Winter Park

Community Info

  • Price Range:
    $410,000-$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
 $2,750,000 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
 $3,150,000 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
2080 WOOD THRUSH LN
 $1,200,000 6 / 4
 4,277sf 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
1400 ALABAMA DRIVE
 $6,200,000 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
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
1660 PALMER AVENUE
 $4,950,000 5 / 6
 6,406sf N / Y
2161 SHARON ROAD
 $4,650,000 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
 $3,595,000 5 / 6
 4,565sf N / Y
1761 LEGION DRIVE
 $3,499,999 5 / 5
 4,955sf N / Y
473 FLETCHER PLACE
 $3,400,000 5 / 5
 4,296sf N / Y
532 WORTHINGTON DRIVE
 $3,295,000 5 / 5
 3,974sf N / Y
1820 ENGLEWOOD ROAD
 $3,190,000 5 / 5
 4,263sf N / 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
1781 PINE AVENUE
 $2,599,000 5 / 4
 3,882sf 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
1710 ONECO AVENUE
 $2,200,000 5 / 4
 3,174sf 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 / 3
 2,964sf 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
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
2105 FOSGATE DRIVE
 $1,325,000 5 / 4
 3,068sf N / Y
1807 MAGNOLIA AVENUE
 $1,200,000 5 / 3
 2,618sf N / N
2330 WESTMINSTER COURT
 $999,000 5 / 3
 3,296sf N / N
5325 CYPRESS RESERVE PLACE
 $935,000 5 / 3
 3,598sf N / Y
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
5073 LAKE HOWELL ROAD
 $539,500 5 / 2
 2,272sf N / Y
2181 LINDEN ROAD
 $470,000 5 / 3
 1,442sf N / N
3415 N GOLDENROD RD
 $425,000 5 / 3
 1,906sf 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
1760 VIA VENETIA
 $4,995,000 4 / 5
 6,242sf N / Y
1150 VIA SALERNO
 $4,750,000 4 / 5
 3,850sf N / Y
1581 FOREST AVENUE
 $3,975,000 4 / 4
 4,683sf N / Y
1742 TEMPLE DRIVE
 $3,899,000 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
 $2,799,000 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
1752 CHESTNUT AVENUE
 $2,199,999 4 / 4
 3,314sf N / Y
2614 PARKLAND DRIVE
 $2,100,000 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
1660 WALNUT AVENUE
 $1,759,000 4 / 3
 2,172sf N / Y
446 ALBERTA DRIVE
 $1,750,000 4 / 2
 3,263sf N / N
1780 MIZELL AVE.
 $1,695,000 4 / 4
 2,743sf 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
 $1,595,000 4 / 4
 4,000sf Y / N
952 MOSS LANE
 $1,514,950 4 / 2
 3,474sf N / Y
1429 CHAPMAN CIRCLE
 $1,499,000 4 / 4
 3,116sf N / N
2408 LAFAYETTE AVENUE
 $1,490,000 4 / 3
 2,838sf N / Y
2401 LAFAYETTE AVENUE
 $1,470,000 4 / 3
 3,349sf N / N
5236 LAKE HOWELL ROAD
 $1,450,000 4 / 3
 3,710sf N / Y
1420 PALMER AVENUE
 $1,395,000 4 / 3
 2,953sf 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
2922 REEF KNOT PLACE
 $1,349,000 4 / 3
 3,153sf Y / Y
1600 BARCELONA WAY
 $1,299,000 4 / 3
 3,014sf N / 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
4048 GILDER ROSE PLACE
 $1,210,000 4 / 3
 3,321sf N / Y
1341 LYNDALE BOULEVARD
 $1,200,000 4 / 3
 2,388sf N / N
1611 CHESTNUT AVENUE
 $1,195,000 4 / 4
 2,916sf N / N
2890 WILD GINGER COURT
 $1,149,000 4 / 4
 3,408sf 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
4107 GABRIELLA LANE
 $1,000,000 4 / 3
 3,074sf Y / Y
1319 HEAVENLY COVE
 $998,000 4 / 3
 4,088sf Y / N
208 BREWER AVENUE
 $995,000 4 / 3
 2,173sf N / N
210 LAUREL PARK COURT
 $995,000 4 / 3
 2,838sf N / Y
1018 TURNER ROAD
 $900,000 4 / 2
 2,237sf Y / Y
1090 WILDMEADOW RUN
 $875,000 4 / 3
 2,589sf N / N
AVENUE
 $815,000 4 / 3
 2,878sf N / N
770 W WEBSTER AVENUE
 $795,000 4 / 2
 1,008sf N / N
2168 MARSH SEDGE LANE
 $789,000 4 / 3
 2,192sf N / Y
1340 BLUE STEM LANE
 $775,000 4 / 3
 2,587sf N / N
620 DARCEY DR
 $765,000 4 / 2
 2,076sf N / N
744 CORNWALL ROAD
 $750,000 4 / 2
 1,968sf N / N
346 ELKHORN COURT
 $735,000 4 / 2
 1,891sf N / Y
607 DUNBLANE DRIVE
 $729,000 4 / 2
 2,046sf N / N
3759 KINSLEY PLACE
 $689,900 4 / 2
 2,251sf N / Y
3110 HEARTLEAF PLACE
 $658,900 4 / 3
 2,860sf Y / Y
3115 HEARTLEAF PLACE
 $650,000 4 / 3
 2,846sf N / N
1507 GOLFSIDE DRIVE
 $635,000 4 / 2
 2,003sf N / Y
3102 HEARTLEAF PLACE
 $625,827 4 / 3
 2,672sf N / N
7988 PLEASANT PINE CIRCLE
 $624,900 4 / 2
 2,267sf N / N
1875 STAUNTON AVENUE
 $598,000 4 / 2
 2,036sf N / N
8065 PLEASANT PINE CIRCLE
 $580,000 4 / 2
 1,843sf N / N
8162 LAZY BEAR LANE
 $559,900 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
3901 WOODGLADE COVE
 $544,000 4 / 2
 2,213sf N / N
1713 W CHERYL DRIVE
 $540,000 4 / 2
 2,030sf N / Y
2844 SCARLET ROAD
 $525,000 4 / 2
 1,508sf N / N
2227 COVENTRY DRIVE
 $515,000 4 / 2
 2,076sf N / N
1742 WILLA CIRCLE
 $510,000 4 / 2
 2,313sf N / N
TERRACE
 $500,000 4 / 2
 2,075sf N / Y
2920 ABBEY COURT
 $500,000 4 / 3
 2,035sf N / Y
5338 TANGERINE AVENUE
 $489,500 4 / 2
 2,195sf N / Y
1157 VALLEY CREEK RUN
 $480,000 4 / 2
 2,171sf N / N
7679 BENT BOW TRAIL
 $479,900 4 / 2
 2,616sf N / N
2886 CAREW AVENUE
 $475,000 4 / 2
 1,766sf N / N
2464 LOTAFUN AVENUE
 $450,000 4 / 3
 1,804sf N / N
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

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1554 LAKE KNOWLES CIRCLE
 $2,495,000 3 / 3
 3,155sf N / N
922 N PENNSYLVANIA AVENUE
 $2,299,000 3 / 4
 3,440sf N / N
622 PENN PLACE
 $1,895,000 3 / 3
 2,767sf N / N
1270 ARLINGTON PLACE
 $1,750,000 3 / 4
 2,964sf N / Y
1741 PALMER AVENUE
 $1,495,000 3 / 3
 2,351sf N / N
1644 HIBISCUS AVENUE
 $1,449,000 3 / 3
 2,145sf N / Y
800 HAMILTON PLACE COURT
 $1,300,000 3 / 3
 3,363sf N / N
2525 VENETIAN WAY
 $1,249,000 3 / 2
 1,993sf N / Y
632 COUNTRY CLUB DRIVE
 $1,170,000 3 / 2
 2,342sf Y / Y
674 W COMSTOCK AVENUE
 $999,000 3 / 1
 1,045sf N / N
913 MOSS LANE
 $999,000 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
251 GLENRIDGE WAY
 $874,900 3 / 2
 1,314sf N / N
1421 SUNSET DRIVE
 $850,000 3 / 3
 1,672sf N / N
2128 Sycamore Dr
$825,000 3 / 2
 1,760sf N / N
2128 SYCAMORE DRIVE
 $825,000 3 / 2
 1,760sf N / N
2418 WHITEHALL CIRCLE
 $765,000 3 / 2
 2,134sf N / N
625 BRECHIN DRIVE
 $765,000 3 / 2
 1,827sf N / N
726 N PENNSYLVANIA AVENUE
 $750,000 3 / 2
 1,167sf N / N
676 DUNBLANE DRIVE
 $750,000 3 / 2
 1,827sf N / Y
2478 WHITEHALL CIRCLE
 $750,000 3 / 2
 2,256sf N / N
5150 OLD HOWELL BRANCH ROAD
 $749,000 3 / 1
 2,108sf N / N
1037 N VIRGINIA AVENUE
 $699,000 3 / 1
 1,101sf N / N
1620 HOWELL BRANCH ROAD
 $690,000 3 / 4
 1,984sf N / N
1147 WILDMEADOW RUN
 $688,000 3 / 3
 2,002sf N / N
1640 CYPRESS POINT LANE
 $679,900 3 / 2
 1,704sf Y / Y
618 BLAIRSHIRE CIRCLE
 $679,000 3 / 3
 1,876sf N / Y
1399 ALOMA AVENUE
 $675,000 3 / 2
 1,804sf N / N
1926 NATALEN ROAD
 $649,900 3 / 2
 1,469sf N / Y
2758 BANCHORY ROAD
 $649,000 3 / 2
 1,539sf N / Y
2612 LAFAYETTE AVENUE
 $625,000 3 / 2
 2,447sf N / N
236 N RANGER BOULEVARD
 $599,999 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
1123 FAIRWAY DRIVE
 $575,000 3 / 2
 1,772sf N / N
720 N PENNSYLVANIA AVENUE
 $550,000 3 / 2
 1,115sf N / N
426 S LAKEMONT AVENUE
 $539,900 3 / 2
 1,656sf N / Y
240 CAMBRIDGE BOULEVARD
 $535,000 3 / 2
 1,630sf N / N
2381 ROXBURY ROAD
 $528,000 3 / 2
 1,645sf N / N
1116 FAIRWAY DRIVE
 $525,000 3 / 2
 1,738sf N / N
2774 BANCHORY ROAD
 $500,000 3 / 2
 1,560sf N / N
1924 SUMMERFIELD ROAD
 $499,999 3 / 2
 1,492sf N / N
2821 CHANTILLY AVENUE
 $495,000 3 / 2
 1,440sf Y / N
2835 BONGART ROAD
 $489,000 3 / 3
 1,880sf N / Y
1173 VALLEY CREEK RUN
 $484,900 3 / 2
 1,906sf N / N
3054 BLUEBROOK DRIVE
 $479,900 3 / 2
 1,939sf N / Y
7602 LODGE POLE TRAIL
 $475,000 3 / 2
 1,906sf 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
541 LONDON ROAD
 $468,000 3 / 2
 1,899sf N / N
5331 OAK COURT
 $460,000 3 / 2
 1,263sf N / Y
1564 CAVENDISH ROAD
 $459,000 3 / 1
 1,140sf N / N
524 BYRON ROAD
 $450,000 3 / 2
 1,469sf N / N
3107 ASH PARK LOOP
 $425,000 3 / 2
 1,518sf N / N
3425 FERNDELL DRIVE
 $425,000 3 / 2
 1,516sf N / N
5001 TANGERINE AVENUE
 $420,000 3 / 2
 1,732sf N / Y
259 BLOSSOM LANE
 $415,000 3 / 2
 1,354sf N / N
920 GLORIOSA AVENUE
 $414,999 3 / 2
 1,540sf N / N
4959 ARDMORE DRIVE
 $410,000 3 / 2
 1,664sf N / Y
5547 GARDEN GROVE CIRCLE
 $410,000 3 / 2
 1,517sf N / Y

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2260 HAWICK LANE
 $995,000 2 / 1
 1,374sf N / N
734 MARYLAND AVE
 $845,000 2 / 2
 1,250sf N / N
311 CORTLAND AVENUE
 $799,900 2 / 2
 1,382sf N / N
1821 GOODRICH AVENUE
 $575,000 2 / 1
 1,000sf N / N
3601 MIDIRON DRIVE
 $499,000 2 / 1
 954sf N / N

Property Location

Community Info

  • Winter Park
  • Price Range:
    $410,000-$8,500,000

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