Winding Cypress, FL homes for sale & real estate

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ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
This Summerwood floorplan is situated on a gorgeous lake and features 3 bedrooms, a den, 2 bathrooms, a gas heated pool and spa, and an extended 2-car garage. The home includes valuable storm-ready features such as a whole-home generator, impact-resistant windows and doors, and electric hurricane screens for added protection. Inside, the home is loaded with upgrades such as a custom built-in bar, TV stand and vanity, custom cabinetry in the primary closet, pantry, and laundry room, crown molding, tray ceiling, and a modern curated accent wall. Upgraded kitchen appliances and abundant storage complete the space. Embrace the Florida lifestyle with the open-concept layout seamlessly connecting

$925,000

3 beds2 baths2,003 sq ft

6779 Winding Cypress Dr, Naples, FL 34114

Custom cabinetry • Gas heated pool • Whole-home generator

NEW 27 HRS AGO3D WALKTHROUGH

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to this beautifully designed residence located within one of Naples’ most desirable gated communities. The open-concept floor plan is enhanced by volume and tray ceilings, plantation shutters throughout, and an extended driveway, adding both elegance and curb appeal. The spacious kitchen features granite countertops, a gas cooktop, wall oven, and ample cabinetry—making it both functional and inviting for everyday living and entertaining. Impact-resistant doors and windows provide peace of mind while framing tranquil lake views. Step outside to the expansive covered lanai with a summer kitchen, ideal for outdoor dining, entertaining, or enjoying a quiet morning coffee. Wh

$949,000

3 beds2 baths2,186 sq ft

7679 Winding Cypress Dr, Naples, FL 34114

Gated community • Tranquil lake views • Covered lanai

3D WALKTHROUGH

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to this stunning Tangerly Oak model home, thoughtfully designed with space, style, and Florida living in mind. This expansive 4-bedroom residence with a generous loft offers a flexible floor plan ideal for both everyday living and hosting guests, all enhanced by beautiful designer upgrades throughout. Step outside to an exceptional outdoor living space featuring a large covered lanai, resort-style pool and spa, and a fully equipped outdoor kitchen, perfectly positioned to capture long, wide lake views that create a peaceful and picturesque backdrop. Inside, the home is filled with light and refined finishes, showcasing the elevated craftsmanship and attention to detail that make the

$1,599,900

4 beds4 baths3,350 sq ft

7072 Live Oak Dr, Naples, FL 34114

Lake views • Resort style pool • Community amenities

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
This impeccably maintained residence offers an exceptional living experience. The open floor plan features three spacious bedrooms, a versatile den or flex room, and two full bathrooms. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated flooring. The added sunroom provides a tranquil space for relaxation or entertaining. The custom designed kitchen equipped with under-cabinet lighting, granite countertops, a wall oven with microwave, gas cooktop, matching range hood, soft-close drawers with pull outs, and a walk-in pantry for more than ample storge. This property sits on an oversized, private lot with tropical landscaping, a newly

$849,900

3 beds2 baths2,230 sq ft

7211 Live Oak Dr, Naples, FL 34114

Open floor plan • Sunroom • Granite countertops

OPEN SUN, 1PM TO 4PM

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Spacious & Immaculate accurately describe this outstanding retreat in the sought-after community of Winding Cypress. This rare, two-story Mystique footprint boasts 4 bedrooms, 3 full baths, a large den/office, and over 3160 square feet of adjusted living space, 3036 square feet under air. This residence was one of the last built in the community, 3 years new, and shows like a model home. Located on a very private lot on a cul-de-sac, this salt water pool home with private spa is meticulously one-owner maintained, beautifully decorated, and loaded with builder upgrades. For peace of mind, the owners added a whole house generator as well. The expansive, upstairs addition includes a huge

$1,150,000

4 beds3 baths3,036 sq ft

6825 Greenbriar Ct, Naples, FL 34114

Private spa • Private lot • Cul de sac

Property at 6698 Pennyroyal Dr, Naples, FL 34114, 3 beds, 3 baths

$943,000

3 beds3 baths2,150 sq ft

6698 Pennyroyal Dr, Naples, FL 34114

Property at 7167 Live Oak Dr, Naples, FL 34114, 3 beds, 2 baths

$600,000

3 beds2 baths1,554 sq ft

7167 Live Oak Dr, Naples, FL 34114

Property at 7457 Winding Cypress Dr, Naples, FL 34114, 3 beds, 2 baths

$1,155,000

3 beds2 baths2,166 sq ft

7457 Winding Cypress Dr, Naples, FL 34114

Property at 6699 Pennyroyal Dr, Naples, FL 34114, 3 beds, 2 baths

$890,000

3 beds2 baths2,094 sq ft

6699 Pennyroyal Dr, Naples, FL 34114

Property at 7248 Live Oak Dr, Naples, FL 34114, 2 beds, 2 baths

$639,900

2 beds2 baths1,685 sq ft

7248 Live Oak Dr, Naples, FL 34114

Property at 7412 Winding Cypress Dr, Naples, FL 34114, 4 beds, 4 baths

$1,595,000

4 beds4 baths3,656 sq ft

7412 Winding Cypress Dr, Naples, FL 34114

Property at 7520 Blackberry Dr, Naples, FL 34114, 3 beds, 3 baths

$1,160,000

3 beds3 baths2,496 sq ft

7520 Blackberry 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

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

$925,000

3 beds2 baths2,084 sq ft

6902 Winding Cypress Dr, Naples, FL 34114

Property at 7690 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$610,000

2 beds2 baths1,554 sq ft

7690 Jacaranda Ln, Naples, FL 34114

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

$949,900

3 beds2 baths2,186 sq ft

6787 Pennyroyal Dr, Naples, FL 34114

Property at 7602 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$529,000

2 beds2 baths1,554 sq ft

7602 Jacaranda Ln, 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 6770 Pennyroyal Dr, Naples, FL 34114, 3 beds, 3 baths

$825,000

3 beds3 baths2,128 sq ft

6770 Pennyroyal Dr, Naples, FL 34114

Property at 7658 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$534,500

2 beds2 baths1,554 sq ft

7658 Jacaranda Ln, Naples, FL 34114

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NEW 2 HRS AGO

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
ABSOLUTELY LOVELY RENOVATED 2 BEDROOM, 2 BATHROOM MANUFACTURED HOME IN POPULAR ENCHANTING SHORES COOPERATIVE. Lovingly cared for and beautifully maintained. This house comes completely furnished and turn key the home features two large lanais, both enclosed and furnished tastefully the kitchen features, Richwood, cabinetry and granite countertops along with new appliances. The guest bathroom is completely renovated has a gorgeous vanity and granite counter . This is a must see Home and is in absolutely move in condition. Enchanting Shores 55+ community is centrally located near everything Naples and Marco Island have to offer, including multiple eateries shops and services. Gulf of America

$152,900

2 beds2 baths1,130 sq ft

24 Turquoise Ave Unit 24T, Naples, FL 34114

Large lanais • Gorgeous vanity • Centrally located

NEW 7 HRS AGO

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to this well-appointed attached villa showcasing tranquil lake views, offering 2 bedrooms plus a den and 2 bathrooms. This move-in ready smart home delivers modern elegance and incredible value in desirable South Naples. No flood insurance required. Designed with both style and functionality in mind, the home features a spacious open layout with tile flooring throughout the main living areas and carpeted bedrooms. The flexible den is ideal for a home office or guest space. A large 2-car garage provides ample room for vehicles and additional storage. Enjoy full lake and protected preserve views from both the living room and the primary bedroom. The primary suite offers a walk-in clos

$445,000

2 beds2 baths1,515 sq ft

1170 Tranquil Brook Dr, Naples, FL 34114

Lake views • Open layout • Tile flooring

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
SELLER OFFERING BUYER CONCESSIONS. Beautifully maintained home located within a gated, amenity-rich community offering resort-style living. This thoughtfully designed residence features an open and functional floor plan filled with natural light, ideal for both everyday living and entertaining. Turn-key property offered fully furnished. The versatile den can easily be converted into an additional bedroom, offering flexibility and added value. The home offers well-appointed living spaces, a modern kitchen with ample cabinetry and counter space, comfortable bedrooms, and a private outdoor area perfect for relaxing or enjoying Florida’s lifestyle. Pride of ownership is evident throughout

$510,000

2 beds2 baths1,496 sq ft

1074 Enbrook Loop, Naples, FL 34114

Gated community • Open floor plan • Private clubhouse

(239) 776-5194

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Sparkling and fresh in move-in turnkey condition this wonderful winter retreat is the perfect spot to escape the frozen north. This home has been meticulously, updated and renovated. It offers recent appliances new roof and window air conditioners, as well as Central heat and air. Comfortable and inviting this property is priced to sell with nothing to do but enjoy it. Enchanting shorts is a highly desirable extremely well maintained community orientated active 55+ cooperative. The park offers a large variety of amenities and activities and is centrally located to all Collier County has to offer. Downtown Naples and Marco Island are in close proximity as our multitudes of eateries shops and

$82,500

1 bed1 bath700 sq ft

10 Jade Dr Unit 10J, Naples, FL 34114

Central heat and air • Recent appliances • Air conditioners

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
ADDORABLE AND AFFORDABLE WINTER GET AWAY IN THE FINEST PARK OF ITS KIND IN SWFL, ENCHANTING SHORES 55+ CO-OP. THIS 1 BEDROOM, ONE BATHROOM WELL MAINTAINED AND BEAUTIFULLY RENOVATED PARK MODEL FEATURES PORCELAIN TILE LANAI COMPLETELY FURNISHED. THE LANAI LEADS TO AN ATTACHED LAUNDRY ROOM/SHED. THE UPPER LEVEL HAS A COMFORTABLE SITTING AREA WITH LUXURY VINYL PLANK FLOORING, NEWLY FACED CABINETS, NEW COUNTERTOPS, PLENTY OF CUPBOARDS SPACE AS WELL AS NEWER APPLIANCES. THE COMFORTABLE BEDROOM OFFERS A QUEEN SIZE BED, LOTS OF STORAGE AND IS NEXT TO THE LOVELY REMODELED BATHROOM. THIS PARK MODEL HOME ALSO INCLUDES PAVED PARKING FOR TWO VEHICLES. ONLY MINUTES FROM POPULAR MARCO ISLAND AND A SHORT D

$82,500

1 bed1 bath550 sq ft

15 Jade Dr Unit 15J, Naples, FL 34114

Newly faced cabinets • Porcelain tile lanai • Electric fireplace

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to Henderson Creek Park, a true hidden gem where the charm of yesteryear meets a warm, close-knit community and timeless connections. This spacious 2-bedroom, 2-bath residence has been lovingly maintained and thoughtfully cared for, offering comfortable living with a sense of ease and simplicity. Enjoy the beauty of mature fruit trees right on your property, along with the convenience of a generous storage room and dedicated laundry room, features that add everyday practicality to this inviting home. Henderson Creek Park offers a voluntary HOA and an impressive array of amenities, including a heated pool and spa, shuffleboard courts, and boat launch with dockage, plus optional boat

$230,000

2 beds2 baths970 sq ft

5 Henderson Dr, Naples, FL 34114

Mature fruit trees • Shuffleboard courts • Spa

Property at 6740 Beach Resort Dr #12, Naples, FL 34114, 2 beds, 2 baths

$429,900

2 beds2 baths1,351 sq ft

6740 Beach Resort Dr #12, Naples, FL 34114

Property at 6660 Beach Resort Dr #16, Naples, FL 34114, 2 beds, 2 baths

$369,999

2 beds2 baths1,351 sq ft

6660 Beach Resort Dr #16, Naples, FL 34114

Property at 2170 Yellowfin Cir, Naples, FL 34114, 2 beds, 2 baths

$625,000

2 beds2 baths1,395 sq ft

2170 Yellowfin Cir, Naples, FL 34114

Property at 14370 Laguna Springs Ln, Naples, FL 34114, 4 beds, 4.5 baths

$2,285,000

4 beds4.5 baths2,947 sq ft

14370 Laguna Springs Ln, Naples, FL 34114

Property at 9108 Capistrano St S #7402, Naples, FL 34113, 3 beds, 2 baths

$429,900

3 beds2 baths1,770 sq ft

9108 Capistrano St S #7402, Naples, FL 34113

Property at 33 Henderson Dr, Naples, FL 34114, 2 beds, 2 baths

$284,600

2 beds2 baths1,330 sq ft

33 Henderson Dr, Naples, FL 34114

Property at 1108 Enbrook Loop, Naples, FL 34114, 3 beds, 2 baths

$485,000

3 beds2 baths1,503 sq ft

1108 Enbrook Loop, Naples, FL 34114

Property at 8595 Palermo Ct, Naples, FL 34114, 3 beds, 2 baths

$725,000

3 beds2 baths2,188 sq ft

8595 Palermo Ct, Naples, FL 34114

Property at 9105 Yuba Ln #7902, Naples, FL 34113, 2 beds, 2.5 baths

$429,000

2 beds2.5 baths1,776 sq ft

9105 Yuba Ln #7902, Naples, FL 34113

Property at 14362 Laguna Springs Ln, Naples, FL 34114, 4 beds, 4.5 baths

$2,300,000

4 beds4.5 baths2,947 sq ft

14362 Laguna Springs Ln, Naples, FL 34114

Property at 14088 Mirror Ct, Naples, FL 34114, 3 beds, 2 baths

$515,000

3 beds2 baths1,814 sq ft

14088 Mirror Ct, Naples, FL 34114

Property at 13598 Snapper Ln, Naples, FL 34114

$492,500

— beds— baths— sq ft

13598 Snapper Ln, Naples, FL 34114

Property at 13553 Snapper Ln, Naples, FL 34114

$350,000

— beds— baths— sq ft

13553 Snapper Ln, Naples, FL 34114

Property at 271 Pine Key Ln, Naples, FL 34114

$50,000

— beds— baths— sq ft

271 Pine Key Ln, Naples, FL 34114

Average home prices near Winding Cypress, FL

Cities

Neighborhoods
Zip Codes

Winding Cypress homes for sale
$907,500
Naples Reserve Golf Club homes for sale
$1,424,000
Naples Reserve homes for sale
$1,424,000
Falling Waters Beach Resort homes for sale
$374,900
Fiddler's Creek homes for sale
$775,000
Royal Fakapalm homes for sale
$697,000
South Naples homes for sale
$449,000

Winding Cypress, FL real estate trends

All Home Types trends in Winding Cypress, FL

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$800,000

-7.0% YoY | Nov 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Nov 2025

Growth

% YoY

Winding Cypress, FL

$800,000

-7.0%

See more Winding Cypress, FL market insights

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