Winterpark Condos for Sale

Welcome to Winterpark, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This vibrant neighborhood is renowned for its serene atmosphere, lush landscapes, and a community spirit that makes it feel like home. With its prime location, Winterpark offers residents easy access to the best that Naples has to offer, from stunning beaches to upscale shopping and dining experiences.

Winterpark is characterized by its charming tree-lined streets, beautifully manicured lawns, and a variety of recreational amenities. Residents enjoy a wealth of outdoor activities, including scenic walking paths, sparkling lakes, and nearby parks perfect for picnics or leisurely strolls. The community is also known for its engaging social events that foster connections among neighbors, making it an ideal spot for families, retirees, and everyone in between.

For those considering a move to Winterpark, the selection of condos for sale is impressive. These residences offer a perfect blend of comfort, style, and convenience, catering to diverse lifestyles. Many condos feature modern amenities, spacious layouts, and breathtaking views, allowing you to enjoy the beauty of Naples right from your own home. Whether you're looking for a cozy retreat or a luxurious space for entertaining, Winterpark’s condos provide a range of options to suit your needs.

Embrace the Winterpark lifestyle, where community meets convenience in one of Florida's most desirable locations. Explore the available condos for sale today, and discover your perfect piece of paradise in Naples!

Newest Winterpark Condos for Sale

$250,000

2 Beds ⋅ 2 Baths ⋅ 226028571 MLS ⋅ Winterpark BLDG.

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 the quiet and well-established Winterpark community, this spacious 2 BR / 2 BA condo offers 1,246 s/f and a blank canvas ready for its next owner’s vision. Step inside to an open living area enhanced by dramatic vaulted ceilings that make the home feel even larger, while the screened front porch offers a comfortable place to enjoy the Florida air. With a spacious layout and a true blank-canvas feel, the condo offers the freedom to personalize, reimagine, and create a space that reflects your own style. Winterpark is known for its outstanding amenities, highlighted by an expansive community pool surrounded by a tropical setting, along with pickleball, tennis, bocce, and clubhouse facilities. Whether you are looking for a full-time residence, seasonal retreat, or investment property, the community offers a peaceful neighborhood atmosphere while keeping you close to everything that makes Naples so desirable. Downtown Naples, 5th Avenue South, Tin City, Gulf beaches, shopping, dining, and everyday conveniences are all just a short drive away. Rental flexibility allowing up to 3 leases per year with a 30-day minimum adds even more appeal for buyers looking for income potential or seasonal use. With generous living space, exceptional community amenities, and a location that keeps the best of Naples within easy reach, this condo offers an inviting opportunity to create a home that truly feels like your own. Come see firsthand why this could be the Naples opportunity you’ve been waiting for.

4230 Jack Frost CT Unit 4402, Naples

$255,000

2 Beds ⋅ 2 Baths ⋅ 226028684 MLS ⋅ Winterpark BLDG.

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 amazing updates all throughout, this condo shows like new. A beautifully updated and spacious kitchen has brand new stainless steel appliance that have never been used! Large beautiful tile all throughout with clean carpeting in the bedrooms. Bath bathrooms have been updated as well and are clean and bright. The front lanai is screened in and is a perfect place to BBQ or enjoy your morning coffee. Feel free to build your own outdoor screened lanai with the communities new approval! Winterpark has great amenities and is close to downtown Naples and the surrounding area.

3574 Antarctic CIR Unit 2107, Naples

$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

$262,000

2 Beds ⋅ 2 Baths ⋅ 226027202 MLS ⋅ Winterpark BLDG.

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 in the heart of Naples. This cozy high-ceilings 2nd-floor END-UNIT condo offers 2 bedrooms, 2 bathrooms, and a desirable concept floor plan with a spacious living area, designed for comfortable Florida living. The screened front balcony provides the perfect setting for morning coffee or an evening glass of wine while enjoying the peaceful Florida sunsets. Second-floor residences are the only homes in Winterpark with soaring cathedral ceilings, creating a bright and open atmosphere throughout. Kitchen side wall removed to enhance the kitchen and living area. The owner's suite features an added barn door for more privacy. With no carpet throughout, partially furnished interiors (inventory list available), a large laundry room with an oversized private storage closet, additional attic storage, and an exterior storage unit, this home offers exceptional convenience. Major updates provide peace of mind, including approximately 2-year-old appliances, a 2022 roof, CPVC plumbing, and a water heater replaced at the end of 2025. And a one-year home warranty is included with the purchase! Ideally located just a short walk from the community amenities. Winterpark residents enjoy an active resort-style lifestyle featuring a large swimming pool, tennis and pickleball courts, bocce courts, and a welcoming clubhouse. This residence also offers quick access to Downtown Naples, world-famous white-sand Gulf beaches, premier shopping, dining, and entertainment. Beyond the community, Naples offers an exceptional blend of recreation and culture, including Gulfshore Opera, Artis—Naples, The Baker Museum, Gulfshore Playhouse, The Naples Players, Naples Botanical Garden, Naples Zoo, and countless parks and nature preserves. Popular destinations such as Fifth Avenue South, Third Street South, Venetian Village, Waterside Shops, and Mercato offer outstanding shopping, dining, and entertainment. Whether as a full-time residence, seasonal retreat, or investment opportunity, this property represents outstanding value in one of Naples' most desirable locations.

3420 Frosty WAY Unit 4902, 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

$249,000

2 Beds ⋅ 2 Baths ⋅ 226017233 MLS ⋅ Winterpark BLDG.

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 your dream Naples retreat awaits. Positioned in a prime Naples location, this 2-bedroom, 2-bath condominium offers a light-filled layout with an expansive living and dining area, ready to be reimagined with your personal style and design vision. The screened balcony provides a peaceful outdoor space overlooking lush tropical landscaping—perfect for morning coffee or unwinding after a day at the beach. Inside, you’ll find a spacious primary suite, in-unit laundry, and a functional floor plan that serves as the perfect canvas for updates, renovations, or a full custom transformation. What truly sets this property apart is its placement within Winterpark—one of Naples’ most desirable, amenity-rich communities known for its vibrant lifestyle and classic Florida charm. Residents enjoy access to one of the largest resort-style pools in Naples, beautifully maintained grounds, newly updated pickleball and tennis courts, and an active social atmosphere that makes it easy to feel at home. Located just minutes from 5th Avenue South and Olde Naples, as well as world-renowned Gulf beaches, this property offers unmatched convenience to fine dining, boutique shopping, art galleries, and coastal living at its finest. Whether you’re seeking a seasonal escape, investment opportunity, or a full-time residence to customize and make your own, this is your chance to unlock the full potential of Naples living in a community that truly embodies the Florida lifestyle.

3420 Frosty WAY Unit 4910, 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

$284,900

2 Beds ⋅ 2 Baths ⋅ 226012607 MLS ⋅ Winterpark BLDG.

Welcome to Winterpark, one of Naples most sought-after communities just minutes from downtown and the pristine Gulf beaches. This beautifully updated 2-bedroom, 2-bath 1st floor condo offers a perfect blend of modern style and effortless Florida living. Step inside to an open, light-filled layout designed for both comfort and entertaining. Darkwood accents & cabinetry in the kitchen and breakfast bar, custom tile work and exquisite finishes throughout. Enjoy your morning coffee or unwind in the evening on the spacious lanai, a perfect private retreat with a relaxing, tropical feel. Winterpark is known for its resort-style amenities, including one of the largest pools in Naples, newly updated pickleball and tennis courts, and a vibrant, active social atmosphere. Surrounded by lush green spaces and charming scenery, the community captures the essence of classic Florida living. Ideally located just minutes from 5th Avenue South, Olde Naples, shopping, dining, and the beach, this property is perfect as a full-time residence, seasonal getaway, or investment opportunity. Come experience it for yourself—this one won’t last.

4150 Looking Glass LN Unit 3903, Naples

$250,000

2 Beds ⋅ 2 Baths ⋅ 226011974 MLS ⋅ Winterpark BLDG.

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 including, Tennis Courts, Pickleball, Bocce Ball, Shuffleboard, and a Resort style pool. Walking distance to shopping(Home Depot ,Publix, Walgreen's) and restaurants. Pets are Allowed.

4031 Ice Castle WAY Unit 3306, Naples

$209,500

2 Beds ⋅ 2 Baths ⋅ 2026009632 MLS ⋅ Winterpark BLDG.

Best Value in Winterpark – First Floor • Turnkey • Impact Windows • New A/C • Conventional Financing On of the Lowest-priced first-floor condo in Winterpark. This turnkey-furnished home offers an incredible opportunity to own in one of Naples’ most desirable communities while leaving room in your budget to update and personalize it over time. The home offers a comfortable, functional layout with one nicely updated bathroom while providing an opportunity to personalize the remaining spaces to your own taste and style. Major improvements have already been completed, including updated plumbing, impact windows and an impact sliding glass door, a new A/C (2024), and a new water heater (2023), allowing you to focus on making it your own. For added peace of mind, the condominium association carries a master flood insurance policy. The property also qualifies for conventional financing, offering greater flexibility for buyers. Winterpark is known for its lush, walkable setting, spectacular resort-style pool, tennis courts, and welcoming atmosphere. Ideally located just minutes from downtown Naples, 5th Avenue South, shopping, dining, and the beautiful Gulf beaches, you’ll enjoy everything Southwest Florida has to offer. Quarterly HOA dues are $1,920 and include outstanding community amenities and exterior maintenance. Pets and rentals are permitted, adding to the property’s versatility. Motivated sellers have priced this home to sell. If you’ve been searching for an affordable opportunity to own in one of Naples’ most popular communities, this is one you won’t want to miss.

4070 Looking Glass LN Unit 3101, 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.