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Winter Park Condos For Sale & Winter Park FL Real Estate

Condo For Sale $449,000

View 1323 Merrydale Way Winter Park FL
View Details 31 Photos
View 1323 Merrydale Way Winter Park FL
View 1323 Merrydale Way Winter Park FL
View 1323 Merrydale Way Winter Park FL
On Market Today

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1964

  • Year Built

    2021

  • $/SqFt

    $229

Enclave At Hawks Crest - With excellent schools, vibrant local businesses, and endless amenities, this home offers both convenience and community. MLS#O6258940. EXP REALTY LLC.

Condo For Sale $200,000

View 1000 S Semoran Blvd # 815 Winter Park FL
View Details 25 Photos
View 1000 S Semoran Blvd # 815 Winter Park FL
View 1000 S Semoran Blvd # 815 Winter Park FL
View 1000 S Semoran Blvd # 815 Winter Park FL
On Market Today

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1003

  • Year Built

    1969

  • $/SqFt

    $199

Golfside - Whether you're seeking convenience or a cozy retreat, this condo offers everything you need! MLS#O6259572. WATSON REALTY CORP.

Condo For Sale $170,000

View 311 Sandlewood Trl # 4 Winter Park FL
View Details 8 Photos
View 311 Sandlewood Trl # 4 Winter Park FL
View 311 Sandlewood Trl # 4 Winter Park FL
View 311 Sandlewood Trl # 4 Winter Park FL
*POTENTIAL GREAT VALUE
On Market Today

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    980

  • Year Built

    1984

  • $/SqFt

    $173

Act fast — schedule your private showing today! MLS#O6259730. KELLER WILLIAMS REALTY AT THE PARKS.

Condo For Sale $235,000

View 667 Montego Bay Ct # S Winter Park FL
View Details 21 Photos
View 667 Montego Bay Ct # S Winter Park FL
View 667 Montego Bay Ct # S Winter Park FL
View 667 Montego Bay Ct # S Winter Park FL
On Market For 4 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1120

  • Year Built

    1981

  • $/SqFt

    $210

Winter Park Villas - This is a gorgeous, well-kept community and this home is ready for its next homeowner! MLS#O6257948. RE/MAX TOWN & COUNTRY REALTY.

Condo For Sale $225,000

View Details 27 Photos
On Market For 5 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1031

  • Year Built

    1984

  • $/SqFt

    $218

Don't wait – schedule your showing today before it's gone! MLS#O6257246. THE REAL ESTATE COLLECTION LLC.

Condo For Sale $125,000

View Details 30 Photos
On Market For 5 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    785

  • Year Built

    1974

  • $/SqFt

    $159

Known for beautiful neighborhoods, excellent schools, and various recreational activities, living in Winter Park provides a perfect balance of comfort and convenience. MLS#S5115907. FLORIDA HOMES REALTY & MORTGAGE.

Condo For Sale $2,395,000

View Details 48 Photos
*POTENTIAL GREAT VALUE
On Market For 8 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2632

  • Year Built

    1999

  • $/SqFt

    $910

A rare opportunity for the most discerning buyer. MLS#O6257901. PREMIER SOTHEBY'S INTL. REALTY.

Condo For Sale $214,900

View Details 15 Photos
On Market For 7 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1049

  • Year Built

    1969

  • $/SqFt

    $205

Golfside - Make it yours or invest to rent. MLS#O6258290. COLDWELL BANKER RESIDENTIAL RE.

Condo For Sale $499,000

View Details 30 Photos
On Market For 9 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1328

  • Year Built

    1969

  • $/SqFt

    $376

The HOA fee covers water, cable, and internet. MLS#O6257677. PALMANO GROUP RE BROKERAGE LLC.

Condo For Sale $473,700

View Details 22 Photos
*POTENTIAL GREAT VALUE
On Market For 9 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1820

  • Year Built

    1991

  • $/SqFt

    $260

This thoughtfully designed home is move-in ready and offers modern updates, timeless charm, and ultimate convenience in the heart of Winter Park just two minutes away from Whole Foods and minutes away from Park Avenue! MLS#S5115699. KELLER WILLIAMS REALTY AT THE LAKES.

Condo For Sale $249,900

View Details 57 Photos
On Market For 9 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1281

  • Year Built

    1973

  • $/SqFt

    $195

Wrenwood Heights - Don’t miss your chance to make this beautiful condo your new home! MLS#O6257765. FLORIDA REALTY MARKETPLACE.

Condo For Sale $725,000

View Details 20 Photos
*POTENTIAL GREAT VALUE
On Market For 11 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    2317

  • Year Built

    2014

  • $/SqFt

    $313

Spacious and open floor plan with 4 bedrooms and 3.5 baths. MLS#O6257130. COLDWELL BANKER RESIDENTIAL RE.

Condo For Sale $245,000

View Details 26 Photos
On Market For 11 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    808

  • Year Built

    1984

  • $/SqFt

    $303

Don’t miss your opportunity to see this beautifully updated condo in one of Winter Park’s most desirable areas. Schedule your private tour today! MLS#O6257241. CREEGAN GROUP.

Condo For Sale $195,000

View Details 16 Photos
On Market For 13 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    840

  • Year Built

    1990

  • $/SqFt

    $232

You will also be zoned for Winter Park high school! Come take a look today! MLS#O6256664. EXP REALTY LLC.

Condo For Sale $175,000

View Details 16 Photos
On Market For 15 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    678

  • Year Built

    1973

  • $/SqFt

    $258

Located 20 minutes from University of Central Florida and Valencia College. MLS#O6256033. UNITED REALTY GROUP INC.

Condo For Sale $164,900

View Details 21 Photos
On Market For 15 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1030

  • Year Built

    1974

  • $/SqFt

    $160

Colonies - Don’t miss this stylish, move-in-ready condo! MLS#O6256375. GRAVES REALTY.

Condo For Sale $1,695,000

View Details 37 Photos
*POTENTIAL GREAT VALUE
On Market For 16 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    3174

  • Year Built

    2009

  • $/SqFt

    $534

Step just outside, you’ll discover a vast selection of fine dining and shopping, and cultural options encapsulating the essence of urban convenience combined with a charming neighborhood feel. MLS#O6256094. PREMIER SOTHEBY'S INTL. REALTY.

Condo For Sale $395,000

View Details 19 Photos
On Market For 15 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    726

  • Year Built

    1972

  • $/SqFt

    $544

Offered by Holt Home Team for under $400,000 in Downtown Winter park. MLS#O6256275. HOLT REAL ESTATE LLC.

Condo For Sale $250,000

View Details 23 Photos
On Market For 16 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1316

  • Year Built

    1980

  • $/SqFt

    $190

2/2 Condo MLS#O6251296. MARK SPAIN REAL ESTATE.

Condo For Sale $250,000

View Details 29 Photos
*POTENTIAL GREAT VALUE
On Market For 17 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1611

  • Year Built

    1974

  • $/SqFt

    $155

Don’t miss out on this opportunity! MLS#O6253905. NETWORTH REALTY OF ORLANDO, LLC.

Condo For Sale $139,000

Reduced By $10,000
View Details 20 Photos
On Market For 17 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1085

  • Year Built

    1974

  • $/SqFt

    $128

Winter Park Woods - Don’t miss out on the opportunity to make this condo yours – schedule a showing today! MLS#O6255508. COLDWELL BANKER REALTY.

Pended $130,000

View Details 23 Photos
On Market For 17 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1088

  • Year Built

    1974

  • $/SqFt

    $119

Situated close to UCF, Full Sail University, and just minutes from shopping malls, major highways, restaurants, and theme parks, this condo provides easy access to everything you need—including Orlando International Airport, just 11 minutes away. MLS#O6252352. CONTINENTAL INVT INT'L NETWORK.

Pended $269,900

View Details 26 Photos
On Market For 18 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1038

  • Year Built

    1981

  • $/SqFt

    $260

Villas Of Casselberry - With an ultra-low HOA fee of approximately $55 per month, including access to the community pool, this townhome is not only an incredible place to live but also a smart investment opportunity. Hurry on this one. MLS#O6254807. INVESTOR'S REAL ESTATE LLC.

Condo For Sale $235,000

Reduced By $10,000
View Details 30 Photos
On Market For 20 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1117

  • Year Built

    1984

  • $/SqFt

    $210

Hidden Oaks - Schedule a showing today and make this enchanting space your new home! MLS#O6253625. COLDWELL BANKER RESIDENTIAL RE.

Pended $197,000

View Details 24 Photos
On Market For 11 Days

  • Bedrooms

    0

  • Full Bath(s)

    1

  • Sq. Ft.

    624

  • Year Built

    1964

  • $/SqFt

    $316

Come take a look, you'll never want to leave! MLS#O6253125. PARK PLACE REAL ESTATE.

Condo For Sale $189,900

View Details 10 Photos
On Market For 20 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    840

  • Year Built

    1990

  • $/SqFt

    $226

Call now for your private showing, will not last. MLS#O6254613. CFRP REALTY LLC.

Pended $1,325,000

View Details 44 Photos
*POTENTIAL GREAT VALUE
On Market For 3 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2314

  • Year Built

    2023

  • $/SqFt

    $573

Experience the pinnacle of elegance and comfort in this prime Central Florida location—your dream home awaits! MLS#O6252328. COLDWELL BANKER RESIDENTIAL RE.

Condo For Sale $160,000

View Details 21 Photos
On Market For 22 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1020

  • Year Built

    1974

  • $/SqFt

    $157

Winter Park Woods - Hurry today for this won't be in the market for long. MLS#S5114886. GLOVEN REALTY.

Condo For Sale $719,900

Reduced By $5,100
View Details 43 Photos
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    3

  • Sq. Ft.

    2016

  • Year Built

    2018

  • $/SqFt

    $357

Don’t miss out on this exceptional value—schedule a viewing today and discover the potential that awaits in this Winter Park townhome! MLS#O6248830. COLDWELL BANKER RESIDENTIAL RE.

Pended $469,900

View Details 46 Photos
On Market For 24 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1964

  • Year Built

    2020

  • $/SqFt

    $239

Enclave At Hawks Crest - Don’t miss this opportunity to own your dream home in this wonderful community—schedule your showing today! MLS#O6248700. COLDWELL BANKER RESIDENTIAL RE.

Pended $310,000

View Details 46 Photos
On Market For 25 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1284

  • Year Built

    1979

  • $/SqFt

    $241

Windward Square - Don’t miss the chance to make this townhome your new sanctuary! MLS#OM688672. FLORIDA'S CHOICE REALTY.

Pended $250,000

View Details 35 Photos
On Market For 25 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1266

  • Year Built

    1970

  • $/SqFt

    $197

Enjoy easy access to Winter Park’s shopping, dining, and cultural scenes—making this condo a true gem in one of Central Florida’s most vibrant communities! Schedule your showing today! MLS#O6253379. KELLER WILLIAMS REALTY AT THE PARKS.

Condo For Sale $199,900

View Details 22 Photos
On Market For 26 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    787

  • Year Built

    1964

  • $/SqFt

    $254

This property is a must-see to truly appreciate its charm and amenities. MLS#O6253203. HOMEVEST REALTY.

Condo For Sale $454,990

View Details 58 Photos
On Market For 27 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1907

  • Year Built

    2023

  • $/SqFt

    $239

15 min to famous shopping and dining on Park Ave. Don't miss out on this incredible opportunity to make Grayson Square your new home in beautiful Winter Park! HABLO ESPAÑOL. MLS#O6252450. LPT REALTY.

Condo For Sale $139,000

View Details 26 Photos
On Market For 30 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    803

  • Year Built

    1974

  • $/SqFt

    $173

Colonies - Make your appointment quick this apartment is ready to move in. MLS#S5114398. TBO REAL ESTATE PARTNERS INC.

Pended $499,000

View Details 33 Photos
On Market For 30 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    2312

  • Year Built

    2021

  • $/SqFt

    $216

Enclave At Hawks Crest - Roof - 2021  hvac - 2021  plumbing - 2021 Electric - 2021 MLS#O6251196. KELLER WILLIAMS WINTER PARK.

Condo For Sale $487,500

View Details 32 Photos
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1755

  • Year Built

    2020

  • $/SqFt

    $278

Enclave At Hawks Crest - Roof - 2020, Hvac - 2020, Plumbing - 2020, Electric - 2020 MLS#O6251457. KELLER WILLIAMS WINTER PARK.

Pended $318,888

View Details 33 Photos
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1374

  • Year Built

    1986

  • $/SqFt

    $232

Winter Park Pines - MLS#O6251997. LA ROSA REALTY ORLANDO LLC.

Condo For Sale $298,000

View Details 27 Photos
*POTENTIAL GREAT VALUE
On Market For 30 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1698

  • Year Built

    1984

  • $/SqFt

    $176

Cedarwood Village - Don’t miss your chance to experience this inviting community and make this charming condo your new home! MLS#O6252111. COTTAGE REALTY INC.

Condo For Sale $200,000

Reduced By $10,000
View Details 37 Photos
On Market For 31 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    927

  • Year Built

    1973

  • $/SqFt

    $216

Schedule your viewing today and come see why this should be your next home! MLS#O6251967. MORGAN PROPERTY SOLUTIONS INC.

Pended $675,000

View Details 34 Photos
*POTENTIAL GREAT VALUE
On Market For 31 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1785

  • Year Built

    1983

  • $/SqFt

    $378

Enjoy a low-maintenance lifestyle in a prime location! MLS#O6251209. FANNIE HILLMAN & ASSOCIATES.

Pended $229,000

View Details 29 Photos
On Market For 29 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1037

  • Year Built

    1981

  • $/SqFt

    $221

Winter Park Villas - The HOA takes care of the roof and all exterior building maintenance, plus includes water/trash/sewer and community amenities such as a beautiful pond with walking trail, pet cleanup stations, tennis courts and a fabulous swimming pool! MLS#O6244402. RE/MAX TOWN & COUNTRY REALTY.

Condo For Sale $199,000

Reduced By $10,000
View Details 20 Photos
On Market For 32 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    582

  • Year Built

    1960

  • $/SqFt

    $342

Don't miss your opportunity to live in this coveted Winter Park location. MLS#O6250765. EXP REALTY LLC.

Condo For Sale $384,400

View Details 28 Photos
*POTENTIAL GREAT VALUE
On Market For 34 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1536

  • Year Built

    1986

  • $/SqFt

    $250

Current tenant has flexibility in moving. MLS#O6249823. MICHAEL O'SHAUGHNESSY, INC..

Condo For Sale $199,999

Reduced By $5,001
View Details 20 Photos
On Market For 34 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    840

  • Year Built

    1990

  • $/SqFt

    $238

Don't miss the opportunity to own this beautiful condo in a central location. MLS#W7869224. LISTWITHFREEDOM.COM.

Pended $1,995,000

View Details 40 Photos
*POTENTIAL GREAT VALUE
On Market For 37 Days

  • Bedrooms

    4

  • Full Bath(s)

    3

  • Sq. Ft.

    3328

  • Year Built

    2018

  • $/SqFt

    $599

Ideal for those seeking a low-maintenance, lock-and-leave lifestyle with all conveniences of urban living! MLS#O6249199. PREMIER SOTHEBY'S INTL. REALTY.

Condo For Sale $469,900

Reduced By $10,100
View Details 34 Photos
On Market For 37 Days

  • Bedrooms

    3

  • Full Bath(s)

    2

  • Sq. Ft.

    1756

  • Year Built

    2022

  • $/SqFt

    $268

Enclave At Hawks Crest - Owner financing available at below market interest rate. MLS#O6250396. KELLER WILLIAMS WINTER PARK.

Condo For Sale $245,000

Reduced By $10,000
View Details 41 Photos
On Market For 37 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1365

  • Year Built

    1974

  • $/SqFt

    $179

Exterior features include an oversized carport with spacious storage unit.Great condo for owner occupant or investment property! MLS#S5114106. CHARLES RUTENBERG REALTY ORLANDO.

Pended $230,000

View Details 19 Photos
On Market For 37 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1120

  • Year Built

    1981

  • $/SqFt

    $205

This won't last long! Schedule your showing today! MLS#O6246779. RE/MAX INNOVATION.

Condo For Sale $135,000

View Details 17 Photos
On Market For 38 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    664

  • Year Built

    1974

  • $/SqFt

    $203

Don’t miss the opportunity to own this fully renovated condo in a prime Winter Park location—schedule your showing today MLS#V4938408. CENTURY 21 MCBRIDE REALTY GROUP.

Viewing CONDOS 1 to 50 of 155

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 407-485-1814 and speak with one of our real estate consultants.

Popular Condos

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$214,165
$205,000
233
0.4%
58.8%
110

Apopka
$336,504
$349,490
184
1.1%
49.5%
84

Belle Isle
$197,450
$197,450
2
0.0%
100.0%
192

Casselberry
$241,711
$259,999
59
1.7%
55.9%
66

Celebration
$480,416
$455,000
62
1.6%
45.2%
97

Champions Gate
$376,966
$372,324
16
0.0%
56.2%
130

Clermont
$375,238
$358,215
105
0.0%
37.1%
87

Gotha
$280,000
$280,000
1
0.0%
100.0%
102

Groveland
$332,361
$334,900
18
0.0%
44.4%
63

Harmony
$290,898
$279,900
11
9.1%
81.8%
112

Kissimmee
$359,686
$349,000
1169
0.7%
44.8%
121

Longwood
$290,987
$297,000
55
0.0%
56.4%
71

Maitland
$302,953
$285,000
49
0.0%
44.9%
78

Montverde
$403,300
$409,900
3
0.0%
33.3%
117

Ocoee
$339,913
$330,000
21
0.0%
61.9%
90

Orlando
$304,903
$248,500
1499
0.5%
51.0%
102

Oviedo
$565,917
$456,900
64
0.0%
32.8%
106

Poinciana
$279,515
$288,450
24
0.0%
58.3%
151

Reunion
$403,088
$375,000
106
0.9%
55.7%
143

Saint Cloud
$344,588
$340,000
241
0.4%
46.9%
89

Sanford
$301,711
$292,450
104
0.0%
55.8%
67

Sorrento
$310,000
$305,000
3
0.0%
33.3%
102

Windermere
$411,279
$416,500
52
0.0%
44.2%
76

Winter Garden
$433,880
$447,990
164
0.0%
45.1%
100

Winter Springs
$343,060
$340,000
59
0.0%
45.8%
84

EasyStreet

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