Winterpark Real Estate

Winterpark Real Estate

**Discover the Enchantment of Winterpark, Naples, FL**

Nestled in the heart of Naples, Florida, Winterpark is a hidden gem that perfectly blends the charm of suburban living with the vibrancy of coastal life. This picturesque neighborhood is known for its lush landscapes, tree-lined streets, and a welcoming community atmosphere that makes it an ideal place to call home.

Winterpark is characterized by its well-maintained homes, many of which boast stunning architectural designs and spacious yards. The neighborhood is perfect for families, retirees, and anyone looking to enjoy a serene lifestyle without sacrificing convenience. Residents appreciate the close-knit community feel, where neighbors become friends, and gatherings are common.

One of the standout features of Winterpark is its proximity to Naples’ pristine beaches and world-class amenities. Just a short drive away, you can bask in the sun on the sandy shores of the Gulf of Mexico or explore the vibrant downtown area filled with upscale dining, boutique shopping, and cultural attractions. For nature enthusiasts, the nearby parks and nature reserves offer a plethora of outdoor activities, from hiking and biking to birdwatching and kayaking.

Families will also find top-rated schools within easy reach, making Winterpark a fantastic choice for those with children. With a strong sense of community and a wealth of recreational opportunities, Winterpark is not just a neighborhood; it’s a lifestyle.

Whether you’re looking to settle down or invest in a vacation home, Winterpark in Naples, FL, invites you to experience the perfect blend of relaxation and adventure. Come and discover why this enchanting neighborhood is the ideal place to live, work, and play.

Newest Listings in Winterpark

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
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
$249,000
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. See attached 10k grant program provided by 5/3Bank.

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
Start Your Search

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.

How much is your home worth?

Get instant property value now!