Recently Sold Homes in Winding Cypress, FL

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SOLD SEP 10, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Thoughtful price improvements, upgraded finishes throughout, an expanded kitchen island & a rare 4-foot extension in the garage sets this home apart - topped off by a stunning private pool overlooking the lake. This property offers exceptional appeal. This is a stunning Abbeyville home in Winding Cypress, a move-in ready! This immaculate residence is a must-see, featuring a fresh neutral palette, offering a spacious open split-bedroom floor plan with 2 bedrooms, a flex/den & 2 full bathrooms. Entertainment is elevated with flat-screen TVs mounted in both bedrooms & living area. Soaring ceilings enhanced by elegant molding, tray & coffered details, along with extra re

$750,000 Last sold price

2 beds2 baths1,685 sq ft

7128 Lily Way, Naples, FL 34114

SOLD OCT 30, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Location, location! This meticulously maintained and decorated Pinnacle model located on a corner lot with privacy on both sides including a lake and wooded area view is unique! Conveniently located within walking distance to clubhouse! The home features 3 bedrooms plus a den, 3 full baths and 3 car garage in this highly sought after natural gas community of Winding Cypress! This large lanai features a custom gas outdoor kitchen and a beautiful custom pool and spa! A must see to be appreciated! Home protection includes impact windows, sliders and electric shutters Winding Cypress offers a beautiful clubhouse, resort style pool and spa and waterfall feature! In addition to pickleball, tennis

$1,000,000 Last sold price

3 beds3 baths2,512 sq ft

7235 Clamshell Ln W, Naples, FL 34114

SOLD NOV 14, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Enjoy resort-style living in this Winding Cypress community near 5th Avenue and Marco Island. This home features a private pool, sunroom and the community’s largest covered lanai. Designed for year-round comfort, it offers a new air-conditioning system with additional cooling in the primary suite, impact glass throughout, and natural gas for efficiency and gourmet cooking. Inside, the oversized primary shower, upgraded tile and premium counters elevate everyday living. Set on a quiet street just a short distance to the Club at Winding Cypress, you’ll have dining, pickleball, tennis, bocce and a resort pool at your fingertips. Mature landscaping and preserve views ensure privacy

$800,000 Last sold price

3 beds2 baths2,230 sq ft

7049 Live Oak Dr, Naples, FL 34114

SOLD SEP 22, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
EXCEPIONAL in design and setting, this Pinnacle model commands southwest-facing LAKE AND PRESERVE VIEWS from one of the most private parcels within Winding Cypress. The residence is enhanced by an extended, Climate-Controlled 3 CAR GARAGE with a high-performance Polymer finish—offering utility and Esthetic. Interior features include 12’ ceilings, Tray Ceilings, tile flooring throughout, Plantation Shutters, and custom millwork. The open-concept floor plan includes a great room with Electric Sliding Doors leading to the lanai. The kitchen is equipped with Quartz countertops, a large island with built-in wine cooler, KitchenAid and Whirlpool appliances, and a natural gas cooktop.

$1,175,000 Last sold price

3 beds3 baths2,496 sq ft

7597 Blackberry Dr, Naples, FL 34114

SOLD NOV 17, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Tucked Away Treasure in Winding Cypress- Step into a slice of serenity with this charming attached villa, nestled in one of the most peaceful corners of Naples. Unlike the typical coastal designs so common in the area, this home offers a more rustic warmth—perfect for those who appreciate natural textures, cozy finishes, and a relaxed, grounded lifestyle. With 2 bedrooms, a versatile den, 2 full bathrooms, and a 2-car garage, this villa checks all the boxes for comfort and functionality. The open layout is inviting yet intimate, ideal for both quiet evenings and casual entertaining. The kitchen is equipped with natural gas—a rare find that’s perfect for those who love to

$455,000 Last sold price

2 beds2 baths1,554 sq ft

7642 Jacaranda Ln, Naples, FL 34114

Property at 7773 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$635,000 Last sold price

2 beds2 baths1,554 sq ft

7773 Jacaranda Ln, Naples, FL 34114

Property at 7788 Winding Cypress Dr, Naples, FL 34114, 3 beds, 3 baths

$975,000 Last sold price

3 beds3 baths2,496 sq ft

7788 Winding Cypress Dr, Naples, FL 34114

Property at 6870 Winding Cypress Dr, Naples, FL 34114, 3 beds, 2 baths

$860,000 Last sold price

3 beds2 baths2,084 sq ft

6870 Winding Cypress Dr, Naples, FL 34114

Property at 6839 Winding Cypress Dr, Naples, FL 34114, 3 beds, 3 baths

$1,260,000 Last sold price

3 beds3 baths2,515 sq ft

6839 Winding Cypress Dr, Naples, FL 34114

Property at 6767 Pennyroyal Dr, Naples, FL 34114, 3 beds, 2 baths

$990,000 Last sold price

3 beds2 baths2,185 sq ft

6767 Pennyroyal Dr, Naples, FL 34114

Property at 6787 Winding Cypress Dr, Naples, FL 34114, 2 beds, 2 baths

$710,000 Last sold price

2 beds2 baths1,654 sq ft

6787 Winding Cypress Dr, Naples, FL 34114

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SOLD OCT 17, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
This beautifully maintained Oakmont model home, nestled in the award winning, gated community of Verona Walk in Naples, Florida, offers a move-in ready retreat with a heated pool. Built by renowned builder DiVosta with solid poured concrete construction, this beautifully maintained 2-bedroom, 2.5-bath residence also features a versatile den and a spacious 2-car garage. The open-concept layout is enhanced by lofty ceilings, crown molding, and abundant natural light that fills every corner of the home. A centrally located whited kitchen with stainless steel appliances connects seamlessly to the expansive living and dining area- perfect for entertaining. A custom, floor-to-ceiling built-in wal

$650,000 Last sold price

3 beds2.5 baths1,983 sq ft

8507 Alessandria Ct, Naples, FL 34114

SOLD OCT 20, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
WHOLE HOUSE FRESHLY PAINTED WHITE" EPOXY GARAGE FLOOR looks beautiful. Welcome to your dream home in the highly sought-after Reflection Lakes of Naples! This single-family offers a comfortable open living space in a tranquil, gated community setting. Step inside this beautifully designed home featuring 3 spacious bedrooms, two full bathrooms, and an open-concept living area ideal for both entertaining and everyday living. The kitchen is a chef's delight featuring a breakfast area, granite countertops with seating, ample cabinetry and an open flow to the living room. The living room, bathed in natural light, opens seamlessly to a screened lanai where you can enjoy a private back yard wi

$525,000 Last sold price

3 beds2 baths2,048 sq ft

14813 Canton Ct, Naples, FL 34114

SOLD OCT 6, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Carlyle

$875,000 Last sold price

4 beds3.5 baths2,506 sq ft

8837 Zurigo Ln, Naples, FL 34114

SOLD NOV 3, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Capri

$410,000 Last sold price

2 beds2 baths1,540 sq ft

8275 Yasmina Way, Naples, FL 34114

SOLD NOV 3, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Delightful DUNWOODY TRAIL HOME! This charming 3-bedroom + den residence with a pool and spa offers 2,516 sq/ft of comfortable living space under air. Built in 2011, it features a 3-CAR GARAGE, an open-concept kitchen with a large island, and a bright southeast exposure that floods the home and pool deck with natural light. The spacious primary suite includes a walk-in closet, a luxurious bath with a separate tub and shower, and tranquil lake views as your backdrop. Outside, a large side yard is perfect for recreation, while the screened lanai and pool area invite year-round relaxation. At VeronaWalk, enjoy exceptional amenities: lagoon and lap pools, tennis, pickleball, a fitness center, we

$832,900 Last sold price

3 beds3 baths2,516 sq ft

8637 Julia Ln, Naples, FL 34114

SOLD NOV 21, 2025

ABOUT THIS HOME
Recently Sold Home in Winding Cypress, FL:
Beautiful Tifton 2 bedroom plus den, property includes bright inviting home with pool and spa overlooking beautiful water ways. Amenities include lap pool, community pool, fitness center, bocce courts, pickleball, tennis courts , basketball, kids play area, gated community, ice cream shop, hair salon, travel agency, post office, gas station and Real Estate Office.

$649,000 Last sold price

3 beds2 baths2,036 sq ft

8451 Benelli Ct, Naples, FL 34114

Property at 6620 Beach Resort Dr #609, Naples, FL 34114, 2 beds, 2 baths

$337,000 Last sold price

2 beds2 baths1,351 sq ft

6620 Beach Resort Dr #609, Naples, FL 34114

Property at 2 Sonderhen Dr, Naples, FL 34114, 2 beds, 2 baths

$280,000 Last sold price

2 beds2 baths1,813 sq ft

2 Sonderhen Dr, Naples, FL 34114

Property at 46 Grouse Rd #46, Naples, FL 34114, 3 beds, 2 baths

$62,000 Last sold price

3 beds2 baths1,456 sq ft

46 Grouse Rd #46, Naples, FL 34114

Property at 8073 Panther Trl #1403, Naples, FL 34113, 2 beds, 2 baths

$326,500 Last sold price

2 beds2 baths1,450 sq ft

8073 Panther Trl #1403, Naples, FL 34113

Property at 14151 Nautica Ct, Naples, FL 34114, 3 beds, 2 baths

$585,000 Last sold price

3 beds2 baths1,684 sq ft

14151 Nautica Ct, Naples, FL 34114

Property at 14166 Nautica Ct, Naples, FL 34114, 3 beds, 3 baths

$565,000 Last sold price

3 beds3 baths1,856 sq ft

14166 Nautica Ct, Naples, FL 34114

Property at 14741 Leeward Dr, Naples, FL 34114, 3 beds, 2 baths

$775,000 Last sold price

3 beds2 baths2,066 sq ft

14741 Leeward Dr, Naples, FL 34114

Property at 8941 Malibu St #105, Naples, FL 34113, 3 beds, 2.5 baths

$383,000 Last sold price

3 beds2.5 baths1,715 sq ft

8941 Malibu St #105, Naples, FL 34113

Property at 2076 Yellowfin Cir, Naples, FL 34114, 3 beds, 2 baths

$720,000 Last sold price

3 beds2 baths2,076 sq ft

2076 Yellowfin Cir, Naples, FL 34114

Property at 6700 Beach Resort Dr #11, Naples, FL 34114, 2 beds, 2 baths

$372,000 Last sold price

2 beds2 baths1,351 sq ft

6700 Beach Resort Dr #11, Naples, FL 34114

Property at 6750 Beach Resort Dr #8, Naples, FL 34114, 2 beds, 2 baths

$350,000 Last sold price

2 beds2 baths1,351 sq ft

6750 Beach Resort Dr #8, Naples, FL 34114

Property at 31 Turquoise Ave, Naples, FL 34114, 2 beds, 2 baths

$140,000 Last sold price

2 beds2 baths1,054 sq ft

31 Turquoise Ave, Naples, FL 34114

$410,000

— beds— baths1,540 sq ft

8463 Borboni Ct, Naples, FL 34114

$440,000

— beds— baths1,715 sq ft

9037 Alturas St #37, Naples, FL 34113

Recently Sold Homes in Winding Cypress

There are currently 11 recently sold homes for sale in Winding Cypress at a median listing price of $750K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Winding Cypress stay on the market for 136 days. Popular neighborhoods include Winding Cypress, Naples Reserve, Falling Waters Beach Resort, Fiddler's Creek, and South Naples. This map is refreshed with the newest listings in Winding Cypress every 15 minutes.

In the past month, 2 homes have been sold in Winding Cypress. In addition to houses in Winding Cypress, there were also 0 condos, 1 townhouse, and 0 multi-family units for sale in Winding Cypress last month. Find your dream home in Winding Cypress using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Winding Cypress are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Winding Cypress. Our Winding Cypress real estate stats and trends will give you more information about home buying and selling trends in Winding Cypress. If you're looking to sell your home in the Winding Cypress area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Winding Cypress with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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