Winterpark Homes under $250,000

Welcome to Winterpark, a delightful subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community offers an inviting atmosphere, perfect for those seeking a peaceful yet vibrant lifestyle. With its lush landscapes and well-maintained properties, Winterpark is an ideal haven for families, retirees, and anyone looking to enjoy the best of Southwest Florida living.

One of the standout features of Winterpark is its affordability. Here, you can find homes priced under $250,000, making it an attractive option for first-time homebuyers, investors, or anyone looking to downsize without sacrificing quality of life. These homes offer a range of options, from cozy single-family residences to comfortable townhomes, each designed to provide a warm and welcoming environment.

Residents of Winterpark enjoy easy access to a variety of amenities, including shopping centers, dining options, and recreational facilities. The nearby beaches are just a short drive away, offering sun-soaked days and breathtaking sunsets. Additionally, the community is well-connected to major roadways, ensuring that you are never far from the vibrant culture and entertainment that Naples has to offer.

Whether you're looking to start a new chapter in your life or simply seeking a serene retreat, Winterpark promises a blend of affordability and charm that is hard to resist. Come explore this hidden gem and discover the perfect place to call home in sunny Naples, FL!

Newest Winterpark Homes under $250,000

4079 Northlight Drive Unit 2, Naples image

4079 Northlight Drive Unit 2, Naples $247,000

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
Winterpark SubDv.

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
Winterpark SubDv.

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
Winterpark SubDv.

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
Winterpark SubDv.

4001 Ice Castle Way Unit 1, Naples image

4001 Ice Castle Way Unit 1, Naples $245,000

Escape to this meticulously maintained two-bedroom condo featuring a brand-new air conditioning system, hurricane windows and doors, plus plantation sliders and shutters....

2 Beds
2 Baths
Winterpark SubDv.

3816 Snowflake Lane Unit 1303, Naples image

3816 Snowflake Lane Unit 1303, Naples $224,000 ▼

Welcome to Winter Park! Ready for its next owner, this charming 2-bedroom, 2-bathroom centrally located condo is a fantastic find. It features hurricane-resistant windows...

2 Beds
2 Baths
Winterpark SubDv.

3532 Antarctic Circle Unit 2216, Naples image

3532 Antarctic Circle Unit 2216, Naples $248,000

Discover a pristine Naples paradise with this meticulously maintained 2 bedroom, 2 bathroom condominium at Winter Park that shines with amazing amenities and a luxurious ...

2 Beds
2 Baths
Winterpark SubDv.

3420 Frosty Way Unit 4910, Naples $249,000

Welcome to an exceptional opportunity to own an upstairs residence in the highly sought-after Winterpark community—where value meets vision and the potential to create yo...

2 Beds
2 Baths
Winterpark SubDv.

4050 Ice Castle Way Unit 2812, Naples image

4050 Ice Castle Way Unit 2812, Naples $239,000 ▼

One or more photo(s) has been virtually staged, AI generated or rendered. One or more photo(s) has been virtually staged, AI generated or rendered. Beautiful lake-view c...

2 Beds
2 Baths
Winterpark SubDv.

4031 Ice Castle Way Unit 3306, Naples image

4031 Ice Castle Way Unit 3306, Naples $250,000

Nicely appointed 2ND FLOOR UNIT with screened-in deck. Ready to move in. Newer refrigerator and Range in kitchen. A/C is 3 years old. Extensive amenities in the complex i...

2 Beds
2 Baths
Winterpark SubDv.

4100 Looking Glass Lane Unit 3002, Naples image

4100 Looking Glass Lane Unit 3002, Naples $240,000 ▼

Seller Says Sell! Price reduction for this amazing condo in highly sought after Winterpark. Discover the perfect blend of comfort, style, and location in this spacious s...

2 Beds
2 Baths
Winterpark SubDv.

4200 Looking Glass Lane Unit 4204, Naples image

4200 Looking Glass Lane Unit 4204, Naples $209,000 ▼

Welcome home to this beautifully maintained Winter Park condo offering over 1,200 square feet of comfortable living space with peaceful green space views. This spacious r...