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$329,900
2 Beds ⋅ 2 Baths ⋅ 226019156 MLS
4140 Looking Glass Ln #3815 is a move-in-ready 2-bedroom, 2-bath condo for sale in Winterpark, one of Naples’ established communities with resort-style amenities and a convenient location. Offered at $329,900, this updated Naples condo features a fully redesigned kitchen with white cabinetry, stainless steel appliances, a stylish backsplash, large breakfast bar, and an open layout connecting the kitchen, dining, and living areas. The interior has a clean coastal feel with updated flooring, recessed lighting, modern finishes, and a spacious living room overlooking a peaceful outdoor setting. The owner’s suite includes custom closet space and an updated bathroom with a walk-in shower. The second bedroom and bathroom provide flexibility for guests, seasonal use, or a home office. A standout feature is the custom laundry and wine cellar area, adding valuable function and a unique touch. Winterpark amenities include a resort-style community pool, clubhouse, community room, pickleball, tennis, bocce court, bike and jog path, bike storage, extra storage, and internet access. The HOA includes cable, insurance, internet/WiFi access, irrigation water, lawn and land maintenance, reserves, sewer, street lights, street maintenance, trash removal, and water. For buyers searching for Naples condos for sale, a move-in-ready condo in Winterpark, or a well-updated property near shopping, dining, beaches, and downtown Naples, this is a strong opportunity.

4140 Looking Glass Lane Unit 7, Naples
$249,000
2 Beds ⋅ 2 Baths ⋅ 226017233 MLS
Welcome to an exceptional opportunity to own an upstairs residence in the highly sought-after Winterpark community—where value meets vision and the potential to create your dream Naples retreat awaits. Positioned in a prime Naples location, this 2-bedroom, 2-bath condominium offers a light-filled layout with an expansive living and dining area, ready to be reimagined with your personal style and design vision. The screened balcony provides a peaceful outdoor space overlooking lush tropical landscaping—perfect for morning coffee or unwinding after a day at the beach. Inside, you’ll find a spacious primary suite, in-unit laundry, and a functional floor plan that serves as the perfect canvas for updates, renovations, or a full custom transformation. What truly sets this property apart is its placement within Winterpark—one of Naples’ most desirable, amenity-rich communities known for its vibrant lifestyle and classic Florida charm. Residents enjoy access to one of the largest resort-style pools in Naples, beautifully maintained grounds, newly updated pickleball and tennis courts, and an active social atmosphere that makes it easy to feel at home. Located just minutes from 5th Avenue South and Olde Naples, as well as world-renowned Gulf beaches, this property offers unmatched convenience to fine dining, boutique shopping, art galleries, and coastal living at its finest. Whether you’re seeking a seasonal escape, investment opportunity, or a full-time residence to customize and make your own, this is your chance to unlock the full potential of Naples living in a community that truly embodies the Florida lifestyle.

3420 Frosty Way Unit 4910, 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
$309,900
2 Beds ⋅ 2 Baths ⋅ 226015387 MLS
Charming 2 Bed, 2 Bath in Desirable Winterpark – Prime Naples Location Nestled in the heart of sunny Naples, this beautifully updated 2-bedroom, 2-bathroom condo in Winter park offers the perfect blend of comfort, style, and convenience. The open-concept layout is ideal for entertaining, while the spacious screened-in lanai provides a peaceful space to relax and unwind. Located just a short drive to 5th Avenue, Naples Beach, Publix, and a variety of restaurants and shops, this highly sought-after community.

4030 Northlight Drive, Naples
$284,900
2 Beds ⋅ 2 Baths ⋅ 226012607 MLS
Welcome to Winterpark, one of Naples most sought-after communities just minutes from downtown and the pristine Gulf beaches. This beautifully updated 2-bedroom, 2-bath 1st floor condo offers a perfect blend of modern style and effortless Florida living. Step inside to an open, light-filled layout designed for both comfort and entertaining. Darkwood accents & cabinetry in the kitchen and breakfast bar, custom tile work and exquisite finishes throughout. Enjoy your morning coffee or unwind in the evening on the spacious lanai, a perfect private retreat with a relaxing, tropical feel. Winterpark is known for its resort-style amenities, including one of the largest pools in Naples, newly updated pickleball and tennis courts, and a vibrant, active social atmosphere. Surrounded by lush green spaces and charming scenery, the community captures the essence of classic Florida living. Ideally located just minutes from 5th Avenue South, Olde Naples, shopping, dining, and the beach, this property is perfect as a full-time residence, seasonal getaway, or investment opportunity. Come experience it for yourself—this one won’t last.

4150 Looking Glass Lane Unit 3903, Naples
$250,000
2 Beds ⋅ 2 Baths ⋅ 226011974 MLS
Nicely appointed 2ND FLOOR UNIT with screened-in deck. Ready to move in. Newer refrigerator and Range in kitchen. A/C is 3 years old. Extensive amenities in the complex including, Tennis Courts, Pickleball, Bocce Ball, Shuffleboard, and a Resort style pool. Walking distance to shopping(Home Depot ,Publix, Walgreen's) and restaurants. Pets are Allowed.

4031 Ice Castle Way Unit 3306, Naples
$209,500
2 Beds ⋅ 2 Baths ⋅ 2026009632 MLS
Best Value in Winterpark – First Floor • Turnkey • Impact Windows • New A/C • Conventional Financing On of the Lowest-priced first-floor condo in Winterpark. This turnkey-furnished home offers an incredible opportunity to own in one of Naples’ most desirable communities while leaving room in your budget to update and personalize it over time. The home offers a comfortable, functional layout with one nicely updated bathroom while providing an opportunity to personalize the remaining spaces to your own taste and style. Major improvements have already been completed, including updated plumbing, impact windows and an impact sliding glass door, a new A/C (2024), and a new water heater (2023), allowing you to focus on making it your own. For added peace of mind, the condominium association carries a master flood insurance policy. The property also qualifies for conventional financing, offering greater flexibility for buyers. Winterpark is known for its lush, walkable setting, spectacular resort-style pool, tennis courts, and welcoming atmosphere. Ideally located just minutes from downtown Naples, 5th Avenue South, shopping, dining, and the beautiful Gulf beaches, you’ll enjoy everything Southwest Florida has to offer. Quarterly HOA dues are $1,920 and include outstanding community amenities and exterior maintenance. Pets and rentals are permitted, adding to the property’s versatility. Motivated sellers have priced this home to sell. If you’ve been searching for an affordable opportunity to own in one of Naples’ most popular communities, this is one you won’t want to miss.

4070 Looking Glass Lane Unit 3101, Naples
$240,000
2 Beds ⋅ 2 Baths ⋅ 226009042 MLS
Seller Says Sell! Price reduction for this amazing condo in highly sought after Winterpark. Discover the perfect blend of comfort, style, and location in this spacious second-floor corner condo in beautiful Naples. Featuring vaulted ceilings and serene garden views, this light-filled residence offers privacy and tranquility within the lush, peaceful community of Winterpark. This updated 2-bedroom, 2-bath home showcases an open, airy layout with neutral tones that complement any décor. The remodeled kitchen features modern cabinetry, quartz countertops, stainless steel appliances, and a convenient breakfast bar that flows seamlessly into the expansive living and dining areas—ideal for entertaining or relaxing at home. Both bathrooms have also been tastefully renovated. Other updates include a newer A/C, a brand new water heater, and a roof that's only a year old for added peace of mind. Flood insurance is covered by the association. Another advantage is the in-unit laundry room with washer, dryer, and abundant storage. Enjoy Florida living year-round from the screened porch overlooking the garden, the large heated community pool, tennis courts and other playing courts, as well as walking and jogging paths. Other features include private assigned parking and plenty of additional guest parking for even more convenience. Extra private storage accompanies this property to store your bike or anything else you may need. The location is perfect, only a few minutes to Downtown Naples and its world renowned beaches, plus easy access to exceptional dining, shopping and entertainment options. Pet-friendly, rental-friendly and without age restrictions, this condo presents an excellent investment opportunity or seasonal retreat. While other units may be available in the community, this beautifully updated corner residence truly stands out—one you must see in person to fully appreciate.

4100 Looking Glass Lane Unit 3002, Naples
$225,000
2 Beds ⋅ 2 Baths ⋅ 2026010114 MLS
Welcome home to this beautifully maintained Winter Park condo offering over 1,200 square feet of comfortable living space with peaceful green space views. This spacious residence features 2 bedrooms and 2 bathrooms, providing an ideal layout for both everyday living and entertaining. Enjoy a vibrant, resort-style community with exceptional amenities, including a sparkling resort swimming pool, pickleball and tennis courts, bocce ball, scenic walking trails, and a variety of organized social activities. Recent major improvements include a newer A/C system and roof, offering added value and peace of mind. The monthly condo fee covers water, sewer, exterior insurance, exterior maintenance, cable service, landscaping, and full access to all community amenities, helping simplify ownership. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this property offers flexibility with both short-term and annual rentals permitted, subject to community restrictions.

4200 Looking Glass Lane Unit 4204, Naples
$259,000
2 Beds ⋅ 2 Baths ⋅ 2025014071 MLS
Excellent unit, less than 5 minutes from Naples' pristine beaches, pier, restaurants, and more. This bright and spacious second-floor condo unit is perfect for a small family or as a vacation rental. Very well-maintained, you will not be disappointed. Reasonable HOA fees and amazing amenities, including a pool, multiple tennis courts, and many more, in this great community. Furniture is negotiable

4079 Northlight Drive Unit 1802, Naples