Winding Cypress, FL homes for sale & real estate

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NEW 12 HRS AGOFLOOR PLAN

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Thank you for taking a look at the best value in sought after Winding Cypress! This pristine, 2-Story Summerwood Model, is loaded with options and is located on one of the nicest, private, and quiet lots in the entire community. This amazing home is perfectly situated on a lake's edge with a preserve backdrop. It's on a cul-de-sac with no thru traffic, and miles off of major roadways so it's incredibly quiet, private, with no road noise. If you are looking for a luxurious and functional space to entertain guests, or have them spend some overnights visiting, this is the property for you. Pride of original ownership is clear. With over 3200 square feet there's incredible room to entertain whi

$990,000

4 beds3 baths3,206 sq ft

7775 Winding Cypress Dr, Naples, FL 34114

Private quiet lot • Cul-de-sac • Lake's edge

EARLY ACCESSCOMPASS COMING SOON

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Situated on a private . 29 acre, end lot in the highly sought-after gated community of Winding Cypress, this home offers 3,696 square feet of refined Naples living space. Built in 2016, this two-story Pinnacle floor plan features 4 bedrooms, 4 full bathrooms, a versatile den and a spacious 3 car garage. The extended lanai with a premium long lake water view features a custom-built saltwater pool and spa combo plus a fully equipped built-in outdoor gas kitchen, a wonderful place to entertain family and friends. Step inside to discover wood-look tile flooring leading to a gourmet chef’s kitchen, stainless-steel appliances, natural gas cook top, a walk-in pantry and an expansive center i

$1,550,000

4 beds4 baths3,696 sq ft

7383 Mockingbird Ct, Naples, FL 34114

Gated community • Private end lot • Outdoor gas kitchen

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Enjoy the ease of Florida living in this beautifully maintained, Serenity floor plan single family villa, ideally situated on a corner lot in the gated, amenity-rich community of Winding Cypress. Being offered turnkey furnished, this thoughtfully designed residence has three bedrooms, two baths, and an inviting open-concept design, while combining comfortable living with effortless indoor-outdoor enjoyment. Tile flooring throughout, granite countertops, tile backsplash, and stainless-steel appliances create a timeless, welcoming kitchen. New AC in 2021. Plantation shutters throughout and a freshly painted interior add to the appeal, while the extended screened lanai provides a relaxing outd

$520,000

3 beds2 baths1,554 sq ft

7098 Live Oak Dr, Naples, FL 34114

Open-concept design • Turnkey furnished • Tile flooring

FLOOR PLAN

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Escape cookie-cutter living at 7670 Jacaranda, where custom millwork, extensive built-ins and thoughtful upgrades give this 2018-built home a character all its own. The open kitchen anchors the main living area with upgraded Samsung smart appliances, natural gas range, custom built-in coffee bar, sleek cabinetry and quartz counters, flowing naturally into the dining and living spaces. High ceilings with crown molding and transom windows create a light and bright interior with the utmost in privacy. The living room features a custom entertainment wall with fireplace and built-in cabinetry for a striking focal point. The attention to detail continues into the primary suite, where a dramatic c

$615,000

3 beds2 baths1,594 sq ft

7670 Jacaranda Ln, Naples, FL 34114

Quartz counters • Natural gas range • Custom millwork

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
This home has had a complete refresh with a lot of new improvements, new heat/ac units on both floors new pool pump and heater, new roof vents, new lanai screen, pavers on front and side with a refresh landscaping with sitting area, new epoxy garage flooring in extended garage to add a golf cart or storage, interior freshly painted, . this home is a martin ray style 2 story home features 2 split bedrooms on the first floor 2 full baths and office/ den , expanded kitchen with open pantry with wine cooler, new refridgerator. 2nd floor features a great room , private bedroom and full bath, great for guests or a needed private suite , The pool has a beautiful view of the lake and the pres

$925,000

3 beds3 baths2,300 sq ft

7235 Live Oak Dr, Naples, FL 34114

New lanai screen • Pavers on front • New pool pump

Property at 7247 Clamshell Ln, Naples, FL 34114, 4 beds, 4 baths

$1,549,000

4 beds4 baths3,656 sq ft

7247 Clamshell Ln, Naples, FL 34114

Property at 7230 Live Oak Dr, Naples, FL 34114, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,500 sq ft

7230 Live Oak Dr, Naples, FL 34114

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

$564,900

2 beds2 baths1,554 sq ft

7602 Jacaranda Ln, Naples, FL 34114

Property at 6825 Greenbriar Ct, Naples, FL 34114, 4 beds, 3 baths

$965,000

4 beds3 baths3,036 sq ft

6825 Greenbriar Ct, Naples, FL 34114

Property at 7072 Live Oak Dr, Naples, FL 34114, 4 beds, 4 baths

$1,450,000

4 beds4 baths3,350 sq ft

7072 Live Oak Dr, Naples, FL 34114

Property at 6907 Cocoplum St, Naples, FL 34114, 3 beds, 3 baths

$1,295,000

3 beds3 baths2,515 sq ft

6907 Cocoplum St, Naples, FL 34114

Property at 7156 Live Oak Dr, Naples, FL 34114, 3 beds, 2 baths

$590,000

3 beds2 baths1,554 sq ft

7156 Live Oak Dr, Naples, FL 34114

Property at 7700 Winding Cypress Dr, Naples, FL 34114, 5 beds, 3 baths

$1,250,000

5 beds3 baths2,950 sq ft

7700 Winding Cypress Dr, Naples, FL 34114

Property at 7478 Winding Cypress Dr, Naples, FL 34114, 3 beds, 3 baths

$1,349,500

3 beds3 baths2,634 sq ft

7478 Winding Cypress Dr, Naples, FL 34114

Property at 7666 Jacaranda Ln, Naples, FL 34114, 2 beds, 2 baths

$575,000

2 beds2 baths1,574 sq ft

7666 Jacaranda Ln, Naples, FL 34114

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NEW 26 HRS AGO

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
One or more photo(s) has been virtually staged, AI generated or rendered. The Ultimate Florida Escape in VeronaWalk! This popular DiVosta-built Capri model attached villa is constructed with solid poured concrete, is not in a flood zone, and offers a bright, open split-bedroom floor plan designed for comfortable Florida living. Meticulously maintained and recently upgraded from top to bottom, this move-in-ready home features 2 bedrooms plus a versatile den, 2 beautifully updated bathrooms, and an attached 2-car garage. Enjoy a fresh feel throughout with newly installed luxury vinyl plank flooring, fresh interior paint, new lighting fixtures, and ceiling fans. Soaring vaulted ceilings and a

$450,000

2 beds2 baths1,540 sq ft

8311 Yasmina Way, Naples, FL 34114

Not in a flood zone • Recently upgraded • 4,356 sq ft lot

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Close to beaches, downtown Naples and Marco Island, this beautiful second-floor condo in the Verandas at Tiger Island has soaring vaulted ceilings, which make it bright and open. Terracotta- flooring in the main areas and suits the relaxed, farmhouse décor. The upgraded kitchen has new cabinetry and a striking one-piece granite countertop, plus under-bar storage cabinets for entertaining essentials. A versatile flex room can serve as a guest space, dining room or home office. Great storage with walk-in closets …primary has 2 and second bedroom one. The split-bedroom plan offers privacy, while the hurricane shutters add peace of mind. The Verandas has its own community pool and

$354,900

2 beds2 baths1,460 sq ft

8003 Panther Trl #704, Naples, FL 34113

Second floor condo • Upgraded kitchen • Walk in closets

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
If you’ve been dreaming of owning a home and land in Naples, Florida, you will be thrilled to see this extremely affordable property! First, IT IS CLEAN INSIDE & OUT! Being sold furnished, this tranquil 1Br/1Ba home is situated within the Imperial Wilderness Condominium Association, a gated 55+ community where YOU OWN the LAND when you purchase your home (not a co-op or land lease). Plus, IWCA was never flooded! The exterior of this particular home features patio pavers, palm trees, a metal patio sunshade, a large shed, and a tranquil vibe. Inside you’ll appreciate the completely remodeled bathroom with a large walk-in shower. Additional updates include A/C, hot water tank

$89,000

1 bed1 bath408 sq ft

151 Cheetah Dr #151, Naples, FL 34114

Patio pavers • Large shed • Large walk-in shower

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Welcome to Imperial Wilderness, where affordable Southwest Florida living meets an active, resort-inspired lifestyle! Located within this gated 55+ community, this beautifully updated, turnkey residence offers something increasingly difficult to find: * * you own the land, with no lot rent * * , and enjoy exceptional amenities! Originally a 1997 Damon fifth wheel, the residence was expanded in 2004 with permanent additions, creating approximately 720 square feet of comfortable living space. This spacious one-bedroom, one-bath home features an inviting living area, well-equipped kitchen, abundant storage and numerous recent improvements. Inside, you'll appreciate updated luxury vinyl p

$95,000

1 bed1 bath700 sq ft

158 Cheetah Dr #158, Naples, FL 34114

2,178 sq ft lot • Garage • Community pool

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
OWNER FINANCING AVAILABLE. Affordable Florida living at its finest! This fully furnished 1-bedroom, 1-bath BEACH HOUSE is located in a highly desirable 55+ community with Gulf-access boat ramp—a rare find at this price point. Step inside to an open layout featuring a bright living area with bay window, built-in storage, and a functional kitchen with ample cabinetry and skylight. The spacious sunroom with vaulted ceilings adds valuable living space—perfect for relaxing or entertaining. The primary bedroom offers built-in storage, while the home also includes a laundry area with washer/dryer and walk-in shower for convenience. Enjoy resort-style amenities including clubhouse, pool

$79,500

2 beds2 baths600 sq ft

17 Jade Dr Unit 17J, Naples, FL 34114

Functional kitchen • Bright living area • Ample cabinetry

ABOUT THIS HOME
Winding Cypress, FL Homes for Sale
Situated on the water, this 1Br/2Ba home is affordable and a location where you OWN YOUR OWN LAND when you purchase your home in NAPLES, FLORIDA! It is positioned within Imperial Wilderness Condominium Association, a gated 55+ community that was never flooded! In 2025, new plank flooring was installed throughout the entire home. The refrigerator was replaced in 2023 and the A/C in 2022. This home boasts updated exterior features (roof, siding, pavers, sea wall, & mini yard — all in 2017 & 2018). The rear of the home faces south. Plus, you’ll appreciate the high ceilings and under-the-house storage space. On top of all of these attributes, the community is located appr

$174,000

1 bed2 baths960 sq ft

561 Cattleya Refuge #561, Naples, FL 34114

Gated community • Never flooded • High ceilings

Property at 9093 Capistrano St S #7501, Naples, FL 34113, 2 beds, 2.5 baths

$375,000

2 beds2.5 baths1,487 sq ft

9093 Capistrano St S #7501, Naples, FL 34113

Property at 1220 Enbrook Loop, Naples, FL 34114, 2 beds, 2 baths

$469,900

2 beds2 baths1,503 sq ft

1220 Enbrook Loop, Naples, FL 34114

Property at 14727 Nautilus Pl, Naples, FL 34114, 4 beds, 3 baths

$925,000

4 beds3 baths2,350 sq ft

14727 Nautilus Pl, Naples, FL 34114

Property at 206 Cheetah Dr #206, Naples, FL 34114, 1 bed, 1.5 baths

$129,000

1 bed1.5 baths840 sq ft

206 Cheetah Dr #206, Naples, FL 34114

Property at 558 Cattleya Refuge #558, Naples, FL 34114, 2 beds, 2 baths

$230,000

2 beds2 baths960 sq ft

558 Cattleya Refuge #558, Naples, FL 34114

Property at 8181 Xenia Ln, Naples, FL 34114, 2 beds, 2 baths

$539,900

2 beds2 baths1,540 sq ft

8181 Xenia Ln, Naples, FL 34114

Property at 8957 Malibu St #502, Naples, FL 34113, 2 beds, 2.5 baths

$389,000

2 beds2.5 baths1,531 sq ft

8957 Malibu St #502, Naples, FL 34113

Property at 6750 Beach Resort Dr #10, Naples, FL 34114, 2 beds, 2 baths

$379,900

2 beds2 baths1,351 sq ft

6750 Beach Resort Dr #10, Naples, FL 34114

Property at 11 Zircon Dr, Naples, FL 34114, 1 bed, 1 bath

$68,500

1 bed1 bath406 sq ft

11 Zircon Dr, Naples, FL 34114

Property at 11 Zircon Dr Unit 11-Z, Naples, FL 34114, 1 bed, 1 bath

$68,500

1 bed1 bath406 sq ft

11 Zircon Dr Unit 11-Z, Naples, FL 34114

Property at 14095 Winchester Ct #603, Naples, FL 34114, 3 beds, 2.5 baths

$359,000

3 beds2.5 baths1,507 sq ft

14095 Winchester Ct #603, Naples, FL 34114

Property at 554 Cattleya Refuge #554, Naples, FL 34114, 2 beds, 2 baths

$235,000

2 beds2 baths960 sq ft

554 Cattleya Refuge #554, Naples, FL 34114

Property at 13431 Snook Cir, Naples, FL 34114

$550,000

Land3,049 sq ft (lot)

13431 Snook Cir, Naples, FL 34114

Property at 351 Bobcat Run, Naples, FL 34114

$115,000

Land3,484 sq ft (lot)

351 Bobcat Run, Naples, FL 34114

Average home prices near Winding Cypress, FL

Cities

Neighborhoods
Zip Codes

Winding Cypress homes for sale
$1,032,500
Naples Reserve Golf Club homes for sale
$925,000
Naples Reserve homes for sale
$925,000
Falling Waters Beach Resort homes for sale
$388,750
Fiddler's Creek homes for sale
$735,000
Royal Fakapalm homes for sale
$660,000
South Naples homes for sale
$419,450

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)

$802,118

-7.5% YoY | Sep 2026

1 year
3 year
5 year

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

Location

Data

Sep 2026

Growth

% YoY

Winding Cypress, FL

$802,118

-7.5%

See more Winding Cypress, FL market insights

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