96 Results

View 96 Winter Park Florida Homes for Sale

Home For Sale $1,980,000

View 501 Country Club Dr Winter Park FL
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View 501 Country Club Dr Winter Park FL
View 501 Country Club Dr Winter Park FL
View 501 Country Club Dr Winter Park FL
On Market For 73 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 $1,699,900

Reduced By $50,100

View 2914 Reef Knot Pl Winter Park FL
View Details 53 Photos
View 2914 Reef Knot Pl Winter Park FL
View 2914 Reef Knot Pl Winter Park FL
View 2914 Reef Knot Pl Winter Park FL
On Market For 73 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4173

  • Year Built

    2019

  • $/SqFt

    $407

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

Pended $1,595,000

Reduced By $135,000

View 1016 Tuscany Pl Winter Park FL
View Details 91 Photos
View 1016 Tuscany Pl Winter Park FL
View 1016 Tuscany Pl Winter Park FL
View 1016 Tuscany Pl Winter Park FL
On Market For 44 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3151

  • Year Built

    1978

  • $/SqFt

    $506

Recognized design firm PHIL KEAN has produce an Architectural design for this property that would increase the value of the property, current owner are including the drawings as part of the package. SEE RENDERINGS ATTACHED. MLS#O6178427. FORTUNE INTERNATIONAL REALTY.

Home For Sale $1,500,000

Reduced By $99,000

View 4091 Scarlet Iris Pl Winter Park FL
View Details 73 Photos
View 4091 Scarlet Iris Pl Winter Park FL
View 4091 Scarlet Iris Pl Winter Park FL
View 4091 Scarlet Iris Pl Winter Park FL
*POTENTIAL GREAT VALUE
On Market For 74 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 $2,250,000

Reduced By $50,000
View Details 58 Photos
On Market For 79 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4312

  • Year Built

    2004

  • $/SqFt

    $522

Sylvan Park - Ideal for family living, walkability and entertaining. MLS#O6179257. PREMIER SOTHEBY'S INTL. REALTY.

Pended $1,349,000

Reduced By $51,000
View Details 35 Photos
On Market For 50 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2894

  • Year Built

    1998

  • $/SqFt

    $466

Enjoy peace, serenity, and the ultimate feeling of old Winter Park in this stately home, located in the Audubon K-8 school district and minutes away from the best Orlando has to offer. MLS#O6179374. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,950,000

Reduced By $200,000
View Details 41 Photos
On Market For 80 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.

Pended $1,299,990

Reduced By $100,000
View Details 93 Photos
On Market For 43 Days

  • Bedrooms

    6

  • Full Bath(s)

    4

  • Sq. Ft.

    4309

  • Year Built

    2020

  • $/SqFt

    $302

Waters Edge At Hawks Crest - Schedule your private tour today and elevate your lifestyle with this extraordinary home. MLS#O6177814. MVP REALTY ASSOCIATES LLC.

Home For Sale $2,450,000

View Details 68 Photos
On Market For 88 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3989

  • Year Built

    2012

  • $/SqFt

    $614

Windsong Elizabeths Walk -

MLS#O6177110. THE SIMON SIMAAN GROUP.

Home For Sale $1,650,000

Reduced By $350,000
View Details 36 Photos
On Market For 91 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3400

  • Year Built

    1992

  • $/SqFt

    $485

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

Home For Sale $2,525,000

Reduced By $175,000
View Details 59 Photos
On Market For 90 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4638

  • Year Built

    2019

  • $/SqFt

    $544

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 92 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.

Pended $2,495,000

View Details 91 Photos
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    5

  • Sq. Ft.

    4240

  • Year Built

    2008

  • $/SqFt

    $588

Bedroom Closet Type: Walk-in Closet (Primary Bedroom). MLS#O6174225. OLDE TOWN BROKERS INC.

Pended $1,494,900

Reduced By $154,100
View Details 50 Photos
On Market For 67 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2901

  • Year Built

    1958

  • $/SqFt

    $515

Green Terrace - *In attachments are pool renderings upon request as well as a full feature sheet. MLS#O6166451. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,385,000

Reduced By $165,000
View Details 37 Photos
*POTENTIAL GREAT VALUE
On Market For 97 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3578

  • Year Built

    1975

  • $/SqFt

    $387

Fontainebleau - Welcome to an oasis where comfort and style blend seamlessly Welcome HOME! MLS#O6174319. KELLER WILLIAMS ADVANTAGE 2 REALTY.

Home For Sale $2,200,000

Reduced By $200,000
View Details 53 Photos
On Market For 165 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 Details 24 Photos
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 Details 12 Photos
On Market For 103 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 $5,566,500

View Details 90 Photos
On Market For 102 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 $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.

Pended $2,295,000

Reduced By $100,000
View Details 33 Photos
On Market For 110 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.

Home For Sale $3,199,000

Reduced By $300,000
View Details 55 Photos
On Market For 121 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 121 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.

Home For Sale $1,575,000

Reduced By $150,000
View Details 26 Photos
*POTENTIAL GREAT VALUE
On Market For 123 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.

Pended $1,290,000

Reduced By $160,000
View Details 24 Photos
On Market For 125 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.

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 144 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 $1,999,000

Reduced By $501,000
View Details 68 Photos
*POTENTIAL GREAT VALUE
On Market For 137 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 $1,650,000

Reduced By $20,350,000
View Details 50 Photos
On Market For 154 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3448

  • Year Built

    2020

  • $/SqFt

    $479

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 $3,500,000

View Details 59 Photos
On Market For 173 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 172 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 $1,695,000

Reduced By $255,000
View Details 41 Photos
On Market For 174 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 $4,130,000

Reduced By $270,000
View Details 65 Photos
On Market For 179 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 184 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 186 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 187 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.

Pended $1,975,000

Reduced By $20,000
View Details 51 Photos
On Market For 181 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.

Home For Sale $1,595,000

Reduced By $304,000
View Details 34 Photos
On Market For 211 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.

Home For Sale $1,799,000

Reduced By $196,000
View Details 52 Photos
On Market For 242 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3669

  • Year Built

    2007

  • $/SqFt

    $490

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 $1,550,000

Reduced By $375,000
View Details 41 Photos
On Market For 158 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.

Pended $1,150,000

Reduced By $100,000
View Details 51 Photos
On Market For 255 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1368

  • Year Built

    1953

  • $/SqFt

    $841

Maitland Shores - New ROOF, NEW TRANE A/C, ALL NEW PELLA WINDOWS THROUGHOUT INCLUDING GARAGE AND MUCH MORE...The tranquil backyard with a water view is great for BBQ's and enjoying family and guests. MLS#O6131531. BHHS RESULTS REALTY.

Home For Sale $5,400,000

View Details 34 Photos
On Market For 285 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 $1,600,000

Reduced By $300,000
View Details 60 Photos
*POTENTIAL GREAT VALUE
On Market For 312 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4029

  • Year Built

    2022

  • $/SqFt

    $397

Home comes with a ONE-YEAR BUILDERS WARRANTY! Schedule a private tour today! MLS#O6087208. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $1,399,000

View Details 8 Photos
On Market For 218 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2460

  • Year Built

    2023

  • $/SqFt

    $569

Lake Knowles Terrace - Please reach out today for more detailed information! MLS#O6046368. COLDWELL BANKER REALTY.

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