217 Results

Winter Park Homes For Sale & Winter Park FL Real Estate

Home For Sale $550,000

View 2821 Little John Rd Winter Park FL
View Details 35 Photos
View 2821 Little John Rd Winter Park FL
View 2821 Little John Rd Winter Park FL
View 2821 Little John Rd Winter Park FL
On Market Today

  • 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 $385,000

View 3526 Arbutus Ln Winter Park FL
View Details 33 Photos
View 3526 Arbutus Ln Winter Park FL
View 3526 Arbutus Ln Winter Park FL
View 3526 Arbutus Ln Winter Park FL
On Market For 3 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.

Home For Sale $775,000

View 2498 Whitehall Cir Winter Park FL
View Details 38 Photos
View 2498 Whitehall Cir Winter Park FL
View 2498 Whitehall Cir Winter Park FL
View 2498 Whitehall Cir Winter Park FL
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.

Home For Sale $375,000

View 7915 Bates Rd Winter Park FL
View Details 36 Photos
View 7915 Bates Rd Winter Park FL
View 7915 Bates Rd Winter Park FL
View 7915 Bates Rd Winter Park FL
On Market For 3 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 4 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 $1,175,000

View Details 25 Photos
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2797

  • Year Built

    1980

  • $/SqFt

    $420

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 9 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.

Home For Sale $469,900

View Details 31 Photos
On Market For 5 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 $1,400,000

View Details 11 Photos
On Market For 9 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 13 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 13 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.

Home For Sale $550,000

View Details 34 Photos
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2201

  • Year Built

    1969

  • $/SqFt

    $250

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 $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.

Home For Sale $995,000

View Details 100 Photos
*POTENTIAL GREAT VALUE
On Market For 8 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 8 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 $739,000

View Details 27 Photos
On Market For 8 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2153

  • Year Built

    1977

  • $/SqFt

    $343

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.

Home For Sale $299,000

View Details 18 Photos
On Market For 9 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 $355,000

View Details 28 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1056

  • Year Built

    1957

  • $/SqFt

    $336

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 $1,988,700

View Details 26 Photos
On Market For 13 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2859

  • Year Built

    1948

  • $/SqFt

    $696

Kronenberger - Experience the best of Winter Park living with this exceptional property. MLS#O6193303. FLORIDA PROPERTY LLC.

Home For Sale $1,445,000

Reduced By $50,000
View Details 56 Photos
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3074

  • Year Built

    2017

  • $/SqFt

    $470

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

Pended $548,997

View Details 34 Photos
On Market For 2 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1746

  • Year Built

    1967

  • $/SqFt

    $314

Golfside - CONTACT ME for a PRIVATE SHOWING MLS#O6188993. UNITED REAL ESTATE PREFERRED.

Pended $350,000

View Details 27 Photos
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    1152

  • Year Built

    1959

  • $/SqFt

    $304

Call today to schedule your private showing. MLS#O6192913. COLDWELL BANKER REALTY.

Home For Sale $1,995,000

View Details 22 Photos
On Market For 15 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4738

  • Year Built

    1948

  • $/SqFt

    $421

Woodmere Terrace - Experience the essence of timeless elegance and modern comfort at this remarkable address. MLS#O6193348. PREMIER SOTHEBY'S INTL. REALTY.

Home For Sale $1,695,000

View Details 71 Photos
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3150

  • Year Built

    2006

  • $/SqFt

    $538

Charmont - Schedule your private showing today before it's SOLD! MLS#O6193582. VOSS REALTY INC.

Pended $1,325,000

View Details 66 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2942

  • Year Built

    2006

  • $/SqFt

    $450

Windsong Elizabeths Walk - Central Florida living at its best in one of Winter Park's most sought-after communities. MLS#O6192936. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $1,070,000

View Details 52 Photos
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3057

  • Year Built

    2015

  • $/SqFt

    $350

Schedule a showing today and experience the beauty of this remarkable home! MLS#O6193168. VR HOMES LLC.

Home For Sale $499,500

View Details 45 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1522

  • Year Built

    1964

  • $/SqFt

    $328

What are you waiting for, come check out this home today! MLS#O6190494. KELLER WILLIAMS ADVANTAGE REALTY.

Home For Sale $459,000

View Details 33 Photos
On Market For 14 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1671

  • Year Built

    1981

  • $/SqFt

    $275

Cedar Ridge - And if that's not enough...let's not forget this amazing location in Winter Park - easy access to the 417 and 436, close to Trinity Prep and Park Maitland Preschool, and Foxtail Coffee, Kelly's Ice Cream & Donut King right down the street! MLS#O6193153. MEGAN DOWDY REALTY, LLC.

Home For Sale $459,000

View Details 43 Photos
On Market For 15 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1793

  • Year Built

    1976

  • $/SqFt

    $256

Situated close to shopping, schools, and major roads, you'll enjoy easy access to all the amenities and attractions Central Florida has to offer. MLS#O6191464. WATSON REALTY CORP.

Home For Sale $2,199,999

View Details 67 Photos
On Market For 17 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3971

  • Year Built

    1990

  • $/SqFt

    $554

College Place - With its architectural integrity, handcrafted details, central location, enchanting central skylight, and minutes’ walk to Lake Virginia and Park Avenue, it is a rare find that epitomizes the art of living in sunny Florida. MLS#O6190102. NEXTHOME MY WAY.

Home For Sale $1,374,900

View Details 89 Photos
On Market For 15 Days

  • Bedrooms

    5

  • Full Bath(s)

    4

  • Sq. Ft.

    3252

  • Year Built

    2024

  • $/SqFt

    $423

Golfview - Make an appointment to see this beautiful home today. MLS#O6193452. RE/MAX EXCLUSIVE COLLECTION.

Home For Sale $635,000

View Details 64 Photos
On Market For 17 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2481

  • Year Built

    1999

  • $/SqFt

    $256

CALL TODAY to schedule your private showing! MLS#O6191927. KELLER WILLIAMS REALTY AT THE PARKS.

Pended $549,900

View Details 36 Photos
*POTENTIAL GREAT VALUE
On Market For 6 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2391

  • Year Built

    1984

  • $/SqFt

    $230

Tamarak - Don't miss your opportunity to experience the best of Florida living in this exceptional property. Schedule your showing today! MLS#O6193281. CREEGAN GROUP.

Pended $425,000

View Details 31 Photos
On Market For 10 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1535

  • Year Built

    1982

  • $/SqFt

    $277

Bel Aire Pines - Make an appointment to see this home today! MLS#O6192780. THE WILKINS WAY LLC.

Pended $419,000

Reduced By $10,000
View Details 35 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1542

  • Year Built

    1973

  • $/SqFt

    $272

Woodcrest - Driveway pavers extended to the end of the house for optimal parking. MLS#O6193481. ROBERT SLACK LLC.

Home For Sale $3,890,000

View Details 3 Photos
On Market For 16 Days

  • Bedrooms

    5

  • Full Bath(s)

    5

  • Sq. Ft.

    4055

  • Year Built

    2025

  • $/SqFt

    $959

Price is subject to change through construction. MLS#O6191966. CORCORAN PREMIER REALTY.

Pended $2,200,000

View Details 54 Photos
On Market For 3 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3276

  • Year Built

    1995

  • $/SqFt

    $672

Don't miss your chance to make this exquisite property your own and enjoy the epitome of Florida luxury living. MLS#O6192372. KELLER WILLIAMS WINTER PARK.

Pended $775,000

View Details 40 Photos
On Market For 7 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2406

  • Year Built

    1980

  • $/SqFt

    $322

Enjoy beautiful walks through the neighborhood and 2 private tennis courts which are owned by the association. Great Winter Park Schools! -- MLS#O6192070. FANNIE HILLMAN & ASSOCIATES.

Pended $355,000

View Details 1 Photo
*POTENTIAL GREAT VALUE
On Market For 1 Day

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1615

  • Year Built

    1983

  • $/SqFt

    $220

Schedule your showing today and make this exceptional home yours! MLS#O6191820. KEYSEEKERS REAL ESTATE.

Pended $2,200,000

View Details 100 Photos
On Market For 19 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4176

  • Year Built

    2004

  • $/SqFt

    $527

Windsong Lookout Landing - Schedule your showing today and envision your lifestyle in this remarkable sanctuary.

MLS#O6181952. KELLY PRICE & COMPANY LLC.

Home For Sale $525,000

View Details 39 Photos
On Market For 20 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1996

  • Year Built

    1966

  • $/SqFt

    $263

Winter Park Estates - Don't miss out on the chance to make it yours! MLS#O6191733. REALTY HUB.

Home For Sale $749,999

Reduced By $49,991
View Details 34 Photos
On Market For 21 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2894

  • Year Built

    2021

  • $/SqFt

    $259

Hawks Crest - Don't miss your chance to experience the epitome of luxury living in Winter Park's finest community. Schedule your private showing today! ! MLS#O6191658. MVP REALTY ASSOCIATES LLC.

Pended $725,000

View Details 38 Photos
On Market For 6 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1817

  • Year Built

    1926

  • $/SqFt

    $399

Orwin Manor - New window treatments in 2021, HW 2021, Roof 2018, HVAC 2017 Furniture is available for purchase MLS#O6191051. ACME REAL ESTATE FLORIDA LLC.

Pended $464,900

View Details 45 Photos
On Market For 5 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1223

  • Year Built

    1947

  • $/SqFt

    $380

Minutes from Winter Park’s historic Park Avenue with Shopping and Restaurants galore, Orlando Museum of Art, The Orlando Science Center, Mead Gardens, AdventHealth Orlando Hospital, Downtown and the Sun Rail Station as well as easy access to the Interstate. MLS#T3513193. ARRICO REALTY & PROPERTY MGMT..

Pended $399,500

View Details 31 Photos
On Market For 26 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1477

  • Year Built

    1955

  • $/SqFt

    $270

Fairbanks Shores - Don't miss this unparalleled opportunity to own a piece of Winter Park, where such remarkable offerings are a rare find. MLS#O6191192. COMPASS FLORIDA LLC.

Home For Sale $2,749,000

View Details 61 Photos
On Market For 23 Days

  • Bedrooms

    4

  • Full Bath(s)

    4

  • Sq. Ft.

    4692

  • Year Built

    2007

  • $/SqFt

    $586

Zoned for Audubon K-8 and WP High School. MLS#O6190641. PREMIER SOTHEBY'S INTL. REALTY.

Pended $440,000

View Details 21 Photos
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1268

  • Year Built

    1997

  • $/SqFt

    $347

Lawndale - Great location near Advent Health Hospital, Park Avenue, College Park, Rollins, Mead Gardens, and incredible restaurants. MLS#O6190577. LIST RIGHT REALTY.

Home For Sale $2,250,000

View Details 56 Photos
On Market For 25 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3102

  • Year Built

    1989

  • $/SqFt

    $725

Kronenberger - WELCOME HOME to the the Winter Park lifestyle at its finest! MLS#O6181050. FANNIE HILLMAN & ASSOCIATES.

Pended $1,795,000

View Details 58 Photos
On Market For 8 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    4045

  • Year Built

    2004

  • $/SqFt

    $444

Walk to Park Avenue and enjoy all Winter Park has to offer from shopping, restaurants, the farmers market, Albin Polasek Museum & Sculpture Gardens AND Rollins College are just minutes away. Schedule your private showing TODAY~ MLS#O6190155. FANNIE HILLMAN & ASSOCIATES.

Viewing HOMES 1 to 50 of 217

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
$582,536
$439,900
101
2.0%
36.6%
74

Apopka
$506,472
$465,000
459
1.5%
43.8%
81

Belle Isle
$971,264
$859,450
22
4.5%
72.7%
76

Casselberry
$444,253
$425,000
80
5.0%
41.2%
64

Celebration
$1,357,724
$1,150,000
61
0.0%
47.5%
101

Champions Gate
$659,062
$649,900
29
0.0%
37.9%
156

Chuluota
$1,415,952
$595,000
19
0.0%
31.6%
59

Clermont
$576,029
$498,400
588
0.7%
42.3%
91

Gotha
$1,031,940
$539,000
15
0.0%
66.7%
47

Groveland
$474,193
$420,000
186
1.6%
44.6%
74

Harmony
$448,004
$422,500
56
0.0%
44.6%
90

Kissimmee
$537,793
$463,132
1804
0.6%
44.8%
102

Longwood
$763,603
$559,000
165
1.2%
37.0%
65

Maitland
$1,159,262
$667,000
60
0.0%
51.7%
92

Minneola
$548,006
$533,918
116
0.0%
26.7%
79

Montverde
$1,537,586
$1,119,417
59
0.0%
33.9%
126

Ocoee
$558,017
$526,495
118
0.8%
47.5%
76

Orlando
$685,700
$494,945
2250
1.7%
40.7%
91

Oviedo
$684,395
$599,000
143
0.0%
40.6%
57

Poinciana
$333,824
$320,000
485
0.8%
48.5%
113

Reunion
$1,692,737
$1,199,950
96
0.0%
59.4%
176

Saint Cloud
$514,358
$451,495
814
0.4%
43.1%
100

Sanford
$508,580
$424,990
367
1.1%
53.1%
90

Sorrento
$648,900
$467,490
81
0.0%
50.6%
85

Windermere
$2,442,159
$1,495,000
216
1.4%
42.6%
98

Winter Garden
$841,416
$710,000
490
0.0%
38.4%
81

Winter Springs
$552,137
$489,450
116
0.0%
43.1%
63

EasyStreet

Call to Schedule a Showing

(407) 278-2057

(407) 278-2057