Winter Park

Community Info

  • Price Range:
    $325,000-$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

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
2914 REEF KNOT PLACE
 $1,725,000 6 / 4 / 2
 4,173sf Y / Y
1445 VIA SANGRO PLACE
 $1,350,000 6 / 5 / 1
 5,021sf N / Y

5 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1571 WOODLAND AVENUE
 $6,000,000 5 / 6 / 2
 7,397sf N / Y
2228 AZALEA PLACE
 $5,600,000 5 / 5 / 1
 5,152sf N / Y
857 BROCK STREET
 $4,650,000 5 / 5 / 1
 4,827sf N / Y
207 E KINGS WAY
 $3,650,000 5 / 4 / 1
 3,719sf N / Y
160 W ROCKWOOD WAY
 $3,395,000 5 / 5 / 1
 4,015sf N / Y
1627 MIZELL AVENUE
 $3,300,000 5 / 5 / 1
 3,421sf N / Y
1761 LEGION DRIVE
 $3,265,000 5 / 5 / 1
 4,924sf N / Y
1821 ENGLEWOOD ROAD
 $3,075,000 5 / 5 / 1
 3,863sf N / Y
1836 WHITEHALL DRIVE
 $2,995,000 5 / 6 / 1
 4,168sf 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
1754 TAYLOR AVENUE
 $2,569,999 5 / 4 / 1
 3,670sf N / Y
1823 SUNSET DRIVE
 $2,549,000 5 / 4 / 1
 3,479sf N / Y
450 LAKEWOOD DRIVE
 $2,500,000 5 / 4 / 2
 4,572sf N / Y
926 ENCLAVE PLACE
 $2,475,000 5 / 4 / 1
 4,150sf N / Y
946 ENCLAVE PLACE
 $2,375,000 5 / 4 / 1
 3,989sf N / Y
938 ENCLAVE PLACE
 $2,300,000 5 / 4 / 1
 3,865sf N / Y
1840 LAUREL ROAD
 $2,299,000 5 / 5
 2,868sf N / Y
930 ENCLAVE PLACE
 $2,275,000 5 / 4 / 1
 3,813sf N / Y
914 ENCLAVE PLACE
 $2,070,000 5 / 4 / 1
 3,617sf N / Y
2260 MULBRY DRIVE
 $1,925,000 5 / 4
 3,246sf N / N
2032 KIMBRACE PLACE
 $1,800,000 5 / 4
 3,382sf 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
1864 GRINNELL TERRACE
 $1,599,000 5 / 3 / 1
 3,028sf N / Y
1526 MILLER AVENUE
 $1,574,900 5 / 4 / 1
 3,252sf N / Y
777 HALIFAX AVENUE
 $1,500,000 5 / 4 / 1
 3,109sf N / N
1523 MILLER AVENUE
 $1,400,000 5 / 4
 3,164sf N / Y
1473 BERKSHIRE AVENUE
 $1,399,000 5 / 4
 2,351sf N / Y
1448 LAKE FLORENCE WAY
 $1,099,900 5 / 4 / 1
 3,652sf N / Y
2702 PARKLAND DRIVE
 $1,049,000 5 / 3
 2,656sf N / N
120 LONGBRANCH ROAD
 $860,000 5 / 3 / 1
 3,284sf N / Y
1927 ELAND AVENUE
 $820,000 5 / 3
 2,242sf N / N
724 MONMOUTH WAY
 $798,000 5 / 3 / 1
 2,832sf N / N
2612 ROXBURY ROAD
 $629,900 5 / 3
 2,472sf N / N
2181 LINDEN ROAD
 $450,000 5 / 3
 1,100sf N / N

4 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
2661 VIA TUSCANY
 $5,999,990 4 / 4 / 1
 3,880sf N / Y
313 SYLVAN DRIVE
 $5,500,000 4 / 4 / 1
 4,775sf Y / Y
231 CHELTON CIRCLE
 $4,950,000 4 / 5 / 2
 5,550sf N / Y
1441 CARDINAL COURT
 $3,995,000 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
541 W CANTON AVENUE
 $2,495,000 4 / 3 / 1
 3,553sf N / Y
525 S LAKEMONT AVENUE
 $1,999,990 4 / 3 / 1
 3,330sf N / Y
922 N PENNSYLVANIA AVENUE
 $1,995,000 4 / 4
 3,440sf N / N
1702 ARBOR PARK DRIVE
 $1,900,000 4 / 3 / 1
 2,950sf N / Y
2343 VERSAILLES AVENUE
 $1,865,000 4 / 3 / 1
 3,307sf N / Y
1550 PALM AVENUE
 $1,829,000 4 / 3 / 1
 2,706sf N / Y
1750 CAROLLEE LANE
 $1,780,000 4 / 3 / 1
 3,249sf N / Y
1840 ANZLE AVENUE
 $1,750,000 4 / 2 / 1
 2,350sf N / Y
2525 LAFAYETTE AVENUE
 $1,749,000 4 / 3 / 1
 2,715sf N / Y
1840 BRYAN AVENUE
 $1,725,000 4 / 3 / 1
 3,727sf N / Y
723 SYMONDS AVENUE
 $1,700,000 4 / 4
 3,065sf N / N
2308 MULBRY DRIVE
 $1,699,000 4 / 3 / 1
 2,530sf N / Y
1903 N PARK AVENUE
 $1,649,000 4 / 4
 2,807sf N / Y
1570 PALMER AVENUE
 $1,640,000 4 / 3 / 1
 3,048sf N / Y
250 KILLARNEY
 $1,600,000 4 / 3 / 1
 2,568sf N / Y
2430 CHANTILLY AVENUE
 $1,598,000 4 / 4
 2,916sf N / Y
446 MELROSE AVENUE
 $1,595,000 4 / 2
 2,640sf N / N
341 E READING WAY
 $1,565,000 4 / 4
 3,723sf N / Y
1581 MAGNOLIA AVE
 $1,425,000 4 / 4
 2,756sf N / N
1546 MILLER AVENUE
 $1,419,900 4 / 3 / 1
 2,984sf N / Y
1751 GOODRICH AVENUE
 $1,380,000 4 / 3 / 1
 2,170sf N / N
1421 CHAPMAN CIRCLE
 $1,377,500 4 / 3 / 1
 3,578sf N / N
1320 ORCHID AVENUE
 $1,350,000 4 / 4
 2,998sf N / N
952 MOSS LANE
 $1,319,950 4 / 2 / 3
 3,474sf N / Y
102 BELL PLACE
 $1,299,000 4 / 3 / 1
 2,459sf N / Y
2015 SUMMERFIELD ROAD
 $1,262,500 4 / 4
 3,024sf N / Y
230 KILLARNEY DRIVE
 $1,250,000 4 / 1
 1,260sf Y / N
1870 STAUNTON AVENUE
 $1,250,000 4 / 3 / 1
 2,525sf N / N
AVENUE
 $1,249,900 4 / 3 / 1
 2,936sf N / N
1404 BORDER DRIVE
 $1,075,000 4 / 4
 2,469sf N / N
616 BRECHIN DRIVE
 $999,000 4 / 4 / 1
 2,638sf N / Y
471 HOLT AVENUE
 $995,999 4 / 3
 2,528sf N / N
2667 COCHISE TRAIL
 $985,000 4 / 3
 2,868sf N / Y
3006 NORTHWOOD BOULEVARD
 $975,000 4 / 3
 2,075sf N / N
Lot #21 KAROLINA AVE
 $918,000 4 / 2 / 1
 2,662sf N / N
1521 HERON WOOD PLACE
 $860,000 4 / 2
 3,950sf N / Y
1090 WILDMEADOW RUN
 $835,000 4 / 3 / 1
 2,589sf N / N
1131 WILDMEADOW RUN
 $825,000 4 / 3 / 1
 2,589sf Y / N
1369 BLUE STEM LANE
 $775,000 4 / 3 / 1
 2,589sf N / N
1562 ARBOR PARK DRIVE
 $775,000 4 / 2 / 1
 1,899sf N / N
2286 MARSH SEDGE LANE
 $770,000 4 / 3
 2,192sf N / N
4039 COOL WATER COURT
 $739,777 4 / 2
 2,124sf N / Y
1418 LONE FEATHER TRAIL
 $729,995 4 / 2 / 1
 2,197sf N / N
1316 BLUE STEM LANE
 $725,000 4 / 2 / 1
 2,196sf Y / N
2260 COLDSTREAM DRIVE
 $699,000 4 / 2
 1,509sf N / N
715 S RANGER BOULEVARD
 $695,000 4 / 3
 2,312sf N / Y
943 FAIRWAY DRIVE
 $689,900 4 / 3
 2,067sf N / N
1122 WILDMEADOW RUN
 $665,000 4 / 2 / 1
 1,770sf N / N
7525 LODGE POLE TRAIL
 $600,000 4 / 2
 1,936sf N / Y
4353 STEED TERRACE
 $599,900 4 / 2
 2,275sf N / Y
2627 AMBERGATE ROAD
 $575,000 4 / 3
 1,745sf N / Y
2641 CARVELL COURT
 $550,000 4 / 2
 2,126sf N / Y
2211 KING RICHARDS COURT
 $549,000 4 / 2
 1,845sf N / Y
2054 EASTBROOK BOULEVARD
 $500,000 4 / 3
 2,031sf N / Y
2008 HOUNDSLAKE DRIVE
 $475,000 4 / 2
 2,250sf N / N
1320 GLADIOLAS DR
 $469,900 4 / 2
 1,624sf N / N
1564 LAWNDALE CIRCLE
 $450,000 4 / 2 / 1
 1,980sf N / N
8433 COMMANDER COVE
 $435,000 4 / 2 / 1
 1,903sf N / N
501 HERITAGE BOULEVARD
 $426,000 4 / 2
 1,376sf N / Y
1842 PURITAN AVENUE
 $419,000 4 / 2
 1,836sf N / N
1401 ASTER COURT
 $414,900 4 / 2
 1,653sf N / N
1849 VIBURNUM LANE
 $399,900 4 / 2
 1,627sf N / N
2512 EASTBROOK BOULEVARD
 $390,000 4 / 2
 1,607sf N / N
885 CARNATION DRIVE
 $368,000 4 / 2
 1,240sf N / Y

3 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
1133 BELLA LAGO COVE
 $2,100,000 3 / 2
 1,765sf Y / N
751 PANSY AVENUE
 $1,950,000 3 / 3 / 1
 2,703sf N / Y
1420 ALOMA AVENUE
 $1,949,500 3 / 3 / 1
 2,422sf Y / N
621 HUNTINGTON AVENUE
 $1,770,000 3 / 3 / 1
 2,399sf N / Y
2207 KINDEL AVENUE
 $1,600,000 3 / 2 / 1
 2,733sf N / N
641 NORTHWOOD CIRCLE
 $1,599,000 3 / 3 / 2
 2,756sf N / Y
462 W LYMAN AVENUE
 $1,595,000 3 / 2 / 1
 1,944sf N / N
1113 VIA DEL MAR
 $1,595,000 3 / 2
 2,012sf Y / N
1841 LAKE SPIER DRIVE
 $1,498,000 3 / 4
 2,467sf Y / N
150 E READING WAY
 $1,449,000 3 / 2 / 1
 2,080sf N / N
720 PANSY AVENUE
 $1,350,000 3 / 4
 2,191sf N / N
1881 LAKE SPIER DRIVE
 $1,350,000 3 / 2
 1,750sf Y / N
1922 HAMMERLIN AVENUE
 $1,300,000 3 / 2 / 1
 1,873sf N / Y
240 KILLARNEY DRIVE
 $1,275,000 3 / 2 / 1
 1,329sf Y / N
1600 S PENNSYLVANIA AVENUE
 $1,150,000 3 / 2
 2,158sf N / Y
1220 HOWELL BRANCH ROAD
 $1,105,000 3 / 2
 1,487sf N / N
2227 HOWARD DRIVE
 $1,100,000 3 / 2 / 1
 2,196sf Y / N
437 N CAPEN AVENUE
 $849,000 3 / 2 / 1
 1,904sf N / N
338 BLUE HERON DRIVE
 $840,000 3 / 3
 2,017sf N / Y
1850 BRYAN AVENUE
 $725,000 3 / 2
 1,563sf N / N
900 CARVER STREET
 $689,000 3 / 3
 1,794sf N / N
860 N DENNING DRIVE
 $674,900 3 / 2 / 1
 1,411sf N / N
1416 BORDER DRIVE
 $660,000 3 / 1
 1,243sf N / N
2758 BANCHORY ROAD
 $639,000 3 / 2 / 1
 1,539sf N / Y
508 BRECHIN DRIVE
 $639,000 3 / 2
 1,783sf N / N
1871 BRYAN AVENUE
 $625,000 3 / 2
 1,232sf N / N
2418 EUSTON ROAD
 $624,444 3 / 2 / 1
 2,228sf N / N
2708 LION HEART ROAD
 $614,500 3 / 2
 1,785sf N / Y
4026 TENITA DRIVE
 $599,000 3 / 2
 2,031sf N / Y
1319 BESSMOR ROAD
 $589,000 3 / 2
 1,126sf N / N
1354 INDIANA AVENUE
 $574,900 3 / 2
 1,269sf N / N
1003 LAKE BELL DRIVE
 $549,900 3 / 2
 1,837sf Y / N
330 ELKHORN COURT
 $544,900 3 / 2
 1,570sf N / N
1741 WESTCHESTER AVENUE
 $529,000 3 / 2
 1,434sf N / N
1660 GLADIOLAS DRIVE
 $519,900 3 / 2
 2,047sf N / N
2231 NAIRN DRIVE
 $499,000 3 / 2
 1,088sf N / N
1652 BERKSHIRE AVENUE
 $499,000 3 / 2
 1,498sf N / N
5316 HALYARD COURT
 $495,000 3 / 2
 1,380sf N / Y
2715 PRINCE JOHN ROAD
 $494,900 3 / 2
 1,565sf N / N
525 OLOLU DRIVE
 $490,900 3 / 3
 1,786sf N / N
2703 TIERRA CIRCLE
 $464,000 3 / 2
 1,737sf N / Y
5331 OAK COURT
 $460,000 3 / 2
 1,263sf N / Y
259 ORANGE TERRACE DRIVE
 $449,900 3 / 2
 1,248sf N / N
2007 CORNELL AVENUE
 $449,000 3 / 2
 1,154sf N / N
2041 JEWELL AVENUE
 $439,900 3 / 1
 1,508sf N / N
950 HANOVER AVENUE
 $439,000 3 / 2
 1,606sf N / N
3740 HAWTHORNE LANE
 $435,000 3 / 2
 1,645sf N / Y
2112 EASTBROOK BOULEVARD
 $429,998 3 / 2
 1,470sf N / N
7384 GRAND AVENUE
 $425,000 3 / 2
 1,162sf N / N
1886 CLEMATIS LANE
 $425,000 3 / 2
 1,238sf N / N
1535 LAWNDALE CIRCLE
 $425,000 3 / 2
 1,676sf N / Y
5409 ALBERT DRIVE
 $420,000 3 / 2
 1,483sf N / Y
1955 ELAND AVENUE
 $410,000 3 / 2
 1,494sf N / N
3440 ALLSTON LANE
 $405,000 3 / 2 / 1
 1,533sf N / N
5503 ALBERT DRIVE
 $399,900 3 / 2
 1,366sf N / N
1092 EASTBROOK BOULEVARD
 $399,000 3 / 2
 1,122sf N / Y
2568 LOTAFUN AVENUE
 $395,000 3 / 2
 1,201sf N / N
2626 AMBERGATE ROAD
 $380,000 3 / 1
 1,143sf N / N
1605 PURITAN AVENUE
 $379,000 3 / 2
 1,285sf N / N
310 GRANADA DRIVE
 $339,900 3 / 2
 1,344sf N / N
3562 BOUGAINVILLEA DRIVE
 $339,000 3 / 2
 1,149sf N / N
7393 GRAND AVENUE
 $325,000 3 / 2
 1,518sf N / N

2 Bedroom Homes

Address Price Bed / Baths Interior Space WF / Pool
560 OLOLU DRIVE
 $899,000 2 / 2
 1,086sf Y / N
1431 PALM AVENUE
 $825,000 2 / 2
 1,540sf N / N
230 STRATHY LANE
 $499,000 2 / 1
 920sf N / N
981 ARAGON AVENUE
 $494,999 2 / 1
 857sf N / N
2824 PRINCE JOHN ROAD
 $475,000 2 / 2
 1,438sf N / N
811 OVERSPIN DRIVE
 $349,000 2 / 1
 749sf N / N

Property Location

Community Info

  • Winter Park
  • Price Range:
    $325,000-$6,900,000

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