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View 240 Winter Park Florida Homes for Sale

Pended $4,250,000

View 1229 Via Del Mar Winter Park FL
View Details 67 Photos
View 1229 Via Del Mar Winter Park FL
View 1229 Via Del Mar Winter Park FL
View 1229 Via Del Mar Winter Park FL
On Market For 23 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 660 Arjay Way Winter Park FL
View Details 25 Photos
View 660 Arjay Way Winter Park FL
View 660 Arjay Way Winter Park FL
View 660 Arjay Way Winter Park FL
On Market For 24 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 345 Sylvan Blvd Winter Park FL
View Details 58 Photos
View 345 Sylvan Blvd Winter Park FL
View 345 Sylvan Blvd Winter Park FL
View 345 Sylvan Blvd Winter Park FL
On Market For 25 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 1762 Chestnut Ave Winter Park FL
View Details 28 Photos
View 1762 Chestnut Ave Winter Park FL
View 1762 Chestnut Ave Winter Park FL
View 1762 Chestnut Ave Winter Park FL
On Market For 27 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 28 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 29 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 29 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 29 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 $549,999

Reduced By $20,000
View Details 25 Photos
On Market For 30 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1128

  • Year Built

    1954

  • $/SqFt

    $488

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

Pended $405,000

View Details 39 Photos
On Market For 30 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.

Home For Sale $389,900

Reduced By $10,100
View Details 31 Photos
On Market For 21 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1188

  • Year Built

    1957

  • $/SqFt

    $328

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.

Pended $1,750,000

View Details 39 Photos
On Market For 30 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3620

  • Year Built

    2024

  • $/SqFt

    $483

Kenilworth Shores - the convenience of nearby parks, trails, and the cultural charm of Park Avenue, all while residing in a neighborhood that the luxury of Winter Park’s finest without the premium zip code. MLS#O6238423. BEYCOME OF FLORIDA LLC.

Pended $579,000

View Details 12 Photos
On Market For 31 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1000

  • Year Built

    1949

  • $/SqFt

    $579

Just minutes from top schools, shopping, and dining, this location offers both convenience and the chance to design your perfect oasis. MLS#O6237786. LAND & NESTS.

Home For Sale $420,000

View Details 32 Photos
On Market For 24 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1477

  • Year Built

    1961

  • $/SqFt

    $284

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.

Pended $415,000

View Details 42 Photos
On Market For 30 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1560

  • Year Built

    1980

  • $/SqFt

    $266

Wrenwood Heights - Four point updates include: Roof 2021, HVAC 2015, Plumbing 2016 and new Electrical Panel in 2014. MLS#O6237439. MAINFRAME REAL ESTATE.

Home For Sale $2,199,999

View Details 89 Photos
On Market For 32 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    3853

  • Year Built

    2012

  • $/SqFt

    $571

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

Pended $1,395,000

View Details 40 Photos
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2550

  • Year Built

    1958

  • $/SqFt

    $547

Kronenberger - * Please ask for a floor plan, list of improvements, and click on the Matterport link for a virtual tour! MLS#O6237992. FANNIE HILLMAN & ASSOCIATES.

Pended $489,000

View Details 39 Photos
On Market For 32 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1720

  • Year Built

    1982

  • $/SqFt

    $284

Wrenwood Heights - Don’t miss this opportunity to own a beautifully updated home in a sought-after neighborhood! MLS#O6238364. RE/MAX PRIME PROPERTIES.

Home For Sale $515,000

Reduced By $20,000
View Details 23 Photos
On Market For 36 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1692

  • Year Built

    1955

  • $/SqFt

    $304

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

Pended $374,000

Reduced By $5,000
View Details 21 Photos
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1516

  • Year Built

    1966

  • $/SqFt

    $247

Schedule your showing today and discover all the opportunity this wonderful property has! MLS#O6236348. ALL REAL ESTATE & INVESTMENTS.

Pended $835,000

View Details 15 Photos
On Market For 37 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 $637,900

Reduced By $22,000
View Details 48 Photos
On Market For 36 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2366

  • Year Built

    1994

  • $/SqFt

    $270

Quail Run - This exquisite home is a rare find and won’t last long, schedule your private showing today! MLS#O6236970. FANNIE HILLMAN & ASSOCIATES.

Pended $379,900

View Details 43 Photos
*POTENTIAL GREAT VALUE
On Market For 37 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1878

  • Year Built

    1954

  • $/SqFt

    $202

Temple Terrace - Unbelievable value for a home of this size in a premium location! MLS#S5111370. ORLANDO PREMIUM PROPERTIES LLC.

Home For Sale $3,950,000

Reduced By $200,000
View Details 38 Photos
On Market For 37 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
View Details 29 Photos
On Market For 38 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.

Pended $515,000

View Details 30 Photos
On Market For 38 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1560

  • Year Built

    1966

  • $/SqFt

    $330

Convenient to the 417, fantastic shopping, dining, top rated Orange County schools and steps away from the Cady Way Trail. MLS#O6231321. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $475,000

Reduced By $25,000
View Details 34 Photos
On Market For 37 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1800

  • Year Built

    1987

  • $/SqFt

    $264

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.

Pended $394,400

View Details 28 Photos
On Market For 33 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1263

  • Year Built

    1966

  • $/SqFt

    $312

NO HOA & oversized lot provide the perfect opportunity to call 2042 Cocos Court HOME! MLS#O6235801. FANNIE HILLMAN & ASSOCIATES.

Pended $799,000

View Details 1 Photo
*POTENTIAL GREAT VALUE
On Market For 19 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2747

  • Year Built

    1953

  • $/SqFt

    $291

Northwood Terrace - This neighborhood is truly a gem zoned for Audubon K-8 and Winter Park High school in an area undergoing rapid transition due to the location and the quality of schools. MLS#O6224470. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $439,900

View Details 15 Photos
On Market For 39 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1350

  • Year Built

    1958

  • $/SqFt

    $326

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 $650,000

View Details 40 Photos
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1420

  • Year Built

    1963

  • $/SqFt

    $458

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

Pended $4,350,000

View Details 37 Photos
On Market For 35 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5527

  • Year Built

    1997

  • $/SqFt

    $787

Tuscania - This magnificent residence is just footsteps from the Winter Park Racquet Club and 5 minutes from Interlachen Country Club as well as the upscale shops and restaurants of Park Avenue… This is truly a unique opportunity to purchase a like-new, current design “like new” home offering an unparalleled lifestyle in one of Winter Park's most desirable addresses! ! MLS#O6235491. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $824,900

Reduced By $14,100
View Details 58 Photos
On Market For 42 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1961

  • $/SqFt

    $453

Kenilworth Shores - Transferable Sentracon system.Easy show and a must see! PRICED below appraised value! MLS#O6235113. RAZZANI INTERNATIONAL REALTY.

Home For Sale $3,295,000

View Details 18 Photos
On Market For 43 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4080

  • Year Built

    1958

  • $/SqFt

    $808

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

Pended $1,039,000

Reduced By $36,000
View Details 43 Photos
On Market For 42 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1366

  • Year Built

    1958

  • $/SqFt

    $761

South Lakemont Shores - Roof will be replaced prior to closing, with buyer choosing color of shingles! MLS#O6234514. FLORIDA REALTY INVESTMENTS.

Home For Sale $549,000

Reduced By $40,000
View Details 36 Photos
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1874

  • Year Built

    1957

  • $/SqFt

    $293

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

Home For Sale $529,900

Reduced By $20,100
View Details 20 Photos
*POTENTIAL GREAT VALUE
On Market For 43 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1920

  • Year Built

    1981

  • $/SqFt

    $276

It can also be used as a duplex for 1 bedroom 1 bathroom with living room at downstairs and 2 bed 2 bath with family room at upstairs and kitchen at outside porch. MLS#O6235531. AAA GLOBAL VENTURES PA.

Home For Sale $349,900

View Details 24 Photos
On Market For 43 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 $1,349,000

View Details 73 Photos
On Market For 44 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4468

  • Year Built

    2021

  • $/SqFt

    $302

Waters Edge At Hawks Crest - Put in your paddle board, kayak or just enjoy the wonderful sunsets from the fishing dock. MLS#S5110981. HAMILTON REALTY.

Pended $1,178,000

View Details 55 Photos
*POTENTIAL GREAT VALUE
On Market For 27 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3381

  • Year Built

    1992

  • $/SqFt

    $348

& Sanford Airports & easy access to SR417. MLS#O6233722. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $749,900

View Details 27 Photos
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1610

  • Year Built

    1950

  • $/SqFt

    $466

Lake Knowles Terrace - Whether you enjoy hosting guests or simply relaxing in your own oasis, this home provides you with a comfortable and stylish lifestyle in one of Winter Park's most desirable neighborhoods. MLS#O6234898. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $1,475,000

Reduced By $125,000
View Details 91 Photos
*POTENTIAL GREAT VALUE
On Market For 46 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 $1,250,000

View Details 42 Photos
*POTENTIAL GREAT VALUE
On Market For 46 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2998

  • Year Built

    2023

  • $/SqFt

    $417

Elizabeth Heights - Don’t miss this rare opportunity to own a one-of-a-kind residence in Winter Park! MLS#O6233766. EXP REALTY LLC.

Home For Sale $1,050,000

View Details 5 Photos
*POTENTIAL GREAT VALUE
On Market For 46 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 $1,999,999

View Details 87 Photos
On Market For 38 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3989

  • Year Built

    2012

  • $/SqFt

    $501

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

View Details 37 Photos
*POTENTIAL GREAT VALUE
On Market For 47 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.

Home For Sale $799,500

Reduced By $25,500
View Details 31 Photos
On Market For 50 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2441

  • Year Built

    1967

  • $/SqFt

    $328

Don’t miss your chance to own this exceptional Winter Park Hills home where comfort, style and practicality come together in harmony. MLS#O6232937. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $635,000

Reduced By $14,900
View Details 41 Photos
On Market For 36 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1716

  • Year Built

    1932

  • $/SqFt

    $370

Lawndale - Don't miss your opportunity to own your piece of Winter Park. Schedule your private showing today. MLS#O6233039. COLDWELL BANKER RESIDENTIAL RE.

Pended $379,000

Reduced By $16,000
View Details 28 Photos
On Market For 50 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1258

  • Year Built

    1984

  • $/SqFt

    $301

Springview - Don't pass up on this one, schedule a showing today. MLS#O6233516. ONE45 REALTY LLC.

Home For Sale $354,900

Reduced By $10,100
View Details 22 Photos
On Market For 50 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1162

  • Year Built

    1954

  • $/SqFt

    $305

Fairbanks Shores - Seller will contribute $5000 toward buyer's closing costs and/or rate buydown. MLS#O6233435. COLDWELL BANKER RESIDENTIAL RE.

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