Winter Park

Community Info

  • Price Range:
    $400,000-$8,500,000

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

8 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1860 VIA CONTESSA
 $2,790,000 8 / 6
 7,000sf N / Y

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
887 GEORGIA AVENUE
 $6,500,000 6 / 5
 5,759sf N / Y
575 PALMER AVENUE
 $2,800,000 6 / 5
 4,767sf N / Y
2234 VIA LUNA
 $2,070,000 6 / 3
 3,554sf N / Y
1451 LYNDALE BOULEVARD
 $1,999,993 6 / 4
 3,853sf N / Y
726/720 N PENNSYLVANIA AVENUE
 $1,275,000 6 / 4
 2,284sf N / N

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1112 PRESERVE POINT DRIVE
 $8,500,000 5 / 6
 6,502sf Y / Y
1181 VIA CAPRI
 $5,950,000 5 / 5
 4,448sf N / Y
1221 RICHMOND ROAD
 $5,800,000 5 / 5
 5,164sf N / Y
698 N NEW YORK AVENUE
 $5,549,000 5 / 5
 5,096sf N / 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
1660 PALMER AVENUE
 $4,950,000 5 / 6
 6,406sf N / Y
1525 GRANVILLE DRIVE
 $4,750,000 5 / 5
 5,211sf N / Y
1840 W FAWSETT ROAD
 $4,395,000 5 / 5
 4,129sf Y / Y
850 JUANITA RAEL
 $3,950,000 5 / 5
 3,183sf N / Y
1820 GLENCOE ROAD
 $3,895,000 5 / 5
 4,055sf N / Y
1761 LEGION DRIVE
 $3,499,999 5 / 5
 4,955sf N / Y
532 WORTHINGTON DRIVE
 $3,295,000 5 / 5
 3,974sf N / Y
1341 PLACE PICARDY
 $2,695,000 5 / 5
 4,469sf N / Y
450 LAKEWOOD DRIVE
 $2,500,000 5 / 4
 4,676sf N / Y
715 VIA BELLA
 $2,369,000 5 / 4
 4,328sf N / Y
1781 PINE AVENUE
 $2,300,000 5 / 4
 3,882sf N / Y
1560 WOODLAND AVENUE
 $2,150,000 5 / 4
 3,851sf N / Y
1710 ONECO AVENUE
 $2,149,000 5 / 4
 3,174sf N / Y
785 N PHELPS AVENUE
 $2,119,000 5 / 3
 2,964sf N / Y
1361 PALMER AVE.
 $2,095,000 5 / 3
 3,558sf N / Y
617 WORTHINGTON DRIVE
 $1,976,000 5 / 4
 3,533sf N / Y
2407 LAFAYETTE AVENUE
 $1,888,000 5 / 4
 3,133sf N / Y
2260 MULBRY DRIVE
 $1,800,000 5 / 4
 3,246sf N / N
1453 LYNDALE BOULEVARD
 $1,595,000 5 / 3
 3,292sf N / Y
130 W KINGS WAY
 $1,550,000 5 / 3
 3,145sf N / N
8041 LAKE WAUNATTA DRIVE
 $1,549,000 5 / 4
 5,329sf Y / Y
2105 FOSGATE DRIVE
 $1,295,000 5 / 4
 3,068sf N / Y
1807 MAGNOLIA AVENUE
 $1,201,000 5 / 3
 2,618sf N / N
7706 WAUNATTA COURT
 $1,050,000 5 / 3
 3,858sf Y / N
5325 CYPRESS RESERVE PLACE
 $935,000 5 / 3
 3,598sf N / Y
1927 ELAND AVENUE
 $893,000 5 / 3
 2,242sf N / N
730 W SWOOPE AVENUE
 $825,000 5 / 3
 2,132sf N / N
5618 WINTERBROOK WAY
 $770,000 5 / 4
 2,866sf N / N
5275 PINE LILY CIRCLE
 $738,000 5 / 3
 3,152sf N / Y
7895 PLEASANT PINE CIRCLE
 $725,000 5 / 3
 3,568sf N / N
1028 PRINCESS GATE BOULEVARD
 $479,900 5 / 2
 2,044sf N / N
2181 LINDEN ROAD
 $465,000 5 / 3
 1,442sf N / N
3642 PERIWINKLE DRIVE
 $455,000 5 / 3
 1,945sf N / N

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2661 VIA TUSCANY
 $6,600,000 4 / 4
 4,636sf N / Y
1760 VIA VENETIA
 $4,995,000 4 / 6
 6,242sf N / Y
1150 VIA SALERNO
 $4,750,000 4 / 5
 3,850sf N / Y
1161 VALENCIA AVENUE
 $4,650,000 4 / 4
 4,181sf N / Y
702 VIA BELLA
 $4,650,000 4 / 5
 3,720sf N / Y
1742 TEMPLE DRIVE
 $3,799,000 4 / 5
 3,658sf N / Y
1391 RICHMOND ROAD
 $3,499,500 4 / 5
 4,635sf Y / N
1910 GLENCOE ROAD
 $3,490,000 4 / 4
 4,205sf N / Y
541 W CANTON AVENUE
 $3,150,000 4 / 3
 3,553sf N / Y
1020 MAYFIELD AVENUE
 $2,950,000 4 / 3
 2,663sf N / N
1401 GREEN COVE ROAD
 $2,900,000 4 / 4
 5,416sf N / Y
2550 VENETIAN WAY
 $2,699,000 4 / 3
 4,875sf Y / N
521 S PHELPS AVENUE
 $2,455,000 4 / 4
 3,883sf N / Y
1760 BRYAN AVENUE
 $2,295,000 4 / 4
 3,005sf N / N
2522 LAFAYETTE AVENUE
 $2,270,000 4 / 3
 3,399sf N / Y
1752 CHESTNUT AVENUE
 $2,199,999 4 / 4
 3,314sf N / Y
2614 PARKLAND DR
 $2,095,000 4 / 3
 3,307sf N / Y
1840 BRYAN AVENUE
 $1,999,500 4 / 3
 3,727sf N / Y
633 BALMORAL ROAD
 $1,999,000 4 / 2
 2,674sf N / N
1521 CHESTNUT AVENUE
 $1,899,900 4 / 3
 2,843sf N / Y
1166 OAKS BOULEVARD
 $1,799,000 4 / 3
 2,860sf N / N
1660 WALNUT AVENUE
 $1,759,000 4 / 3
 2,172sf N / Y
446 ALBERTA DRIVE
 $1,750,000 4 / 2
 3,263sf N / N
1350 LYNDALE BOULEVARD
 $1,660,000 4 / 3
 3,478sf N / Y
607 ELLEN DRIVE
 $1,644,900 4 / 3
 2,812sf N / Y
1780 MIZELL AVE.
 $1,599,900 4 / 4
 2,743sf N / Y
7841 GEORGEANN STREET
 $1,595,000 4 / 4
 4,000sf Y / N
1831 MIZELL AVENUE
 $1,595,000 4 / 3
 3,204sf N / Y
952 MOSS LANE
 $1,474,950 4 / 2
 3,474sf N / Y
2401 LAFAYETTE AVENUE
 $1,425,000 4 / 3
 3,349sf N / N
1429 CHAPMAN CIRCLE
 $1,399,000 4 / 4
 3,116sf N / N
525 LAKEVIEW AVENUE
 $1,390,000 4 / 4
 3,253sf N / N
501 LAKEVIEW AVENUE
 $1,390,000 4 / 4
 3,253sf N / N
2922 REEF KNOT PLACE
 $1,349,000 4 / 3
 3,153sf Y / Y
1701 PALMER AVENUE
 $1,295,000 4 / 3
 2,841sf N / Y
1400 S PENNSYLVANIA AVENUE
 $1,290,000 4 / 3
 2,310sf N / N
1981 BLUE RIDGE ROAD
 $1,285,000 4 / 2
 2,750sf N / N
5236 LAKE HOWELL ROAD
 $1,275,000 4 / 3
 3,710sf N / Y
1341 LYNDALE BOULEVARD
 $1,200,000 4 / 3
 2,388sf N / N
215 SALVADOR SQUARE
 $1,195,000 4 / 3
 2,565sf N / Y
2607 Lafayette Ave
$1,095,000 4 / 3 / 1
 2,770sf N / N
2607 LAFAYETTE AVENUE
 $1,095,000 4 / 3
 2,770sf N / N
1444 PELICAN BAY TRAIL
 $1,070,000 4 / 2
 3,121sf Y / N
2890 WILD GINGER COURT
 $999,500 4 / 4
 3,408sf N / Y
1319 HEAVENLY COVE
 $998,000 4 / 3
 4,088sf Y / N
3870 TUCKS POINT
 $995,000 4 / 4
 3,323sf Y / N
208 BREWER AVENUE
 $980,000 4 / 3
 2,173sf N / N
210 LAUREL PARK COURT
 $965,000 4 / 3
 2,838sf N / Y
Lot #20 KAROLINA AVE
 $920,040 4 / 3
 2,662sf N / N
1018 TURNER ROAD
 $890,000 4 / 2
 2,237sf Y / Y
Lot #21 KAROLINA AVE
 $888,050 4 / 3
 2,662sf N / N
730 S RANGER BOULEVARD
 $875,000 4 / 4
 2,759sf N / Y
1090 WILDMEADOW RUN
 $864,900 4 / 3
 2,589sf N / N
1835 KAROLINA AVE
 $864,020 4 / 3
 2,662sf N / N
675 OVERSPIN DRIVE
 $829,000 4 / 3
 3,062sf N / N
2074 LAURELWOOD WAY
 $815,000 4 / 3
 2,185sf N / N
2222 MARSH SEDGE LANE
 $799,000 4 / 3
 2,192sf N / N
1740 ANZLE AVENUE
 $795,000 4 / 2
 1,808sf N / Y
AVENUE
 $785,000 4 / 3
 2,878sf N / N
1340 BLUE STEM LANE
 $775,000 4 / 3
 2,587sf N / N
2167 MARSH SEDGE LANE
 $775,000 4 / 2
 2,637sf N / N
620 DARCEY DR
 $759,000 4 / 2
 2,076sf N / N
744 CORNWALL ROAD
 $750,000 4 / 2
 1,968sf N / N
1465 LONE FEATHER TRAIL
 $749,900 4 / 3
 2,582sf N / N
770 W WEBSTER AVENUE
 $725,000 4 / 2
 1,008sf N / N
607 DUNBLANE DRIVE
 $719,000 4 / 2
 2,046sf N / N
1729 GOLFSIDE DRIVE
 $700,000 4 / 2
 2,372sf Y / N
3110 HEARTLEAF PLACE
 $658,900 4 / 3
 2,860sf Y / Y
3115 HEARTLEAF PLACE
 $650,000 4 / 3
 2,846sf N / N
346 ELKHORN COURT
 $649,999 4 / 2
 1,891sf N / Y
2330 COLDSTREAM DRIVE
 $649,900 4 / 2
 1,750sf N / N
8065 PLEASANT PINE CIRCLE
 $560,000 4 / 2
 1,843sf N / N
2627 AMBERGATE ROAD
 $550,000 4 / 3
 1,805sf N / Y
5255 SEMINOLE AVENUE
 $545,000 4 / 3
 2,170sf N / N
240 ORANGE TERRACE DRIVE
 $545,000 4 / 2
 1,718sf N / N
8162 LAZY BEAR LANE
 $539,500 4 / 2
 1,843sf N / N
7864 PLEASANT PINE CIRCLE
 $539,000 4 / 2
 2,182sf N / N
1713 W CHERYL DRIVE
 $525,000 4 / 2
 2,030sf N / Y
8136 LAZY BEAR LANE
 $514,900 4 / 2
 1,843sf N / N
2844 SCARLET ROAD
 $509,000 4 / 2
 1,508sf N / N
TERRACE
 $500,000 4 / 2
 2,075sf N / Y
7679 BENT BOW TRAIL
 $495,000 4 / 2
 2,616sf N / N
5338 TANGERINE AVENUE
 $489,500 4 / 2
 2,195sf N / Y
1742 WILLA CIRCLE
 $480,000 4 / 2
 2,313sf N / N
7104 WRENWOOD WAY
 $469,900 4 / 2
 1,778sf N / N
2464 LOTAFUN AVENUE
 $450,000 4 / 3
 1,804sf N / N
1660 TREMONT LANE
 $450,000 4 / 2
 1,980sf N / N
1354 TIERRA CIRCLE
 $449,900 4 / 2
 1,827sf N / N
1849 VIBURNUM LANE
 $449,900 4 / 2
 1,627sf N / N
1621 PURITAN
 $440,000 4 / 2
 1,765sf Y / Y
1362 TIERRA CIRCLE
 $440,000 4 / 3
 2,179sf N / N
1842 PURITAN AVENUE
 $439,000 4 / 2
 1,836sf N / N
2829 ALOMA AVENUE
 $430,000 4 / 2
 1,821sf N / Y
330 ELKHORN COURT
 $419,900 4 / 2
 1,570sf N / N
3415 N GOLDENROD RD
 $410,000 4 / 3
 1,906sf N / Y

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1120 PALMER AVENUE
 $4,250,000 3 / 3
 3,413sf N / Y
922 N PENNSYLVANIA AVENUE
 $2,249,000 3 / 4
 3,440sf N / N
825 PALMER AVENUE
 $1,799,000 3 / 3
 3,297sf Y / Y
1270 ARLINGTON PLACE
 $1,700,000 3 / 4
 2,964sf N / Y
1644 HIBISCUS AVENUE
 $1,449,000 3 / 3
 2,145sf N / Y
1741 PALMER AVENUE
 $1,445,000 3 / 3
 2,351sf N / N
800 HAMILTON PLACE COURT
 $1,300,000 3 / 3
 3,363sf N / N
1450 CHESTNUT AVENUE
 $1,300,000 3 / 3
 1,942sf N / Y
901 PALMER AVENUE
 $1,100,000 3 / 2
 1,843sf N / N
632 COUNTRY CLUB DRIVE
 $1,050,000 3 / 2
 2,342sf Y / Y
913 MOSS LANE
 $975,000 3 / 2
 1,887sf N / N
250 CORTLAND AVENUE
 $960,000 3 / 2
 2,114sf N / Y
2823 WRIGHT AVENUE
 $949,900 3 / 2
 1,536sf Y / N
915 GARDEN DRIVE
 $945,000 3 / 3
 2,456sf N / Y
2128 Sycamore Dr
$825,000 3 / 2
 1,760sf N / N
2128 SYCAMORE DRIVE
 $825,000 3 / 2
 1,760sf N / N
441 N CAPEN AVENUE
 $790,000 3 / 2
 1,745sf N / N
625 BRECHIN DRIVE
 $765,000 3 / 2
 1,827sf N / N
2418 WHITEHALL CIRCLE
 $765,000 3 / 2
 2,134sf N / N
726 N PENNSYLVANIA AVENUE
 $750,000 3 / 2
 1,167sf N / N
2478 WHITEHALL CIRCLE
 $720,000 3 / 2
 2,256sf N / N
2190 TEMPLE DRIVE
 $700,000 3 / 2
 1,442sf N / Y
1174 WILDMEADOW RUN
 $689,000 3 / 2
 1,770sf N / N
1147 WILDMEADOW RUN
 $688,000 3 / 3
 2,002sf N / N
1399 ALOMA AVENUE
 $675,000 3 / 2
 1,804sf N / N
5150 OLD HOWELL BRANCH ROAD
 $649,900 3 / 1
 2,108sf N / N
2758 BANCHORY ROAD
 $649,000 3 / 2
 1,539sf N / Y
720 W WEBSTER AVENUE
 $649,000 3 / 2
 1,356sf N / N
2812 WOODSIDE AVENUE
 $625,000 3 / 2
 1,842sf N / N
2612 LAFAYETTE AVENUE
 $599,000 3 / 2
 2,447sf N / N
1123 FAIRWAY DRIVE
 $575,000 3 / 2
 1,772sf N / N
212 BLOSSOM LANE
 $565,000 3 / 2
 1,771sf N / N
701 DENTON ROAD
 $565,000 3 / 2
 2,268sf N / Y
720 N PENNSYLVANIA AVENUE
 $550,000 3 / 2
 1,115sf N / N
2708 LION HEART ROAD
 $550,000 3 / 2
 1,785sf N / Y
240 CAMBRIDGE BOULEVARD
 $535,000 3 / 2
 1,630sf N / N
1116 FAIRWAY DRIVE
 $525,000 3 / 2
 1,738sf N / N
2381 ROXBURY ROAD
 $519,000 3 / 2
 1,645sf N / N
1339 MONTE LANE
 $510,000 3 / 2
 2,200sf N / Y
2774 BANCHORY ROAD
 $500,000 3 / 2
 1,560sf N / N
1924 SUMMERFIELD ROAD
 $499,999 3 / 2
 1,492sf N / N
7730 BROKEN ARROW TRAIL
 $485,000 3 / 2
 2,706sf N / Y
1173 VALLEY CREEK RUN
 $482,900 3 / 2
 1,906sf N / N
2831 LION HEART ROAD
 $480,000 3 / 2
 1,978sf N / N
3054 BLUEBROOK DRIVE
 $479,900 3 / 2
 1,939sf N / Y
1608 BOMI CIRCLE
 $475,000 3 / 2
 1,807sf N / N
1932 HOUNDSLAKE DRIVE
 $475,000 3 / 2
 1,671sf N / Y
2835 BONGART ROAD
 $469,900 3 / 3
 1,880sf N / Y
5331 OAK COURT
 $460,000 3 / 2
 1,263sf N / Y
1564 CAVENDISH ROAD
 $450,000 3 / 1
 1,140sf N / N
1914 BONANZA COURT
 $450,000 3 / 2
 1,727sf N / N
105 CONRAD COURT
 $429,999 3 / 2
 1,573sf N / N
3107 ASH PARK LOOP
 $425,000 3 / 2
 1,518sf N / N
3425 FERNDELL DRIVE
 $420,100 3 / 2
 1,516sf N / N
5346 CYPRESS DRIVE
 $419,900 3 / 2
 1,670sf N / N
616 ELLENDALE DRIVE
 $419,900 3 / 2
 1,405sf N / Y
920 GLORIOSA AVENUE
 $409,988 3 / 2
 1,540sf N / N
2320 HIGH STREET
 $400,000 3 / 2
 1,071sf N / N

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
141 W LAKE SUE AVENUE
 $1,690,000 2 / 1
 1,559sf N / N
2260 HAWICK LANE
 $995,000 2 / 1
 1,374sf N / N
3601 MIDIRON DRIVE
 $459,000 2 / 1
 954sf N / N

Property Location

Community Info

  • Winter Park
  • Price Range:
    $400,000-$8,500,000

© 2025 John Hernandez, Realtor ® - All Rights Reserved - Trademarks and Brands are the Property of their Respective Owners