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Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $475,000

View 1926 E Hampton Cir Winter Park FL
View Details 19 Photos
View 1926 E Hampton Cir Winter Park FL
View 1926 E Hampton Cir Winter Park FL
View 1926 E Hampton Cir Winter Park FL
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1900

  • Year Built

    1971

  • $/SqFt

    $250

Located just minutes from downtown Winter Park, you'll enjoy easy access to the best dining, boutique shops, and parks the area has to offer. MLS#TB8311367. REALNET FLORIDA REAL ESTATE.

Home For Sale $1,190,000

View 1571 Oneco Ave Winter Park FL
View Details 38 Photos
View 1571 Oneco Ave Winter Park FL
View 1571 Oneco Ave Winter Park FL
View 1571 Oneco Ave Winter Park FL
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2510

  • Year Built

    2009

  • $/SqFt

    $474

Lake Knowles Terrace - This charming home won't last so schedule your showing today. MLS#O6250954. KELLY PRICE & COMPANY LLC.

Home For Sale $949,000

View 648 Callahan St Winter Park FL
View Details 38 Photos
View 648 Callahan St Winter Park FL
View 648 Callahan St Winter Park FL
View 648 Callahan St Winter Park FL
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1898

  • Year Built

    1950

  • $/SqFt

    $500

Carver Town - Call today to schedule your private showing and make this dream home yours! MLS#O6250649. MILLENIUM REALTY GROUP.

Home For Sale $575,000

View 2821 Chantilly Ave Winter Park FL
View Details 17 Photos
View 2821 Chantilly Ave Winter Park FL
View 2821 Chantilly Ave Winter Park FL
View 2821 Chantilly Ave Winter Park FL
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1440

  • Year Built

    1959

  • $/SqFt

    $399

Winter Park Manor - Extras include: updated electric panel, 2017 AC, updated plumbing & 24x12 backyard shed. WELCOME HOME! MLS#O6249965. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $384,000

View Details 26 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1301

  • Year Built

    1990

  • $/SqFt

    $295

Bridgewater - This charming home is move in ready! MLS#O6249518. BHHS FLORIDA REALTY.

Home For Sale $5,400,000

View Details 34 Photos
On Market For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5072

  • Year Built

    2008

  • $/SqFt

    $1,065

Maitland Shores - The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School. MLS#O6250411. COMPASS FLORIDA LLC.

Home For Sale $2,399,000

View Details 55 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3399

  • Year Built

    2022

  • $/SqFt

    $706

Winter Park Village - The mature and pristine landscape surrounding this gem accentuates the LUXURIOUS ARCHITECTURAL PERFECTION! MLS#O6250342. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $430,000

View Details 41 Photos
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1627

  • Year Built

    1970

  • $/SqFt

    $264

Don’t miss out on the chance to own this well maintained, move-in ready home that’s waiting for you to make it your own! MLS#O6249959. EXP REALTY LLC.

Home For Sale $425,000

View Details 35 Photos
On Market For 4 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1365

  • Year Built

    1957

  • $/SqFt

    $311

Albert Lee Ridge - Request a floorplan and list of recent updates! MLS#O6249948. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $345,000

View Details 35 Photos
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1078

  • Year Built

    1924

  • $/SqFt

    $320

Don’t miss out on this fantastic home in a highly desirable area! MLS#O6249839. SERHANT.

Home For Sale $9,995,000

View Details 56 Photos
On Market For 7 Days

  • Bedrooms

    6

  • Full Bath(s)

    7

  • Sq. Ft.

    8082

  • Year Built

    2002

  • $/SqFt

    $1,237

Maitland Shores - Schedule a private viewing and experience the ultimate Winter Park lifestyle. MLS#O6249727. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $2,200,000

View Details 50 Photos
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3276

  • Year Built

    1995

  • $/SqFt

    $672

Don't miss your chance to make this exquisite property your own and enjoy the epitome of Florida luxury living. MLS#O6249844. KELLER WILLIAMS WINTER PARK.

Home For Sale $735,000

View Details 48 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1784

  • Year Built

    1964

  • $/SqFt

    $412

Brookshire Heights - Highly sought after schools- Brookshire, Glenridge and walk to Winter Park High School! MLS#O6249747. KELLY PRICE & COMPANY LLC.

Home For Sale $700,000

View Details 28 Photos
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1940

  • Year Built

    1952

  • $/SqFt

    $361

Carver Town - Schedule your private showing today! HVAC - 2017 ROOF - 2021 MLS#O6247628. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,875,000

View Details 58 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2505

  • Year Built

    1940

  • $/SqFt

    $749

Cloister Grove - This exquisite mid-century modern retreat offers the perfect balance of charm, functionality, and modern amenities in an A+ location.

MLS#O6249730. KELLY PRICE & COMPANY LLC.

Home For Sale $695,000

View Details 71 Photos
*POTENTIAL GREAT VALUE
On Market For 7 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2990

  • Year Built

    1991

  • $/SqFt

    $232

In rear it has enclosed screened patio to enjoy outdoors and pond view in the front. MLS#O6249859. RE/MAX INNOVATION.

Home For Sale $494,900

View Details 34 Photos
On Market For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1815

  • Year Built

    1977

  • $/SqFt

    $273

Howell Branch Woods - Prime location, close to ample shoping, dining, UCF, Park Avenu and Orlando International Airport. Move in Ready MLS#O6249661. SAND DOLLAR REALTY GROUP INC.

Home For Sale $360,000

View Details 18 Photos
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1147

  • Year Built

    1977

  • $/SqFt

    $314

Woodcrest - Conveniently near Howell Branch Road and just minutes from shopping, diverse dining options and major freeways, this home offers the ideal blend of comfort and convenience for your lifestyle. MLS#O6244088. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $799,000

Reduced By $26,000
View Details 1 Photo
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2220

  • Year Built

    1956

  • $/SqFt

    $360

Lake Forest Park - City allows up to 4,071 sq feet that includes garage. MLS#O6248856. REALCOM REAL ESTATE SERVICES INC.

Pended $724,900

View Details 42 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1508

  • Year Built

    1955

  • $/SqFt

    $481

Don’t miss your chance to make sweet Suffolk yours. MLS#O6248729. PREMIER SOTHEBY'S INTL. REALTY.

Pended $430,000

View Details 21 Photos
On Market For 9 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    897

  • Year Built

    1958

  • $/SqFt

    $479

Call today to see this property. MLS#O6248955. KARICK PRICE & ASSOCIATES.

Home For Sale $485,000

View Details 29 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2004

  • Year Built

    1969

  • $/SqFt

    $242

Casa Aloma - Enjoy the best of Winter Park in an affordable home where convenient living is guaranteed, allowing you to focus on enjoying the comforts of your dream home. MLS#O6248874. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $625,000

View Details 34 Photos
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1040

  • Year Built

    1959

  • $/SqFt

    $601

Come and see for yourself before its gone! Act Now! MLS#O6248290. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $550,000

View Details 20 Photos
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1334

  • Year Built

    1959

  • $/SqFt

    $412

Surrounded by custom homes, this property offers the perfect opportunity to live comfortably now and build your dream home in the future. MLS#O6248775. EXECUTIVE PROPERTIES.

Home For Sale $495,000

View Details 81 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2018

  • Year Built

    1986

  • $/SqFt

    $245

Hyde Park - Sellers are in process to move out.iT sold As-Is condition. MLS#O6247920. FLORIDA REALTY INVESTMENTS.

Home For Sale $435,000

View Details 15 Photos
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1540

  • Year Built

    1956

  • $/SqFt

    $282

Come take a look before it's gone! MLS#G5088048. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $487,500

View Details 38 Photos
On Market For 15 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1012

  • Year Built

    1952

  • $/SqFt

    $482

Orwin Manor - Located minutes from I4 and within walking distance to Orange Avenues restaurants, shops, and parks this home effortlessly combines convenience and modern charm. MLS#O6248164. SAND DOLLAR REALTY GROUP INC.

Home For Sale $3,892,000

View Details 66 Photos
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4635

  • Year Built

    2001

  • $/SqFt

    $840

Virginia Heights - Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High! MLS#O6246352. STOCKWORTH REALTY GROUP.

Home For Sale $425,000

View Details 30 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1645

  • Year Built

    1980

  • $/SqFt

    $258

Wrenwood Heights - Schedule your private showing today and discover the opportunity to add your signature style to this charming pool home. MLS#O6246287. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $569,900

Reduced By $10,000
View Details 36 Photos
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1689

  • Year Built

    1970

  • $/SqFt

    $337

Winter Woods - It is close to downtown Winter Park, shopping, entertainment and award-winning restaurants, etc. MLS#O6245011. MORRIS WILLIAMS REALTY.

Pended $335,000

View Details 28 Photos
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1848

  • Year Built

    1980

  • $/SqFt

    $181

Schedule your showing today and get moving tomorrow. MLS#TB8309977. HOME EXPERTS REALTY, LLC.

Home For Sale $5,695,000

View Details 97 Photos
On Market For 18 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5264

  • Year Built

    2024

  • $/SqFt

    $1,082

A standing seam metal roof and lush landscaping adds the final aesthetic touch on this FG Schaub masterpiece. MLS#O6239351. CORCORAN PREMIER REALTY.

Home For Sale $745,000

View Details 73 Photos
*POTENTIAL GREAT VALUE
On Market For 19 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3496

  • Year Built

    2015

  • $/SqFt

    $213

Don’t miss the opportunity to make this dream home yours! MLS#O6246849. KELLER WILLIAMS ADVANTAGE REALTY.

Pended $675,000

View Details 36 Photos
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1930

  • Year Built

    1979

  • $/SqFt

    $350

Greenview Winter Pines - You won't want to miss this charming house or the chance to live in this beautiful, established neighborhood. ROOF - 2021. MLS#O6245640. ABSOLUTE REALTY GROUP, LLC.

Home For Sale $450,000

View Details 45 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1456

  • Year Built

    1973

  • $/SqFt

    $309

Location is everything with this home being minutes away from Downtown Winter Park, shopping, dining areas, University of Central Florida, and HWY 417. Schedule your private showing today! MLS#O6247560. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $375,000

View Details 21 Photos
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1152

  • Year Built

    1961

  • $/SqFt

    $326

Live, work & play in close proximity to everything you need - call today to schedule a tour! MLS#O6245383. WEMERT GROUP REALTY LLC.

Home For Sale $7,000,000

View Details 100 Photos
*POTENTIAL GREAT VALUE
On Market For 20 Days

  • Bedrooms

    7

  • Full Bath(s)

    5

  • Sq. Ft.

    6540

  • Year Built

    1989

  • $/SqFt

    $1,070

This is truly a remarkable "one of a kind" offering in the enchanting town of Winter Park, Florida. Schedule your private tour today? MLS#O6247174. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $624,900

Reduced By $19,100
View Details 45 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2040

  • Year Built

    1972

  • $/SqFt

    $306

Don’t miss out on this exceptional property! MLS#O6246791. COLDWELL BANKER REALTY.

Home For Sale $509,900

View Details 31 Photos
On Market For 20 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1664

  • Year Built

    1979

  • $/SqFt

    $306

Garden Lake Estates - Highly desirable area with easy access to shopping & main roads. MLS#O6246271. FOLIO REALTY LLC.

Home For Sale $412,000

View Details 38 Photos
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1554

  • Year Built

    1959

  • $/SqFt

    $265

Don’t miss out on the chance to own this fully renovated gem that’s move-in ready and waiting for you to make it your own! MLS#O6244737. REAL BROKER, LLC.

Home For Sale $409,999

View Details 27 Photos
On Market For 20 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    864

  • Year Built

    1949

  • $/SqFt

    $475

Golfview - HVAC: Replaced in 2014 and outdoor unit is rebuilt in 2023 (new compressor) PLUMBING Completely re plumbed in 2009 ROOF- Replaced in 2019 ELECTRICAL replaced in 2009/ Main panel upgraded in 2017 Back Porch built in 2019/ Front Windows replaced in 2018 Exterior Completely repainted: Sept. 2024 MLS#O6246133. LIFESTYLE INTERNATIONAL REALTY.

Home For Sale $1,275,000

View Details 23 Photos
On Market For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2458

  • Year Built

    1978

  • $/SqFt

    $519

Being sold AS IS, please see Realtor Remarks for comments. MLS#O6245474. FANNIE HILLMAN & ASSOCIATES.

Pended $749,000

View Details 50 Photos
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1243

  • Year Built

    1955

  • $/SqFt

    $603

MLS#O6245884. KELLY PRICE & COMPANY LLC.

Home For Sale $1,695,000

View Details 98 Photos
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3055

  • Year Built

    2023

  • $/SqFt

    $555

Winter Park Village - Don’t miss your chance to own this extraordinary property! MLS#O6244257. FLORIDA REALTY INVESTMENTS.

Home For Sale $470,000

View Details 33 Photos
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1928

  • Year Built

    1989

  • $/SqFt

    $244

Schedule your Showing today or click Virtual Tour link to view a video tour. MLS#S5113221. MULTI CHOICE REALTY LLC.

Home For Sale $449,900

Reduced By $10,000
View Details 35 Photos
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1785

  • Year Built

    1965

  • $/SqFt

    $252

Georgetown Estates - In addition to a pool, the spacious backyard includes a shed with electricity; and a porch swing. Sold As-Is MLS#TB8308501. COMMUNITY REALTY ASSOCIATES.

Pended $860,000

View Details 56 Photos
On Market For 25 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1700

  • Year Built

    1935

  • $/SqFt

    $506

This home is a true gem. MLS#O6245627. KELLER WILLIAMS WINTER PARK.

Home For Sale $625,000

View Details 65 Photos
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1369

  • Year Built

    1957

  • $/SqFt

    $457

Kenilworth Shores - Home has been and should be about your Family gatherings as it will accommodate them Perfectly !!!!!!!!!!!!!!!!!!!!!!!!!!!!!! ! MLS#O6245119. FRANK G CANTY REALTY.

Home For Sale $815,000

View Details 36 Photos
On Market For 26 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1979

  • $/SqFt

    $437

Greenview Winter Pines - Don't miss this opportunity to own a truly exceptional property. Schedule your private tour today! MLS#O6244963. CREEGAN GROUP.

Pended $380,000

View Details 39 Photos
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1489

  • Year Built

    1991

  • $/SqFt

    $255

Bridgewater - Located in a prime school district and close to shopping areas, outdoor recreation activities, restaurants, and highway access, this pool home is a gem just waiting for your personal touches. MLS#O6245268. BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Viewing HOMES 1 to 50 of 247

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-967-1435 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$590,250
$459,000
116
0.0%
53.4%
91

Apopka
$514,300
$475,500
567
1.1%
44.3%
75

Belle Isle
$696,375
$537,000
25
0.0%
64.0%
73

Casselberry
$425,743
$399,000
72
4.2%
54.2%
72

Celebration
$1,265,821
$1,074,500
52
0.0%
44.2%
115

Champions Gate
$649,247
$699,000
27
0.0%
55.6%
188

Chuluota
$742,374
$550,000
35
0.0%
57.1%
66

Clermont
$571,357
$499,970
664
0.3%
53.5%
80

Gotha
$1,153,889
$731,000
20
0.0%
40.0%
63

Groveland
$485,493
$409,900
197
1.0%
54.8%
81

Harmony
$436,947
$419,900
57
0.0%
42.1%
95

Kissimmee
$510,068
$440,990
2121
1.4%
50.2%
100

Longwood
$749,849
$580,000
192
1.0%
60.9%
82

Maitland
$886,618
$725,450
82
0.0%
54.9%
86

Minneola
$569,945
$535,108
146
0.0%
28.8%
92

Montverde
$1,469,261
$1,088,870
78
0.0%
47.4%
127

Ocoee
$548,512
$501,950
170
1.2%
48.2%
71

Orlando
$659,703
$485,000
2503
1.4%
48.3%
78

Oviedo
$721,137
$630,000
191
1.0%
55.5%
73

Poinciana
$336,843
$324,990
285
1.1%
57.5%
140

Reunion
$1,660,601
$1,225,000
86
3.5%
44.2%
135

Saint Cloud
$535,078
$458,990
1015
0.3%
52.3%
90

Sanford
$514,671
$409,945
412
1.0%
51.5%
82

Sorrento
$580,710
$439,240
112
0.9%
43.8%
70

Windermere
$2,103,286
$1,250,000
243
0.4%
47.7%
103

Winter Garden
$815,443
$697,900
593
0.3%
46.7%
91

Winter Springs
$555,595
$462,500
136
0.7%
55.9%
68

EasyStreet

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