158 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $6,025,000

View 231 Chelton Cir Winter Park FL
View Details 90 Photos
View 231 Chelton Cir Winter Park FL
View 231 Chelton Cir Winter Park FL
View 231 Chelton Cir Winter Park FL
Listed For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5754

  • Year Built

    2018

  • $/SqFt

    $1,047

This lovely 4 years new-home is available to start living the Winter Park Lifestyle! ! MLS#O5999333. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $699,000

View 3136 Heartleaf Pl Winter Park FL
View Details 42 Photos
View 3136 Heartleaf Pl Winter Park FL
View 3136 Heartleaf Pl Winter Park FL
View 3136 Heartleaf Pl Winter Park FL
Listed For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2891

  • Year Built

    1995

  • $/SqFt

    $242

Lost Creek - Cathedral ceilings. Complete with pool skimmer. MLS#O5998962. MAINFRAME REAL ESTATE.

Home For Sale $499,900

View 820 W Canton Ave Winter Park FL
View Details 23 Photos
View 820 W Canton Ave Winter Park FL
View 820 W Canton Ave Winter Park FL
View 820 W Canton Ave Winter Park FL
Listed For 2 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    952

  • Year Built

    1960

  • $/SqFt

    $525

Call today to schedule a showing, as this opportunity won't last long! MLS#O5999352. KELLY PRICE & COMPANY LLC.

Home For Sale $369,000

View 7045 Hammock Way Winter Park FL
View Details 39 Photos
View 7045 Hammock Way Winter Park FL
View 7045 Hammock Way Winter Park FL
View 7045 Hammock Way Winter Park FL
Listed For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1577

  • Year Built

    1978

  • $/SqFt

    $234

Wrenwood Heights - Schedule your showing today to make this house your home. MLS#O5999581. ELEGANT REALTY LLC.

Home For Sale $531,000

View Details 17 Photos
Listed For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1457

  • Year Built

    1962

  • $/SqFt

    $364

Brookshire Heights - This Winter Park home has one story. MLS#O5999143. OPENDOOR BROKERAGE LLC.

Home For Sale $525,000

View Details 27 Photos
Listed For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1616

  • Year Built

    1956

  • $/SqFt

    $325

Kenilworth Shores - This Winter Park one-story home offers quartz countertops. MLS#O5999132. OPENDOOR BROKERAGE LLC.

Pended $499,900

View Details 1 Photo
Listed For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1994

  • Year Built

    1959

  • $/SqFt

    $251

4/3 pool home located within walking distance to Lake Baldwin. MLS#O5999392. FANNIE HILLMAN & ASSOCIATES.

Pended $3,250,000

View Details 10 Photos
*POTENTIAL GREAT VALUE
Listed For 4 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    4711

  • Year Built

    2022

  • $/SqFt

    $690

Sicilian Shores - This magnificent home is located in the heart of Winter Park’s prestigious Via streets and is a short stroll away from Lake Maitland, the Winter Park Racquet Club and Kraft Azalea Gardens. MLS#O5998918. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,749,000

View Details 22 Photos
Listed For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1552

  • Year Built

    1960

  • $/SqFt

    $1,127

Please note the value is in the land, potential purchasers should consider the existing home as a tear down. MLS#O5998797. COLDWELL BANKER REALTY.

Pended $390,000

View Details 6 Photos
Listed For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1349

  • Year Built

    1940

  • $/SqFt

    $289

This R-2 zoned home is nested right in the heart of Winter Park and is just walking distance to Park Avenue, Winter Park’s Historic area, Hannibal Square and plenty of upscale shopping and dining. MLS#O5998723. FUSILIER MANAGEMENT GROUP.

Pended $370,000

View Details 18 Photos
Listed For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1346

  • Year Built

    1985

  • $/SqFt

    $275

Garden Grove - This Beautiful home won't last long, so call now and book your private showing today. HIGHEST and BEST MLS#V4922777. LA ROSA REALTY CW PROPERTIES L.

Home For Sale $1,125,000

View Details 4 Photos
Listed For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2700

  • Year Built

    2022

  • $/SqFt

    $417

Because the home is a spec on paper, all is subject to change. MLS#O5996896. COLONY REALTY GROUP, INC..

Pended $1,069,000

View Details 41 Photos
Listed For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2714

  • Year Built

    2019

  • $/SqFt

    $394

Homes like this don't come around every day, so don't miss your opportunity to own this one! MLS#O5998550. KELLY PRICE & COMPANY LLC.

Pended $450,000

View Details 27 Photos
Listed For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1480

  • Year Built

    1956

  • $/SqFt

    $304

Kenilworth Shores - Zoned for Brookshire Elementary, Glenridge Middle and Winter Park High School. MLS#O5998131. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $320,000

View Details 31 Photos
*POTENTIAL GREAT VALUE
Listed For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1576

  • Year Built

    1958

  • $/SqFt

    $203

Call today for your private showing! MLS#O5997412. MAINFRAME REAL ESTATE.

Pended $649,900

View Details 43 Photos
Listed For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2327

  • Year Built

    1968

  • $/SqFt

    $279

Do not miss this opportunity to call this convenient area home close to Shopping, Restaurants, all major Highways, Winter Park Hospital, The Winter Park Pines Golf Course, The Cady Way Trail & Winter Park’s renowned Park Ave. Zoned for Winter Park schools, this Remarkable Property will not last–Schedule your Private Showing Today! MLS#O5998154. FANNIE HILLMAN & ASSOCIATES.

Pended $475,000

View Details 26 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1608

  • Year Built

    1963

  • $/SqFt

    $295

Winter Park Pines - This is a highly sought-after location, don't miss your chance! Schedule your showing today! MLS#O5997266. REALTY HOME PARTNERS LLC.

Pended $415,000

View Details 48 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2124

  • Year Built

    1983

  • $/SqFt

    $195

Garden Lake Estates - Located just a short drive to shops, restaurants and all major roadways, you won’t be disappointed! MLS#O5998038. MAINFRAME REAL ESTATE.

Pended $330,000

View Details 34 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1650

  • Year Built

    1969

  • $/SqFt

    $200

Casa Aloma - Located 5 minutes from Full Sail University, 10 minutes from Rollins College and Baldwin Park. MLS#O5998004. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $1,800,000

View Details 47 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3609

  • Year Built

    1935

  • $/SqFt

    $499

Osceola Shores - Zoned for Brookshire Lakemont Elementary, Maitland Middle, and Winter Park High School. MLS#O5996629. KELLY PRICE & COMPANY LLC.

Pended $1,550,000

View Details 31 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3672

  • Year Built

    2016

  • $/SqFt

    $422

Campo Bello - PLEASE SEND HIGHEST AND BEST OFFER BY 5:00pm Saturday 1/22/22 MLS#O5997528. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $649,900

View Details 46 Photos
*POTENTIAL GREAT VALUE
Listed For 9 Days

  • Bedrooms

    6

  • Full Bath(s)

    3

  • Sq. Ft.

    3145

  • Year Built

    1951

  • $/SqFt

    $207

Glencoe - You’ll love this fabulous Winter Park location, it’s less than five minutes to jump on I-4, less than 10 minutes to Winter Park Village and all the shops and restaurants, less than 15 minutes to downtown Orlando, about 25 minutes to Walt Disney World and about an hour to the beaches. NO HOA! MLS#O5997913. WATSON REALTY CORP.

Pended $429,000

View Details 19 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1628

  • Year Built

    1963

  • $/SqFt

    $264

Winter Park Estates - Close to downtown Winter Park and 436 for easy access to 417, UCF, Full Sail or the airport MLS#O5997456. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $405,000

View Details 17 Photos
Listed For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1191

  • Year Built

    1984

  • $/SqFt

    $340

Oakcrest - Hurry, this won’t last long! MLS#O5997575. OPENDOOR BROKERAGE LLC.

Home For Sale $339,000

View Details 25 Photos
Listed For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1647

  • Year Built

    1980

  • $/SqFt

    $206

Garden Lake Estates - Call me to schedule your showing before it’s GONE! MLS#O5992866. ERA GRIZZARD REAL ESTATE.

Home For Sale $1,250,000

View Details 40 Photos
Listed For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3400

  • Year Built

    1995

  • $/SqFt

    $368

Call and schedule your private showing today! MLS#O5997225. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $1,200,000

View Details 23 Photos
Listed For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3154

  • Year Built

    2016

  • $/SqFt

    $380

***Some photos have been VIRTUALLY STAGED*** MLS#O5997174. VONAC REALTY INC.

Pended $557,000

View Details 35 Photos
Listed For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1854

  • Year Built

    1965

  • $/SqFt

    $300

This home is centrally located near Cady Way Trail, Winter Park Pines Golf Course, Cady Way Pool, two public parks, tennis courts, Advent Health Hospital, Crosby Wellsness Center, minutes to desired fine dining and shopping on Park Avenue, The Farmer's Market, Baldwin Park Dog Park and The Baldwin Park Community, as well as, public transportation with easy access to all major highways including I-4 and the 417...Welcome Home! ! MLS#O5997140. GRACE REALTY, INC..

Home For Sale $459,999

View Details 27 Photos
Listed For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1696

  • Year Built

    1961

  • $/SqFt

    $271

This home has great schools, near transportation; 417, 408, shopping, entertainment, and around the corner from the Seminole Trail. MLS#O5997157. 407 PROPERTIES.

Home For Sale $1,999,999

View Details 4 Photos
Listed For 14 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4500

  • Year Built

    2022

  • $/SqFt

    $444

Winter Park Village - The fully landscaped backyard offers plenty of privacy to enjoy the terrace, a built-in summer kitchen and lovely pool. MLS#O5996920. PREMIER SOTHEBY'S INTL. REALTY.

Pended $475,000

View Details 17 Photos
Listed For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1291

  • Year Built

    1987

  • $/SqFt

    $368

Parklando - Ideally located just a few minutes from East End Market as well as the other fun shops and restaurants along Corrine Drive! MLS#O5996893. FANNIE HILLMAN & ASSOCIATES.

Pended $349,900

View Details 16 Photos
Listed For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1285

  • Year Built

    1955

  • $/SqFt

    $272

Fairbanks Shores - No HOA, so bring your toys. MLS#O5996687. MAINFRAME REAL ESTATE.

Pended $699,000

View Details 27 Photos
Listed For 15 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1586

  • Year Built

    1969

  • $/SqFt

    $441

Sylvan Lake Shores - This home is truly a gem - call today to schedule your showing! MLS#O5996497. CORCORAN PREMIER REALTY.

Pended $340,000

View Details 22 Photos
Listed For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1520

  • Year Built

    1954

  • $/SqFt

    $224

Temple Terrace - Priced right and Easy to show! MLS#O5996491. STOCKWORTH REALTY GROUP.

Pended $589,900

View Details 41 Photos
Listed For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1968

  • Year Built

    1966

  • $/SqFt

    $300

Winter Park Pines - Centrally located in a top-rated Winter Park schools and is just minutes from all the amazing restaurants, shops, and entertainment on Park Avenue in Winter Park. MLS#O5996316. HOME PRO REALTY CORP..

Pended $425,000

View Details 37 Photos
Listed For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1550

  • Year Built

    1962

  • $/SqFt

    $274

HVAC: 2013, Roof: 1.5 years old MLS#O5995667. KELLER WILLIAMS WINTER PARK.

Pended $400,000

View Details 25 Photos
Listed For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1614

  • Year Built

    1971

  • $/SqFt

    $248

Winter Park Estates - The seller also had the pool deck resurfaced in 2019, a new roof in 2014, and the flat roof resealed in 2021. MLS#O5994339. CENTURY 21 ONEBLUE.

Pended $399,999

View Details 51 Photos
Listed For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1645

  • Year Built

    1982

  • $/SqFt

    $243

Garden Lake Estates - This is the home you have been waiting for. MLS#O5996301. FERN C BURR LLC.

Pended $365,000

View Details 34 Photos
Listed For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1508

  • Year Built

    1976

  • $/SqFt

    $242

Howell Estates - The attached garage is very spacious with room for your tools and toys, all located just minutes from 436 or the 417 to the east. Come see this one quickly! MLS#O5993942. KELLER WILLIAMS HERITAGE REALTY.

Pended $390,300

View Details 33 Photos
Listed For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1560

  • Year Built

    1980

  • $/SqFt

    $250

Wrenwood Heights - Minutes away from both Costco and the Publix Shopping Center. MLS#O5995959. EXP REALTY LLC.

Pended $455,000

View Details 30 Photos
Listed For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1551

  • Year Built

    1963

  • $/SqFt

    $293

Brookshire Heights - Call today for your private tour. MLS#O5995555. CREEGAN GROUP.

Home For Sale $430,000

View Details 20 Photos
Listed For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1557

  • Year Built

    1960

  • $/SqFt

    $276

Neutral interior paint color. Oversized lighted carport. MLS#O5994983. LEGACY CORNERSTONE INC.

Home For Sale $382,000

View Details 23 Photos
Listed For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1378

  • Year Built

    1961

  • $/SqFt

    $277

Temple Terrace - This Winter Park one-story home offers an in-ground pool, and granite countertops. MLS#O5995713. OPENDOOR BROKERAGE LLC.

Pended $499,000

View Details 38 Photos
Listed For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1942

  • Year Built

    1969

  • $/SqFt

    $257

Close to Full Sail University, Rollins College, The Cady Way Trail and all the fun that Winter Park has to offer. Welcome Home! MLS#O5995310. RE/MAX 200 REALTY.

Home For Sale $799,000

View Details 45 Photos
Listed For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2607

  • Year Built

    1985

  • $/SqFt

    $306

Conveniently located near Winter Park shops, Baldwin Park, Winter Park hospital and downtown Orlando. MLS#O5994835. FANNIE HILLMAN & ASSOCIATES.

Pended $329,900

View Details 26 Photos
Listed For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1376

  • Year Built

    1970

  • $/SqFt

    $240

Woodcrest - All fans and lights are new, as well as new flooring throughout the home! Come see this home today! MLS#O5995444. ENGEL & VOELKERS ORLANDO.

Home For Sale $1,150,000

View Details 6 Photos
Listed For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2830

  • Year Built

  • $/SqFt

    $406

Because the home is a spec on paper, all is subject to change. MLS#O5994313. COLONY REALTY GROUP, INC..

Pended $1,050,000

View Details 33 Photos
Listed For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2451

  • Year Built

    2003

  • $/SqFt

    $428

Sylvan Lake Shores - Location is just minutes to Park Avenue’s shopping and restaurants, the Farmers’ Market, Central Park’s many festive events, Rollins College, Sun Rail, Golf, top rated schools, health services and Winter Park’s pristine chain of lakes. MLS#O5991616. COLDWELL BANKER REALTY.

Home For Sale $639,900

Reduced By $10,000
View Details 43 Photos
Listed For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1940

  • Year Built

    1952

  • $/SqFt

    $330

Carver Town - This is a wonderful opportunity for a "move-in-ready" home in a prime location with all that Winter Park has to offer, click on the virtual tour link for a personalized experienced and schedule your private showing today! MLS#O5994982. KELLER WILLIAMS ADVANTAGE III.

Home For Sale $570,000

View Details 18 Photos
Listed For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1899

  • Year Built

    1970

  • $/SqFt

    $300

Conwill Estates - Can build between 3200 and 3400 SF. See Floor plans in Photos MLS#O5991865. COLEDEV REAL ESTATE LLC.

Viewing HOMES 1 to 50 of 158

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
$443,926
$389,000
69
0.0%
29.0%
68

Apopka
$437,979
$416,990
249
2.8%
18.5%
76

Belle Isle
$544,994
$485,000
17
11.8%
35.3%
56

Casselberry
$370,739
$377,450
58
1.7%
22.4%
48

Celebration
$1,326,848
$949,000
45
0.0%
8.9%
88

Champions Gate
$563,114
$544,995
14
0.0%
28.6%
109

Chuluota
$786,792
$474,500
13
0.0%
23.1%
93

Clermont
$489,068
$430,083
344
0.9%
10.2%
70

Gotha
$604,311
$485,000
9
0.0%
22.2%
194

Groveland
$444,089
$386,700
135
0.7%
16.3%
92

Harmony
$428,343
$380,490
30
0.0%
3.3%
56

Kissimmee
$469,551
$393,990
911
1.3%
11.3%
67

Longwood
$585,229
$434,950
136
1.5%
29.4%
62

Maitland
$581,479
$525,000
38
0.0%
42.1%
79

Minneola
$459,132
$442,968
68
0.0%
14.7%
72

Montverde
$1,427,543
$975,000
35
0.0%
11.4%
123

Ocoee
$429,657
$425,000
75
0.0%
25.3%
60

Orlando
$544,590
$389,900
1561
2.4%
18.4%
73

Oviedo
$627,958
$550,000
88
1.1%
23.9%
57

Poinciana
$305,895
$289,990
306
0.0%
7.5%
114

Reunion
$1,593,790
$1,208,450
70
0.0%
8.6%
105

Saint Cloud
$467,061
$399,900
468
1.3%
11.1%
77

Sanford
$427,896
$371,495
208
2.9%
18.8%
81

Sorrento
$622,843
$649,900
35
2.9%
14.3%
69

Windermere
$1,480,117
$914,000
113
2.7%
16.8%
103

Winter Garden
$697,596
$599,500
249
0.0%
12.4%
72

Winter Springs
$468,291
$425,000
76
2.6%
18.4%
43

EasyStreet

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