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Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $860,000

View 1423 Westchester Ave Winter Park FL
View Details 56 Photos
View 1423 Westchester Ave Winter Park FL
View 1423 Westchester Ave Winter Park FL
View 1423 Westchester Ave Winter Park FL
On Market Today

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1700

  • Year Built

    1935

  • $/SqFt

    $506

This space can be used as an office, gym, additional bedroom and so much more. MLS#O6245627. KELLER WILLIAMS WINTER PARK.

Home For Sale $625,000

View 1926 Natalen Rd Winter Park FL
View Details 65 Photos
View 1926 Natalen Rd Winter Park FL
View 1926 Natalen Rd Winter Park FL
View 1926 Natalen Rd Winter Park FL
On Market Today

  • 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 1312 Golfside Dr Winter Park FL
View Details 36 Photos
View 1312 Golfside Dr Winter Park FL
View 1312 Golfside Dr Winter Park FL
View 1312 Golfside Dr Winter Park FL
On Market For 2 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.

Home For Sale $380,000

View 5422 S Bracken Ct Winter Park FL
View Details 39 Photos
View 5422 S Bracken Ct Winter Park FL
View 5422 S Bracken Ct Winter Park FL
View 5422 S Bracken Ct Winter Park FL
On Market For 2 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.

Home For Sale $4,100,000

View Details 74 Photos
*POTENTIAL GREAT VALUE
On Market For 3 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    6215

  • Year Built

    2006

  • $/SqFt

    $660

Top rated schools and minutes to Park Avenue shopping and dining. MLS#O6244003. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,499,000

View Details 54 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2843

  • Year Built

    2024

  • $/SqFt

    $527

Located just a short walk from Phelps Park, the YMCA, and Lakemont Elementary, and only a quick drive from Winter Park’s top shops and restaurants, this Barefoot Brothers masterpiece presents a rare opportunity to own a thoughtfully designed, luxurious home in a prime location. MLS#O6236875. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,495,000

View Details 65 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2739

  • Year Built

    1949

  • $/SqFt

    $546

Dixie Terrace - With every detail thoughtfully curated, this property is more than just a home—it's a lifestyle. MLS#O6245047. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,579,000

View Details 58 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2697

  • Year Built

    2017

  • $/SqFt

    $585

Lake Knowles Terrace - It's more than a listing—it's an invitation to elevate your lifestyle in one of Winter Park's most coveted neighborhoods. MLS#O6237936. TBRO REALTY LLC.

Home For Sale $409,990

View Details 23 Photos
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1436

  • Year Built

    1957

  • $/SqFt

    $286

Tanglewood - Call now to schedule your private showing today! MLS#O6244457. BHHS FLORIDA REALTY.

Pended $999,999

View Details 3 Photos
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1761

  • Year Built

    1950

  • $/SqFt

    $568

Charmont - Don’t miss this rare chance to invest in a property with both immediate comfort and exciting potential for the future! MLS#O6244417. PARKSIDE PROPERTIES, LLC.

Home For Sale $2,790,000

View Details 44 Photos
On Market For 7 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4882

  • Year Built

    2000

  • $/SqFt

    $571

Fontainebleau - Don't miss the opportunity to make this stunning home your own. MLS#O6244120. ALIGN REAL ESTATE LLC.

Home For Sale $699,000

View Details 24 Photos
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1682

  • Year Built

    1964

  • $/SqFt

    $416

Winter Park Pines - Within 3 miles, you have access to the VA hospital, Advent Health Hospital, Interlachen Country Club, YMCA, Rollins College, Full Sail University, Costco, Restaurants, Pharmacies, Banks, Gas Stations, Shops, and trendy Park Ave. MLS#O6243811. ELITE PROPERTY REAL ESTATE LLC.

Home For Sale $615,000

View Details 22 Photos
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2327

  • Year Built

    1977

  • $/SqFt

    $264

Lake Waunatta Woods - Also, you have the benefit of accessing nearby amenities. REQUEST AN APPOINTMENT TODAY! MLS#O6243744. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,479,000

View Details 52 Photos
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2471

  • Year Built

    1979

  • $/SqFt

    $599

Don’t miss this amazing opportunity to live and/or build in the Vias! MLS#O6239295. COMPASS FLORIDA LLC.

Home For Sale $1,199,900

View Details 30 Photos
On Market For 10 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2801

  • Year Built

    1963

  • $/SqFt

    $428

This home is a must-see, schedule a showing today! MLS#O6243230. EXP REALTY LLC.

Pended $599,000

View Details 33 Photos
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1482

  • Year Built

    1971

  • $/SqFt

    $404

Lake Knowles Terrace - With its unbeatable location and quaint neighborhood feel, this home is the perfect opportunity to start your next chapter in one of Central Florida's most sought-after communities! MLS#O6243414. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $824,999

View Details 41 Photos
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1407

  • Year Built

    1958

  • $/SqFt

    $586

Albert Lee Ridge - Don’t miss your chance to own this Lakeside retreat. MLS#O6242752. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $725,000

View Details 27 Photos
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2231

  • Year Built

    1964

  • $/SqFt

    $325

This home is perfectly situated near Winter Park Pines Golf Course, highly rated schools, shopping, and dining options, offering the best of Winter Park living. MLS#O6242880. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $479,900

View Details 49 Photos
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1959

  • $/SqFt

    $250

Eastbrook - This gem is a perfect blend of modern living in a prime location—schedule your visit today and make this dream home yours before it's gone! MLS#O6242330. LPT REALTY, LLC.

Home For Sale $1,650,000

View Details 42 Photos
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3446

  • Year Built

    1950

  • $/SqFt

    $479

Sylvan Lake Shores - Conveniently located to shopping and restaurants of Park Ave, Winter Park Advent Health, Winter Park YMCA, and Rollins College. Welcome home! MLS#O6242682. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $465,000

View Details 66 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1703

  • Year Built

    1983

  • $/SqFt

    $273

Howell Estates - Ample storage throughout the home adds practicality to its appeal. Reach out for a showing! MLS#O6241658. KELLER WILLIAMS WINTER PARK.

Home For Sale $6,975,000

View Details 93 Photos
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    7

  • Sq. Ft.

    8752

  • Year Built

    2022

  • $/SqFt

    $797

In this haven of opulent serenity, you may live the life you want, where you want. MLS#O6240628. KELLY PRICE & COMPANY LLC.

Home For Sale $1,990,000

View Details 9 Photos
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3174

  • Year Built

    2025

  • $/SqFt

    $627

Contact us today to schedule your appointment! MLS#O6241493. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $849,995

View Details 45 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2046

  • Year Built

    1964

  • $/SqFt

    $415

Kenilworth Shores - Don’t miss your chance to own this beautiful home located in a quiet neighborhood of Winter Park surrounded by well-maintained homes and is only minutes to Downtown Orlando, Shopping, Dining and Entertainment! MLS#O6239168. LEGACY REALTY & BROKERS LLC.

Home For Sale $824,990

Reduced By $24,910
View Details 95 Photos
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2200

  • Year Built

    1967

  • $/SqFt

    $375

With no HOA and these valuable updates, this home provides both comfort and convenience in one of Winter Park’s most desirable locations. MLS#O6241415. YOUNG REAL ESTATE.

Home For Sale $570,000

View Details 39 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1970

  • Year Built

    1956

  • $/SqFt

    $289

Albert Lee Ridge - Located in the desirable Winter Park area, you'll enjoy convenient access to Winter Park Village, Advent Health, Downtown Orlando, and major highways. MLS#O6241497. ANDREWS REAL ESTATE & INVESTMENT SERVICES.

Pended $499,700

View Details 26 Photos
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1942

  • Year Built

    1967

  • $/SqFt

    $257

Eastbrook - Don’t miss this exclusive opportunity to own a piece of paradise. MLS#O6241387. RESOURCE REALTY SERVICES, INC..

Home For Sale $489,000

View Details 20 Photos
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1578

  • Year Built

    1972

  • $/SqFt

    $310

Woodcrest - Don’t miss out this amazing opportunity to live in one of the most desirable neighborhoods in Winter Park, at the end of a quiet street, in a ready-to-move-in fully remodeled house with no electric bills!! ! MLS#O6241245. FATHOM REALTY FL LLC.

Home For Sale $475,000

View Details 32 Photos
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2161

  • Year Built

    1969

  • $/SqFt

    $220

Eastbrook - Roof-2014, A/C - 2018, Whole house water softener - 2021, pump for irrigation system on well water-2022 Come see for yourself how this home can be the perfect backdrop for your lifestyle! MLS#O6240165. KELLER WILLIAMS ADVANTAGE REALTY.

Pended $1,798,000

View Details 58 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2857

  • Year Built

    2024

  • $/SqFt

    $629

Don’t miss your chance to own this exceptional property—schedule your private tour today! MLS#O6241123. THE AGENCY ORLANDO.

Home For Sale $1,500,000

View Details 43 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2958

  • Year Built

    1957

  • $/SqFt

    $507

Kenilworth Shores - Don’t miss your chance to own a piece of the American Dream—schedule your private tour today. MLS#O6240903. EXP REALTY LLC.

Pended $1,475,000

View Details 61 Photos
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2659

  • Year Built

    1952

  • $/SqFt

    $555

Live the quintessential Winter Park lifestyle and request a tour of your future home. MLS#S5112075. TITAN REALTY GROUP LLC.

Home For Sale $950,000

View Details 62 Photos
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1861

  • Year Built

    2017

  • $/SqFt

    $510

Built for both beauty and energy efficiency, the home includes double-pane low-E windows, R-38 insulation, and a tankless water heater..This move-in-ready masterpiece offers not just a home but an elevated lifestyle in one of Winter Park’s most sought-after locations. Schedule your private tour today! MLS#O6238453. EXP REALTY LLC.

Home For Sale $825,000

View Details 42 Photos
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2347

  • Year Built

    2003

  • $/SqFt

    $352

This home is easy to show so arrange for your private showing now! MLS#O6240342. KELLER WILLIAMS WINTER PARK.

Pended $750,000

View Details 32 Photos
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3215

  • Year Built

    2013

  • $/SqFt

    $233

Enclave At Aloma - Don’t miss the opportunity to make this stunning Winter Park home yours today! MLS#O6240779. CREEGAN GROUP.

Home For Sale $449,999

Reduced By $5,000
View Details 42 Photos
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1476

  • Year Built

    1974

  • $/SqFt

    $305

Wrenwood Heights - Don't miss this opportunity to own a stunning, remodeled home in beautiful Winter Park! MLS#O6240219. MLSB THE BUREAU POWERED BY CAROM REALTY.

Pended $399,000

View Details 38 Photos
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1624

  • Year Built

    1983

  • $/SqFt

    $246

Garden Lake Estates - Don’t miss your chance to own this centrally located home in a fantastic school district! MLS#O6235206. EXP REALTY LLC.

Pended $350,000

View Details 30 Photos
On Market For 18 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1358

  • Year Built

    1977

  • $/SqFt

    $258

Don't miss out on the chance to own a home in this desirable area with all the big-ticket items already taken care of! MLS#O6241281. FANNIE HILLMAN & ASSOCIATES.

Pended $310,000

View Details 19 Photos
On Market For 17 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    920

  • Year Built

    1954

  • $/SqFt

    $337

With easy access to major highways, visiting Downtown Orlando or any of the amazing activities across Central Florida is a breeze. MLS#O6240941. BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY.

Pended $4,250,000

View Details 67 Photos
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4596

  • Year Built

    2024

  • $/SqFt

    $925

Tuscany Terrace - An exquisite Luxury Estate in one of Central Florida's most dynamic areas! MLS#O6239426. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $1,650,000

View Details 25 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3237

  • Year Built

    1957

  • $/SqFt

    $510

Timberlane Shores - Don’t wait to elevate your lifestyle with this stunning Winter Park property! MLS#O6237059. STOCKWORTH REALTY GROUP.

Home For Sale $1,150,000

View Details 58 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2011

  • Year Built

    1988

  • $/SqFt

    $572

Schedule your private showing today and discover the perfect blend of comfort, luxury, and outdoor living! MLS#O6239390. EXP REALTY LLC.

Home For Sale $899,000

Reduced By $80,000
View Details 28 Photos
On Market For 22 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1760

  • Year Built

    1957

  • $/SqFt

    $511

Conwill Estates - Take moment to visualize yourself in this beautiful property and then make an appointment to see it in person, you won't be disappointed! MLS#O6238911. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $580,000

View Details 25 Photos
On Market For 23 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1898

  • Year Built

    1976

  • $/SqFt

    $306

All rooms sizes should be confirmed by buyer. MLS#O6239477. EXP REALTY LLC.

Home For Sale $4,595,000

View Details 36 Photos
On Market For 24 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5633

  • Year Built

    2005

  • $/SqFt

    $816

Cloister Grove - This is a rare opportunity to own a truly exceptional home in one of Winter Park's most desirable locations. MLS#O6234338. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,590,000

Reduced By $60,000
View Details 39 Photos
On Market For 24 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2350

  • Year Built

    2024

  • $/SqFt

    $677

Schedule your visit today and fall in love with this dreamy home! MLS#O6238899. COLDWELL BANKER RESIDENTIAL RE.

Pended $1,099,000

View Details 79 Photos
On Market For 24 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2752

  • Year Built

    1980

  • $/SqFt

    $399

Call today to schedule your private showing! MLS#O6236107. KELLER WILLIAMS WINTER PARK.

Home For Sale $559,999

Reduced By $10,000
View Details 25 Photos
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1128

  • Year Built

    1954

  • $/SqFt

    $496

Orangewood Park - This home will not last long. MLS#O6238462. 407 PROPERTIES.

Pended $405,000

View Details 39 Photos
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1288

  • Year Built

    1984

  • $/SqFt

    $314

Howell Estates - It's VACANT and READY FOR IMMEDIATE MOVE-IN. WELCOME HOME. MLS#O6236172. GREATER ORLANDO REALTY, LLC.

Pended $400,000

View Details 31 Photos
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1188

  • Year Built

    1957

  • $/SqFt

    $337

Winter Park Estates - Don't miss this opportunity to own a piece of one of Central Florida's most desirable neighborhoods! Schedule your tour today! MLS#O6238848. CREEGAN GROUP.

Viewing HOMES 1 to 50 of 237

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 386-801-4854 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$575,590
$459,000
121
0.0%
52.1%
84

Apopka
$522,299
$480,000
555
1.4%
40.2%
68

Belle Isle
$740,529
$543,700
27
0.0%
55.6%
75

Casselberry
$429,136
$414,000
81
3.7%
53.1%
65

Celebration
$1,330,318
$1,024,975
52
0.0%
48.1%
114

Champions Gate
$640,469
$679,000
27
0.0%
59.3%
183

Chuluota
$770,488
$550,000
33
3.0%
57.6%
70

Clermont
$577,183
$499,900
684
0.3%
52.0%
73

Gotha
$987,874
$695,000
17
0.0%
41.2%
54

Groveland
$473,716
$410,000
199
1.0%
51.3%
77

Harmony
$441,961
$425,450
52
1.9%
46.2%
88

Kissimmee
$519,506
$448,450
2132
1.4%
50.3%
96

Longwood
$750,732
$575,000
205
0.5%
57.1%
73

Maitland
$881,947
$720,450
78
0.0%
53.8%
81

Minneola
$558,552
$529,000
155
0.0%
27.7%
81

Montverde
$1,454,526
$1,104,674
76
0.0%
43.4%
114

Ocoee
$552,184
$512,000
169
1.2%
40.2%
60

Orlando
$665,007
$491,458
2492
1.5%
48.0%
73

Oviedo
$716,332
$625,000
189
1.1%
52.9%
65

Poinciana
$336,036
$320,900
294
1.0%
59.2%
130

Reunion
$1,650,519
$1,199,999
83
2.4%
47.0%
133

Saint Cloud
$547,023
$451,935
1000
0.4%
52.4%
86

Sanford
$525,343
$413,990
409
0.7%
47.4%
76

Sorrento
$576,445
$453,740
99
1.0%
53.5%
74

Windermere
$2,229,327
$1,275,000
253
0.4%
50.6%
101

Winter Garden
$825,639
$700,283
604
0.5%
47.4%
84

Winter Springs
$550,664
$470,000
139
0.7%
54.7%
59

EasyStreet

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