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
523 Properties

523 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
490 SHOREVIEW AVE, Winter Park, FL 32789
1/35 35

$599,000

Open Sat 10AM-12PM

Single Family Home

3 Beds 2 Baths 2,266 SqFt

490 SHOREVIEW AVE, Winter Park, FL 32789

Step into timeless elegance with this beautiful 2-story, 3-bed, 2-bath historic home located in one of Winter Park's mos...

Listed by FLORIDA HOME TEAM REALTY LLC

Stellar MLS
2524 SWEETWATER TRL, Winter Park, FL 32789
1/23 23

$625,000

Open Sat 12PM-2PM

Single Family Home

3 Beds 2 Baths 1,728 SqFt

2524 SWEETWATER TRL, Winter Park, FL 32789

WINTER PARK! 32789!! DOMMERICH, MAITLAND MIDDLE, WINTER PARK HIGH!!! Welcome to this one story home with vaulted ceilin...

Listed by FANNIE HILLMAN & ASSOCIATES

Stellar MLS
1401 GREEN COVE RD, Winter Park, FL 32789
1/77 77

$2,900,000

Open Fri 5PM-7PM

Single Family Home

4 Beds 7 Baths 5,416 SqFt

1401 GREEN COVE RD, Winter Park, FL 32789

This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open inte...

Listed by BUCKEYE REALTY LLC

Stellar MLS
3520 BALSAM DR, Winter Park, FL 32792
1/32 32

$425,000

Open Sat 11AM-2PM

Single Family Home

4 Beds 2 Baths 1,468 SqFt

3520 BALSAM DR, Winter Park, FL 32792

WATCH VIDEO TOUR TO SEE MORE --> WWW.TINYURL.COM/3520BalsamDr <br>Welcome to this beautifully updated home that blends...

Listed by EXP REALTY LLC

Stellar MLS
1090 WILDMEADOW RUN, Winter Park, FL 32792
1/42 42

$895,000

Open Sat 11AM-2PM

Single Family Home

4 Beds 4 Baths 2,589 SqFt

1090 WILDMEADOW RUN, Winter Park, FL 32792

One or more photo(s) has been virtually staged. This luxurious Modern Style home delivers the pinnacle lifestyle, in eve...

Listed by BHHS FLORIDA REALTY

Stellar MLS
1399 ALOMA AVE, Winter Park, FL 32789
1/35 35

$675,000

Open Sun 11AM-2PM

Single Family Home

3 Beds 2 Baths 1,804 SqFt

1399 ALOMA AVE, Winter Park, FL 32789

Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is full of timeless charm and unlimited potential! Set on...

Listed by FLORIDA HOMES REALTY & MTG

Stellar MLS
2614 PARKLAND DR, Winter Park, FL 32789
1/77 77

$2,249,999

Open Wed 12:30PM-3PM

Single Family Home

4 Beds 4 Baths 3,307 SqFt

2614 PARKLAND DR, Winter Park, FL 32789

Welcome to 2614 Parkland Drive—an exquisite, fully renovated luxury residence nestled in the heart of Winter Park, Flori...

Listed by JW GASTON LLC

Stellar MLS
1139 FAIRWAY DR, Winter Park, FL 32792
1/44 44

$719,000

Open Sat 12PM-2PM

Single Family Home

4 Beds 2 Baths 2,385 SqFt

1139 FAIRWAY DR, Winter Park, FL 32792

BACK ON MARKET - BUYER'S SALE FELL THRU. PRICE REDUCED, BRING OFFERS. Fabulous updated home in the heart of Winter P...

Listed by KELLER WILLIAMS WINTER PARK

Stellar MLS
7849 GEORGEANN ST, Winter Park, FL 32792
3D

$2,499,900

Open Sat 12PM-2PM

Single Family Home

6 Beds 8 Baths 4,860 SqFt

7849 GEORGEANN ST, Winter Park, FL 32792

BACK ON THE MARKET DUE TO BUYER FINANCING. Price Improvement... BELOW Appraised Value! Lakefront Luxury in Winter Park....

Listed by KELLER WILLIAMS REALTY AT THE PARKS

Stellar MLS
1776 E CHERYL DR, Winter Park, FL 32792
1/14 14

$478,700

Open Sat 2PM-4PM

Single Family Home

4 Beds 2 Baths 2,014 SqFt

1776 E CHERYL DR, Winter Park, FL 32792

Welcome to 1776 E Cheryl Dr, located on a quiet cul-de-sac in desirable Winter Park. The home offers a split plan with 4...

Listed by MINK REALTY

Stellar MLS
5073 LAKE HOWELL RD, Winter Park, FL 32792
3D

$539,500

Open Sat 12PM-3PM

Single Family Home

5 Beds 2 Baths 2,272 SqFt

5073 LAKE HOWELL RD, Winter Park, FL 32792

One or more photo(s) has been virtually staged. Discover this large 5-bedroom, 2-bathroom POOL home in an established Wi...

Listed by CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
3901 WOODGLADE CV, Winter Park, FL 32792
1/42 42

$549,000

Open Sat 12PM-2:30PM

Single Family Home

4 Beds 3 Baths 2,213 SqFt

3901 WOODGLADE CV, Winter Park, FL 32792

New Price Announcement! This STUNNING HOME in Winter Park, now offered at a reduced price, ensures you get exceptional v...

Listed by OLYMPUS EXECUTIVE REALTY INC

Stellar MLS
3458 BALSAM DR, Winter Park, FL 32792
1/12 12

$450,000

Open Sun 11AM-1PM

Single Family Home

3 Beds 2 Baths 1,910 SqFt

3458 BALSAM DR, Winter Park, FL 32792

Seller motivated! Come see this charming 3 bedroom, 2 bath pool home, located in Winter Park, FL. Home is centrally loca...

Listed by CENTURY 21 BE3

Stellar MLS
1608 BOMI CIR, Winter Park, FL 32792
1/30 30

$485,000

Open Sat 11AM-2PM

Single Family Home

3 Beds 2 Baths 1,807 SqFt

1608 BOMI CIR, Winter Park, FL 32792

Welcome to this beautifully upgraded 3-bedroom, 2.5-bathroom single-family home, nestled in the heart of Winter Park, Fl...

Listed by KELLER WILLIAMS ADVANTAGE III REALTY

Stellar MLS
4026 TENITA DR, Winter Park, FL 32792
1/33 33

$518,000

Open Thu 8AM-7PM

Single Family Home

4 Beds 2 Baths 2,122 SqFt

4026 TENITA DR, Winter Park, FL 32792

One or more photo(s) has been virtually staged. Welcome to this stunning property where elegance meets comfort. The neut...

Listed by OPENDOOR BROKERAGE LLC

Stellar MLS
7707 COUNTRY PL, Winter Park, FL 32792
1/25 25

$258,000

Open Sat 12PM-3PM

Condo

2 Beds 2 Baths 1,068 SqFt

7707 COUNTRY PL, Winter Park, FL 32792

RARE FannieMae Approved Condo! Welcome to this beautiful and recently updated single-story condo in the peaceful Goldenr...

Listed by INVESTOR'S REAL ESTATE LLC

Stellar MLS
5240 N LAKE BURKETT LN, Winter Park, FL 32792
1/73 73

$455,000

Open Sat 12PM-3PM

Single Family Home

4 Beds 3 Baths 2,290 SqFt

5240 N LAKE BURKETT LN, Winter Park, FL 32792

Seller offering to cover HOA fees through December 2025! Welcome to 5240 North Lake Burkett Lane, a classic 4 bedroom, 2...

Listed by COLDWELL BANKER REALTY

Stellar MLS
1730 WINCHESTER DR, Winter Park, FL 32789
1/80 80

$3,249,000

Open Sun 2PM-4:30PM

Single Family Home

5 Beds 6 Baths 4,080 SqFt

1730 WINCHESTER DR, Winter Park, FL 32789

Under Construction. Welcome to this exquisite 5-bedroom, 5.5-bathroom home built by Lundev, perfectly situated in the hi...

Listed by KELLER WILLIAMS WINTER PARK

Stellar MLS
185 SYLVAN BLVD, Winter Park, FL 32789
1/8 8

$2,590,000

New

Single Family Home

4 Beds 5 Baths 3,138 SqFt

185 SYLVAN BLVD, Winter Park, FL 32789

Under Construction. Brand-new, meticulously crafted residence built by renowned builder LUIH Homes offering 3,138 square...

Listed by COMPASS FLORIDA LLC

Stellar MLS
1695 LEE RD #E103, Winter Park, FL 32789
1/34 34

$1,900

New

Condo

2 Beds 1 Bath 881 SqFt

1695 LEE RD #E103, Winter Park, FL 32789

One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where ur...

Listed by ROBERT SLACK LLC

Stellar MLS
730 W SWOOPE AVE, Winter Park, FL 32789
1/72 72

$850,000

New

Single Family Home

5 Beds 3 Baths 2,132 SqFt

730 W SWOOPE AVE, Winter Park, FL 32789

One or more photo(s) has been virtually staged. Experience the Charm of Winter Park in This Renovated Corner Home <br>We...

Listed by LPT REALTY, LLC

Stellar MLS
2339 LAFAYETTE AVE, Winter Park, FL 32789
1/63 63

$1,749,000

New

Single Family Home

4 Beds 6 Baths 3,379 SqFt

2339 LAFAYETTE AVE, Winter Park, FL 32789

This Beautiful Winter Park Home is located between the "Vias" and "Tree Streets" for convenient access to highly coveted...

Listed by COLLADO REAL ESTATE

Stellar MLS
1742 WILLA CIR, Winter Park, FL 32792
1/42 42

$520,000

New

Single Family Home

4 Beds 2 Baths 2,313 SqFt

1742 WILLA CIR, Winter Park, FL 32792

some photos are virtually staged!Nestled on one of the largest pie-shaped lots in Willa Grove, this 4-bedroom, 2-bathro...

Listed by CENTURY 21 CARIOTI

Stellar MLS
1308 S PENNSYLVANIA AVE #3, Winter Park, FL 32789
1/18 18

$380,000

New

Condo

1 Bed 1 Bath 823 SqFt

1308 S PENNSYLVANIA AVE #3, Winter Park, FL 32789

Seller offering $10,000 Towards Closing Costs with a full price offer! Sip coffee or tea overlooking lush Mead Gardens f...

Listed by KELLER WILLIAMS CLASSIC

Stellar MLS
  • 1
  • 2
  • 3
  • 4
  • 5
  • ...
  • 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.