218 Results

View 218 Winter Park Florida Homes for Sale

Home For Sale $2,200,000

Reduced By $200,000

View 1130 Kenwood Ave Winter Park FL
View Details 53 Photos
View 1130 Kenwood Ave Winter Park FL
View 1130 Kenwood Ave Winter Park FL
View 1130 Kenwood Ave Winter Park FL
On Market For 150 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4162

  • Year Built

    2007

  • $/SqFt

    $529

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

Pended $1,400,000

Reduced By $200,000

View 313 Sylvan Dr Winter Park FL
View Details 24 Photos
View 313 Sylvan Dr Winter Park FL
View 313 Sylvan Dr Winter Park FL
View 313 Sylvan Dr Winter Park FL
On Market For 83 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2525

  • Year Built

    1915

  • $/SqFt

    $554

Sylvan Park - This property offers sweeping views of Lake Sylvan and is a peaceful and tranquil location. MLS#O6173279. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,875,000

View 1101 Kenwood Ave Winter Park FL
View Details 12 Photos
View 1101 Kenwood Ave Winter Park FL
View 1101 Kenwood Ave Winter Park FL
View 1101 Kenwood Ave Winter Park FL
On Market For 88 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 $489,900

Reduced By $35,100

View 7688 Bent Bow Trl Winter Park FL
View Details 57 Photos
View 7688 Bent Bow Trl Winter Park FL
View 7688 Bent Bow Trl Winter Park FL
View 7688 Bent Bow Trl Winter Park FL
On Market For 86 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1906

  • Year Built

    1971

  • $/SqFt

    $257

Arrowhead Cove - Call TODAY for your PRIVATE viewing – it won’t last long! MLS#O6172555. CREEGAN GROUP.

Home For Sale $5,566,500

View Details 90 Photos
On Market For 87 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6475

  • Year Built

    2023

  • $/SqFt

    $860

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

Pended $395,000

Reduced By $2,500
View Details 21 Photos
On Market For 70 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1238

  • Year Built

    1960

  • $/SqFt

    $319

Eastbrook - Schedule your tour today and envision the possibilities that await in this truly remarkable home! MLS#O6171603. WRA BUSINESS & REAL ESTATE.

Home For Sale $375,000

Reduced By $10,000
View Details 14 Photos
On Market For 87 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1126

  • Year Built

    1985

  • $/SqFt

    $333

Country Lane - Desirable location with easy access to shopping and restaurants on Red Butg Lake Road/Mitchell Hammock and minutes from SR417 to anywhere! MLS#O6172885. MCGRATH MANAGEMENT, INC..

Home For Sale $549,000

Reduced By $80,000
View Details 49 Photos
*POTENTIAL GREAT VALUE
On Market For 91 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2258

  • Year Built

    1948

  • $/SqFt

    $243

Glencoe - The Property Is Located Near The Quaint Shopping And Dining Area Or Winter Park Close To Interstate Shopping Dining And Local Attractions MLS#O6172105. PR REAL ESTATE SERVICES.

Pended $550,000

View Details 41 Photos
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1917

  • Year Built

    1977

  • $/SqFt

    $287

Lake Waunatta Woods - The location of the home provides convenient traveling to multiple grocery stores, State Road 417, the University of Central Florida, Full Sail University, downtown Winter Park, and Downtown Orlando! MLS#O6171602. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $700,000

Reduced By $75,000
View Details 41 Photos
On Market For 95 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2416

  • Year Built

    2022

  • $/SqFt

    $290

Hawks Crest - An exclusive respite, this home exemplifies a refined lifestyle for those who appreciate peaceful and convenient living. MLS#O6168951. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,995,000

Reduced By $300,000
View Details 70 Photos
On Market For 83 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4308

  • Year Built

    2004

  • $/SqFt

    $463

Windsong Elizabeths Walk - Don't miss the opportunity to make this exceptional house your new home. MLS#O6168950. CORCORAN PREMIER REALTY.

Home For Sale $999,999

Reduced By $125,001
View Details 35 Photos
On Market For 110 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2610

  • Year Built

    2013

  • $/SqFt

    $383

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 $569,900

Reduced By $10,000
View Details 26 Photos
On Market For 101 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2279

  • Year Built

    1965

  • $/SqFt

    $250

Winter Park Estates - Come and view this beautifully remodeled home in the Winter Park area. MLS#T3496399. PAULINO GLOBAL REAL ESTATE.

Home For Sale $2,295,000

Reduced By $100,000
View Details 33 Photos
On Market For 100 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4435

  • Year Built

    2019

  • $/SqFt

    $517

Conveniently minutes from Park Avenue, Winter Park Hospital and Rollins College, this home is a must-see! MLS#O6169205. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,299,000

Reduced By $196,000
View Details 61 Photos
*POTENTIAL GREAT VALUE
On Market For 108 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4364

  • Year Built

    1968

  • $/SqFt

    $298

Indulge in the grandeur and privacy of this Winter Park gem, where every detail is a testament to luxury and comfort. MLS#O6168515. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,495,000

Reduced By $30,000
View Details 49 Photos
On Market For 31 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3634

  • Year Built

    2007

  • $/SqFt

    $411

Conwill Estates - Please see the attachments for the floorplan, list of updates, and more! MLS#O6168352. FANNIE HILLMAN & ASSOCIATES.

Pended $424,900

View Details 30 Photos
On Market For 77 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1988

  • $/SqFt

    $261

Bridgewater - Great Seminole County schools!Don’t Miss This One! MLS#O6168210. MARK SPAIN REAL ESTATE.

Home For Sale $3,199,000

Reduced By $300,000
View Details 55 Photos
On Market For 106 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    5066

  • Year Built

    2013

  • $/SqFt

    $631

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

Home For Sale $2,755,000

View Details 35 Photos
On Market For 106 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4000

  • Year Built

    2023

  • $/SqFt

    $689

Just completed in 2024, this home is ready for the most discerning buyer. MLS#O6168201. KELLER WILLIAMS WINTER PARK.

Pended $1,995,000

Reduced By $295,000
View Details 66 Photos
On Market For 85 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3703

  • Year Built

    1997

  • $/SqFt

    $539

Lake Knowles Terrace - Don't miss the chance to make this your forever home! MLS#O6167155. CORCORAN PREMIER REALTY.

Home For Sale $1,639,000

Reduced By $86,000
View Details 26 Photos
On Market For 108 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4021

  • Year Built

    2009

  • $/SqFt

    $408

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

Home For Sale $1,290,000

Reduced By $160,000
View Details 24 Photos
On Market For 115 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3082

  • Year Built

    2002

  • $/SqFt

    $419

Greenview Winter Pines - It is approximately 4 miles to Rollins College and 8 miles to the University of Central Florida. MLS#O6165834. BENNETT PROPERTY GROUP, LLC.

Home For Sale $899,000

Reduced By $96,000
View Details 28 Photos
On Market For 122 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2533

  • Year Built

    1926

  • $/SqFt

    $355

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

Home For Sale $369,000

Reduced By $30,000
View Details 24 Photos
On Market For 124 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1242

  • Year Built

    1954

  • $/SqFt

    $297

Temple Terrace - Back on Market and ready to move quick! MLS#O6165035. LEERDAM PROPERTIES INC..

Pended $1,299,900

View Details 1 Photo
On Market For 1 Day

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3252

  • Year Built

    2024

  • $/SqFt

    $400

Lawndale - Make an appointment to see this beautiful home today. MLS#O6164039. RE/MAX EXCLUSIVE COLLECTION.

Home For Sale $1,699,900

Reduced By $95,100
View Details 37 Photos
On Market For 129 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2651

  • Year Built

    2005

  • $/SqFt

    $641

Comstock Park - Come see this gem before someone snags it first! MLS#O6163891. PREFERRED REALTY OF FLORIDA.

Pended $410,000

View Details 46 Photos
On Market For 106 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1419

  • Year Built

    1966

  • $/SqFt

    $289

Come and see what this great central Florida community has to offer! MLS#O6162405. GALLOWAY REAL ESTATE.

Home For Sale $449,526

Reduced By $35,474
View Details 28 Photos
On Market For 134 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.

Home For Sale $1,999,000

Reduced By $501,000
View Details 68 Photos
*POTENTIAL GREAT VALUE
On Market For 139 Days

  • Bedrooms

    7

  • Full Bath(s)

    6

  • Sq. Ft.

    6854

  • Year Built

    2003

  • $/SqFt

    $292

Lugano Terrace - Please ask for a measured floor plan to explore every detail of this extraordinary home. MLS#O6161682. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,699,000

Reduced By $20,301,000
View Details 50 Photos
On Market For 139 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3448

  • Year Built

    2020

  • $/SqFt

    $493

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 $1,599,900

Reduced By $200,000
View Details 35 Photos
On Market For 141 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2560

  • Year Built

    1958

  • $/SqFt

    $625

Very possibly it will be "Love at First Sight"! MLS#O6161030. J. SCOTT JONES, REALTOR.

Home For Sale $569,900

Reduced By $10,000
View Details 39 Photos
On Market For 147 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2300

  • Year Built

    1987

  • $/SqFt

    $248

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

Home For Sale $599,999

View Details 34 Photos
On Market For 150 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2340

  • Year Built

    1971

  • $/SqFt

    $256

Arrowhead Cove - Experience peace of mind with a newer roof (2017), new cabinets, new flooring, new plumbing, new AC ducts, and new electrical throughout the entire home. MLS#O6159358. PARK PLACE REAL ESTATE.

Home For Sale $3,500,000

View Details 59 Photos
On Market For 158 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4325

  • Year Built

    2022

  • $/SqFt

    $809

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.

Home For Sale $7,250,000

View Details 55 Photos
*POTENTIAL GREAT VALUE
On Market For 157 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    9075

  • Year Built

    2021

  • $/SqFt

    $799

Don’t miss your opportunity to own one of Winter Parks most remarkable residences. MLS#O6156666. COMPASS FLORIDA, LLC.

Home For Sale $808,000

Reduced By $41,550
View Details 24 Photos
On Market For 156 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2124

  • Year Built

    1958

  • $/SqFt

    $380

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 $445,900

Reduced By $49,100
View Details 55 Photos
On Market For 177 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1748

  • Year Built

    1957

  • $/SqFt

    $255

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 $1,695,000

Reduced By $255,000
View Details 41 Photos
On Market For 159 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3112

  • Year Built

    2005

  • $/SqFt

    $545

Center of Metro Orlando. NO OVERHEAD POWER LINES; UNDERGROUND! MLS#O6157218. COLONIALTOWN REALTY.

Home For Sale $485,500

Reduced By $84,250
View Details 31 Photos
On Market For 167 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1520

  • Year Built

    1955

  • $/SqFt

    $319

Very close proximity to Lake Berry & Lake Mizell, Windsong Cady Way Park, and Bike Paths. CALL, BUY, IMPROVE & CAPITALIZE NOW! MLS#S5094636. RE/MAX VANTAGE.

Home For Sale $1,695,000

Reduced By $200,000
View Details 31 Photos
On Market For 169 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 171 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 $4,995,000

Reduced By $500,000
View Details 41 Photos
On Market For 172 Days

  • Bedrooms

    5

  • Full Bath(s)

    7

  • Sq. Ft.

    5847

  • Year Built

    1957

  • $/SqFt

    $854

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

Home For Sale $1,975,000

Reduced By $20,000
View Details 51 Photos
On Market For 183 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3361

  • Year Built

    2023

  • $/SqFt

    $588

Don't miss this unique opportunity to experience the epitome of Island Transitional living in one of Winter Park's most desirable locations. MLS#O6150036. KELLER WILLIAMS WINTER PARK.

Pended $1,299,000

Reduced By $201,000
View Details 51 Photos
*POTENTIAL GREAT VALUE
On Market For 143 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    3353

  • Year Built

    2006

  • $/SqFt

    $387

Golfview - Don't miss out on the opportunity to make this remarkable Winter Park property your new home! MLS#O6145301. KELLER WILLIAMS WINTER PARK.

Home For Sale $494,500

Reduced By $15,500
View Details 16 Photos
*POTENTIAL GREAT VALUE
On Market For 186 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2096

  • Year Built

    1972

  • $/SqFt

    $236

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

Pended $498,000

Reduced By $71,000
View Details 8 Photos
On Market For 182 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2074

  • Year Built

    1964

  • $/SqFt

    $240

The benefits and features are too much to mention, including NO HOA. MLS#O6149004. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $459,999

Reduced By $20,000
View Details 48 Photos
On Market For 199 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1581

  • Year Built

    1970

  • $/SqFt

    $291

Winter Woods - We look forward to hearing from you. MLS#O6148504. ALIGN RIGHT REALTY SYNERGY.

Home For Sale $1,595,000

Reduced By $304,000
View Details 34 Photos
On Market For 196 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2829

  • Year Built

    2002

  • $/SqFt

    $564

Dixie Terrace - Plans also available for a pool - there is plenty of room for one to be added. MLS#O6147977. CORCORAN PREMIER REALTY.

Pended $3,350,000

View Details 30 Photos
On Market For 151 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4080

  • Year Built

    2022

  • $/SqFt

    $821

Tuscania - consider purchasing this house mostly furnished for a turn key experience. Car lift excluded MLS#O6146090. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $379,000

Reduced By $53,000
View Details 42 Photos
*POTENTIAL GREAT VALUE
On Market For 199 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1760

  • Year Built

    1954

  • $/SqFt

    $215

Temple Terrace - All of this and still within an hour drive to the fabulous Florida East Coast Beaches of Daytona Beach to Cocoa Beach. MLS#O6146989. COLDWELL BANKER REALTY.

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