Winterpark Homes under $250,000

Winterpark Homes under $250,000

Welcome to Winterpark, a hidden gem nestled in the heart of Naples, Florida, within the picturesque Collier County. This charming community offers an exceptional opportunity for homebuyers seeking affordable living in one of Florida's most desirable locations. With homes available under $250,000, Winterpark stands out as a beacon of value in a market often characterized by higher price points.

Winterpark is designed to foster a sense of community, featuring well-maintained streets and lush green spaces that invite residents to enjoy the great outdoors. The neighborhood is perfect for families, retirees, and anyone in between, providing a welcoming environment where neighbors become friends.

Residents of Winterpark are just minutes away from Naples' stunning beaches, vibrant shopping districts, and a variety of dining options that cater to every palate. Whether you're looking to indulge in fresh seafood or explore local boutiques, the city's rich offerings are sure to delight.

In addition to its prime location, Winterpark boasts a range of homes that cater to diverse lifestyles. From cozy single-family residences to charming townhomes, there’s something for everyone. Each property is designed with comfort and functionality in mind, making it easy for you to settle in and make it your own.

If you're searching for an affordable home in a beautiful locale, look no further than Winterpark in Naples. Here, you can embrace the Florida lifestyle without breaking the bank. Come discover your new home today!

Newest Winterpark Homes under $250,000

4100 Looking Glass Lane Unit 7, Naples
$239,900
2 Beds ⋅ 2 Baths ⋅ 226040493 MLS
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 Lane Unit 7, Naples
4200 LOOKING GLASS Lane Unit 4207, Naples
$229,000
2 Beds ⋅ 2 Baths ⋅ 226040038 MLS
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 Lane Unit 4207, Naples
4065 Northlight Drive Unit 1807, Naples
$250,000
2 Beds ⋅ 2 Baths ⋅ 226037301 MLS
!!!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 Drive Unit 1807, Naples
4038 Northlight Drive Unit 1506, Naples
$249,900
2 Beds ⋅ 2 Baths ⋅ 226038074 MLS
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 Drive Unit 1506, Naples
4079 Northlight Drive Unit 2, Naples
$220,000
2 Beds ⋅ 2 Baths ⋅ 226034559 MLS
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 Drive Unit 2, Naples
4096 Northlight Drive Unit 1709, Naples
$239,000
2 Beds ⋅ 2 Baths ⋅ 2026040990 MLS
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 Drive Unit 1709, Naples
4073 Northlight Drive Unit 1803, Naples
$249,000
2 Beds ⋅ 2 Baths ⋅ 226033685 MLS
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 Drive Unit 1803, Naples
4230 Jack Frost Court Unit 4402, Naples
$230,000
2 Beds ⋅ 2 Baths ⋅ 226028571 MLS
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 Court Unit 4402, Naples
4001 Ice Castle Way Unit 1, Naples
$215,000
2 Beds ⋅ 2 Baths ⋅ 226026798 MLS
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
3816 Snowflake Lane Unit 1303, Naples
$199,999
2 Beds ⋅ 2 Baths ⋅ 226024603 MLS
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! Roof 2 years old - AC 2018 - Water heater 2020 - 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. Insurance included in the HOA fee that also includes all amenities. Cable and internet not included in HOA fees.

3816 Snowflake Lane Unit 1303, Naples
3532 Antarctic Circle Unit 2216, Naples
$248,000
2 Beds ⋅ 2 Baths ⋅ 226020005 MLS
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 Circle Unit 2216, Naples
4050 Ice Castle Way Unit 2812, Naples
$239,000
2 Beds ⋅ 2 Baths ⋅ 226016168 MLS
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
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