196 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $2,325,000

View 1300 Raintree Pl Winter Park FL
View Details 54 Photos
View 1300 Raintree Pl Winter Park FL
View 1300 Raintree Pl Winter Park FL
View 1300 Raintree Pl Winter Park FL
Listed For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4295

  • Year Built

    2004

  • $/SqFt

    $541

Camwood - Immaculately cared for with updates that are ready for you to enjoy! MLS#O6026944. KELLER WILLIAMS WINTER PARK.

Home For Sale $975,000

View 5008 Lake Howell Rd Winter Park FL
View Details 41 Photos
View 5008 Lake Howell Rd Winter Park FL
View 5008 Lake Howell Rd Winter Park FL
View 5008 Lake Howell Rd Winter Park FL
*POTENTIAL GREAT VALUE
Listed For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2710

  • Year Built

    1954

  • $/SqFt

    $360

Tanglewood - Nearby recreation includes the Interlachen Country Club, Winter Park YMCA and the Cady Way Trail. MLS#O6024132. COLDWELL BANKER REALTY.

Home For Sale $805,000

View 27 Stymie Pl Winter Park FL
View Details 3 Photos
View 27 Stymie Pl Winter Park FL
View 27 Stymie Pl Winter Park FL
Listed For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2327

  • Year Built

    2022

  • $/SqFt

    $346

Golfview - Contact our new homes specialist for more information on this specific home or to schedule an appointment. MLS#O6023632. DOMAIN REALTY LLC.

Home For Sale $450,000

View 137 Cornwall Rd Winter Park FL
View Details 28 Photos
View 137 Cornwall Rd Winter Park FL
View 137 Cornwall Rd Winter Park FL
View 137 Cornwall Rd Winter Park FL
Listed For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1580

  • Year Built

    1962

  • $/SqFt

    $285

Winter Park Pines - Out back, there is just enough room for family cookouts without being bothered by unwanted noise. Schedule your showing today! MLS#O6023929. PARK PLACE REAL ESTATE.

Home For Sale $399,000

View Details 30 Photos
Listed For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1424

  • Year Built

    1968

  • $/SqFt

    $280

Eastbrook - Perfect for 2 cars with plenty of room, or even a moderate sized boat. MLS#O6026826. EXP REALTY LLC.

Home For Sale $300,000

View Details 19 Photos
Listed For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1340

  • Year Built

    1986

  • $/SqFt

    $224

Temple Terrace - Make this charming home yours today! MLS#O6026597. JOSHUA UNLIMITED INC.

Home For Sale $1,200,000

View Details 3 Photos
Listed For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2505

  • Year Built

    2023

  • $/SqFt

    $479

Winter Park Village - Located minutes to downtown Winter Park, essential shopping, theme parks, downtown and major roadways. You’ll love living here! MLS#O6010529. EXP REALTY LLC.

Home For Sale $499,000

View Details 22 Photos
Listed For 3 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1260

  • Year Built

    1953

  • $/SqFt

    $396

Minutes away from Winter Park's cultural shopping district/community events - Park Avenue, museums, Rollins College, Full Sail and UCF. MLS#O6026449. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $495,000

View Details 37 Photos
Listed For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1740

  • Year Built

    1981

  • $/SqFt

    $284

Do miss your opportunity to own this great home. Schedule your private showing today! MLS#O6026815. COLDWELL BANKER REALTY.

Home For Sale $399,500

View Details 29 Photos
Listed For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1703

  • Year Built

    1970

  • $/SqFt

    $235

Eastbrook - Great location close to shopping and major roadways! MLS#O6026630. LA ROSA REALTY LAKE NONA INC.

Home For Sale $399,000

View Details 3 Photos
Listed For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1682

  • Year Built

    1963

  • $/SqFt

    $237

Terrazzo is desirable and I did not want to change it so the buyer can change to their taste in case they do not like Terrazzo. MLS#O6026910. POWERHOUSE BROKERS INT'L.

Home For Sale $899,000

View Details 34 Photos
Listed For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2110

  • Year Built

    1955

  • $/SqFt

    $426

Well-fed irrigation and no HOA fee make for low monthly costs! MLS#O6025466. COLDWELL BANKER REALTY.

Home For Sale $560,000

View Details 43 Photos
Listed For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1876

  • Year Built

    1965

  • $/SqFt

    $299

Winter Park Pines - Walk out your front door to the beautiful Cady Way Trail where families can walk, jog, skate or bike or walk across the street to the community amenities which include soccer fields, baseball fields, playground, tennis courts, and a YMCA owned and operated Olympic sized pool. Schedule your appointment now! ! MLS#V4924546. AMERICA'S HOME REALTY GROUP.

Home For Sale $469,000

View Details 31 Photos
*POTENTIAL GREAT VALUE
Listed For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2186

  • Year Built

    1975

  • $/SqFt

    $215

Please submit on FARBAR AS IS contract with Pre-Qualification letter or POF. MLS#O6018891. V 3 RESIDENTIAL LLC.

Home For Sale $2,749,000

View Details 2 Photos
Listed For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3617

  • Year Built

    2022

  • $/SqFt

    $760

5 minute drive to all the shops and restaurants on Park Ave contact the builder/listing agent for more information on finishes and timeline. MLS#O6026019. BALDWIN PARK REALTY LLC.

Home For Sale $1,695,000

View Details 63 Photos
Listed For 5 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3721

  • Year Built

    2004

  • $/SqFt

    $456

Don’t miss seeing this gorgeous home! MLS#O6025150. PREMIER SOTHEBY'S INTL. REALTY.

Pended $2,850,000

View Details 40 Photos
Listed For 7 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4802

  • Year Built

    2008

  • $/SqFt

    $594

Home is currently on septic, but city sewer is available on street and can be switched over. MLS#O6025485. PREMIER SOTHEBY'S INTL. REALTY.

Pended $725,000

View Details 35 Photos
*POTENTIAL GREAT VALUE
Listed For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2402

  • Year Built

    2017

  • $/SqFt

    $302

Golfview - This homes convenient location is accessible to all that College Park, Winter Park, Park Avenue, and Mills Avenue have to offer with the ease of getting to Interstate-4 for commuting around Orlando! MLS#O6024847. WATSON REALTY CORP.

Pended $650,000

View Details 83 Photos
Listed For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2031

  • Year Built

    1984

  • $/SqFt

    $320

Garden Lake Estates - Only 11 minutes away to Full Sail University, 17 minutes to UCF or Valencia College East Campus, 21 minutes to Rollins College. MLS#O6022766. AMERICA REAL ESTATE COMPANY LL.

Home For Sale $2,800,000

View Details 53 Photos
Listed For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3669

  • Year Built

    1991

  • $/SqFt

    $763

Cloister Grove - Conveniently located on an “Olde” Winter Park brick street, this home is a must see. Furniture negotiable. MLS#O6022155. RE/MAX ASSURED.

Pended $2,200,000

View Details 30 Photos
Listed For 8 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4386

  • Year Built

    2007

  • $/SqFt

    $502

It’s a fabulous home in a great neighborhood! MLS#O6016401. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,595,000

View Details 33 Photos
Listed For 8 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3466

  • Year Built

    2000

  • $/SqFt

    $460

This property offers a great deal of enjoyment and is one not to be missed! MLS#O6024871. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,150,000

Reduced By $40,000
View Details 44 Photos
Listed For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2540

  • Year Built

    1952

  • $/SqFt

    $453

Truly move in ready with one of the best Winter Park locations across the street from Phelps Park with pickleball, tennis, basketball, playground and the YMCA! MLS#O6025064. KELLER WILLIAMS WINTER PARK.

Home For Sale $600,000

View Details 32 Photos
Listed For 8 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1554

  • Year Built

    1935

  • $/SqFt

    $386

If you're looking for a completely turn-key home in the heart of Winter Park with easy access to shopping, dining, theme parks, beaches, and the International Airport, then this home should be at the top of your list! MLS#O6025484. DON HARKINS REALTY LLC.

Pended $599,900

View Details 16 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1601

  • Year Built

    1945

  • $/SqFt

    $375

Fontainebleau - Located minutes to Park Avenue shops, bistros, Rollins College and many majestic Parks. MLS#O6024741. EXP REALTY LLC.

Home For Sale $599,000

Reduced By $41,000
View Details 38 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2052

  • Year Built

    1978

  • $/SqFt

    $292

Flora Park - Schedule your appointment today for your chance to MAKE THIS HOUSE YOUR HOME!! ! MLS#O6025331. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $429,900

View Details 28 Photos
*POTENTIAL GREAT VALUE
Listed For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1955

  • Year Built

    1964

  • $/SqFt

    $220

Zoned for Top Rated schools: Lake Monte Elementary, Maitland Middle and Winter Park High School. MLS#O6025353. HOME IMAGINED.

Pended $400,000

View Details 33 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1430

  • Year Built

    1970

  • $/SqFt

    $280

Call today for your private showing! MLS#O6024363. WEMERT GROUP REALTY LLC.

Home For Sale $325,900

View Details 34 Photos
Listed For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1187

  • Year Built

    1994

  • $/SqFt

    $275

Winter Green - Enjoy your pond view from Kitchen, living room and master suit.. Close to all central Florida has to offer. More photos coming 3/14/22 MLS#S5067511. TCA REALTY, LLC.

Home For Sale $2,890,000

View Details 5 Photos
Listed For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4325

  • Year Built

    2022

  • $/SqFt

    $668

Call today for the updated look book. MLS#O6025012. THE HOPE GROUP.

Home For Sale $2,250,000

View Details 47 Photos
Listed For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4038

  • Year Built

    2011

  • $/SqFt

    $557

100 Stirling Avenue truly has the perfect Winter Park location, just minutes to Park Avenue, Rollins college, YMCA and Interlachen Country Club, zoned for A-rated Winter Park Schools, and no HOA. MLS#O6022861. RE/MAX TOWN & COUNTRY REALTY.

Pended $1,199,000

View Details 47 Photos
Listed For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2767

  • Year Built

    2001

  • $/SqFt

    $433

Convenient and highly desirable location in downtown Winter Park, with easy access to Rollins, Maitland City Centre, and I-4, zoned for great public schools with many nearby private schools as well. Roof being sold "AS IS" MLS#O6025025. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $700,000

View Details 46 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2800

  • Year Built

    2015

  • $/SqFt

    $250

Schedule your private showing and start living the idyllic Florida lifestyle TODAY! MLS#O6024907. WEMERT GROUP REALTY LLC.

Home For Sale $699,900

View Details 25 Photos
*POTENTIAL GREAT VALUE
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3401

  • Year Built

    1994

  • $/SqFt

    $206

Lost Creek - Set up your private tour of this home today! MLS#O6020666. SOTERA LIVING.

Pended $449,733

View Details 48 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1986

  • $/SqFt

    $236

This home will be gone in a flash, make your appointment today! ! MLS#O6025118. EXP REALTY LLC.

Pended $425,000

View Details 23 Photos
Listed For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1554

  • Year Built

    1969

  • $/SqFt

    $273

Winter Woods - There is no mandatory HOA and you are minutes to shopping, the 417, downtown Winter Park, Altamonte Springs, I4 and to Downtown Orlando. MLS#O6025024. BHHS FLORIDA REALTY.

Pended $399,000

View Details 22 Photos
Listed For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1275

  • Year Built

    1953

  • $/SqFt

    $313

Excellent location with in minutes to downtown Winter Park and College Park and Orlando. MLS#O6021916. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $375,000

View Details 48 Photos
Listed For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1235

  • Year Built

    1977

  • $/SqFt

    $304

Wrenwood Heights - This Move in Ready Home is waiting for you to call it yours! MLS#O6024384. NEXTHOME NEIGHBORHOOD REALTY.

Home For Sale $230,000

View Details 26 Photos
*POTENTIAL GREAT VALUE
Listed For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1260

  • Year Built

    1958

  • $/SqFt

    $183

Fairbanks Shores - Don't blink, or you just might miss it! MLS#O6025369. KELLER WILLIAMS CLASSIC.

Pended $4,250,000

View Details 5 Photos
Listed For 10 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5633

  • Year Built

    2004

  • $/SqFt

    $754

Cloister Grove - Wonderful location in the heart of the Via's on beautiful tree-line brick street. MLS#O6024742. PREMIER SOTHEBY'S INTL. REALTY.

Pended $985,000

View Details 66 Photos
Listed For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2722

  • Year Built

    1995

  • $/SqFt

    $362

Wonderful schools and location are why so many call Winter Park home. MLS#O6024626. BHHS FLORIDA REALTY.

Pended $599,999

View Details 25 Photos
Listed For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2174

  • Year Built

    1989

  • $/SqFt

    $276

Bear Gully Bay - **Please submit highest and best no later than than 7pm on Saturday 5/14! ** MLS#O6023831. HOMESMART.

Pended $359,000

View Details 6 Photos
Listed For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1530

  • Year Built

    1982

  • $/SqFt

    $235

Wrenwood Heights - Located on a quiet street and close to everything you might need. Great updating possibilities! MLS#A4534959. FLATFEE.COM.

Pended $350,000

View Details 1 Photo
Listed For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1337

  • Year Built

    1955

  • $/SqFt

    $262

Property is being sold MLS#O6024677. COLDWELL BANKER REALTY.

Pended $3,200,000

View Details 40 Photos
Listed For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4949

  • Year Built

    1938

  • $/SqFt

    $647

Oozing with character, this prime Winter Park estate won’t last long. MLS#O6024040. FANNIE HILLMAN & ASSOCIATES.

Pended $1,247,000

View Details 46 Photos
Listed For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2819

  • Year Built

    1963

  • $/SqFt

    $442

Call for your private showing today. MLS#O6024342. ADAIR REALTY INC.

Home For Sale $558,000

View Details 23 Photos
Listed For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2017

  • Year Built

    1958

  • $/SqFt

    $277

Conveniently located minutes away from highly sought-after schools, residents also get to enjoy close proximity to shopping, Winter Park Village, Rollins College, Advent Health, Winter Park Pines Golf Course. Motivated Seller, COME AND SEE! MLS#O6024506. MEI'S GLOBAL REALTY INC.

Home For Sale $495,900

Reduced By $44,000
View Details 31 Photos
Listed For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1828

  • Year Built

    1961

  • $/SqFt

    $271

Close access to Downtown Winter Park, Downtown Orlando, UCF, Rollins, Orlando International Airport, SR 436, 417 and 408. MLS#O6024353. CHARLES RUTENBERG REALTY ORLANDO.

Pended $459,900

View Details 25 Photos
Listed For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1337

  • Year Built

    1942

  • $/SqFt

    $344

!Unique opportunity to live in one of the best areas of Orlando! MLS#S5067049. COZY AMERICAN HOME FLORIDA INC.

Home For Sale $2,100,000

View Details 35 Photos
Listed For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3523

  • Year Built

    2018

  • $/SqFt

    $596

Kenilworth Shores - Zoned for the coveted Brookshire school district. Schedule your showing today. MLS#O6024048. KELLY PRICE & COMPANY LLC.

Viewing HOMES 1 to 50 of 196

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
$482,092
$415,000
71
2.8%
26.8%
49

Apopka
$476,519
$449,995
300
1.0%
16.0%
64

Belle Isle
$640,122
$549,500
20
5.0%
35.0%
47

Casselberry
$398,155
$414,000
69
2.9%
20.3%
42

Celebration
$1,422,378
$1,099,500
46
0.0%
37.0%
72

Champions Gate
$763,200
$807,450
18
0.0%
27.8%
80

Chuluota
$803,191
$657,500
22
9.1%
18.2%
74

Clermont
$535,686
$494,500
417
0.5%
16.8%
64

Gotha
$662,150
$506,000
12
0.0%
8.3%
140

Groveland
$508,495
$415,000
157
0.0%
12.7%
83

Harmony
$495,845
$435,000
25
0.0%
20.0%
48

Kissimmee
$499,694
$420,000
1041
0.8%
11.6%
53

Longwood
$697,706
$529,000
170
0.6%
23.5%
47

Maitland
$874,154
$565,000
63
0.0%
25.4%
38

Minneola
$508,079
$500,000
57
0.0%
17.5%
64

Montverde
$1,264,893
$899,000
49
0.0%
14.3%
101

Ocoee
$453,626
$420,000
87
1.1%
12.6%
35

Orlando
$605,115
$451,000
1829
2.2%
16.5%
55

Oviedo
$595,201
$525,900
151
1.3%
13.9%
39

Poinciana
$336,939
$324,900
359
0.0%
8.1%
96

Reunion
$1,658,196
$1,235,000
106
0.0%
23.6%
116

Saint Cloud
$487,232
$429,000
662
0.3%
9.8%
74

Sanford
$523,400
$425,000
276
2.2%
19.6%
78

Sorrento
$635,028
$599,000
45
4.4%
15.6%
65

Windermere
$1,899,233
$1,150,000
153
2.0%
17.0%
66

Winter Garden
$785,436
$680,312
372
0.5%
17.7%
56

Winter Springs
$524,227
$451,500
94
5.3%
14.9%
36

EasyStreet

Call to Schedule a Showing

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