Winterpark Homes with With Approval Pets

Welcome to Winterpark, an enchanting subdivision nestled in the heart of Naples, Florida, within the picturesque Collier County. This delightful community offers a perfect blend of serene living and vibrant lifestyle, making it an ideal haven for families, retirees, and professionals alike.

As you stroll through the tree-lined streets of Winterpark, you’ll discover beautifully designed homes that exude charm and character. With a variety of architectural styles and thoughtfully landscaped yards, each residence reflects the warmth and welcoming spirit of the neighborhood. The homes here are not just places to live; they are sanctuaries that foster a sense of belonging.

One of the standout features of Winterpark is its pet-friendly policy. For those who consider their furry friends as part of the family, this community is a perfect match. With approval for pets, you can enjoy the companionship of your beloved animals while also taking advantage of the ample green spaces and walking trails nearby. Imagine leisurely walks with your dog along the scenic paths, or enjoying a sunny afternoon at one of the local parks, all while soaking in the beauty of Florida's natural landscape.

In addition to its inviting atmosphere, Winterpark is conveniently located near Naples’ pristine beaches, upscale shopping, and gourmet dining options. The vibrant culture and recreational activities available in the area ensure that there’s always something to do, whether you prefer a day of relaxation by the shore or an evening of fine dining with friends.

Discover the charm of Winterpark, where community spirit meets the joys of coastal living, and where your pets are welcome to join in the fun!

Newest Winterpark Homes with With Approval Pets

$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

$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

$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, Other

$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

$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

$224,000

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! 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 LN Unit 1303, 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

$339,000

2 Beds ⋅ 2 Baths ⋅ 226005552 MLS ⋅ Winterpark BLDG.

Discover comfortable and easy Florida living in this inviting 2-bedroom, 2-bath condo located in the highly desirable Winterpark community. This first-floor residence offers a well-designed floor plan with a welcoming living and dining area, a thoughtfully arranged kitchen, and two comfortably sized bedrooms with excellent closet storage. The primary suite includes an en-suite bath and relaxing views of the community’s green space. Step outside to enjoy Winterpark’s resort-style amenities, including one of the largest community pools in Naples, a clubhouse, pickleball and tennis courts, bocce, and beautifully maintained walking paths. Residents appreciate the convenient East Naples location—just minutes from downtown 5th Avenue, shopping, dining, and Naples’ world-famous beaches. Whether you're seeking a seasonal retreat, full-time residence, or investment property, this Winterpark condo offers wonderful value and a uniquely comfortable Naples lifestyle.

4180 Looking Glass LN Unit 4102, 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.