224 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $799,000

View 754 Gilbert Rd Winter Park FL
View Details 30 Photos
View 754 Gilbert Rd Winter Park FL
View 754 Gilbert Rd Winter Park FL
View 754 Gilbert Rd Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2289

  • Year Built

    1968

  • $/SqFt

    $349

Winter Park Pines - Don't miss your chance to make this stunning property your own – schedule a showing today and experience the epitome of modern living at 754 Gilbert Rd. MLS#O6202180. LEERDAM PROPERTIES INC..

Home For Sale $439,000

View 565 Heritage Blvd Winter Park FL
View Details 32 Photos
View 565 Heritage Blvd Winter Park FL
View 565 Heritage Blvd Winter Park FL
View 565 Heritage Blvd Winter Park FL
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1512

  • Year Built

    1967

  • $/SqFt

    $290

MLS#O6194293. BEAR TEAM REAL ESTATE.

Home For Sale $1,895,000

View 331 E Reading Way Winter Park FL
View Details 40 Photos
View 331 E Reading Way Winter Park FL
View 331 E Reading Way Winter Park FL
View 331 E Reading Way Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3361

  • Year Built

    2007

  • $/SqFt

    $564

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 $775,000

View 2835 Bear Island Pointe Winter Park FL
View Details 46 Photos
View 2835 Bear Island Pointe Winter Park FL
View 2835 Bear Island Pointe Winter Park FL
View 2835 Bear Island Pointe Winter Park FL
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2902

  • Year Built

    1997

  • $/SqFt

    $267

It is conveniently located to SR 417, lots of restaurants and shopping! Please schedule your appointment today! MLS#O6201350. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $650,000

View Details 35 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1668

  • Year Built

    1961

  • $/SqFt

    $390

This delightful property combines thoughtful updates with timeless charm, making it a must-see for those desiring a turn-key home in Winter Park. MLS#O6201320. LIGHTHOUSE PROPERTY GRP INC.

Home For Sale $649,500

View Details 46 Photos
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1726

  • Year Built

    2002

  • $/SqFt

    $376

Come and see this beautiful home before it's gone! MLS#O6200647. COLDWELL BANKER REALTY.

Home For Sale $425,000

View Details 48 Photos
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1362

  • Year Built

    1983

  • $/SqFt

    $312

Bel Aire Pines - Don't miss out on the opportunity to make this stunning pool home your own! MLS#O6201572. REDFIN CORPORATION.

Home For Sale $424,900

View Details 32 Photos
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1422

  • Year Built

    1980

  • $/SqFt

    $299

Wrenwood Heights - With its modern updates and attention to detail, this Winter Park home presents an exceptional opportunity for those seeking a high-quality and well-maintained living space in a desirable location. MLS#O6198477. THE REAL ESTATE COLLECTION LLC.

Home For Sale $420,000

View Details 21 Photos
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    987

  • Year Built

    1956

  • $/SqFt

    $426

Stansbury Estates - There were already offers on the home prior to it hitting the market! MLS#G5081725. REAL BROKER, LLC.

Home For Sale $365,000

View Details 33 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1350

  • Year Built

    1958

  • $/SqFt

    $270

Winter Park Estates - Whether you're enjoying a leisurely stroll through the neighborhood or unwinding in your own private backyard oasis, you'll love coming home to this peaceful paradise. MLS#O6202067. LPT REALTY.

Home For Sale $1,649,000

View Details 79 Photos
On Market For 3 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3028

  • Year Built

    2006

  • $/SqFt

    $545

Don't miss your chance to experience the epitome of gracious living in one of Florida's most coveted neighborhoods. MLS#O6200815. EXP REALTY LLC.

Home For Sale $1,489,000

View Details 36 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2812

  • Year Built

    2001

  • $/SqFt

    $530

Experience the epitome of lakeside living and make this dream home yours today. MLS#O6199613. SOTERA LIVING.

Home For Sale $799,000

View Details 36 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2822

  • Year Built

    2014

  • $/SqFt

    $283

Sanctuary At Aloma - Twenty-five minutes to Orlando and one hour to the beach! MLS#O6199197. COLDWELL BANKER REALTY.

Home For Sale $568,000

View Details 19 Photos
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1919

  • Year Built

    1970

  • $/SqFt

    $296

Woodcrest - Be A Happy Home Owner, Or Shrewd Investor! MLS#O6200506. COLDWELL BANKER REALTY.

Home For Sale $459,000

View Details 48 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1634

  • Year Built

    1993

  • $/SqFt

    $281

Don't miss the rare opportunity to call this community home! Schedule your private showing today! MLS#O6201373. COMPASS FLORIDA LLC.

Home For Sale $428,990

View Details 28 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1582

  • Year Built

    1956

  • $/SqFt

    $271

Tanglewood - Schedule your private tour today and discover the perfect blend of comfort, style, and convenience! MLS#O6200824. BHHS FLORIDA REALTY.

Home For Sale $1,650,000

View Details 61 Photos
On Market For 4 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3233

  • Year Built

    1953

  • $/SqFt

    $510

Maitland Shores - Experience the allure of Winter Park living at 940 Moss Lane, where each day unfolds with the promise of new adventures and endless possibilities. Schedule your private visit today. MLS#O6200641. MAINFRAME REAL ESTATE.

Pended $1,320,000

View Details 34 Photos
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3248

  • Year Built

    2015

  • $/SqFt

    $406

Conveniently located, this community offers easy access to SR 417, UCF, Rollins College, downtown Winter Park and Orlando. MLS#O6198447. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $774,900

View Details 86 Photos
*POTENTIAL GREAT VALUE
On Market For 4 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3496

  • Year Built

    2015

  • $/SqFt

    $222

Enclave At Aloma - MLS#O6201034. RE/MAX 200 REALTY.

Home For Sale $1,950,000

View Details 1 Photo
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2701

  • Year Built

    2024

  • $/SqFt

    $722

Sylvan Heights - Completing this house is the clean outdoor living space with a custom detailed ceiling and flooring creating a seamless transition from the living space to the pool entertainment space. MLS#O6199494. THE HOPE GROUP.

Home For Sale $519,900

View Details 34 Photos
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1575

  • Year Built

    1984

  • $/SqFt

    $330

Tamarak - This dream home has it all! Schedule your appointment today! MLS#O6199981. COLDWELL BANKER REALTY.

Home For Sale $11,795,000

View Details 48 Photos
*POTENTIAL GREAT VALUE
On Market For 9 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.

Home For Sale $4,150,000

View Details 59 Photos
*POTENTIAL GREAT VALUE
On Market For 9 Days

  • Bedrooms

    6

  • Full Bath(s)

    6

  • Sq. Ft.

    6939

  • Year Built

    1999

  • $/SqFt

    $598

Comstock Park - With its timeless elegance and modern amenities, this home offers a unique lifestyle of comfort and sophistication in the heart of Winter Park. MLS#O6199396. PALMANO GROUP RE BROKERAGE LLC.

Home For Sale $1,690,000

View Details 57 Photos
On Market For 9 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3518

  • Year Built

    1964

  • $/SqFt

    $480

Green Oaks - Schedule your private tour today and discover the luxury and sophistication of 1801 Legion Dr. MLS#O6199755. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $695,000

View Details 29 Photos
On Market For 10 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1275

  • Year Built

    1960

  • $/SqFt

    $545

Lake Knowles Terrace - Don't miss out on this fantastic opportunity to call this cozy bungalow home in one of Winter Park's most desirable neighborhoods! MLS#O6199975. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $449,000

View Details 37 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1584

  • Year Built

    1982

  • $/SqFt

    $283

Cedar Ridge - The only thing missing from this home is YOU. Schedule your private showing today! MLS#O6199274. CHARLES RUTENBERG REALTY ORLANDO.

Pended $445,000

View Details 35 Photos
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1846

  • Year Built

    1972

  • $/SqFt

    $241

Winter Woods has an optional HOA that covers things like community landscaping, and neighborhood events. MLS#O6197886. MILLER GRANT AND COMPANY.

Home For Sale $4,500,000

View Details 67 Photos
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    5320

  • Year Built

    2002

  • $/SqFt

    $846

Close to the charming boutiques and restaurants on Park Avenue. MLS#O6199601. FANNIE HILLMAN & ASSOCIATES.

Pended $2,100,000

View Details 82 Photos
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3300

  • Year Built

    1987

  • $/SqFt

    $636

Sylvan Lake Shores - Don't miss the opportunity to experience the captivating charm and natural beauty of this Winter Park gem.

MLS#O6199085. KELLY PRICE & COMPANY LLC.

Pended $644,900

View Details 41 Photos
On Market For 2 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2572

  • Year Built

    2015

  • $/SqFt

    $251

Be sure to schedule your private showing to tour this move-in ready home today! MLS#O6197471. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $469,900

View Details 41 Photos
On Market For 11 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1434

  • Year Built

    1973

  • $/SqFt

    $328

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 $2,790,000

View Details 40 Photos
On Market For 12 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4905

  • Year Built

    1986

  • $/SqFt

    $569

Virginia Heights - *Walk-through video filmed before kitchen, bathrooms, and whole house repainted in 2022. MLS#U8240071. WWW.HOMEZU.COM.

Home For Sale $2,495,000

View Details 48 Photos
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3154

  • Year Built

    1951

  • $/SqFt

    $791

Schedule you're showing today and experience the epitome of luxury living at 1161 Lincoln Circle." MLS#O6198338. FANNIE HILLMAN & ASSOCIATES.

Pended $1,775,000

View Details 54 Photos
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    3159

  • Year Built

    2000

  • $/SqFt

    $562

Temple Heights - This ideal location is just a few blocks from the WP YMCA, grocery stores, restaurants and shopping off Aloma, and a mile or so from Park Ave! MLS#O6194759. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $775,000

View Details 51 Photos
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2137

  • Year Built

    2021

  • $/SqFt

    $363

Hawks Crest - Schedule your showing today and prepare to be captivated by the allure of Hawk's Crest living. Measurements are approximately. MLS#T3520666. FLORIDA LUXURY REALTY INC.

Home For Sale $4,250,000

View Details 19 Photos
On Market For 16 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.

Pended $1,895,000

View Details 52 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3504

  • Year Built

    1999

  • $/SqFt

    $541

Osceola Shores - 160 Trismen Terrace is truly a home for those who appreciate entertaining. MLS#O6197555. OLDE TOWN BROKERS INC.

Pended $1,800,000

View Details 55 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3404

  • Year Built

    1990

  • $/SqFt

    $529

Lugano Terrace - Bedroom Closet Type: Walk-in Closet (Primary Bedroom). MLS#O6197726. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $3,095,000

View Details 61 Photos
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4216

  • Year Built

    2020

  • $/SqFt

    $734

Comstock Park - Don't miss your opportunity to own a piece of Winter Park's finest. Schedule your private showing today! MLS#O6196961. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $749,900

View Details 48 Photos
On Market For 39 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1370

  • Year Built

    1952

  • $/SqFt

    $547

MLS#O6196093. RE/MAX 200 REALTY.

Home For Sale $635,000

View Details 18 Photos
On Market For 20 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1376

  • Year Built

    1954

  • $/SqFt

    $461

Orangewood Park - Extra features and updates include: new HVAC 2018, re-piped interior, no cast iron (rare), Roof 2017, replaced well pump for irrigation (low waste water and sewer bills), renovated patio, updated landscape, and renovated guest bathroom. MLS#O6196291. THE KEY REALTY GROUP.

Home For Sale $625,000

View Details 29 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1946

  • Year Built

    1950

  • $/SqFt

    $321

MLS#S5103315. EXP REALTY LLC.

Pended $550,000

View Details 35 Photos
On Market For 5 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1974

  • Year Built

    1967

  • $/SqFt

    $279

The location of this home is incredibly convenient, with easy access to Park Ave., Winter Park Pines Golf Club, Cady Way Pool & Park, Cady Way Bike Trail, the Center for Health and Wellbeing, Rollins College, Full Sail, Orlando International Airport, and the renowned Advent Health Hospital - all in one convenient location! MLS#O6196142. EXP REALTY LLC.

Home For Sale $397,000

View Details 29 Photos
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1310

  • Year Built

    1964

  • $/SqFt

    $303

Eastbrook - Come see this home today and make it yours! MLS#O6196882. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $385,000

View Details 33 Photos
On Market For 19 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1393

  • Year Built

    1958

  • $/SqFt

    $276

Conveniently located in Winter Park with easy access to shopping, dining, parks, and top-rated schools, you don't want to miss this opportunity! MLS#O6195536. COLDWELL BANKER REALTY.

Pended $775,000

View Details 38 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2241

  • Year Built

    1962

  • $/SqFt

    $346

Welcome home, call to schedule your private showing today!! ! MLS#O6196765. FANNIE HILLMAN & ASSOCIATES.

Pended $375,000

View Details 36 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1800

  • Year Built

    1988

  • $/SqFt

    $208

Other highlights include a well system equipped with an iron filter and chlorinator, a durable hardy board exterior, as well as a convenient carport and shed. MLS#C7491066. EXP REALTY LLC.

Home For Sale $1,792,000

View Details 59 Photos
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    3330

  • Year Built

    2017

  • $/SqFt

    $538

Golf and tennis neighborhood Racquet Club, Interlachen Country Club, and Winter Park 9 Golf Course.

MLS#O6194670. KELLY PRICE & COMPANY LLC.

Home For Sale $1,117,500

Reduced By $57,500
View Details 25 Photos
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2797

  • Year Built

    1980

  • $/SqFt

    $400

Plus, with sought-after Winter Park schools just a stone's throw away, you'll enjoy peace of mind knowing your family is in a top-notch educational environment. MLS#O6195768. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $999,900

View Details 9 Photos
On Market For 25 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    962

  • Year Built

    1952

  • $/SqFt

    $1,039

Parklando - This home is near Lake Sue, Leu Gardens, Mead Botanical Gardens and many more gems of Winter Park. MLS#V4935714. GREENE REALTY OF FLORIDA LLC.

Viewing HOMES 1 to 50 of 224

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-278-2057 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$580,062
$439,900
97
2.1%
38.1%
79

Apopka
$509,826
$465,000
473
1.3%
42.7%
78

Belle Isle
$927,429
$766,950
24
4.2%
62.5%
67

Casselberry
$440,861
$425,000
76
3.9%
40.8%
68

Celebration
$1,376,290
$1,169,000
53
0.0%
52.8%
104

Champions Gate
$666,919
$692,500
26
0.0%
42.3%
177

Chuluota
$1,309,175
$573,750
20
0.0%
50.0%
62

Clermont
$582,550
$499,850
570
0.7%
42.6%
89

Gotha
$1,001,544
$582,450
16
0.0%
56.2%
53

Groveland
$461,139
$417,000
198
1.5%
43.4%
72

Harmony
$448,497
$430,900
53
0.0%
50.9%
89

Kissimmee
$535,586
$460,000
1849
0.7%
44.4%
99

Longwood
$792,149
$607,450
176
1.1%
40.9%
62

Maitland
$1,156,894
$640,000
67
0.0%
44.8%
87

Minneola
$543,052
$522,495
112
0.0%
24.1%
79

Montverde
$1,587,158
$1,190,999
59
0.0%
33.9%
131

Ocoee
$556,916
$499,000
118
1.7%
43.2%
70

Orlando
$683,463
$495,000
2285
1.6%
40.6%
87

Oviedo
$697,520
$609,000
161
0.0%
32.9%
52

Poinciana
$333,306
$319,945
454
0.7%
52.4%
120

Reunion
$1,667,642
$1,224,500
88
0.0%
58.0%
165

Saint Cloud
$528,169
$459,900
819
0.2%
43.3%
96

Sanford
$509,065
$425,000
367
0.8%
53.1%
90

Sorrento
$660,346
$510,990
87
0.0%
50.6%
77

Windermere
$2,358,223
$1,475,000
225
0.9%
46.2%
97

Winter Garden
$843,287
$699,000
539
0.0%
37.7%
78

Winter Springs
$547,367
$499,900
115
0.9%
47.0%
61

EasyStreet

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