Winterpark Homes with Sidewalk Amenities

Welcome to Winterpark, a hidden gem nestled in the heart of Naples, Florida. This charming neighborhood is part of Collier County and is renowned for its serene ambiance and family-friendly atmosphere. With tree-lined streets and beautifully manicured lawns, Winterpark offers a picturesque setting that feels like home the moment you arrive.

One of the standout features of Winterpark is its commitment to community and connectivity. With sidewalks that wind through the neighborhood, residents enjoy leisurely strolls, morning jogs, or evening bike rides while soaking in the Florida sunshine. These pathways not only promote an active lifestyle but also foster a sense of camaraderie among neighbors, making it easy to meet friends or enjoy a casual chat with fellow residents.

The homes in Winterpark are thoughtfully designed, blending modern comforts with classic Florida architecture. Whether you’re looking for a cozy single-family home or a spacious residence for your growing family, you’ll find a variety of options that cater to diverse tastes and preferences. Many properties feature lush landscaping, private backyards, and inviting patios, perfect for outdoor entertaining or quiet evenings under the stars.

Residents of Winterpark also benefit from its prime location, with easy access to Naples’ stunning beaches, vibrant shopping districts, and an array of dining options that showcase the best of Florida cuisine. Whether you’re a nature lover, a foodie, or someone who enjoys the finer things in life, Winterpark is the perfect place to call home. Come explore this delightful neighborhood and discover the lifestyle that awaits you!

Newest Winterpark Homes with Sidewalk Amenities

$245,000

2 Beds ⋅ 2 Baths ⋅ 226026798 MLS ⋅ Winterpark BLDG.

Escape to this meticulously maintained two-bedroom condo featuring a brand-new air conditioning system, hurricane windows and doors, plus plantation sliders and shutters. The open, spacious floor plan offers large bedrooms and abundant storage, with California Closets beautifully finishing out the master en suite. Outdoor living is enhanced by a screened front patio and a rear patio, perfect for year-round enjoyment. As an end unit, it’s flooded with natural light, from sunrise to sunset. Enjoy resort-style amenities including a pool, clubhouse, tennis, and pickleball courts—all with low association fees and a never-flooded property. You’re steps from the pool, with convenient parking right outside your door, and just minutes to the beach, downtown Naples, and local shopping.

4001 Ice Castle WAY Unit 1, Naples

$249,000

2 Beds ⋅ 2 Baths ⋅ 226024603 MLS ⋅ Winterpark BLDG.

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 and a delightful patio perfect for your morning coffee. Well-priced and full of potential, this home is waiting for your personal touches! The location is truly unbeatable—just 3 miles from the famous beaches of Naples and the vibrant shops and restaurants on Olde Naples' 5th Avenue. Plus, you can easily walk to Kings Lake Square, which offers a Publix, various shops, and multiple dining options.

3816 Snowflake LN Unit 1303, Naples

$248,000

2 Beds ⋅ 2 Baths ⋅ 226020005 MLS ⋅ Winterpark BLDG.

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 location. Enjoy a condo that benefits from splendid design choices, including vaulted ceilings, plentiful natural light, and split bedrooms. The primary suite is a relaxing retreat, featuring a walk-in closet and a stylish barn door that leads to the en-suite master bath with a sparkling shower. The unit comes turnkey; all you have to bring is your suitcase! This condo is fully equipped with much-desired impact windows and sliders to protect your paradise. Additional in-unit perks include a spacious laundry and utility room with a dedicated washer and dryer and room to spare, as well as a clever small storage area tucked under the stairs, perfect for storing bikes and beach chairs. Tile and carpet flooring throughout. Winter Park boasts an absolutely stacked lineup of amenities that includes one of the LARGEST resort-style community pools in Naples, a beautiful clubhouse with an expansive library, separate pickleball and tennis courts, bocce and shuffleboard courts, and bike and jog path; a sensational lineup of community activities for a fabulous community. What’s more - this particular condo is situated well in this robust community, enjoying close proximity to all of these amenities. Just minutes from world-renowned 5th Avenue, scintillating shopping, and beautiful beaches, this location is absolutely rich with convenience. No matter what your real estate goal is, this Winter Park wonderland offers the quintessential Southwest Florida lifestyle!

3532 Antarctic CIR Unit 2216, Naples

$239,000

2 Beds ⋅ 2 Baths ⋅ 226016168 MLS ⋅ Winterpark BLDG.

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 condo just minutes from everything Naples has to offer! Located only 8 minutes from the beach and close to 5th Ave South and downtown, this desirable second-floor unit offers privacy, natural light, and beautiful Lake views. Featuring 2 bedrooms and 2 bathrooms, this home boasts vaulted ceilings, an updated Tile and carpet flooring throughout, and a spacious primary suite with a walk-in closet. The living area is enhanced with impact windows, providing both peace of mind and energy efficiency. Whether you're looking for a full-time residence, seasonal getaway, or income-producing rental investment, this unit checks all the boxes. Allows up to 12 rentals per year with a 30-day minimum, offering excellent flexibility and strong income potential making it a fantastic opportunity for investors seeking Airbnb-style or seasonal rental income.

4050 Ice Castle WAY Unit 2812, Naples

$309,900

2 Beds ⋅ 2 Baths ⋅ 226015387 MLS ⋅ Winterpark BLDG.

Charming 2 Bed, 2 Bath in Desirable Winterpark – Prime Naples Location Nestled in the heart of sunny Naples, this beautifully updated 2-bedroom, 2-bathroom condo in Winter park offers the perfect blend of comfort, style, and convenience. The open-concept layout is ideal for entertaining, while the spacious screened-in lanai provides a peaceful space to relax and unwind. Located just a short drive to 5th Avenue, Naples Beach, Publix, and a variety of restaurants and shops, this highly sought-after community.

4030 Northlight DR, Naples

$240,000

2 Beds ⋅ 2 Baths ⋅ 226009042 MLS ⋅ Winterpark BLDG.

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 second-floor corner condo in beautiful Naples. Featuring vaulted ceilings and serene garden views, this light-filled residence offers privacy and tranquility within the lush, peaceful community of Winterpark. This updated 2-bedroom, 2-bath home showcases an open, airy layout with neutral tones that complement any décor. The remodeled kitchen features modern cabinetry, quartz countertops, stainless steel appliances, and a convenient breakfast bar that flows seamlessly into the expansive living and dining areas—ideal for entertaining or relaxing at home. Both bathrooms have also been tastefully renovated. Other updates include a newer A/C, a brand new water heater, and a roof that's only a year old for added peace of mind. Flood insurance is covered by the association. Another advantage is the in-unit laundry room with washer, dryer, and abundant storage. Enjoy Florida living year-round from the screened porch overlooking the garden, the large heated community pool, tennis courts and other playing courts, as well as walking and jogging paths. Other features include private assigned parking and plenty of additional guest parking for even more convenience. Extra private storage accompanies this property to store your bike or anything else you may need. The location is perfect, only a few minutes to Downtown Naples and its world renowned beaches, plus easy access to exceptional dining, shopping and entertainment options. Pet-friendly, rental-friendly and without age restrictions, this condo presents an excellent investment opportunity or seasonal retreat. While other units may be available in the community, this beautifully updated corner residence truly stands out—one you must see in person to fully appreciate.

4100 Looking Glass LN Unit 3002, Naples

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The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.