255 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $3,850,000

View 690 N New York Ave Winter Park FL
View Details 3 Photos
View 690 N New York Ave Winter Park FL
View 690 N New York Ave Winter Park FL
Listed For 1 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4901

  • Year Built

    2021

  • $/SqFt

    $785

*Photos are not actual and are intended for inspirational purposes. MLS#O5935400. The Hope Group. MFR

Home For Sale $2,050,000

View 1445 Holts Grove Cir Winter Park FL
View Details 66 Photos
View 1445 Holts Grove Cir Winter Park FL
View 1445 Holts Grove Cir Winter Park FL
View 1445 Holts Grove Cir Winter Park FL
Listed For 1 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4622

  • Year Built

    2002

  • $/SqFt

    $443

Windsong, one of Winter Park's most sought after neighborhoods, offers exclusive amenities to their residents including a pontoon boat to enjoy the Winter Park chain of Lakes, two community pools, a splash park, a recreation building & a scenic pier for fishing. MLS#O5936822. Coldwell Banker Realty. MFR

Home For Sale $3,495,000

View 1210 Alberta Dr Winter Park FL
View Details 49 Photos
View 1210 Alberta Dr Winter Park FL
View 1210 Alberta Dr Winter Park FL
View 1210 Alberta Dr Winter Park FL
Listed For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    5449

  • Year Built

    1991

  • $/SqFt

    $641

This is a rare offering call today for a private showing. MLS#O5936507. Premier Sotheby'S Intl. Realty. MFR

Home For Sale $799,000

View 2180 Forrest Rd Winter Park FL
View Details 37 Photos
View 2180 Forrest Rd Winter Park FL
View 2180 Forrest Rd Winter Park FL
View 2180 Forrest Rd Winter Park FL
Listed For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2605

  • Year Built

    1945

  • $/SqFt

    $306

Charmont - Main house is approximately 2393sf, guest apartment is 212sf, for a total of 2605sf. MLS#O5938372. Fannie Hillman & Associates. MFR

Home For Sale $795,000

View Details 22 Photos
Listed For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2347

  • Year Built

    1976

  • $/SqFt

    $338

Temple Heights - This fantastic home is ready for you to move in! ! MLS#O5938229. Prestige Property Shop Llc. MFR

Pended $2,300,000

View Details 27 Photos
Listed For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3046

  • Year Built

    1977

  • $/SqFt

    $755

Virginia Heights - Lowest priced Chain of Lakes property in Winter Park MLS#O5938063. Florida One Real Estate Llc. MFR

Home For Sale $429,900

View Details 48 Photos
Listed For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2155

  • Year Built

    1973

  • $/SqFt

    $199

Golfside - This house is ready for you to make it your own! MLS#O5926812. Bustamante Real Estate Inc. MFR

Pended $2,235,000

View Details 7 Photos
Listed For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4381

  • Year Built

    2018

  • $/SqFt

    $510

Kenilworth Shores - Well landscaped and private yard with lovely outdoor accent lighting. MLS#O5937169. Fannie Hillman & Associates. MFR

Home For Sale $625,000

View Details 25 Photos
Listed For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1925

  • Year Built

    1949

  • $/SqFt

    $324

Killarney Estates - NEW ROOF underway! This home is MOVE-IN ready!! ! MLS#O5937703. Weichert Realtors Hallmark Properties. MFR

Pended $550,000

View Details 47 Photos
Listed For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2247

  • Year Built

    1973

  • $/SqFt

    $244

This neighborhood offers an optional HOA and is ideally located near Rollins College, popular Park Avenue in Winter Park, multiple upscale shopping and dining options, Baldwin Park dog park, Audubon Park Garden District and much more! MLS#O5937478. Keller Williams Advantage Realty. MFR

Pended $299,900

View Details 23 Photos
Listed For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1158

  • Year Built

    1996

  • $/SqFt

    $258

Lawndale - Make this charming home yours today! MLS#O5937094. Joshua Unlimited Inc. MFR

Home For Sale $799,900

View Details 17 Photos
Listed For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2112

  • Year Built

    1947

  • $/SqFt

    $378

Charmont - Ask for our detailed virtual tour and see for yourself RIGHT NOW! MLS#S5049320. Tower Team Realty, Llc. MFR

Pended $599,000

View Details 34 Photos
Listed For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2239

  • Year Built

    1965

  • $/SqFt

    $267

Brookshire Heights - This home won't last long! MLS#O5937314. Coldwell Banker Realty. MFR

Pended $425,000

View Details 34 Photos
Listed For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1993

  • Year Built

    1994

  • $/SqFt

    $213

Lost Creek - Don’t miss this one – schedule your showing TODAY! MLS#O5936923. Keller Williams Winter Park. MFR

Home For Sale $374,900

Reduced By $55,000
View Details 17 Photos
Listed For 6 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    857

  • Year Built

    1956

  • $/SqFt

    $437

Seville Park - Plans available to convert to a 3/2 also included in photos. MLS#O5934215. Keller Williams Winter Park. MFR

Pended $330,000

View Details 1 Photo
Listed For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1671

  • Year Built

    1982

  • $/SqFt

    $197

Cedar Ridge - This home will not last long. MLS#S5049290. The Corcoran Connection Llc. MFR

Home For Sale $330,000

View Details 75 Photos
Listed For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1759

  • Year Built

    1985

  • $/SqFt

    $187

This beautiful corner lot home is ready for a new family to enjoy the awesome location and all the perks it provides. MLS#O5937346. Re/Max Assured. MFR

Pended $300,000

View Details 29 Photos
Listed For 6 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1309

  • Year Built

    1983

  • $/SqFt

    $229

Other updates to include; Roof (2018), HVAC (2018), Septic pumped and new drain field (2021), front yard sod (2021), exterior paint and cedar columns (2018), Gutters (2019) MLS#O5937453. Exp Realty Llc. MFR

Pended $699,500

View Details 24 Photos
*POTENTIAL GREAT VALUE
Listed For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3815

  • Year Built

    1993

  • $/SqFt

    $183

Bear Gully Pointe - Minutes to highways, shopping, Rollins College, Trinity prep and restaurants. MLS#O5936780. One Stop Service Realty Inc. MFR

Pended $439,000

View Details 51 Photos
Listed For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1950

  • Year Built

    1958

  • $/SqFt

    $225

Zoned Winter Park schools and waking distance to Ward Park, Brookshire Elementary and a short ride to Rollins, Park Avenue and much more! Schedule your private viewing TODAY! MLS#O5937103. Fannie Hillman & Associates. MFR

Home For Sale $374,900

View Details 25 Photos
Listed For 7 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1259

  • Year Built

    1926

  • $/SqFt

    $297

Lawndale - Don't miss your opportunity to view this gem and own a Winter Park Address! ! MLS#O5936602. Market Connect Realty Llc. MFR

Pended $359,900

View Details 44 Photos
*POTENTIAL GREAT VALUE
Listed For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2300

  • Year Built

    1971

  • $/SqFt

    $156

Woodcrest - Minutes away from shopping, dining, UCF, Valencia college and HWY 417. Best of all no HOA!! ! MLS#O5937129. Vylla Home. MFR

Pended $248,900

View Details 38 Photos
Listed For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1402

  • Year Built

    1982

  • $/SqFt

    $177

Ceramic tile throughout the home and carpet in bedrooms and part of the living room area. MLS#O5937289. Exp Realty Llc. MFR

Pended $1,995,000

View Details 66 Photos
Listed For 8 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4088

  • Year Built

    1930

  • $/SqFt

    $488

Don't miss your opportunity to own this magnificent home with an amazing location! MLS#O5932396. Coldwell Banker Realty. MFR

Home For Sale $695,000

View Details 35 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2352

  • Year Built

    1969

  • $/SqFt

    $295

Winter Park Heights - Ideally situated near the YMCA, Rollins College, Park Avenue, A-rated schools and more, this home represents Winter Park living at its finest. MLS#O5935275. Premier Sotheby'S Intl. Realty. MFR

Home For Sale $559,000

View Details 1 Photo
Listed For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1925

  • Year Built

    2021

  • $/SqFt

    $290

Glencoe - Conveniently located only a shot drive to Park Ave and everything else that Winter Park has to offer. MLS#O5936816. Nova Real Estate Services Inc. MFR

Pended $268,900

View Details 14 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1397

  • Year Built

    1994

  • $/SqFt

    $192

It also has a community pool for your enjoyment, this lovely home and neighborhood is centrally located near everything you would possibly need . MUST SEE! MLS#S5049210. Transcontinental Realty Group,. MFR

Home For Sale $1,080,000

View Details 36 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3023

  • Year Built

    1957

  • $/SqFt

    $357

Green Oaks - Zoned for Dommerich Elementary, Maitland Middle, Winter Park High. MLS#O5936512. Fannie Hillman & Associates. MFR

Pended $999,000

View Details 45 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3483

  • Year Built

    1957

  • $/SqFt

    $286

All measurements are approximate but main house is 3091sf, guest cottage is 392sf, for a total of 3483sf. MLS#O5936636. Fannie Hillman & Associates. MFR

Pended $525,000

View Details 16 Photos
Listed For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1432

  • Year Built

    1940

  • $/SqFt

    $366

Charming 1940's bungalow just 2 blocks from Park Avenue in Winter Park! MLS#O5936574. Coldwell Banker Realty. MFR

Pended $399,900

View Details 42 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1620

  • Year Built

    1957

  • $/SqFt

    $246

Tanglewood - Do not delay to call for an appointment. MLS#O5936505. Fannie Hillman & Associates. MFR

Home For Sale $235,000

View Details 17 Photos
Listed For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    804

  • Year Built

    1959

  • $/SqFt

    $292

Come to decide for yourself! FHA, VA ok. MLS#O5936703. Elite Real Estate And Property Management. MFR

Pended $545,000

View Details 26 Photos
Listed For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2017

  • Year Built

    1962

  • $/SqFt

    $270

This is the one you have been looking for! A Zenn Properties Home. MLS#O5936344. Sand Dollar Realty Group Inc. MFR

Pended $525,000

View Details 35 Photos
Listed For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2175

  • Year Built

    2008

  • $/SqFt

    $241

Tanglewood - Schedule a private tour today, this home won't last long! MLS#O5936159. Exp Realty Llc. MFR

Home For Sale $1,600,000

View Details 55 Photos
Listed For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4227

  • Year Built

    2003

  • $/SqFt

    $378

Fontainebleau - Extra wide street is quiet and great for bike riding, strollers and walking. MLS#O5935762. Kelly Price & Company Llc. MFR

Pended $1,050,000

View Details 54 Photos
Listed For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2680

  • Year Built

    2019

  • $/SqFt

    $391

Dixie Terrace - Indulge in the Winter Park lifestyle. MLS#O5935945. Keller Williams Classic. MFR

Pended $425,000

View Details 32 Photos
Listed For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1896

  • Year Built

    1967

  • $/SqFt

    $224

Kenilworth Shores - With inventory so low do not miss this opportunity to call this your home! MLS#O5933272. Thomas Lynne Realty Group Llc. MFR

Pended $370,000

View Details 20 Photos
Listed For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1998

  • Year Built

    1986

  • $/SqFt

    $185

Glenmoor - Conveniently located near both Winter Park and Orlando, yet tucked away in a quiet, small community. MLS#O5935497. H. & H. Realty, Inc.. MFR

Pended $329,900

View Details 12 Photos
Listed For 12 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    736

  • Year Built

    1945

  • $/SqFt

    $448

Seville Park - Live in one and have the other pay your mortgage! MLS#U8119329. Jack Keller Inc. MFR

Home For Sale $1,135,000

View Details 41 Photos
Listed For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2714

  • Year Built

    2019

  • $/SqFt

    $418

In a real estate market where good homes are hard to find, this one is an absolute MUST SEE. MLS#O5935754. Kelly Price & Company Llc. MFR

Pended $850,000

View Details 56 Photos
*POTENTIAL GREAT VALUE
Listed For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3768

  • Year Built

    2004

  • $/SqFt

    $225

Fontainebleau - Oversized paver driveway is great for large families and lots of guests. MLS#O5935629. Baldwin Park Realty Llc. MFR

Home For Sale $575,000

View Details 5 Photos
Listed For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1646

  • Year Built

    1980

  • $/SqFt

    $349

Homes within this community seldom come on the market – schedule your showing today. MLS#O5935406. Kelly Price & Company Llc. MFR

Pended $399,000

View Details 43 Photos
Listed For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2002

  • Year Built

    1969

  • $/SqFt

    $199

Winter Woods - This is an absolute must-see property that won’t last long. MLS#O5935555. Premier Sotheby'S Intl. Realty. MFR

Pended $330,000

View Details 26 Photos
Listed For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1570

  • Year Built

    1957

  • $/SqFt

    $210

Tanglewood - This home is sure to move fast! MLS#O5935782. Ameriteam Realty Inc. MFR

Home For Sale $269,000

Reduced By $10,000
View Details 23 Photos
Listed For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1652

  • Year Built

    1960

  • $/SqFt

    $162

Come and make this your new home today! MLS#O5935695. Assist 2 Sell All Sellers & Bu. MFR

Home For Sale $4,500,000

View Details 85 Photos
Listed For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5236

  • Year Built

    2000

  • $/SqFt

    $859

For your picturesque piece of paradise, this remarkable residence embodies luxury living at its finest. MLS#O5933713. Premier Sotheby'S Intl. Realty. MFR

Home For Sale $2,195,000

Reduced By $200,000
View Details 41 Photos
Listed For 14 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4456

  • Year Built

    1999

  • $/SqFt

    $492

Maitland Shores - Call today for your private showing. MLS#O5935243. Creegan Group. MFR

Home For Sale $1,300,000

View Details 29 Photos
Listed For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3707

  • Year Built

    1989

  • $/SqFt

    $350

Sylvan Park - Great location-walking distance to shopping, restaurants, Phelps Park, YMCA, New Wellness Center, Winter Park Schools MLS#O5935506. Fannie Hillman & Associates. MFR

Pended $788,000

View Details 36 Photos
Listed For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2064

  • Year Built

    1957

  • $/SqFt

    $381

Located just steps to Blue Jacket Park and with soooo many conveniences including sought after schools plus local shops & dining at the nearby Audubon Park District & Downtown Baldwin Park. MLS#O5935042. Mainframe Real Estate. MFR

Home For Sale $589,000

View Details 25 Photos
Listed For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1830

  • Year Built

    1952

  • $/SqFt

    $321

Minutes to all of your Winter Park/Baldwin Park favorites and a quick drive downtown or out to the beach...don't let this one get away! MLS#O5935188. Re/Max Town & Country Realty. MFR

Viewing HOMES 1 to 50 of 255

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 407-278-2057 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$413,997
$330,000
73
0.0%
21.9%
72

Apopka
$366,139
$345,000
287
4.9%
10.5%
70

Belle Isle
$602,546
$475,000
28
0.0%
21.4%
45

Casselberry
$325,037
$315,000
75
1.3%
16.0%
75

Celebration
$1,110,405
$822,000
50
2.0%
18.0%
81

Champions Gate
$528,547
$525,000
27
0.0%
7.4%
137

Chuluota
$651,907
$515,000
27
3.7%
7.4%
71

Clermont
$430,264
$361,220
301
3.3%
12.6%
69

Gotha
$457,022
$414,500
18
5.6%
16.7%
154

Groveland
$393,317
$325,000
109
0.9%
19.3%
89

Harmony
$355,035
$334,995
26
3.8%
7.7%
70

Kissimmee
$401,306
$345,000
996
2.9%
12.7%
86

Longwood
$666,243
$399,950
180
2.2%
21.7%
73

Maitland
$719,172
$549,900
62
0.0%
24.2%
56

Minneola
$354,961
$332,500
40
5.0%
5.0%
52

Montverde
$1,075,736
$845,360
38
0.0%
21.1%
152

Ocoee
$344,794
$340,000
133
4.5%
8.3%
73

Orlando
$501,101
$365,000
2025
3.4%
18.5%
72

Oviedo
$469,645
$439,500
144
2.1%
15.3%
55

Poinciana
$252,216
$238,900
331
7.3%
7.9%
99

Reunion
$1,253,188
$769,500
77
1.3%
33.8%
199

Saint Cloud
$418,151
$342,935
388
0.8%
11.6%
93

Sanford
$423,862
$340,495
294
1.7%
19.7%
92

Sorrento
$474,451
$349,900
49
0.0%
14.3%
67

Windermere
$1,540,419
$987,500
238
2.5%
22.7%
114

Winter Garden
$571,057
$499,988
337
0.9%
11.0%
74

Winter Springs
$435,902
$425,000
111
3.6%
16.2%
60

EasyStreet

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