Winterpark Homes under $250,000

Welcome to Winterpark, a hidden gem nestled in the heart of Naples, Florida! This charming subdivision offers an inviting blend of community spirit and serene living, making it an ideal choice for families, retirees, and everyone in between. With its lush landscapes and well-maintained surroundings, Winterpark is a place where neighbors become friends and memories are made.

One of the standout features of Winterpark is its affordability, particularly for those seeking homes under $250,000. This unique aspect makes it a perfect opportunity for first-time homebuyers or those looking to downsize without compromising on quality of life. The homes in this price range are thoughtfully designed, offering a variety of layouts and modern amenities that cater to diverse lifestyles.

Winterpark residents enjoy access to a range of local conveniences, including shopping, dining, and recreational options. The nearby beaches of Naples are just a short drive away, providing endless opportunities for sun-soaked days and breathtaking sunsets. Additionally, the community is known for its friendly atmosphere and active neighborhood events, fostering a sense of belonging among residents.

Whether you're searching for a quaint starter home or a peaceful retreat, Winterpark offers an array of options that won't break the bank. Experience the charm of Naples living in this delightful subdivision, where affordability meets community spirit, and your dream home awaits! Explore Winterpark today and discover the perfect place to call home in sunny Florida.

Newest Winterpark Homes under $250,000

4079 Northlight DR Unit 2, Naples — Winterpark $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
226034559 MLS
Winterpark Bldg.

4096 Northlight DR Unit 1709, Naples image

4096 Northlight DR Unit 1709, Naples — Winterpark $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
Winterpark Bldg.

4038 Northlight DR Unit 1506, Naples image

4038 Northlight DR Unit 1506, Naples — Winterpark $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
226030364 MLS
Winterpark Bldg.

4230 Jack Frost CT Unit 4402, Naples image

4230 Jack Frost CT Unit 4402, Naples — Winterpark $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
Winterpark Bldg.

4001 Ice Castle WAY Unit 1, Naples image

4001 Ice Castle WAY Unit 1, Naples — Winterpark $245,000

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
Winterpark Bldg.

3816 Snowflake LN Unit 1303, Naples image

3816 Snowflake LN Unit 1303, Naples — Winterpark $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
226024603 MLS
Winterpark Bldg.

3532 Antarctic CIR Unit 2216, Naples image

3532 Antarctic CIR Unit 2216, Naples — Winterpark $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
226020005 MLS
Winterpark Bldg.

3420 Frosty WAY Unit 4910, Naples — Winterpark $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
226017233 MLS
Winterpark Bldg.

4050 Ice Castle WAY Unit 2812, Naples image

4050 Ice Castle WAY Unit 2812, Naples — Winterpark $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
226016168 MLS
Winterpark Bldg.

4031 Ice Castle WAY Unit 3306, Naples image

4031 Ice Castle WAY Unit 3306, Naples — Winterpark $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
226011974 MLS
Winterpark Bldg.

4100 Looking Glass LN Unit 3002, Naples image

4100 Looking Glass LN Unit 3002, Naples — Winterpark $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
226009042 MLS
Winterpark Bldg.

4200 Looking Glass LN Unit 4204, Naples image

4200 Looking Glass LN Unit 4204, Naples — Winterpark $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...