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
2886 CAREW AVE, Winter Park, FL 32789
1/37 37

$485,000

Price Dropped by $10K

Single Family Home

4 Beds 3 Baths 1,766 SqFt

2886 CAREW AVE, Winter Park, FL 32789

This charming 4 bedroom home is available now! With lots of open space, a cozy fireplace, and a walk-in closet in the pr...

Listed by OLDE TOWN BROKERS INC

Stellar MLS
407 S LAKEMONT AVE, Winter Park, FL 32792
1/19 19

$475,000

Pending

Single Family Home

3 Beds 1 Bath 1,314 SqFt

407 S LAKEMONT AVE, Winter Park, FL 32792

This adorable 3 bedroom, 1 bath mid-century modern bungalow is tucked into a highly coveted part of Winter Park. Thought...

Listed by TCA REALTY, LLC

Stellar MLS
3001 LITTLE CYPRESS CV, Winter Park, FL 32792
1/41 41

$470,000

Active

Single Family Home

4 Beds 3 Baths 1,906 SqFt

3001 LITTLE CYPRESS CV, Winter Park, FL 32792

Welcome to your dream home in the heart of Winter Parks sought after Hyde Park community. Situated at the end of a quiet...

Listed by PIXEL REALTY

Stellar MLS
1931 OGLESBY AVE, Winter Park, FL 32789
1/79 79

$2,995

Active

Single Family Home

4 Beds 3 Baths 1,650 SqFt

1931 OGLESBY AVE, Winter Park, FL 32789

Location, Location, Location... Offered here is an Amazing Rental with many potential options of usage... 4 Bedrooms and...

Listed by KEEN REALTY GROUP, INC.

Stellar MLS
7628 ALOMA PINES CT, Winter Park, FL 32792
1/17 17

$2,545

Active

Townhouse

3 Beds 3 Baths 1,787 SqFt

7628 ALOMA PINES CT, Winter Park, FL 32792

This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and l...

Listed by REAL PROPERTY MANAGEMENT AND REALTY

Stellar MLS
1966 BISCAYNE DR, Winter Park, FL 32789
1/8 8

$1,950

Pending

Single Family Home

2 Beds 1 Bath 986 SqFt

1966 BISCAYNE DR, Winter Park, FL 32789

This rental is AVAILABLE for move in May 18th 2025! Welcome to Winter Park. This single family home features 2 bedrooms ...

Listed by MAINFRAME REAL ESTATE

Stellar MLS
3007 GEORGE MASON AVE #H-3D, Winter Park, FL 32792
1/19 19

$1,799

Active

Condo

2 Beds 3 Baths 1,090 SqFt

3007 GEORGE MASON AVE #H-3D, Winter Park, FL 32792

Move-in ready and beautifully updated, this two-story condo in the desirable Colonies Community offers 2 bedrooms and 2....

Listed by ALLEGIANT MANAGEMENT GROUP, INC

Stellar MLS
7350 SWALLOW RUN, Winter Park, FL 32792
1/19 19

$1,700

Active

Condo

2 Beds 2 Baths 774 SqFt

7350 SWALLOW RUN, Winter Park, FL 32792

For Rent. Available June 1st. Spacious 2-bedroom, 2-bathroom ground-floor. Features tile flooring throughout, granite co...

Listed by GHALI REALTY, INC

Stellar MLS
2525 VENETIAN WAY, Winter Park, FL 32789
3D

$1,400,000

Active

Single Family Home

3 Beds 3 Baths 1,993 SqFt

2525 VENETIAN WAY, Winter Park, FL 32789

Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access <br>This meticulously renovated 3-bed, 2.5-...

Listed by KELLY PRICE & COMPANY LLC

Stellar MLS
909 SEMINOLE DR, Winter Park, FL 32789
1/50 50

$14,000

Active

Single Family Home

3 Beds 2 Baths 2,009 SqFt

909 SEMINOLE DR, Winter Park, FL 32789

FOR LEASE - STUNNING, COMPLETELY REMODELED BY SKOLFIELD HOMES GUEST HOUSE - IN THE GOLDEN TRIANGLE, WALKING DISTANCE TO...

Listed by KELLY PRICE & COMPANY LLC

Stellar MLS
7429 DANIEL WEBSTER DR #B-15C, Winter Park, FL 32792
3D

$1,100

Active

Condo

1 Bed 1 Bath 809 SqFt

7429 DANIEL WEBSTER DR #B-15C, Winter Park, FL 32792

One or more photo(s) has been virtually staged. Welcome to this charming 1-bedroom, 1-bathroom house located in the desi...

Listed by TRANSCEND REALTY

Stellar MLS
2402.5 TEMPLE DR, Winter Park, FL 32789
1/35 35

$1,899,000

Price Dropped by $201K

Single Family Home

4 Beds 5 Baths 3,248 SqFt

2402.5 TEMPLE DR, Winter Park, FL 32789

Get Busy Living the Winter Park lifestyle in this custom 4-bedroom, 4.5-bathroom pool home tucked away at the end of a 1...

Listed by OLDE TOWN BROKERS INC

Stellar MLS
2105 FOSGATE DR, Winter Park, FL 32789
1/58 58

$1,450,000

Active

Single Family Home

5 Beds 4 Baths 3,068 SqFt

2105 FOSGATE DR, Winter Park, FL 32789

This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to b...

Listed by LPT REALTY, LLC

Stellar MLS
2487 HARBOUR WAY, Winter Park, FL 32792
1/15 15

$340,000

Active

Townhouse

3 Beds 3 Baths 1,803 SqFt

2487 HARBOUR WAY, Winter Park, FL 32792

Unmissable opportunity in Winter Park! <br> <br>Beautiful house for sale with 3 bedrooms and 3 bathrooms, perfect for t...

Listed by WRA BUSINESS & REAL ESTATE

Stellar MLS
1031 WILDMEADOW RUN, Winter Park, FL 32792
1/37 37

$3,950

Pending

Single Family Home

4 Beds 4 Baths 2,589 SqFt

1031 WILDMEADOW RUN, Winter Park, FL 32792

Located in the private, gated community of Hawks Crest, this 4-bedroom, 3.5-bath home built in 2020 offers modern living...

Listed by EXP REALTY LLC

Stellar MLS
2168 MARSH SEDGE LN, Winter Park, FL 32792
1/33 33

$839,000

Active

Single Family Home

4 Beds 3 Baths 2,192 SqFt

2168 MARSH SEDGE LN, Winter Park, FL 32792

Welcome to your future home, where style, comfort, and technology come together seamlessly. This stunning 4-bedroom, 3-b...

Listed by SELECTA REALTY LLC

Stellar MLS
2441 BANCHORY RD, Winter Park, FL 32792
1/26 26

$585,000

Pending

Single Family Home

3 Beds 2 Baths 1,630 SqFt

2441 BANCHORY RD, Winter Park, FL 32792

Under contract-accepting backup offers. Welcome to this beautifully renovated 3-bedroom, 2-bathroom home in the highly d...

Listed by FANNIE HILLMAN & ASSOCIATES

Stellar MLS
264 BALFOUR DR, Winter Park, FL 32792
1/32 32

$400,000

Pending

Townhouse

3 Beds 3 Baths 1,727 SqFt

264 BALFOUR DR, Winter Park, FL 32792

Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart...

Listed by FANNIE HILLMAN & ASSOCIATES

Stellar MLS
1250 S DENNING DR #230, Winter Park, FL 32789
1/16 16

$235,000

Active

Condo

2 Beds 2 Baths 913 SqFt

1250 S DENNING DR #230, Winter Park, FL 32789

Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floo...

Listed by FANNIE HILLMAN & ASSOCIATES

Stellar MLS
316 SCOTTSDALE SQ #316, Winter Park, FL 32792
1/22 22

$120,000

Active

Condo

2 Beds 2 Baths 1,085 SqFt

316 SCOTTSDALE SQ #316, Winter Park, FL 32792

Welcome to 316 Scottsdale Square, a delightful 2-bedroom, 1 and half bathroom condo located in desirable Winter Park. Th...

Listed by JADE KEY REALTY LLC

Stellar MLS
311 E MORSE BLVD #2-3, Winter Park, FL 32789
1/42 42

$6,800

Price Dropped by $1K

Condo

2 Beds 2 Baths 1,964 SqFt

311 E MORSE BLVD #2-3, Winter Park, FL 32789

Enjoy the perfect blend of modern comfort and timeless charm in this beautifully updated 2-bedroom, 2-bathroom condo for...

Listed by CHARLES RUTENBERG REALTY ORLANDO

Stellar MLS
1936 SUMMERFIELD RD, Winter Park, FL 32792
1/59 59

$4,000

Pending

Single Family Home

3 Beds 2 Baths 1,503 SqFt

1936 SUMMERFIELD RD, Winter Park, FL 32792

Welcome to 1936 Summerfield Rd, Winter Park, FL 32792 – a stylish and efficient 3-bedroom, 2-bath home just outside Bald...

Listed by HOST MANAGEMENT GROUP LLC

Stellar MLS
2832 BEAR ISLAND POINTE, Winter Park, FL 32792
1/100 100

$1,165,000

Pending

Single Family Home

5 Beds 5 Baths 3,983 SqFt

2832 BEAR ISLAND POINTE, Winter Park, FL 32792

Under contract-accepting backup offers. Welcome to 2832 Bear Island Pointe in Winter Park's premier gated community, Cyp...

Listed by COMPASS FLORIDA LLC

Stellar MLS
2923 COVE TRL, Winter Park, FL 32789
1/53 53

$1,025,000

Pending

Single Family Home

4 Beds 4 Baths 3,377 SqFt

2923 COVE TRL, Winter Park, FL 32789

Under contract-accepting backup offers. A RARE Winter Park Estate Blending TIMELESS CRAFTSMANSHIP with MODERN FLEXIBILIT...

Listed by KELLER WILLIAMS ADVANTAGE III

Stellar MLS
  • 1
  • ...
  • 4
  • 5
  • 6
  • 7
  • 8
  • ...
  • 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.