Simply Real Estate Simply Real Estate
  • Home
  • Buy
    1. All Listings
    2. Featured Listings
    3. Resources
      1. Mortgage Calculator
      2. Affordability Calculator
  • Sell
    1. Sell My Home
    2. Home Valuation
    3. Market Snapshot
  • Neighborhoods
    1. Ormond Beach
    2. Holly Hill
    3. Daytona Beach
    4. South Daytona
    5. Port Orange
    6. Palm Coast
    7. Flagler Beach
    8. New Smyrna Beach
    9. Edgewater
  • About
    1. About
    2. Past Transactions
  • Contact
  • Register
  • Sign In
Filters Reset
Save Search (2)
Save your search to get Alerts
528 Properties

528 Properties Available In Winter Park

  • Default
  • Price-High To Low
  • Price-Low To High
  • Newest Listings
  • Beds (Most)
  • Baths (Most)
  • Year Built (Newest)
  • Square Feet (Biggest)
Map
Grid
FL >Winter Park >
Market Insights
1265 PARK POINTE LN, Winter Park, FL 32789
1/41 41

$975,000

Pending

Single Family Home

4 Beds 3 Baths 2,295 SqFt

1265 PARK POINTE LN, Winter Park, FL 32789

Welcome home to this beautifully upgraded gem nestled in the heart of Winter Park. This move-in-ready home sits on a qui...

Listed by KELLER WILLIAMS ADVANTAGE III

Stellar MLS
600 BRECHIN DR, Winter Park, FL 32792
1/39 39

$800,000

Pending

Single Family Home

4 Beds 3 Baths 2,360 SqFt

600 BRECHIN DR, Winter Park, FL 32792

Under contract-accepting backup offers. Welcome to one of the most sought after neighborhoods of Kenilworth Shores in Wi...

Listed by KELLER WILLIAMS WINTER PARK

Stellar MLS
7484 CANFORD CT #8, Winter Park, FL 32792
1/32 32

$274,900

Active

Condo

3 Beds 3 Baths 1,578 SqFt

7484 CANFORD CT #8, Winter Park, FL 32792

Beautifully Updated 3-Bedroom Condo with Bonus Room & Modern Amenities. Welcome to this stunningly updated 2-story condo...

Listed by REGENCY REAL ESTATE LLC

Stellar MLS
3310 ROYAL ST, Winter Park, FL 32792
1/31 31

$270,000

Active

Single Family Home

2 Beds 2 Baths 1,036 SqFt

3310 ROYAL ST, Winter Park, FL 32792

Welcome to 3310 Royal Street – a beautifully maintained mid-century gem nestled in one of Winter Park's most desirable n...

Listed by BUY IT INC

Stellar MLS
228 SCOTTSDALE SQ #228, Winter Park, FL 32792
1/17 17

$155,000

Active

Condo

3 Beds 2 Baths 1,250 SqFt

228 SCOTTSDALE SQ #228, Winter Park, FL 32792

Short Sale. Short Sale. Short Sale. SHORT SALE. SHORT SALE, AS IS,Location, Location, Location Winter Park, Excellent op...

Listed by VYLLA HOME

Stellar MLS
2530 FRANKLIN AVE, Winter Park, FL 32789
1/27 27

$3,500

Active

Single Family Home

3 Beds 2 Baths 1,809 SqFt

2530 FRANKLIN AVE, Winter Park, FL 32789

Come and enjoy the comfort and modern upgrades in this beautifully renovated and well-maintained 3-bedroom, 2-bath home,...

Listed by CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
3651 N GOLDENROD RD #107, Winter Park, FL 32792
1/18 18

$1,525

Active

Condo

2 Beds 2 Baths 840 SqFt

3651 N GOLDENROD RD #107, Winter Park, FL 32792

Cozy 2-bedroom 2 2-bath condo located in Winter Park!! Spacious living and dining combo, large kitchen with lots of cabi...

Listed by FLORIDA REALTY INVESTMENTS

Stellar MLS
795 W CANTON AVE, Winter Park, FL 32789
1/61 61

$1,150,000

Pending

Single Family Home

3 Beds 4 Baths 2,374 SqFt

795 W CANTON AVE, Winter Park, FL 32789

Under contract-accepting backup offers. Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just ...

Listed by WEICHERT REALTORS HALLMARK PROPERTIES

Stellar MLS
5275 PINE LILY CIR, Winter Park, FL 32792
1/40 40

$770,000

Price Dropped by $10K

Single Family Home

5 Beds 4 Baths 3,152 SqFt

5275 PINE LILY CIR, Winter Park, FL 32792

Welcome to your private retreat, tucked away on a quiet cul-de-sac with direct pond views. This beautifully upgraded 5-b...

Listed by RE/MAX TOWN & COUNTRY REALTY

Stellar MLS
3601 MIDIRON DR, Winter Park, FL 32789
1/24 24

$499,000

Active

Single Family Home

2 Beds 1 Bath 954 SqFt

3601 MIDIRON DR, Winter Park, FL 32789

BUILD YOUR DREAM HOME IN WINTER PARK! <br>Nestled directly across from the historic Dubsdread Golf Course, this property...

Listed by EMPIRE NETWORK REALTY

Stellar MLS
2812 BRIGHT BIRD LN, Winter Park, FL 32792
1/43 43

$450,000

Price Dropped by $8K

Townhouse

3 Beds 3 Baths 1,907 SqFt

2812 BRIGHT BIRD LN, Winter Park, FL 32792

Built in 2024, this move-in ready 3-bedroom, 2.5-bathroom townhome is located in the gated community of Grayson Square, ...

Listed by EXP REALTY LLC

Stellar MLS
200 SAINT ANDREWS BLVD #2306, Winter Park, FL 32792
1/11 11

$249,900

Active

Condo

2 Beds 2 Baths 1,015 SqFt

200 SAINT ANDREWS BLVD #2306, Winter Park, FL 32792

Excellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-bath corner unit is in the Four...

Listed by CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
2405 PASSAMONTE DR #1A, Winter Park, FL 32792
1/22 22

$2,350

Pending

Townhouse

3 Beds 3 Baths 1,765 SqFt

2405 PASSAMONTE DR #1A, Winter Park, FL 32792

Discover easy living in this delightful 1700+ sq ft condominium in VIA LAGO AT HANGING MOSS. This beautiful 3 bedroom, 2...

Listed by ZP REALTY GROUP

Stellar MLS
7341 DANIEL WEBSTER DR #D, Winter Park, FL 32792
1/20 20

$990

Active

Condo

1 Bed 1 Bath 581 SqFt

7341 DANIEL WEBSTER DR #D, Winter Park, FL 32792

One or more photo(s) has been virtually staged. Welcome to your new home in Winter Park, FL! This spacious and convenien...

Listed by TRANSCEND REALTY

Stellar MLS
1795 GREENWICH AVE, Winter Park, FL 32789
1/77 77

$2,490,000

Price Dropped by $85K

Single Family Home

5 Beds 6 Baths 3,852 SqFt

1795 GREENWICH AVE, Winter Park, FL 32789

Welcome to a one-of-a-kind, custom-designed residence offering the perfect blend of modern sophistication, thoughtful fu...

Listed by KELLY PRICE & COMPANY LLC

Stellar MLS
2907 SUMMERFIELD RD, Winter Park, FL 32792
1/32 32

$749,000

Pending

Single Family Home

5 Beds 2 Baths 2,532 SqFt

2907 SUMMERFIELD RD, Winter Park, FL 32792

Under contract-accepting backup offers. Just in time for summer! Here's the trifecta of size, location, and condition th...

Listed by MILLER GRANT AND COMPANY

Stellar MLS
225 E CANTON AVE #225, Winter Park, FL 32789
1/26 26

$649,000

Active

Condo

2 Beds 2 Baths 1,057 SqFt

225 E CANTON AVE #225, Winter Park, FL 32789

This beautifully updated 2-bedroom, 2-bathroom corner unit is located in the highly desirable Winterset Condominiums on ...

Listed by PALMANO GROUP RE BROKERAGE LLC

Stellar MLS
2348 SUN VALLEY CIR, Winter Park, FL 32792
1/31 31

$214,900

Pending

Condo

2 Beds 2 Baths 1,173 SqFt

2348 SUN VALLEY CIR, Winter Park, FL 32792

Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Dreams Do Come True! Spectacular...

Listed by INVESTOR'S REAL ESTATE LLC

Stellar MLS
1000 S SEMORAN BLVD #306, Winter Park, FL 32792
1/13 13

$157,000

Active

Condo

1 Bed 1 Bath 796 SqFt

1000 S SEMORAN BLVD #306, Winter Park, FL 32792

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currentl...

Listed by KIMBRIDGE REALTY, LLC

Stellar MLS
1000 S SEMORAN BLVD #404, Winter Park, FL 32792
1/6 6

$157,000

Active

Condo

1 Bed 1 Bath 776 SqFt

1000 S SEMORAN BLVD #404, Winter Park, FL 32792

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currentl...

Listed by KIMBRIDGE REALTY, LLC

Stellar MLS
1000 S SEMORAN BLVD #408, Winter Park, FL 32792
1/12 12

$157,000

Active

Condo

1 Bed 1 Bath 776 SqFt

1000 S SEMORAN BLVD #408, Winter Park, FL 32792

Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Spacious Other units currentl...

Listed by KIMBRIDGE REALTY, LLC

Stellar MLS
7336 DANIEL WEBSTER DR #9, Winter Park, FL 32792
1/17 17

$134,900

Pending

Condo

2 Beds 3 Baths 1,090 SqFt

7336 DANIEL WEBSTER DR #9, Winter Park, FL 32792

Under contract-accepting backup offers. Whether you're looking for a savvy investment or your next personal home, this s...

Listed by MAINFRAME REAL ESTATE

Stellar MLS
2749 BRIGHT BIRD LN, Winter Park, FL 32792
1/9 9

$2,800

Active

Townhouse

3 Beds 3 Baths 1,700 SqFt

2749 BRIGHT BIRD LN, Winter Park, FL 32792

Like New! Townhouse in a very calm and central community in Winter Park, excellent schools, great location! Clubhouse wi...

Listed by REALTY ONE GROUP EVOLUTION

Stellar MLS
3651 N GOLDENROD RD #B207, Winter Park, FL 32792
1/18 18

$1,650

Active

Condo

2 Beds 2 Baths 840 SqFt

3651 N GOLDENROD RD #B207, Winter Park, FL 32792

Beautifully Updated 2-Bed/2-Bath Condo Near UCF & Full Sail! <br> <br>Step into this stylish and freshly updated second-...

Listed by MAINFRAME REAL ESTATE

Stellar MLS
  • 1
  • ...
  • 5
  • 6
  • 7
  • 8
  • 9
  • ...
  • 22

explore listings in Winter Park

  • Open House
  • Price Reduced
  • Virtual Tour
  • 3D Tour
ChrissyLogo1
Simply Real Estate
Chrissy Fabian | License ID: BK3217104
73 W. Granada Blvd, Ormond Beach, Florida 32174 USA

+1(386) 299-3026

chrissy@simplyrefl.com

Get My App

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.

ChrissyLogo1
Simply Real Estate
Chrissy Fabian | License ID: BK3217104
73 W. Granada Blvd, Ormond Beach, Florida 32174 USA

+1(386) 299-3026

chrissy@simplyrefl.com

Get My App

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2025. All Rights Reserved.