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252 Results

View 252 Winter Park Florida Homes for Sale

Home For Sale $1,665,000

Reduced By $25,000

View 1801 Legion Dr Winter Park FL
View Details 57 Photos
View 1801 Legion Dr Winter Park FL
View 1801 Legion Dr Winter Park FL
View 1801 Legion Dr Winter Park FL
On Market For 51 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3518

  • Year Built

    1964

  • $/SqFt

    $473

Green Oaks - Schedule your private tour today and discover the luxury and sophistication of 1801 Legion Dr. MLS#O6199755. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $665,000

Reduced By $30,000

View 1511 Chestnut Ave Winter Park FL
View Details 29 Photos
View 1511 Chestnut Ave Winter Park FL
View 1511 Chestnut Ave Winter Park FL
View 1511 Chestnut Ave Winter Park FL
On Market For 64 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1275

  • Year Built

    1960

  • $/SqFt

    $522

Lake Knowles Terrace - Don't miss out on this fantastic opportunity! MLS#O6199975. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $449,000

View 1929 Houndslake Dr Winter Park FL
View Details 35 Photos
View 1929 Houndslake Dr Winter Park FL
View 1929 Houndslake Dr Winter Park FL
View 1929 Houndslake Dr Winter Park FL
On Market For 28 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1584

  • Year Built

    1982

  • $/SqFt

    $283

Cedar Ridge - The only thing missing from this home is YOU. Schedule your private showing today! MLS#O6199274. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $4,250,000

Reduced By $250,000

View 1228 N Park Ave Winter Park FL
View Details 67 Photos
View 1228 N Park Ave Winter Park FL
View 1228 N Park Ave Winter Park FL
View 1228 N Park Ave Winter Park FL
On Market For 55 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5320

  • Year Built

    2002

  • $/SqFt

    $799

Close to the charming boutiques and restaurants on Park Avenue. MLS#O6199601. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $454,900

Reduced By $15,000
View Details 41 Photos
On Market For 66 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1434

  • Year Built

    1973

  • $/SqFt

    $317

Woodcrest - Past the porch you have a sizable back yard for gardening and or entertaining. Bring your offers! ! MLS#S5103770. LA ROSA REALTY ORLANDO LLC.

Home For Sale $1,995,000

Reduced By $500,000
View Details 48 Photos
On Market For 68 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3154

  • Year Built

    1951

  • $/SqFt

    $633

Schedule you're showing today and experience the epitome of luxury living at 1161 Lincoln Circle." MLS#O6198338. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $775,000

View Details 51 Photos
On Market For 69 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2137

  • Year Built

    2021

  • $/SqFt

    $363

Hawks Crest - Schedule your showing today and prepare to be captivated by the allure of Hawk's Crest living. Measurements are approximately. MLS#T3520666. FLORIDA LUXURY REALTY INC.

Home For Sale $4,250,000

View Details 19 Photos
On Market For 71 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    3660

  • Year Built

    2024

  • $/SqFt

    $1,161

Call now to schedule your meeting with the Builder and get started on your new home! MLS#O6193386. UNITED REAL ESTATE PREFERRED.

Pended $2,995,000

Reduced By $100,000
View Details 61 Photos
On Market For 71 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4216

  • Year Built

    2020

  • $/SqFt

    $710

Comstock Park - Don't miss your opportunity to own a piece of Winter Park's finest. Schedule your private showing today! MLS#O6196961. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $749,900

View Details 42 Photos
On Market For 71 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1370

  • Year Built

    1952

  • $/SqFt

    $547

MLS#O6196093. RE/MAX 200 REALTY.

Home For Sale $589,900

Reduced By $35,100
View Details 29 Photos
On Market For 64 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1946

  • Year Built

    1950

  • $/SqFt

    $303

MLS#S5103315. EXP REALTY LLC.

Pended $589,000

Reduced By $46,000
View Details 18 Photos
On Market For 72 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1376

  • Year Built

    1954

  • $/SqFt

    $428

Orangewood Park - Extra features and updates include: new HVAC 2018, re-piped interior, no cast iron (rare), Roof 2017, replaced well pump for irrigation (low waste water and sewer bills), renovated patio, updated landscape, and renovated guest bathroom. MLS#O6196291. THE KEY REALTY GROUP.

Home For Sale $363,000

Reduced By $22,000
View Details 33 Photos
On Market For 72 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1393

  • Year Built

    1958

  • $/SqFt

    $261

Conveniently located in Winter Park with easy access to shopping, dining, parks, and top-rated schools, you don't want to miss this opportunity! MLS#O6195536. COLDWELL BANKER REALTY.

Home For Sale $1,649,000

Reduced By $143,000
View Details 59 Photos
*POTENTIAL GREAT VALUE
On Market For 74 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3330

  • Year Built

    2017

  • $/SqFt

    $495

Golf and tennis neighborhood Racquet Club, Interlachen Country Club, and Winter Park 9 Golf Course.

MLS#O6194670. KELLY PRICE & COMPANY LLC.

Home For Sale $825,000

Reduced By $174,900
View Details 9 Photos
On Market For 75 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    962

  • Year Built

    1952

  • $/SqFt

    $858

Parklando - This home is near Lake Sue, Leu Gardens, Mead Botanical Gardens and many more gems of Winter Park. MLS#V4935714. GREENE REALTY OF FLORIDA LLC.

Home For Sale $460,000

Reduced By $9,900
View Details 31 Photos
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1969

  • $/SqFt

    $282

Eastbrook - Lot Size is 75' X 110'. MLS#O6195238. ANNE ROGERS REALTY GROUP INC.

Home For Sale $1,250,000

Reduced By $150,000
View Details 11 Photos
On Market For 76 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2100

  • Year Built

    1947

  • $/SqFt

    $595

Charmont - The last time a house sold on this street was four years ago. MLS#V4935671. GREENE REALTY OF FLORIDA LLC.

Home For Sale $6,395,000

Reduced By $600,000
View Details 52 Photos
On Market For 78 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4792

  • Year Built

    1998

  • $/SqFt

    $1,335

Sicilian Shores - Roof and boathouse roof updated 2022. MLS#O6195529. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $748,000

Reduced By $2,000
View Details 36 Photos
On Market For 78 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1669

  • Year Built

    1927

  • $/SqFt

    $448

Lawndale - Welcome to your dream home, where history and modernity live in perfect harmony. MLS#O6195037. BISON REALTY.

Home For Sale $675,000

Reduced By $64,000
View Details 27 Photos
On Market For 78 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2153

  • Year Built

    1977

  • $/SqFt

    $314

This incredible home also boasts an ideal location and with top-rated schools: Lakemont Elementary, Maitland Middle and Winter Park High. MLS#O6194323. COLDWELL BANKER REALTY.

Home For Sale $1,773,000

Reduced By $215,700
View Details 26 Photos
On Market For 81 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2859

  • Year Built

    1948

  • $/SqFt

    $620

Kronenberger - Bedroom Closet Type: Walk-in Closet (Primary Bedroom). MLS#O6193303. FLORIDA PROPERTY LLC.

Pended $1,250,000

Reduced By $245,000
View Details 56 Photos
*POTENTIAL GREAT VALUE
On Market For 81 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3074

  • Year Built

    2017

  • $/SqFt

    $407

Ideally situated near Lakemont Elementary, Publix, Advent Health, and mere minutes from Park Avenue. MLS#O6194226. THE HOPE GROUP.

Home For Sale $1,599,900

Reduced By $95,100
View Details 71 Photos
On Market For 85 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3150

  • Year Built

    2006

  • $/SqFt

    $508

Charmont - Schedule your private showing today before it's SOLD! MLS#O6193582. VOSS REALTY INC.

Pended $995,000

Reduced By $75,000
View Details 52 Photos
On Market For 82 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3057

  • Year Built

    2015

  • $/SqFt

    $325

Schedule a showing today and experience the beauty of this remarkable home! MLS#O6193168. VR HOMES LLC.

Home For Sale $474,900

Reduced By $24,600
View Details 45 Photos
On Market For 86 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1522

  • Year Built

    1964

  • $/SqFt

    $312

What are you waiting for, come check out this home today! MLS#O6190494. KELLER WILLIAMS ADVANTAGE REALTY.

Pended $459,000

View Details 33 Photos
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1671

  • Year Built

    1981

  • $/SqFt

    $275

Cedar Ridge - And if that's not enough...let's not forget this amazing location in Winter Park - easy access to the 417 and 436, close to Trinity Prep and Park Maitland Preschool, and Foxtail Coffee, Kelly's Ice Cream & Donut King right down the street! MLS#O6193153. MEGAN DOWDY REALTY, LLC.

Pended $430,000

Reduced By $29,000
View Details 43 Photos
On Market For 80 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1793

  • Year Built

    1976

  • $/SqFt

    $240

Situated close to shopping, schools, and major roads, you'll enjoy easy access to all the amenities and attractions Central Florida has to offer. MLS#O6191464. WATSON REALTY CORP.

Home For Sale $2,199,999

View Details 67 Photos
On Market For 86 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $554

College Place - With its architectural integrity, handcrafted details, central location, enchanting central skylight, and minutes’ walk to Lake Virginia and Park Avenue, it is a rare find that epitomizes the art of living in sunny Florida. MLS#O6190102. NEXTHOME MY WAY.

Home For Sale $3,890,000

View Details 3 Photos
On Market For 87 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4055

  • Year Built

    2025

  • $/SqFt

    $959

Room Feature: Linen Closet In Bath (Primary Bedroom). MLS#O6191966. CORCORAN PREMIER REALTY.

Home For Sale $2,175,000

Reduced By $25,000
View Details 54 Photos
On Market For 55 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3276

  • Year Built

    1995

  • $/SqFt

    $664

Don't miss your chance to make this exquisite property your own and enjoy the epitome of Florida luxury living. MLS#O6192372. KELLER WILLIAMS WINTER PARK.

Pended $499,900

Reduced By $25,100
View Details 39 Photos
On Market For 88 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1996

  • Year Built

    1966

  • $/SqFt

    $250

Winter Park Estates - Don't miss out on the chance to make it yours! MLS#O6191733. REALTY HUB.

Home For Sale $2,749,000

View Details 61 Photos
On Market For 94 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4692

  • Year Built

    2007

  • $/SqFt

    $586

Zoned for Audubon K-8 and WP High School. MLS#O6190641. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,125,000

Reduced By $175,000
View Details 56 Photos
On Market For 98 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2752

  • Year Built

    1980

  • $/SqFt

    $409

Don't miss out on this rare opportunity—schedule your showing today! MLS#O6189285. COLDWELL BANKER REALTY.

Home For Sale $433,000

Reduced By $14,500
View Details 25 Photos
On Market For 99 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1570

  • Year Built

    1957

  • $/SqFt

    $276

Don't miss the opportunity to make this beautifully updated property your new home sweet home. MLS#O6186742. FLORIDA ONE REAL ESTATE LLC.

Home For Sale $525,000

Reduced By $25,000
View Details 35 Photos
*POTENTIAL GREAT VALUE
On Market For 93 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2197

  • Year Built

    1963

  • $/SqFt

    $239

Don't let this opportunity pass you by, call and arrange for your private showing today! MLS#O6188237. KELLER WILLIAMS WINTER PARK.

Home For Sale $361,000

Reduced By $24,000
View Details 19 Photos
On Market For 69 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1450

  • Year Built

    1980

  • $/SqFt

    $249

Oakcrest - Don't miss out on this fantastic opportunity to make this house your own! MLS#O6189475. OPENDOOR BROKERAGE LLC.

Home For Sale $630,000

Reduced By $40,000
View Details 29 Photos
On Market For 105 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1638

  • Year Built

    1949

  • $/SqFt

    $385

Don’t miss the chance to experience the heartbeat of Winter Park living – schedule your tour today! MLS#O6185063. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $609,900

Reduced By $39,100
View Details 31 Photos
On Market For 106 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2193

  • Year Built

    1954

  • $/SqFt

    $278

Schedule a private tour today and experience luxury living at its finest at 220 Blossom Lane. MLS#O6187877. SUMMERHILL REALTY GROUP LLC.

Home For Sale $500,000

Reduced By $35,000
View Details 44 Photos
On Market For 106 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1878

  • Year Built

    1979

  • $/SqFt

    $266

35 MINUTES FROM DISNEY and 45 MINUTES FROM THE BEACH. MLS#O6186883. RE/MAX 200 REALTY.

Home For Sale $445,000

Reduced By $15,000
View Details 58 Photos
On Market For 106 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1192

  • Year Built

    1949

  • $/SqFt

    $373

Don't miss out on this promising investment opportunity! MLS#O6187138. COLDWELL BANKER REALTY.

Home For Sale $3,150,000

View Details 9 Photos
On Market For 107 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4770

  • Year Built

    2024

  • $/SqFt

    $660

Kenilworth Shores - Don’t miss your opportunity to own this stunning Winter Park home. MLS#O6185001. COMPASS FLORIDA, LLC.

Home For Sale $3,141,000

View Details 10 Photos
On Market For 107 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4188

  • Year Built

    2024

  • $/SqFt

    $750

Charmont - Inquire with the listing agents for further details, and prepare to be captivated by a lifestyle beyond compare. MLS#O6187136. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,960,000

View Details 13 Photos
On Market For 107 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3499

  • Year Built

    2024

  • $/SqFt

    $560

Northwood Terrace - Please inquire with the listing agents for further details. MLS#O6187113. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $729,000

Reduced By $60,000
View Details 27 Photos
On Market For 110 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1715

  • Year Built

    1964

  • $/SqFt

    $425

This home is one of a kind and will not last long. MLS#O6185776. PARK TOWN REAL ESTATE LLC.

Pended $599,900

Reduced By $60,000
View Details 35 Photos
On Market For 99 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    2130

  • Year Built

    1957

  • $/SqFt

    $282

Kenilworth Shores - This gem won't last long...come see it today! MLS#O6185836. SAND DOLLAR REALTY GROUP INC.

Home For Sale $7,370,000

View Details 27 Photos
On Market For 113 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6774

  • Year Built

    2024

  • $/SqFt

    $1,088

Cloister Grove - Please inquire with the list agent for further details. MLS#O6183317. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $780,000

Reduced By $119,999
View Details 41 Photos
On Market For 115 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2447

  • Year Built

    1956

  • $/SqFt

    $319

Winter Park Village - Experience refined living at 2612 Lafayette Avenue — your dream home awaits. MLS#O6183345. EXP REALTY LLC.

Home For Sale $515,000

Reduced By $34,000
View Details 36 Photos
*POTENTIAL GREAT VALUE
On Market For 115 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2188

  • Year Built

    1972

  • $/SqFt

    $235

Arrowhead Cove - Please see MLS for full list of upgrades. MLS#O6185134. AFFINITY REALTY LLC.

Home For Sale $649,900

View Details 23 Photos
On Market For 118 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1553

  • Year Built

    1965

  • $/SqFt

    $418

Howell Heights - Enjoy outdoor entertainment in your Spacious patio and lounge area. Welcome in and be impressed! MLS#O6183727. EMPIRE NETWORK REALTY.

Home For Sale $2,999,000

Reduced By $500,000
View Details 54 Photos
On Market For 120 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    4551

  • Year Built

    1990

  • $/SqFt

    $659

Lugano Terrace - New Windows, both New Water Heaters, New Plumbing and many more. MLS#O6183188. CASTLE REALTY PROFESSIONAL GROUP LLC.

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