Winterpark Real Estate

Winterpark Real Estate

Welcome to Winterpark, a charming subdivision nestled in the heart of Naples, Florida, in the picturesque Collier County. This vibrant community offers a perfect blend of tranquility and convenience, making it an ideal choice for families, retirees, and anyone seeking a serene lifestyle in one of Florida's most sought-after locations.

Winterpark is known for its beautifully landscaped surroundings and well-maintained homes that reflect the quintessential Floridian architectural style. The neighborhood features a variety of single-family homes, each exuding charm and warmth, with many properties boasting lush gardens and private outdoor spaces perfect for enjoying the year-round sunshine.

Residents of Winterpark enjoy access to an array of amenities that enhance the community's appeal. Take a leisurely stroll through the scenic walking paths, or gather with friends at the community clubhouse, where social events and activities foster a strong sense of camaraderie among neighbors. The community pool offers a refreshing retreat on warm days, while playgrounds and recreational areas provide ample opportunities for outdoor fun.

Located just minutes from Naples' stunning beaches, premier shopping districts, and fine dining establishments, Winterpark residents can easily indulge in the best that the area has to offer. With top-rated schools and a welcoming atmosphere, this subdivision is perfect for families looking to lay down roots in a vibrant community.

Discover the charm of Winterpark, where your dream home awaits amid the beauty and warmth of Naples, Florida!

Newest Listings in Winterpark

4065 Northlight Dr Unit 1807, Naples
$250,000
2 Beds ⋅ 2 Baths ⋅ 226037301 MLS ⋅ Winterpark BLDG.
!!!You cannot get a better location and square footage for the money this close to town in any other community!!! PET-FRIENDLY -- spacious FIRST floor 2BR/2BA garden apartment is only a few minutes to downtown Naples and all the wonderful activities, shopping, restaurants, entertainment and of course, the world-renowned beaches! The updated residence is LIGHT & BRIGHT and features 1200+SF including a front screened-in lanai and a rear open patio. The primary suite has a private full bath plus a large walk-in closet. You are a short walk to the Winterpark neighborhood amenities including the HUGE heated, resort-style community pool which is the 3rd largest in the state of Florida! The pool deck is dotted with palm trees and an abundance of deck chairs! There are also bike and jogging trails, park-like landscaping, tennis and pickle ball courts, bocce and the fabulous clubhouse has a library and tons of activities! You can walk to Kings Lake Square for grocery shopping and some of the areas best and well-priced restaurants! This is AN IDEAL year-round or seasonal residence! *Per the community's financials, the HOA provides flood insurance and is included in the quarterly fee. This policy satisfies the required coverage for a mortgage. *

4065 Northlight Dr Unit 1807, Naples
4038 Northlight Dr Unit 1506, Naples
$249,900
2 Beds ⋅ 2 Baths ⋅ 226038074 MLS ⋅ Winterpark BLDG.
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 community lake from a screened porch made for Southwest Florida mornings and evenings. The bright split-bedroom plan offers comfortable living and dining space, a full appliance package, and ceiling fans throughout. Ownership includes membership in the Winterpark Tennis and Pool Club, putting the community pool and tennis courts at your doorstep, plus a bike-path easement for easy rides and walks. The quarterly fee covers cable, insurance, grounds and landscaping, exterior and building maintenance, a pest and termite program, roof reserves, management, and trash for true lock-and-leave living. You are about two miles from Celebration Park and the Bayshore Arts District, under three miles from downtown Naples, 5th Avenue South, and Tin City, and roughly three and a half miles from the Naples Botanical Garden, with a Publix under two miles away. World-class beaches, dining, and shopping are all a short drive. A market-timely plus: this is a two-story building, so it is not subject to Florida's milestone inspection or structural integrity reserve study requirements, which apply to buildings three stories and up. Ideal as a seasonal retreat, investment, or easy year-round home.

4038 Northlight Dr Unit 1506, Naples
4001 Ice Castle Way Unit 3605, Naples
$265,000
2 Beds ⋅ 2 Baths ⋅ 226036321 MLS ⋅ Winterpark BLDG.
Fully renovated in March 2022 with brand new kitchen, floors, hurricane windows & doors, and new bathrooms. Quartz countertops, glass tile backsplashes, stainless steel appliances, new AC and water heater, luxury vinyl flooring, new hurricane windows and doors. Beautifully furnished/decorated with new furniture and art, this well-appointed home is being sold turnkey. The condo also features a large convenient outdoor storage for bicycles or beach toys which is perfect for enjoying Florida's sunny lifestyle. The community is complete with a Clubhouse, Resort-Style Pool, tennis, pickle ball and bocce courts and a lovely walking trail. Conveniently located in the heart of Naples with a short distance to the beach, downtown, 5th Avenue South, Publix and Interstate 75. First floor unit with assigned parking and low association fees.

4001 Ice Castle Way Unit 3605, Naples
4079 Northlight Dr Unit 2, Naples
$220,000
2 Beds ⋅ 2 Baths ⋅ 226034559 MLS ⋅ Winterpark BLDG.
Welcome to this spacious and beautifully updated second-floor end-unit condo in the desirable Winterpark community. Freshly painted throughout, this home features an upgraded kitchen and bathrooms, high ceilings, and exceptional storage, including an attic, a spacious laundry room, and an outdoor storage closet. Smart-home features add modern convenience, including Lutron Caséta lighting controls, a smart thermostat, and smart appliances, many of which can be conveniently controlled from your phone. Winterpark offers an outstanding resort-style lifestyle with a large community pool, multiple tennis courts, and a clubhouse for social gatherings, events, and neighborhood activities. The community is well maintained, with reasonable HOA fees. The location is hard to beat, with the beach just a 10-minute drive away and grocery stores and hardware stores within walking distance. You'll also be close to Downtown Naples, parks, fitness centers, boat ramps, NCH Baker Hospital, restaurants, shopping, and other everyday conveniences. A wonderful opportunity to enjoy the Naples lifestyle in a move-in-ready home with desirable updates, smart features, abundant storage, and the added privacy of an end-unit location.

4079 Northlight Dr Unit 2, Naples
4096 Northlight Dr Unit 1709, Naples
$239,000
2 Beds ⋅ 2 Baths ⋅ 2026040990 MLS ⋅ Winterpark BLDG.
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. Northlight dr is a great location and you just can not beat this wonderful community.

4096 Northlight Dr Unit 1709, Naples
3400 Frosty Way Unit 5, Naples
$299,000
2 Beds ⋅ 2 Baths ⋅ 226032860 MLS ⋅ Winterpark BLDG.
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 bedroom, 2 bath residence has undergone an extensive and impeccable REMODEL, delivering a bright, open split-bedroom plan designed for easy living and privacy. Every finish feels intentional and move-in ready. Tile flooring flows through the living spaces, anchored by a granite kitchen that opens to the dining and living areas. The primary suite is generously sized with a walk-in closet; the second bedroom and full bath are ideal for guests or seasonal use. A newly screened lanai extends the living space outdoors for morning coffee or sunset dinners. Thoughtful updates include impact-rated windows and doors, a newer roof, and a newer water heater. In-unit laundry and assigned parking add everyday ease. Residents enjoy one of the larger community pools in Naples, plus tennis, bocce, a clubhouse, and extra storage, all set among mature landscaping. Whether you are looking for a full-time home, a seasonal retreat, or a well-located rental, this fully remodeled, TURNKEY-furnished, move-in-ready condo delivers the Naples lifestyle without the upkeep.

3400 Frosty Way Unit 5, Naples
4073 Northlight Dr Unit 1803, Naples
$265,000
2 Beds ⋅ 2 Baths ⋅ 226033685 MLS ⋅ Winterpark BLDG.
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 porch, a bright open living and dining area with modern flooring, and a stylish kitchen with white cabinetry, granite counters, stainless steel appliances, and a mosaic tile backsplash. The large laundry room offers exceptional storage, complemented by an additional exterior storage closet. Winter Park residents enjoy one of Naples’ largest resort-style pools, tennis, pickleball, bocce, a clubhouse, and beautifully landscaped walking areas. HOA fees include water, sewer, basic cable, and WiFi—leaving only electric as your utility bill. All just minutes from 5th Avenue South, Downtown Naples, and Naples’ world-famous beaches. A prime location with outstanding amenities and move-in-ready appeal.

4073 Northlight Dr Unit 1803, Naples
4100 Looking Glass Ln Unit 3008, Naples
$255,000
2 Beds ⋅ 2 Baths ⋅ 226031126 MLS ⋅ Winterpark BLDG.
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 light and a relaxed Florida feel. Conveniently located near shopping, dining, entertainment, golf, downtown Naples, and the beautiful Gulf beaches. Whether you're looking for a future residence or an investment opportunity, this property offers excellent potential in a desirable Naples location. **Currently tenant occupied, making it an attractive option for investors. Please allow appropriate notice for showings.**

4100 Looking Glass Ln Unit 3008, Naples
4027 Northlight Dr Unit 4, Winter Park
$259,900
2 Beds ⋅ 2 Baths ⋅ 226030748 MLS ⋅ Winterpark BLDG.
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 updated kitchen and bathrooms and a comfortable, inviting floor plan perfect for enjoying the Naples lifestyle.Step outside to the tiled and screened lanai, the perfect spot to enjoy your morning coffee, relax with a good book, or take advantage of Naples' beautiful year-round weather. Winterpark is a popular Naples community known for its resort-style atmosphere, beautifully maintained grounds and exceptional recreational amenities. Residents enjoy one of the area's impressive community pools, along with tennis and pickleball courts and plenty of opportunities to enjoy the Florida sunshine. The community's convenient Naples location puts you close to Fifth Avenue South, Tin City, shopping, restaurants and the beautiful Gulf beaches. Winterpark offers an active, welcoming lifestyle in a location that makes it easy to enjoy everything Naples has to offer. Whether you're looking for a seasonal getaway or a year-round residence, this updated condo offers the perfect combination of location, lifestyle and value. 4027 Northlight Drive #4 — offered at $259,900.

4027 Northlight Dr Unit 4, Winter Park
4230 Jack Frost Ct Unit 4402, Naples
$230,000
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
3574 Antarctic Cir Unit 2107, 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
4001 Ice Castle Way Unit 1, Naples
$215,000
2 Beds ⋅ 2 Baths ⋅ 226026798 MLS ⋅ Winterpark BLDG.
FIRST FLOOR, END UNIT, PAVERED PATIO! 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 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 PAVERED PATIO, perfect for year-round enjoyment. 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
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