOP
• $569,000 · 4 bd / 2.5 ba / 2,674 sq ft · 30 SABLE COURT
• $309,777 · 3 bd / 2 ba / 1,574 sq ft · 1053 W PEBBLE BEACH CIRCLE
• $242,000 · 3 bd / 2 ba / 1,089 sq ft · 270 SAN GABRIEL STREET (Deersong 2 Winter Springs)

Showing the newest 150 of 155; the price bands above and the map cover the rest.

Homes for sale in Winter Springs by ZIP code

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

Winter Springs communities with the most homes for sale

The Winter Springs 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 Winter Springs: property types

• Single-family houses: 115
• Townhouses: 32
• Condos: 8

Browse by type: Condos for sale in Winter Springs (8) · Townhomes for sale in Winter Springs (32).

The Winter Springs real estate market right now

Over the last 12 months 267 homes sold in Winter Springs at a median of $444,997 (-1.6% year over year), $243 per square foot. Sellers received 96% of list price and homes took a median 33 days to go under contract. With 155 homes for sale against that sales pace, months of supply is 7.0, a buyer’s market by the six-month rule. Cash buyers accounted for 20% of sales. New construction was 5% of sales.

Winter Springs supply by price band

Winter Springs 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 Winter Springs costs to own

Take the median $419,900 listing with 20% down at today’s 7.40% 30-year rate: principal and interest run about $2,326/month. Seminole County’s typical millage of 15.18 puts property tax near $5,615/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 Seminole County is about $1,572/year; newer roofs and inland addresses usually quote below it. All in, plan on roughly $2,925/month plus any HOA or CDD assessment.

Explore Winter Springs

• All homes for sale in Seminole County, FL
• What is my house worth in Winter Springs? Home values, $/sq ft and days to contract
• 4-bedroom homes for sale in Winter Springs
• Homes under $300K in Winter Springs
• Homes from $300K to $500K in Winter Springs
• Winter Springs pool homes for sale
• Gated communities in Winter Springs
• New listings this week in Winter Springs
• Price reductions this week in Winter Springs
• Winter Springs homes by street
• What $500K buys in Seminole County
• Winter Springs market intelligence: prices, supply and trends
• Moving to Winter Springs: the data guide
• Cost of living in Winter Springs
• Best neighborhoods in Winter Springs
• Seminole County property tax guide
• Seminole County down payment assistance limits
• First-time home buyer guide for Florida
• Search every Winter Springs community
• Best places to live in Florida: every city ranked by the numbers
• All Florida cities and counties

Homes for sale near Winter Springs

• Homes for sale in Sanford, FL — 464 listings
• Homes for sale in Altamonte Springs, FL — 340 listings
• Homes for sale in Longwood, FL — 224 listings
• Homes for sale in Lake Mary, FL — 218 listings
• Homes for sale in Oviedo, FL — 209 listings
• Homes for sale in Casselberry, FL — 134 listings
• Homes for sale in Geneva, FL — 25 listings
• Homes for sale in Chuluota, FL — 21 listings
• Homes for sale in Fern Park, FL — 13 listings

Recently off market in Winter Springs

Homes in Winter Springs 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.

• 736 Summerland Drive · last listed $295,900 · off market Oct 14, 2026
• 1329 Heritage Commons Drive · last listed $287,500 · off market Oct 14, 2026
• 702 Glasgow Court · last listed $301,000 · off market Oct 11, 2026
• 655 Nighthawk Circle · last listed $365,000 · off market Oct 9, 2026
• 1838 Seneca Blvd · last listed $674,900 · off market Oct 9, 2026
• 1452 King Court · last listed $360,000 · off market Oct 9, 2026
• 661 Andover Cir · off market Oct 8, 2026
• 200 Blue Creek Drive · last listed $625,000 · off market Oct 8, 2026
• 1035 N Elk Ct · off market Oct 8, 2026
• 504 Green Spring Circle · last listed $235,000 · off market Oct 6, 2026
• 4951 Courtland Loop · last listed $650,000 · off market Oct 6, 2026
• 518 Harbor Winds Court · last listed $335,000 · off market Oct 5, 2026

Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Winter Springs as of 2026-10-15 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.