Winterpark Homes with Guest Parking features

Winterpark Homes with Guest Parking features

Welcome to Winterpark, a charming subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This delightful community offers a perfect blend of tranquility and convenience, making it an ideal location for families, retirees, and everyone in between.

Winterpark is known for its beautiful tree-lined streets and meticulously maintained landscapes, providing residents with a serene environment to call home. The community features a variety of homes, each designed with comfort and style in mind. One of the standout features of Winterpark is the availability of guest parking, ensuring that your friends and family can easily visit and enjoy your lovely abode without the hassle of finding a spot.

As you stroll through the neighborhood, you'll discover a welcoming atmosphere, with friendly neighbors and a strong sense of community. The subdivision is conveniently located near top-rated schools, shopping centers, and recreational facilities, making everyday living a breeze. Whether you’re looking to spend a day at the nearby pristine beaches or enjoy a round of golf at one of the many local courses, Winterpark provides easy access to all that Naples has to offer.

In addition to its prime location, Winterpark boasts a variety of amenities that cater to an active lifestyle. From walking trails to parks, there’s something for everyone to enjoy. Experience the charm of Winterpark and discover why so many people are proud to call this community their home. Your dream home awaits in this idyllic Naples neighborhood!

Newest Winterpark Homes with Guest Parking features

4100 Looking Glass LN Unit 7, Naples
$239,900
2 Beds ⋅ 2 Baths ⋅ 226040493 MLS ⋅ Winterpark BLDG.
Welcome to Winterpark, where incredible amenities and a convenient Naples location come together! This first-floor, 2-bedroom, 2-bath condo offers comfortable Florida living with new laminate wood flooring, beautifully remodeled bathrooms, a spacious living and dining area, and a functional kitchen with a convenient breakfast bar. Enjoy the convenience of parking directly in front of your unit for easy access, along with additional storage located near the front entrance. The private screened lanai provides the perfect spot to relax and enjoy the tropical surroundings, with additional space at the rear of the unit offering the potential to add another lanai. The true highlight of Winterpark is its spectacular resort-style pool, considered by many to be one of the most impressive community pools in Naples! Surrounded by lush tropical landscaping, swaying palms, spacious sundecks, and plenty of lounge seating, this incredible pool creates a vacation-like atmosphere right in your own backyard. Residents also enjoy a clubhouse, tennis courts, and beautifully maintained grounds. Ideally located just minutes from Naples’ beautiful white-sand beaches, the shopping, dining, and entertainment of 5th Avenue South, and historic downtown Naples, this location puts everything Southwest Florida has to offer within easy reach. Whether you’re searching for a full-time residence, seasonal winter retreat, or investment opportunity, this condo offers a wonderful combination of location, amenities, convenience, and value. Come discover why Winterpark has remained a favorite among Naples residents for so many years

4100 Looking Glass LN Unit 7, Naples
4200 LOOKING GLASS LN Unit 4207, Naples
$229,000
2 Beds ⋅ 2 Baths ⋅ 226040038 MLS ⋅ Winterpark BLDG.
Discover the perfect blend of comfort, convenience and relaxed Naples living in the desirable Winterpark community. This inviting first-floor residence offers two spacious bedrooms, two full baths and a thoughtfully designed layout complemented by tile flooring throughout. The beautifully renovated kitchen brings a fresh, updated feel to the home, while a generously sized laundry room provides exceptional storage and everyday practicality. Enjoy quiet mornings or unwind in the evening on the charming open front porch. Winterpark offers a wonderful array of recreational amenities, including a resort-style swimming pool, tennis courts and bocce. Just minutes from downtown Naples, renowned beaches, shopping and dining, this residence presents an exceptional opportunity to enjoy the Southwest Florida lifestyle.

4200 LOOKING GLASS LN Unit 4207, Naples
4230 Jack Frost CT Unit 7, Naples
$259,900
2 Beds ⋅ 2 Baths ⋅ 226038133 MLS ⋅ Winterpark BLDG.
Offered turnkey furnished with desirable western exposure, this spacious, light-filled first-floor condominium presents an exceptional opportunity to enjoy the Naples lifestyle with low fees, resort-style amenities and outstanding convenience. Featuring two bedrooms, two full baths and 1,246 square feet of thoughtfully designed living space, this inviting residence offers a comfortable blend of updated interiors, ample interior storage, complemented by additional storage conveniently just outside the unit. and effortless indoor-outdoor living. Ideally near Starbucks, Publix and local restaurants, and just a short drive from Fifth Avenue South and Naples renowned Gulf beaches, the location appeals equally to seasonal enjoyment, year-round living or rental income potential. Inside, an open, airy atmosphere is enhanced by abundant natural light, newer wood-grain vinyl flooring and ceiling fans throughout. The renovated kitchen features stainless steel appliances and a refreshed design that complements the adjoining living and dining areas, creating an inviting setting for everyday living and entertaining. Sliding glass doors extend the living space to a screened lanai, where western exposure provides a relaxing backdrop for enjoying the afternoon sunshine and evening breezes. The spacious primary suite offers a peaceful retreat with a large walk-in closet and private bath, while the additional bedroom and full bath provide comfortable accommodations for guests. Exceptional storage is a standout feature, with a generous utility room, ample interior closet space and dedicated outdoor storage ideal for bicycles, grills and recreational essentials. Residents enjoy access to an expansive resort-style swimming pool, ideal for relaxing and embracing Southwest Florida’s year-round outdoor lifestyle. With remarkably low fees, turnkey convenience and excellent rental and income potential, this residence offers an appealing combination of comfort, flexibility and value. Its desirable Naples location places everyday conveniences, exceptional dining, boutique shopping and the white sand Gulf beaches within easy reach, creating an ideal setting for enjoying all coastal living has to offer.

4230 Jack Frost CT Unit 7, Naples
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
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
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
3420 Frosty WAY Unit 4902, 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
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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.

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