Winterpark Real Estate

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winterpark and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

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Newest Listings in Winterpark

4038 Northlight Drive Unit 1506, Naples image

4038 Northlight Drive Unit 1506, Naples $249,900

Lake views and a prime in-town Naples location define this move-in-ready 2-bedroom, 2-bath second-floor condo in Naples Winterpark IV. Enjoy water views over the communi...

2 Beds
2 Baths
226038074 MLS

4001 Ice Castle Way Unit 3605, Naples image

4001 Ice Castle Way Unit 3605, Naples $265,000

Fully renovated in March 2022 with brand new kitchen, floors, hurricane windows & doors, and new bathrooms. Quartz countertops, glass tile backsplashes, stainless steel a...

2 Beds
2 Baths
226036321 MLS

4079 Northlight Drive Unit 2, Naples image

4079 Northlight Drive Unit 2, Naples $220,000 ▼

Welcome to this spacious and beautifully updated second-floor end-unit condo in the desirable Winterpark community. Freshly painted throughout, this home features an upgr...

2 Beds
2 Baths
226034559 MLS

4096 Northlight Drive Unit 1709, Naples image

4096 Northlight Drive Unit 1709, Naples $239,000

For sale is this 2 bedroom 2 bath 1st floor end unit beautiful Winterpark Naples condo. A short drive or walk to Naples world famous white sandy sunny beaches. Northl...

2 Beds
2 Baths
2026040990 MLS

3400 Frosty Way Unit 5, Naples $299,000 ▼

Welcome to Winterpark—one of Naples’ most convenient, low-maintenance communities—just minutes from 5th Avenue, Bayfront, Tin City, and the Gulf. This first-floor 2 bedro...

2 Beds
2 Baths
226032860 MLS

4073 Northlight Drive Unit 1803, Naples image

4073 Northlight Drive Unit 1803, Naples $265,000

First-floor 2BR/2BA condo in the highly desirable Winter Park community and located in Winter Park IV. This light and spacious home features an inviting screened front po...

2 Beds
2 Baths
226033685 MLS

4100 Looking Glass Lane Unit 3008, Naples image

4100 Looking Glass Lane Unit 3008, Naples $255,000

Welcome to **4100 Looking Glass Ln #8**, a great opportunity to own in Naples! This inviting residence offers a comfortable and functional layout with plenty of natural l...

2 Beds
2 Baths
226031126 MLS

4027 Northlight Drive Unit 4, Winter Park image

4027 Northlight Drive Unit 4, Winter Park $259,900

Welcome to 4027 Northlight Drive #4 in the desirable Winterpark community, offered at $259,900! This light and breezy second-floor, 2-bedroom, 2-bath condo features an up...

2 Beds
2 Baths
226030748 MLS

4230 Jack Frost Court Unit 4402, Naples image

4230 Jack Frost Court Unit 4402, Naples $230,000 ▼

One or more photo(s) has been virtually staged, AI generated or rendered. Soaring vaulted ceilings. Exceptional amenities. Prime Naples location. Great value! Located in...

2 Beds
2 Baths
226028571 MLS

3574 Antarctic Circle Unit 2107, Naples image

3574 Antarctic Circle Unit 2107, Naples $255,000

Looking for that perfect seasonal sanctuary or cozy abode in the heart of Naples? Look no further! This first floor two bedroom, two bathroom is ready for move in. With a...

2 Beds
2 Baths
226028684 MLS

4001 Ice Castle Way Unit 1, Naples image

4001 Ice Castle Way Unit 1, Naples $235,000 ▼

Sun-drenched END UNIT with natural light from sunrise to sunset. Escape to this meticulously maintained 2-bedroom condo featuring a NEW air conditioning system, hurricane...

2 Beds
2 Baths
226026798 MLS

3420 Frosty Way Unit 4902, Naples $262,000

One or more photo(s) has been virtually staged, AI generated or rendered. Move-in ready, exceptionally well-maintained condo. Welcome to Winterpark, a tropical retreat i...

2 Beds
2 Baths
226027202 MLS