3 Bedroom 2 Bath homes for sale & real estate in Winding Cypress, FL

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ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Rare villa opportunity in Winding Cypress! This turnkey, fully furnished villa sits on an extra-large, ultra-private lot with exceptional spacing between neighbors, creating a peaceful and open feel that is hard to find. The backyard is a retreat, featuring a saltwater private pool framed by mature cypress trees, colorful landscaping and wide natural preserve views. Inside, the home offers thoughtful upgrades including 8-foot interior doors, new bedroom flooring, refreshed landscaping and built-in garage storage that helps keep everything organized. As a natural gas home, it features gas cooking and provides flexibility for future enhancements, offering efficiency and convenience. Living in

$600,000

3 beds2 baths1,554 sq ft

7167 Live Oak Dr, Naples, FL 34114

Extra-large lot • New bedroom flooring • 6,098 sq ft lot

OPEN DEC 7, 1PM TO 4PM

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
The Martin Ray Floor Plan is PRIVACY-PRIVACY-PRIVACY. An exceptional model styled home on a premium lot with rare, unobstructed views of the lake and the Preserve. This residence offers unmatched privacy and outdoor living, with two standout features: an expansive screened lanai with custom accent lighting, saltwater, heated pool, plus an outdoor dry bar with refrigerator and cabinetry—all designed to create your own private resort overlooking nature. Inside, every detail reflects model-quality craftsmanship. The home showcases a chef’s kitchen with Alexa-linked gas 5 Burner stove/oven, upgraded cabinetry with pull-out drawers, upgraded appliances. A butler’s wine ba

$1,188,000

3 beds2 baths2,166 sq ft

7457 Winding Cypress Dr, Naples, FL 34114

Screened lanai • Unobstructed views • Butler's wine bar

OPEN TODAY, 1PM TO 4PM

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Perfection is the only way to describe this home! It shows like a model as it has been rarely lived in since built barely three years ago. Welcome to the desirable Pulte/DiVosta Mystique Model located in the popular amenity rich community of Winding Cypress. This waterfront property sits on a dead-end cul-de-sac and is loaded with owner and builder upgrades. It's impeccably decorated and furnished and could come turnkey providing the new owner with everything you'll ever need to begin living in paradise! The Mystique’s footprint, a 3 bed, 2 bath plus optional den offers the sought after open kitchen, great room, and dining area concept with split bedrooms to ensure comfort and privacy

$925,000

3 beds2 baths2,094 sq ft

6699 Pennyroyal Dr, Naples, FL 34114

Natural gas cooktop • Custom pool • Epoxy painted floor

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Sense the comfort and beauty of this magnificent home the minute you enter the foyer and see the view out to the inviting pool and spa. This 3 bedroom, plus separate den, great room floor-plan is perfect for entertaining or just a lovely place to call home. These original owners have impeccably maintained the home making it feel brand new. Built in 2021 it boasts a chef's delight kitchen with stainless steel appliances, center island and breakfast bar, natural gas cooktop/range, pull-out drawers, quartz counter-tops, recessed and pendant lighting, and more! The cook of the house will love it! The great room and dining area are adjacent to the kitchen. An extra plus is the den with double r

$899,000

3 beds2 baths2,084 sq ft

6856 Winding Cypress Dr, Naples, FL 34114

Zero corner doors • Extended lanai • 2 garage spots

3D WALKTHROUGH

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Sophisticated Villa Living in Winding Cypress – OVER 100K In SAFTEY AND SECURITY UPGRADES! Priced to Sell and FULLY FURNISHED. An extraordinary opportunity awaits in the highly sought-after Winding Cypress community—this impeccably upgraded 3-bedroom, 2-bathroom villa is set on the largest homesite in the neighborhood, offering both privacy and an expansive outdoor retreat. Thoughtfully enhanced with luxury upgrades and high-end finishes, this residence is a rare find, now priced competitively for discerning buyers seeking exceptional value. From the moment you step inside, you’ll appreciate the seamless open-concept design, accentuated by elegant crown molding and designe

$569,000

3 beds2 baths1,554 sq ft

7176 Live Oak Dr, Naples, FL 34114

High-end finishes • Luxury upgrades • Granite countertops

Property at 6902 Winding Cypress Dr, Naples, FL 34114, 3 beds, 2 baths

$950,000

3 beds2 baths2,084 sq ft

6902 Winding Cypress Dr, Naples, FL 34114

Property at 7057 Live Oak Dr, Naples, FL 34114, 3 beds, 2 baths

$819,000

3 beds2 baths2,230 sq ft

7057 Live Oak Dr, Naples, FL 34114

Property at 6787 Pennyroyal Dr, Naples, FL 34114, 3 beds, 2 baths

$959,900

3 beds2 baths2,186 sq ft

6787 Pennyroyal Dr, Naples, FL 34114

Property at 7670 Jacaranda Ln, Naples, FL 34114, 3 beds, 2 baths

$749,900

3 beds2 baths1,594 sq ft

7670 Jacaranda Ln, Naples, FL 34114

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OPEN TODAY, 2:30PM TO 4:30PM

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Experience the Ole' Lely Resort Lifestyle: Turnkey Luxury Awaits Welcome to this rarely available, meticulously maintained Santa Ana end-unit model in the prestigious Ole at Lely Resort. This stunning residence is offered turnkey furnished, allowing you to simply unpack and start enjoying paradise immediately. This home boasts 3 bedrooms, 2.5 bathrooms, and an attached 2-car garage within a bright, open-concept floor plan. This owner has spared no expense on updates, including a gourmet kitchen featuring rich wood cabinetry, stainless steel appliances, striking granite countertops, and a modern tile backsplash, complemented by recessed LED lighting and a large pantry. The main level is per

$499,900

3 beds2.5 baths1,715 sq ft

8964 Malibu Ln #11, Naples, FL 34113

Gourmet kitchen • Resort-style pool • $1,249 HOA

OPEN TODAY, 1PM TO 4PM

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
SPACIOUS OPEN LAYOUT – OVERSIZED BEDROOMS – HURRICANE SHUTTERS WITH ABUNDANT NATURAL LIGHT! This beautifully maintained 3-bedroom, 2-bath home offers 1,437 sq. ft. of bright, open living designed for comfort, functionality, and effortless entertaining. The expansive living, dining, and kitchen areas flow seamlessly together, creating a welcoming environment for everyday living, while oversized bedrooms provide flexibility, privacy, and plenty of space for family or guests. Large windows and durable hurricane shutters fill the home with natural light while providing safety and peace of mind, highlighting the warm, airy atmosphere and modern style throughout. Every detail has been

$489,000

3 beds2 baths1,437 sq ft

8700 Querce Ct, Naples, FL 34114

Guard gated entrance • Resort style pool • Plantation shutters

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Terrific property in Ole. Great rental history. Attached 2 car garage, nicely appointed interior, private balcony, secure entry. Superb location near the Ole town center, close to dining, shopping and entertainment. Minutes to Marco Island but why go there when you have dining, movies, a community pool and so much more right at your fingertips. Lease is currently month to month.

$399,900

3 beds2 baths1,770 sq ft

8941 Malibu St #1, Naples, FL 34113

Secure entry • Attached garage • Community pool

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Stunning Luxurious Oakmont Model offers beautiful panoramic Southwestern Lakefront Exposure – in a cul-de-sac. Every detail has been elevated with luxurious European furnishings and curated interior design creating a sophisticated turnkey living experience. Introducing a beautifully refined 3 bedroom plus den Oakmont Model in the highly desirable community of Verona Walk showcasing premium upgrades and impeccable style. Impressive list of luxury finishes, interior custom quartz kitchen with premium finishes & European steel appliances including Bosch refrigerator and Bosch wine cooler, Bosch dishwasher, Miele Washer, elegant custom wall unit in the great room, 10- & 12-foo

$849,000

3 beds2.5 baths2,000 sq ft

7063 Toscana Ct, Naples, FL 34114

Cul-de-sac • Elevated private spa • 2 garage spots

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Welcome home to effortless coastal living, where every detail has already been perfected, and all that’s left to do is move in and start enjoying the Florida lifestyle you’ve been dreaming of. In the sought-after community of Ole, this beautifully remodeled San Pablo residence combines timeless design with a relaxed, beach-inspired aesthetic. Every inch has been thoughtfully updated, from the new flooring and lighting to the custom tilework and fresh, airy finishes that bring a sense of calm to the space. Offered turnkey furnished, it’s a rare opportunity to step directly into a professionally designed home without the hassle of sourcing contractors or waiting on renovatio

$479,000

3 beds2 baths1,771 sq ft

9110 Capistrano St S #8402, Naples, FL 34113

Desirable layout • Custom tilework • Turnkey furnished

3D WALKTHROUGH

ABOUT THIS HOME
3 Bedroom 2 Bath Homes for Sale in Winding Cypress, FL
Ready for immediate occupancy: Experience the coveted Santa Cruz floor plan in Ole at Lely Resort! This immaculate 3-bedroom townhouse offers the ultimate in luxury and convenience, featuring no carpet throughout and a bright, white kitchen with stainless steel appliances. Enjoy indoor-outdoor living with a welcoming front porch and a screened balcony off the kitchen, complete with a retractable screen – perfect for enjoying the Florida breeze. This turnkey residence is ideally situated within one of Ole's exclusive Quads, providing a semi-private pool, BBQ grills, and a relaxing sitting area just for quad residents. Inside, the spacious, multi-level design creates a unique and charmi

$449,900

3 beds2.5 baths1,800 sq ft

9063 Capistrano St N #4408, Naples, FL 34113

Bright white kitchen • No carpet • Front porch

Property at 14558 Manchester Dr, Naples, FL 34114, 3 beds, 2 baths

$605,000

3 beds2 baths1,760 sq ft

14558 Manchester Dr, Naples, FL 34114

Property at 8516 Benelli Ct, Naples, FL 34114, 3 beds, 2 baths

$850,000

3 beds2 baths2,188 sq ft

8516 Benelli Ct, Naples, FL 34114

Property at 14598 Grapevine Dr, Naples, FL 34114, 3 beds, 2 baths

$459,000

3 beds2 baths1,391 sq ft

14598 Grapevine Dr, Naples, FL 34114

Property at 14291 Manchester Dr, Naples, FL 34114, 3 beds, 2 baths

$719,000

3 beds2 baths2,116 sq ft

14291 Manchester Dr, Naples, FL 34114

Property at 9081 Albion Ln S #6508, Naples, FL 34113, 3 beds, 2.5 baths

$525,000

3 beds2.5 baths1,800 sq ft

9081 Albion Ln S #6508, Naples, FL 34113

Property at 14134 Nautica Ct, Naples, FL 34114, 3 beds, 2.5 baths

$625,000

3 beds2.5 baths1,841 sq ft

14134 Nautica Ct, Naples, FL 34114

Property at 8407 Benelli Ct, Naples, FL 34114, 3 beds, 2 baths

$749,000

3 beds2 baths2,188 sq ft

8407 Benelli Ct, Naples, FL 34114

Property at 9066 Albion Ln N #5104, Naples, FL 34113, 3 beds, 2 baths

$475,000

3 beds2 baths1,771 sq ft

9066 Albion Ln N #5104, Naples, FL 34113

Property at 9111 Capistrano St S #8302, Naples, FL 34113, 3 beds, 2.5 baths

$549,900

3 beds2.5 baths1,682 sq ft

9111 Capistrano St S #8302, Naples, FL 34113

Property at 14716 Cranberry Ct, Naples, FL 34114, 3 beds, 2 baths

$439,900

3 beds2 baths1,391 sq ft

14716 Cranberry Ct, Naples, FL 34114

Property at 9070 Albion Ln N #5801, Naples, FL 34113, 3 beds, 2.5 baths

$439,000

3 beds2.5 baths2,086 sq ft

9070 Albion Ln N #5801, Naples, FL 34113

Property at 9073 Rialto St #6002, Naples, FL 34113, 3 beds, 2 baths

$549,000

3 beds2 baths1,771 sq ft

9073 Rialto St #6002, Naples, FL 34113

Property at 14878 Windward Ln, Naples, FL 34114, 3 beds, 2.5 baths

$1,150,000

3 beds2.5 baths2,344 sq ft

14878 Windward Ln, Naples, FL 34114

Property at 16 Derhenson Dr, Naples, FL 34114, 3 beds, 2 baths

$289,900

3 beds2 baths1,392 sq ft

16 Derhenson Dr, Naples, FL 34114

3 Bedroom 2 Bath Homes for Sale in Winding Cypress

There are currently 9 3 bedroom 2 bath homes in Winding Cypress. 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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