EasyStreet Realty
REALTOR ®
(386) 214-7941
Email Ray
mobile navigation links
244 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $7,250,000

View 500 N Interlachen Ave Winter Park FL
View Details 72 Photos
View 500 N Interlachen Ave Winter Park FL
View 500 N Interlachen Ave Winter Park FL
View 500 N Interlachen Ave Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4581

  • Year Built

    1934

  • $/SqFt

    $1,583

Located in charming Winter Park, FL, this magnificent estate is just a short walk to award-winning dining and boutique shops as well as the Alfond Inn, Rollins College, and many other nearby historic sites and attractions. MLS#O6206309. KELLY PRICE & COMPANY LLC.

Home For Sale $2,795,000

View 2412 Chantilly Ave Winter Park FL
View Details 63 Photos
View 2412 Chantilly Ave Winter Park FL
View 2412 Chantilly Ave Winter Park FL
View 2412 Chantilly Ave Winter Park FL
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4500

  • Year Built

    2024

  • $/SqFt

    $621

Winter Park Village - Experience the pinnacle of luxury living with this exceptional new construction home. MLS#O6206511. COMPASS FLORIDA LLC.

Home For Sale $850,000

View 2013 Kimbrace Pl Winter Park FL
View Details 30 Photos
View 2013 Kimbrace Pl Winter Park FL
View 2013 Kimbrace Pl Winter Park FL
View 2013 Kimbrace Pl Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2478

  • Year Built

    1957

  • $/SqFt

    $343

A short drive or bike ride to Rollins College and to shops and restaurants on Park Ave. Don’t miss out on this gem, book your showing appointment today. MLS#O6206303. HOMEVEST REALTY.

Home For Sale $489,000

View 1825 Chilean Ln Winter Park FL
View Details 28 Photos
View 1825 Chilean Ln Winter Park FL
View 1825 Chilean Ln Winter Park FL
View 1825 Chilean Ln Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1636

  • Year Built

    1961

  • $/SqFt

    $299

Eastbrook - So be quick as this one will not hang around long! Make your offer MLS#O6206543. CENTURY 21 CARIOTI.

Home For Sale $465,000

View Details 27 Photos
On Market For 5 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1632

  • Year Built

    1971

  • $/SqFt

    $285

Come and take a look today! MLS#O6205382. MILLER GRANT AND COMPANY.

Home For Sale $400,000

View Details 24 Photos
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1627

  • Year Built

    1961

  • $/SqFt

    $246

Eastbrook - NO HOA! Schedule your private showing today! MLS#O6206562. FLOBELLA REALTY LLC.

Pended $5,500,000

View Details 18 Photos
On Market For 1 Day

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    3442

  • Year Built

    1940

  • $/SqFt

    $1,598

Don't miss this rare opportunity to experience the ultimate blend of luxury, convenience and natural beauty. MLS#O6195846. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,895,000

View Details 64 Photos
On Market For 3 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3423

  • Year Built

    2014

  • $/SqFt

    $554

Lake Knowles Terrace - Original Windsor Home-http://www.nicolegibbonsstyle.com/2012/07/magnificent-house-windsor-gwyneth-paltrow.html

MLS#O6205484. KELLY PRICE & COMPANY LLC.

Home For Sale $730,000

View Details 35 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2798

  • Year Built

    2015

  • $/SqFt

    $261

Come see all that makes this home so special. MLS#O6204349. KELLER WILLIAMS CLASSIC.

Home For Sale $650,000

View Details 34 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1978

  • $/SqFt

    $303

Roof - 2023, Hvac - 2018, Electric - 2011. MLS#O6200795. KELLER WILLIAMS WINTER PARK.

Home For Sale $639,000

View Details 65 Photos
*POTENTIAL GREAT VALUE
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2407

  • Year Built

    1953

  • $/SqFt

    $265

Lawndale - Don't miss this opportunity to own a sophisticated and impeccably updated home in a prime Winter Park location, offering both luxury and convenience at your doorstep. Schedule your showing today! MLS#O6202988. COLDWELL BANKER REALTY.

Home For Sale $598,000

View Details 36 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1897

  • Year Built

    1966

  • $/SqFt

    $315

Easy access to Winter Park shopping, dining and restaurants as well as the Orlando International airport, UCF and Rollins college. Schedule your showing today! MLS#O6202425. COLDWELL BANKER REALTY.

Home For Sale $425,000

View Details 31 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1558

  • Year Built

    1980

  • $/SqFt

    $273

Cedar Ridge - Don't miss your chance to make this Winter Park gem your own – schedule a showing today and experience the epitome of Florida living! MLS#O6204317. KELLER WILLIAMS ADVANTAGE 2 REALTY.

Home For Sale $399,995

View Details 26 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1250

  • Year Built

    1961

  • $/SqFt

    $320

Winter Park Estates - Don't miss your chance to make this dream a reality - schedule your showing today! MLS#O6205934. RE/MAX INNOVATION.

Home For Sale $474,900

View Details 52 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1808

  • Year Built

    1984

  • $/SqFt

    $263

Country Lane - LIMITED ACCESS to the lake (kayak, canoe, paddleboard) and wonderful for evening SUNSETS and morning FISHING!! Text your agent now! MLS#O6203688. TOP VALUE PROPERTIES LLC.

Home For Sale $399,000

View Details 24 Photos
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1282

  • Year Built

    1957

  • $/SqFt

    $311

Enjoy all of the benefits of a Winter Park location including easy access to Winter Park Hospital, Rollins College, and infamous Park Avenue. MLS#O6205578. OLDE TOWN BROKERS INC.

Home For Sale $330,000

View Details 21 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1205

  • Year Built

    1949

  • $/SqFt

    $274

Karolina On Killarney - Winter Park shopping and entertainment all just minutes away! New roof in 2022. MLS#O6201057. SPARROW REALTY & RENTALS.

Pended $1,495,000

View Details 1 Photo
On Market For 1 Day

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3272

  • Year Built

    1956

  • $/SqFt

    $457

Minutes to top-notch public and private schools. MLS#O6200361. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $469,500

View Details 18 Photos
On Market For 5 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1036

  • Year Built

    1950

  • $/SqFt

    $453

Carver Town - Ideal for those who value the blend of modern updates and prime location, this home offers an excellent opportunity to enjoy the best of downtown Winter Park living without the luxury price tag. MLS#O6205155. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,350,000

View Details 71 Photos
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2688

  • Year Built

    2004

  • $/SqFt

    $502

Conveniently located just minutes away from Winter Park's upscale retail and dining options, don’t miss your opportunity to make this home yours today! MLS#O6195756. KELLY PRICE & COMPANY LLC.

Home For Sale $1,325,000

View Details 31 Photos
*POTENTIAL GREAT VALUE
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3834

  • Year Built

    1940

  • $/SqFt

    $346

Golfview - Schedule a showing today and make this your dream home! MLS#O6204804. COSTAL LIGHTHOUSE INVESTMENTS.

Home For Sale $1,089,000

View Details 38 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2267

  • Year Built

    1986

  • $/SqFt

    $480

Schedule a showing today and experience the allure 1621 Lasbury Avenue has to offer. MLS#O6202020. COMPASS FLORIDA LLC.

Pended $480,000

View Details 1 Photo
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1460

  • Year Built

    1958

  • $/SqFt

    $329

Brookshire Heights - Under Contract - not accepting backup offers at this time. MLS#O6204799. COMPASS FLORIDA LLC.

Home For Sale $5,200,000

View Details 32 Photos
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5681

  • Year Built

    1985

  • $/SqFt

    $915

Virginia Heights - Don't miss your chance to own this exceptional lakefront estate property, where every day feels like a vacation. Schedule your private tour today! MLS#O6203847. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,895,000

View Details 47 Photos
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3059

  • Year Built

    1989

  • $/SqFt

    $619

Comstock Park - Contact us today to schedule a private viewing and make this your dream home. MLS#O6203973. CORCORAN PREMIER REALTY.

Home For Sale $1,895,000

View Details 46 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3653

  • Year Built

    1951

  • $/SqFt

    $519

Cloister Grove - Do not miss the opportunity to live in one of Winter Park’s most sought after neighborhoods. MLS#O6203731. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,000,000

View Details 15 Photos
*POTENTIAL GREAT VALUE
On Market For 79 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3902

  • Year Built

    1969

  • $/SqFt

    $256

Just 4 miles to downtown Park Avenue shopping and dining district. MLS#O6202663. COLDWELL BANKER REALTY.

Home For Sale $439,990

View Details 27 Photos
On Market For 9 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1635

  • Year Built

    1976

  • $/SqFt

    $269

Woodcrest - Schedule your visit today and come see why this should be your next home. MLS#O6204096. FUTURE HOME REALTY INC.

Home For Sale $3,125,000

View Details 54 Photos
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3576

  • Year Built

    2007

  • $/SqFt

    $874

Of course, the location is one of the most outstanding features of this home- Walk to Farmers market, Park Avenue shoppes and restaurants and of course the Winter park 9 just one house away. MLS#O6203301. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,499,900

View Details 55 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2846

  • Year Built

    2003

  • $/SqFt

    $527

Charmont - See links for WALKTHROUGH VIDEO and MATTERPORT TOUR. MLS#O6201138. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $460,000

View Details 23 Photos
On Market For 34 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1444

  • Year Built

    1980

  • $/SqFt

    $319

Oakcrest - Schedule your showing today and fall in love with your new Winter Park pool home filled with modern updates and tons of charm! MLS#O6201703. WEMERT GROUP REALTY LLC.

Home For Sale $457,500

View Details 18 Photos
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1500

  • Year Built

    1965

  • $/SqFt

    $305

Georgetown Estates - This Home Is Ready For The New Buyers! MLS#O6203487. DEVLIN INVESTORS & ASSOCIATES.

Home For Sale $444,000

Reduced By $999
View Details 30 Photos
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1512

  • Year Built

    1969

  • $/SqFt

    $294

Eastbrook - This home is all set for easy living—come check it out! MLS#O6203876. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $439,000

View Details 29 Photos
On Market For 10 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1262

  • Year Built

    1978

  • $/SqFt

    $348

Howell Branch Woods - Nestled in the desirable Winter Park area and free from the constraints of an HOA, this residence promises both convenience and freedom, inviting you to make it your own slice of paradise. MLS#O6203723. ADAMUS REALTY GROUP, INC.

Home For Sale $330,000

View Details 17 Photos
*POTENTIAL GREAT VALUE
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1531

  • Year Built

    1962

  • $/SqFt

    $216

Eastbrook - Seller responds to most offers in 24 hours but please allow up to 72 hours for a response. MLS#S5104482. GRP.

Home For Sale $619,000

View Details 40 Photos
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2295

  • Year Built

    1989

  • $/SqFt

    $270

Schedule a visit today and see it for yourself! MLS#O6202722. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,895,000

View Details 35 Photos
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3217

  • Year Built

    1952

  • $/SqFt

    $589

Cloister Grove - An exclusive respite, this home represents the epitome of Winter Park living at its finest. MLS#O6202026. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,850,000

View Details 72 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3478

  • Year Built

    2003

  • $/SqFt

    $532

Dixie Terrace - Welcome to your new home in Winter Park, designed for those who desire the very best in life. MLS#O6200787. HOMEVEST REALTY.

Pended $1,099,000

View Details 35 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2169

  • Year Built

    1958

  • $/SqFt

    $507

With all these fabulous highlights combined, this home promises an exceptional living experience! MLS#O6200234. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $398,990

View Details 43 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1160

  • Year Built

    1957

  • $/SqFt

    $344

Tanglewood - (Some pictures are one year old) MLS#S5104475. LA ROSA REALTY KISSIMMEE.

Home For Sale $2,650,000

View Details 26 Photos
On Market For 15 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3731

  • Year Built

    2024

  • $/SqFt

    $710

View detailed design and inspiration deck at https://urbanperchhomes.com/1791-taylor-avenue-winter-park-fl-32789-custom-home/ MLS#O6202078. KELLER WILLIAMS WINTER PARK.

Home For Sale $915,000

View Details 53 Photos
On Market For 61 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2548

  • Year Built

    1940

  • $/SqFt

    $359

This home is centrally located, just a short drive to all major roadways, is in a great school district and is a short walk or bike ride to shops, restaurants and so much more! MLS#O6195868. MAINFRAME REAL ESTATE.

Home For Sale $658,900

Reduced By $1,000
View Details 25 Photos
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1764

  • Year Built

    1960

  • $/SqFt

    $374

Come to see your dream home today! MLS#O6202560. EXPLORE FLORIDA REALTY SERVICES LLC.

Pended $1,575,000

View Details 50 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3245

  • Year Built

    2016

  • $/SqFt

    $485

Brookshire Heights - * Video depicts yellow front door, this has been updated to Blue* MLS#O6199777. PREFERRED REAL ESTATE BROKERS.

Home For Sale $779,000

Reduced By $20,000
View Details 30 Photos
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2289

  • Year Built

    1968

  • $/SqFt

    $340

Winter Park Pines - Don't miss your chance to make this stunning property your own – schedule a showing today and experience the epitome of modern living at 754 Gilbert Rd. MLS#O6202180. LEERDAM PROPERTIES INC..

Home For Sale $600,000

View Details 40 Photos
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1950

  • $/SqFt

    $383

Glencoe - Don't miss out—schedule your showing today and seize the opportunity to make this dream home yours. MLS#O6202325. LA ROSA REALTY ORLANDO LLC.

Home For Sale $439,000

View Details 32 Photos
On Market For 32 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1512

  • Year Built

    1967

  • $/SqFt

    $290

MLS#O6194293. BEAR TEAM REAL ESTATE.

Home For Sale $1,895,000

View Details 40 Photos
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3361

  • Year Built

    2007

  • $/SqFt

    $564

Charmont - Discover the perfect blend of historic charm and modern luxury in this exquisite home—a true sanctuary in the heart of Winter Park. MLS#O6201554. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $775,000

View Details 46 Photos
On Market For 16 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2902

  • Year Built

    1997

  • $/SqFt

    $267

It is conveniently located to SR 417, lots of restaurants and shopping! Please schedule your appointment today! MLS#O6201350. RE/MAX TOWN & COUNTRY REALTY.

Pended $650,000

View Details 35 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1668

  • Year Built

    1961

  • $/SqFt

    $390

This delightful property combines thoughtful updates with timeless charm, making it a must-see for those desiring a turn-key home in Winter Park. MLS#O6201320. LIGHTHOUSE PROPERTY GRP INC.

Viewing HOMES 1 to 50 of 244

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 386 214 7941 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$577,014
$445,000
93
1.1%
37.6%
79

Apopka
$511,793
$471,045
506
1.6%
43.3%
78

Belle Isle
$872,141
$725,000
27
3.7%
55.6%
67

Casselberry
$446,043
$447,000
68
4.4%
44.1%
74

Celebration
$1,409,400
$1,237,450
54
0.0%
51.9%
110

Champions Gate
$664,542
$694,500
28
0.0%
42.9%
175

Chuluota
$1,193,392
$578,700
26
3.8%
53.8%
68

Clermont
$581,440
$499,000
567
0.7%
45.5%
88

Gotha
$938,269
$582,450
16
0.0%
43.8%
58

Groveland
$460,794
$413,285
203
1.5%
42.4%
73

Harmony
$440,904
$424,945
52
1.9%
55.8%
99

Kissimmee
$536,798
$459,900
1908
0.7%
45.1%
99

Longwood
$770,727
$619,900
181
1.1%
42.5%
65

Maitland
$1,176,559
$650,000
70
0.0%
35.7%
85

Minneola
$567,527
$528,495
110
0.0%
23.6%
84

Montverde
$1,668,066
$1,190,999
57
0.0%
35.1%
135

Ocoee
$547,006
$489,450
124
1.6%
41.1%
64

Orlando
$690,305
$499,000
2314
1.5%
40.5%
85

Oviedo
$682,426
$599,000
171
0.6%
34.5%
52

Poinciana
$330,468
$319,900
433
0.7%
53.6%
127

Reunion
$1,641,983
$1,200,000
87
0.0%
55.2%
168

Saint Cloud
$529,031
$458,750
882
0.1%
43.8%
92

Sanford
$520,727
$427,000
368
0.3%
53.5%
90

Sorrento
$651,626
$489,900
100
0.0%
53.0%
78

Windermere
$2,352,916
$1,485,000
238
0.8%
45.0%
93

Winter Garden
$839,407
$699,900
563
0.0%
38.2%
80

Winter Springs
$558,182
$510,000
124
1.6%
44.4%
60

EasyStreet

Call to Schedule a Showing

(386) 214-7941

(386) 214-7941