Winter Park

Community Info

  • Price Range:
    $269,000-$8,950,000

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

7 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1120 PRESERVE POINT DRIVE
 $8,950,000 7 / 9
 11,255sf Y / Y
1445 VIA SANGRO PLACE
 $1,399,990 7 / 5
 5,021sf N / Y

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1451 LYNDALE BOULEVARD
 $1,999,993 6 / 4
 3,853sf N / Y

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1112 PRESERVE POINT DRIVE
 $8,500,000 5 / 6
 6,502sf Y / Y
550 PALMER AVENUE
 $6,895,000 5 / 6
 5,939sf N / Y
1400 ALABAMA DRIVE
 $5,895,000 5 / 5
 7,916sf Y / Y
2211 Azalea Pl
$5,495,000 5 / 6 / 1
 7,278sf Y / Y
2211 AZALEA PLACE
 $5,495,000 5 / 6
 7,278sf Y / Y
1221 RICHMOND ROAD
 $5,450,000 5 / 5
 5,164sf N / Y
1660 PALMER AVENUE
 $4,950,000 5 / 6
 6,406sf N / Y
1751 GLENCOE ROAD
 $3,895,000 5 / 5
 4,520sf N / Y
1820 GLENCOE ROAD
 $3,825,000 5 / 5
 4,055sf N / Y
207 E KINGS WAY
 $3,650,000 5 / 4
 3,719sf N / Y
516 HENKEL CIRCLE
 $3,499,000 5 / 6
 4,143sf Y / N
1761 LEGION DRIVE
 $3,399,999 5 / 5
 4,955sf N / Y
473 FLETCHER PLACE
 $3,250,000 5 / 5
 4,296sf N / Y
457 E NEW ENGLAND AVENUE
 $3,100,000 5 / 4
 3,847sf N / N
1494 WESTCHESTER AVENUE
 $2,990,000 5 / 4
 3,711sf N / Y
2503 VERSAILLES AVENUE
 $2,775,000 5 / 5
 4,026sf N / Y
426 WORTHINGTON DRIVE
 $2,679,000 5 / 4
 3,520sf N / Y
2812 MULFORD AVENUE
 $2,495,000 5 / 5
 3,656sf N / Y
1205 MAYFIELD AVENUE
 $2,350,000 5 / 4
 3,948sf N / Y
1885 TEMPLE DRIVE
 $2,295,000 5 / 3
 3,691sf N / Y
2412 CHANTILLY AVENUE
 $2,295,000 5 / 6
 4,506sf N / Y
2722 EASTERN PARKWAY
 $2,289,000 5 / 4
 3,334sf N / Y
2001 LAKE DRIVE
 $2,165,000 5 / 4
 4,798sf Y / Y
1540 PALM AVENUE
 $1,999,000 5 / 3
 3,423sf N / Y
617 WORTHINGTON DRIVE
 $1,770,000 5 / 4
 3,533sf N / Y
1473 BERKSHIRE AVENUE
 $1,589,904 5 / 4
 2,895sf N / Y
1523 MILLER AVENUE
 $1,550,000 5 / 4
 3,164sf N / Y
5325 CYPRESS RESERVE PLACE
 $918,000 5 / 3
 3,598sf N / Y
2215 MARSH SEDGE LANE
 $799,000 5 / 2
 2,646sf N / Y
2612 ROXBURY ROAD
 $698,000 5 / 3
 2,472sf N / N
2920 ABBEY COURT
 $640,000 5 / 3
 2,312sf N / Y

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2661 VIA TUSCANY
 $6,600,000 4 / 4
 4,636sf N / Y
1150 VIA SALERNO
 $4,750,000 4 / 5
 3,850sf N / Y
1336 COLLEGE POINT
 $4,595,000 4 / 3
 3,181sf Y / Y
1161 VALENCIA AVENUE
 $4,445,000 4 / 4
 4,181sf N / Y
1910 GLENCOE ROAD
 $3,490,000 4 / 4
 4,205sf N / Y
2361 MULBRY DRIVE
 $2,395,000 4 / 4
 3,111sf N / Y
2299 VIA TUSCANY
 $2,345,000 4 / 3
 3,986sf N / Y
1841 HARLAND PARK DRIVE
 $1,999,000 4 / 3
 3,470sf N / N
319 SANTIAGO DRIVE
 $1,990,000 4 / 4
 3,515sf N / Y
2614 PARKLAND DRIVE
 $1,984,100 4 / 3
 3,307sf N / Y
633 BALMORAL ROAD
 $1,875,000 4 / 2
 2,674sf Y / N
446 ALBERTA DRIVE
 $1,750,000 4 / 2
 3,263sf N / N
2430 CHANTILLY AVENUE
 $1,665,000 4 / 4
 2,916sf N / Y
607 ELLEN DRIVE
 $1,630,000 4 / 3
 2,812sf N / Y
1166 OAKS BOULEVARD
 $1,590,000 4 / 3
 2,860sf N / N
1408 CHAPMAN CIRCLE
 $1,525,000 4 / 4
 3,237sf N / Y
102 BELL PLACE
 $1,499,000 4 / 3
 2,459sf N / Y
1807 YORKSHIRE DRIVE
 $1,450,000 4 / 4
 3,565sf N / N
850 JUANITA RAEL
 $1,425,000 4 / 3
 2,306sf N / Y
525 LAKEVIEW AVENUE
 $1,390,000 4 / 4
 3,253sf N / N
501 LAKEVIEW AVENUE
 $1,390,000 4 / 4
 3,253sf N / N
2015 SUMMERFIELD ROAD
 $1,375,000 4 / 4
 3,024sf N / Y
952 MOSS LANE
 $1,359,950 4 / 2
 3,474sf N / Y
1673 MAYFIELD AVENUE
 $1,300,000 4 / 4
 2,540sf N / Y
1429 CHAPMAN CIRCLE
 $1,299,000 4 / 4
 3,116sf N / N
2922 REEF KNOT PLACE
 $1,295,000 4 / 3
 3,153sf Y / Y
1981 BLUE RIDGE ROAD
 $1,180,000 4 / 2
 2,750sf N / N
1092 WADING WATERS CIRCLE
 $1,128,500 4 / 3
 3,057sf Y / Y
2607 Lafayette Ave
$1,095,000 4 / 3 / 1
 2,770sf N / N
1245 WADING WATERS CIRCLE
 $1,065,000 4 / 3
 3,050sf N / Y
1444 PELICAN BAY TRAIL
 $999,950 4 / 2
 3,121sf Y / N
208 BREWER AVENUE
 $925,000 4 / 3
 2,173sf N / N
Lot #21 KAROLINA AVE
 $916,050 4 / 3
 2,662sf N / N
1780 BRYAN AVENUE
 $800,000 4 / 2
 1,617sf N / N
2632 MANDAN TRAIL
 $799,900 4 / 2
 2,441sf N / Y
2222 MARSH SEDGE LANE
 $789,000 4 / 3
 2,192sf N / N
1213 LINDENWOOD LANE
 $750,000 4 / 2
 2,505sf N / N
1340 BLUE STEM LANE
 $740,000 4 / 3
 2,587sf N / N
1127 WILDMEADOW RUN
 $695,000 4 / 2
 2,196sf N / N
2087 LAURELWOOD WAY
 $679,000 4 / 2
 1,920sf N / N
607 DUNBLANE DRIVE
 $675,000 4 / 2
 2,046sf N / N
1985 JAPONICA ROAD
 $649,000 4 / 2
 2,096sf N / Y
3115 HEARTLEAF PLACE
 $610,000 4 / 3
 2,846sf N / N
3102 HEARTLEAF PLACE
 $609,577 4 / 3
 2,672sf N / N
2350 CADY WAY
 $575,000 4 / 2
 1,854sf N / N
731 BONGART ROAD
 $570,000 4 / 3
 1,526sf N / Y
AVENUE
 $540,000 4 / 3
 2,878sf N / N
4190 BEAR GULLY ROAD
 $540,000 4 / 2
 2,058sf N / N
2665 TIERRA CIRCLE
 $539,000 4 / 2
 1,885sf N / Y
2189 SUSSEX ROAD
 $535,000 4 / 2
 1,776sf N / Y
2217 SUSSEX ROAD
 $530,000 4 / 2
 2,092sf N / Y
422 S RANGER BOULEVARD
 $520,000 4 / 2
 1,680sf N / N
240 ORANGE TERRACE DRIVE
 $515,000 4 / 2
 1,718sf N / N
2627 AMBERGATE ROAD
 $510,000 4 / 3
 1,805sf N / Y
1422 TIERRA CIRCLE
 $499,000 4 / 2
 1,827sf N / Y
1742 WILLA CIRCLE
 $470,000 4 / 2
 2,313sf N / N
2206 BONANZA AVENUE
 $455,000 4 / 2
 1,776sf N / N
1347 ORCHID AVENUE
 $449,900 4 / 2
 1,490sf N / N
1842 PURITAN AVENUE
 $439,000 4 / 2
 1,836sf N / N
1849 VIBURNUM LANE
 $425,000 4 / 2
 1,627sf N / N
1816 IVY LANE
 $425,000 4 / 2
 1,725sf N / N
5047 FERNCREST DRIVE
 $349,000 4 / 2
 1,242sf N / N

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1401 GREEN COVE ROAD
 $2,900,000 3 / 4
 5,483sf N / Y
1624 BARCELONA WAY
 $2,350,000 3 / 3
 3,828sf N / Y
1630 CHESTNUT AVENUE
 $1,725,000 3 / 4
 3,164sf N / Y
1600 PALMER AVENUE
 $1,200,000 3 / 2
 2,550sf N / N
1150 KENWOOD AVENUE
 $1,190,000 3 / 2
 2,557sf N / N
250 CORTLAND AVENUE
 $950,000 3 / 2
 2,114sf N / Y
676 DUNBLANE DRIVE
 $750,000 3 / 2
 1,827sf N / Y
860 N DENNING DRIVE
 $749,900 3 / 2
 1,290sf N / N
636 DUNBLANE DRIVE
 $725,000 3 / 2
 1,803sf N / N
3018 NORTHWOOD BOULEVARD
 $719,000 3 / 2
 1,761sf N / N
1427 LAKE FLORENCE WAY
 $695,000 3 / 2
 2,193sf N / Y
1399 ALOMA AVENUE
 $665,000 3 / 2
 1,804sf N / N
2811 EASTERN PARKWAY
 $665,000 3 / 2
 1,433sf N / Y
1489 ASTER COURT
 $650,000 3 / 2
 2,227sf Y / N
5150 OLD HOWELL BRANCH ROAD
 $634,900 3 / 1
 2,108sf N / N
2817 FITZOOTH DRIVE
 $619,900 3 / 2
 1,619sf N / Y
1451 Cavendish Road
 $619,500 3 / 2
 1,437sf N / N
701 DENTON ROAD
 $565,000 3 / 2
 2,268sf N / Y
7641 Village Green Drive
 $550,000 3 / 3
 2,130sf N / N
346 S RANGER BOULEVARD
 $520,000 3 / 2
 1,592sf N / N
1280 GLADIOLAS DR
 $499,500 3 / 2
 1,624sf N / Y
1518 PINEWOOD DRIVE
 $489,900 3 / 2
 1,197sf N / N
2774 BANCHORY ROAD
 $470,000 3 / 2
 1,560sf N / N
2152 CONIFER AVENUE
 $460,000 3 / 2
 1,694sf N / Y
1932 HOUNDSLAKE DRIVE
 $459,990 3 / 2
 1,671sf N / Y
1816 MEADOWGOLD LANE
 $459,000 3 / 2
 1,546sf N / Y
714 DENTON ROAD
 $449,900 3 / 3
 1,786sf N / N
1914 BONANZA COURT
 $435,000 3 / 2
 1,727sf N / N
740 BAFFIE AVENUE
 $420,000 3 / 2
 1,456sf N / N
1007 EARLY AVENUE
 $399,990 3 / 2
 1,721sf N / N
616 ELLENDALE DRIVE
 $398,000 3 / 2
 1,405sf N / Y
1531 LAWNDALE CIRCLE
 $386,000 3 / 2
 1,300sf N / N
958 DUPONT AVENUE
 $381,000 3 / 2
 1,572sf N / N
1378 CHILEAN LANE
 $379,990 3 / 2
 1,424sf N / N
1816 AZALEA AVENUE
 $369,900 3 / 2
 1,584sf N / N
1573 LAWNDALE CIRCLE
 $350,000 3 / 2
 1,446sf N / N
DRIVE
 $335,000 3 / 2
 1,104sf N / N
121 STEFANIK ROAD
 $327,500 3 / 2
 1,392sf N / N
1920 CARRIGAN AVENUE
 $315,000 3 / 2
 1,242sf N / N
2634 EXUMA WAY
 $289,900 3 / 2
 1,284sf N / N

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
240 Lake Sue Ave E
$1,107,750 2 / 2
 1,329sf N / N
560 OLOLU DRIVE
 $949,000 2 / 2
 1,086sf Y / N
230 STRATHY LANE
 $499,000 2 / 1
 920sf N / N
875 W LYMAN AVENUE
 $475,000 2 / 2
 760sf N / N
2009 CORNELL AVENUE
 $269,000 2 / 1
 762sf N / N

Vacant Land

Address Price Bed / Baths Interior Space WF / Pool
887 GEORGIA AVENUE
 $5,900,000 0 /
5,759sf N / Y
1302 RAINTREE PLACE
 $5,300,000 0 /
4,738sf N / Y
702 VIA BELLA
 $4,250,000 0 /
3,720sf N / Y
1821 ENGLEWOOD ROAD
 $3,295,000 0 /
3,863sf N / Y
525 S LAKEMONT AVENUE
 $2,350,000 0 /
3,330sf N / Y
1510 MILLER AVENUE
 $1,634,900 0 /
3,252sf N / Y
1540 MILLER AVENUE
 $1,399,900 0 /
2,984sf N / Y
726/720 N PENNSYLVANIA AVENUE
 $1,215,000 0 /
2,284sf N / N
1822 GREENWICH AVENUE
 $1,199,900 0 /
1,627sf N / N
2607 LAFAYETTE AVENUE
 $1,095,000 0 /
2,770sf N / N
870 CARVER STREET
 $975,000 0 /
1,875sf N / N
668 OVERSPIN DRIVE
 $950,000 0 /
2,509sf N / N
1324 INDIANA AVENUE
 $745,000 0 /
1,692sf N / N
726 N PENNSYLVANIA AVENUE
 $695,000 0 /
1,167sf N / N
428 SELKIRK DRIVE
 $650,000 0 /
1,782sf N / Y
2330 COLDSTREAM DRIVE
 $649,900 0 /
1,750sf N / N
2758 BANCHORY ROAD
 $598,000 0 /
1,539sf N / Y
720 N PENNSYLVANIA AVENUE
 $550,000 0 /
1,115sf N / N
1713 W CHERYL DRIVE
 $525,000 0 /
2,030sf N / Y
3054 BLUEBROOK DRIVE
 $469,900 0 /
1,939sf N / Y
3425 FERNDELL DRIVE
 $409,000 0 /
1,516sf N / N

Property Location

Community Info

  • Winter Park
  • Price Range:
    $269,000-$8,950,000

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