28 Results

Winter Park Homes For Sale & Winter Park FL Real Estate from $500K - $600K

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 For 3 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 $550,000

View 2731 Tierra Cir Winter Park FL
View Details 34 Photos
View 2731 Tierra Cir Winter Park FL
View 2731 Tierra Cir Winter Park FL
View 2731 Tierra Cir Winter Park FL
On Market For 10 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 4160 Waterview Loop Winter Park FL
View Details 84 Photos
View 4160 Waterview Loop Winter Park FL
View 4160 Waterview Loop Winter Park FL
View 4160 Waterview Loop Winter Park FL
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 $548,997

View 2703 Summerfield Rd Winter Park FL
View Details 34 Photos
View 2703 Summerfield Rd Winter Park FL
View 2703 Summerfield Rd Winter Park FL
View 2703 Summerfield Rd Winter Park FL
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 $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.

Home For Sale $525,000

View Details 39 Photos
On Market For 22 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.

Pended $539,000

View Details 38 Photos
On Market For 2 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1599

  • Year Built

    1969

  • $/SqFt

    $337

This home offers exceptional features, a fabulous Florida lifestyle and a great location close to everything, tucked away in a safe and quiet neighborhood. MLS#FC299361. PALM WAVE REALTY.

Home For Sale $539,900

Reduced By $10,100
View Details 35 Photos
On Market For 32 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2197

  • Year Built

    1963

  • $/SqFt

    $246

Don't let this opportunity pass you by, call and arrange for your private showing today! MLS#O6188237. KELLER WILLIAMS WINTER PARK.

Home For Sale $520,000

Reduced By $15,000
View Details 44 Photos
On Market For 40 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1878

  • Year Built

    1979

  • $/SqFt

    $277

35 minutes from UNIVERSAL & DISNEY and only an hour from the BEACH, allowing you to enjoy the best of both worlds, luxury living and prime location. MLS#O6186883. RE/MAX 200 REALTY.

Pended $540,000

View Details 34 Photos
*POTENTIAL GREAT VALUE
On Market For 11 Days

  • Bedrooms

    5

  • Full Bath(s)

    3

  • Sq. Ft.

    2917

  • Year Built

    1984

  • $/SqFt

    $185

Amberwood - Recent Updates: New Roof (2021), New Hvac Systems (2022), Repipe (2021), Pool Motor (2024), De Pool Filter (2021), Garage Door Opener (2023). MLS#O6186685. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $599,900

Reduced By $60,000
View Details 38 Photos
On Market For 41 Days

  • Bedrooms

    3

  • Full Bath(s)

    1

  • Sq. Ft.

    2130

  • Year Built

    1957

  • $/SqFt

    $282

Kenilworth Shores - This gem won't last long...come see it today! MLS#O6185836. SAND DOLLAR REALTY GROUP INC.

Pended $525,000

View Details 23 Photos
On Market For 14 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1620

  • Year Built

    1963

  • $/SqFt

    $324

Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High, this home offers a practical and comfortable Winter Park lifestyle opportunity. MLS#O6185671. FANNIE HILLMAN & ASSOCIATES.

Pended $574,000

Reduced By $25,000
View Details 49 Photos
On Market For 12 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2332

  • Year Built

    1970

  • $/SqFt

    $246

Schedule your showing today and make this dream home yours! MLS#O6184974. RE/MAX TOWN & COUNTRY REALTY.

Home For Sale $544,000

Reduced By $5,000
View Details 36 Photos
On Market For 46 Days

  • Bedrooms

    5

  • Full Bath(s)

    2

  • Sq. Ft.

    2188

  • Year Built

    1972

  • $/SqFt

    $249

Arrowhead Cove - Please see MLS for full list of upgrades. MLS#O6185134. AFFINITY REALTY LLC.

Pended $589,900

View Details 35 Photos
On Market For 4 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1788

  • Year Built

    1964

  • $/SqFt

    $330

Start packing your bags, cause your gonna love this one! MLS#O6184679. J. SCOTT JONES, REALTOR.

Home For Sale $549,900

Reduced By $15,000
View Details 42 Photos
On Market For 50 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2188

  • Year Built

    1993

  • $/SqFt

    $251

Enjoy easy access to conveniences in every direction.Homes in this community are rare to come by – seize the opportunity to call this place home! MLS#O6183732. FANNIE HILLMAN & ASSOCIATES.

Home For Sale $549,000

View Details 9 Photos
On Market For 54 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    1570

  • Year Built

    1948

  • $/SqFt

    $350

Buyer is responsible for doing any research and contacting the city of Winter Park on splits, zoning, building codes, permits, etc. MLS#O6182627. RE/MAX 200 REALTY.

Pended $525,000

View Details 19 Photos
On Market For 47 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    1509

  • Year Built

    1958

  • $/SqFt

    $348

Photographs are representative of the property with no furnishings. MLS#O6177655. COLDWELL BANKER REALTY.

Home For Sale $550,000

View Details 20 Photos
*POTENTIAL GREAT VALUE
On Market For 84 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    1920

  • Year Built

    1981

  • $/SqFt

    $286

It can also be used as a duplex for 1 bedroom 1 bathroom with living room at downstairs and 2 bed 2 bath with family room at upstairs and kitchen at outside porch. Nice neighborhood, No HOA MLS#O6174105. GOLDEN SUN REALTY INC.

Home For Sale $549,000

Reduced By $80,000
View Details 49 Photos
*POTENTIAL GREAT VALUE
On Market For 92 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2258

  • Year Built

    1948

  • $/SqFt

    $243

Glencoe - The Property Is Located Near The Quaint Shopping And Dining Area Or Winter Park Close To Interstate Shopping Dining And Local Attractions MLS#O6172105. PR REAL ESTATE SERVICES.

Pended $550,000

View Details 41 Photos
On Market For 13 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1917

  • Year Built

    1977

  • $/SqFt

    $287

Lake Waunatta Woods - The location of the home provides convenient traveling to multiple grocery stores, State Road 417, the University of Central Florida, Full Sail University, downtown Winter Park, and Downtown Orlando! MLS#O6171602. KELLER WILLIAMS REALTY AT THE PARKS.

Home For Sale $569,900

Reduced By $10,000
View Details 26 Photos
On Market For 102 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2279

  • Year Built

    1965

  • $/SqFt

    $250

Winter Park Estates - Come and view this beautifully remodeled home in the Winter Park area. MLS#T3496399. PAULINO GLOBAL REAL ESTATE.

Home For Sale $569,900

Reduced By $10,000
View Details 39 Photos
On Market For 148 Days

  • Bedrooms

    4

  • Full Bath(s)

    2

  • Sq. Ft.

    2300

  • Year Built

    1987

  • $/SqFt

    $248

The owner has been meticulous in the maintenance of this home. MLS#O6156969. COLDWELL BANKER REALTY.

Home For Sale $599,999

View Details 34 Photos
On Market For 151 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2340

  • Year Built

    1971

  • $/SqFt

    $256

Arrowhead Cove - Experience peace of mind with a newer roof (2017), new cabinets, new flooring, new plumbing, new AC ducts, and new electrical throughout the entire home. MLS#O6159358. PARK PLACE REAL ESTATE.

Home For Sale $510,000

Reduced By $50,000
View Details 54 Photos
On Market For 206 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1668

  • Year Built

    1953

  • $/SqFt

    $306

Schedule your showing today and come see for yourself. MLS#S5092216. MAXIM REALTY ORLANDO.

Pended $562,000

Reduced By $88,000
View Details 45 Photos
On Market For 54 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1778

  • Year Built

    1956

  • $/SqFt

    $316

Tanglewood - Refreshing. Peaceful. Happy. Inviting. Private. Convenient. MLS#O6137445. CADENCE LIFESTYLE REAL ESTATE.

Home For Sale $574,900

Reduced By $179,100
View Details 17 Photos
*IS BANK OWNED
On Market For 312 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1808

  • Year Built

    1956

  • $/SqFt

    $318

Sylvan Heights - A technology fee will apply to the buyer’s agent agent upon consummation of a sale. MLS#O6115763. ABC REAL ESTATE SERVICES.

Home For Sale $599,000

View Details 15 Photos
On Market For 404 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    1805

  • Year Built

    1959

  • $/SqFt

    $332

Winter Park Estates - *All information is intended to be accurate but is not guaranteed. MLS#O6093816. COLDWELL BANKER REALTY.

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Viewing HOMES 1 to 28 of 28

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
$579,233
$439,900
103
1.9%
35.9%
74

Apopka
$507,123
$464,950
464
1.5%
43.8%
80

Belle Isle
$936,491
$760,450
22
4.5%
68.2%
70

Casselberry
$445,528
$425,000
81
4.9%
40.7%
65

Celebration
$1,358,212
$1,172,500
62
0.0%
46.8%
101

Champions Gate
$659,062
$649,900
29
0.0%
37.9%
157

Chuluota
$1,378,222
$591,250
18
0.0%
33.3%
57

Clermont
$573,869
$498,800
593
0.7%
42.3%
91

Gotha
$1,031,940
$539,000
15
0.0%
66.7%
48

Groveland
$473,120
$420,000
187
1.6%
44.4%
73

Harmony
$441,647
$422,500
56
0.0%
46.4%
83

Kissimmee
$536,295
$463,999
1817
0.7%
44.7%
101

Longwood
$763,213
$564,900
171
1.2%
37.4%
64

Maitland
$1,127,958
$659,000
63
0.0%
49.2%
89

Minneola
$548,919
$533,918
114
0.0%
26.3%
80

Montverde
$1,537,586
$1,119,417
59
0.0%
33.9%
127

Ocoee
$556,547
$526,495
122
0.8%
45.9%
74

Orlando
$687,215
$495,000
2283
1.7%
40.3%
90

Oviedo
$682,216
$599,900
151
0.0%
39.1%
55

Poinciana
$333,741
$320,000
485
0.8%
48.0%
113

Reunion
$1,692,101
$1,199,950
96
0.0%
60.4%
177

Saint Cloud
$513,751
$450,442
814
0.4%
43.6%
101

Sanford
$511,385
$424,995
370
1.1%
53.2%
90

Sorrento
$648,838
$467,490
81
0.0%
51.9%
86

Windermere
$2,425,093
$1,495,000
219
1.4%
43.4%
97

Winter Garden
$841,140
$713,450
500
0.2%
38.0%
80

Winter Springs
$556,438
$496,750
122
0.0%
40.2%
60

EasyStreet

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