Winter Park

Community Info

  • Price Range:
    $299,900-$6,900,000

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

11 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
617 N INTERLACHEN AVENUE
 $4,695,000 11 / 7 / 1
 3,615sf N / N

6 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1260 ALABAMA DRIVE
 $6,900,000 6 / 5 / 2
 6,396sf Y / Y
620 VIRGINIA DRIVE
 $3,890,000 6 / 5
 4,677sf N / Y
1445 VIA SANGRO PLACE
 $1,249,000 6 / 5 / 1
 5,021sf N / Y
2600 EUSTON ROAD
 $630,000 6 / 3
 3,145sf N / N

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
901 GOLFVIEW TERRACE
 $6,795,000 5 / 5 / 1
 5,479sf N / Y
1571 WOODLAND AVENUE
 $6,000,000 5 / 6 / 2
 7,397sf N / Y
1011 MCKEAN CIRCLE
 $6,000,000 5 / 5 / 2
 4,806sf N / Y
698 N NEW YORK AVENUE
 $5,995,000 5 / 5 / 1
 5,096sf N / Y
1200 VIA SALERNO
 $5,995,000 5 / 5 / 1
 5,476sf N / Y
1441 GROVE TERRACE
 $5,950,000 5 / 6
 5,796sf Y / Y
2228 AZALEA PLACE
 $5,600,000 5 / 5 / 1
 5,152sf N / Y
1166 PALMER AVENUE
 $5,500,000 5 / 5 / 2
 5,181sf N / Y
825 PALMER AVENUE
 $5,195,900 5 / 5 / 2
 5,122sf N / Y
1631 HILLCREST AVENUE
 $4,500,000 5 / 5 / 1
 4,754sf N / Y
857 BROCK STREET
 $4,350,000 5 / 5 / 1
 4,827sf N / Y
662 GRANVILLE DRIVE
 $3,495,000 5 / 5 / 1
 4,478sf N / Y
1600 LEGION DRIVE
 $3,495,000 5 / 5 / 1
 4,483sf N / Y
1751 GLENCOE ROAD
 $3,390,000 5 / 5 / 2
 4,520sf N / Y
1761 LEGION DRIVE
 $3,265,000 5 / 5 / 1
 4,949sf N / Y
2823 PARKLAND CIRCLE
 $3,250,000 5 / 6
 4,459sf N / Y
2119 HOWARD DRIVE
 $3,195,000 5 / 5 / 1
 4,139sf N / Y
532 LANGHOLM DRIVE
 $2,990,000 5 / 4 / 1
 4,050sf N / Y
1821 ENGLEWOOD ROAD
 $2,950,000 5 / 5 / 1
 3,863sf N / Y
1773 WALNUT AVENUE
 $2,725,000 5 / 4 / 1
 3,784sf N / Y
648 WORTHINGTON DRIVE
 $2,700,000 5 / 4 / 1
 3,588sf N / Y
1681 WOODLAND AVENUE
 $2,629,000 5 / 4 / 1
 3,682sf N / Y
450 LAKEWOOD DRIVE
 $2,500,000 5 / 4 / 2
 4,572sf N / Y
1760 OAKHURST AVENUE
 $2,500,000 5 / 4 / 1
 3,700sf N / N
1441 PALM AVENUE
 $2,449,000 5 / 4 / 1
 3,391sf N / Y
938 ENCLAVE PLACE
 $2,300,000 5 / 4 / 1
 3,865sf N / Y
930 ENCLAVE PLACE
 $2,275,000 5 / 4 / 1
 3,813sf N / Y
918 ENCLAVE PLACE
 $2,125,000 5 / 4 / 1
 3,713sf N / Y
1355 HIBISCUS AVENUE
 $2,100,000 5 / 5 / 1
 4,155sf N / Y
914 ENCLAVE PLACE
 $2,070,000 5 / 4 / 1
 3,617sf N / Y
240 N PHELPS AVENUE
 $1,999,900 5 / 4 / 1
 2,889sf N / Y
513 DUNRAVEN DRIVE
 $1,950,000 5 / 4 / 1
 3,560sf N / Y
281 BREWER AVENUE
 $1,800,000 5 / 4 / 1
 4,029sf N / Y
2407 LAFAYETTE AVENUE
 $1,625,000 5 / 4 / 1
 3,133sf N / Y
777 HALIFAX AVENUE
 $1,449,000 5 / 4 / 1
 3,109sf N / N
1473 BERKSHIRE AVENUE
 $1,369,000 5 / 4
 2,446sf N / Y
1448 LAKE FLORENCE WAY
 $999,900 5 / 4 / 1
 3,652sf N / Y
2330 WESTMINSTER CT.
 $985,000 5 / 3
 3,296sf N / N
1400 PELICAN BAY TRAIL
 $968,000 5 / 3 / 1
 3,600sf Y / Y
120 LONGBRANCH ROAD
 $860,000 5 / 3 / 1
 3,284sf N / Y
1927 ELAND AVENUE
 $799,000 5 / 3
 2,242sf N / N
8061 PLEASANT PINE CIRCLE
 $750,000 5 / 3 / 1
 3,496sf N / N
1825 CHILEAN LANE
 $450,000 5 / 3
 1,636sf N / Y
2181 LINDEN ROAD
 $419,990 5 / 3
 1,442sf N / N

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2661 VIA TUSCANY
 $5,500,000 4 / 4 / 1
 3,880sf N / Y
231 CHELTON CIRCLE
 $4,500,000 4 / 5 / 2
 5,550sf N / Y
702 VIA BELLA
 $4,090,000 4 / 5 / 1
 3,720sf N / Y
540 N PENNSYLVANIA AVENUE
 $3,950,000 4 / 2
 1,652sf N / N
1441 CARDINAL COURT
 $3,600,000 4 / 5 / 1
 4,066sf N / Y
276 DETMAR DRIVE
 $3,600,000 4 / 5
 4,202sf N / Y
2240 VENETIAN WAY
 $3,500,000 4 / 3 / 1
 4,036sf Y / Y
2622 LAKE HOWELL LANE
 $3,400,000 4 / 3
 3,377sf Y / Y
1742 TEMPLE DRIVE
 $3,395,995 4 / 5
 3,658sf N / Y
1825 WHITEHALL DRIVE
 $3,195,000 4 / 4 / 2
 4,311sf N / Y
1663 N PARK AVENUE
 $2,750,000 4 / 5
 3,640sf N / Y
1803 BARKER DRIVE
 $2,190,000 4 / 3
 3,463sf Y / N
1271 PALMER AVENUE
 $2,125,000 4 / 4 / 1
 2,850sf N / Y
DRIVE
 $2,100,000 4 / 4 / 1
 2,830sf N / Y
555 E LAKE SUE AVENUE
 $2,000,000 4 / 4
 3,776sf N / Y
2007 EDWIN BOULEVARD
 $1,995,000 4 / 3 / 1
 3,314sf N / Y
1951 WINTER PARK ROAD
 $1,949,000 4 / 3 / 1
 3,479sf N / Y
1398 GROVE TERRACE
 $1,949,000 4 / 3 / 1
 3,450sf N / Y
2614 PARKLAND DRIVE
 $1,890,000 4 / 3 / 1
 3,307sf N / Y
2507 LAFAYETTE AVENUE
 $1,850,000 4 / 4 / 2
 2,675sf N / Y
922 N PENNSYLVANIA AVENUE
 $1,795,000 4 / 4
 3,440sf N / N
1840 ANZLE AVENUE
 $1,750,000 4 / 2 / 1
 2,350sf N / Y
2613 LAFAYETTE AVENUE
 $1,699,900 4 / 3 / 1
 2,661sf N / Y
2308 MULBRY DRIVE
 $1,699,000 4 / 3 / 1
 2,530sf N / Y
2343 VERSAILLES AVENUE
 $1,675,000 4 / 3 / 1
 3,307sf N / Y
250 KILLARNEY
 $1,600,000 4 / 3 / 1
 2,568sf N / Y
533 COUNTRY CLUB DRIVE
 $1,599,000 4 / 3 / 1
 2,942sf N / Y
1350 LYNDALE BOULEVARD
 $1,499,000 4 / 3 / 1
 3,478sf N / Y
1570 PALMER AVENUE
 $1,485,000 4 / 3 / 1
 3,048sf N / Y
446 MELROSE AVENUE
 $1,475,000 4 / 2
 2,640sf N / N
1546 MILLER AVENUE
 $1,429,900 4 / 3 / 1
 2,984sf N / Y
1581 MAGNOLIA AVE
 $1,425,000 4 / 4
 2,642sf N / N
2237 WOODCREST DRIVE
 $1,425,000 4 / 4 / 1
 3,563sf N / N
1737 INDIANA AVENUE
 $1,399,900 4 / 3 / 1
 2,984sf N / Y
1751 GOODRICH AVENUE
 $1,380,000 4 / 3 / 1
 2,170sf N / N
1534 MILLER AVENUE
 $1,379,900 4 / 3 / 1
 2,984sf N / Y
1320 ORCHID AVENUE
 $1,350,000 4 / 4
 2,998sf N / N
1939 WOODCREST DRIVE
 $1,349,000 4 / 3 / 1
 2,575sf N / Y
2015 SUMMERFIELD ROAD
 $1,250,000 4 / 4
 2,928sf N / Y
1940 MAGNOLIA AVENUE
 $1,190,000 4 / 3 / 1
 5,519sf N / N
230 KILLARNEY DRIVE
 $1,150,000 4 / 1
 1,260sf Y / N
1824 JESSICA COURT
 $1,149,000 4 / 2 / 1
 2,582sf N / N
1517 HARMON AVENUE
 $1,049,000 4 / 3 / 1
 2,135sf N / N
616 BRECHIN DRIVE
 $999,000 4 / 4 / 1
 2,638sf N / Y
443 BROADVIEW AVENUE
 $999,000 4 / 3
 2,803sf N / N
1404 BORDER DRIVE
 $998,000 4 / 4
 2,469sf N / N
1611 CHESTNUT AVENUE
 $985,000 4 / 4
 2,916sf N / N
471 HOLT AVENUE
 $925,000 4 / 3
 2,528sf N / N
3006 NORTHWOOD BOULEVARD
 $899,000 4 / 3
 2,075sf N / N
618 BLAIRSHIRE CIRCLE
 $875,000 4 / 3
 1,876sf N / Y
2572 FIFESHIRE DRIVE
 $875,000 4 / 2 / 1
 2,578sf N / N
2011 HARMON AVENUE
 $849,900 4 / 3
 2,434sf N / N
1131 WILDMEADOW RUN
 $825,000 4 / 3 / 1
 2,589sf Y / N
1562 ARBOR PARK DRIVE
 $775,000 4 / 2 / 1
 1,899sf N / N
2410 SHERBROOKE ROAD
 $769,000 4 / 2 / 1
 2,141sf N / N
4039 COOL WATER COURT
 $739,777 4 / 2
 2,267sf N / Y
2315 KESTREL PERCH PLACE
 $739,000 4 / 3 / 1
 2,553sf N / N
1287 VERDANT GLADE PLACE
 $735,000 4 / 3 / 1
 3,020sf N / N
1316 BLUE STEM LANE
 $725,000 4 / 2 / 1
 2,196sf Y / N
266 N RANGER BOULEVARD
 $724,900 4 / 3
 1,692sf N / N
1418 LONE FEATHER TRAIL
 $699,500 4 / 2 / 1
 2,197sf N / N
715 S RANGER BOULEVARD
 $695,000 4 / 3
 2,312sf N / Y
2260 COLDSTREAM DRIVE
 $675,000 4 / 2
 1,509sf N / N
1122 WILDMEADOW RUN
 $650,000 4 / 2 / 1
 1,770sf N / N
2322 WOODCREST DRIVE
 $650,000 4 / 2
 1,650sf N / Y
2215 WOODCREST DRIVE
 $637,500 4 / 2
 1,688sf N / Y
4260 BEAR GULLY ROAD
 $585,000 4 / 3 / 1
 2,322sf N / N
2228 KING CHARLES COURT
 $575,000 4 / 3
 2,551sf N / N
2067 POINCIANA ROAD
 $548,000 4 / 2
 2,352sf N / N
2627 AMBERGATE ROAD
 $530,000 4 / 3
 1,745sf N / Y
2641 CARVELL COURT
 $525,000 4 / 2
 2,126sf N / Y
1905 BONANZA CT
 $520,000 4 / 2
 1,774sf N / Y
731 BONGART ROAD
 $519,900 4 / 3
 1,842sf N / Y
1934 TAYLOR AVENUE
 $499,000 4 / 1 / 1
 1,470sf N / N
2217 SUSSEX ROAD
 $479,999 4 / 2
 2,092sf N / Y
3020 NICHOLSON DRIVE
 $470,000 4 / 2
 1,756sf N / Y
2020 LEANNE COURT
 $469,900 4 / 3
 2,088sf N / Y
8433 COMMANDER COVE
 $455,000 4 / 2 / 1
 1,903sf N / N
2008 HOUNDSLAKE DRIVE
 $449,500 4 / 2
 2,250sf N / N
1320 GLADIOLAS DR
 $449,000 4 / 2
 1,624sf N / N
3209 HEARTWOOD AVENUE
 $439,900 4 / 2
 1,627sf N / Y
1564 LAWNDALE CIRCLE
 $424,900 4 / 2 / 1
 1,980sf N / N
501 HERITAGE BOULEVARD
 $419,000 4 / 2
 1,376sf N / Y
1386 CLEMATIS LANE
 $417,000 4 / 3
 1,714sf N / N
603 CARNATION DRIVE
 $399,900 4 / 2
 1,427sf N / Y

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1133 BELLA LAGO COVE
 $1,999,900 3 / 2
 1,765sf Y / N
1113 VIA DEL MAR
 $1,595,000 3 / 2
 2,012sf Y / N
2207 KINDEL AVENUE
 $1,575,000 3 / 2 / 1
 2,733sf N / N
462 W LYMAN AVENUE
 $1,450,000 3 / 2 / 1
 1,944sf N / N
641 NORTHWOOD CIRCLE
 $1,425,000 3 / 3 / 2
 2,756sf N / Y
150 E READING WAY
 $1,349,000 3 / 2 / 1
 2,080sf N / N
720 PANSY AVENUE
 $1,295,000 3 / 4
 2,191sf N / N
120 BROADVIEW AVENUE
 $1,250,000 3 / 2
 1,747sf Y / N
240 KILLARNEY DRIVE
 $1,175,000 3 / 2 / 1
 1,329sf Y / N
1500 HARRIS CIRCLE
 $1,175,000 3 / 3
 2,096sf N / N
531 WORTHINGTON DRIVE
 $1,100,000 3 / 3
 2,626sf N / N
1220 HOWELL BRANCH ROAD
 $950,000 3 / 2
 1,487sf N / N
913 MOSS LANE
 $900,000 3 / 2
 1,887sf N / N
437 N CAPEN AVENUE
 $849,000 3 / 2 / 1
 1,904sf N / N
1507 GOLFSIDE DRIVE
 $849,000 3 / 2
 2,003sf N / Y
338 BLUE HERON DRIVE
 $836,000 3 / 3
 2,017sf N / Y
1621 CHESTNUT AVENUE
 $799,000 3 / 2 / 1
 2,022sf N / N
2345 BROOKSHIRE AVENUE
 $795,000 3 / 3
 2,488sf N / N
1003 GOLFSIDE DRIVE
 $749,900 3 / 3
 2,145sf N / Y
1884 JESSICA COURT
 $699,900 3 / 2
 1,666sf N / Y
1850 BRYAN AVENUE
 $699,000 3 / 2
 1,563sf N / N
900 CARVER STREET
 $659,000 3 / 3
 1,794sf N / N
5303 PINE LILY CIRCLE
 $654,000 3 / 2
 2,265sf N / Y
518 GILBERT ROAD
 $639,000 3 / 2
 1,573sf N / Y
2758 BANCHORY ROAD
 $619,500 3 / 2 / 1
 1,539sf N / Y
4026 TENITA DRIVE
 $599,000 3 / 2
 2,031sf N / Y
508 BRECHIN DRIVE
 $579,000 3 / 2
 1,783sf N / N
112 BELL PLACE
 $575,000 3 / 2
 2,253sf N / N
1003 LAKE BELL DRIVE
 $549,900 3 / 2
 1,837sf Y / N
808 DENSMORE DRIVE
 $509,999 3 / 2
 1,460sf N / Y
330 ELKHORN COURT
 $499,900 3 / 2
 1,570sf N / N
2231 NAIRN DRIVE
 $499,000 3 / 2
 1,088sf N / N
5316 HALYARD COURT
 $495,000 3 / 2
 1,380sf N / Y
351 STARLING ROAD
 $489,900 3 / 1 / 1
 1,979sf N / N
1735 MEADOWGOLD LANE
 $480,000 3 / 2
 1,768sf N / Y
2219 WINTER WOODS BOULEVARD
 $479,999 3 / 2 / 1
 1,776sf N / N
1660 GLADIOLAS DRIVE
 $469,900 3 / 2
 2,047sf N / N
3334 YOUNG STREET
 $459,900 3 / 2
 1,706sf N / N
2885 ROXBURY ROAD
 $450,000 3 / 2
 1,511sf N / N
1660 ORANGE AVENUE
 $449,900 3 / 2
 1,614sf N / N
2703 TIERRA CIRCLE
 $449,000 3 / 2
 1,737sf N / Y
3148 NICHOLSON DRIVE
 $449,000 3 / 2
 1,577sf N / N
5415 N LAKE BURKETT LANE
 $435,000 3 / 2 / 1
 2,027sf N / N
3740 HAWTHORNE LANE
 $430,000 3 / 2
 1,645sf N / Y
2818 AMBERGATE ROAD
 $429,900 3 / 2
 1,398sf N / N
1652 BERKSHIRE AVENUE
 $429,000 3 / 2
 1,498sf N / N
1886 CLEMATIS LANE
 $425,000 3 / 2
 1,238sf N / N
3157 SHADY PINE AVENUE
 $425,000 3 / 2
 1,495sf N / N
712 BAFFIE AVENUE
 $419,900 3 / 1
 1,304sf N / N
1535 LAWNDALE CIRCLE
 $415,000 3 / 2
 1,676sf N / Y
1021 PRINCESS GATE BOULEVARD
 $410,000 3 / 2
 1,318sf N / Y
1935 AZALEA AVENUE
 $410,000 3 / 2
 1,300sf N / N
5409 ALBERT DRIVE
 $400,000 3 / 2
 1,483sf N / Y
5405 JUSTINE WAY
 $399,900 3 / 2
 1,247sf N / Y
5503 ALBERT DRIVE
 $399,900 3 / 2
 1,366sf N / N
2038 PONDEROSA AVENUE
 $399,500 3 / 2
 1,360sf N / N
7786 FOX KNOLL PLACE
 $398,000 3 / 2
 1,301sf N / N
1955 ELAND AVENUE
 $394,900 3 / 2
 1,494sf N / N
7361 GRAND AVENUE
 $385,000 3 / 2
 1,305sf N / N
1830 GLADIOLAS DRIVE
 $375,000 3 / 2
 1,674sf N / N
1605 PURITAN AVENUE
 $374,000 3 / 2
 1,285sf N / N
1840 ASTER DRIVE
 $369,900 3 / 2
 1,666sf N / N
2168 RIDGE DRIVE
 $359,900 3 / 2
 1,208sf N / N
3562 BOUGAINVILLEA DRIVE
 $334,000 3 / 2
 1,149sf N / N
310 GRANADA DRIVE
 $325,000 3 / 2
 1,344sf N / N
7393 GRAND AVENUE
 $325,000 3 / 2
 1,518sf N / N
5080 SEMINOLE AVENUE
 $299,900 3 / 2
 1,078sf N / N

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1411 DEVON ROAD
 $950,000 2 / 2
 1,947sf N / Y
560 OLOLU DRIVE
 $849,000 2 / 2
 1,086sf Y / N
1431 PALM AVENUE
 $799,999 2 / 2
 1,540sf N / N
230 STRATHY LANE
 $499,000 2 / 1
 920sf N / N
981 ARAGON AVENUE
 $474,999 2 / 1
 857sf N / N
2176 CRANDON AVENUE
 $399,000 2 / 1
 959sf N / N
811 OVERSPIN DRIVE
 $395,000 2 / 1
 749sf N / N

Property Location

Community Info

  • Winter Park
  • Price Range:
    $299,900-$6,900,000

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