Winding Cypress Real Estate &amp; Homes

3 Beds ⋅ 2 Baths ⋅ 2026015957 MLS

$725,000

Welcome to your beautiful Summerwood floor plan home ... Enjoy Florida living in this IMPECCABLY maintained STUNNING home featuring 3 bedrooms, den/sitting room, 2 full bathrooms. Enjoy a spacious living room which is open to the gourmet kitchen featuring a NATURAL GAS range, a large pantry and an island, with ample prep space, for gathering with friends and family. There is tile flooring throughout! Step outside to the a very sought after outdoor living life with the EXTENDED LANAI!! On the Lanai is a built in kitchen for all of your entertaining needs! The home has a FULL HOUSE GENERATOR & IMPACT RESISTENCE WINDOWS. The window and sliding door to the Lanai are storm protected with a STORM SMART SCREEN!! The primary suite is a private retreat with a walk-in closet, dual-sink vanity, and a large step in with glass shower. The dining room offers tranquil views of the expansive lanai. A 2 car garage has a huge extra space for storage. The brick-paver driveway provides ample parking. Set on a beautiful homesite, this residence blends privacy with proximity to the best of South Naples. The subdivision hosts an amazing club, with all residents enjoying access to the community’s restaurant, resort style pool, exercise room/gym, tennis, bocce, and pickleball courts. Experience unparalleled luxury, comfort, and location here, an absolute must-see!

7022 Live Oak DR, Naples

Courtesy of John R. Wood Properties.

$1,025,000

4 Beds ⋅ 2 Baths ⋅ 226013964 MLS

This beautifully designed and impeccably maintained home offers the perfect blend of elegance and comfortable Naples living. Featuring the highly sought-after Summerwood floor plan with a spacious Great Room extension, the open layout creates an impressive, light-filled space perfect for entertaining guests or relaxing with family after a day exploring beautiful Naples, FL. The gourmet kitchen shines with upgraded stainless appliances, elegant quartz countertops, an oversized island perfect for casual dining and hosting, and a generous walk-in pantry. This home features a generous primary Master bedroom plus three versatile guest bedrooms. Any of the three guest bedrooms can easily function as a bedroom, home office, den, or media room to suit your lifestyle. The fourth bedroom is a major advantage for leasing the home, providing extra flexibility that can help attract tenants, support higher rental rates, and appeal to a wider range of renters who need extra space for guests, etc. It also functions well as internal storage space or could be used to expand the Master closet. Interior finishes include high-grade porcelain tile flooring throughout, a practical laundry/utility room with storage and sink. And natural gas service is used for cooking, water heating, and efficient clothes drying. Step outside to your private resort-style lanai. This expansive space features custom pavers, a built-in outdoor kitchen, and plenty of room for outdoor gatherings or quiet relaxation. Enjoy a swim in the heated pool and spa, soak up the southern Florida sunshine, or simply take in the spectacular eastern water views framed by a large portrait “no-see” lanai screen. These serene vistas consistently draw “wows” from everyone who visits. For added peace of mind and year-round comfort, the home includes impact-resistant hurricane doors and windows throughout. These premium features provide excellent storm protection, improve energy efficiency, and help reduce insurance premiums while eliminating the hassle of traditional shutters. Elegant Bahama shutters offer additional beauty and protection. The elevated lot is also not in a mandatory flood insurance zone, adding to the worry-free lifestyle. Nestled in the prestigious gated community of Winding Cypress, residents enjoy an onsite restaurant, modern fitness center, community pool, tennis courts, pickleball courts, and a full calendar of social events—all just a walk, bike, or golf cart ride away. Conveniently located between downtown Naples and Marco Island, you’re minutes from pristine beaches, upscale shopping, and fine dining. Offered fully furnished and move-in ready, this exceptional home truly checks every box: Impressive Great Room. (Check.) Gourmet kitchen & flexible living spaces. (Check.) Resort-style outdoor living with water views. (Check.) Outstanding community & prime location. (Check.) Ready for the Naples lifestyle you’ve dreamed of? This beautiful home delivers it all.

7631 Winding Cypress DR, Naples

Courtesy of Premiere Plus Realty Company.

2 Beds ⋅ 2 Baths ⋅ 226008984 MLS

$550,000

The one and only Cressida Villa plan with the unique front entrance and foyer layout in Winding Cypress with an expanded lanai and a sweeping, wide-water views that feels endless. This light-filled, impeccably maintained residence showcases all quartz countertops, premium cabinetry, porcelain tile, natural gas, and seamless indoor-outdoor living designed for entertaining or quiet sunset evenings. The oversized lanai captures panoramic water views, creating a private, tranquil backdrop rarely available. Move-in ready and in amazing condition, this home stands out for its scale, upgrades and setting. In the resort community of Winding Cypress, a low-fee, resort-style guard-gated community with 800 acres of preserve, full-time activities director, resort and lap pool, on-site restaurant, fitness center, pickleball and tennis courts, and miles of recreational, biking and nature trails.

7785 Jacaranda LN, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Diamond Key Real Estate.

$905,000

2 Beds ⋅ 2 Baths ⋅ 226009304 MLS

Experience refined Naples living in this impeccably maintained, fully furnished residence in the prestigious gated community of Winding Cypress. Featuring two bedrooms plus a den, two baths, plus an extended additional den leading to the waterfront pool area, and an extended 2-car garage; this home has been thoughtfully designed and is move-in ready - blending comfort, elegance, and effortless luxury. Inside, tiled wood-plank flooring flows seamlessly throughout, complemented by plantation shutters throughout the home that add both timeless elegance and privacy. The beautifully curated furnishings enhance each space, delivering a polished, designer feel from the moment you enter. The gourmet kitchen serves as the heart of the home, featuring a large center island with seating, a pantry closet, gas stove, and abundant cabinetry. Ideal for both everyday living and entertaining, the kitchen opens to the spacious dining and living areas, allowing for easy gatherings and relaxed conversation. The versatile den provides the perfect setting for a private office, media room, or additional guest accommodations. The primary suite is a luxurious retreat, complete with a spa-inspired bath and a recently customized walk-in closet designed for optimal organization and style. The guest bedroom and bath provide comfort and privacy for visitors. Step outside to your private oasis—a covered lanai with comfortable seating that transitions seamlessly to the screened-in pool and spa area. The expansive pavered deck surrounds a sparkling pool and spa accented by a tranquil waterfall feature, all overlooking a peaceful lake view. Storm Smart lanai shutters offer added protection and convenience, while upgraded landscaping and lanai lighting create a stunning ambiance day and night. The beautifully landscaped lawn enhances the serene setting, delivering exceptional curb appeal and a tranquil outdoor backdrop. An underground gas generator provides an additional layer of security and peace of mind, ensuring uninterrupted comfort year-round. Winding Cypress elevates the lifestyle even further with an impressive array of resort-style amenities. Residents enjoy a stunning clubhouse, state-of-the-art fitness center, resort-style pool and spa, tennis and pickleball courts, bocce, an on-site restaurant, community garden, dog park, and miles of scenic walking and biking trails. A vibrant social calendar and beautifully maintained grounds make every day feel like a private resort experience. Ideally situated just minutes from the world-class dining, upscale shopping, art galleries, and white-sand beaches of downtown Naples, this home offers the perfect combination of luxury, location, and lifestyle. An exceptional opportunity to own a furnished, lakefront retreat in one of Naples’ most sought-after communities.

7545 Geranium WAY, Naples

Courtesy of Coldwell Banker Realty.

Selling Office: Coldwell Banker Realty.

$635,000

2 Beds ⋅ 2 Baths ⋅ 226009024 MLS

This gorgeous Serenity villa features 2 bedrooms, a den, a pool, and a 2-car garage, and is being offered turnkey furnished. The pool deck showcases one of the best lake views in the community, complete with spectacular sunsets, a picture-window screen, a spacious covered lanai, and a pool heated by both electric and solar—helping keep energy costs down. Enjoy peace of mind with impact windows and doors throughout, a whole-home generator, and a hurricane screen for added lanai protection. Inside, the home is loaded with upgrades, including plantation shutters, under-cabinet lighting, a tray ceiling, custom shelving in the living room and den, and more. Winding Cypress is a natural gas community with resort-style amenities. Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

7717 Jacaranda LN, Naples

Courtesy of Realty One Group MVP.

2 Beds ⋅ 2 Baths ⋅ 226008768 MLS

Experience elevated resort-style living in the highly desirable community of Winding Cypress. This impeccably maintained and tastefully updated 2-bedroom plus den, 2-bath villa offers soaring 9’4” ceilings and an attached two-car garage, delivering both comfort and functionality in a truly move-in-ready residence. Thoughtful upgrades include a newer refrigerator and hot water heater, upgraded pavers, plantation shutters, and additional enhancements that add both style and peace of mind. The flexible den provides the perfect space for a home office, guest retreat, or additional lounge area. Winding Cypress is designed for those who value lifestyle. Nearly two-thirds of the community is preserved as tranquil natural landscape and wooded conservation, creating a serene, private atmosphere rarely found this close to everything. Ideally located just 8 miles from Downtown Naples and 9 miles from Marco Island, you are moments from world-class dining, shopping, and Gulf beaches. Residents enjoy an impressive amenity package featuring pickleball, bocce, clubhouse, resort-style pool and spa, community park, social rooms, and more. Opportunities like this are rare. Schedule your private showing today.

7666 Jacaranda LN, Naples

Courtesy of EXP Realty LLC.

$834,999

3 Beds ⋅ 2 Baths ⋅ 226007913 MLS

Paradise at your fingertips. This modern three-bedroom plus den residence in the prestigious resort style living gated community of Winding Cypress, offers a bright, expansive open floor plan, breathtaking lake views, ceramic tile throughout and a gorgeous and functional updated kitchen featuring solid maple shaker cabinetry, premium hardware, and spacious pantry. This residence is also equipped with gas stove, brand new LG Studio refrigerator and stove to enjoy a fabulous culinary experience. The magnificent quartz island, ideal to entertain and savor your favor meals is illuminated by one of a kind showstopper custom abalone shell chandelier which mirrors the one in the dining room creating a one of kind ambiance. The large family room flows harmoniously to an inviting bar area to taste your favorite drink. The Master bedroom provides high ceilings, custom made cabinetry and serene lake views. Both bathrooms feature Aquadome LED fog-free mirrored medicine cabinets adding a touch of functionality and elegance. Life al fresco is enjoyed to the fullest in the spectacular extended back patio, with outdoor kitchen and several sitting areas. This enclosed lanai with panoramic premium screens allows for breathtaking unobstructed water and sky views. Also available is an initial electrical connection to install a jacuzzi if desired. Ample storage and full hurricane protection plus generator to provide extra peace of mind. Additional traits are the Wakaflex installed on all vents, openings and roof crown for maximum weather protection, the Eufy home security system, recently painted inside and out, Maytag Washer and Dryer, Culligan reverse osmosis water filter, front entry screened enclosure and driveway expanded to accommodate 3 vehicles. The 2-car garage comes with overhead storage. Winding Cypress offers world-class amenities, including a clubhouse, on-site restaurant, fitness center, resort pool, and tennis/pickleball courts. Positioned between the sun-drenched beaches of Marco Island and upscale dining, shops and galleries of downtown Naples, this home offers the ultimate setting for relaxation, comfortable living and sophisticated entertaining.

7460 Blackberry DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

$565,000

2 Beds ⋅ 2 Baths ⋅ 226006913 MLS

Discover effortless luxury in this lovely villa—your private oasis in a premier gated Naples community, Winding Cypress. This inviting 2-bedroom + den, 2-bath home delivers exceptional comfort and versatility with a bright, open layout designed for effortless living and entertaining. Step into the expansive Great Room with high ceilings, creating an open, airy vibe—perfect for gathering with friends or unwinding after a day out in Naples. The chef's kitchen impresses with premium quartz countertops, solid wood soft-close cabinets, and natural gas cooking. High-traffic porcelain tile flooring flows seamlessly throughout the entire villa, paired with smooth-finish walls for a clean, modern, low-maintenance aesthetic. The flexible den, enclosed by beautiful glass panel doors, adapts effortlessly as a home office or third bedroom. Both bedrooms feature generous walk-in closets, and the bathrooms showcase floor-to-ceiling porcelain tile, glass showers, and spa-like sophistication. The master bath elevates your routine with a dramatic full-wall custom mirror and elegant drop-down designer lighting. Outside, this premium lot offers generous spacing between villas and captivating views over the community's second-largest lake—where serene water vistas create an unparalleled sense of tranquility and timeless appeal. The west-facing orientation captures breathtaking sunsets reflecting off the shimmering waters, while the south-facing exposure floods the interior with natural light. Plenty of space awaits an extended lanai or private pool, all enhanced by the soothing backdrop of the lake. Built for peace of mind: impact windows and doors boost energy efficiency, reduce noise, and lower insurance premiums—no flood insurance required in FEMA Zone X. Appliances, A/C, and water heater have performed flawlessly since new. Fiber optic connectivity ensures ultra-fast internet and seamless 4K streaming. Natural gas powers cooking, drying, hot water, and preps for a whole-home generator. Nestled in gated Winding Cypress—praised as Naples' best lifestyle value with remarkably low HOA fees that cover comprehensive maintenance (lawn care, irrigation, community upkeep) plus full access to extensive high-end amenities—you'll embrace the pet-friendly lifestyle with two dedicated dog parks, miles of scenic walking/biking trails across 800+ acres of preserved natural land, and a vibrant social calendar with events curated by the on-site activities director. Resort-style perks include the on-site Shady Palm Café for casual dining and drinks, state-of-the-art fitness center with movement/yoga room, sparkling resort pool and spa, lighted tennis and pickleball courts, bocce courts, community garden, fire pit, and more—all accessible by foot, bike, or golf cart. Conveniently located between downtown Naples and Marco Island, you're minutes from pristine beaches, upscale shopping, and fine dining. Paradise is calling.

7733 Jacaranda LN, Naples

Courtesy of Premiere Plus Realty Company.

2 Beds ⋅ 2 Baths ⋅ 226006762 MLS

$580,000

Nestled within the gated, amenity-rich community of Winding Cypress, this thoughtfully designed turnkey furnished two-bedroom plus den, two-bath residence offers an exceptional blend of comfort, quality, and relaxed Florida living. The open floor plan is enhanced by wood flooring throughout the main living areas, along with crown molding, and a distinctive coffered ceiling in the living and dining area, creating a refined yet inviting atmosphere. The kitchen is both elegant and functional, featuring 42" white cabinetry, granite countertops, tile backsplash, undercabinet lighting, and stainless-steel appliances—ideal for everyday living and entertaining alike. A flexible den with French doors provides the option for a private home office, media room, or additional guest space. Seamless indoor-outdoor living is achieved through the expansive custom lanai, designed for entertaining with an outdoor kitchen complete with gas grill, refrigerator, and sink, an above-ground HotSprings hot tub with beautiful outdoor furnishings including a dining table for six, over-sized parasol umbrellas that provide shade, and picture-frame lanai screens that showcase peaceful preserve surroundings. Additional highlights include a whole-house gas generator, two-car garage, and plantation shutters. Winding Cypress is a natural gas community thoughtfully designed around preserved natural beauty and an active, social lifestyle. At its heart is an impressive clubhouse with a heated resort-style pool and spa, poolside dining at The Shady Palm, state-of-the-art fitness center, library, and community gathering rooms. Other amenities include pickleball and tennis courts, bocce courts, dog parks, a community garden, and scenic walking and nature trails. Known for its welcoming atmosphere and beautifully maintained grounds, Winding Cypress offers a true sense of community while remaining conveniently close to everything Naples has to offer. A six-passenger well-maintained golf cart is included for effortless access throughout the neighborhood.

7121 Live Oak DR, Naples

Courtesy of John R Wood Properties.

Selling Office: John R Wood Properties.

$949,900

3 Beds ⋅ 2 Baths ⋅ 226005365 MLS

Welcome to newest and last phase of homes built in 2020 in the vibrant well maintained community of Winding Cypress. Located just off Collier and 41 and minutes to 75 , Marco Island and downtown Naples This summer wood model is sure to please with 3 bdrms den and 2 baths with full showers , primary bath with custom mirrors. custom closet , plantation shutters mini a/c in garage, whole house water purifier, generator, storm screens on lanai ,outdoor kitchen , pool and spa. with private views to the preserve ,vaulted ceilings, ceiling fans in every room , and oversized neutral tile through out placed on the diagonal . some furniture can remain with the house . exlcuded dining light fixture

6844 Winding Cypress DR, Naples

Courtesy of Royal Shell Real Estate, Inc..

$460,000

2 Beds ⋅ 2 Baths ⋅ 226005810 MLS

This property is nestled in one of Naples’ most desirable communities. This home features two spacious bedrooms, two elegant baths, and a flexible den—perfect for a home office, hobby room or additional guest area. The upgraded kitchen is equipped with stainless steel appliances, quartz counter tops in kitchen and both bathrooms, and bright 42” cabinetry with under lighting, creating an inviting space for entertaining. Enjoy the open-concept living and dining area with stylish tile flooring on the diagonal throughout, plantation shutters on all windows, and 2 interior pocket doors that provide privacy to the owners and guest suite areas. The sliding doors lead to a private covered screened lanai ideal for relaxing or dining outdoors. A large rear lot where you can design your own pool area if so desired. This property provides ample space for both relaxation and functionality as a vacation home or easy full-time Florida living.

7658 Jacaranda LN, Naples

Courtesy of William Raveis Real Estate.

Selling Office: Waterfront Realty Group Inc.

$615,000

2 Beds ⋅ 2 Baths ⋅ 226005934 MLS

Sunset water views stretch across a sparkling long lake from your private pool and spa, creating a breathtaking backdrop for everyday living and entertaining from the fully equipped natural gas outdoor kitchen. This beautifully maintained home stands out with major recent upgrades including a brand new AC system (2026), new washer and dryer, new hot water heater, and new carpet, offering peace of mind and allowing the home to live comfortably and effortlessly from day one. The open floor plan feels light, bright, and inviting with updated flooring and elegant quartz and granite surfaces throughout. The thoughtfully designed layout offers two spacious bedrooms plus a flexible den with an alcove ideal for adding a closet, making it perfect for guests, a home office, or additional sleeping space. The gourmet kitchen blends style and function with granite countertops, a tasteful tiled backsplash, staggered cabinetry, and bar seating for casual gatherings, while natural gas service and ceiling-mounted garage storage racks add everyday convenience. Gently lived in as a pet-free, smoke-free seasonal residence, the property shows like new. Located in the resort-style community of Winding Cypress, residents enjoy more than 800 acres of preserved natural landscape and exceptional amenities including a clubhouse with a heated pool, on-site restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park, and scenic nature trails, all with low HOA fees and an ideal location just 25 minutes to Fifth Avenue South, 20 minutes to Marco Island, and minutes to major shopping and dining, creating a lifestyle that blends luxury, convenience, and unforgettable views.

7639 Jacaranda LN, Naples

Courtesy of Premier Sotheby's Int'l Realty.

3 Beds ⋅ 3 Baths ⋅ 226004334 MLS

$800,000

This gorgeous Mystique floor plan features 3 bedrooms, a den, a rare 3 full bathrooms, heated pool, and a 2-car garage. Inside the home is loaded with upgrades, impact windows and doors, custom built-in cabinetry in the living & laundry room, crown molding, tray ceilings, recessed lighting, electric blinds, designer hardware and lighting, and abundant storage throughout. Embrace the Florida lifestyle with the open-concept zero-corner slider connecting the indoor and outdoor living spaces. The pool deck offers a spacious covered lanai, a modern pool, added privacy, and highly desirable southwest exposure. No detail has been spared in the garage, which features a built-in workbench and storage, an electric screen garage door, epoxy flooring, and plenty of room for bikes and more. Winding Cypress is a natural gas community with resort-style amenities. Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even two dog parks for your furry friends. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

6754 Pennyroyal DR, Naples

Courtesy of Realty One Group MVP.

Selling Office: LPT Realty, LLC.

$599,900

2 Beds ⋅ 2 Baths ⋅ 226002887 MLS

This home has just been freshly painted inside and out. professionally painted kitchen and bath cabinets, nice private south waterview , screened lanai able to enlarge or expand with a pool. Previous owner had a great workshop in garage with 8 overhead lights, addition dual media cat5/rg6 charging station for a Tesla , framed peg boards for hanging tools , custom storage cabinets and a pull down staircase for added storage. Home features 2 bedrooms 2 baths plus den a whole house generator and attached manual and electric storm shutters. Remaining furniture in home is staying. Live Oak is a beautiful mature tree lined street on cul de sac and just a short walk to the amenity center, dog park or community garden .Rarely will you find a single family home at this price in Winding Cypress . Great Value ! Winding Cypress amenity center offers so much within its gates, its own Shady Palm restaurant, resort pool , gym , bocci and pickleball courts, dog park , walking trails and so much more. Winding Cypress is a gated community located just mins to 75, downtown and Marco Island. Photos to be uploaded on 1/24

7255 Live Oak DR, Naples

Courtesy of Royal Shell Real Estate, Inc..

Selling Office: Royal Shell Real Estate, Inc..

$520,000

3 Beds ⋅ 2 Baths ⋅ 226000537 MLS

Welcome to effortless, refined living in the highly desirable Winding Cypress community. Set on the largest homesite in the neighborhood, this impeccably upgraded 3-bedroom, 2-bath villa offers exceptional privacy, expansive outdoor space, and a true lock-and-leave lifestyle. Furnishings are negotiable, making this a flexible opportunity for both full-time and seasonal residents. Designed for relaxed everyday living and easy entertaining, the open floor plan feels light, inviting, and polished without being formal. Thoughtful designer touches throughout create a warm, comfortable atmosphere that flows naturally from indoors to outdoors. The extended screened lanai becomes an everyday retreat, ideal for morning coffee, sunset unwinding, or hosting friends, while the outdoor summer kitchen makes casual gatherings effortless. Peace of mind is a defining feature of this home, with over $100,000 in safety and security upgrades already in place. A whole-house backup generator, advanced security system, hurricane protection, and smart access features allow you to travel or entertain with confidence, knowing everything is covered. Living in Winding Cypress means enjoying a resort-style lifestyle every day. Residents have access to a beautifully appointed clubhouse with on-site dining, resort and lap pools, a jacuzzi, fitness center, tennis, pickleball, bocce courts, and a dog park. The community is surrounded by natural preserves and lakes, creating a serene setting while remaining minutes from shopping, dining, and daily conveniences. This is a rare opportunity to own a premier villa in one of Southeast Naples’ most sought-after gated communities. Priced competitively and offering flexibility on furnishings, this home delivers comfort, security, and lifestyle in one exceptional package.

7176 Live Oak DR, Naples

Courtesy of John R Wood Properties. 239-784-2831

3 Beds ⋅ 2 Baths ⋅ 226000187 MLS

$910,000

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 indoor and outdoor living spaces. The pool deck features a spacious covered lanai overlooking the lake with a highly desirable southwest exposure, along with an outdoor kitchen and a custom saltwater pool and spa complete with a sun ledge. No detail has been spared in the garage as well, it features a mini split, insulated door, and an extra 4 feet of length, allowing room for tools, bikes and more! Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

6779 Winding Cypress DR, Naples

Courtesy of Realty One Group MVP.

3 Beds ⋅ 3.5 Baths ⋅ 225083620 MLS

$1,150,000

This home is an amazing value for Winding Cypress!! Once you compare, you'll agree. The Stonewater model is the largest one floor living within The Community. The sought after "open area concept" footprint boasts 3 expansive bedrooms including a most impressive owner's suite, 3 full baths PLUS and additional POOL BATH , a large den-flex room with glass French doors, desirable 3 car garage with additional storage racks overhead. Upgrades include an executive waterfront and private preserve view lot, pool with integral spa.

7716 Winding Cypress DR, Naples

Courtesy of William Raveis Real Estate.

Selling Office: Realty One Group MVP.

$835,000

3 Beds ⋅ 2 Baths ⋅ 225083676 MLS

Check out 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 bathroom. Elegant details include crown molding, tray ceilings, plantation shutters, Hunter Douglas blinds, and updated flooring provides a tranquil space for relaxation or entertaining. The custom gourmet 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 screened lanai, and a large pool.

7211 Live Oak DR, Naples

Courtesy of William Raveis Real Estate.

Selling Office: RE/MAX Nautical Realty.

$890,000

3 Beds ⋅ 3 Baths ⋅ 225082316 MLS

Discover resort-style living in this rare three-bedroom plus den, three-bath natural gas home in the highly sought-after community of Winding Cypress. Designed for privacy and effortless indoor–outdoor living, it features an oversized fully custom pool with integrated seamless spa and a panoramic barless screen lanai, integrated home theater sound, all overlooking lush, tranquil landscaping. The great room opens with a dramatic zero-corner disappearing slider, and the home is nearly brand new with 2022 construction still under the renowned DiVosta builder warranty. Located on a private cul-de-sac, this home offers peaceful living while keeping you close to world-class amenities. Winding Cypress boasts private nature trails, community gardens, and an impressive 18,000-square-foot resort clubhouse with a poolside restaurant, full-time activities director, lap lanes, zero-edge resort pool with waterfall, fire pit, pickleball, tennis, and more. The community now features two grand entrances/exits on both Tamiami Trail (U.S. 41) and Collier Boulevard (951), offering exceptional convenience.

6698 Pennyroyal DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

4 Beds ⋅ 3 Baths ⋅ 225081501 MLS

$940,000

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 private bedroom, a full bathroom, and an incredible flex area that can accommodate a 5th bedroom, cinema room, office, or however this extra space can benefit your living wants and needs. Winding Cypress is an amenity rich and active community with on-site management and a full-time Activities Director. It's perfectly situated just 15 minutes away from the restaurants, shoppes, and beaches of downtown Olde Naples, and only 10 minutes to all the entertainment of Marco Island.

6825 Greenbriar CT, Naples

Courtesy of William Raveis Real Estate.

3 Beds ⋅ 2 Baths ⋅ 225079293 MLS

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 Winding Cypress means enjoying resort-style amenities without the high fees. Residents have access to an expansive resort pool with beach entry, a full-service restaurant and bar, a state-of-the-art fitness center, pickleball, tennis and bocce courts, a dog park, and miles of scenic walking and biking trails. The beautifully designed clubhouse includes a social hall, gathering spaces and a library, creating opportunities to connect and engage with neighbors. This home blends nature, privacy, comfort and community into one exceptional offering.

7167 Live Oak DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Berkshire Hathaway FL Realty.

$875,000

3 Beds ⋅ 2 Baths ⋅ 225078259 MLS

This extended Summerwood floorplan is situated on a private street 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. The open-concept layout seamlessly connects indoor and outdoor living spaces. The pool deck features a large covered lanai ideal for enjoying sunset views over the lake and preplumb of electric, gas, and water providing the option to add a built-in outdoor kitchen. Additional upgrades include tile flooring throughout, plantation shutters, trey ceiling, custom screened entryway, widened walkway & driveway and generous storage space. Turnkey furnishings are available with the sale, some exclusions. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

7355 Mockingbird CT, Naples

Courtesy of Realty One Group MVP.

Selling Office: Achieve Realty LLC.

$625,000

3 Beds ⋅ 2 Baths ⋅ 225074768 MLS

Winding Cypress – PRICE REDUCED TO SELL- Property sits approximately 2+ feet above FEMA base flood elevation. FEMA LOMA in process — flood insurance not required by lender. Rare opportunity to purchase in this community at this price point. Lowest priced 4 bedroom home in Winding Cypress. Welcome to your Florida dream home in the sought-after gated community of Winding Cypress! This immaculate residence built in 2016, offers the perfect blend of modern luxury and relaxed coastal living. Featuring 2,230’sq under air, 4 bedrooms. Two full baths, and an open-concept floor plan, this home is designed for comfort and entertaining. Step inside to find upgraded tile flooring, beautiful crown molding, a gourmet kitchen with granite countertops, stainless steel appliances, and a large center island ideal for gathering with friends and family. The spacious great room opens through sliding glass doors to a screened lanai, creating seamless indoor-outdoor living. This home also features a "sunroom" addition and an oversized garage. Enjoy peaceful views of the lush landscaping and lake—the perfect backdrop for morning coffee or sunset cocktails. The primary suite offers a spa-like bath with dual sinks, walk-in shower, and large walk-in closet. Additional features include plantation shutters, impact-resistant windows and doors, whole house water purification system, new electric hurricane screens, a "sunroom" addition not included in other floor plans, and an oversized garage and a 2-car extended garage with epoxy flooring. Located within minutes of downtown Naples and the Gulf beaches, Winding Cypress offers resort-style amenities including a lagoon-style pool, on-site restaurant, tennis, pickleball, fitness center, dog park, and miles of nature trails. Move-in ready, this is the best priced home of its size in Winding Cypress — this home combines style, value, and an unbeatable location.

7057 Live Oak DR, Naples

Courtesy of Premiere Plus Realty Company.

3 Beds ⋅ 2 Baths ⋅ 225075399 MLS

$850,000

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. All the bedrooms are large with the primary suite being expansive. This home's upgrades include a whole-house generator, a hurricane impact zero-corner sliding glass door that provides a spectacular indoor/outdoor living area combining an expansive great room to the under roof lanai dining and and separate sitting section. That's just part of the lighted lanai. There's an extended paver area for you to soak in the sun while you admire the custom pool with a soothing water feature. Looking out over the beautiful lake is made easy with the option "picture window" lanai screen. Electric StormSmart metal shutters enclose the lanai providing additional peace of mind, safety and security. Additional enhancements include a chef's kitchen layout with quartz counters, a natural gas cooktop and range, upgraded cabinets with above and under lighting, expansive island with an overhang to sit three, an upgraded backsplash and a large walk-in pantry. This home also boasts upgraded tile plank flooring, custom 8' doors throughout, high-end interior plantation shutters on all windows, an expanded laundry area with cabinets, counters, a utility sink, and extra storage. The 2 car garage has an insulated overhead door. Winding Cypress is optimally located just 15 minutes to Olde Naples, 10 minutes to both Marco Island and I75, and 30 minutes to RSW Airport. For this price point, the amenities at Winding Cypress are second to none. A resident's only full service restaurant, resort pool with spa that rivals a Las Vegas hotel, pickleball, tennis, and bocce courts, the best fitness center around, an vibrant community center with onsite management and Activities Director, a dog park, community garden, and a boardwalk nature trail are just a few of the things that make Winding Cypress so special. With only 766 single-family homes spread out over 1250 total acres that includes 850+ acres of spectacular preserve and lakes, enjoy the peace, serenity and beautiful wildlife that few communities are able to offer.

6699 Pennyroyal DR, Naples

Courtesy of William Raveis Real Estate.

3 Beds ⋅ 2 Baths ⋅ 225067825 MLS

$963,000

Rare opportunity in Winding Cypress this Marten Ray Floor Plan sits on a premium lot with unobstructed lake and protected preserve views. Experience, complete privacy and a resort-style outdoor setting in one of Naples’ most desirable communities. Experience one of the most desirable homes in Winding Cypress, offering a rare combination of premium lot, complete upgrades, and true move-in ready convenience. Perfectly situated on what is believed to be one of the only homes in the community with a full, unobstructed rear exposure, this property showcases sweeping views of a permanent lake and protected state/federal preserve, delivering exceptional privacy with no future development behind you. Designed for effortless Florida living, the home features a resort-style outdoor setting with a heated-saltwater pool, multi-color lighting, in pool and lanai, expansive lanai, dry bar with cabinetry & refrigerator, outdoor TV and audio—ideal for entertaining or relaxing in a private natural setting. Inside, the residence has been extensively upgraded beyond builder-grade, to deliver a “better than new” experience, with no projects or additional investment required. The designer kitchen includes gas cooking, enhanced cabinetry, under-cabinet lighting, and a built-in wine bar with dual-zone cooler. Additional highlights include tile flooring throughout, upgraded lighting, a high-efficiency air conditioning system, custom pantry and primary closet cabinetry, and a fully optimized garage with added storage and functionality. The flexible floor plan offers 2 additional bedrooms for versatile guest accommodations and workspace options, including a dedicated office and an additional guest space, ideal for visiting family, remote work, or multi-purpose use. This home is well suited for buyers seeking quality, privacy, and ease of ownership in one of Naples’ most sought-after communities.

7457 Winding Cypress DR, Naples

Courtesy of Gulf Coast International Prop.

Selling Office: Gulf Coast International Prop.

$595,000

2 Beds ⋅ 2 Baths ⋅ 225072028 MLS

This charming model is the perfect fit featuring an inviting open-floor concept where natural light streams through the windows. The kitchen boasts granite counters, stainless appliances and a center island and extra storage for everyday use and easy entertaining. The pantry closet has plenty of space for all of your staple goods. Tile floors are throughout much of the space. There's a den/flex room with french doors that can be used as an additional bedroom when needed or office, hobby or quiet sitting room. Additional guest bedroom and bathroom with combined tub and shower and granite topped vanity offers privacy for your family and guests. The laundry room features a spacious storage area with shelving for your all your supplies. There are storage racks in the two car garage to house your coolers for the beach. Be sure to take time to relax and enjoy your morning beverage and the beautiful sunsets on the screened lanai that overlooks the OVERSIZED lot with mature landscaping complete with an outdoor kitchen with grill, sink, and fridge for your convenience. Winding Cypress is a sought after, gated community and is appreciated for its active, social lifestyle and world class amenities. It’s nestled within 800 acres of natural preserve and 80 acres of serene lakes teeming with migratory wildlife. Head over to the clubhouse with state-of-the-art fitness center, locker rooms with showers, movement room for classes, internet café, event room, catering kitchen, resort-style pool with spa and cabanas, restaurant with bar, firepit, pickleball, tennis and bocce courts. Take the pups to play in the dog park. Walk or ride your bike on the many paths including the peaceful preserve boardwalk. If gardening is your passion, there is a community garden to grow your favorite vegetables. HOA management and friendly staff are onsite to assist and coordinate regular events for all to enjoy. Minutes from beaches, golfing, fishing, boating, shopping, and cultural activities. It's time to enjoy the Florida lifestyle!

7248 Live Oak DR, Naples

Courtesy of William Raveis Real Estate.

3 Beds ⋅ 2 Baths ⋅ 225071664 MLS

$858,500

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 raised paneled doors and a window for natural light. The main bedroom is approx 14' x 16' and sits on its own separate wing from the other bedrooms. You will love the main bathroom with its 9' x 3'3" tiled shower with multiple shower heads, dual sinks, quartz counter-tops, walk-in closet and separate toilet closet. It is very spacious! Another plus to this home is the zero corner doors off the great room extending your great room out to your covered lanai. The extended lanai is all plumbed for the outdoor kitchen of your liking. Enjoy the Florida sunshine in your pool and spa in the privacy of your own backyard which backs up to a preserve. Some of the other features of this lovely home are a 9' x 7' laundry room with cabinets, folding counters, sink, and storage closet, 2 car garage with a 4 foot extension and epoxy flooring, and impact resistant windows and sliders. The home boasts beautiful tile and light colors throughout. The white plantation shutters in many of the rooms add to the character of the home. Winding Cypress is a newer, well maintained community offering an abundance of amenities. You will find a resort-style pool and separate spa, cabanas, Shady Palm Cafe, pickleball, bocce, tennis, state-of-the-art fitness center, community garden and a dog park for your fur babies. Winding Cypress sits in a great location in Collier County, less than 30 minutes from beautiful 5th Avenue in Naples, and the white sand beaches of Marco Island. This home is a must see!

6856 Winding Cypress DR, Naples

Courtesy of Berkshire Hathaway FL Realty.

Selling Office: REMAX Affinity Mercato.

$1,495,000

4 Beds ⋅ 4 Baths ⋅ 225067265 MLS

Motivated Seller! Luxurious Lakeside Living in Winding Cypress – Rare One Owner Pinnacle Model! Welcome to this stunning lake view home offering 3,656 sq. ft. of modern elegance in the prestigious, amenity-rich community of Winding Cypress. With 4 bedrooms, 4 bathrooms, a den, bonus room, and 2,5-car garage, this home is thoughtfully designed for both everyday living and entertaining on a grand scale. Step inside to discover a light-filled open floor plan accented with tile flooring in the main living areas, brand-new luxury vinyl plank flooring in all three downstairs bedrooms, and crown molding throughout the first floor. The chef’s kitchen is a showstopper, boasting quartz countertops, premium KitchenAid stainless steel appliances, a new natural gas cooktop, soft-close cabinetry, walk-in pantry, new dishwasher, and upgraded sink—all designed for style and function. Enjoy seamless indoor-outdoor living with zero-corner sliding doors that open to an expansive lanai featuring a picture screen enclosure, heated pool and spa, and a custom outdoor kitchen with built-in hub. With southwestern exposure overlooking the long lake and preserve, sunsets here are simply unforgettable. Retreat to the primary suite with a spa-like bathroom and custom walk-in closets, while guests enjoy privacy with an en suite bedroom on the main level. Upstairs, the bonus room offers endless flexibility for a game room, theater, or additional living space. This home is equipped with hurricane-impact windows, built-in Sonos surround sound system, smart home features, and abundant storage—ensuring comfort, safety, and convenience. As a resident of Winding Cypress, you’ll enjoy world-class amenities, including:Heated resort-style & lap pools, hot tub, and gas fire pit, covered outdoor restaurant bar & grill, expansive clubhouse with fitness center, library, and event space, pickle ball, bocce, and tennis courts, miles of scenic sidewalks & boardwalk trails, two dog parks for furry family members. Perfectly positioned on a premium lot, close to the community center and surrounded by excellent local infrastructure, this home is one of the rarely available larger homes in Winding Cypress—ideal for hosting family and friends in comfort and style. Experience the best of modern Naples living in this extraordinary home.

7412 Winding Cypress DR, Naples

Courtesy of Manuela Realty.

Selling Office: Compass Florida LLC.

2 Beds ⋅ 2 Baths ⋅ 225069223 MLS

Welcome to this charming 2-bedroom plus den, 2-bath beautiful villa in the highly desirable community of Winding Cypress. Built in 2017, this residence offers 1,544 square feet of thoughtfully designed living space. The interior is light and bright, featuring easy-care tile floors in the main living areas, a breakfast bar for casual dining, and carpet in the bedrooms for added comfort. The den with French doors provides the perfect space for a home office or flex room, while the primary suite offers a private retreat with dual sinks and a walk-in shower. For added peace of mind, the home is equipped with a built-in Taexx pest control system. Step outside to your private backyard oasis, complete with a sparkling inground pool — NEW Pentair 1.5 HP SuperFlo Variable Speed pool pump installed September 2025 — perfect for relaxing or entertaining guests year-round. Winding Cypress is known for its resort-style amenities, including a large clubhouse, community pool with cabanas, fitness center, tennis, pickleball, and bocce courts, plus walking and biking trails surrounded by natural preserves. Ideally located in East Naples, you’re just a short drive from Marco Island, Downtown Naples, shopping, dining, and world-famous Gulf beaches. This home is the perfect combination of comfort, convenience, and community living.

7659 Jacaranda LN, Naples

Courtesy of Premiere Plus Realty Company.

Selling Office: Coldwell Banker Realty.

$1,000,000

3 Beds ⋅ 3 Baths ⋅ 225067249 MLS

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, bocce, state of the art fitness center and on-site director for classes! A dog park, community garden and plenty of biking and walking trails to enjoy!

7235 Clamshell LN W, Naples

Courtesy of Downing Frye Realty Inc..

3 Beds ⋅ 2 Baths ⋅ 225068633 MLS

$800,000

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 while the open layout makes entertaining effortless. With nearly 2,300 square feet of living space, this residence blends comfort, convenience and the best of the Florida lifestyle with resort living just around the corner.

7049 Live Oak DR, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Compass Florida LLC.

$835,000

3 Beds ⋅ 2 Baths ⋅ 225065830 MLS

Stunning 3-Bedroom + Den Home in Sought-After Winding Cypress – Welcome to your dream home in the prestigious, resort-style community of Winding Cypress in Naples, FL. Built in 2022, this impeccably maintained 3-bedroom + den, 2-bathroom residence blends modern design with everyday comfort. Step inside to find an open-concept floor plan featuring, abundant natural light, and contemporary finishes throughout. The kitchen boasts quartz countertops, stainless steel appliances, a large center island, and a spacious pantry—perfect for entertaining or casual family meals. The flexible den space offers the ideal setup for a home office, media room, or guest overflow. The primary suite is a serene retreat with a large walk-in closet and a spa-like ensuite bathroom featuring dual vanities and a walk-in shower. Recently installed lights on the lanai make the area glow at night. Very private preserve views! Also recently installed are electric retractable hurricane screens for added safety. Enjoy Florida living at its best with a screened lanai, ideal for relaxing or dining alfresco, with a large heated pool. The home also includes a 2-car garage, impact windows, and smart home features for added peace of mind. Residents of Winding Cypress enjoy resort-caliber amenities including a large clubhouse, fitness center, resort pool & spa, on-site restaurant, tennis & pickleball courts, fire pit, dog park, and over 800 acres of preserved natural space with walking/biking trails. Conveniently located just minutes from downtown Naples, white sand beaches, shopping, and dining. Don’t miss this rare opportunity to own a move-in ready home in one of Naples’ most desirable communities!

6902 Winding Cypress DR, Naples

Courtesy of Waterfront Realty Group Inc.

3 Beds ⋅ 2 Baths ⋅ 225064762 MLS

$860,000

This turnkey furnished Mystique home feels like a model — impeccably maintained, thoughtfully laid out, and filled with cozy, stylish touches throughout! The floorplan features 3 bedrooms + den, 2 baths, pool and spa, and an oversized car garage. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator, exterior cameras, and impact windows and doors provide peace of mind. Inside, extensive upgrades are everywhere. The kitchen boasts a spacious island with upgraded appliances, perfect for entertaining. Additional highlights include tray ceilings, crown molding, tile flooring throughout, upgraded showers in both bathrooms, and an upgraded washer and dryer. You will have tons of storage space in the air conditioned and insulated garage with an extra 4 feet of space. Outside, the pool and spa is heated by gas and hurricane screens add a second layer of protection. There are plenty of seating areas, and a picture window lanai screen to enhance the quiet, private preserve view. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location, central to Marco Island, 5th Avenue, and I- 75.

6870 Winding Cypress DR, Naples

Courtesy of Realty One Group MVP.

Selling Office: ENGEL & VOELKERS NAPLES.

$1,260,000

3 Beds ⋅ 3 Baths ⋅ 225060759 MLS

This Pinnacle floorplan is situated on the largest lake in the neighborhood and features 3 bedrooms, a den, 3 bathrooms, a pool and spa, and a 3-car garage. The open-concept layout includes a dramatic zero-corner slider that seamlessly connects indoor and outdoor living spaces. Peace of mind comes with a whole-home generator and impact-resistant windows and doors. Inside, you'll find extensive upgrades throughout. The kitchen boasts built-in appliances and a spacious island—perfect for entertaining. Additional highlights include soaring tray ceilings, crown molding in the den and entry, and tile flooring throughout. The air-conditioned 3-car (extended by 4 ft) garage offers ample storage with custom shelving and a built-in workbench. Outdoors, the heated pool and spa are powered by both gas and solar, a smart, energy-efficient combination. The expansive outdoor kitchen, hurricane screens for added protection, and generous deck space create an ideal setting for sunset views. Other exterior features include lush landscaping with low-voltage lighting, an extra-wide driveway (recently sealed), a custom designed screened-in entryway, and panoramic wide lake views. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even 2 dog parks for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—convenient to Marco Island, 5th Avenue, and I-75.

6839 Winding Cypress DR, Naples

Courtesy of Realty One Group MVP.

2 Beds ⋅ 2 Baths ⋅ 225059100 MLS

$635,000

On a premium oversized lot, this beautifully upgraded villa offers one of the most stunning sunset water views in all of Winding Cypress. The extended screened lanai features a panoramic no-see-um screen, heated saltwater pool, and a fully equipped outdoor kitchen with a five-burner Bull Grill, stainless steel sink, premium refrigerator, and a 42-inch lighted vent hood, an entertainer’s dream and the ultimate space to relax and take in the view. Hurricane-impact windows and doors throughout the home provide peace of mind, while a stylish glass entry door, two ceiling-mounted garage storage racks, and attic access in the garage and primary closet add smart functionality. Inside, the open floor plan is elegant and inviting with diagonal tile flooring, plantation shutters and upgraded LED recessed lighting. The home includes two furnished bedrooms plus a flexible den with 8-foot French doors and a new Murphy bed, ideal for guests or a home office. The gourmet kitchen features granite countertops, a tasteful tiled backsplash, staggered cabinetry with under- and over-cabinet lighting, and bar seating. California Closets have been added to the primary suite and kitchen pantry for optimal organization. This smart home includes a Nest thermostat, video doorbell, cameras at garage and lanai, Nest Protect smoke and CO2 detectors and Leviton Wi-Fi lighting switches. Gently lived in as a pet-free, smoke-free seasonal home, it shows like new. Winding Cypress offers over 800 acres of natural preserves, a resort-style clubhouse with a heated pool, restaurant, fitness center, white sand beach, tennis and pickleball courts, dog park and scenic nature trails. With low HOA fees and a natural gas community, all just 25 minutes to 5th Avenue, 20 minutes to Marco Island and five minutes to major shopping, this home blends luxury, peace of mind and lifestyle in one incredible package.

7773 Jacaranda LN, Naples

Courtesy of Premier Sotheby's Int'l Realty.

Selling Office: Re/Max Alliance Group.

$710,000

2 Beds ⋅ 2 Baths ⋅ 225057502 MLS

Step inside through a welcoming entryway and discover an open-concept floor plan. The heart of the home is the great room with tray ceiling and crown moldings, the modern kitchen, beautifully appointed with granite countertops, sleek stainless-steel appliances, and a generous center island suited for both everyday living and effortless entertaining. The primary suite offers a peaceful retreat with a walk-in closet, double vanity, walk-in shower. This beautifully cared-for home offers a rare opportunity to enjoy an elevated lifestyle in a sought-after Winding Cypress Community—

6787 Winding Cypress DR, Naples

Courtesy of William Raveis Real Estate.

Selling Office: Real Estate of South Florida.

2 Beds ⋅ 2 Baths ⋅ 225056443 MLS

Set against private garden views with tranquil eastern exposure, this beautifully appointed villa in Winding Cypress offers a peaceful retreat and effortless indoor-outdoor living. Featuring two bedrooms plus a den, two baths, and a two-car garage, this thoughtfully designed residence combines quiet luxury with meticulous updates in one of Naples’ most dynamic lifestyle communities. The screened lanai is ideal for entertaining or unwinding, complete with brick paver flooring, a saltwater pool with waterfall feature, pool heater, and recent upgrades including a new salt generator and pool pump. A custom outdoor kitchen with a stainless steel gas grill with matching hood and sink further enhances the outdoor living experience. Electric hurricane shutters protect the lanai, while manual shutters cover the remainder of the home. Inside, tile flooring extends throughout, accented by crown molding, recessed lighting, and white plantation shutters. The living room opens to the lanai through expansive glass sliders, anchored by a modern ceiling fan. The kitchen features white Shaker-style cabinetry, quartz countertops, a tile backsplash, pantry, and stainless steel appliances including a gas range, refrigerator with icemaker, microwave, and dishwasher. A modern chandelier defines the dining area, which flows easily into the main living space. The primary suite is a private haven with a tray ceiling, garden views, custom closet, and a spa-inspired bath featuring dual quartz vanities, full-width mirrors, and a frameless glass walk-in shower. The second bedroom includes a walk-in closet and an adjacent bath with a shower-tub combination. A den with French doors offers flexible space for a home office or reading room. Additional highlights include a mini-split air conditioning system in the garage, a brand-new water heater, and recent property updates including a full exterior repaint (approximately two years ago) and interior paint touch-ups. Residents of Winding Cypress enjoy access to resort-style amenities including a pool, an attended fitness center, an on-site restaurant, five tennis courts, four bocce ball courts, four pickleball courts, a community garden, and a dog park. With a vibrant social calendar, low HOA fees, rental-friendly policies, and a prime location near Marco Island, downtown Naples, 5th Avenue, and I-75, this villa offers elevated living in a premier Naples community.

7690 Jacaranda LN, Naples

Courtesy of Premier Sotheby's Int'l Realty.

2 Beds ⋅ 2 Baths ⋅ 225053774 MLS

$900,000

The perfect move in ready home for sale! This Summerwood floorplan features 2 bedrooms, 2 baths+den, saltwater pool and spa, and a 2+car garage offering a blend of style, comfort, and functionality. The open-concept layout features a dramatic zero-corner slider, seamlessly connecting indoor and outdoor spaces, while the whole home generator, exterior cameras, and impact windows and doors provide peace of mind. Inside, extensive upgrades are everywhere. The kitchen boasts built-in appliances and a spacious island, perfect for entertaining. Additional highlights include built-in Sonos speakers, crown molding, hard flooring throughout, custom primary closet, and a Murphy bed in the den—ideal for guests or a home office. The thoughtful laundry room has an upgraded washer and dryer and custom cabinets with a dedicated spot for charging your vacuum. You will have tons of storage space in the air conditioned tandem garage which can accommodate up to three cars. Outside, the saltwater pool and spa are heated by both gas and solar (a smart money-saving combo), expansive outdoor kitchen, hurricane screens for a second layer of protection, privacy lanai screening, plenty of seating areas, gorgeous lush landscaping, and areas for storage. This home has been meticulously maintained, most recently the duct work was cleaned and pavers sealed. Winding Cypress is a natural gas community with resort-style amenities! Dine at Shady Palm, the onsite restaurant, or enjoy pickleball, bocce, tennis, a state-of-the-art fitness center, a resort-style pool, a community garden, and even a dog park for your furry friend. This pet-friendly community allows rentals, has low fees, and boasts a prime location—central to Marco Island, 5th Avenue, and I- 75.

6848 Winding Cypress DR, Naples

Courtesy of Realty One Group MVP.

Selling Office: John R Wood Properties.

$674,000

3 Beds ⋅ 2 Baths ⋅ 225050266 MLS

Welcome to this beautifully appointed 3-bedroom, 2-bathroom + den home in the vibrant and sought-after community of Winding Cypress in Naples. Perfectly positioned on a prime lakefront lot, this residence offers serene, long water views that extend to the untouched beauty of the preserve beyond. Thoughtfully designed for both comfort and style, this home features tall interior doorways, an extended screened-in lanai, a fully equipped outdoor kitchen—ideal for entertaining or enjoying peaceful evenings overlooking the lake, and Enjoy the convenience of an extended garage — perfect for extra storage, a workshop space, or oversized vehicles.. Storm shutters provide added security and peace of mind, while the open and versatile layout includes a den perfect for a home office or flex space. The well-appointed kitchen boasts a gas range, catering to culinary enthusiasts, and a natural gas whole-home generator ensures uninterrupted comfort during any weather event. Additional conveniences include an HOA that covers landscaping and irrigation water, allowing for low-maintenance living. Winding Cypress is a gated, resort-style community offering an exceptional array of amenities. Residents enjoy a luxurious clubhouse, a tropical pool with waterfall features, a soothing spa, and a state-of-the-art fitness center. Recreational and social opportunities abound with pickleball, tennis, bocce, and a full calendar of community events. The Shady Palm Café serves delicious food and drinks poolside, while a scenic boardwalk winds through the community’s pristine natural surroundings. A spacious, secure dog park makes this neighborhood perfect for pet lovers as well. Conveniently located just off US-41, Winding Cypress offers easy access to world-class dining, shopping, entertainment, and the white-sand beaches that define Naples living. Experience the perfect blend of privacy, luxury, and vibrant community life in this exceptional home.

7445 Winding Cypress DR, Naples

Courtesy of KW Elevate Luxury.

Selling Office: Edgewater Realty & Homes LLC.

$990,000

3 Beds ⋅ 2 Baths ⋅ 225048066 MLS

Wow! This beautifully designed and meticulously maintained home checks all the right boxes. Featuring the highly desirable Summerwood floor plan with Great Room extension, it is perfect for entertaining or simply relaxing at home after a nice day out in beautiful Naples, FL. The kitchen features upgraded appliances, quartz countertops, an oversized island and walk-in pantry. The two guest bedrooms provide enough room for guests. The office/den can easily serve as a 4th bedroom if desired. Other interior features include high-grade porcelain tile throughout, a laundry/utility room with plenty of storage and natural gas for cooking, heated water and clothes drying. Exterior upgrades abound with a one-of-a-kind extended lanai with custom pavers and a built-in outdoor kitchen. There is plenty of space for outdoor gatherings, cookouts, an afternoon nap, a dip in the pool or just taking in some Florida sunshine. Looking through the huge portrait "no-see" lanai screen is one of the very best long water views in the entire community. The view is simply gorgeous, inspiring "wows" from all. The driveway and side walkway are extended. There is over $100k in upgrades to this magnificent home. Just pack your bags and head on down to enjoy our very special slice of tropical paradise. Worried about maintenance and insurance costs, and/or storms? Newer construction (2021) negates a large future roof replacement cost for some time. And a newer A/C system should provide many more years of solid service. Hurricane impact doors and windows are throughout providing for great energy efficiency and home protection. Also, the lot of this property is elevated. It is not in a mandatory flood insurance zone. And there is a whole home gas generator too should the need ever arise. All aforementioned should assist in obtaining lower insurance premiums and keep maintenance costs down. This home offers easy peasy and worry-free living by any measure. To top it all off, this sensational home resides in the highly prized community of Winding Cypress. An onsite restaurant, modern fitness center, community pool and a full calendar of social gatherings with some of the best Naples residents around are a nice walk, bike or golf cart ride away. Also, located conveniently between downtown Naples and Marco Island, opportunities to visit some of our finest beaches, shopping and dining locations are just minutes away. Great home. (Check.) Great view. (Check.) Great community. (Check.) Great location. (Check.) This property checks all the right boxes for the time of your life in beautiful Naples, FL.

6767 Pennyroyal DR, Naples

Courtesy of Premiere Plus Realty Company.

3 Beds ⋅ 3 Baths ⋅ 225046502 MLS

$1,175,000

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. The primary suite includes custom closets and an en-suite bath. The home is equipped with a whole-house Generac Generator, whole-house Water Purification with Reverse Osmosis, and a Built-in Surround sound system in the great room, primary bedroom, and lanai. A full home security system is also installed. Outdoor living space features an extended lanai with a custom Aragon Pool and Spa and an Upgraded Outdoor Kitchen great for Entertaining... Winding Cypress amenities include a clubhouse, fitness center, resort-style pool, tennis courts, pickleball, bocce, dog park, and nature trails.

7597 BLACKBERRY DR, Naples

Courtesy of Coldwell Banker Realty.