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31 Properties

31 Properties Available In Winter Park

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FL >Winter Park >
Market Insights
1660 ORANGE AVE, Winter Park, FL 32789
1/61 61

$479,900

Open Sat 1PM-3PM

Single Family Home

3 Beds 2 Baths 1,614 SqFt

1660 ORANGE AVE, Winter Park, FL 32789

Don't miss this wonderful opportunity to own a 3-bedroom, 2-bath home in the desirable Orwin Manor area of Winter Park, ...

Listed by Gaby Murillo EXP REALTY LLC

Stellar MLS
1211 SCHULTZ AVE, Winter Park, FL 32789
1/35 35

$475,000

Open Fri 4PM-6PM

Single Family Home

3 Beds 2 Baths 1,085 SqFt

1211 SCHULTZ AVE, Winter Park, FL 32789

Welcome to 1211 Schultz Avenue—a charming 3-bedroom, 2-bath bungalow offering an opportunity to enjoy the Winter Park li...

Listed by Onell Lee KELLER WILLIAMS WINTER PARK

Stellar MLS
1951 WINTER PARK RD, Winter Park, FL 32789
1/73 73

$2,089,000

Open Sun 1PM-3PM

Single Family Home

4 Beds 4 Baths 3,479 SqFt

1951 WINTER PARK RD, Winter Park, FL 32789

Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concep...

Listed by Holly Wilton KELLER WILLIAMS WINTER PARK

Stellar MLS
533 COUNTRY CLUB DR, Winter Park, FL 32789
1/31 31

$1,599,000

Open Sat 12PM-3PM

Single Family Home

4 Beds 4 Baths 2,942 SqFt

533 COUNTRY CLUB DR, Winter Park, FL 32789

Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless...

Listed by Jill Healey KELLER WILLIAMS WINTER PARK

Stellar MLS
1517 HARMON AVE, Winter Park, FL 32789
1/48 48

$1,095,000

Open Sat 10AM-3PM

Single Family Home

4 Beds 4 Baths 2,135 SqFt

1517 HARMON AVE, Winter Park, FL 32789

Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to botto...

Listed by Steven Koleno BEYCOME OF FLORIDA LLC

Stellar MLS
2572 FIFESHIRE DR, Winter Park, FL 32792
3D

$925,000

Open 10/10 12PM-2PM

Single Family Home

4 Beds 3 Baths 2,578 SqFt

2572 FIFESHIRE DR, Winter Park, FL 32792

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner ...

Listed by MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

Stellar MLS
2215 WOODCREST DR, Winter Park, FL 32792
3D

$675,000

Open Sun 2PM-4PM

Single Family Home

4 Beds 2 Baths 1,688 SqFt

2215 WOODCREST DR, Winter Park, FL 32792

Nestled on a tranquil, tree-lined street in the vibrant heart of Winter Park, this reimagined 1960s mid-century modern p...

Listed by Shari Klafter KELLER WILLIAMS WINTER PARK

Stellar MLS
1271 PALMER AVE, Winter Park, FL 32789
1/61 61

$2,195,000

Open Sun 12PM-2PM

Single Family Home

4 Beds 5 Baths 2,850 SqFt

1271 PALMER AVE, Winter Park, FL 32789

Set on a generous corner lot, this stunning single-story pool home in Winter Park has been beautifully remodeled and off...

Listed by JR Keelin KELLY PRICE & COMPANY LLC

Stellar MLS
618 BLAIRSHIRE CIR, Winter Park, FL 32792
1/64 64

$895,000

Open Sun 11AM-2PM

Single Family Home

4 Beds 3 Baths 1,876 SqFt

618 BLAIRSHIRE CIR, Winter Park, FL 32792

Virtually Staged. Fully renovated from top to bottom, this 4-bedroom, 3-bathroom pool home sits on a 9,915-square-foot l...

Listed by Ken Pozek REAL BROKER, LLC

Stellar MLS
2301 CONIFER AVE, Winter Park, FL 32792
1/28 28

$440,000

Open Sat 12PM-2PM

Single Family Home

4 Beds 2 Baths 2,189 SqFt

2301 CONIFER AVE, Winter Park, FL 32792

VIRTUALLY STAGED! EXCEPTIONAL POOL HOME IN EASTBROOK! Welcome to Conifer Avenue, where pride of ownership, and an unbeat...

Listed by Gregory Buckley LOKATION

Stellar MLS
2410 SHERBROOKE RD, Winter Park, FL 32792
1/73 73

$789,000

Open Sat 1PM-4PM

Single Family Home

4 Beds 3 Baths 2,141 SqFt

2410 SHERBROOKE RD, Winter Park, FL 32792

Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 ...

Listed by Li Ju Huang AMERICA REAL ESTATE COMPANY LL

Stellar MLS
2302 BARBADOS DR, Winter Park, FL 32792
1/35 35

$295,000

Open Sat 1PM-4PM

Townhouse

2 Beds 2 Baths 1,544 SqFt

2302 BARBADOS DR, Winter Park, FL 32792

Welcome to Windward Square, a desirable Winter Park community conveniently located near shopping, dining, entertainment ...

Listed by George Freelove KELLER WILLIAMS REALTY AT THE PARKS

Stellar MLS
274 N RANGER BLVD, Winter Park, FL 32792
1/38 38

$659,900

Open Sat 12AM-3PM

Single Family Home

3 Beds 2 Baths 1,420 SqFt

274 N RANGER BLVD, Winter Park, FL 32792

Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels li...

Listed by Shannon Lee EXPLORE FLORIDA REALTY SERVICES LLC

Stellar MLS
274 N RANGER BLVD, Winter Park, FL 32792
1/30 30

$3,790

Open Sat 11AM-3PM

Single Family Home

3 Beds 2 Baths 1,420 SqFt

274 N RANGER BLVD, Winter Park, FL 32792

Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! Brand new flooring creates a seaml...

Listed by Shannon Lee EXPLORE FLORIDA REALTY SERVICES LLC

Stellar MLS
1850 BRYAN AVE, Winter Park, FL 32789
1/31 31

$725,000

Open Sun 2PM-4PM

Single Family Home

3 Beds 2 Baths 1,563 SqFt

1850 BRYAN AVE, Winter Park, FL 32789

Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in...

Listed by Jennifer King CORCORAN PREMIER REALTY

Stellar MLS
1259 INDIANA AVE, Winter Park, FL 32789
1/67 67

$575,000

Open Sat 1PM-4PM

Townhouse

2 Beds 3 Baths 1,648 SqFt

1259 INDIANA AVE, Winter Park, FL 32789

Virtually Staged. WINTER PARK, WITHIN REACH. A rare opportunity to step into one of Central Florida's most coveted lifes...

Listed by Karan Wienker COLDWELL BANKER REALTY

Stellar MLS
900 CARVER ST, Winter Park, FL 32789
3D

$664,000

Open Sun 12PM-4PM

Single Family Home

3 Beds 3 Baths 1,794 SqFt

900 CARVER ST, Winter Park, FL 32789

Completely Remodeled 2026 | Single-Story | Prime Location | Dual Suites | The redesigned kitchen features 42" shaker cab...

Listed by Farhad Haniff EXP REALTY LLC

Stellar MLS
1526 MILLER AVE, Winter Park, FL 32789
1/27 27

$1,574,900

Open Fri 2PM-5PM

Single Family Home

5 Beds 5 Baths 3,252 SqFt

1526 MILLER AVE, Winter Park, FL 32789

New Construction! New photos coming soon! First photo is a rendering of the new home and the following photos are interi...

Listed by Kim Griffin RE/MAX EXCLUSIVE COLLECTION

Stellar MLS
7525 LODGE POLE TRL, Winter Park, FL 32792
1/38 38

$575,000

Open Sun 11AM-2PM

Single Family Home

4 Beds 2 Baths 1,936 SqFt

7525 LODGE POLE TRL, Winter Park, FL 32792

Welcome to this fully renovated four-bedroom, two-bathroom pool home offering close to 2,000 square feet of beautifully ...

Listed by Amy Turner KELLER WILLIAMS WINTER PARK

Stellar MLS
1927 S LAKEMONT AVE, Winter Park, FL 32792
3D

$915,000

Open Sat 12PM-3PM

Townhouse

3 Beds 4 Baths 2,093 SqFt

1927 S LAKEMONT AVE, Winter Park, FL 32792

Welcome to Lake Spier Crossing with NO CDD and low HOA fees, an exclusive boutique lakefront community built by Winter P...

Listed by Abby Green IAD REAL ESTATE

Stellar MLS
2703 TIERRA CIR, Winter Park, FL 32792
3D

$464,000

Open Thu 4PM-6PM

Single Family Home

3 Beds 2 Baths 1,737 SqFt

2703 TIERRA CIR, Winter Park, FL 32792

Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinki...

Listed by Tony Ubaldini EXP REALTY LLC

Stellar MLS
1418 LONE FEATHER TRL, Winter Park, FL 32792
1/46 46

$699,500

Open Sat 12PM-2PM

Single Family Home

4 Beds 3 Baths 2,197 SqFt

1418 LONE FEATHER TRL, Winter Park, FL 32792

Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,0...

Listed by Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

Stellar MLS
3006 NORTHWOOD BLVD, Winter Park, FL 32789
1/46 46

$925,000

Open Sat 1PM-3PM

Single Family Home

4 Beds 3 Baths 2,075 SqFt

3006 NORTHWOOD BLVD, Winter Park, FL 32789

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath...

Listed by Daren Ellington ORLANDO HOMES GROUP LLC

Stellar MLS
2015 SUMMERFIELD RD, Winter Park, FL 32792
1/31 31

$1,262,500

Open Sat 12PM-3PM

Single Family Home

4 Beds 4 Baths 3,024 SqFt

2015 SUMMERFIELD RD, Winter Park, FL 32792

Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together s...

Listed by Courtney Lindsay UNITED REAL ESTATE PREFERRED

Stellar MLS
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LPT Realty | Dreamtown Homes Team

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Chad Gibson, LLC
Chad Gibson
License ID: SL3471542
+1(407) 304-7461
chad@dthomesteam.com
924 N Magnolia Ave Suite 202 Unit #5373 Orlando, FL 32803

      Orlando Neighborhoods
      1. Audubon Park
      2. West Lakes District
      3. Parramore
      4. City District (Downtown)
      5. College Park
      6. Curry Ford West
      7. Gateway District
      8. Ivanhoe Village
      9. Mills 50
      10. SODO
      11. The Milk District
      12. Thornton Park
      13. Baldwin Park
      14. The Packing District
      Cities
      1. Altamonte Springs
      2. Celebration
      3. Davenport
      4. Doctor Phillips
      5. Horizon West
      6. Hunter's Creek
      7. Kissimmee
      8. Lake Nona
      9. Maitland
      10. Orlando
      11. Sanford
      12. Winter Garden
      13. Winter Park
      Buy/Sell
      1. Search Listings
      2. Featured Listings
      3. Sell My Home
      4. Home Valuation
      News
      1. Living In Orlando
      2. Market Snapshot
      Contact Us
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.

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

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

LPT Realty | Dreamtown Homes Team

Get My App

Chad Gibson, LLC
Chad Gibson
License ID: SL3471542
+1(407) 304-7461
chad@dthomesteam.com
924 N Magnolia Ave Suite 202 Unit #5373 Orlando, FL 32803

      Orlando Neighborhoods
      1. Audubon Park
      2. West Lakes District
      3. Parramore
      4. City District (Downtown)
      5. College Park
      6. Curry Ford West
      7. Gateway District
      8. Ivanhoe Village
      9. Mills 50
      10. SODO
      11. The Milk District
      12. Thornton Park
      13. Baldwin Park
      14. The Packing District
      Cities
      1. Altamonte Springs
      2. Celebration
      3. Davenport
      4. Doctor Phillips
      5. Horizon West
      6. Hunter's Creek
      7. Kissimmee
      8. Lake Nona
      9. Maitland
      10. Orlando
      11. Sanford
      12. Winter Garden
      13. Winter Park
      Buy/Sell
      1. Search Listings
      2. Featured Listings
      3. Sell My Home
      4. Home Valuation
      News
      1. Living In Orlando
      2. Market Snapshot
      Contact Us
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.

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

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