251 Results

View 251 Winter Park Florida Homes for Sale

Pended $1,650,000

View 2435 Chantilly Ave Winter Park FL
View 2435 Chantilly Ave Winter Park FL
View 2435 Chantilly Ave Winter Park FL
On Market For 50 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3055

  • Year Built

    2023

  • $/SqFt

    $540

Winter Park Village - Don’t miss your chance to own this extraordinary property! MLS#O6244257. FLORIDA REALTY INVESTMENTS.

Home For Sale $470,000

View 4444 Steed Ter Winter Park FL
View 4444 Steed Ter Winter Park FL
View 4444 Steed Ter Winter Park FL
On Market For 51 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1928

  • Year Built

    1989

  • $/SqFt

    $244

Schedule your Showing today or click Virtual Tour link to view a video tour. MLS#S5113221. MULTI CHOICE REALTY LLC.

Home For Sale $595,000

Reduced By $30,000

View 1926 Natalen Rd Winter Park FL
View 1926 Natalen Rd Winter Park FL
View 1926 Natalen Rd Winter Park FL
On Market For 54 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1369

  • Year Built

    1957

  • $/SqFt

    $435

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 $799,000

Reduced By $16,000

View 1312 Golfside Dr Winter Park FL
View 1312 Golfside Dr Winter Park FL
View 1312 Golfside Dr Winter Park FL
On Market For 55 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1867

  • Year Built

    1979

  • $/SqFt

    $428

Greenview Winter Pines - Don't miss this opportunity to own a truly exceptional property. Schedule your private tour today! MLS#O6244963. CREEGAN GROUP.

Pended $4,100,000

*POTENTIAL GREAT VALUE
On Market For 54 Days
  • Bedrooms

    5

  • Full Bath(s)

    6

  • 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

On Market For 56 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

On Market For 56 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.

Pended $409,990

On Market For 37 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

On Market For 14 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.

Pended $2,790,000

On Market For 54 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 $535,000

Reduced By $80,000

On Market For 61 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2327

  • Year Built

    1977

  • $/SqFt

    $230

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

Home For Sale $824,999

On Market For 63 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 $694,000

Reduced By $31,000

On Market For 63 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2231

  • Year Built

    1964

  • $/SqFt

    $311

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 $429,000

Reduced By $50,900

*POTENTIAL GREAT VALUE
On Market For 60 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1959

  • $/SqFt

    $224

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 $1,500,000

Reduced By $150,000

*POTENTIAL GREAT VALUE
On Market For 64 Days
  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3446

  • Year Built

    1950

  • $/SqFt

    $435

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 $6,975,000

On Market For 69 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

On Market For 69 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 $815,000

Reduced By $34,995

On Market For 69 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2046

  • Year Built

    1964

  • $/SqFt

    $398

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 $779,900

Reduced By $70,000

On Market For 69 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2200

  • Year Built

    1967

  • $/SqFt

    $355

Come see all that this unique property has to provide! MLS#O6241415. YOUNG REAL ESTATE.

Home For Sale $545,000

Reduced By $25,000

*POTENTIAL GREAT VALUE
On Market For 68 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1970

  • Year Built

    1956

  • $/SqFt

    $277

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 $484,000

Reduced By $5,000

On Market For 68 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1578

  • Year Built

    1972

  • $/SqFt

    $307

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 $468,900

Reduced By $6,100

*POTENTIAL GREAT VALUE
On Market For 69 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2161

  • Year Built

    1969

  • $/SqFt

    $217

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 $1,725,000

Reduced By $73,000

On Market For 57 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2857

  • Year Built

    2024

  • $/SqFt

    $604

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

On Market For 68 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. REAL BROKER, LLC.

Home For Sale $899,900

Reduced By $50,100

On Market For 70 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1861

  • Year Built

    2017

  • $/SqFt

    $484

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 $775,000

Reduced By $50,000

On Market For 70 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2347

  • Year Built

    2003

  • $/SqFt

    $330

Roof - 2024, Hvac - 2021, Plumbing - 2003, Electric - 2003, New Interior Paint 9/2024, New Exterior Paint 9/2024. MLS#O6240342. KELLER WILLIAMS WINTER PARK.

Home For Sale $439,999

Reduced By $15,000

On Market For 70 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1476

  • Year Built

    1974

  • $/SqFt

    $298

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.

Home For Sale $1,650,000

On Market For 71 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 $1,075,000

Reduced By $75,000

On Market For 72 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2011

  • Year Built

    1988

  • $/SqFt

    $535

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

Pended $899,000

Reduced By $80,000

On Market For 68 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 $1,500,000

Reduced By $150,000

On Market For 75 Days
  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2350

  • Year Built

    2024

  • $/SqFt

    $638

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

Pended $375,000

Reduced By $25,000

On Market For 63 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1188

  • Year Built

    1957

  • $/SqFt

    $316

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.

Home For Sale $408,500

Reduced By $11,500

*POTENTIAL GREAT VALUE
On Market For 67 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1477

  • Year Built

    1961

  • $/SqFt

    $277

Temple Terrace - Don’t miss the opportunity to own this move-in-ready home where every detail has been carefully considered. Schedule your private tour today! MLS#O6238372. EQUITYPRO LLC.

Home For Sale $1,999,993

Reduced By $200,006

On Market For 79 Days
  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    3853

  • Year Built

    2012

  • $/SqFt

    $519

Dixie Terrace - Schedule your private showing today and discover what makes this Winter Park home truly exceptional. MLS#O6237975. REALTY ONE GROUP MVP.

Home For Sale $500,000

Reduced By $35,000

On Market For 83 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1692

  • Year Built

    1955

  • $/SqFt

    $296

Fairbanks Shores - No HOA and priced below appraisal! MLS#T3552787. COMMUNITY REALTY ASSOCIATES.

Pended $835,000

On Market For 84 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2449

  • Year Built

    1958

  • $/SqFt

    $341

Embrace the convenience of urban amenities in this fabulous neighborhood, enriched by top-rated schools! MLS#O6237228. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,950,000

Reduced By $200,000

On Market For 73 Days
  • Bedrooms

    3

  • Full Bath(s)

    5

  • Sq. Ft.

    4627

  • Year Built

    1987

  • $/SqFt

    $854

Situated in a top-notch location, just a short distance from vibrant shopping and restaurants on Park Avenue and the iconic Winter Park Golf Course, this home is a rare opportunity to experience the epitome of luxury living in Winter Park. MLS#O6236795. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $649,000

Reduced By $46,000

On Market For 85 Days
  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1162

  • Year Built

    1953

  • $/SqFt

    $559

Ft. with single car garage 1,754 gross square feet Remodeled kitchen and large backyard Winter Park High School A grade school - Elementary and Middle Schools grade B MLS#O6236639. BLUE LIGHTHOUSE REALTY INC.

Home For Sale $474,900

Reduced By $25,100

On Market For 65 Days
  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1851

  • Year Built

    1987

  • $/SqFt

    $257

Autumn Glen - Situated on a generously sized corner lot, this home is zoned for the highly-rated Lake Howell High School and is centrally located to enjoy all that Winter Park has to offer. MLS#O6236929. ORLANDO REALTY & PROPERTY MGNT.

Home For Sale $399,900

Reduced By $40,000

On Market For 86 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1350

  • Year Built

    1958

  • $/SqFt

    $296

Winter Park Estates - Whether you're enjoying a stroll through the neighborhood or unwinding in your private backyard oasis, you'll love coming home to this peaceful paradise. MLS#O6236250. AAA GLOBAL VENTURES PA.

Home For Sale $639,900

Reduced By $10,100

On Market For 87 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1420

  • Year Built

    1963

  • $/SqFt

    $451

Don’t miss the chance to make this your new home – schedule a tour today! MLS#O6222908. NETWORTH REALTY OF ORLANDO, LLC.

Home For Sale $824,900

Reduced By $14,100

On Market For 88 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1961

  • $/SqFt

    $453

Kenilworth Shores - Seller can not close on this home until after 2/1/20225 MLS#O6235113. RAZZANI INTERNATIONAL REALTY.

Home For Sale $3,295,000

On Market For 90 Days
  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4080

  • Year Built

    2024

  • $/SqFt

    $808

Schedule your private tour today to see this stunning property in person! MLS#O6235073. KELLER WILLIAMS WINTER PARK.

Pended $534,000

Reduced By $55,000

On Market For 86 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1874

  • Year Built

    1957

  • $/SqFt

    $285

Kenilworth Shores - Don't miss out—schedule your showing today! MLS#L4946832. PAIGE WAGNER HOMES REALTY.

Home For Sale $349,900

On Market For 90 Days
  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1114

  • Year Built

    1956

  • $/SqFt

    $314

Embrace the charm of yesteryear while enjoying the lifestyle of today at 7102 Easter St. MLS#O6235629. CHARLES RUTENBERG REALTY ORLANDO.

Pended $699,000

Reduced By $50,900

On Market For 87 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1610

  • Year Built

    1950

  • $/SqFt

    $434

Lake Knowles Terrace - This stylish home is move-in ready and invites you to enjoy the best of Winter Park living! MLS#O6234898. FANNIE HILLMAN & ASSOCIATES.

Pended $1,475,000

Reduced By $125,000

On Market For 92 Days
  • Bedrooms

    7

  • Full Bath(s)

    5

  • Sq. Ft.

    5111

  • Year Built

    2015

  • $/SqFt

    $289

This home exudes luxury, style, and comfort, all conveniently located near Winter Park, Oviedo, UCF, and top-rated schools like Trinity Prep, with shopping and dining just a short distance away. MLS#O6234041. ORLANDO REGIONAL REALTY.

Home For Sale $1,050,000

*POTENTIAL GREAT VALUE
On Market For 93 Days
  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1374

  • Year Built

    1971

  • $/SqFt

    $764

(150ft street frontage by 140ft lot depth). MLS#O6232951. DAVEN REAL ESTATE INC.

Home For Sale $1,950,000

Reduced By $49,999

On Market For 85 Days
  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3989

  • Year Built

    2012

  • $/SqFt

    $489

Windsong Elizabeths Walk - Make this exquisite sanctuary your own and indulge in the epitome of luxury living. MLS#O6234031. COMPASS FLORIDA, LLC.

Home For Sale $484,990

*POTENTIAL GREAT VALUE
On Market For 94 Days
  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2300

  • Year Built

    1962

  • $/SqFt

    $211

Eastbrook - Plenty of extra space for storage, large enclosed patio, Great for Entertaining! Lots more extras! MLS#O6233928. LPT REALTY, LLC.

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