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245 Results

View 245 Winter Park Florida Homes for Sale

Pended $2,650,000

Reduced By $100,000

View 350 E Reading Way Winter Park FL
View Details 54 Photos
View 350 E Reading Way Winter Park FL
View 350 E Reading Way Winter Park FL
View 350 E Reading Way Winter Park FL
On Market For 87 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4693

  • Year Built

    2017

  • $/SqFt

    $565

Charmont - Excellent K-8 Audubon Park School and Winter Park High School. MLS#O6213583. FANNIE HILLMAN & ASSOCIATES.

Pended $649,000

Reduced By $51,000

View 1299 Grand Rd Winter Park FL
View Details 16 Photos
View 1299 Grand Rd Winter Park FL
View 1299 Grand Rd Winter Park FL
View 1299 Grand Rd Winter Park FL
On Market For 79 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1248

  • Year Built

    1927

  • $/SqFt

    $520

2 Lots - 1297 and 1299 being sold as bundle. MLS#O6213932. MARGAUX REALTY INC.

Home For Sale $5,695,000

View 698 N New York Ave Winter Park FL
View Details 3 Photos
View 698 N New York Ave Winter Park FL
View 698 N New York Ave Winter Park FL
On Market For 89 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    5096

  • Year Built

    2025

  • $/SqFt

    $1,118

Price is subject to change through construction. MLS#O6211406. CORCORAN PREMIER REALTY.

Pended $1,990,000

Reduced By $210,000

View 2816 Norris Ave Winter Park FL
View Details 36 Photos
View 2816 Norris Ave Winter Park FL
View 2816 Norris Ave Winter Park FL
View 2816 Norris Ave Winter Park FL
On Market For 90 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3880

  • Year Built

    2019

  • $/SqFt

    $513

Lake Forest Park - Perfect home to raise a family walking distance to Kellys ice cream shop, Salty Donuts, and Audubon Park k9. MLS#O6212649. BALDWIN PARK REALTY LLC.

Home For Sale $7,500,000

Reduced By $499,999
View Details 99 Photos
*POTENTIAL GREAT VALUE
On Market For 93 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7916

  • Year Built

    1996

  • $/SqFt

    $947

Kronenberger -

MLS#O6212012. IRON VALLEY REAL ESTATE CENTRAL FLORIDA.

Home For Sale $1,550,000

Reduced By $125,000
View Details 41 Photos
On Market For 93 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3068

  • Year Built

    1956

  • $/SqFt

    $505

All Double Pane Aluminum Windows throughout home. MLS#O6212814. LPT REALTY.

Home For Sale $5,500,000

View Details 42 Photos
On Market For 56 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    5636

  • Year Built

    2024

  • $/SqFt

    $976

Comstock Park - Close to ICC, WPRC, Phelps Park/YMCA and Park Avenue. MLS#O6209613. PREMIER SOTHEBY'S INTL. REALTY.

Pended $473,900

Reduced By $26,000
View Details 44 Photos
On Market For 93 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1990

  • Year Built

    1989

  • $/SqFt

    $238

Don't miss your chance to make this house your new home. MLS#O6204283. KELLER WILLIAMS ADVANTAGE REALTY.

Pended $389,000

View Details 24 Photos
*POTENTIAL GREAT VALUE
On Market For 95 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1442

  • Year Built

    1955

  • $/SqFt

    $270

Albert Lee Ridge - For more information or to schedule a private showing, contact us today. MLS#O6210454. LPT REALTY.

Home For Sale $625,000

Reduced By $63,000
View Details 48 Photos
On Market For 58 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2093

  • Year Built

    1979

  • $/SqFt

    $299

Greenview Winter Pines - Don't miss your chance to experience this captivating home firsthand - schedule your private showing today. MLS#O6211471. CORCORAN PREMIER REALTY.

Pended $489,900

View Details 37 Photos
On Market For 42 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1755

  • Year Built

    1981

  • $/SqFt

    $279

Wrenwood Heights - Formal living & dining areas, separate family room, 3 way split bedroom plan, The PERFECT location convenient to shopping, dining, main roads. WELCOME HOME! MLS#S5106049. WEICHERT REALTORS HALLMARK PRO.

Home For Sale $440,000

Reduced By $35,000
View Details 22 Photos
*POTENTIAL GREAT VALUE
On Market For 95 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2038

  • Year Built

    1982

  • $/SqFt

    $216

Cedar Ridge - Close to shopping, dining and entertainment, this home blends comfort and style, providing an ideal setting for both everyday living and special occasions. MLS#O6210978. MARK SPAIN REAL ESTATE.

Pended $380,000

View Details 12 Photos
On Market For 21 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    899

  • Year Built

    1925

  • $/SqFt

    $423

Don’t miss this opportunity to own a piece of this exclusive community.. . MLS#O6210271. LA ROSA REALTY ORLANDO LLC.

Home For Sale $3,500,000

Reduced By $800,000
View Details 68 Photos
On Market For 97 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4338

  • Year Built

    1970

  • $/SqFt

    $807

Timberlane Shores - This is an incredible opportunity to live in the existing home, remodel or build your own on the Winter Park Chain of Lakes. MLS#O6207007. PARK 26 REALTY LLC.

Home For Sale $357,000

Reduced By $42,900
View Details 25 Photos
On Market For 98 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1340

  • Year Built

    1986

  • $/SqFt

    $266

Temple Terrace - Make this charming home yours today and experience the best of Winter Park living at an amazing price. MLS#O6210685. FATHOM REALTY FL LLC.

Pended $2,095,000

Reduced By $355,000
View Details 65 Photos
On Market For 101 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3669

  • Year Built

    1979

  • $/SqFt

    $571

Call today for your private viewing of this pristine, well loved Sevilla home. MLS#O6209249. FANNIE HILLMAN & ASSOCIATES.

Pended $685,000

Reduced By $40,000
View Details 82 Photos
On Market For 95 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1770

  • Year Built

    2021

  • $/SqFt

    $387

Park Maitland Preschool, Kelly's Ice Cream and Foxtail Coffee are located at the front of the neighborhood for added convenience. MLS#O6210192. LPT REALTY.

Home For Sale $1,295,000

Reduced By $90,000
View Details 57 Photos
On Market For 103 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2306

  • Year Built

    1966

  • $/SqFt

    $562

Green Oaks - With its desirable single-story layout, large outdoor space, and a corner lot, this ranch-style home offers a blend of comfort and functionality for today's lifestyle. MLS#O6209075. KELLY PRICE & COMPANY LLC.

Home For Sale $815,000

Reduced By $10,000
View Details 44 Photos
On Market For 103 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2637

  • Year Built

    2019

  • $/SqFt

    $309

Preserve At Hawks Crest - This exclusive residence offers a refined lifestyle for those who appreciate peaceful and convenient living, blending luxury, comfort, and community into one perfect package. MLS#O6208471. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $489,995

Reduced By $34,504
View Details 46 Photos
On Market For 103 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1932

  • Year Built

    1971

  • $/SqFt

    $254

Don’t miss your opportunity to own this incredible home; schedule a showing today and make your dream of Winter Park living a reality! MLS#O6209190. EXP REALTY LLC.

Home For Sale $1,795,000

Reduced By $190,000
View Details 43 Photos
On Market For 108 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4133

  • Year Built

    2021

  • $/SqFt

    $434

Schedule a private viewing today and experience the epitome of luxury living near Park Ave. MLS#O6208366. COLDWELL BANKER REALTY.

Home For Sale $419,000

Reduced By $30,000
View Details 22 Photos
On Market For 90 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1645

  • Year Built

    1983

  • $/SqFt

    $255

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

Home For Sale $6,800,000

Reduced By $450,000
View Details 72 Photos
On Market For 101 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4581

  • Year Built

    1934

  • $/SqFt

    $1,484

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 $2,495,000

Reduced By $300,000
View Details 63 Photos
On Market For 114 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    4500

  • Year Built

    2024

  • $/SqFt

    $554

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 $400,000

View Details 24 Photos
On Market For 114 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1627

  • Year Built

    1961

  • $/SqFt

    $246

Eastbrook - Use it for your closing costs or to lower your interest rate. Schedule your private showing today! MLS#O6206562. FLOBELLA REALTY LLC.

Pended $1,790,000

Reduced By $105,000
View Details 64 Photos
On Market For 92 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3423

  • Year Built

    2014

  • $/SqFt

    $523

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 $595,000

Reduced By $44,000
View Details 65 Photos
*POTENTIAL GREAT VALUE
On Market For 115 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2407

  • Year Built

    1953

  • $/SqFt

    $247

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 107 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.

Pended $1,275,000

Reduced By $75,000
View Details 71 Photos
On Market For 111 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2688

  • Year Built

    2004

  • $/SqFt

    $474

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 101 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 $4,650,000

Reduced By $550,000
View Details 33 Photos
On Market For 121 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5681

  • Year Built

    1985

  • $/SqFt

    $819

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 121 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 $929,000

Reduced By $71,000
View Details 19 Photos
*POTENTIAL GREAT VALUE
On Market For 121 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3902

  • Year Built

    1969

  • $/SqFt

    $238

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 $2,750,000

Reduced By $375,000
View Details 48 Photos
On Market For 101 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3576

  • Year Built

    2007

  • $/SqFt

    $769

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 $1,795,000

Reduced By $100,000
View Details 49 Photos
On Market For 117 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3217

  • Year Built

    1952

  • $/SqFt

    $558

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 $1,778,000

Reduced By $72,000
View Details 72 Photos
On Market For 123 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3478

  • Year Built

    2003

  • $/SqFt

    $511

Dixie Terrace -

MLS#O6200787. HOMEVEST REALTY.

Home For Sale $370,000

Reduced By $28,990
View Details 43 Photos
*IS SHORT SALE
On Market For 124 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1160

  • Year Built

    1957

  • $/SqFt

    $319

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

Home For Sale $825,000

Reduced By $90,000
View Details 60 Photos
On Market For 125 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2548

  • Year Built

    1940

  • $/SqFt

    $324

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 $419,900

Reduced By $19,100
View Details 32 Photos
On Market For 128 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1512

  • Year Built

    1967

  • $/SqFt

    $278

MLS#O6194293. BEAR TEAM REAL ESTATE.

Pended $1,735,000

Reduced By $160,000
View Details 40 Photos
On Market For 127 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3361

  • Year Built

    2007

  • $/SqFt

    $516

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 $350,000

Reduced By $70,000
View Details 34 Photos
On Market For 128 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    987

  • Year Built

    1956

  • $/SqFt

    $355

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

Home For Sale $515,000

Reduced By $53,000
View Details 48 Photos
On Market For 129 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1970

  • $/SqFt

    $268

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 $11,795,000

View Details 48 Photos
*POTENTIAL GREAT VALUE
On Market For 132 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.

Pended $434,000

Reduced By $15,000
View Details 39 Photos
On Market For 91 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1584

  • Year Built

    1982

  • $/SqFt

    $274

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 $427,900

Reduced By $42,000
View Details 41 Photos
On Market For 135 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1434

  • Year Built

    1973

  • $/SqFt

    $298

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 $4,250,000

View Details 19 Photos
On Market For 142 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.

Home For Sale $550,000

Reduced By $75,000
View Details 39 Photos
*POTENTIAL GREAT VALUE
On Market For 131 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1946

  • Year Built

    1950

  • $/SqFt

    $283

MLS#S5103315. EXP REALTY LLC.

Home For Sale $1,590,000

Reduced By $202,000
View Details 65 Photos
On Market For 146 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3330

  • Year Built

    2017

  • $/SqFt

    $477

Doctors love this neighborhood – minutes form Advent Health. Ready for move-in immediately! MLS#O6194670. KELLY PRICE & COMPANY LLC.

Home For Sale $949,000

Reduced By $451,000
View Details 11 Photos
On Market For 127 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2100

  • Year Built

    1947

  • $/SqFt

    $452

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

Pended $5,750,000

Reduced By $1,245,000
View Details 52 Photos
On Market For 147 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4792

  • Year Built

    1998

  • $/SqFt

    $1,200

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

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