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Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $2,200,000

View 1840 Bryan Ave Winter Park FL
View Details 64 Photos
View 1840 Bryan Ave Winter Park FL
View 1840 Bryan Ave Winter Park FL
View 1840 Bryan Ave Winter Park FL
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3727

  • Year Built

    2014

  • $/SqFt

    $590

Don't miss the opportunity to own this exquisite property in Winter Park, where luxury and comfort come together seamlessly. Schedule your private showing today! MLS#O6219067. OLDE TOWN BROKERS INC.

Home For Sale $1,395,000

View 1932 Temple Dr Winter Park FL
View Details 55 Photos
View 1932 Temple Dr Winter Park FL
View 1932 Temple Dr Winter Park FL
View 1932 Temple Dr Winter Park FL
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2432

  • Year Built

    1952

  • $/SqFt

    $574

Lake Knowles Terrace - A great investment opportunity to live among the finest homes in Winter Park and in well well-established neighborhood providing a lifestyle like no other. MLS#O6218751. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,200,000

View 1771 Windsor Dr Winter Park FL
View Details 27 Photos
View 1771 Windsor Dr Winter Park FL
View 1771 Windsor Dr Winter Park FL
View 1771 Windsor Dr Winter Park FL
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2059

  • Year Built

    1953

  • $/SqFt

    $583

So, embrace the legacy of timeless design and sophisticated comfort in this beautiful home that seamlessly blends the past and present. MLS#O6218556. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $650,000

View 305 Gilbert Rd Winter Park FL
View Details 43 Photos
View 305 Gilbert Rd Winter Park FL
View 305 Gilbert Rd Winter Park FL
View 305 Gilbert Rd Winter Park FL
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2031

  • Year Built

    1964

  • $/SqFt

    $320

Schedule your showing today and envision the possibilities of calling this house your new home. MLS#O6218798. LPT REALTY.

Home For Sale $565,000

View Details 31 Photos
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1533

  • Year Built

    1958

  • $/SqFt

    $369

Sells Terrace - Hot Water Heater-2024, AC-2023, Mini Split-2023, Re-Landscape-2022, Irrigation Upgrades-2022, Spray Foam Insulation in Attic-2022, Gutters-2021. MLS#O6218549. THE WILKINS WAY LLC.

Home For Sale $450,000

View Details 23 Photos
On Market Today

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1678

  • Year Built

    1982

  • $/SqFt

    $268

Garden Lake Estates - Schedule your showing today and envision your new lifestyle in this desirable community! MLS#O6218946. WEMERT GROUP REALTY LLC.

Home For Sale $435,000

View Details 30 Photos
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1530

  • Year Built

    1969

  • $/SqFt

    $284

Eastbrook - Experience the happiness that awaits—schedule a tour today and welcome home to a new chapter of blissful living! MLS#O6218349. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $4,150,000

View Details 30 Photos
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    5

  • Sq. Ft.

    4627

  • Year Built

    1987

  • $/SqFt

    $897

Experience the epitome of luxury living in this remarkable Winter Park home, where every detail has been meticulously crafted for an unparalleled lifestyle. MLS#O6217568. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,260,000

View Details 22 Photos
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2051

  • Year Built

    1952

  • $/SqFt

    $614

Osceola Shores - Property being sold AS-IS. Survey available. MLS#O6218618. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,000,000

View Details 35 Photos
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    1813

  • Year Built

    1958

  • $/SqFt

    $552

Osceola Heights - Don't miss out on this opportunity—act quickly! MLS#O6218202. ALIGN REAL ESTATE LLC.

Home For Sale $995,000

View Details 35 Photos
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2105

  • Year Built

    1960

  • $/SqFt

    $473

Kenilworth Shores - Take advantage of this fantastic opportunity! MLS#O6217655. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $825,000

View Details 40 Photos
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2452

  • Year Built

    1968

  • $/SqFt

    $336

Located minutes from Park Avenue, Winter Park Racquet Club, Interlachen Country Club, YMCA, Phelps Park, shopping, restaurants, and excellent Winter Park/Maitland schools, this beautifully maintained home offers modern comforts and traditional elegance in a prime location. MLS#O6218593. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $625,000

View Details 4 Photos
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1918

  • Year Built

    1973

  • $/SqFt

    $326

Golfside - MOVE IN READY AND WAITING FOR YOU! (More photos to follow soon.) MLS#O6218446. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,575,000

View Details 5 Photos
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2858

  • Year Built

    2024

  • $/SqFt

    $551

Lake Killarney Shores - Make an appointment today before this amazing home is gone. MLS#O6218203. CLASSIC HOMES.

Home For Sale $414,900

View Details 36 Photos
On Market For 4 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1076

  • Year Built

    1930

  • $/SqFt

    $386

The only item needed to complete this home is YOU! MLS#O6217261. RE/MAX 200 REALTY.

Home For Sale $2,895,000

View Details 68 Photos
On Market For 4 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    4264

  • Year Built

    1936

  • $/SqFt

    $679

Virginia Heights - An exquisite estate in one of Central Florida's most dynamic areas! MLS#O6217588. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $965,000

View Details 34 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2764

  • Year Built

    2010

  • $/SqFt

    $349

You must see it in person to truly appreciate all this home has to offer! MLS#O6217949. MAINFRAME REAL ESTATE.

Home For Sale $679,500

View Details 36 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1946

  • Year Built

    1967

  • $/SqFt

    $349

This one is the right place at the right time for you. MLS#T3536785. HOMECOIN.COM.

Home For Sale $730,000

View Details 20 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1598

  • Year Built

    1958

  • $/SqFt

    $457

Charmont - The circular driveway allows for easy entry and exit of the property. MLS#U8247962. WWW.HOMEZU.COM.

Home For Sale $2,250,000

View Details 49 Photos
On Market For 6 Days

  • Bedrooms

    6

  • Full Bath(s)

    3

  • Sq. Ft.

    3554

  • Year Built

    1998

  • $/SqFt

    $633

Tuscany Terrace - This home is being sold with all the furniture. MLS#O6217019. LOKATION.

Home For Sale $380,000

View Details 19 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1604

  • Year Built

    1981

  • $/SqFt

    $237

Wrenwood Heights - Check out the Zillow Tour: https://www.tourdrop.com/dtour/383561/Zillow-3D-MLS MLS#O6217129. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,489,000

View Details 65 Photos
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2024

  • $/SqFt

    $525

Winter Park Village - Don't miss the chance to turn this dream home into your own reality —schedule a private tour today and step into the lifestyle you've been envisioning. Your ideal home awaits! MLS#O6216221. PREMIER SOTHEBYS INT'L REALTY.

Home For Sale $1,150,000

View Details 38 Photos
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2045

  • Year Built

    1949

  • $/SqFt

    $562

Located within the esteemed Winter Park School District, this home offers an ideal blend of sophistication and practicality. MLS#O6216166. KORR REALTY CORP.

Home For Sale $750,000

View Details 43 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2309

  • Year Built

    1963

  • $/SqFt

    $325

Winter Park Pines - You want a place to play, you are minutes from the WP Pines golf course, Cady Way Bike trail, pool, pickleball/tennis courts, playground, and sports fields plus shopping and WP Hospital. MLS#O6216911. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $487,000

View Details 78 Photos
*POTENTIAL GREAT VALUE
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3020

  • Year Built

    1959

  • $/SqFt

    $161

For piece of mind, seller will offer a HOME WARRANTY for buyers MLS#O6214075. REDFIN CORPORATION.

Pended $379,000

View Details 16 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1592

  • Year Built

    1985

  • $/SqFt

    $238

Country Lane - LIMITED ACCESS to the lake (kayak, canoe, paddleboard) and wonderful for evening SUNSETS and morning FISHING!! Text your agent now! MLS#O6215612. TOP VALUE PROPERTIES LLC.

Home For Sale $1,100,000

Reduced By $100,000
View Details 89 Photos
*POTENTIAL GREAT VALUE
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3834

  • Year Built

    1940

  • $/SqFt

    $287

Golfview - Schedule your private tour today and make this dream home yours! MLS#O6216744. KELLER WILLIAMS WINTER PARK.

Pended $625,000

View Details 35 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1940

  • Year Built

    1979

  • $/SqFt

    $322

Greenview Winter Pines - Hvac - 2021, Electrical - 2018, Plumbing - 2018, Roof - 2014. MLS#O6209560. KELLER WILLIAMS WINTER PARK.

Pended $589,900

View Details 35 Photos
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2214

  • Year Built

    1963

  • $/SqFt

    $266

Roof - 2017, Hvac - 2014, Plumbing - 2012, Electrical - 2012. MLS#O6215930. KELLER WILLIAMS WINTER PARK.

Home For Sale $545,000

View Details 43 Photos
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2143

  • Year Built

    1996

  • $/SqFt

    $254

Don’t miss out on this exceptional home – schedule your showing today and experience all it has to offer. You will not be disappointed! MLS#O6215377. SCHULTE REALTY LLC.

Home For Sale $415,000

View Details 25 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1318

  • Year Built

    1981

  • $/SqFt

    $315

Don't miss the chance to visit this delightful property before it's off the market! MLS#O6205879. COMPASS FLORIDA LLC.

Home For Sale $2,195,000

View Details 44 Photos
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3259

  • Year Built

    2023

  • $/SqFt

    $674

Parklando - Schedule your private showing today and experience the epitome of luxury Winter Park living. MLS#O6215769. COMPASS FLORIDA, LLC.

Pended $849,000

View Details 31 Photos
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2630

  • Year Built

    1968

  • $/SqFt

    $323

Golfside - Schedule your private tour today and start living the lifestyle you deserve at 2845 Summerfield Rd! MLS#O6215965. FANNIE HILLMAN & ASSOCIATES.

Pended $318,900

View Details 42 Photos
*POTENTIAL GREAT VALUE
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1606

  • Year Built

    1977

  • $/SqFt

    $199

Howell Branch Woods - Call today to schedule a private showing! MLS#O6216148. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $2,898,980

View Details 40 Photos
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4882

  • Year Built

    2000

  • $/SqFt

    $594

Fontainebleau - Don't miss the opportunity to make this stunning home your own. MLS#O6215815. ALIGN REAL ESTATE LLC.

Home For Sale $1,495,000

View Details 27 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2795

  • Year Built

    2017

  • $/SqFt

    $535

Lake Knowles Terrace - Schedule your private tour today and make this exquisite Winter Park home your own. MLS#O6215483. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $625,000

View Details 30 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1705

  • Year Built

    1926

  • $/SqFt

    $367

Lawndale - Don't miss the opportunity to own this historic yet modernized home in the heart of Winter Park. Schedule your showing today! MLS#O6215384. KELLER WILLIAMS WINTER PARK.

Pended $549,000

View Details 41 Photos
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1800

  • Year Built

    1956

  • $/SqFt

    $305

Kenilworth Shores - Hurry, it won't last long! MLS#O6214388. PALMANO GROUP RE BROKERAGE LLC.

Pended $340,000

View Details 26 Photos
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1381

  • Year Built

    1963

  • $/SqFt

    $246

Winter Park Estates - Downtown Park Ave is just minutes away as well as easy access to highways. MLS#W7865767. BHHS FLORIDA PROPERTIES GROUP.

Pended $414,900

View Details 39 Photos
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1592

  • Year Built

    1986

  • $/SqFt

    $261

Country Lane - Call today! This home will not last. MLS#G5083540. WATSON REALTY CORP.

Home For Sale $1,929,000

View Details 44 Photos
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3590

  • Year Built

    2019

  • $/SqFt

    $537

This coastal inspired home is available for a private showing. Schedule a visit soon. MLS#O6215116. THE HOPE GROUP.

Home For Sale $1,400,000

View Details 1 Photo
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2334

  • Year Built

    2024

  • $/SqFt

    $600

Don't miss your chance to own this premier home in Winter Park! NEW PHOTOS COMING SOON! MLS#V4936864. SUMMER WIND REALTY CENTRAL FL.

Pended $1,350,000

Reduced By $140,000
View Details 60 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2743

  • Year Built

    1966

  • $/SqFt

    $492

Don't miss out on this opportunity – schedule your showing today and bring your vision to life!

MLS#O6213521. KELLY PRICE & COMPANY LLC.

Home For Sale $975,000

View Details 38 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2310

  • Year Built

    1968

  • $/SqFt

    $422

Most coveted schools - Dommerich Elementary, Maitland Middle, and Winter Park High School Don't miss the opportunity to make this your forever home – schedule a viewing today!

MLS#O6213510. KELLY PRICE & COMPANY LLC.

Home For Sale $725,000

View Details 40 Photos
On Market For 16 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1623

  • Year Built

    1940

  • $/SqFt

    $447

Sylvan Lake Shores - Come see how the curb appeal lures you into the home that you'll want to make your own! MLS#O6212981. KELLY PRICE & COMPANY LLC.

Home For Sale $710,000

Reduced By $10,000
View Details 39 Photos
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2082

  • Year Built

    1958

  • $/SqFt

    $341

Additionally, it is less than 1 mile to Trader Joe's and 1.5 miles to Park Ave. Don't miss out on this exceptional opportunity to own a piece of Winter Park paradise." MLS#O6214064. HYSER LLC.

Home For Sale $435,000

View Details 34 Photos
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1750

  • Year Built

    1967

  • $/SqFt

    $249

Eastbrook - With no HOA, this prime location home offers top-rated Seminole County schools nearby and is located near Downtown Orlando and Downtown Winter Park, as well as popular Central Florida theme parks, Winter Park hospital, public golf courses, and near Winter Park's Park Avenue boutique shopping, museums, Rollins College, Full Sail University, YMCA, and University of Central Florida, and so many other modern-day conveniences. Schedule your private showing today! MLS#O6213538. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $350,000

Reduced By $15,000
View Details 38 Photos
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1398

  • Year Built

    1958

  • $/SqFt

    $250

Winter Park Estates - Don't miss out on this fantastic opportunity! MLS#O6211598. BALDWIN PARK REALTY LLC.

Home For Sale $649,000

View Details 15 Photos
On Market For 17 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1144

  • Year Built

    1955

  • $/SqFt

    $567

Buyer will be responsible for confirming room measurements. MLS#O6214438. CHARLES RUTENBERG REALTY ORLANDO.

Pended $495,000

View Details 38 Photos
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1874

  • Year Built

    1969

  • $/SqFt

    $264

Casa Aloma - Enjoy the best of Winter Park living in an affordable home that perfectly balances modern updates with classic charm. MLS#O6214086. RE/MAX TOWN & COUNTRY REALTY.

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 407-485-1814 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$572,139
$449,950
110
0.9%
36.4%
64

Apopka
$518,768
$485,000
488
0.8%
38.3%
70

Belle Isle
$948,980
$779,950
22
0.0%
54.5%
60

Casselberry
$438,173
$422,450
88
4.5%
36.4%
49

Celebration
$1,389,741
$1,199,900
55
0.0%
41.8%
108

Champions Gate
$659,850
$699,480
25
0.0%
52.0%
181

Chuluota
$706,592
$587,000
24
4.2%
54.2%
54

Clermont
$564,027
$499,900
600
1.0%
42.7%
65

Gotha
$959,981
$682,000
16
0.0%
62.5%
60

Groveland
$454,813
$410,000
214
1.4%
49.1%
72

Harmony
$451,021
$434,990
49
2.0%
51.0%
90

Kissimmee
$533,759
$455,000
2022
1.0%
46.8%
88

Longwood
$749,658
$620,000
197
0.5%
47.2%
58

Maitland
$1,032,612
$743,415
76
0.0%
48.7%
56

Minneola
$562,066
$524,990
155
0.6%
21.9%
68

Montverde
$1,585,170
$1,165,296
66
0.0%
37.9%
121

Ocoee
$553,215
$499,000
119
2.5%
50.4%
59

Orlando
$689,004
$499,000
2372
1.2%
43.7%
62

Oviedo
$746,756
$624,500
181
0.6%
49.2%
46

Poinciana
$331,964
$320,900
393
1.0%
51.4%
120

Reunion
$1,549,003
$1,199,000
85
0.0%
56.5%
146

Saint Cloud
$537,144
$456,746
964
0.1%
47.4%
78

Sanford
$534,059
$433,000
371
0.0%
51.5%
71

Sorrento
$621,900
$447,500
84
0.0%
59.5%
85

Windermere
$2,271,123
$1,317,670
234
0.4%
47.0%
91

Winter Garden
$822,632
$699,000
588
0.0%
42.9%
74

Winter Springs
$557,955
$495,000
127
0.8%
43.3%
49

EasyStreet

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