Winter Park

Community Info

  • Price Range:
    $299,000-$7,250,000

ABOUT WINTER PARK LUXURY HOMES & REAL ESTATE

Winter Park, a town rich in culture and history. Home to 70 different parks as well as the Cornell Fine Art Museum which houses one of Florida's oldest colleges. With its gorgeous homes plus scenic views from around this old-world charm area you'll never want for more than just living here. The perfect place to take it easy and unwind, Winter Park is known for its serene beauty.

Reasons to Live in Winter Park Florida

  • Living in Winter Park offers residents an urban suburban mix feel and most residents own their homes. In Winter Park there are a lot of bars, restaurants, coffee shops, and parks. Many young professionals and retirees live in Winter Park and residents tend to have moderate political views.
  • Winter Park, FL is nestled between Orlando & Sanford offering magnificent mansions combined with vibrant street scenes full fabulous restaurants and boutique stores. Visitors here can enjoy swan boats cruising across Lake Virginia or find tranquility at Leu Gardens which offers breathtaking views no matter which season you visit during! Diverse resort city - East-central Florida, about 25 miles from the Atlantic Coast.
  • The unemployment rate in Winter Park is 4.3% (U.S. avg. is 6.0%). Recent job growth is Positive. Winter Park jobs have increased by 3.9%
  • November, April and March are the most pleasant months in Winter Park, while August and July are the least comfortable months.
  • Winter Park public schools spend $9,506 per student. The average school expenditure in the U.S. is $12,383. There are about 15.9 students per teacher in Winter Park
  • The median home cost in Winter Park is Real Estate: $494,000 Home appreciation the last 10 years has been 20.3%.

What is Winter Park Florida known for?

  • Though it is composed mainly of homes Winter Park offers many options for leisure activities as it is home to an abundance of restaurants and even a bowling alley. Park Avenue is a street with many shops and restaurants while also being a park and place of community gathering.

Is Winter Park Florida safe?

  • The crime rate in the city is well below the national average, and residents report feeling very safe in their homes and neighborhoods. In addition, the city has its own police force, which provides quick response times and 24-hour patrols. For these reasons, Winter Park is often cited as one of the safest cities in Florida.

Why live in Winter Park Florida?

The City of Winter Park has a lot to offer, from waterfront real estate to higher education and a large art scene. With its abundance of outdoor spaces, museums, and boutiques, you can live in the heart of Florida without sacrificing your creature comforts.

Winter Park Luxury Homes for Sale by Orlando Best Real Estate Call Orlando Best Real Estate @ 407.961.8412 for Winter Park Luxury Homes for Sale. We Have all the MLS Listings for Winter Park Luxury Homes & the Orlando Area

Winter Park Luxury Homes for Sale by Orlando Best Real Estate

Call Orlando Best Real Estate @ 407.961.8412 for Winter Park Luxury Homes for Sale. We Have all the MLS Listings for Winter Park Luxury Homes & the entire Orlando Area.

Orlando Luxury Homes and Communities

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1260 ALABAMA DRIVE
 $6,900,000 6 / 5
 6,396sf Y / Y
620 VIRGINIA DRIVE
 $3,890,000 6 / 5
 4,677sf N / Y
2914 REEF KNOT PLACE
 $1,725,000 6 / 4
 4,173sf Y / Y
2600 EUSTON ROAD
 $630,000 6 / 3
 3,145sf N / N

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
40 PALMER AVENUE
 $7,250,000 5 / 5
 5,905sf N / Y
1571 WOODLAND AVENUE
 $6,000,000 5 / 6
 7,397sf N / Y
2228 AZALEA PLACE
 $5,600,000 5 / 5
 5,152sf N / Y
1180 VIA LUGANO
 $4,900,000 5 / 5
 4,961sf N / Y
1525 GRANVILLE DRIVE
 $4,750,000 5 / 5
 5,211sf N / Y
857 BROCK STREET
 $4,650,000 5 / 5
 4,827sf N / Y
1417 WILLIAMS DRIVE
 $3,999,000 5 / 5
 4,891sf N / Y
207 E KINGS WAY
 $3,650,000 5 / 4
 3,719sf N / Y
1901 LOCH BERRY ROAD
 $3,500,000 5 / 5
 4,831sf N / Y
1627 MIZELL AVENUE
 $3,300,000 5 / 5
 3,421sf N / Y
1836 WHITEHALL DRIVE
 $3,245,000 5 / 6
 4,168sf N / Y
1821 ENGLEWOOD ROAD
 $3,235,000 5 / 5
 3,863sf N / Y
648 WORTHINGTON DRIVE
 $2,700,000 5 / 4
 3,588sf N / Y
1754 TAYLOR AVENUE
 $2,569,999 5 / 4
 3,670sf N / Y
1823 SUNSET DRIVE
 $2,549,000 5 / 4
 3,479sf N / Y
450 LAKEWOOD DRIVE
 $2,500,000 5 / 4
 4,572sf N / Y
2838 WRIGHT AVENUE
 $2,399,000 5 / 4
 3,479sf N / Y
1840 LAUREL ROAD
 $2,299,000 5 / 5
 2,868sf N / Y
926 ENCLAVE PLACE
 $2,235,000 5 / 4
 4,150sf N / Y
1885 TEMPLE DRIVE
 $2,195,000 5 / 3
 3,691sf N / Y
942 ENCLAVE PLACE
 $2,195,000 5 / 5
 3,831sf N / Y
946 ENCLAVE PLACE
 $2,175,000 5 / 4
 3,989sf N / Y
240 N PHELPS AVENUE
 $2,150,000 5 / 4
 2,889sf N / Y
950 ENCLAVE PLACE
 $2,125,000 5 / 4
 3,797sf N / Y
938 ENCLAVE PLACE
 $2,099,000 5 / 4
 3,865sf N / Y
930 ENCLAVE PLACE
 $2,050,000 5 / 4
 3,813sf N / Y
910 ENCLAVE PLACE
 $1,899,000 5 / 4
 3,620sf N / Y
914 ENCLAVE PLACE
 $1,895,000 5 / 4
 3,617sf N / Y
2032 KIMBRACE PLACE
 $1,800,000 5 / 4
 3,382sf N / Y
281 BREWER AVENUE
 $1,800,000 5 / 4
 4,029sf N / Y
2501 WINTER PARK ROAD
 $1,649,000 5 / 3
 3,304sf N / N
2407 LAFAYETTE AVENUE
 $1,625,000 5 / 4
 3,133sf N / Y
1864 GRINNELL TERRACE
 $1,599,000 5 / 3
 3,028sf N / Y
1526 MILLER AVENUE
 $1,574,900 5 / 4
 3,252sf N / Y
777 HALIFAX AVENUE
 $1,500,000 5 / 4
 3,109sf N / N
1473 BERKSHIRE AVENUE
 $1,429,000 5 / 4
 2,351sf N / Y
1523 MILLER AVENUE
 $1,400,000 5 / 4
 3,164sf N / Y
1448 LAKE FLORENCE WAY
 $1,099,900 5 / 4
 3,652sf N / Y
2702 PARKLAND DRIVE
 $1,049,000 5 / 3
 2,656sf N / N
120 LONGBRANCH ROAD
 $860,000 5 / 3
 3,284sf N / Y
1927 ELAND AVENUE
 $820,000 5 / 3
 2,242sf N / N
2612 ROXBURY ROAD
 $630,000 5 / 3
 2,472sf N / N

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
313 SYLVAN DRIVE
 $5,500,000 4 / 4
 4,775sf Y / Y
231 CHELTON CIRCLE
 $4,950,000 4 / 5
 5,550sf N / Y
1441 CARDINAL COURT
 $4,285,000 4 / 5
 4,066sf N / Y
1150 VIA SALERNO
 $3,975,000 4 / 5
 3,850sf N / Y
2240 VENETIAN WAY
 $3,500,000 4 / 3
 4,036sf Y / Y
1581 FOREST AVENUE
 $3,275,000 4 / 4
 4,683sf N / Y
361 E KINGS WAY
 $3,199,000 4 / 4
 3,737sf N / Y
948 POINCIANA LANE
 $2,750,000 4 / 4
 3,676sf N / Y
541 W CANTON AVENUE
 $2,650,000 4 / 3
 3,553sf N / Y
2228 HOWARD DRIVE
 $2,460,000 4 / 3
 3,294sf N / Y
645 PANSY AVENUE
 $2,390,000 4 / 4
 3,661sf N / Y
1271 PALMER AVENUE
 $2,275,000 4 / 4
 2,835sf N / Y
525 S LAKEMONT AVENUE
 $1,999,990 4 / 3
 3,330sf N / Y
1398 GROVE TERRACE
 $1,995,000 4 / 3
 3,450sf N / Y
922 N PENNSYLVANIA AVENUE
 $1,995,000 4 / 4
 3,440sf N / N
2343 VERSAILLES AVENUE
 $1,865,000 4 / 3
 3,307sf N / Y
723 SYMONDS AVENUE
 $1,800,000 4 / 4
 3,065sf N / N
1750 CAROLLEE LANE
 $1,780,000 4 / 3
 3,249sf N / Y
1840 ANZLE AVENUE
 $1,750,000 4 / 2
 2,350sf N / Y
2525 LAFAYETTE AVENUE
 $1,749,000 4 / 3
 2,715sf N / Y
1840 BRYAN AVENUE
 $1,725,000 4 / 3
 3,727sf N / Y
2308 MULBRY DRIVE
 $1,699,000 4 / 3
 2,530sf N / Y
1420 MAGNOLIA AVENUE
 $1,690,000 4 / 3
 3,174sf N / Y
1903 N PARK AVENUE
 $1,675,000 4 / 4
 2,807sf N / Y
446 MELROSE AVENUE
 $1,625,000 4 / 2
 2,640sf N / N
250 KILLARNEY
 $1,600,000 4 / 3
 2,568sf N / Y
2430 CHANTILLY AVENUE
 $1,599,000 4 / 4
 2,916sf N / Y
708 BALMORAL ROAD
 $1,590,000 4 / 3
 2,786sf N / Y
341 E READING WAY
 $1,565,000 4 / 4
 3,723sf N / Y
1421 CHAPMAN CIRCLE
 $1,450,000 4 / 3
 3,578sf N / N
1581 MAGNOLIA AVE
 $1,425,000 4 / 4
 2,756sf N / N
1546 MILLER AVENUE
 $1,419,900 4 / 3
 2,984sf N / Y
1751 GOODRICH AVENUE
 $1,380,000 4 / 3
 2,170sf N / N
102 BELL PLACE
 $1,349,000 4 / 3
 2,459sf N / Y
2015 SUMMERFIELD ROAD
 $1,262,500 4 / 4
 3,024sf N / Y
1870 STAUNTON AVENUE
 $1,250,000 4 / 3
 2,525sf N / N
230 KILLARNEY DRIVE
 $1,250,000 4 / 1
 1,260sf Y / N
AVENUE
 $1,249,900 4 / 3
 2,936sf N / N
1404 BORDER DRIVE
 $1,100,000 4 / 4
 2,469sf N / N
2667 COCHISE TRAIL
 $1,000,050 4 / 3
 2,868sf N / Y
616 BRECHIN DRIVE
 $999,000 4 / 4
 2,638sf N / Y
3006 NORTHWOOD BOULEVARD
 $999,000 4 / 3
 2,075sf N / N
1611 CHESTNUT AVENUE
 $995,000 4 / 4
 2,916sf N / N
1800 MAGNOLIA AVENUE
 $950,000 4 / 2
 2,431sf N / Y
Lot #21 KAROLINA AVE
 $918,000 4 / 2
 2,662sf N / N
1521 HERON WOOD PLACE
 $860,000 4 / 2
 3,950sf N / Y
1090 WILDMEADOW RUN
 $835,000 4 / 3
 2,589sf N / N
1131 WILDMEADOW RUN
 $825,000 4 / 3
 2,589sf Y / N
722 S RANGER BOULEVARD
 $795,000 4 / 3
 2,164sf N / Y
1369 BLUE STEM LANE
 $775,000 4 / 3
 2,589sf N / N
1562 ARBOR PARK DRIVE
 $775,000 4 / 2
 1,899sf N / N
2286 MARSH SEDGE LANE
 $770,000 4 / 3
 2,192sf N / N
110 LONGHORN ROAD
 $750,000 4 / 3
 2,673sf N / Y
1287 VERDANT GLADE PLACE
 $750,000 4 / 3
 3,020sf N / N
1418 LONE FEATHER TRAIL
 $729,995 4 / 2
 2,197sf N / N
1316 BLUE STEM LANE
 $725,000 4 / 2
 2,196sf Y / N
715 S RANGER BOULEVARD
 $695,000 4 / 3
 2,312sf N / Y
943 FAIRWAY DRIVE
 $689,900 4 / 3
 2,067sf N / N
1122 WILDMEADOW RUN
 $675,000 4 / 2
 1,770sf N / N
2833 PRINCE JOHN ROAD
 $669,000 4 / 2
 1,605sf N / N
2333 WESTMINSTER COURT
 $664,900 4 / 2
 1,877sf N / Y
2831 MULFORD AVENUE
 $635,000 4 / 2
 1,647sf N / N
7525 LODGE POLE TRAIL
 $600,000 4 / 2
 1,936sf N / Y
4353 STEED TERRACE
 $599,900 4 / 2
 2,275sf N / Y
1946 STRATHAVEN ROAD
 $599,000 4 / 3
 2,102sf N / N
2641 CARVELL COURT
 $575,000 4 / 2
 2,126sf N / Y
2627 AMBERGATE ROAD
 $575,000 4 / 3
 1,745sf N / N
333 CORNWALL ROAD
 $549,900 4 / 2
 1,660sf N / N
2054 EASTBROOK BOULEVARD
 $500,000 4 / 3
 2,031sf N / Y
2560 Franklin Ave.
$499,000 4 / 2
 1,514sf N / N
2008 HOUNDSLAKE DRIVE
 $490,000 4 / 2
 2,250sf N / N
2803 BANCHORY ROAD
 $474,000 4 / 2
 1,596sf N / N
1320 GLADIOLAS DR
 $474,000 4 / 2
 1,624sf N / N
316 BECKETT COURT
 $450,000 4 / 2
 1,651sf N / N
1564 LAWNDALE CIRCLE
 $450,000 4 / 2
 1,980sf N / N
1011 MANCHESTER CIRCLE
 $450,000 4 / 2
 1,699sf N / N
8433 COMMANDER COVE
 $435,000 4 / 2
 1,903sf N / N
501 HERITAGE BOULEVARD
 $435,000 4 / 2
 1,376sf N / Y
DRIVE
 $430,000 4 / 2
 1,296sf N / N
814 DENSMORE DR
 $425,000 4 / 2
 1,610sf N / N
1842 PURITAN AVENUE
 $419,000 4 / 2
 1,836sf N / N
1401 ASTER COURT
 $414,900 4 / 2
 1,653sf N / N
1849 VIBURNUM LANE
 $399,900 4 / 2
 1,627sf N / N
2512 EASTBROOK BOULEVARD
 $390,000 4 / 2
 1,607sf N / N
885 CARNATION DRIVE
 $385,000 4 / 2
 1,240sf N / Y
4965 ORANGE AVENUE
 $370,000 4 / 2
 1,444sf N / N

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1420 ALOMA AVENUE
 $2,190,000 3 / 3
 2,422sf Y / N
1133 BELLA LAGO COVE
 $2,100,000 3 / 2
 1,765sf Y / N
622 PENN PLACE
 $1,895,000 3 / 3
 2,767sf N / N
621 HUNTINGTON AVENUE
 $1,770,000 3 / 3
 2,399sf N / Y
641 NORTHWOOD CIRCLE
 $1,599,000 3 / 3
 2,756sf N / Y
1113 VIA DEL MAR
 $1,595,000 3 / 2
 2,012sf Y / N
462 W LYMAN AVENUE
 $1,595,000 3 / 2
 1,944sf N / N
1841 LAKE SPIER DRIVE
 $1,498,000 3 / 4
 2,467sf Y / N
1881 LAKE SPIER DRIVE
 $1,350,000 3 / 2
 1,750sf Y / N
240 KILLARNEY DRIVE
 $1,275,000 3 / 2
 1,329sf Y / N
120 BROADVIEW AVENUE
 $1,250,000 3 / 2
 1,747sf N / N
1870 WALKER AVENUE
 $1,199,000 3 / 2
 2,046sf N / N
1120 WISCONSIN AVENUE
 $1,079,000 3 / 3
 2,213sf N / N
1741 MIZELL AVENUE
 $998,000 3 / 2
 2,015sf N / N
1621 CHESTNUT AVENUE
 $899,000 3 / 2
 2,022sf N / N
437 N CAPEN AVENUE
 $849,000 3 / 2
 1,904sf N / N
1507 GOLFSIDE DRIVE
 $840,000 3 / 2
 2,003sf N / Y
338 BLUE HERON DRIVE
 $840,000 3 / 3
 2,017sf N / Y
1850 BRYAN AVENUE
 $729,000 3 / 2
 1,563sf N / N
860 N DENNING DRIVE
 $699,900 3 / 2
 1,411sf N / N
900 CARVER STREET
 $689,000 3 / 3
 1,794sf N / N
1416 BORDER DRIVE
 $675,000 3 / 1
 1,243sf N / N
433 GILBERT ROAD
 $669,900 3 / 2
 1,770sf N / Y
2418 EUSTON ROAD
 $657,777 3 / 2
 2,228sf N / N
1009 LAKE BELL DRIVE
 $650,000 3 / 2
 1,467sf Y / N
1871 BRYAN AVENUE
 $625,000 3 / 2
 1,232sf N / N
2708 LION HEART ROAD
 $614,500 3 / 2
 1,785sf N / Y
1707 HARMON AVENUE
 $599,000 3 / 2
 1,669sf N / N
4026 TENITA DRIVE
 $599,000 3 / 2
 2,031sf N / Y
1313 S DENNING DRIVE
 $589,900 3 / 2
 1,700sf N / N
1319 BESSMOR ROAD
 $589,000 3 / 2
 1,126sf N / N
1354 INDIANA AVENUE
 $574,900 3 / 2
 1,269sf N / N
2803 RIDDLE DRIVE
 $569,000 3 / 2
 1,709sf N / Y
7641 Village Green Drive
 $550,000 3 / 3
 2,130sf N / N
1003 LAKE BELL DRIVE
 $549,900 3 / 2
 1,837sf Y / N
1652 BERKSHIRE AVENUE
 $549,900 3 / 2
 1,498sf N / N
1741 WESTCHESTER AVENUE
 $549,000 3 / 2
 1,434sf N / N
330 ELKHORN COURT
 $544,900 3 / 2
 1,570sf N / N
1660 GLADIOLAS DRIVE
 $529,000 3 / 2
 2,047sf N / N
1438 TIERRA CIRCLE
 $514,900 3 / 2
 1,627sf N / Y
512 N LAKEMONT AVENUE
 $500,000 3 / 2
 1,413sf N / Y
525 OLOLU DRIVE
 $495,900 3 / 3
 1,786sf N / N
5316 HALYARD COURT
 $495,000 3 / 2
 1,380sf N / Y
2715 PRINCE JOHN ROAD
 $494,900 3 / 2
 1,565sf N / N
2703 TIERRA CIRCLE
 $469,000 3 / 2
 1,737sf N / Y
3641 HAWTHORNE LANE
 $465,000 3 / 2
 1,622sf N / Y
1052 MANCHESTER CIRCLE
 $460,000 3 / 2
 1,703sf N / N
5331 OAK COURT
 $460,000 3 / 2
 1,263sf N / Y
259 ORANGE TERRACE DRIVE
 $459,900 3 / 2
 1,248sf N / N
7384 GRAND AVENUE
 $450,000 3 / 2
 1,162sf N / N
2007 CORNELL AVENUE
 $449,000 3 / 2
 1,154sf N / N
5340 N LAKE BURKETT LANE
 $439,900 3 / 2
 1,746sf N / N
2041 JEWELL AVENUE
 $439,900 3 / 1
 1,508sf N / N
950 HANOVER AVENUE
 $439,000 3 / 2
 1,606sf N / N
7640 VILLAGE GREEN DR
 $439,000 3 / 2
 1,631sf N / Y
1955 ELAND AVENUE
 $439,000 3 / 2
 1,494sf N / N
1535 LAWNDALE CIRCLE
 $435,000 3 / 2
 1,676sf N / Y
3740 HAWTHORNE LANE
 $435,000 3 / 2
 1,645sf N / Y
405 Lake Fair Lane
$434,990 3 / 2
 N/A N / N
5409 ALBERT DRIVE
 $430,000 3 / 2
 1,483sf N / Y
1914 BONANZA COURT
 $429,999 3 / 2
 1,727sf N / N
2112 EASTBROOK BOULEVARD
 $429,998 3 / 2
 1,470sf N / N
1886 CLEMATIS LANE
 $425,000 3 / 2
 1,238sf N / N
1533 SPRINGTIME LOOP
 $415,000 3 / 2
 1,192sf N / Y
2568 LOTAFUN AVENUE
 $409,900 3 / 2
 1,201sf N / N
3440 ALLSTON LANE
 $405,000 3 / 2
 1,533sf N / N
1840 ASTER DRIVE
 $404,995 3 / 2
 1,667sf N / N
5588 GARDEN GROVE CIRCLE
 $400,000 3 / 2
 1,310sf N / N
5503 ALBERT DRIVE
 $399,990 3 / 2
 1,366sf N / N
1092 EASTBROOK BOULEVARD
 $399,000 3 / 2
 1,122sf N / Y
1605 PURITAN AVENUE
 $379,000 3 / 2
 1,285sf N / N
3374 HAMLET LOOP
 $355,000 3 / 2
 1,397sf N / N
3328 HAMLET LOOP
 $349,900 3 / 2
 1,397sf N / N
3562 BOUGAINVILLEA DRIVE
 $339,000 3 / 2
 1,149sf N / N
7393 GRAND AVENUE
 $325,000 3 / 2
 1,518sf N / N
1915 CARRIGAN AVENUE
 $299,900 3 / 1
 1,520sf N / N
2168 RIDGE DRIVE
 $299,000 3 / 1
 1,208sf N / N
2313 KNOLL STREET
 $284,000 3 / 2
 1,235sf N / N

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
560 OLOLU DRIVE
 $899,000 2 / 2
 1,086sf Y / N
1431 PALM AVENUE
 $850,000 2 / 2
 1,540sf N / N
1409 SUNSET DRIVE
 $669,000 2 / 1
 1,107sf N / N
981 ARAGON AVENUE
 $499,000 2 / 1
 857sf N / N
440 CAMBRIDGE BOULEVARD
 $369,900 2 / 1
 988sf N / N
811 OVERSPIN DRIVE
 $349,000 2 / 1
 749sf N / N
1941 OGLESBY AVENUE
 $340,000 2 / 1
 780sf N / N
2006 CORNELL AVENUE
 $328,000 2 / 1
 797sf N / N
846 DRIVER AVENUE
 $325,000 2 / 1
 824sf N / N

Property Location

Community Info

  • Winter Park
  • Price Range:
    $299,000-$7,250,000

© 2026 John Hernandez, Realtor ® - All Rights Reserved - Trademarks and Brands are the Property of their Respective Owners