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Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $1,450,000

View 777 Halifax Ave Winter Park FL
View Details 49 Photos
View 777 Halifax Ave Winter Park FL
View 777 Halifax Ave Winter Park FL
View 777 Halifax Ave Winter Park FL
On Market Today

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3161

  • Year Built

    2021

  • $/SqFt

    $459

Located in the heart of Winter Park, known for its tree-lined streets, excellent schools, and vibrant dining and shopping scene, this home is just minutes from everything the area has to offer. MLS#O6258805. EXP REALTY LLC.

Home For Sale $725,000

View 2703 Summerfield Rd Winter Park FL
View Details 24 Photos
View 2703 Summerfield Rd Winter Park FL
View 2703 Summerfield Rd Winter Park FL
View 2703 Summerfield Rd Winter Park FL
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1746

  • Year Built

    1967

  • $/SqFt

    $415

Golfside - Ask agent about seller incentives!! WELCOME HOME MLS#O6258737. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $440,000

View 3076 Crane Strand Dr Winter Park FL
View Details 37 Photos
View 3076 Crane Strand Dr Winter Park FL
View 3076 Crane Strand Dr Winter Park FL
View 3076 Crane Strand Dr Winter Park FL
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1200

  • Year Built

    1972

  • $/SqFt

    $367

Come and tour before it’s gone! ! MLS#O6259399. KELLER WILLIAMS LEGACY REALTY.

Home For Sale $649,900

View 326 S Ranger Blvd Winter Park FL
View Details 50 Photos
View 326 S Ranger Blvd Winter Park FL
View 326 S Ranger Blvd Winter Park FL
View 326 S Ranger Blvd Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2086

  • Year Built

    1966

  • $/SqFt

    $312

**virtual Showing With Drone Pictures Available!! ! MLS#OM688636. FOUNDERS REALTY GROUP.

Home For Sale $649,000

View Details 64 Photos
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1345

  • Year Built

    1953

  • $/SqFt

    $483

Your New Dream home awaits. SCHEDULE NOW! MLS#O6259309. HANCOCK REALTY GROUP.

Home For Sale $745,000

View Details 39 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2218

  • Year Built

    1992

  • $/SqFt

    $336

Dubsdread Heights - Your next chapter awaits—schedule a private tour today! MLS#O6257931. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $550,000

View Details 1 Photo
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1524

  • Year Built

    1965

  • $/SqFt

    $361

MOVE IN READY AND WAITING FOR YOU! (More photos to follow soon.) MLS#O6258757. MAROON REALTY GROUP LLC.

Home For Sale $3,299,000

View Details 41 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4875

  • Year Built

    2008

  • $/SqFt

    $677

Maitland Shores - Relaxation and a renewed sense of self await! MLS#O6258445. COMPASS FLORIDA LLC.

Home For Sale $1,200,000

View Details 58 Photos
*POTENTIAL GREAT VALUE
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3691

  • Year Built

    1963

  • $/SqFt

    $325

With its blend of classic design and modern updates, this home is an unforgettable opportunity in one of Winter Park's most coveted neighborhoods. MLS#O6258468. KELLY PRICE & COMPANY LLC.

Home For Sale $400,000

View Details 53 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1413

  • Year Built

    1961

  • $/SqFt

    $283

Eastbrook - Homes like this don’t come around often, so act fast—your dream home awaits! MLS#O6256824. RE/MAX 200 REALTY.

Home For Sale $4,250,000

View Details 36 Photos
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4279

  • Year Built

    2005

  • $/SqFt

    $993

Improvements include new roof/2023, whole-house generator/2021, boathouse deck replaced with Trex decking and new roof/2021. MLS#O6257650. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,800,000

View Details 50 Photos
On Market For 8 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3911

  • Year Built

    2021

  • $/SqFt

    $716

Winter Park Heights - Ideally located, this home offers easy access to downtown Winter Park, Park Avenue, the YMCA, Aloma shopping center, and Whole Foods. MLS#O6257787. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,950,000

View Details 49 Photos
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2701

  • Year Built

    2024

  • $/SqFt

    $722

Sylvan Heights - Completing this house is a seamless transition from the indoor living space to the outdoor pool and entertainment space. MLS#O6257832. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,699,000

View Details 26 Photos
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3116

  • Year Built

    2014

  • $/SqFt

    $545

This masterfully designed residence offers the perfect balance of sophisticated style, modern convenience, and prime location. MLS#O6257912. CORCORAN PREMIER REALTY.

Home For Sale $1,299,000

View Details 39 Photos
On Market For 8 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4435

  • Year Built

    1950

  • $/SqFt

    $293

The possibilities are endless—don’t miss out on this incredible opportunity! MLS#O6258176. MARZUCCO REAL ESTATE.

Home For Sale $835,000

View Details 30 Photos
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2823

  • Year Built

    2018

  • $/SqFt

    $296

Call to schedule an appointment to view this marvelous Home TODAY!! ! MLS#O6257903. EMPIRE NETWORK REALTY.

Home For Sale $399,900

View Details 20 Photos
*POTENTIAL GREAT VALUE
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    1

  • Sq. Ft.

    1518

  • Year Built

    1956

  • $/SqFt

    $263

Albert Lee Ridge - The family room addition provides the flexibility to serve as a spacious primary 4th bedroom if needed. MLS#O6257350. LPT REALTY.

Pended $650,000

View Details 45 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1545

  • Year Built

    1962

  • $/SqFt

    $421

Hvac - 2020, Plumbing - 2020, Electrical - 2020, Roof - 2004 MLS#O6256507. KELLER WILLIAMS WINTER PARK.

Pended $624,900

View Details 40 Photos
On Market For 8 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    912

  • Year Built

    1925

  • $/SqFt

    $685

Don’t miss your chance to own this one-of-a-kind Winter Park gem featured in Winter Park Magazine so schedule your visit today! MLS#O6242649. PREMIER SOTHEBY'S INTL. REALTY.

Pended $375,000

View Details 19 Photos
*POTENTIAL GREAT VALUE
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1823

  • Year Built

    1983

  • $/SqFt

    $206

Bel Aire Pines - Zoned for Winter Park High School, and a short drive to highways 408, 417, I-4, Downtown Orlando, theme parks, beaches, and all that Central Florida has to offer. MLS#O6257053. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $654,900

View Details 41 Photos
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2205

  • Year Built

    1965

  • $/SqFt

    $297

Do not miss out on the perfect blend of style, comfort, and location! MLS#O6255305. BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Pended $325,000

View Details 20 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1346

  • Year Built

    1984

  • $/SqFt

    $241

Howell Estates - VOLUNTARY HOA! Call to schedule your showing! MLS#O6248794. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $550,000

Reduced By $25,000
View Details 55 Photos
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2290

  • Year Built

    1987

  • $/SqFt

    $240

Come see all this amazing home has to offer. MLS#O6254524. COLDWELL BANKER REALTY.

Home For Sale $499,000

View Details 29 Photos
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1773

  • Year Built

    1953

  • $/SqFt

    $281

Glencoe - Schedule your appointment today topreview this Winter Park jem! MLS#O6257142. UNITED REAL ESTATE PREFERRED.

Pended $635,000

View Details 25 Photos
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1551

  • Year Built

    1965

  • $/SqFt

    $409

Winter Park Pines - zoning, ready for the next owner to thoroughly enjoy their coming years. MLS#O6256413. ZEMBALA GROUP.

Home For Sale $4,100,000

View Details 18 Photos
On Market For 15 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4520

  • Year Built

    2025

  • $/SqFt

    $907

Experience the epitome of refined living at 1751 Glencoe Road, where every detail has been crafted to perfection. MLS#O6255877. COMPASS FLORIDA, LLC.

Home For Sale $2,800,000

View Details 88 Photos
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4074

  • Year Built

    2017

  • $/SqFt

    $687

Seller has recent inspection report and home appraisal. MLS#O6254839. BHHS FLORIDA REALTY.

Home For Sale $980,000

Reduced By $999,027,000
View Details 34 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2012

  • Year Built

    1960

  • $/SqFt

    $487

This home is move in ready for a growing family. MLS#O6255730. PALM PROPERTIES OF CF, INC..

Home For Sale $579,000

Reduced By $19,000
View Details 54 Photos
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2012

  • Year Built

    1984

  • $/SqFt

    $288

Tamarak - Don't miss the opportunity to experience the best of Florida while living in this exceptional property. Schedule your private showing today! MLS#O6256132. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $545,000

View Details 46 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1727

  • Year Built

    1963

  • $/SqFt

    $316

Close to the Orlando International Airport, local Lynx transportation, restaurants, and shopping centers. MLS#O6255465. RE/MAX VANTAGE.

Pended $533,345

View Details 33 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1650

  • Year Built

    2019

  • $/SqFt

    $323

Rare opportunity for a less-than-5-year-old Winter Park home to come on the market these days! Hurry before it is gone! MLS#O6254677. RE/MAX 200 REALTY.

Home For Sale $439,000

View Details 26 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1738

  • Year Built

    1976

  • $/SqFt

    $253

Howell Branch Woods - Great location and close to Publix, shopping and restaurants. MLS#O6255970. FANNIE HILLMAN & ASSOCIATES.

Pended $940,000

View Details 25 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1449

  • Year Built

    1950

  • $/SqFt

    $649

Builders welcome to walk the lot with notice to owner. LISTING AGENT IS OWNER. MLS#O6252634. CHARLES RUTENBERG REALTY ORLANDO.

Pended $474,900

View Details 20 Photos
On Market For 13 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1160

  • Year Built

    1940

  • $/SqFt

    $409

Call today to schedule your private tour—this one won’t last long! MLS#O6255752. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $448,800

View Details 21 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1346

  • Year Built

    1957

  • $/SqFt

    $333

Winter Park Estates - Don’t miss the opportunity to make this exceptional property your own! NO HOA! MLS#O6255765. EXP REALTY LLC.

Pended $399,999

View Details 20 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1170

  • Year Built

    1954

  • $/SqFt

    $342

Temple Terrace - The current owners have thought of everything to make this a comfortable beautiful space for the next owners! MLS#O6254753. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $295,000

View Details 17 Photos
*POTENTIAL GREAT VALUE
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1356

  • Year Built

    1956

  • $/SqFt

    $218

Don’t miss out on this rare opportunity! MLS#O6255965. THE AGENCY ORLANDO.

Pended $1,095,000

View Details 75 Photos
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4094

  • Year Built

    1994

  • $/SqFt

    $267

Call today for your private viewing of this remarkable home. MLS#O6254459. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $450,000

View Details 17 Photos
On Market For 18 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1353

  • Year Built

    1956

  • $/SqFt

    $333

Eastgate - Conveniently situated near shopping, dining, and entertainment options, this home offers both comfort and accessibility in a vibrant community.Great Winter Park and Maitland schools. MLS#O6255318. BEYCOME OF FLORIDA LLC.

Home For Sale $449,000

View Details 51 Photos
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1725

  • Year Built

    1990

  • $/SqFt

    $260

Don't miss your chance to make this exceptional house your home! MLS#O6254945. LPT REALTY.

Home For Sale $400,000

View Details 24 Photos
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1953

  • Year Built

    1968

  • $/SqFt

    $205

Casa Aloma - Asking for Conventional or Cash buyers. MLS#O6253344. PARK VIEW REALTY INC.

Pended $2,500,000

View Details 1 Photo
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3762

  • Year Built

    2016

  • $/SqFt

    $665

Winter Park Heights - Stunning Winter Park modern home on the tree streets. MLS#O6248603. COMPASS FLORIDA, LLC.

Home For Sale $969,000

View Details 37 Photos
On Market For 19 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1813

  • Year Built

    1958

  • $/SqFt

    $534

Osceola Heights - Don't miss out on this opportunity—act quickly! MLS#O6254742. ALIGN REAL ESTATE LLC.

Home For Sale $365,000

View Details 42 Photos
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1000

  • Year Built

    1959

  • $/SqFt

    $365

Eastbrook - Don't wait, schedule your showing today and jump on this amazing opportunity to live in a top rated school system with a beautiful home situated on an oversized lot! MLS#O6254779. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $469,900

View Details 12 Photos
On Market For 21 Days

  • Bedrooms

    4

  • Full Bath(s)

    1

  • Sq. Ft.

    1100

  • Year Built

    1956

  • $/SqFt

    $427

Winter Park Village - Come to see it today before it is gone!! ! MLS#O6254390. EXPLORE FLORIDA REALTY SERVICES LLC.

Pended $420,000

View Details 22 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1467

  • Year Built

    1976

  • $/SqFt

    $286

Wrenwood Heights - Centrally located, this home is a short drive from local shops and restaurants, downtown Winter Park, the 417 and is about 25 minutes from both the Orlando and Sanford airports. MLS#O6252765. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $1,729,000

Reduced By $16,000
View Details 64 Photos
On Market For 23 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3270

  • Year Built

    1951

  • $/SqFt

    $529

Jenkins - Don't miss your chance to make this truly breathtaking home yours! MLS#TB8316437. HOMECOIN.COM.

Home For Sale $750,000

Reduced By $15,000
View Details 39 Photos
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1663

  • Year Built

    1991

  • $/SqFt

    $451

Sylvan Lake Shores - Don’t miss this rare opportunity to make this adorable cottage your own or use the ample lot to build the home of your dreams. MLS#O6253722. KELLER WILLIAMS WINTER PARK.

Home For Sale $749,999

View Details 34 Photos
*POTENTIAL GREAT VALUE
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2717

  • Year Built

    1995

  • $/SqFt

    $276

Lost Creek - Situated on almost a quarter-acre corner lot in a beautiful, well-cared-for neighborhood with Seminole County Schools, this well-maintained home offers easy access to 417, is less than 20 minutes from the famous Park Avenue with some of the best shops and restaurants in the city, and 25 minutes from the airport. Schedule your showing today! MLS#O6253346. ALL REAL ESTATE & INVESTMENTS.

Pended $449,900

View Details 25 Photos
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1785

  • Year Built

    1965

  • $/SqFt

    $252

Georgetown Estates - Don't delay! Schedule your showing today. MLS#O6252283. RE/MAX TOWN & COUNTRY REALTY.

Viewing HOMES 1 to 50 of 251

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 386 801 5417 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$522,986
$446,995
130
0.8%
46.9%
85

Apopka
$529,488
$478,995
555
1.4%
47.7%
82

Belle Isle
$710,640
$537,000
27
0.0%
44.4%
70

Casselberry
$439,230
$399,500
76
3.9%
55.3%
78

Celebration
$1,355,603
$1,224,000
54
0.0%
48.1%
120

Champions Gate
$662,982
$710,000
24
0.0%
54.2%
218

Chuluota
$731,404
$525,000
27
0.0%
51.9%
62

Clermont
$566,765
$499,900
649
0.2%
52.4%
83

Gotha
$1,050,338
$669,500
20
0.0%
35.0%
73

Groveland
$482,836
$415,000
201
0.5%
61.7%
90

Harmony
$437,603
$419,900
57
0.0%
36.8%
104

Kissimmee
$510,936
$440,000
2156
1.6%
49.9%
103

Longwood
$745,018
$582,500
194
0.5%
60.8%
84

Maitland
$814,113
$625,000
76
0.0%
59.2%
92

Minneola
$555,272
$529,388
140
0.7%
35.0%
101

Montverde
$1,482,874
$1,090,052
88
0.0%
47.7%
125

Ocoee
$544,474
$495,000
156
1.3%
48.7%
76

Orlando
$668,142
$480,900
2557
1.3%
49.2%
79

Oviedo
$747,461
$635,000
179
1.1%
54.7%
76

Poinciana
$333,800
$320,900
260
0.8%
62.7%
149

Reunion
$1,590,129
$1,182,500
86
3.5%
43.0%
140

Saint Cloud
$534,294
$460,000
981
0.3%
54.5%
94

Sanford
$515,589
$411,990
403
1.2%
53.3%
87

Sorrento
$569,656
$436,040
114
0.9%
36.8%
74

Windermere
$2,085,201
$1,250,000
240
0.0%
49.2%
109

Winter Garden
$840,027
$689,500
596
0.3%
46.3%
91

Winter Springs
$552,899
$461,000
120
1.7%
63.3%
81

EasyStreet

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