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View 251 Winter Park Florida Homes for Sale

Home For Sale $799,500

Reduced By $25,500

View 2632 Mandan Trail Winter Park FL
View Details 31 Photos
View 2632 Mandan Trail Winter Park FL
View 2632 Mandan Trail Winter Park FL
View 2632 Mandan Trail Winter Park FL
On Market For 97 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2441

  • Year Built

    1967

  • $/SqFt

    $328

Don’t miss your chance to own this exceptional Winter Park Hills home where comfort, style and practicality come together in harmony. MLS#O6232937. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $625,000

Reduced By $24,900

View 1419 Miller Ave Winter Park FL
View Details 41 Photos
View 1419 Miller Ave Winter Park FL
View 1419 Miller Ave Winter Park FL
View 1419 Miller Ave Winter Park FL
On Market For 83 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1716

  • Year Built

    1932

  • $/SqFt

    $364

Lawndale - Don't miss your opportunity to own your piece of Winter Park. Schedule your private showing today. MLS#O6233039. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $354,900

Reduced By $10,100

View 2886 Roxbury Rd Winter Park FL
View Details 22 Photos
View 2886 Roxbury Rd Winter Park FL
View 2886 Roxbury Rd Winter Park FL
View 2886 Roxbury Rd Winter Park FL
On Market For 97 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1162

  • Year Built

    1954

  • $/SqFt

    $305

Fairbanks Shores - Seller will contribute $5000 toward buyer's closing costs and/or rate buydown. MLS#O6233435. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $850,000

Reduced By $100,000

View 731 Midget Dr Winter Park FL
View Details 19 Photos
View 731 Midget Dr Winter Park FL
View 731 Midget Dr Winter Park FL
View 731 Midget Dr Winter Park FL
On Market For 98 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    960

  • Year Built

    1941

  • $/SqFt

    $885

Don’t miss this diamond in the rough – call today for your showing!! ! MLS#O6232383. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $1,795,000

View Details 52 Photos
On Market For 98 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3472

  • Year Built

    1961

  • $/SqFt

    $517

Don’t miss this rare opportunity to own a slice of paradise in one of Winter Park’s most sought-after locations. MLS#O6230955. FANNIE HILLMAN & ASSOCIATES.

Pended $565,000

Reduced By $34,000
View Details 71 Photos
On Market For 81 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2278

  • Year Built

    1957

  • $/SqFt

    $248

Tanglewood - Don’t miss out on this incredible opportunity – schedule your private showing today, as this home won’t be on the market for long! MLS#O6231051. 1ST CLASS REAL ESTATE LEGACY GROUP.

Pended $735,000

Reduced By $64,000
View Details 23 Photos
On Market For 104 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2029

  • Year Built

    1969

  • $/SqFt

    $362

Don't miss this exceptional opportunity to own a beautifully updated home in Winter Park Hills! MLS#O6230771. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $439,000

View Details 16 Photos
On Market For 104 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1776

  • Year Built

    1968

  • $/SqFt

    $247

Winter Woods - Property is conveniently located to shopping and entertainment centers. MLS#T3546898. ALIGN RIGHT REALTY SRQ OPULENCE.

Home For Sale $429,000

View Details 39 Photos
On Market For 104 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1287

  • Year Built

    1975

  • $/SqFt

    $333

Painted inside and outside. NO HOA . MLS#S5109828. COLDWELL BANKER REALTY.

Pended $354,900

Reduced By $44,100
View Details 56 Photos
On Market For 75 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1092

  • Year Built

    1975

  • $/SqFt

    $325

Woodcrest - This home is a perfect blend of convenience and charm with room to expand into the home of your dreams. MLS#O6223454. PREMIUM PROPERTIES R.E SERVICE.

Home For Sale $297,000

Reduced By $18,000
View Details 18 Photos
On Market For 96 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1187

  • Year Built

    1994

  • $/SqFt

    $250

Winter Green - With these features, this property is more than just a house—it's a place you can truly home. MLS#O6230728. OPENDOOR BROKERAGE LLC.

Home For Sale $340,000

View Details 25 Photos
On Market For 44 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    904

  • Year Built

    1949

  • $/SqFt

    $376

This home has easy access to I4, shopping, dining, entertainment, and more! *Photos are from 8-5-2020. MLS#O6230165. INNOVATIVE REALTY, LLC.

Pended $429,900

View Details 38 Photos
On Market For 40 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1247

  • Year Built

    1981

  • $/SqFt

    $345

Wrenwood Heights - Don’t just take my word for it – come see how your life fits perfectly into this Winter Park wonder. MLS#O6229513. TBRO REALTY LLC.

Home For Sale $429,000

Reduced By $20,000
View Details 38 Photos
On Market For 110 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1836

  • Year Built

    1963

  • $/SqFt

    $234

Eastbrook - Don't miss the opportunity to make this impeccably remodeled home your own and enjoy the best of modern living in this vibrant community. MLS#S5108745. COMPASS FLORIDA, LLC.

Pended $540,000

View Details 30 Photos
On Market For 106 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2219

  • Year Built

    1972

  • $/SqFt

    $243

Arrowhead Cove - Don't miss this great opportunity to own a beautiful home. MLS#O6227932. OPENDOOR BROKERAGE LLC.

Home For Sale $370,000

View Details 22 Photos
On Market For 115 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1227

  • Year Built

    1961

  • $/SqFt

    $302

Shopping, entertainment, dining, and other amenities are also available just outside the Eastbrook. MLS#S5109126. PR REAL ESTATE SERVICES.

Home For Sale $1,199,900

View Details 34 Photos
On Market For 118 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2641

  • Year Built

    2024

  • $/SqFt

    $454

Karolina On Killarney - Plus this home's location provides easy access to I-4 and Orlando's world-famous theme parks, which are approximately 30 minutes away. MLS#O6226190. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $1,695,000

View Details 61 Photos
On Market For 119 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3777

  • Year Built

    1992

  • $/SqFt

    $449

Comstock Park - Located minutes from Park Avenue, Rollins College, Advent Health, and more this home is conveniently located and zoned for the A-rated Lakemont/Maitland Middle/WPHS school district. MLS#O6225250. KELLY PRICE & COMPANY LLC.

Home For Sale $559,900

Reduced By $25,000
View Details 41 Photos
On Market For 111 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2439

  • Year Built

    1997

  • $/SqFt

    $230

Do NOT miss out, call for a tour of this gorgeous home....!! ! MLS#NS1082187. THE HIGH TIDE GROUP.

Home For Sale $449,000

Reduced By $30,000
View Details 36 Photos
On Market For 118 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1560

  • Year Built

    1959

  • $/SqFt

    $288

Don’t miss out on this exceptional opportunity to own a piece of Winter Park living! MLS#O6224320. KELLER WILLIAMS WINTER PARK.

Pended $795,000

Reduced By $37,000
View Details 32 Photos
On Market For 124 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2461

  • Year Built

    2019

  • $/SqFt

    $323

Preserve At Hawks Crest - This Is A Must See Home! MLS#O6223854. BHHS FLORIDA REALTY.

Home For Sale $1,170,000

Reduced By $80,000
View Details 62 Photos
On Market For 127 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2871

  • Year Built

    1950

  • $/SqFt

    $408

Sylvan Park - Located just one and a half miles from the notable retail stores and restaurants of Park Avenue and within a well-graded public school zone, there is nothing you won’t love about this home or its location. MLS#O6223564. KELLY PRICE & COMPANY LLC.

Home For Sale $4,200,000

View Details 7 Photos
On Market For 128 Days

  • Bedrooms

    7

  • Full Bath(s)

    5

  • Sq. Ft.

    5500

  • Year Built

    1967

  • $/SqFt

    $764

From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity. MLS#O6220284. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,599,995

Reduced By $200,000
View Details 12 Photos
On Market For 128 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    2978

  • Year Built

    2024

  • $/SqFt

    $537

Northwood Terrace - Seller willing to buy 1 point down on buyers loan. MLS#O6223922. BALDWIN PARK REALTY LLC.

Pended $750,000

View Details 48 Photos
On Market For 57 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2589

  • Year Built

    2020

  • $/SqFt

    $290

Meadows At Hawks Crest - Don't miss the opportunity to make this exquisite home your own! MLS#O6221646. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $559,000

Reduced By $30,000
View Details 23 Photos
On Market For 131 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1740

  • Year Built

    1956

  • $/SqFt

    $321

Don't miss out on the chance to make this house your dream home in an unbeatable location! MLS#O6222187. WEICHERT REALTORS HALLMARK PROPERTIES.

Home For Sale $824,000

Reduced By $75,000
View Details 45 Photos
On Market For 109 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2584

  • Year Built

    1973

  • $/SqFt

    $319

Golfside - Don't miss out on the opportunity to make this remarkable property your new home. Schedule a showing today! MLS#O6219989. COMPASS FLORIDA LLC.

Pended $420,000

Reduced By $30,000
View Details 21 Photos
On Market For 137 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1525

  • Year Built

    1985

  • $/SqFt

    $275

Springview - The home is located on over a quarter acre with a fenced in yard. MLS#O6220867. YOUR HOME SOLD GUARANTEED REALTY.

Home For Sale $799,900

Reduced By $50,000
View Details 54 Photos
On Market For 141 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2503

  • Year Built

    1980

  • $/SqFt

    $320

Schedule your showing today and experience the tranquility and luxury of this unique home! MLS#O6220247. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $3,225,000

Reduced By $265,000
View Details 64 Photos
On Market For 141 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4807

  • Year Built

    2014

  • $/SqFt

    $671

Windsong Lakeside - One-owner custom home - Cahill Builders. Matterport link https://my.matterport.com/show/?m=xvJdom2Npmn MLS#O6220012. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $2,795,000

Reduced By $305,000
View Details 65 Photos
On Market For 129 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4487

  • Year Built

    2001

  • $/SqFt

    $623

Windsong Lakeside - Contact us today to schedule your private tour and experience luxury living at its finest. MLS#O6219532. KELLY PRICE & COMPANY LLC.

Home For Sale $2,200,000

View Details 69 Photos
On Market For 144 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3727

  • Year Built

    2014

  • $/SqFt

    $590

Don't miss the opportunity to own this exquisite property in Winter Park, where luxury and comfort come together seamlessly. Schedule your private showing today! MLS#O6219067. OLDE TOWN BROKERS INC.

Home For Sale $1,295,000

Reduced By $100,000
View Details 55 Photos
On Market For 124 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2432

  • Year Built

    1952

  • $/SqFt

    $532

Lake Knowles Terrace - A great investment opportunity to live among the finest homes in Winter Park and in well well-established neighborhood providing a lifestyle like no other. MLS#O6218751. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $950,000

Reduced By $250,000
View Details 29 Photos
On Market For 146 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2059

  • Year Built

    1953

  • $/SqFt

    $461

You will love the timeless design and relaxing comfort in this beautiful home! *NEW ROOF & AC - 2018* MLS#O6218556. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $499,999

Reduced By $65,001
View Details 31 Photos
On Market For 146 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1573

  • Year Built

    1958

  • $/SqFt

    $318

Sells Terrace - Hot Water Heater-2024, AC-2023, Mini Split-2023, Re-Landscape-2022, Irrigation Upgraded-2022, Spray Foam Insulation in Attic-2022, Gutters-2021, Replumbed-2020, Roof-2016 MLS#O6218549. THE WILKINS WAY LLC.

Pended $1,575,000

View Details 5 Photos
On Market For 147 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2858

  • Year Built

    2024

  • $/SqFt

    $551

Lake Killarney Shores - Make an appointment today before this amazing home is gone. MLS#O6218203. CLASSIC HOMES.

Home For Sale $946,500

Reduced By $18,500
View Details 34 Photos
On Market For 149 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2764

  • Year Built

    2010

  • $/SqFt

    $342

You must see it in person to truly appreciate all this home has to offer! MLS#O6217949. MAINFRAME REAL ESTATE.

Home For Sale $2,190,000

Reduced By $60,000
View Details 49 Photos
On Market For 152 Days

  • Bedrooms

    6

  • Full Bath(s)

    3

  • Sq. Ft.

    3554

  • Year Built

    1998

  • $/SqFt

    $616

Tuscany Terrace - This home is being sold with all the furniture but can be removed if Buyer does not want it. Some pictures are "Virtually Staged." MLS#O6217019. LOKATION.

Home For Sale $1,375,000

Reduced By $114,000
View Details 50 Photos
On Market For 143 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2838

  • Year Built

    2024

  • $/SqFt

    $484

Winter Park Village - Don't miss the chance to turn this dream home into your own reality —schedule a private tour today and step into the lifestyle you've been envisioning. Your ideal home awaits! MLS#O6216221. PREMIER SOTHEBYS INT'L REALTY.

Home For Sale $675,000

Reduced By $75,000
View Details 43 Photos
On Market For 153 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2309

  • Year Built

    1963

  • $/SqFt

    $292

Winter Park Pines - You want a place to play, you are minutes from the WP Pines golf course, Cady Way Bike trail, pool, pickleball/tennis courts, playground, and sports fields plus shopping and WP Hospital. MLS#O6216911. COLDWELL BANKER RESIDENTIAL RE.

Home For Sale $450,000

Reduced By $37,000
View Details 67 Photos
*POTENTIAL GREAT VALUE
On Market For 127 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3020

  • Year Built

    1959

  • $/SqFt

    $149

For piece of mind, seller will offer a HOME WARRANTY and $5,000 CREDIT towards flooring MLS#O6214075. REDFIN CORPORATION.

Home For Sale $900,000

Reduced By $300,000
View Details 89 Photos
*POTENTIAL GREAT VALUE
On Market For 154 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3834

  • Year Built

    1940

  • $/SqFt

    $235

Golfview - Schedule your private tour today and make this dream home yours! MLS#O6216744. KELLER WILLIAMS WINTER PARK.

Home For Sale $375,000

Reduced By $40,000
View Details 25 Photos
On Market For 135 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1318

  • Year Built

    1981

  • $/SqFt

    $285

Don't miss the chance to visit this delightful property before it's off the market! MLS#O6205879. COMPASS FLORIDA LLC.

Pended $545,000

Reduced By $80,000
View Details 60 Photos
On Market For 156 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1705

  • Year Built

    1926

  • $/SqFt

    $320

Lawndale - Easy access to I-4, 1792, Maitland, and downtown Orlando. Schedule your showing today! MLS#O6215384. KELLER WILLIAMS WINTER PARK.

Home For Sale $1,400,000

View Details 46 Photos
On Market For 159 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2334

  • Year Built

    2024

  • $/SqFt

    $600

Don't miss your chance to own this premier home in Winter Park! MLS#V4936864. SUMMER WIND REALTY CENTRAL FL.

Pended $398,900

Reduced By $36,100
View Details 34 Photos
On Market For 152 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1750

  • Year Built

    1967

  • $/SqFt

    $228

Eastbrook - With no HOA, this prime location home offers top-rated Seminole County schools nearby and is located near Downtown Orlando and Downtown Winter Park, as well as popular Central Florida theme parks, Winter Park hospital, public golf courses, and near Winter Park's Park Avenue boutique shopping, museums, Rollins College, Full Sail University, YMCA, and University of Central Florida, and so many other modern-day conveniences. Schedule your private showing today! MLS#O6213538. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $575,000

Reduced By $74,000
View Details 19 Photos
On Market For 157 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1144

  • Year Built

    1955

  • $/SqFt

    $503

Buyer will be responsible for confirming room measurements. MLS#O6214438. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $5,695,000

View Details 3 Photos
On Market For 163 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 $3,650,000

Reduced By $200,000
View Details 89 Photos
On Market For 146 Days

  • Bedrooms

    5

  • Full Bath(s)

    6

  • Sq. Ft.

    6223

  • Year Built

    2005

  • $/SqFt

    $587

Windsong Lakeside - Schedule your private tour today and discover the beauty and sophistication that awaits you in Windsong. MLS#O6212927. MAINFRAME REAL ESTATE.

Home For Sale $6,950,000

Reduced By $1,049,999
View Details 97 Photos
On Market For 167 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    7916

  • Year Built

    1996

  • $/SqFt

    $878

Kronenberger - This estate is a must see! MLS#O6212012. IRON VALLEY REAL ESTATE CENTRAL FLORIDA.

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