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$255,000

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.

2 Beds ⋅ 2 Baths ⋅ 226028684 MLS

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 Circle Unit 2107, Naples

Listing Courtesy of John R Wood Properties

$245,000

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.

2 Beds ⋅ 2 Baths ⋅ 226026798 MLS

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

Listing Courtesy of Premiere Plus Realty Company

$262,000

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.

2 Beds ⋅ 2 Baths ⋅ 226027202 MLS

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

Listing Courtesy of Premiere Plus Realty Company

$249,000

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! 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.

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! 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.

3816 Snowflake Lane Unit 1303, Naples

Listing Courtesy of Broker Brothers LLC

$248,000

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!

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

Listing Courtesy of Re/Max Alliance Group

$329,900

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.

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

Listing Courtesy of Keller Williams Realty Naples

$249,000

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.

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

Listing Courtesy of William Raveis Real Estate

$284,900

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.

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

Listing Courtesy of LPT Realty, LLC

$250,000

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.

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

Listing Courtesy of Realty World Top Producers Rlt

$225,000

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.

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

Listing Courtesy of Portside Property Group