Winter Park

Community Info

  • Price Range:
    $400,000-$10,900,000

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
 $2,750,000 8 / 6
 7,000sf N / Y

7 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1120 PRESERVE POINT DRIVE
 $10,900,000 7 / 9
 11,255sf Y / Y

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
141 S PHELPS AVENUE
 $3,595,000 6 / 5
 5,878sf 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
1299 HARDING STREET
 $1,869,000 6 / 5
 3,784sf N / N
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
1400 ALABAMA DRIVE
 $6,500,000 5 / 5
 7,916sf Y / Y
2211 Azalea Pl
$6,180,000 5 / 6 / 1
 7,278sf Y / Y
2211 AZALEA PLACE
 $6,180,000 5 / 6
 7,278sf Y / Y
1660 PALMER AVENUE
 $5,200,000 5 / 6
 6,406sf N / Y
2161 SHARON ROAD
 $4,750,000 5 / 6
 6,338sf N / Y
1840 W FAWSETT ROAD
 $4,395,000 5 / 5
 4,129sf Y / Y
1782 PINE AVENUE
 $4,100,000 5 / 6
 4,782sf N / Y
1820 GLENCOE ROAD
 $3,895,000 5 / 5
 4,055sf N / Y
2171 FORREST ROAD
 $3,750,000 5 / 6
 4,565sf N / Y
1761 LEGION DRIVE
 $3,599,999 5 / 5
 4,955sf N / Y
473 FLETCHER PLACE
 $3,400,000 5 / 5
 4,296sf N / Y
1820 ENGLEWOOD ROAD
 $3,300,000 5 / 5
 4,263sf N / Y
532 WORTHINGTON DRIVE
 $3,295,000 5 / 5
 3,974sf N / Y
1730 WINCHESTER DRIVE
 $3,150,000 5 / 5
 4,080sf N / Y
1891 LAKE SPIER DRIVE
 $2,999,000 5 / 4
 3,932sf Y / Y
2652 LAKE HOWELL LANE
 $2,849,000 5 / 3
 4,200sf Y / N
1341 PLACE PICARDY
 $2,800,000 5 / 5
 4,469sf N / Y
1400 PLACE PICARDY
 $2,725,000 5 / 5
 4,338sf N / Y
1781 PINE AVENUE
 $2,700,000 5 / 4
 3,882sf N / Y
1630 LASBURY AVENUE
 $2,650,000 5 / 3
 4,912sf N / Y
450 LAKEWOOD DRIVE
 $2,500,000 5 / 4
 4,676sf N / Y
2412 CHANTILLY AVENUE
 $2,389,000 5 / 6
 4,506sf N / Y
1361 PALMER AVE.
 $2,195,000 5 / 3
 3,558sf N / Y
1560 WOODLAND AVENUE
 $2,150,000 5 / 4
 3,851sf N / Y
785 N PHELPS AVENUE
 $2,119,000 5 / 4
 2,964sf N / Y
617 WORTHINGTON DRIVE
 $1,976,000 5 / 4
 3,533sf N / Y
1355 HIBISCUS AVENUE
 $1,925,000 5 / 5
 4,155sf N / Y
4469 OLD BEAR RUN
 $1,899,000 5 / 4
 4,288sf Y / 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
1742 BARCELONA WAY
 $1,625,000 5 / 6
 3,626sf N / Y
1417 MILLER AVENUE
 $1,599,900 5 / 4
 3,312sf N / Y
1733 HARMON AVENUE
 $1,595,000 5 / 4
 3,267sf N / Y
8041 LAKE WAUNATTA DRIVE
 $1,590,000 5 / 4
 5,329sf Y / Y
1473 BERKSHIRE AVENUE
 $1,575,000 5 / 4
 2,895sf N / Y
1327 BRIDGEPORT DRIVE
 $1,499,000 5 / 4
 4,181sf N / Y
2105 FOSGATE DRIVE
 $1,325,000 5 / 4
 3,068sf N / Y
7440 ALOMA AVE
 $1,299,000 5 / 4
 4,435sf N / Y
1807 MAGNOLIA AVENUE
 $1,200,000 5 / 3
 2,618sf N / N
7706 WAUNATTA COURT
 $1,195,000 5 / 3
 3,858sf Y / N
2880 OLD CASTLE DRIVE
 $1,120,000 5 / 4
 3,839sf N / Y
2011 SOARING OAK WAY
 $1,080,000 5 / 4
 4,307sf N / N
2330 WESTMINSTER COURT
 $999,000 5 / 3
 3,296sf N / N
3011 TEMPLE TRAIL
 $950,000 5 / 2
 2,406sf N / Y
5325 CYPRESS RESERVE PLACE
 $935,000 5 / 3
 3,598sf N / Y
730 W SWOOPE AVENUE
 $850,000 5 / 3
 2,132sf N / N
5618 WINTERBROOK WAY
 $784,000 5 / 4
 2,866sf N / N
5275 PINE LILY CIRCLE
 $742,000 5 / 3
 3,152sf N / Y
7895 PLEASANT PINE CIRCLE
 $730,000 5 / 3
 3,568sf N / N
5073 LAKE HOWELL ROAD
 $539,500 5 / 2
 2,272sf N / Y

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2661 VIA TUSCANY
 $8,500,000 4 / 4
 4,564sf N / Y
1150 VIA SALERNO
 $4,750,000 4 / 5
 3,850sf N / Y
1581 FOREST AVENUE
 $4,175,000 4 / 4
 4,683sf N / Y
1742 TEMPLE DRIVE
 $3,975,000 4 / 5
 3,658sf N / Y
182 N PHELPS AVENUE
 $3,600,000 4 / 5
 4,812sf 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 / Y
1401 GREEN COVE ROAD
 $2,900,000 4 / 4
 5,416sf N / Y
2550 VENETIAN WAY
 $2,799,000 4 / 3
 4,875sf Y / N
185 SYLVAN BOULEVARD
 $2,590,000 4 / 4
 3,138sf N / Y
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
2614 PARKLAND DRIVE
 $2,165,000 4 / 3
 3,307sf N / Y
1521 CHESTNUT AVENUE
 $1,999,900 4 / 3
 3,117sf 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
446 ALBERTA DRIVE
 $1,825,000 4 / 2
 3,263sf N / N
1780 MIZELL AVE.
 $1,795,000 4 / 4
 2,743sf N / Y
1702 ARBOR PARK DRIVE
 $1,775,000 4 / 3
 2,950sf N / Y
2402.5 TEMPLE DRIVE
 $1,699,000 4 / 4
 3,248sf N / Y
1831 MIZELL AVENUE
 $1,695,000 4 / 3
 3,204sf N / Y
1350 LYNDALE BOULEVARD
 $1,675,000 4 / 3
 3,478sf N / Y
607 ELLEN DRIVE
 $1,664,900 4 / 3
 2,812sf N / Y
7841 GEORGEANN STREET
 $1,645,000 4 / 4
 4,000sf Y / N
1429 CHAPMAN CIRCLE
 $1,599,999 4 / 4
 3,116sf N / N
952 MOSS LANE
 $1,554,950 4 / 2
 3,474sf N / Y
2401 LAFAYETTE AVENUE
 $1,491,000 4 / 3
 3,349sf N / N
2408 LAFAYETTE AVENUE
 $1,490,000 4 / 3
 2,838sf N / Y
1600 BARCELONA WAY
 $1,475,000 4 / 3
 3,014sf N / Y
1420 PALMER AVENUE
 $1,449,900 4 / 3
 2,953sf N / Y
2015 SUMMERFIELD ROAD
 $1,425,000 4 / 4
 3,024sf N / Y
2922 REEF KNOT PLACE
 $1,395,000 4 / 3
 3,153sf Y / Y
1400 S PENNSYLVANIA AVENUE
 $1,300,000 4 / 3
 2,310sf N / N
1341 LYNDALE BOULEVARD
 $1,299,000 4 / 3
 2,388sf N / N
1701 PALMER AVENUE
 $1,295,000 4 / 3
 2,841sf N / Y
1611 WALNUT AVENUE
 $1,265,000 4 / 3
 2,635sf N / N
2890 WILD GINGER COURT
 $1,225,000 4 / 4
 3,408sf N / Y
4048 GILDER ROSE PLACE
 $1,210,000 4 / 3
 3,321sf N / Y
4107 GABRIELLA LANE
 $1,200,000 4 / 3
 3,074sf Y / Y
1611 CHESTNUT AVENUE
 $1,195,000 4 / 4
 2,916sf N / N
2607 Lafayette Ave
$1,180,000 4 / 3 / 1
 2,770sf N / N
2607 LAFAYETTE AVENUE
 $1,180,000 4 / 3
 2,770sf N / N
1444 PELICAN BAY TRAIL
 $1,070,000 4 / 2
 3,121sf Y / N
1319 HEAVENLY COVE
 $998,000 4 / 3
 4,088sf Y / N
210 LAUREL PARK COURT
 $995,000 4 / 3
 2,838sf N / Y
1840 BISCAYNE DRIVE
 $949,000 4 / 3
 2,641sf N / N
1018 TURNER ROAD
 $940,000 4 / 2
 2,237sf Y / Y
1263 VERDANT GLADE PLACE
 $885,000 4 / 3
 2,589sf N / N
1090 WILDMEADOW RUN
 $875,000 4 / 3
 2,589sf N / N
675 OVERSPIN DRIVE
 $839,900 4 / 3
 2,962sf N / N
2168 MARSH SEDGE LANE
 $819,000 4 / 3
 2,192sf N / Y
AVENUE
 $815,000 4 / 3
 2,878sf N / N
627 DARCEY DRIVE
 $775,000 4 / 2
 2,509sf N / N
1340 BLUE STEM LANE
 $775,000 4 / 3
 2,587sf N / N
620 DARCEY DR
 $775,000 4 / 2
 2,076sf N / N
607 DUNBLANE DRIVE
 $729,000 4 / 2
 2,046sf N / N
3759 KINSLEY PLACE
 $700,000 4 / 2
 2,251sf N / Y
3115 HEARTLEAF PLACE
 $684,999 4 / 3
 2,846sf N / N
3110 HEARTLEAF PLACE
 $680,800 4 / 3
 2,860sf Y / Y
1792 KILLARNEY DRIVE
 $665,000 4 / 3
 2,082sf N / N
1507 GOLFSIDE DRIVE
 $650,000 4 / 2
 2,003sf N / Y
1875 STAUNTON AVENUE
 $599,000 4 / 2
 2,036sf N / N
8162 LAZY BEAR LANE
 $591,900 4 / 2
 1,843sf N / N
8065 PLEASANT PINE CIRCLE
 $590,000 4 / 2
 1,843sf N / N
3131 LOWNDES DRIVE
 $554,000 4 / 2
 2,126sf N / Y
2007 STRATHAVEN ROAD
 $550,000 4 / 2
 1,699sf N / N
2627 AMBERGATE ROAD
 $550,000 4 / 3
 1,805sf N / Y
5255 SEMINOLE AVENUE
 $550,000 4 / 3
 2,170sf N / N
3901 WOODGLADE COVE
 $544,000 4 / 2
 2,213sf N / N
2844 SCARLET ROAD
 $529,900 4 / 2
 1,508sf N / N
TERRACE
 $525,000 4 / 2
 2,075sf N / Y
3231 LOWNDES DRIVE
 $525,000 4 / 2
 1,749sf N / N
1809 PINEVIEW CIRCLE
 $520,000 4 / 2
 1,631sf N / N
2227 COVENTRY DRIVE
 $515,000 4 / 2
 2,076sf N / N
1742 WILLA CIRCLE
 $510,000 4 / 2
 2,313sf N / N
4026 TENITA DRIVE
 $505,000 4 / 2
 2,122sf N / Y
7679 BENT BOW TRAIL
 $499,900 4 / 2
 2,616sf N / N
5338 TANGERINE AVENUE
 $499,900 4 / 2
 2,195sf N / Y
1422 TIERRA CIRCLE
 $499,900 4 / 2
 1,827sf N / Y
1157 VALLEY CREEK RUN
 $498,000 4 / 2
 2,171sf N / N
1921 JAPONICA ROAD
 $485,000 4 / 2
 2,171sf N / N
2886 CAREW AVENUE
 $475,000 4 / 2
 1,766sf N / N
7446 HOUSTON COURT E
 $459,900 4 / 2
 1,795sf N / Y
1354 TIERRA CIRCLE
 $449,900 4 / 2
 1,827sf N / N
1621 PURITAN
 $440,000 4 / 2
 1,765sf Y / Y
2829 ALOMA AVENUE
 $440,000 4 / 2
 1,821sf N / Y
2209 FAIRGLENN WAY
 $439,999 4 / 2
 2,027sf N / N
1985 JAPONICA ROAD
 $434,900 4 / 2
 2,096sf N / Y
1842 PURITAN AVENUE
 $429,900 4 / 2
 1,836sf N / N
770 W WEBSTER AVENUE
 $425,000 4 / 2
 1,008sf N / N
1006 BRADFORD DRIVE
 $419,000 4 / 2
 2,130sf N / Y

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1333 ALBERTA DRIVE
 $5,750,000 3 / 3
 3,738sf Y / Y
922 N PENNSYLVANIA AVENUE
 $2,399,000 3 / 4
 3,440sf N / N
622 PENN PLACE
 $1,950,000 3 / 3
 2,767sf N / N
1640 MAYFIELD AVENUE
 $1,799,000 3 / 2
 2,907sf N / Y
1270 ARLINGTON PLACE
 $1,750,000 3 / 4
 2,964sf N / Y
1741 PALMER AVENUE
 $1,595,000 3 / 3
 2,351sf N / N
1644 HIBISCUS AVENUE
 $1,470,000 3 / 3
 2,145sf N / Y
2525 VENETIAN WAY
 $1,350,000 3 / 2
 1,993sf N / Y
632 COUNTRY CLUB DRIVE
 $1,170,000 3 / 2
 2,342sf Y / Y
1610 CHESTNUT AVENUE
 $1,050,000 3 / 2
 2,140sf N / Y
913 MOSS LANE
 $999,000 3 / 2
 1,887sf N / N
7801 GEORGEANN ST
 $985,000 3 / 2
 3,158sf Y / Y
674 W COMSTOCK AVENUE
 $975,000 3 / 1
 1,045sf N / N
250 CORTLAND AVENUE
 $975,000 3 / 2
 2,114sf N / Y
2823 WRIGHT AVENUE
 $949,900 3 / 2
 1,536sf Y / N
251 GLENRIDGE WAY
 $899,000 3 / 2
 1,314sf N / N
441 N CAPEN AVENUE
 $800,000 3 / 2
 1,745sf N / N
676 DUNBLANE DRIVE
 $799,000 3 / 2
 1,827sf N / Y
625 BRECHIN DRIVE
 $795,000 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
1147 WILDMEADOW RUN
 $710,000 3 / 3
 2,002sf N / N
1399 ALOMA AVENUE
 $675,000 3 / 2
 1,804sf N / N
2612 LAFAYETTE AVENUE
 $674,000 3 / 2
 2,447sf N / N
3006 NORTHWOOD BOULEVARD
 $670,000 3 / 2
 1,729sf N / N
1926 NATALEN ROAD
 $659,900 3 / 2
 1,469sf N / Y
1218 FAIRWAY DRIVE
 $640,000 3 / 2
 1,760sf N / N
236 N RANGER BOULEVARD
 $619,000 3 / 2
 1,844sf N / N
701 DENTON ROAD
 $579,000 3 / 2
 2,268sf N / Y
212 BLOSSOM LANE
 $575,000 3 / 2
 1,771sf N / N
274 N RANGER BOULEVARD
 $565,000 3 / 2
 1,420sf N / Y
720 N PENNSYLVANIA AVENUE
 $550,000 3 / 2
 1,115sf N / N
1116 FAIRWAY DRIVE
 $549,900 3 / 2
 1,738sf N / N
240 CAMBRIDGE BOULEVARD
 $549,000 3 / 2
 1,630sf N / N
2244 BROOKSHIRE AVENUE
 $549,000 3 / 2
 1,464sf N / N
426 S LAKEMONT AVENUE
 $545,000 3 / 2
 1,656sf N / Y
2381 ROXBURY ROAD
 $528,000 3 / 2
 1,645sf N / N
2327 MULBRY DRIVE
 $525,000 3 / 1
 1,191sf N / N
7584 LODGE POLE TRAIL
 $515,000 3 / 2
 1,906sf N / Y
1924 SUMMERFIELD ROAD
 $515,000 3 / 2
 1,492sf N / N
7730 BROKEN ARROW TRAIL
 $514,999 3 / 2
 2,706sf N / Y
1173 VALLEY CREEK RUN
 $499,900 3 / 2
 1,906sf N / N
2835 BONGART ROAD
 $489,000 3 / 3
 1,880sf N / Y
3054 BLUEBROOK DRIVE
 $479,900 3 / 2
 1,939sf N / Y
1564 CAVENDISH ROAD
 $479,000 3 / 1
 1,140sf N / N
1608 BOMI CIRCLE
 $475,000 3 / 2
 1,807sf N / N
2648 AMSDEN ROAD
 $472,000 3 / 2
 1,623sf N / Y
1710 ASTER DRIVE
 $469,000 3 / 2
 1,664sf N / Y
3304 BENNINGTON CT
 $465,000 3 / 2
 1,804sf N / N
2151 CONIFER AVENUE
 $459,900 3 / 2
 1,806sf N / Y
3306 FISHERMANS COVE
 $459,000 3 / 2
 2,408sf N / Y
5001 TANGERINE AVENUE
 $440,000 3 / 2
 1,732sf N / Y
5547 GARDEN GROVE CIRCLE
 $430,000 3 / 2
 1,517sf N / Y
619 BYRON ROAD
 $425,000 3 / 2
 1,349sf N / N
3107 ASH PARK LOOP
 $425,000 3 / 2
 1,518sf N / N
4959 ARDMORE DRIVE
 $425,000 3 / 2
 1,664sf N / Y
920 GLORIOSA AVENUE
 $414,999 3 / 2
 1,540sf N / N
7040 BETTY ST
 $410,000 3 / 2
 1,639sf N / N
1921 TAYLOR AVENUE
 $410,000 3 / 2
 1,322sf N / N
5418 S BRACKEN COURT
 $400,000 3 / 2
 1,301sf N / Y

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2260 HAWICK LANE
 $995,000 2 / 1
 1,374sf N / N
311 CORTLAND AVENUE
 $799,900 2 / 2
 1,382sf N / N
1821 GOODRICH AVENUE
 $575,000 2 / 1
 1,000sf N / N
1339 ORCHID AVENUE
 $575,000 2 / 1
 789sf N / N
3601 MIDIRON DRIVE
 $499,000 2 / 1
 954sf N / N
674 DOUGLAS AVENUE
 $499,000 2 / 1
 1,260sf N / N

Property Location

Community Info

  • Winter Park
  • Price Range:
    $400,000-$10,900,000

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