Homes for Sale in Winter Park, FL

By Jon Brooks, Co-Founder, Momentum Realty · Updated November 13, 2026

394 homes are for sale in Winter Park, FL as of 2026-11-13, with 18 more under contract. The median list price is $636,250 ($343/sq ft), most homes list between $210K to $2.80M, and the median listing has been on the market 60 days. That is 260 houses, 95 condos and 39 townhouses. 36 homes came on the market this week and 887 sold in the last 12 months at a median of $499,000.

Browse all 418 homes for sale in Winter Park, FL — the complete list, newest first.

Newest homes for sale in Winter Park

The most recently listed homes in Winter Park, 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.

$1.73M New

4 bd · 4 ba · 3,594 sq ft · built 1960

1641 HIBISCUS AVENUE, 32789

Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES

$415,000 New

3 bd · 2 ba · 1,440 sq ft · built 1959

2821 CHANTILLY AVENUE, 32789

Winter Park Manor

Listing courtesy of RISE REALTY OF FLORIDA LLC

$1.85M New

4 bd · 5 ba · 2,675 sq ft · built 2026

2507 LAFAYETTE AVENUE, 32789

Winter Park Village

Listing courtesy of ONE LUXURY INTERNATIONAL LLC

$849,999 New

3 bd · 2.5 ba · 2,052 sq ft · built 1987

775 MCINTYRE AVENUE #9, 32789

Winter Park

Listing courtesy of PARKSIDE PROPERTIES, LLC

$449,000 New

3 bd · 2 ba · 1,577 sq ft · built 1983

3148 NICHOLSON DRIVE, 32792

Wrenwood Unit 3 4Th Add

Listing courtesy of HOMEVEST REALTY

$2.19M New

5 bd · 4.5 ba · 4,213 sq ft · built 1999

304 SANTIAGO DRIVE, 32789

Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES

$1.10M New

3 bd · 3 ba · 2,626 sq ft · built 1955

531 WORTHINGTON DRIVE, 32789

Kenilworth Shores

Listing courtesy of FANNIE HILLMAN & ASSOCIATES

$968,000 New

5 bd · 3.5 ba · 3,600 sq ft · built 1985

1400 PELICAN BAY TRAIL, 32792

Winter Park

Listing courtesy of ABSOLUTE REALTY GROUP, LLC

$629,500 New

2 bd · 2 ba · 858 sq ft · built 1955

640 N PARK AVENUE #26, 32790

Park Aire Condo

Listing courtesy of MICHAEL O'SHAUGHNESSY, INC.

$499,000 New

4 bd · 1.5 ba · 1,470 sq ft · built 1956

1934 TAYLOR AVENUE, 32792

Eastgate Sub Winter Park

Listing courtesy of KELLER WILLIAMS REALTY AT THE PARKS

$485,000 New

2 bd · 2 ba · 970 sq ft · built 1972

535 N INTERLACHEN AVENUE #302, 32789

Andalucia Apts

Listing courtesy of FANNIE HILLMAN & ASSOCIATES

$450,000 New

3 bd · 2 ba · 1,511 sq ft · built 1955

2885 ROXBURY ROAD, 32789

Winter Park

Listing courtesy of COLDWELL BANKER REALTY

$177,000 New

1 bd · 1 ba · 759 sq ft · built 1981

662 TRINIDAD COURT #662, 32792

Winter Park Villas

Listing courtesy of CLARA HERRERA REALTY

$739,000 New

3 bd · 2.5 ba · 2,069 sq ft · built 1981

1140 WASHINGTON AVENUE #16C, 32789

Winter Park

Listing courtesy of CHEVON EATON

$417,000 New

4 bd · 3 ba · 1,714 sq ft · built 1980

1386 CLEMATIS LANE, 32792

Winter Park

Listing courtesy of EMPIRE REALTY & MANAGEMENT SERVICES

$1.65M New

4 bd · 3.5 ba · 2,754 sq ft · built 2018

1900 SUNSET DRIVE, 32789

Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES

$479,900 New

3 bd · 2 ba · 1,647 sq ft · built 1972

7536 VILLAGE GREEN DRIVE, 32792

Winter Park

Listing courtesy of RE/MAX TOWN & COUNTRY REALTY

$849,000 New

3 bd · 2 ba · 2,003 sq ft · built 1981

1507 GOLFSIDE DRIVE, 32792

Greenview At Winter Pines

Listing courtesy of LPT REALTY, LLC

$569,900 New

3 bd · 2 ba · 1,824 sq ft · built 1954

2141 LAKE DRIVE, 32789

Winter Park

Listing courtesy of SHORES REAL ESTATE

$530,000 New

3 bd · 2 ba · 1,385 sq ft · built 1960

510 FITZWALTER DRIVE, 32792

Winter Park

Listing courtesy of FANNIE HILLMAN & ASSOCIATES

$460,000 New

3 bd · 2.5 ba · 2,076 sq ft · built 2020

2356 SHADOWLAND LOOP, 32792

Winter Park

Listing courtesy of KELLER WILLIAMS WINTER PARK

$435,000 New

3 bd · 2.5 ba · 2,027 sq ft · built 1990

5415 N LAKE BURKETT LANE, 32792

Winter Park

Listing courtesy of KELLER WILLIAMS WINTER PARK

$425,000 New

3 bd · 2 ba · 1,495 sq ft · built 1981

3157 SHADY PINE AVENUE, 32792

Bel Aire Pines

Listing courtesy of MID-STATE PROPERTIES PSL LLC

$399,000 New

2 bd · 1 ba · 959 sq ft · built 1955

2176 CRANDON AVENUE, 32789

Olympia Heights Annex

Listing courtesy of CORCORAN PREMIER REALTY

Winter Park homes for sale by price

Every active listing in Winter Park grouped by price, with the newest listings in each band. The median is $636,250; the busiest band is $1M and up.

Under $200K: 38 homes

• $177,000 · 1 bd / 1 ba / 759 sq ft · 662 TRINIDAD COURT #662 (Winter Park Villas)
• $139,998 · 1 bd / 1 ba / 749 sq ft · 3019 ANTIQUE OAKS CIRCLE #127 (Parkview Village)
• $175,000 · 1 bd / 1 ba / 727 sq ft · 200 ST ANDREWS BOULEVARD #906
• $169,999 · 2 bd / 2.5 ba / 1,090 sq ft · 3027 AARON BUR AVENUE #L1 (Colonies)

$200K – $300K: 40 homes

• $295,000 · 2 bd / 2 ba / 1,074 sq ft · 700 MELROSE AVENUE #B23 (Winter Park Gardens Condo)
• $299,000 · 2 bd / 2 ba / 1,032 sq ft · 170 BALFOUR DRIVE #1
• $249,000 · 3 bd / 2 ba / 1,345 sq ft · 4940 TANGERINE AVENUE #4940 (Wrenwood Condominium)
• $280,000 · 2 bd / 2 ba / 1,495 sq ft · 2352 SUN VALLEY CIRCLE

$300K – $400K: 41 homes

• $399,000 · 2 bd / 1 ba / 959 sq ft · 2176 CRANDON AVENUE (Olympia Heights Annex)
• $325,000 · 3 bd / 2.5 ba / 1,628 sq ft · 1462 SICILIANO POINT
• $325,000 · 3 bd / 2 ba / 1,783 sq ft · 2535 LEEWARD WAY
• $310,000 · 2 bd / 2 ba / 1,074 sq ft · 700 MELROSE AVENUE #A22 (Winter Park Gardens Condo)

$400K – $500K: 50 homes

• $415,000 · 3 bd / 2 ba / 1,440 sq ft · 2821 CHANTILLY AVENUE (Winter Park Manor)
• $449,000 · 3 bd / 2 ba / 1,577 sq ft · 3148 NICHOLSON DRIVE (Wrenwood Unit 3 4Th Add)
• $450,000 · 3 bd / 2 ba / 1,511 sq ft · 2885 ROXBURY ROAD
• $485,000 · 2 bd / 2 ba / 970 sq ft · 535 N INTERLACHEN AVENUE #302 (Andalucia Apts)

$500K – $750K: 57 homes

• $629,500 · 2 bd / 2 ba / 858 sq ft · 640 N PARK AVENUE #26 (Park Aire Condo)
• $739,000 · 3 bd / 2.5 ba / 2,069 sq ft · 1140 WASHINGTON AVENUE #16C
• $530,000 · 3 bd / 2 ba / 1,385 sq ft · 510 FITZWALTER DRIVE
• $569,900 · 3 bd / 2 ba / 1,824 sq ft · 2141 LAKE DRIVE

$750K – $1M: 38 homes

• $849,999 · 3 bd / 2.5 ba / 2,052 sq ft · 775 MCINTYRE AVENUE #9
• $968,000 · 5 bd / 3.5 ba / 3,600 sq ft · 1400 PELICAN BAY TRAIL
• $849,000 · 3 bd / 2 ba / 2,003 sq ft · 1507 GOLFSIDE DRIVE (Greenview At Winter Pines)
• $895,000 · 3 bd / 2.5 ba / 2,170 sq ft · 1118 WASHINGTON AVENUE #5C

$1M and up: 130 homes

• $1.73M · 4 bd / 4 ba / 3,594 sq ft · 1641 HIBISCUS AVENUE
• $1.85M · 4 bd / 5 ba / 2,675 sq ft · 2507 LAFAYETTE AVENUE (Winter Park Village)
• $1.10M · 3 bd / 3 ba / 2,626 sq ft · 531 WORTHINGTON DRIVE (Kenilworth Shores)
• $2.19M · 5 bd / 4.5 ba / 4,213 sq ft · 304 SANTIAGO DRIVE

Every home for sale in Winter Park right now (394)

All 394 active Winter Park listings with a detail page, newest first, refreshed twice a day from the MLS.

• $1.73M · 4 bd / 4 ba / 3,594 sq ft · 1641 HIBISCUS AVENUE
• $415,000 · 3 bd / 2 ba / 1,440 sq ft · 2821 CHANTILLY AVENUE (Winter Park Manor)
• $1.85M · 4 bd / 5 ba / 2,675 sq ft · 2507 LAFAYETTE AVENUE (Winter Park Village)
• $849,999 · 3 bd / 2.5 ba / 2,052 sq ft · 775 MCINTYRE AVENUE #9
• $449,000 · 3 bd / 2 ba / 1,577 sq ft · 3148 NICHOLSON DRIVE (Wrenwood Unit 3 4Th Add)
• $2.19M · 5 bd / 4.5 ba / 4,213 sq ft · 304 SANTIAGO DRIVE
• $1.10M · 3 bd / 3 ba / 2,626 sq ft · 531 WORTHINGTON DRIVE (Kenilworth Shores)
• $968,000 · 5 bd / 3.5 ba / 3,600 sq ft · 1400 PELICAN BAY TRAIL
• $629,500 · 2 bd / 2 ba / 858 sq ft · 640 N PARK AVENUE #26 (Park Aire Condo)
• $499,000 · 4 bd / 1.5 ba / 1,470 sq ft · 1934 TAYLOR AVENUE (Eastgate Sub Winter Park)
• $485,000 · 2 bd / 2 ba / 970 sq ft · 535 N INTERLACHEN AVENUE #302 (Andalucia Apts)
• $450,000 · 3 bd / 2 ba / 1,511 sq ft · 2885 ROXBURY ROAD
• $177,000 · 1 bd / 1 ba / 759 sq ft · 662 TRINIDAD COURT #662 (Winter Park Villas)
• $739,000 · 3 bd / 2.5 ba / 2,069 sq ft · 1140 WASHINGTON AVENUE #16C
• $417,000 · 4 bd / 3 ba / 1,714 sq ft · 1386 CLEMATIS LANE
• $1.65M · 4 bd / 3.5 ba / 2,754 sq ft · 1900 SUNSET DRIVE
• $479,900 · 3 bd / 2 ba / 1,647 sq ft · 7536 VILLAGE GREEN DRIVE
• $849,000 · 3 bd / 2 ba / 2,003 sq ft · 1507 GOLFSIDE DRIVE (Greenview At Winter Pines)
• $569,900 · 3 bd / 2 ba / 1,824 sq ft · 2141 LAKE DRIVE
• $530,000 · 3 bd / 2 ba / 1,385 sq ft · 510 FITZWALTER DRIVE
• $460,000 · 3 bd / 2.5 ba / 2,076 sq ft · 2356 SHADOWLAND LOOP
• $435,000 · 3 bd / 2.5 ba / 2,027 sq ft · 5415 N LAKE BURKETT LANE
• $425,000 · 3 bd / 2 ba / 1,495 sq ft · 3157 SHADY PINE AVENUE (Bel Aire Pines)
• $399,000 · 2 bd / 1 ba / 959 sq ft · 2176 CRANDON AVENUE (Olympia Heights Annex)
• $2.75M · 4 bd / 5 ba / 3,640 sq ft · 1663 N PARK AVENUE
• $745,000 · 2 bd / 1.5 ba / 897 sq ft · 640 N PARK AVENUE #3
• $650,000 · 3 bd / 2 ba / 1,594 sq ft · 1401 PELHAM ROAD
• $620,000 · 3 bd / 2 ba / 1,762 sq ft · 624 DUNRAVEN DRIVE
• $480,000 · 3 bd / 2 ba / 1,768 sq ft · 1735 MEADOWGOLD LANE
• $450,000 · 3 bd / 2 ba / 1,346 sq ft · 506 LANDER ROAD
• $450,000 · 4 bd / 2.5 ba / 1,866 sq ft · 239 ORANGE TERRACE DRIVE
• $5.70M · 4 bd / 3.5 ba / 4,725 sq ft · 541 VIRGINIA DRIVE
• $739,000 · 4 bd / 3.5 ba / 2,553 sq ft · 2315 KESTREL PERCH PLACE
• $299,000 · 2 bd / 2 ba / 1,032 sq ft · 170 BALFOUR DRIVE #1
• $295,000 · 2 bd / 2 ba / 1,074 sq ft · 700 MELROSE AVENUE #B23 (Winter Park Gardens Condo)
• $139,998 · 1 bd / 1 ba / 749 sq ft · 3019 ANTIQUE OAKS CIRCLE #127 (Parkview Village)
• $1.95M · 4 bd / 3.5 ba / 3,450 sq ft · 1398 GROVE TERRACE (Sylvan Lake Shores)
• $1.62M · 3 bd / 2.5 ba / 2,884 sq ft · 345 BELOIT AVENUE
• $895,000 · 3 bd / 2.5 ba / 2,170 sq ft · 1118 WASHINGTON AVENUE #5C
• $650,000 · 3 bd / 2.5 ba / 1,798 sq ft · 1261 MICHIGAN AVENUE (Park Shore)
• $550,000 · 3 bd / 2 ba / 1,610 sq ft · 257 LINCOLNSHIRE ROAD
• $175,000 · 1 bd / 1 ba / 727 sq ft · 200 ST ANDREWS BOULEVARD #906
• $850,000 · 4 bd / 3 ba / 2,301 sq ft · 870 N PHELPS AVENUE
• $325,000 · 3 bd / 2.5 ba / 1,628 sq ft · 1462 SICILIANO POINT
• $5.95M · 5 bd / 6 ba / 5,796 sq ft · 1441 GROVE TERRACE (Sylvan Lake Shores)
• $1.05M · 4 bd / 3 ba / 2,787 sq ft · 1735 DEMETREE DRIVE
• $650,000 · 4 bd / 2.5 ba / 1,770 sq ft · 1458 LONE FEATHER TRAIL
• $325,000 · 3 bd / 2 ba / 1,783 sq ft · 2535 LEEWARD WAY
• $1.50M · 4 bd / 3.5 ba / 3,478 sq ft · 1350 LYNDALE BOULEVARD
• $310,000 · 2 bd / 2 ba / 1,074 sq ft · 700 MELROSE AVENUE #A22 (Winter Park Gardens Condo)
• $4.00M · 3 bd / 4 ba / 3,885 sq ft · 125 S INTERLACHEN AVENUE #4
• $2.45M · 5 bd / 4.5 ba / 3,391 sq ft · 1441 PALM AVENUE (Lake Knowles Terrace Add 02)
• $1.43M · 4 bd / 4.5 ba / 3,563 sq ft · 2237 WOODCREST DRIVE (Kenilworth Estates)
• $1.38M · 4 bd / 3.5 ba / 2,984 sq ft · 1534 MILLER AVENUE (Lawndale)
• $849,900 · 4 bd / 3 ba / 2,434 sq ft · 2011 HARMON AVENUE (Lawndale)
• $635,000 · 3 bd / 2.5 ba / 2,015 sq ft · 565 HUNTINGTON AVENUE #565
• $439,000 · 3 bd / 2 ba / 1,631 sq ft · 7640 VILLAGE GREEN DR
• $410,000 · 3 bd / 2 ba / 1,300 sq ft · 1935 AZALEA AVENUE (Temple Terrace Annex)
• $399,500 · 3 bd / 2 ba / 1,360 sq ft · 2038 PONDEROSA AVENUE
• $385,000 · 3 bd / 2 ba / 1,305 sq ft · 7361 GRAND AVENUE
• $249,000 · 3 bd / 2 ba / 1,345 sq ft · 4940 TANGERINE AVENUE #4940 (Wrenwood Condominium)
• $1.18M · 3 bd / 3 ba / 2,096 sq ft · 1500 HARRIS CIRCLE (Sylvan Lake Shores)
• $450,000 · 5 bd / 3 ba / 1,636 sq ft · 1825 CHILEAN LANE
• $359,900 · 3 bd / 2 ba / 1,208 sq ft · 2168 RIDGE DRIVE (Ridge High 1St Add)
• $320,000 · 3 bd / 2 ba / 1,156 sq ft · 148 OAK GROVE RD
• $169,999 · 2 bd / 2.5 ba / 1,090 sq ft · 3027 AARON BUR AVENUE #L1 (Colonies)
• $280,000 · 2 bd / 2 ba / 1,495 sq ft · 2352 SUN VALLEY CIRCLE
• $375,000 · 3 bd / 2 ba / 1,674 sq ft · 1830 GLADIOLAS DRIVE
• $270,000 · 3 bd / 2.5 ba / 1,580 sq ft · 7463 CANFORD COURT #15 (Whisperwood Condo)
• $6.00M · 5 bd / 5.5 ba / 5,476 sq ft · 1200 VIA SALERNO (Cloister Grove Sub Winter Park)
• $1.32M · 4 bd / 3.5 ba / 3,474 sq ft · 952 MOSS LANE
• $1.19M · 4 bd / 3.5 ba / 5,519 sq ft · 1940 MAGNOLIA AVENUE (Temple Terrace Annex)
• $399,900 · 4 bd / 2 ba / 1,427 sq ft · 603 CARNATION DRIVE (Eastbrook Sub)
• $170,000 · 1 bd / 1 ba / 793 sq ft · 200 SAINT ANDREWS BOULEVARD #3408
• $985,000 · 5 bd / 3 ba / 3,296 sq ft · 2330 WESTMINSTER CT. (Glencoe Sub Winter Park)
• $375,000 · 4 bd / 2.5 ba / 1,776 sq ft · 2189 SUSSEX ROAD
• $4.50M · 5 bd / 5.5 ba / 4,754 sq ft · 1631 HILLCREST AVENUE (Ellno Willo)
• $699,900 · 3 bd / 2 ba / 1,666 sq ft · 1884 JESSICA COURT (Waterbridge)
• $575,000 · 3 bd / 2 ba / 1,804 sq ft · 1399 ALOMA AVENUE
• $509,999 · 3 bd / 2 ba / 1,460 sq ft · 808 DENSMORE DRIVE (Winter Park Estates)
• $305,000 · 3 bd / 1 ba / 1,216 sq ft · 2640 BEVERLY AVENUE
• $188,800 · 2 bd / 2 ba / 1,058 sq ft · 4832 TANGERINE AVENUE #4832 (Wrenwood Condominium)
• $3.19M · 4 bd / 5 ba / 4,311 sq ft · 1825 WHITEHALL DRIVE (Kenilworth Shores)
• $695,000 · 2 bd / 2.5 ba / 1,801 sq ft · 2887 TEMPLE TRAIL
• $415,000 · 3 bd / 2 ba / 1,187 sq ft · 2126 ALBERT LEE PARKWAY
• $399,900 · 3 bd / 2 ba / 1,247 sq ft · 5405 JUSTINE WAY (Wrenwood Unit 3 4Th Add)
• $314,000 · 3 bd / 2 ba / 1,229 sq ft · 1740 PURITAN AVENUE
• $299,000 · 3 bd / 2.5 ba / 1,602 sq ft · 5468 BRACKEN COURT
• $220,000 · 2 bd / 2 ba / 1,281 sq ft · 4786 TANGERINE AVENUE #4786 (Wrenwood Condominium)
• $4.70M · 11 bd / 7.5 ba / 3,615 sq ft · 617 N INTERLACHEN AVENUE (Winter Park Villas)
• $3.50M · 5 bd / 5.5 ba / 4,483 sq ft · 1600 LEGION DRIVE (Green Oaks Rep Winter Park)
• $2.63M · 5 bd / 4.5 ba / 3,682 sq ft · 1681 WOODLAND AVENUE (Comstock Park)
• $1.35M · 4 bd / 3.5 ba / 2,575 sq ft · 1939 WOODCREST DRIVE
• $750,000 · 5 bd / 3.5 ba / 3,496 sq ft · 8061 PLEASANT PINE CIRCLE (Enclave At Aloma)
• $6.00M · 5 bd / 6 ba / 4,806 sq ft · 1011 MCKEAN CIRCLE (Palmer Park)
• $1.25M · 6 bd / 5.5 ba / 5,021 sq ft · 1445 VIA SANGRO PLACE
• $950,000 · 2 bd / 2 ba / 1,947 sq ft · 1411 DEVON ROAD (Orwin Manor Westminster)
• $900,000 · 4 bd / 3 ba / 2,807 sq ft · 2052 WOOD THRUSH LANE
• $230,000 · 3 bd / 2 ba / 1,268 sq ft · 216 LEWFIELD CIR #216
• $3.39M · 5 bd / 6 ba / 4,520 sq ft · 1751 GLENCOE ROAD (Forest Hills)
• $479,999 · 3 bd / 2.5 ba / 1,776 sq ft · 2219 WINTER WOODS BOULEVARD
• $985,000 · 4 bd / 4 ba / 2,916 sq ft · 1611 CHESTNUT AVENUE (Lake Knowles Terrace)
• $482,000 · 3 bd / 2.5 ba / 2,308 sq ft · 1407 BROAD WING LANE
• $2.50M · 5 bd / 4.5 ba / 3,700 sq ft · 1760 OAKHURST AVENUE (Jenkins Second Add)
• $1.40M · 4 bd / 3.5 ba / 2,984 sq ft · 1737 INDIANA AVENUE (Lawndale)
• $489,900 · 3 bd / 1.5 ba / 1,979 sq ft · 351 STARLING ROAD (Flamingo Shores)
• $349,500 · 2 bd / 1 ba / 709 sq ft · 500 N PENNSYLVANIA AVENUE #G
• $325,000 · 3 bd / 2.5 ba / 1,866 sq ft · 7560 ALOMA PINES COURT
• $519,900 · 4 bd / 3 ba / 1,842 sq ft · 731 BONGART ROAD (Winter Park Estates)
• $289,000 · 2 bd / 2 ba / 1,074 sq ft · 700 MELROSE AVENUE #M23 (Winter Park Gardens Condo)
• $185,000 · 2 bd / 1.5 ba / 1,281 sq ft · 4882 TANGERINE AVENUE #4882 (Wrenwood Condominium)
• $3.25M · 5 bd / 6 ba / 4,459 sq ft · 2823 PARKLAND CIRCLE (Lake Forest Park)
• $575,000 · 4 bd / 3 ba / 2,551 sq ft · 2228 KING CHARLES COURT
• $255,000 · 2 bd / 2 ba / 1,026 sq ft · 1500 GAY ROAD #26-C (Chateaux Du Lac)
• $1.70M · 4 bd / 3.5 ba / 2,661 sq ft · 2613 LAFAYETTE AVENUE (Charmont)
• $1.15M · 2 bd / 2 ba / 993 sq ft · 1602 ALABAMA DRIVE #107 (Alabama Condo)
• $639,000 · 3 bd / 2 ba / 1,573 sq ft · 518 GILBERT ROAD (Winter Park Pines)
• $548,000 · 4 bd / 2 ba / 2,352 sq ft · 2067 POINCIANA ROAD
• $469,900 · 4 bd / 3 ba / 2,088 sq ft · 2020 LEANNE COURT
• $169,000 · 2 bd / 2.5 ba / 1,031 sq ft · 3307 AMBER WOOD WAY #106
• $575,000 · 3 bd / 2 ba / 2,253 sq ft · 112 BELL PLACE (Eastgate Sub Winter Park)
• $325,000 · 3 bd / 2 ba / 1,344 sq ft · 310 GRANADA DRIVE (Fairview Heights Rep)
• $650,000 · 4 bd / 2 ba / 1,650 sq ft · 2322 WOODCREST DRIVE (Kenilworth Estates 1St Add)
• $129,000 · 1 bd / 1 ba / 749 sq ft · 3032 ANTIQUE OAKS CIRCLE #145 (Parkview Village)
• $475,000 · 2 bd / 2 ba / 1,438 sq ft · 2824 PRINCE JOHN ROAD
• $3.40M · 5 bd / 5.5 ba / 4,015 sq ft · 160 W ROCKWOOD WAY
• $2.12M · 5 bd / 4.5 ba / 3,713 sq ft · 918 ENCLAVE PLACE (The Enclave Winter Park)
• $159,900 · 1 bd / 1 ba / 645 sq ft · 2500 LEE ROAD #123 (Lakeside Manor Apts Condo)
• $140,000 · 1 bd / 1 ba / 678 sq ft · 302 LEWFIELD CIRCLE #302 (Stratford A Winter Park Condo)
• $3.19M · 5 bd / 5.5 ba / 4,139 sq ft · 2119 HOWARD DRIVE
• $825,000 · 3 bd / 2 ba / 1,639 sq ft · 100 S INTERLACHEN AVENUE #401 (Cloisters Condo)
• $290,000 · 2 bd / 2.5 ba / 1,133 sq ft · 188 SANDLEWOOD #1
• $285,000 · 3 bd / 2 ba / 1,467 sq ft · 2657 EXUMA WAY
• $259,900 · 2 bd / 2 ba / 1,234 sq ft · 4027 Northlight DR 4 (Winterpark)
• $419,900 · 3 bd / 1 ba / 1,304 sq ft · 712 BAFFIE AVENUE (Dubsdread Heights)
• $165,000 · 2 bd / 2 ba / 840 sq ft · 3651 N GOLDENROD ROAD #C109
• $159,000 · 1 bd / 1 ba / 793 sq ft · 200 SAINT ANDREWS BOULEVARD #704 (Four Seasons Condo)
• $2.00M · 4 bd / 3.5 ba / 3,314 sq ft · 2007 EDWIN BOULEVARD (Eastgate Sub Winter Park)
• $1.95M · 5 bd / 4.5 ba / 3,560 sq ft · 513 DUNRAVEN DRIVE (Kenilworth Shores)
• $355,000 · 3 bd / 2.5 ba / 1,872 sq ft · 7498 ALOMA PINES COURT
• $724,900 · 4 bd / 3 ba / 1,692 sq ft · 266 N RANGER BOULEVARD (Winter Park Pines)
• $398,000 · 3 bd / 2 ba / 1,301 sq ft · 7786 FOX KNOLL PLACE
• $347,500 · 2 bd / 1 ba / 830 sq ft · 1306 S PENNSYLVANIA AVENUE #5 (Virginia Heights)
• $795,000 · 3 bd / 3 ba / 2,488 sq ft · 2345 BROOKSHIRE AVENUE (Brookshire Heights)
• $749,900 · 3 bd / 3 ba / 2,145 sq ft · 1003 GOLFSIDE DRIVE
• $140,000 · 2 bd / 1 ba / 881 sq ft · 1695 LEE ROAD #C206 (Waterfall Cove)
• $425,000 · 3 bd / 2.5 ba / 1,755 sq ft · 2349 SHADOWLAND LOOP
• $265,000 · 2 bd / 2 ba / 908 sq ft · 1250 S DENNING DRIVE #119 (Mead Garden)
• $100,000 · 1 bd / 1 ba / 785 sq ft · 173 SCOTTSDALE SQUARE #173 (Winter Park Woods Condo)
• $6.00M · 5 bd / 5.5 ba / 5,096 sq ft · 698 N NEW YORK AVENUE
• $2.00M · 4 bd / 4 ba / 3,776 sq ft · 555 E LAKE SUE AVENUE
• $449,900 · 3 bd / 2 ba / 1,614 sq ft · 1660 ORANGE AVENUE (Orwin Manor Westminster)
• $429,900 · 3 bd / 2 ba / 1,398 sq ft · 2818 AMBERGATE ROAD (Winter Park Estates)
• $2.99M · 5 bd / 4.5 ba / 4,050 sq ft · 532 LANGHOLM DRIVE (Kenilworth Shores)
• $1.95M · 4 bd / 3.5 ba / 3,479 sq ft · 1951 WINTER PARK ROAD (Charmont)
• $1.89M · 4 bd / 3.5 ba / 3,307 sq ft · 2614 PARKLAND DRIVE (Parklando 03 Winter Park)
• $1.43M · 3 bd / 3 ba / 2,756 sq ft · 100 S VIRGINIA AVENUE #201 (Winter Park Residential)
• $529,000 · 4 bd / 2 ba / 1,845 sq ft · 2211 KING RICHARDS COURT
• $459,900 · 3 bd / 2 ba / 1,706 sq ft · 3334 YOUNG STREET (Winter Park Forest)
• $439,900 · 4 bd / 2 ba / 1,627 sq ft · 3209 HEARTWOOD AVENUE (Bel Aire Pines)
• $319,000 · 2 bd / 2 ba / 1,287 sq ft · 192 BALFOUR DRIVE #2
• $299,900 · 3 bd / 2 ba / 1,078 sq ft · 5080 SEMINOLE AVENUE
• $1.60M · 4 bd / 3.5 ba / 2,942 sq ft · 533 COUNTRY CLUB DRIVE (Lake Killarney Shores)
• $1.55M · 6 bd / 5 ba / 5,239 sq ft · 1257 WADING WATERS CIRCLE
• $1.25M · 3 bd / 2 ba / 1,747 sq ft · 120 BROADVIEW AVENUE (Killarney Estates)
• $654,000 · 3 bd / 2 ba / 2,265 sq ft · 5303 PINE LILY CIRCLE (Sanctuary At Aloma)
• $585,000 · 4 bd / 3.5 ba / 2,322 sq ft · 4260 BEAR GULLY ROAD
• $520,000 · 4 bd / 2 ba / 1,774 sq ft · 1905 BONANZA CT
• $150,000 · 2 bd / 2 ba / 1,063 sq ft · 7453 DANIEL WEBSTER DRIVE #A5 (Colonies)
• $3.40M · 4 bd / 5 ba / 3,658 sq ft · 1742 TEMPLE DRIVE (Lake Knowles Terrace Add 02)
• $6.79M · 5 bd / 5.5 ba / 5,479 sq ft · 901 GOLFVIEW TERRACE
• $3.50M · 5 bd / 5.5 ba / 4,478 sq ft · 662 GRANVILLE DRIVE (Park Grove)
• $1.05M · 4 bd / 3.5 ba / 2,135 sq ft · 1517 HARMON AVENUE (Lawndale)
• $875,000 · 4 bd / 2.5 ba / 2,578 sq ft · 2572 FIFESHIRE DRIVE
• $647,900 · 3 bd / 2 ba / 1,450 sq ft · 250 CAROLINA AVENUE #202 (Park West Condo)
• $249,000 · 3 bd / 2.5 ba / 1,720 sq ft · 2463 GRAND TETON CIRCLE #2463
• $5.50M · 5 bd / 6 ba / 5,181 sq ft · 1166 PALMER AVENUE (Palmer Ave Lakeside Prop)
• $637,500 · 4 bd / 2 ba / 1,688 sq ft · 2215 WOODCREST DRIVE (Kenilworth Estates 1St Add)
• $5.20M · 5 bd / 6 ba / 5,122 sq ft · 825 PALMER AVENUE (J Kronenberger Sub)
• $4.59M · 5 bd / 5.5 ba / 5,211 sq ft · 1525 GRANVILLE DRIVE
• $2.19M · 4 bd / 3 ba / 3,463 sq ft · 1803 BARKER DRIVE (South Lakemont Shores)
• $2.12M · 4 bd / 4.5 ba / 2,850 sq ft · 1271 PALMER AVENUE (J Kronenberger Sub)
• $1.30M · 3 bd / 2.5 ba / 2,563 sq ft · 504 W SWOOPE AVENUE (Vilasa Twnhms)
• $875,000 · 4 bd / 3 ba / 1,876 sq ft · 618 BLAIRSHIRE CIRCLE (Brookshire Heights 4Th Add Winter Park)
• $650,000 · 4 bd / 3 ba / 2,067 sq ft · 943 FAIRWAY DRIVE
• $4.09M · 4 bd / 5.5 ba / 3,720 sq ft · 702 VIA BELLA (Palmer Ave Lakeside Prop)
• $999,000 · 4 bd / 3 ba / 2,803 sq ft · 443 BROADVIEW AVENUE (Killarney Estates)
• $900,000 · 3 bd / 2 ba / 1,887 sq ft · 913 MOSS LANE (Maitland Shores First Add)
• $895,000 · 2 bd / 2 ba / 1,763 sq ft · 311 E MORSE BOULEVARD #4-5 (Phillips Circle Rep)
• $365,000 · 3 bd / 2.5 ba / 1,861 sq ft · 7506 CRANES CREEK COURT #30
• $3.95M · 4 bd / 2 ba / 1,652 sq ft · 540 N PENNSYLVANIA AVENUE (Winter Park Villas)
• $234,900 · 2 bd / 2 ba / 1,295 sq ft · 2383 SUN VALLEY CIRCLE #2383
• $2.48M · 3 bd / 3 ba / 2,316 sq ft · 311 E MORSE BOULEVARD #1-5 (Phillips Circle Rep)
• $769,000 · 4 bd / 2.5 ba / 2,141 sq ft · 2410 SHERBROOKE ROAD
• $170,000 · 2 bd / 2.5 ba / 1,031 sq ft · 7476 WOODBURN COURT #38
• $2.73M · 5 bd / 4.5 ba / 3,784 sq ft · 1773 WALNUT AVENUE (Conwill Estates)
• $675,000 · 4 bd / 2 ba / 1,509 sq ft · 2260 COLDSTREAM DRIVE (Brookshire Heights)
• $5.50M · 4 bd / 4.5 ba / 3,880 sq ft · 2661 VIA TUSCANY (Maitland Shores First Add)
• $915,000 · 3 bd / 3.5 ba / 2,093 sq ft · 1927 S LAKEMONT AVENUE (Lake Spier Xing)
• $735,000 · 4 bd / 3.5 ba / 3,020 sq ft · 1287 VERDANT GLADE PLACE
• $470,000 · 4 bd / 2 ba / 1,756 sq ft · 3020 NICHOLSON DRIVE (Wrenwood Unit 3 3Rd Add)
• $2.35M · 3 bd / 3.5 ba / 3,110 sq ft · 200 S INTERLACHEN AVENUE #350
• $245,000 · 2 bd / 2 ba / 908 sq ft · 1250 S DENNING DRIVE #127 (Mead Garden)
• $660,000 · 3 bd / 3 ba / 1,690 sq ft · 1256 MELISSA COURT
• $579,000 · 3 bd / 2 ba / 1,783 sq ft · 508 BRECHIN DRIVE (Kenilworth Shores)
• $279,999 · 3 bd / 2 ba / 1,467 sq ft · 2275 ISLAND RUN
• $759,675 · 5 bd / 3.5 ba / 2,832 sq ft · 724 MONMOUTH WAY
• $1.35M · 4 bd / 4 ba / 2,998 sq ft · 1320 ORCHID AVENUE (Elizabeth Heights Sub)
• $1.29M · 3 bd / 4 ba / 2,191 sq ft · 720 PANSY AVENUE (Villa View Park)
• $1.55M · 4 bd / 4 ba / 2,916 sq ft · 2430 CHANTILLY AVENUE
• $739,777 · 4 bd / 2 ba / 2,267 sq ft · 4039 COOL WATER COURT (Lake Waunatta Woods)
• $699,000 · 3 bd / 2 ba / 1,563 sq ft · 1850 BRYAN AVENUE (Lakeview Terrace)
• $799,000 · 3 bd / 2.5 ba / 1,957 sq ft · 1278 S PENNSYLVANIA AVENUE #13 (Casa Jardin Condo)
• $306,900 · 3 bd / 2.5 ba / 1,545 sq ft · 7530 CRANES CREEK COURT
• $255,000 · 2 bd / 2 ba / 1,008 sq ft · 5108 LAZY OAKS DRIVE #5108 (Lazy Oaks Condo)
• $147,000 · 1 bd / 1 ba / 678 sq ft · 285 LEWFIELD CIRCLE #285
• $925,000 · 4 bd / 3 ba / 2,528 sq ft · 471 HOLT AVENUE (Winter Park Villas)
• $575,000 · 2 bd / 2.5 ba / 1,648 sq ft · 1259 INDIANA AVENUE (Townhomes/Harper Place)
• $950,000 · 3 bd / 2 ba / 1,487 sq ft · 1220 HOWELL BRANCH ROAD
• $799,000 · 3 bd / 2.5 ba / 2,022 sq ft · 1621 CHESTNUT AVENUE (Lake Knowles Terrace)
• $269,000 · 2 bd / 1 ba / 710 sq ft · 151 N ORLANDO AVENUE #242 (Lake Killarney Condo)
• $1.88M · 3 bd / 3.5 ba / 2,703 sq ft · 751 PANSY AVENUE
• $1.57M · 3 bd / 2.5 ba / 2,733 sq ft · 2207 KINDEL AVENUE
• $739,000 · 2 bd / 2 ba / 1,311 sq ft · 250 CAROLINA AVENUE #205
• $385,000 · 3 bd / 2 ba / 1,162 sq ft · 7384 GRAND AVENUE
• $3.27M · 5 bd / 5.5 ba / 4,949 sq ft · 1761 LEGION DRIVE (Green Oaks Rep Winter Park)
• $550,000 · 4 bd / 2 ba / 1,936 sq ft · 7525 LODGE POLE TRAIL
• $3.60M · 4 bd / 5 ba / 4,202 sq ft · 276 DETMAR DRIVE
• $242,500 · 2 bd / 2 ba / 913 sq ft · 1250 S DENNING DR #Unit 233 (Mead Garden)
• $189,900 · 2 bd / 2 ba / 953 sq ft · 222 LEWFIELD CIRCLE (Stratford A Winter Park Condo)
• $419,990 · 5 bd / 3 ba / 1,442 sq ft · 2181 LINDEN ROAD (Ridge High 1St Add)
• $279,000 · 2 bd / 2.5 ba / 960 sq ft · 283 SANDLEWOOD TRAIL #3
• $1.35M · 3 bd / 2.5 ba / 2,080 sq ft · 150 E READING WAY (Charmont)
• $369,999 · 3 bd / 2.5 ba / 1,907 sq ft · 2017 CANNY COVE
• $2.57M · 5 bd / 4.5 ba / 3,670 sq ft · 1754 TAYLOR AVENUE
• $860,000 · 5 bd / 3.5 ba / 3,284 sq ft · 120 LONGBRANCH ROAD
• $659,000 · 3 bd / 3 ba / 1,794 sq ft · 900 CARVER STREET (Magnolia Gardens Sub Winter Park)
• $349,000 · 3 bd / 2.5 ba / 1,872 sq ft · 7605 ALOMA PINES COURT
• $189,900 · 2 bd / 2 ba / 1,037 sq ft · 623 GRENADINE COURT #623 (Winter Park Villas)
• $469,900 · 3 bd / 2 ba / 2,047 sq ft · 1660 GLADIOLAS DRIVE
• $394,500 · 3 bd / 2.5 ba / 1,782 sq ft · 2857 CLEVER LANE
• $775,000 · 4 bd / 3 ba / 2,164 sq ft · 722 S RANGER BOULEVARD
• $525,000 · 4 bd / 2 ba / 2,126 sq ft · 2641 CARVELL COURT (Winter Park Estates)
• $2.70M · 5 bd / 4.5 ba / 3,588 sq ft · 648 WORTHINGTON DRIVE (Kenilworth Shores)
• $429,000 · 3 bd / 2 ba / 1,498 sq ft · 1652 BERKSHIRE AVENUE
• $3.89M · 6 bd / 5 ba / 4,677 sq ft · 620 VIRGINIA DRIVE (Timberlane Shores)
• $3.40M · 4 bd / 3 ba / 3,377 sq ft · 2622 LAKE HOWELL LANE
• $1.68M · 4 bd / 3.5 ba / 3,307 sq ft · 2343 VERSAILLES AVENUE (Fontainebleau)
• $1.43M · 4 bd / 3.5 ba / 2,984 sq ft · 1546 MILLER AVENUE (Lawndale)
• $799,999 · 2 bd / 2 ba / 1,540 sq ft · 1431 PALM AVENUE (Lake Knowles Terrace Add 02)
• $530,000 · 4 bd / 3 ba / 1,745 sq ft · 2627 AMBERGATE ROAD (Winter Park Estates)
• $394,900 · 3 bd / 2 ba / 1,494 sq ft · 1955 ELAND AVENUE (Lake Bell Terrace)
• $247,000 · 2 bd / 2 ba / 1,316 sq ft · 2477 TAHOE CIRCLE #2477
• $1.70M · 4 bd / 3.5 ba / 2,530 sq ft · 2308 MULBRY DRIVE (Lake Forest Park)
• $1.62M · 5 bd / 4.5 ba / 3,133 sq ft · 2407 LAFAYETTE AVENUE (Fontainebleau)
• $4.35M · 5 bd / 5.5 ba / 4,827 sq ft · 857 BROCK STREET (Park Grove)
• $575,000 · 2 bd / 2.5 ba / 1,851 sq ft · 1071 ARAGON AVENUE (Seville Park)
• $650,000 · 4 bd / 2.5 ba / 1,770 sq ft · 1122 WILDMEADOW RUN
• $180,000 · 1 bd / 1 ba / 638 sq ft · 1695 LEE ROAD #D107
• $599,000 · 3 bd / 2 ba / 2,031 sq ft · 4026 TENITA DRIVE
• $495,000 · 3 bd / 2 ba / 1,380 sq ft · 5316 HALYARD COURT
• $214,900 · 3 bd / 2.5 ba / 1,151 sq ft · 7413 BELLE RIVER COURT #3
• $3.65M · 3 bd / 4 ba / 3,878 sq ft · 125 S INTERLACHEN AVENUE #1
• $1.69M · 4 bd / 3.5 ba / 3,174 sq ft · 1420 MAGNOLIA AVENUE
• $3.00M · 3 bd / 4 ba / 3,244 sq ft · 125 S INTERLACHEN AVENUE #2
• $2.39M · 5 bd / 6.5 ba / 4,506 sq ft · 2412 CHANTILLY AVENUE
• $510,000 · 3 bd / 2.5 ba / 1,669 sq ft · 1061 ARAGON AVENUE #1061
• $368,000 · 4 bd / 2 ba / 1,240 sq ft · 885 CARNATION DRIVE
• $97,000 · 1 bd / 1 ba / 796 sq ft · 1000 S SEMORAN BOULEVARD #302 (Golfside Villas Condo)
• $430,000 · 3 bd / 2 ba / 1,645 sq ft · 3740 HAWTHORNE LANE
• $268,000 · 2 bd / 2 ba / 1,295 sq ft · 2475 TAHOE CIRCLE
• $1.45M · 5 bd / 4.5 ba / 3,109 sq ft · 777 HALIFAX AVENUE (Park Manor First Add)
• $334,000 · 3 bd / 2 ba / 1,149 sq ft · 3562 BOUGAINVILLEA DRIVE
• $425,000 · 3 bd / 2 ba / 1,238 sq ft · 1886 CLEMATIS LANE
• $400,000 · 3 bd / 2 ba / 1,483 sq ft · 5409 ALBERT DRIVE
• $115,000 · 1 bd / 1 ba / 735 sq ft · 1000 S SEMORAN BOULEVARD #305 (Golfside Villas Condo)
• $449,000 · 3 bd / 2 ba / 1,737 sq ft · 2703 TIERRA CIRCLE
• $1.80M · 5 bd / 4.5 ba / 4,029 sq ft · 281 BREWER AVENUE
• $389,000 · 3 bd / 2.5 ba / 1,907 sq ft · 2033 CANNY COVE
• $549,900 · 3 bd / 2 ba / 1,837 sq ft · 1003 LAKE BELL DRIVE (Albert Lee Ridge Add 02 Winter Park)
• $1.18M · 3 bd / 2.5 ba / 1,329 sq ft · 240 KILLARNEY DRIVE (Killarney Estates)
• $1.15M · 4 bd / 1 ba / 1,260 sq ft · 230 KILLARNEY DRIVE (Killarney Estates)
• $775,000 · 4 bd / 2.5 ba / 1,899 sq ft · 1562 ARBOR PARK DRIVE (Conwill Estates)
• $335,000 · 3 bd / 2.5 ba / 1,790 sq ft · 2526 PASSAMONTE DRIVE #10F
• $2.00M · 3 bd / 2 ba / 1,765 sq ft · 1133 BELLA LAGO COVE
• $170,000 · 2 bd / 2.5 ba / 1,031 sq ft · 7450 WYNNEWOOD SQUARE #189
• $1.79M · 4 bd / 4 ba / 3,440 sq ft · 922 N PENNSYLVANIA AVENUE
• $1.60M · 4 bd / 3.5 ba / 2,568 sq ft · 250 KILLARNEY (Killarney Estates)
• $699,500 · 4 bd / 2.5 ba / 2,197 sq ft · 1418 LONE FEATHER TRAIL
• $1.45M · 3 bd / 2.5 ba / 1,944 sq ft · 462 W LYMAN AVENUE (Winter Park Villas)
• $250,000 · 3 bd / 2 ba / 1,311 sq ft · 2450 GRAND TETON CIRCLE #2450
• $1.43M · 4 bd / 4 ba / 2,642 sq ft · 1581 MAGNOLIA AVE (Lake Knowles Terrace Add 02)
• $2.80M · 5 bd / 4.5 ba / 4,018 sq ft · 609 S PHELPS AVENUE
• $424,900 · 4 bd / 2.5 ba / 1,980 sq ft · 1564 LAWNDALE CIRCLE
• $268,000 · 2 bd / 2 ba / 1,008 sq ft · 5184 LAZY OAKS DRIVE (Lazy Oaks Condo)
• $279,900 · 2 bd / 2 ba / 1,295 sq ft · 2305 SUN VALLEY CIR
• $138,000 · 1 bd / 1 ba / 776 sq ft · 1000 S SEMORAN BOULEVARD #408 (Golfside Villas Condo)
• $138,000 · 1 bd / 1 ba / 796 sq ft · 1000 S SEMORAN BOULEVARD #306 (Golfside Villas Condo)
• $138,000 · 1 bd / 1 ba / 776 sq ft · 1000 S SEMORAN BOULEVARD #404 (Golfside Villas Condo)
• $5.60M · 5 bd / 5.5 ba / 5,152 sq ft · 2228 AZALEA PLACE (Maitland Shores First Add)
• $899,000 · 4 bd / 3 ba / 2,075 sq ft · 3006 NORTHWOOD BOULEVARD (Northwood Terrace)
• $474,999 · 2 bd / 1 ba / 857 sq ft · 981 ARAGON AVENUE (Seville Park)
• $2.69M · 3 bd / 3.5 ba / 3,286 sq ft · 660 W MORSE BOULEVARD
• $364,900 · 3 bd / 2 ba / 1,666 sq ft · 1840 ASTER DRIVE
• $210,000 · 2 bd / 2.5 ba / 1,578 sq ft · 7488 WHISPERWOOD DRIVE #28 (Whisperwood Condo)
• $1.60M · 4 bd / 4 ba / 3,065 sq ft · 723 SYMONDS AVENUE
• $1.25M · 4 bd / 4 ba / 2,928 sq ft · 2015 SUMMERFIELD ROAD (Kenilworth Shores)
• $2.00M · 5 bd / 4.5 ba / 2,889 sq ft · 240 N PHELPS AVENUE (Sylvan Heights)
• $1.38M · 3 bd / 2.5 ba / 2,585 sq ft · 512 W SWOOPE AVENUE (Vilasa Twnhms)
• $235,000 · 2 bd / 2 ba / 1,026 sq ft · 1500 GAY ROAD #3C (Chateaux Du Lac)
• $199,900 · 1 bd / 1 ba / 582 sq ft · 151 NORTH ORLANDO AVENUE #142 (Lake Killarney Condominium Assn Inc.)
• $1.77M · 3 bd / 3.5 ba / 3,112 sq ft · 101 S NEW YORK AVENUE #311 (Winter Park Residential)
• $374,000 · 3 bd / 2 ba / 1,285 sq ft · 1605 PURITAN AVENUE (Eastbrook Sub Unit 06 2Nd Rep)
• $849,000 · 3 bd / 2.5 ba / 1,904 sq ft · 437 N CAPEN AVENUE (Canton Ave Cottages 1)
• $449,500 · 4 bd / 2 ba / 2,250 sq ft · 2008 HOUNDSLAKE DRIVE
• $725,000 · 4 bd / 2.5 ba / 2,196 sq ft · 1316 BLUE STEM LANE
• $455,000 · 4 bd / 2.5 ba / 1,903 sq ft · 8433 COMMANDER COVE
• $415,000 · 3 bd / 2 ba / 1,676 sq ft · 1535 LAWNDALE CIRCLE
• $4.50M · 4 bd / 6 ba / 5,550 sq ft · 231 CHELTON CIRCLE (Forest Hills)
• $1.37M · 5 bd / 4 ba / 2,446 sq ft · 1473 BERKSHIRE AVENUE (Orwin Manor Westminster)
• $199,900 · 2 bd / 1 ba / 851 sq ft · 2500 LEE ROAD #220 (Lakeside Manor Apts Condo)
• $1.43M · 3 bd / 4 ba / 2,756 sq ft · 641 NORTHWOOD CIRCLE (Winter Park Oasis)
• $490,900 · 3 bd / 3 ba / 1,786 sq ft · 525 OLOLU DRIVE
• $2.62M · 3 bd / 3.5 ba / 3,048 sq ft · 413 W MORSE BOULEVARD
• $3.50M · 4 bd / 3.5 ba / 4,036 sq ft · 2240 VENETIAN WAY (Maitland Shores 1St Add)
• $535,000 · 3 bd / 3.5 ba / 1,937 sq ft · 1250 FORMOSA AVENUE (Urban Green 12)
• $399,900 · 3 bd / 2 ba / 1,366 sq ft · 5503 ALBERT DRIVE
• $998,000 · 4 bd / 4 ba / 2,469 sq ft · 1404 BORDER DRIVE (Winter Park Village)
• $695,000 · 4 bd / 3 ba / 2,312 sq ft · 715 S RANGER BOULEVARD (Winter Park Pines)
• $836,000 · 3 bd / 3 ba / 2,017 sq ft · 338 BLUE HERON DRIVE (Flamingo Shores)
• $6.00M · 5 bd / 7 ba / 7,397 sq ft · 1571 WOODLAND AVENUE (Comstock Park)
• $449,000 · 4 bd / 2 ba / 1,624 sq ft · 1320 GLADIOLAS DR
• $99,900 · 2 bd / 1 ba / 881 sq ft · 1695 LEE ROAD #D211
• $999,900 · 5 bd / 4.5 ba / 3,652 sq ft · 1448 LAKE FLORENCE WAY
• $650,000 · 3 bd / 2 ba / 1,350 sq ft · 300 CAROLINA AVENUE #402C (Park West Condo)
• $246,400 · 2 bd / 2.5 ba / 1,300 sq ft · 193 LEWFIELD CIRCLE (Stratford A Winter Park Condo)
• $175,000 · 2 bd / 2.5 ba / 1,031 sq ft · 7327 FOREST HILL COURT #223
• $1.49M · 4 bd / 3.5 ba / 3,048 sq ft · 1570 PALMER AVENUE (Comstock Park)
• $375,000 · 3 bd / 2.5 ba / 1,872 sq ft · 7522 ALOMA PINES COURT
• $999,000 · 4 bd / 4.5 ba / 2,638 sq ft · 616 BRECHIN DRIVE (Kenilworth Shores)
• $524,900 · 3 bd / 2 ba / 1,434 sq ft · 1741 WESTCHESTER AVENUE
• $2.30M · 5 bd / 4.5 ba / 3,865 sq ft · 938 ENCLAVE PLACE (The Enclave Winter Park)
• $399,000 · 3 bd / 2.5 ba / 1,907 sq ft · 1995 CANNY COVE
• $325,000 · 3 bd / 2 ba / 1,518 sq ft · 7393 GRAND AVENUE
• $2.27M · 5 bd / 4.5 ba / 3,813 sq ft · 930 ENCLAVE PLACE (The Enclave Winter Park)
• $439,000 · 3 bd / 2 ba / 1,606 sq ft · 950 HANOVER AVENUE
• $2.50M · 5 bd / 5 ba / 4,572 sq ft · 450 LAKEWOOD DRIVE
• $1.48M · 4 bd / 2 ba / 2,640 sq ft · 446 MELROSE AVENUE (Virginia Heights)
• $395,000 · 2 bd / 1 ba / 749 sq ft · 811 OVERSPIN DRIVE (Dubsdread Heights)
• $2.50M · 4 bd / 3.5 ba / 3,553 sq ft · 541 W CANTON AVENUE
• $1.30M · 4 bd / 3.5 ba / 2,459 sq ft · 102 BELL PLACE
• $189,000 · 2 bd / 2 ba / 1,018 sq ft · 2918 ANTIQUE OAKS CIRCLE #25
• $630,000 · 6 bd / 3 ba / 3,145 sq ft · 2600 EUSTON ROAD (Glencoe Sub Winter Park)
• $3.60M · 4 bd / 5.5 ba / 4,066 sq ft · 1441 CARDINAL COURT (Winflor Court Pt Rep)
• $229,000 · 3 bd / 2.5 ba / 1,151 sq ft · 7454 WYNNEWOOD SQUARE #188
• $140,000 · 2 bd / 2.5 ba / 1,090 sq ft · 3021 AARON BURR AVENUE #3 (Colonies)
• $825,000 · 4 bd / 3.5 ba / 2,589 sq ft · 1131 WILDMEADOW RUN
• $2.07M · 5 bd / 4.5 ba / 3,617 sq ft · 914 ENCLAVE PLACE (The Enclave Winter Park)
• $1.55M · 4 bd / 3.5 ba / 2,756 sq ft · 905 ENCLAVE PLACE (The Enclave Winter Park)
• $1.55M · 4 bd / 3.5 ba / 2,738 sq ft · 901 ENCLAVE PLACE (The Enclave Winter Park)
• $419,000 · 4 bd / 2 ba / 1,376 sq ft · 501 HERITAGE BOULEVARD
• $6.90M · 6 bd / 6 ba / 6,396 sq ft · 1260 ALABAMA DRIVE (J Kronenberger Sub)
• $1.59M · 3 bd / 2 ba / 2,012 sq ft · 1113 VIA DEL MAR (Tuscany Terrace)
• $799,000 · 5 bd / 3 ba / 2,242 sq ft · 1927 ELAND AVENUE (Lake Bell Terrace)
• $499,900 · 3 bd / 2 ba / 1,570 sq ft · 330 ELKHORN COURT (Winter Park Pines Merrie Oaks)
• $499,000 · 3 bd / 2 ba / 1,088 sq ft · 2231 NAIRN DRIVE (Aloma)
• $499,000 · 2 bd / 1 ba / 920 sq ft · 230 STRATHY LANE (Aloma)
• $182,900 · 2 bd / 2 ba / 927 sq ft · 205 LEWFIELD CIRCLE #205 (Stratford A Winter Park Condo)
• $1.38M · 4 bd / 3.5 ba / 2,170 sq ft · 1751 GOODRICH AVENUE (Sylvan Heights)
• $680,000 · 4 bd / 3.5 ba / 2,664 sq ft · 432 W SWOOPE AVENUE (Swoope Park)
• $2.19M · 5 bd / 3.5 ba / 3,691 sq ft · 1885 TEMPLE DRIVE
• $479,999 · 4 bd / 2 ba / 2,092 sq ft · 2217 SUSSEX ROAD
• $1.75M · 4 bd / 2.5 ba / 2,350 sq ft · 1840 ANZLE AVENUE (Sylvan Heights)
• $299,999 · 2 bd / 1 ba / 710 sq ft · 151 N ORLANDO AVENUE #118 (Lake Killarney Condo)
• $184,400 · 1 bd / 1 ba / 645 sq ft · 2500 LEE RD. #222 (Lakeside Manor Apts Condo)
• $849,000 · 2 bd / 2 ba / 1,086 sq ft · 560 OLOLU DRIVE (Killarney Circle)
• $285,000 · 2 bd / 1 ba / 710 sq ft · 151 N ORLANDO AVENUE ##115 (Lake Killarney Condo)
• $299,000 · 1 bd / 1 ba / 482 sq ft · 311 E MORSE BOULEVARD #7-5 (Phillips Circle Rep)
• $109,000 · 1 bd / 1 ba / 785 sq ft · 311 SCOTTSDALE SQUARE #311 (Winter Park Woods Condo)
• $179,990 · 2 bd / 2.5 ba / 1,031 sq ft · 3370 CEDAR SPRINGS PLACE #156
• $285,000 · 2 bd / 2 ba / 1,669 sq ft · 2336 SUN VALLEY CIRCLE #BLDG 20
• $2.95M · 5 bd / 5.5 ba / 3,863 sq ft · 1821 ENGLEWOOD ROAD (Forest Hills)
• $619,500 · 3 bd / 2.5 ba / 1,539 sq ft · 2758 BANCHORY ROAD (Winter Park Pines)
• $279,000 · 1 bd / 1 ba / 570 sq ft · 311 E MORSE BOULEVARD #7-11 (Phillips Circle Rep)
• $89,900 · 1 ba / 549 sq ft · 3071 GEORGE MASON AVENUE #5 (Colonies)
• $205,000 · 3 bd / 2 ba / 1,149 sq ft · 1695 LEE ROAD #C202 (Waterfall Cove At Winter Park)
• $5.48M · 6 bd / 6.5 ba / 6,134 sq ft · 470 W COMSTOCK AVENUE
• $2.45M · 4 bd / 4.5 ba / 3,308 sq ft · 2718 EASTERN PARKWAY (Parklando Winter Park)
• $2.10M · 5 bd / 5.5 ba / 4,155 sq ft · 1355 HIBISCUS AVENUE (Lake Knowles Terrace Add 02)
• $1.65M · 3 bd / 3 ba / 2,254 sq ft · 1124 N PENNSYLVANIA AVENUE
• $1.15M · 4 bd / 2.5 ba / 2,582 sq ft · 1824 JESSICA COURT (Waterbridge)
• $389,000 · 3 bd / 2 ba / 1,416 sq ft · 3471 ATHENA DRIVE
• $339,000 · 2 bd / 2 ba / 1,140 sq ft · 220 KILLARNEY BAY COURT #6-2 (Killarney Bay Condo)
• $265,000 · 2 bd / 2 ba / 1,178 sq ft · 7797 FERNBROOK WAY

Pending and under contract in Winter Park (18)

Winter Park homes that have an accepted offer and are working toward closing. They can still fall through, so each one keeps its page until it closes.

• $305,000 · 3 bd / 2 ba / 1,467 sq ft · 2370 BARBADOS DRIVE
• $575,000 · 3 bd / 2.5 ba / 2,031 sq ft · 1931 ASTER DRIVE
• $225,000 · 3 bd / 1 ba / 1,227 sq ft · 3462 SEAGRAPE DRIVE
• $1.79M · 4 bd / 4 ba / 2,819 sq ft · 2501 LAFAYETTE AVENUE
• $410,000 · 3 bd / 2 ba / 1,318 sq ft · 1021 PRINCESS GATE BOULEVARD
• $299,900 · 3 bd / 1 ba / 1,520 sq ft · 1915 CARRIGAN AVENUE
• $135,000 · 2 bd / 2 ba / 1,018 sq ft · 3020 ANTIQUE OAKS CIRCLE #129
• $365,000 · 3 bd / 1.5 ba / 1,185 sq ft · 2136 LINDEN ROAD
• $255,000 · 3 bd / 2 ba / 1,509 sq ft · 7348 GRAND AVENUE
• $562,000 · 4 bd / 3 ba / 1,778 sq ft · 5233 LAKE HOWELL ROAD
• $380,000 · 3 bd / 1 ba / 1,143 sq ft · 2626 AMBERGATE ROAD
• $770,000 · 4 bd / 3 ba / 2,192 sq ft · 2286 MARSH SEDGE LANE
• $1.09M · 3 bd / 2.5 ba / 1,873 sq ft · 1922 HAMMERLIN AVENUE
• $985,000 · 4 bd / 3 ba / 2,868 sq ft · 2667 COCHISE TRAIL
• $1.73M · 4 bd / 3.5 ba / 3,727 sq ft · 1840 BRYAN AVENUE
• $540,000 · 3 bd / 2.5 ba / 1,660 sq ft · 1261 INDIANA AVENUE
• $2.46M · 4 bd / 3.5 ba / 3,294 sq ft · 2228 HOWARD DRIVE
• $275,000 · 2 bd / 2 ba / 1,008 sq ft · 5143 LAZY OAKS DRIVE #5143

Browse every listing on Momentum Realty.

Homes for sale in Winter Park by ZIP code

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

Winter Park communities with the most homes for sale

The Winter Park 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 Park: property types

• Single-family houses: 260
• Condos: 95
• Townhouses: 39

Another 2 listings in Winter Park are land, commercial or other non-residential property and are not counted above.

Browse by type: Condos for sale in Winter Park (95) · Townhomes for sale in Winter Park (39).

The Winter Park real estate market right now

Over the last 12 months 887 homes sold in Winter Park at a median of $499,000 (-0.2% year over year), $270 per square foot. Sellers received 98% of list price and homes took a median 37 days to go under contract. With 394 homes for sale against that sales pace, months of supply is 5.3, a balanced market by the six-month rule. Cash buyers accounted for 32% of sales. New construction was 6% of sales.

Winter Park supply by price band

Winter Park 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 Park costs to own

Take the median $636,250 listing with 20% down at today’s 7.11% 30-year rate: principal and interest run about $3,424/month. Orange County’s typical millage of 16.67 puts property tax near $9,775/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 $4,356/month plus any HOA or CDD assessment.

Explore Winter Park

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

Homes for sale near Winter Park

• Homes for sale in Orlando, FL — 4383 listings
• Homes for sale in Winter Garden, FL — 737 listings
• Homes for sale in Apopka, FL — 540 listings
• Homes for sale in Windermere, FL — 258 listings
• Homes for sale in Ocoee, FL — 161 listings
• Homes for sale in Maitland, FL — 122 listings
• Homes for sale in Zellwood, FL — 58 listings
• Homes for sale in Oakland, FL — 37 listings
• Homes for sale in Belle Isle, FL — 31 listings
• Homes for sale in Gotha, FL — 19 listings
• Homes for sale in Christmas, FL — 7 listings
• Homes for sale in Golden Oak, FL — 5 listings

Recently off market in Winter Park

Homes in Winter Park 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.

• 645 Pansy Avenue · last listed $2,390,000 · off market Nov 13, 2026
• 630 Killarney Bay Court #3 · last listed $449,900 · off market Nov 13, 2026
• 5334 Lanyard Court · last listed $479,900 · off market Nov 13, 2026
• 333 Cornwall Road · last listed $549,900 · off market Nov 13, 2026
• 2825 Mulford Avenue · last listed $629,000 · off market Nov 13, 2026
• 2301 Conifer Avenue · last listed $405,000 · off market Nov 13, 2026
• 1842 Puritan Avenue · last listed $419,000 · off market Nov 13, 2026
• 1552 Little Wren Lane · last listed $440,000 · off market Nov 13, 2026
• 1500 Gay Road #4D · last listed $159,900 · off market Nov 13, 2026
• 1416 Border Drive · last listed $620,000 · off market Nov 13, 2026
• 1265 Arlington Pl · last listed $774,900 · off market Nov 13, 2026
• 1225 Sharon Place · last listed $1,749,000 · off market Nov 13, 2026

Common questions

Listings, counts and prices are from Momentum Realty’s MLS record of active residential listings in Winter Park as of 2026-11-13 and refresh as homes list and sell. Listing information provided by the Florida Gulf Coast Multiple Listing Service, Inc. Information is deemed reliable but not guaranteed by the MLS to be accurate. 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.