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View 252 Winter Park Florida Homes for Sale

Home For Sale $449,000

View 1914 Aster Dr Winter Park FL
View Details 27 Photos
View 1914 Aster Dr Winter Park FL
View 1914 Aster Dr Winter Park FL
View 1914 Aster Dr Winter Park FL
On Market For 28 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1645

  • Year Built

    1983

  • $/SqFt

    $273

Schedule your showing today and discover the joys of living in Garden Lake Estates! MLS#O6203546. COLDWELL BANKER REALTY.

Pended $425,000

View 2032 Houndslake Dr Winter Park FL
View Details 19 Photos
View 2032 Houndslake Dr Winter Park FL
View 2032 Houndslake Dr Winter Park FL
View 2032 Houndslake Dr Winter Park FL
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1540

  • Year Built

    1980

  • $/SqFt

    $276

Cedar Ridge - Don't miss the chance to make this exquisite residence your own and create a lifetime of memories in a place you'll love to call home. MLS#O6207308. KELLER WILLIAMS HERITAGE REALTY.

Pended $2,349,000

View 1770 Oakhurst Ave Winter Park FL
View Details 61 Photos
View 1770 Oakhurst Ave Winter Park FL
View 1770 Oakhurst Ave Winter Park FL
View 1770 Oakhurst Ave Winter Park FL
On Market For 37 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3640

  • Year Built

    2019

  • $/SqFt

    $645

Jenkins - With numerous exceptional features, this home invites you to experience its luxurious beauty firsthand. MLS#O6202216. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $800,000

View 2083 Laurelwood Way Winter Park FL
View Details 42 Photos
View 2083 Laurelwood Way Winter Park FL
View 2083 Laurelwood Way Winter Park FL
View 2083 Laurelwood Way Winter Park FL
On Market For 39 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2192

  • Year Built

    2019

  • $/SqFt

    $365

Preserve At Hawks Crest - This exclusive residence is the epitome of refined living, offering a peaceful and convenient lifestyle for discerning homeowners. MLS#O6205631. PREMIER SOTHEBY'S INTL. REALTY.

Pended $541,000

View Details 15 Photos
*IS BANK OWNED
On Market For 39 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1856

  • Year Built

    1972

  • $/SqFt

    $291

Investors must complete inspections prior to bidding. MLS#O6206981. CREEGAN GROUP.

Home For Sale $699,000

View Details 45 Photos
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1664

  • Year Built

    1964

  • $/SqFt

    $420

Lake Virginia - Don't miss out on the opportunity to make this property your new home! Call today! MLS#O6206675. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $7,250,000

View Details 72 Photos
On Market For 30 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 $2,795,001

View Details 63 Photos
On Market For 43 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.
Brought to you by https://my.matterport.com/show/?m=hii6iJs7gyG MLS#O6206511. COMPASS FLORIDA LLC.

Home For Sale $850,000

View Details 30 Photos
On Market For 43 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 $419,000

Reduced By $70,000
View Details 28 Photos
On Market For 43 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1636

  • Year Built

    1961

  • $/SqFt

    $256

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

Home For Sale $400,000

View Details 24 Photos
On Market For 43 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.

Home For Sale $1,875,000

Reduced By $20,000
View Details 64 Photos
On Market For 25 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3423

  • Year Built

    2014

  • $/SqFt

    $548

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

MLS#O6205484. KELLY PRICE & COMPANY LLC.

Pended $730,000

View Details 35 Photos
*POTENTIAL GREAT VALUE
On Market For 43 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 $629,000

Reduced By $21,000
View Details 36 Photos
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2145

  • Year Built

    1978

  • $/SqFt

    $293

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

Home For Sale $615,000

Reduced By $24,000
View Details 65 Photos
*POTENTIAL GREAT VALUE
On Market For 44 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2407

  • Year Built

    1953

  • $/SqFt

    $256

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 $405,000

Reduced By $20,000
View Details 31 Photos
On Market For 43 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1558

  • Year Built

    1980

  • $/SqFt

    $260

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 $380,000

View Details 24 Photos
On Market For 44 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1616

  • Year Built

    1989

  • $/SqFt

    $235

This home will not last long! MLS#O6202818. METRO CITY REALTY.

Pended $330,000

View Details 21 Photos
On Market For 45 Days

  • Bedrooms

    2

  • 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.

Home For Sale $449,900

View Details 18 Photos
On Market For 45 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1036

  • Year Built

    1950

  • $/SqFt

    $434

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 47 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 $1,089,000

View Details 38 Photos
On Market For 45 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.

Home For Sale $4,950,000

Reduced By $250,000
View Details 33 Photos
On Market For 50 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5681

  • Year Built

    1985

  • $/SqFt

    $871

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.

Home For Sale $1,895,000

View Details 46 Photos
On Market For 50 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 $959,000

Reduced By $41,000
View Details 19 Photos
*POTENTIAL GREAT VALUE
On Market For 49 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3902

  • Year Built

    1969

  • $/SqFt

    $246

Don't miss this opportunity to live, work and play in Winter Park just 4 miles away from downtown Park Avenue shops, restaurants and recreation. MLS#O6202663. COLDWELL BANKER REALTY.

Home For Sale $2,975,000

Reduced By $150,000
View Details 58 Photos
On Market For 51 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3576

  • Year Built

    2007

  • $/SqFt

    $832

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 51 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.

Pended $450,000

Reduced By $10,000
View Details 23 Photos
On Market For 51 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1444

  • Year Built

    1980

  • $/SqFt

    $312

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.

Pended $425,000

Reduced By $14,000
View Details 29 Photos
On Market For 48 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1262

  • Year Built

    1978

  • $/SqFt

    $337

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.

Pended $313,500

Reduced By $16,500
View Details 17 Photos
*POTENTIAL GREAT VALUE
On Market For 46 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1531

  • Year Built

    1962

  • $/SqFt

    $205

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

Pended $595,000

Reduced By $24,000
View Details 40 Photos
On Market For 48 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2295

  • Year Built

    1989

  • $/SqFt

    $259

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

Home For Sale $1,875,000

Reduced By $20,000
View Details 35 Photos
On Market For 53 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3217

  • Year Built

    1952

  • $/SqFt

    $583

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 53 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.

Home For Sale $398,990

View Details 43 Photos
On Market For 53 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 54 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 $879,000

Reduced By $36,000
View Details 53 Photos
On Market For 54 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2548

  • Year Built

    1940

  • $/SqFt

    $345

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 $749,000

Reduced By $50,000
View Details 33 Photos
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2289

  • Year Built

    1968

  • $/SqFt

    $327

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 $599,000

Reduced By $1,000
View Details 40 Photos
On Market For 56 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1568

  • Year Built

    1950

  • $/SqFt

    $382

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 $419,900

Reduced By $19,100
View Details 32 Photos
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1512

  • Year Built

    1967

  • $/SqFt

    $278

MLS#O6194293. BEAR TEAM REAL ESTATE.

Home For Sale $1,799,000

Reduced By $96,000
View Details 40 Photos
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3361

  • Year Built

    2007

  • $/SqFt

    $535

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.

Pended $699,000

Reduced By $76,000
View Details 46 Photos
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2902

  • Year Built

    1997

  • $/SqFt

    $241

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 12 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.

Home For Sale $368,000

Reduced By $52,000
View Details 34 Photos
On Market For 56 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    987

  • Year Built

    1956

  • $/SqFt

    $373

Stansbury Estates - Make this your dream home today! MLS#G5081725. REAL BROKER, LLC.

Pended $1,649,000

View Details 78 Photos
On Market For 58 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3028

  • Year Built

    2006

  • $/SqFt

    $545

Don't miss your chance to experience the epitome of gracious living in one of Florida's most coveted neighborhoods. MLS#O6200815. EXP REALTY LLC.

Home For Sale $1,450,000

Reduced By $39,000
View Details 36 Photos
On Market For 58 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2812

  • Year Built

    2001

  • $/SqFt

    $516

Experience the epitome of lakeside living and make this dream home yours today. MLS#O6199613. SOTERA LIVING.

Home For Sale $548,000

Reduced By $20,000
View Details 45 Photos
On Market For 58 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1970

  • $/SqFt

    $286

Woodcrest - Whether You Are Looking For Your Dream Home Or Want To Be The Wisest Investor, This Is The Greatest You Will Ever Find! MLS#O6200506. COLDWELL BANKER REALTY.

Pended $428,990

View Details 28 Photos
On Market For 58 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1582

  • Year Built

    1956

  • $/SqFt

    $271

Tanglewood - Schedule your private tour today and discover the perfect blend of comfort, style, and convenience! MLS#O6200824. BHHS FLORIDA REALTY.

Home For Sale $749,900

Reduced By $25,000
View Details 86 Photos
*POTENTIAL GREAT VALUE
On Market For 59 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3496

  • Year Built

    2015

  • $/SqFt

    $215

Enclave At Aloma - MLS#O6201034. RE/MAX 200 REALTY.

Home For Sale $1,950,000

View Details 3 Photos
On Market For 60 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2701

  • Year Built

    2024

  • $/SqFt

    $722

Sylvan Heights - Completing this house is the clean outdoor living space with a custom detailed ceiling and flooring creating a seamless transition from the living space to the pool entertainment space. MLS#O6199494. THE HOPE GROUP.

Home For Sale $11,795,000

View Details 48 Photos
*POTENTIAL GREAT VALUE
On Market For 64 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    8188

  • Year Built

    2021

  • $/SqFt

    $1,441

Don't miss the opportunity to make this your own private paradise. MLS#O6199109. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $4,150,000

View Details 59 Photos
*POTENTIAL GREAT VALUE
On Market For 64 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6939

  • Year Built

    1999

  • $/SqFt

    $598

Comstock Park - With its timeless elegance and modern amenities, this home offers a unique lifestyle of comfort and sophistication in the heart of Winter Park. MLS#O6199396. PALMANO GROUP RE BROKERAGE LLC.

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