Sands REPM

7759 Winding Cypress DR photos

Stately curb appeal featuring a 3 car extended garage, mature landscaping,  tile roof, stucco exterior, and a paved driveway
Aerial perspective highlighting the property's prime waterfront location
Two-story foyer featuring double entry doors, natural light , wood tile flooring, a carpeted staircase, and built-in shelving with glass accents
Guest Bedroom #1  featuring a vibrant accent wall, tile flooring, windows with white plantation shutters
Spacious interior great room  featuring a tiered tray ceiling with a ceiling fan, recessed lighting, and light tile flooring, great space to entertain
Open-concept living space featuring high tray ceilings, wood tile flooring, a contemporary ceiling fan, recessed lighting, and a kitchen with white cabinetry and upgraded  stainless steel appliances
Spacious kitchen with a large central island, under cabinet lighting, walk in pantry, stainless steel appliances, white cabinetry, additional bar area
Spacious kitchen featuring an extended center island with integrated dual sink, white cabinetry with plenty of storage, and neutral tile backsplash
Contemporary kitchen featuring white shaker cabinetry, quartz countertops, a mosaic tile backsplash, recessed lighting, and wood-tile flooring
Bright breakfast area with beautiful views of the outdoor living  space and sunrise lake views
Flex space to use as a den, home office, craft room, play room or additional TV room your choice
Spacious primary bedroom featuring light tile  flooring, tray ceiling with a ceiling fan and sitting area
Spacious primary bathroom featuring a dual vanity with white cabinetry and light countertops, and an expansive tiled shower with a glass enclosure, large walk in closet
Expansive vanity with dual undermount sinks, white cabinetry, private water closet and double doors into your spacious walk in closet
Laundry room with large sink and storage cabinets,  drop zone near rear garage entrance
Guest bedroom  #2 featuring light tile flooring, complete with pocket door to make ensuite for guest privacy
Bathroom #2 featuring a white vanity with tub and shower
Spacious interior dining room area featuring light tile flooring, recessed lighting, and staircase leading to additional living space
Spacious living area to make your own
Media Room, Guest or extended family area, kid zone, billiards or card room you decide.
VIRTUAL STAGED - bonus room featuring recessed lighting, a ceiling fan, a built-in bar with cabinetry and a beverage cooler, and carpet flooring
Guest Bedroom 3 - upper level - with adjoining full bathroom.
Bathroom #3- upper level full bathroom
Screened outdoor pool with  integrated spa,  wide unobstructed water and preserve views for your enjoyment
Screened outdoor swimming pool with an integrated spa, set on a paver patio with private lake views
Screened lanai featuring a swimming pool, integrated spa, and illuminated patio pavers bordering a lake
Sunset views from the pool area
Sunset from the enclosed pool area and covered outdoor kitchen/ dining  area, all overlooking a tranquil body of water
7759 Winding Cypress DR photo 29
Front exterior featuring a 3 car extended garage, mature landscaping, and an illuminated entryway
Waterfront property with expansive serene water reflections at sunset
Rear covered lanai  patio featuring a built-in outdoor kitchen with storage closet and pool bath
Pool bath and storage closet
Covered patio featuring  electric storm shades to completely enclose area
Evening view of spacious covered lanai
Waterfront property featuring a screened-in swimming pool and private lanai
Aerial view showcasing a property with a distinct roofline, a screened pool enclosure, and lush surrounding landscaping
Aerial community overview with a central residential street
Waterfront and preserve views
Aerial perspective showcasing the private location with wonderful views
Aerial location at the end of the community
Winding Cypress Entry
7759 Winding Cypress DR photo 43
Covered outdoor community area featuring a stone accent wall with a fireplace
Community Resort-style pool with residents only on site restaurant
Bocce ball courts fun for all
Multiple pickleball courts
Tennis courts
Fitness center featuring multiple workout machines
Nature boardwalk to enjoy a walk
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7759 Winding Cypress DR, NAPLES

Single Family Residence

Active

$1,400,000

4

Beds

5

Baths

3,464

Sqft

Est. $7,951/mo · Get pre-qualified

Home Type: Single Family ResidenceYear Built: 2020Sqft: 3,464Price/Sqft: $404Lot Size: 0.23 acresHOA: $1,646 / quarterly

Welcome to one of the most prestigious, stately, and expansive offerings throughout the entire, always-desirable community of Winding Cypress. This exclusive Stonewater Model, with a full 2nd floor of living space, is a DiVosta Builder's flagship luxury home and a very rare find. This property sits on the most exceptional 1/4 acre lot with a spectacular large lake view and full preserve backdrop across the water. Quiet, serene privacy is what you should expect all day long, especially as you witness the incredible early morning sunrises. As soon as you enter the home's grand 2 story foyer via the front double doors, you can't help but notice the opulent main gathering area highlighted by soaring 13 foot ceilings with stylish tray surrounds. With luxury detail, convenience features, and ownership peace of mind everywhere you look, this property has it all. The waterfront, 4+ bedroom, 4 1/2 bath, and 3 car garage with 4 foot extension residence is loaded with custom upgrades. Builder and owner added features include: HURRICANE RESISTANT/IMPACT WINDOWS DOORS & SLIDERS, WHOLE HOUSE GENERATOR, HEATED BUILT-IN POOL W/INTEGRAL SPA, CUSTOM KITCHEN CABINETS W/ABOVE & UNDER CABINET LIGHTING, QUARTZ COUNTERTOPS, UPGRADED APPLIANCE PACKAGE, WALK-IN PANTRY, UPGRADED LANAI W/PICTURE WINDOW SCREEN, HURRICANE RESISTANT ELECTRIC SHADES, POOL BATH, POOL STORAGE ROOM & SUMMER KITCHEN, CUSTOM PLANK TILE THROUGHOUT ENTIRE 1ST FLOOR, EXPANSIVE OWNER'S SUITE W/SITTING AREA, TRAY CEILING, FRENCH DOORS TO HUGE OWNER'S BATH W/DUAL VANITY, EXTENDED WALK-IN SHOWER, MAKEUP VANITY, LARGE WALK-IN CLOSET, BREAKFAST AREA W/CABINETS & BEVERAGE COOLER, DESIREABLE OPEN FIRST FLOOR GATHERING SPACE W/SPECTACULAR HIGH CEILINGS ENCOMPASSING GREAT ROOM, DINING AREA, KITCHEN & BREAKFAST NOOK, GLASS WALL OF DOUBLE SLIDERS THAT OPENS OUT TO LANAI & OUTDOOR LIVING SPACE, UPGRADED LIGHTING AND PLUMBING FIXTURES, 2 OTHER DOWNSTAIRS BEDROOMS CONVERT TO ENSUITES, LAUNDRY CENTER W/CABINETS & CUSTOM TUB, EXPANSIVE 2ND FLOOR LIVING SPACE INCLUDING THE 4TH BEDROOM & FULL BATHROOM, HUGE THEATER/MEDIA ROOM SPACE W/ ADDITIONAL SITTING AREA & WALK-IN CLOSET, BONUS ADDED DEN/OFFICE W/FRENCH DOORS, DUAL ZONED COOLING/HEATING W/2 HVAC UNITS, DESIRABLE 3 CAR EXTENDED GARAGE WITH RUBBER TILE FLOORING & 6 CEILING MOUNTED STORAGE RACKS. Winding Cypress is a most sought after, newer gated community renowned for it's amazing amenities at a great value. Of the total 1250 acres making up the community, Winding Cypress boasts over 825 acres of green space, mature landscape, lakes and preserve. Conveniently located just 15 minutes to downtown Olde Naples, 10 minutes to Marco Island, and 10 minutes to I75, you are close to the best beaches, dining, and boutique shopping that Southwest Florida has to offer.

40 days on market · Listing updated August 25, 2026

Location

Facts & Features

Interior Features:
Split Bedrooms, Great Room, Den - Study, Media Room, Built-In Cabinets, Wired for Data, Cathedral Ceiling(s), Closet Cabinets, Coffered Ceiling(s), Entrance Foyer, Pantry, Tray Ceiling(s), Volume Ceiling, Walk-In Closet(s)
Appliances:
Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Microwave, Range, Refrigerator/Icemaker, Self Cleaning Oven, Wall Oven, Washer
Flooring:
Carpet, Tile
Laundry:
Inside, Sink
Primary Bedroom:
Master BR Sitting Area
Primary Bathroom:
Dual Sinks, Shower Only
Kitchen:
Kitchen Island, Walk-In Pantry
Dining Room:
Dining - Family, Eat-in Kitchen
Heating:
Central Electric, Zoned
Cooling:
Ceiling Fan(s), Central Electric, Zoned
Gas:
Natural
Utilities:
Underground Utilities, Natural Gas Connected, Cable Available
Sewer:
Central
Water Source:
Central
Security:
Smoke Detector(s), Smoke Detectors
Exterior Features:
Gas Grill, Outdoor Kitchen, Sprinkler Auto
Construction:
Concrete Block, Stucco
Roof:
Tile
Patio / Porch:
Screened Lanai/Porch
View:
Lake, Preserve, Trees/Woods
Waterfront:
Lake Front, Pond
Direction Faces:
Southwest
Lot Features:
Cul-De-Sac
Irrigation:
Central
Road Surface:
Paved
Road Frontage:
Private Road
Parking:
Driveway Paved, Garage Door Opener, Attached
Garage Spaces:
3
Pool:
Community Lap Pool, In Ground, Concrete, Equipment Stays, Gas Heat, Pool Bath
Windows:
Impact Resistant, Single Hung, Impact Resistant Windows, Shutters - Screens/Fabric, Window Coverings
Doors:
Impact Resistant Doors
Community Features:
Bocce Court, Cabana, Clubhouse, Pool, Community Room, Dog Park, Fitness Center Attended, Internet Access, Library, Pickleball, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
Subdivision:
WINDING CYPRESS
Annual Taxes:
$10,830
Pets Allowed:
Number Limit
Furnished:
Negotiable
Possession:
Close Of Escrow
Listing Terms:
Buyer Finance/Cash
Disclosures:
Seller Disclosure Available

Price History

DateEventPrice
Jul 20, 2026Original list price$1,400,000

Reflects listing data on file, not a complete transaction history.

Listed by Theresa Bocka, William Raveis Real Estate

Co-listed by Paul Bocka, William Raveis Real Estate

$1,400,000

7759 Winding Cypress DR, NAPLES

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$7,951

est. monthly payment

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The data relating to real estate for sale displayed on this Website comes in part from the Multiple Listing Service of the Bonita Springs-Estero Association of REALTORS®, Inc., under License No. BK3468074. Properties displayed on this Website include properties listed with brokerage firms other than Sands Real Estate & Property Management. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Bonita Springs-Estero Association of REALTORS® Multiple Listing Service, or contained in the database compilation of the Bonita Springs-Estero Association of REALTORS® Multiple Listing Service.