216 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $799,000

View 5263 Pine Lily Cir Winter Park FL
View Details 36 Photos
View 5263 Pine Lily Cir Winter Park FL
View 5263 Pine Lily Cir Winter Park FL
View 5263 Pine Lily Cir Winter Park FL
On Market Today

  • 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 $1,650,000

View 940 Moss Ln Winter Park FL
View Details 61 Photos
View 940 Moss Ln Winter Park FL
View 940 Moss Ln Winter Park FL
View 940 Moss Ln Winter Park FL
On Market For 2 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.

Home For Sale $1,320,000

View 1340 Heavenly Cove Winter Park FL
View Details 34 Photos
View 1340 Heavenly Cove Winter Park FL
View 1340 Heavenly Cove Winter Park FL
View 1340 Heavenly Cove Winter Park FL
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 7945 Pleasant Pine Cir Winter Park FL
View Details 86 Photos
View 7945 Pleasant Pine Cir Winter Park FL
View 7945 Pleasant Pine Cir Winter Park FL
View 7945 Pleasant Pine Cir Winter Park FL
*POTENTIAL GREAT VALUE
On Market For 2 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 4 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 6 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 7 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 7 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 7 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 8 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 7 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 10 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 9 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 10 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 11 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.

Home For Sale $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 13 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 appoximately. MLS#T3520666. FLORIDA LUXURY REALTY INC.

Home For Sale $4,250,000

View Details 19 Photos
On Market For 14 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 15 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 37 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 18 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 15 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 16 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 17 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 18 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 21 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 23 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.

Pended $650,000

View Details 44 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2407

  • Year Built

    1967

  • $/SqFt

    $270

Brookshire Heights - ROOF 2013 HAVC 2018 HOT WATER HEATER 2020, NEW ELECTRIC 2017, EXTERIOR PAINT 2018 The property has been PRE-INSPECTED for your buying confidence. MLS#O6196213. TTT REALTY LLC.

Pended $469,900

View Details 31 Photos
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1630

  • Year Built

    1969

  • $/SqFt

    $288

Eastbrook - Lot Size is 75' X 110'. MLS#O6195238. ANNE ROGERS REALTY GROUP INC.

Home For Sale $368,500

View Details 3 Photos
On Market For 18 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1524

  • Year Built

    1983

  • $/SqFt

    $242

Close to shopping and transportation, Zoned for Eastbrook Elementary, Tuskawilla Middle and Lake Howell High School. MLS#O6192105. MAGNOLIA PROPERTY SALES.

Home For Sale $1,400,000

View Details 11 Photos
On Market For 23 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1440

  • Year Built

    1947

  • $/SqFt

    $972

Charmont - The last time a house sold on this street was four years ago. MLS#V4935671. GREENE REALTY OF FLORIDA LLC.

Home For Sale $6,995,000

View Details 52 Photos
On Market For 27 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4792

  • Year Built

    1998

  • $/SqFt

    $1,460

Sicilian Shores - Roof and boathouse roof updated 2022. MLS#O6195529. CHARLES RUTENBERG REALTY ORLANDO.

Home For Sale $750,000

View Details 36 Photos
On Market For 27 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1669

  • Year Built

    1927

  • $/SqFt

    $449

Lawndale - Welcome to your dream home, where history and modernity live in perfect harmony. MLS#O6195037. BISON REALTY.

Pended $535,000

View Details 84 Photos
On Market For 4 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1983

  • Year Built

    1987

  • $/SqFt

    $270

Don't miss your chance to make this Winter Park oasis your own – schedule a showing today! MLS#O6195782. CALL IT CLOSED INTL REALTY.

Pended $530,000

Reduced By $20,000
View Details 34 Photos
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2201

  • Year Built

    1969

  • $/SqFt

    $241

Experience the perfect blend of elegance, functionality, and relaxation in this exceptional home. Schedule your showing today. MLS#O6194827. KELLER WILLIAMS ADVANTAGE III REALTY.

Pended $995,000

View Details 100 Photos
*POTENTIAL GREAT VALUE
On Market For 10 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    4295

  • Year Built

    2019

  • $/SqFt

    $232

Waters Edge At Hawks Crest - This home is also located just a short drive from Downtown Orlando, UCF, and major highways I-4 and SR-436, making traveling Central Florida a breeze! Schedule your private tour today. MLS#O6194932. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $750,000

View Details 47 Photos
*POTENTIAL GREAT VALUE
On Market For 22 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3394

  • Year Built

    1974

  • $/SqFt

    $221

Lake Waunatta Woods - (Foyer, Dining Room and Great Room Chandeliers along with Washer and Dryer do not convey.) MLS#O6195581. PARKSIDE PROPERTIES, LLC.

Home For Sale $719,000

Reduced By $20,000
View Details 27 Photos
On Market For 22 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2153

  • Year Built

    1977

  • $/SqFt

    $334

This incredible home also boasts an ideal location and with top-rated schools: Lakemont Elementary, Maitland Middle and Winter Park High. MLS#O6194323. COLDWELL BANKER REALTY.

Pended $299,000

View Details 18 Photos
On Market For 12 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1156

  • Year Built

    1995

  • $/SqFt

    $259

Winter Park Oaks - Schedule a viewing today and start envisioning your dream lifestyle. MLS#O6195212. LA ROSA REALTY CENTRAL FLORIDA.

Home For Sale $345,000

Reduced By $10,000
View Details 28 Photos
On Market For 29 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1056

  • Year Built

    1957

  • $/SqFt

    $327

Conveniently located minutes to UCF, Full Sail, Barry University, Valencia, multiple grocery stores and pharmacies, Winter Park’s scenic Park Avenue, Downtown Orlando, and Orlando International Airport. MLS#O6194782. LIV AT NONA.

Home For Sale $1,899,700

Reduced By $89,000
View Details 26 Photos
On Market For 27 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2859

  • Year Built

    1948

  • $/SqFt

    $664

Kronenberger - Bedroom Closet Type: Walk-in Closet (Primary Bedroom). MLS#O6193303. FLORIDA PROPERTY LLC.

Home For Sale $1,399,999

Reduced By $95,001
View Details 56 Photos
On Market For 25 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3074

  • Year Built

    2017

  • $/SqFt

    $455

Ideally situated near Lakemont Elementary, Publix, Advent Health, and mere minutes from Park Avenue. MLS#O6194226. THE HOPE GROUP.

Viewing HOMES 1 to 50 of 216

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
$574,978
$439,900
99
1.0%
37.4%
79

Apopka
$508,734
$464,950
470
1.3%
42.3%
79

Belle Isle
$894,012
$725,000
25
4.0%
64.0%
68

Casselberry
$440,313
$419,900
75
4.0%
40.0%
67

Celebration
$1,385,971
$1,195,000
55
0.0%
50.9%
107

Champions Gate
$659,811
$690,000
27
0.0%
40.7%
170

Chuluota
$1,309,175
$573,750
20
0.0%
50.0%
60

Clermont
$577,270
$499,000
569
0.7%
42.7%
90

Gotha
$1,030,647
$599,900
15
0.0%
60.0%
54

Groveland
$462,737
$415,000
191
1.6%
44.0%
74

Harmony
$444,628
$425,000
55
0.0%
47.3%
89

Kissimmee
$535,891
$460,000
1843
0.8%
44.0%
101

Longwood
$778,444
$597,000
176
1.1%
40.3%
62

Maitland
$1,167,286
$636,475
66
0.0%
45.5%
87

Minneola
$545,735
$531,990
113
0.0%
24.8%
80

Montverde
$1,606,609
$1,230,000
58
0.0%
34.5%
131

Ocoee
$529,344
$500,000
119
1.7%
42.0%
69

Orlando
$686,815
$495,000
2246
1.6%
41.2%
89

Oviedo
$692,609
$609,000
151
0.0%
33.8%
53

Poinciana
$332,159
$319,900
461
0.7%
52.3%
119

Reunion
$1,678,801
$1,249,000
88
0.0%
56.8%
168

Saint Cloud
$523,998
$458,400
817
0.2%
42.6%
97

Sanford
$508,433
$424,870
369
0.8%
52.3%
90

Sorrento
$649,899
$509,900
85
0.0%
51.8%
83

Windermere
$2,389,364
$1,499,000
219
0.9%
47.0%
101

Winter Garden
$844,411
$701,900
519
0.2%
37.4%
78

Winter Springs
$549,963
$499,450
114
0.9%
43.9%
61

EasyStreet

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