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253 Results

View 253 Winter Park Florida Homes for Sale

Home For Sale $515,000

Reduced By $34,000

View 7600 Bent Bow Trl Winter Park FL
View Details 36 Photos
View 7600 Bent Bow Trl Winter Park FL
View 7600 Bent Bow Trl Winter Park FL
View 7600 Bent Bow Trl Winter Park FL
*POTENTIAL GREAT VALUE
On Market For 117 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 2955 Sanbina St Winter Park FL
View Details 23 Photos
View 2955 Sanbina St Winter Park FL
View 2955 Sanbina St Winter Park FL
View 2955 Sanbina St Winter Park FL
On Market For 120 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 1255 Via Lugano Winter Park FL
View Details 54 Photos
View 1255 Via Lugano Winter Park FL
View 1255 Via Lugano Winter Park FL
View 1255 Via Lugano Winter Park FL
On Market For 122 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.

Pended $1,995,000

Reduced By $500,000

View 1362 Richmond Rd Winter Park FL
View Details 45 Photos
View 1362 Richmond Rd Winter Park FL
View 1362 Richmond Rd Winter Park FL
View 1362 Richmond Rd Winter Park FL
On Market For 121 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2925

  • Year Built

    1925

  • $/SqFt

    $682

Virginia Heights - This is the perfect family or forever home. MLS#G5077473. POTOMAC LAND COMPANY.

Home For Sale $414,900

Reduced By $45,000
View Details 25 Photos
*POTENTIAL GREAT VALUE
On Market For 101 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1792

  • Year Built

    1957

  • $/SqFt

    $232

Eastgate - This is the perfect space for both families and investors and is conveniently located walking distance to Lakemont Elementary School and the YMCA. MLS#O6181229. LOKATION.

Home For Sale $539,000

Reduced By $10,000
View Details 9 Photos
On Market For 107 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    1570

  • Year Built

    1948

  • $/SqFt

    $343

Buyer is responsible for doing any research and contacting the city of Winter Park on splits, zoning, building codes, permits, etc. MLS#O6182627. RE/MAX 200 REALTY.

Home For Sale $1,980,000

View Details 50 Photos
On Market For 129 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2857

  • Year Built

    2024

  • $/SqFt

    $693

Lake Killarney Shores - Experience the epitome of luxury living in Winter Park with this exceptional home. MLS#O6181258. SOTERA LIVING.

Home For Sale $1,599,900

Reduced By $150,100
View Details 53 Photos
*POTENTIAL GREAT VALUE
On Market For 130 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4173

  • Year Built

    2019

  • $/SqFt

    $383

Roof - 2018, Hvac (2) - 2018, Plumbing - 2018, Electric - 2018. MLS#O6180799. KELLER WILLIAMS WINTER PARK.

Pended $825,000

Reduced By $23,000
View Details 48 Photos
*POTENTIAL GREAT VALUE
On Market For 90 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2861

  • Year Built

    1925

  • $/SqFt

    $288

Fairbanks Park - It’s truly the best of the best! ! MLS#O6180386. IAD FLORIDA LLC.

Home For Sale $1,500,000

Reduced By $99,000
View Details 73 Photos
*POTENTIAL GREAT VALUE
On Market For 131 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    6252

  • Year Built

    1994

  • $/SqFt

    $240

You will want to show this beauty to your most discriminating Buyers. MLS#O6180611. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $2,195,000

Reduced By $105,000
View Details 53 Photos
*POTENTIAL GREAT VALUE
On Market For 136 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4312

  • Year Built

    2004

  • $/SqFt

    $509

Sylvan Park - Outdoor covered areas including a summer kitchen and a brick fireplace. MLS#O6179257. PREMIER SOTHEBY'S INTL. REALTY.

Pended $2,950,000

Reduced By $200,000
View Details 41 Photos
On Market For 136 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3924

  • Year Built

    2020

  • $/SqFt

    $752

Tuscany Terrace - Bedroom Closet Type: Walk-in Closet (Primary Bedroom). MLS#O6178928. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $480,000

View Details 8 Photos
On Market For 54 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1072

  • Year Built

    1951

  • $/SqFt

    $448

Call us today for a private showing today! MLS#O6178546. MEP REALTY INVESTMENTS LLC.

Home For Sale $945,000

Reduced By $50,000
View Details 46 Photos
On Market For 139 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1829

  • Year Built

    1948

  • $/SqFt

    $517

Zoned R-2 there is no shortage of opportunity for this unique property. MLS#O6178122. KELLY PRICE & COMPANY LLC.

Pended $525,000

View Details 19 Photos
On Market For 82 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1509

  • Year Built

    1958

  • $/SqFt

    $348

Photographs are representative of the property with no furnishings. MLS#O6177655. COLDWELL BANKER REALTY.

Home For Sale $2,295,000

Reduced By $155,000
View Details 84 Photos
On Market For 119 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3989

  • Year Built

    2012

  • $/SqFt

    $575

Windsong Elizabeths Walk -

MLS#O6177110. THE SIMON SIMAAN GROUP.

Pended $1,550,000

Reduced By $450,000
View Details 36 Photos
*POTENTIAL GREAT VALUE
On Market For 130 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3400

  • Year Built

    1992

  • $/SqFt

    $456

Lake Knowles Terrace - SEE ATTATCHMENTS FOR ALL UPGRADES AND FEATURES. http://1540wilbar.website/Video-MLS MLS#O6174985. KELLER WILLIAMS CLASSIC.

Home For Sale $2,300,000

Reduced By $400,000
View Details 65 Photos
*POTENTIAL GREAT VALUE
On Market For 145 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4638

  • Year Built

    2019

  • $/SqFt

    $496

Winter Park Village - Upstairs you will find a large loft with a huge bonus room and 3 large bedrooms each with en-suite bathrooms. MLS#O6172818. KELLER WILLIAMS WINTER PARK.

Home For Sale $2,450,000

Reduced By $150,000
View Details 30 Photos
On Market For 119 Days

  • Bedrooms

    6

  • Full Bath(s)

    5

  • Sq. Ft.

    4182

  • Year Built

    1963

  • $/SqFt

    $586

Lake Knowles Terrace - With its ideal blend of classic charm and modern updates, this fully remodeled residence is a rare find, offering an exceptional opportunity for those seeking a contemporary lifestyle in a sought-after MLS#O6176048. WRA BUSINESS & REAL ESTATE.

Home For Sale $344,000

Reduced By $31,000
View Details 29 Photos
On Market For 150 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1122

  • Year Built

    1954

  • $/SqFt

    $307

Temple Terrace - Don't miss the chance to make this your dream home! MLS#O6175899. OPENDOOR BROKERAGE LLC.

Pended $390,000

Reduced By $35,000
View Details 24 Photos
*POTENTIAL GREAT VALUE
On Market For 152 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1692

  • Year Built

    1958

  • $/SqFt

    $230

Contact Miguel Anastacio and schedule your showing today! MLS#O6174500. COLDWELL BANKER REALTY.

Home For Sale $849,900

Reduced By $75,100
View Details 31 Photos
On Market For 156 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2029

  • Year Built

    1969

  • $/SqFt

    $419

Full list of updates available along with architectural plans to convert 3rd garage into living space. MLS#O6174101. YOU HAVE REALTY LLC.

Home For Sale $2,000,000

Reduced By $400,000
View Details 53 Photos
*POTENTIAL GREAT VALUE
On Market For 157 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4162

  • Year Built

    2007

  • $/SqFt

    $481

Dixie Terrace - *New interior paint throughout! (Not reflected in listing photos) MLS#O6173337. LPT REALTY, LLC.

Home For Sale $1,875,000

View Details 15 Photos
On Market For 158 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2955

  • Year Built

    2024

  • $/SqFt

    $635

Dixie Terrace - Schedule your private showing today and be among the first to experience the charm and luxury of this exceptional residence! MLS#O6172852. CORCORAN PREMIER REALTY.

Home For Sale $5,459,739

Reduced By $40,261
View Details 90 Photos
On Market For 158 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6475

  • Year Built

    2023

  • $/SqFt

    $843

Tuscania - Get one step closer to owning the realization of your dream dwelling experience! MLS#O6173028. LA ROSA REALTY HORIZONS LLC.

Pended $524,900

Reduced By $104,100
View Details 49 Photos
*POTENTIAL GREAT VALUE
On Market For 162 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    2258

  • Year Built

    1948

  • $/SqFt

    $232

Glencoe - Experience the best of Florida living in this inviting abode with endless possibilities. MLS#O6172105. PR REAL ESTATE SERVICES.

Home For Sale $960,000

Reduced By $165,000
View Details 35 Photos
On Market For 171 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2610

  • Year Built

    2013

  • $/SqFt

    $368

Lawndale - The exterior features an epoxy two-car garage with an epoxy flooring, paver driveway & walkway to a fenced backyard with artificial turf that is perfect for children & pets, along with a putting green for the golf enthusiast. MLS#O6168879. COLDWELL BANKER REALTY.

Home For Sale $2,999,999

Reduced By $499,001
View Details 47 Photos
On Market For 176 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5066

  • Year Built

    2013

  • $/SqFt

    $592

Call for your private showing today. MLS#O6166894. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $1,575,000

Reduced By $150,000
View Details 26 Photos
*POTENTIAL GREAT VALUE
On Market For 179 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4021

  • Year Built

    2009

  • $/SqFt

    $392

A-rated Winter Park schools and several excellent private and parochial schools are nearby. MLS#O6167429. BHHS FLORIDA REALTY.

Home For Sale $850,000

Reduced By $145,000
View Details 28 Photos
On Market For 161 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2533

  • Year Built

    1926

  • $/SqFt

    $336

Sylvan Lake Shores - Centrally located to Rollins College and Park Avenue. MLS#O6164933. KELLY PRICE & COMPANY LLC.

Home For Sale $1,599,900

Reduced By $195,100
View Details 42 Photos
On Market For 197 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2651

  • Year Built

    2005

  • $/SqFt

    $604

Comstock Park - Come see this gem before someone snags it first! MLS#O6163891. TAL BUSIDAN PA.

Home For Sale $449,526

Reduced By $35,474
View Details 28 Photos
On Market For 206 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1725

  • Year Built

    1990

  • $/SqFt

    $261

Villas Of Casselberry - Nothing else to do but schedule a tour and call this stunning home yours! MLS#O6162964. COLDWELL BANKER REALTY.

Pended $1,575,000

Reduced By $20,425,000
View Details 40 Photos
*POTENTIAL GREAT VALUE
On Market For 209 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3448

  • Year Built

    2020

  • $/SqFt

    $457

Winter Park Village - Schedule a showing today and experience the epitome of Florida living at 2519 CHANTILLY AVENUE. MLS#O6154620. DALTON WADE INC.

Home For Sale $549,900

Reduced By $30,000
View Details 39 Photos
On Market For 218 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2300

  • Year Built

    1987

  • $/SqFt

    $239

The owner has been meticulous in the maintenance of this home. MLS#O6156969. COLDWELL BANKER REALTY.

Home For Sale $3,300,000

Reduced By $200,000
View Details 59 Photos
On Market For 225 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4325

  • Year Built

    2022

  • $/SqFt

    $763

Virginia Heights - Elevate your everyday in this modern masterpiece that’s not just a home; it’s a statement. MLS#O6157505. CHARLES RUTENBERG REALTY ORLANDO.

Pended $798,000

Reduced By $51,550
View Details 24 Photos
On Market For 227 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2124

  • Year Built

    1958

  • $/SqFt

    $376

Just a comfortable Bicycle Ride and you’ll arrive at Ward park, Babe Ruth Ball Fields, Cady Way Pool, Advent Health Center/Winter Park Hospital, and all that Park Avenue and the Rollins College area has to offer! MLS#O6157948. KELLER WILLIAMS WINTER PARK.

Home For Sale $430,000

Reduced By $65,000
View Details 55 Photos
On Market For 187 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1748

  • Year Built

    1957

  • $/SqFt

    $246

With an Acceptable Offer, Sellers willing to contribute up to $8,000 towards Buyer’s closing costs at closing. MLS#O6157847. COLDWELL BANKER REALTY.

Home For Sale $1,649,000

Reduced By $301,000
View Details 32 Photos
On Market For 231 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3112

  • Year Built

    2005

  • $/SqFt

    $530

This home shows well and is turn key ready due to renovations. MLS#O6157218. COLONIALTOWN REALTY.

Home For Sale $4,130,000

Reduced By $270,000
View Details 64 Photos
On Market For 124 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4635

  • Year Built

    2001

  • $/SqFt

    $891

Virginia Heights - Celebrate nature’s wildlife which range from owls, great white egrets, blue herons, hawks, bunnies, and otters in your private sanctuary minutes to Winter Park’s premier dining, upscale shopping, Mead Botanical Garden, and the highly coveted Audubon K-8, and Winter Park High! MLS#O6152759. STOCKWORTH REALTY GROUP.

Home For Sale $1,695,000

Reduced By $200,000
View Details 31 Photos
On Market For 232 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3341

  • Year Built

    1972

  • $/SqFt

    $507

Currently within the highly sought after Lakemont Elementary, Maitland Middle & Winter Park High school district. MLS#O6154133. COLDWELL BANKER REALTY.

Home For Sale $3,795,000

Reduced By $200,000
View Details 6 Photos
On Market For 243 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4483

  • Year Built

    2024

  • $/SqFt

    $847

The back side of the lot is lined by natural, towering trees, offering plenty of privacy, and the entire yard is the perfect canvas for creating the oasis of your dreams. MLS#O6154240. CORCORAN PREMIER REALTY.

Home For Sale $4,750,000

Reduced By $745,000
View Details 41 Photos
On Market For 155 Days

  • Bedrooms

    5

  • Full Bath(s)

    7

  • Sq. Ft.

    5847

  • Year Built

    1957

  • $/SqFt

    $812

Osceola Shores - All within walking distance to downtown Winter Park and famed Park Avenue… MLS#O6153641. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $484,900

Reduced By $25,100
View Details 16 Photos
*POTENTIAL GREAT VALUE
On Market For 252 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2096

  • Year Built

    1972

  • $/SqFt

    $231

Winter Woods - 3D Virtual Tour: https://my.matterport.com/show/?m=vkek24WbGYM&mls=1. Please call to schedule today! MLS#O6150479. MIGHTY REALTY INC.

Home For Sale $549,000

Reduced By $50,900
View Details 43 Photos
On Market For 67 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1407

  • Year Built

    1964

  • $/SqFt

    $390

Winter Park Pines - All furniture is for sale. Property also listed for rent. MLS#O6140028. VERSALIS REALTY POWERED BY SELLSTATE.

Home For Sale $1,699,000

Reduced By $296,000
View Details 52 Photos
On Market For 266 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3669

  • Year Built

    2007

  • $/SqFt

    $463

One of the few 4 bedroom homes above 3500sqft below $2M in 32789 and it is MOVE IN ready with luxury renovation complete! MLS#O6138358. CHARLES RUTENBERG REALTY ORLANDO.

Pended $562,000

Reduced By $88,000
View Details 45 Photos
On Market For 253 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1778

  • Year Built

    1956

  • $/SqFt

    $316

Tanglewood - Refreshing. Peaceful. Happy. Inviting. Private. Convenient. MLS#O6137445. CADENCE LIFESTYLE REAL ESTATE.

Pended $1,550,000

Reduced By $375,000
View Details 41 Photos
*POTENTIAL GREAT VALUE
On Market For 185 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3401

  • Year Built

    2016

  • $/SqFt

    $456

Contact us today for more information on the assumable mortgage or to schedule a private showing. MLS#O6129924. CORCORAN PREMIER REALTY.

Home For Sale $750,000

View Details 2 Photos
On Market For 337 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1318

  • Year Built

    1948

  • $/SqFt

    $569

Located on the same block as the new 222-unit Seven41 apartment complex, this is a great development opportunity in an ideal Winter Park location. MLS#O6130245. CORCORAN PREMIER REALTY.

Home For Sale $5,400,000

View Details 34 Photos
On Market For 341 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5072

  • Year Built

    2008

  • $/SqFt

    $1,065

Maitland Shores - The property is zoned for A-rated Dommerich Elementary, Maitland Middle School, and Winter Park High School. MLS#O6120809. COMPASS FLORIDA LLC.

Pended $824,900

Reduced By $99,100
View Details 37 Photos
On Market For 149 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1930

  • Year Built

    2021

  • $/SqFt

    $427

Room Feature: Linen Closet In Bath (Primary Bedroom). MLS#O6120134. LPT REALTY, LLC.

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