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3769 Helmsman DR, Naples
$985,000
4 Beds ⋅ 4.5 Baths ⋅ 226016061 MLS ⋅ CLOSED Status
Experience refined luxury and effortless Florida living at 3769 Helmsman Dr in Naples, a stunning single-story estate home located in the highly sought-after gated community of Compass Landing. Set on an oversized lot, this 4-bedroom plus den, 5-bath residence with a 3-car garage is thoughtfully designed with upscale finishes and custom details throughout. From the moment you enter, you’ll notice the elevated craftsmanship—featuring crown molding, plantation shutters, custom woodwork, a built-in desk, wainscoting in the formal dining room, and a striking accent wall in the main living area. The chef’s kitchen is beautifully appointed with KitchenAid appliances, custom cabinetry, a built-in spice rack, and an expansive pantry designed for both style and function. Additional thoughtful touches include a drop zone off the garage, added laundry room storage, and custom closets throughout. Step outside to your private backyard retreat, where a north-facing, heated saltwater pool with a sun shelf, water feature, auto-fill system, and turf accents creates the perfect setting for year-round enjoyment—all overlooking a peaceful preserve view. The spacious primary suite offers a spa-like bath with a glass-enclosed shower and soaking tub, while the flexible floor plan includes generously sized guest bedrooms and a versatile den ideal for a home office or media space. The 3-car garage is fully equipped with epoxy flooring, overhead storage, and even accommodates a refrigerator and deep freezer. Located in the highly desirable Compass Landing community, residents enjoy a resort-style clubhouse with a pool, spa, fitness center, park, and vibrant social calendar. Just minutes away, Founders Square offers a dynamic mix of restaurants, wellness services, coffee shops, and everyday conveniences. Zoned for top-rated “A” schools and perfectly positioned in North Naples, this exceptional home delivers the ultimate blend of luxury, convenience, and lifestyle.

3769 Helmsman DR, Naples
3500 Pilot CIR, Naples
$933,000
4 Beds ⋅ 4.5 Baths ⋅ 226019558 MLS ⋅ CLOSED Status
One or more photo(s) has been virtually staged, AI generated or rendered. (One or more photo(s) has been virtually staged, AI generated or rendered) Experience refined Naples living at 3500 Pilot Circle, located in the highly desirable gated community of Compass Landing. Thoughtfully upgraded throughout, this exceptional residence blends sophisticated design with effortless indoor-outdoor living. The chef-inspired kitchen features elevated finishes, a Samsung smart refrigerator, and a newer dishwasher (2024), flowing seamlessly into stylish living spaces accented by custom woodwork, upgraded lighting, and a striking feature wall. The house was painted inside and out in 2026. The spacious primary suite offers tray ceilings, upgraded mirrors, and added storage, while luxury plank flooring upstairs and a versatile loft provide both comfort and flexibility. Step outside to your private preserve-view retreat, where a heated pool and spa with water features, lighting, a tumbled marble deck, and picture-screen lanai create a true resort-style setting. Designed for entertaining, the outdoor space is already equipped for a future outdoor kitchen and enhanced with added fans, a pool bath, and seamless access to the lanai. Additional highlights include a custom laundry room, whole-home audio with JBL outdoor speakers, built-in garage storage, multiple wireless access points, and fresh paint completed in 2022. Compass Landing offers an elevated lifestyle with a resort-style clubhouse, pool and spa, fitness center, playground, and year-round social events, all just minutes from Founders Square’s dining, shopping, and wellness destinations. Perfectly positioned in North Naples near top-rated schools and world-class beaches, this home delivers luxury, convenience, and lifestyle in one exceptional package.

3500 Pilot CIR, Naples
3845 Helmsman DR, Naples
$830,000
4 Beds ⋅ 3.5 Baths ⋅ 2026005689 MLS ⋅ CLOSED Status
Welcome to 3845 Helmsman Drive in Naples, Florida. This stunning “Pennant Model” home features West Indies-inspired architecture and luxury living. With 4 bedrooms and 3.5 bathrooms, enjoy two en-suite bedrooms, a versatile guest suite, and a master retreat with a spa-like bathroom, complete with an oval soaking tub and spacious closet. The gourmet kitchen boasts an impressive 11'6" island, granite countertops, custom cabinetry, and a walk-in pantry, flowing into an expansive great room with a fireplace. The formal dining room, highlighted by a custom chandelier, complements the inviting study with French doors. Stylish touches include modern wood-look porcelain tile, crown molding, and custom carpentry. Step outside to a screened lanai with serene wooded preserve views, protected by an electric hurricane shutter and featuring a brick-paved patio—ideal for relaxation or entertaining. The 3-car garage offers ample storage with epoxy flooring. This gated community provides a lifestyle with resort-style amenities, including a pool, spa, clubhouse, fitness center, and playground. Family-friendly with access to top-rated schools, it's conveniently located near Gulf Coast beaches, golf courses, and fine dining. Move in and embrace the Naples, Florida lifestyle!

3845 Helmsman DR, Naples
3275 Pilot CIR, Naples
$780,000
3 Beds ⋅ 4.5 Baths ⋅ 226025333 MLS ⋅ CLOSED Status
Beautiful lakefront home in the gated community of Compass Landing. This spacious residence offers 3 bedrooms plus den, an upstairs loft, 3 full baths, 2 half baths, and over 3,200 sq. ft. of living space. The open floor plan features abundant natural light, a modern kitchen, generous storage, and flexible living areas ideal for everyday living and entertaining. Enjoy peaceful lake views from the screened lanai, with room to add a pool. Additional features include solar panels, whole-house reverse osmosis system, water softener, two A/C units, washer and dryer, and storm protection. Compass Landing offers resort-style amenities including a clubhouse, pool and spa, fitness center, playground, and gated access, all close to shopping, dining, schools, and everyday conveniences.

3275 Pilot CIR, Naples
3344 Pilot CIR, Naples
$662,000
3 Beds ⋅ 2.5 Baths ⋅ 226005664 MLS ⋅ CLOSED Status
We welcome you to this breathtaking 3 plus den and 2 and a half bath “West Indies” model single family home with 2,211 Sq. Ft. of living space, nestled in the highly sought after gated community of Compass Landing. This home comes with updates and upgrades abound from gorgeous lighting throughout in the interior, super gutter extensions with superior drainage in the exterior rear of the property, to overhead storage in the garage utilizing all space for convenience. This recently built home comes equipped with its roof, AC, and hot water heater all 6 years young. Greetings from the front door will welcome you through the foyer with the den and powder room on the left. The foyer opens up to the gourmet kitchen with every bell and whistle imaginable to excite any culinary enthusiast. The kitchen comes equipped with stainless steel appliances, enlarged walk-in pantry, granite counters, wainscoting finishes, disposal, beautiful backsplash, and center island. Entertaining is made a breeze with seamless flow from the kitchen to the living area and the enclosed lanai beyond with hideaway accordion doors. The discerning eye will immediately notice hand selected (interior decorated) lighting throughout the home along with custom bathroom mirrors, distinct to this home. Your primary bedroom is a true retreat with Southern exposure allowing for tons of natural light, dual vanity, zero threshold shower, and custom California-like built-in custom walk-in closet. Your out of town guests will feel resort style comfort with the generously sized guest bedrooms and guest bath with full dual vanity as well. The exterior features the enclosed lanai with gorgeous large format Accurate Pavers in the lanai and flanked on both sides of the property allowing for high and dry movement from front to back of the house. The enclosed lanai is extended at 24’x40’, ideal for entertaining any gathering, and is ready to build the pool of your dreams. Peace of mind is enhanced with laundry in residence with a laundry tub hook up already done for your convenience, manual storm shutters, interior plantation shutters, luxury vinyl flooring throughout, 2 car extended garage, and attic with installed plywood throughout. Compass Landing enjoys a fabulous clubhouse with exercise room, club room, community pool, and spa. Your home has a fabulous central location with Founders Square, Logans Landing, and Publix all less than 8 minutes away with the white sandy shores of the Gulf less than 20 minutes from your front door. A newly rezoned school district, Compass Landing offers fantastic A+ rated schools. Come check out this fabulous opportunity!

3344 Pilot CIR, Naples
3387 Pilot CIR, Naples
$657,000
3 Beds ⋅ 2.5 Baths ⋅ 226000656 MLS ⋅ CLOSED Status
Modern, move-in ready, and effortlessly fresh, this Craftsman-style home at 3387 Pilot Circle offers the perfect blend of thoughtful design, quality upgrades, and a connected North Naples lifestyle. Located in the gated community of Compass Landing, this like-new residence stands out for its light-filled spaces, smart functionality, and timeless architectural details. Soaring vaulted ceilings create an immediate sense of openness in the entry and primary suite, while the chef’s kitchen anchors the home with quartz countertops, upgraded cabinetry, and LED under-cabinet lighting. Custom touches—including a birch slab built-in desk, framed mirrors, laundry room cabinetry, and a charming built-in bench—add warmth, character, and everyday practicality. Bathrooms feature tile extended to the ceiling with elevated finishes, and every bedroom is thoughtfully equipped with dimmer switches and coax wiring. The home opens to peaceful water views from every rear window and offers a fully fenced backyard with a privacy wall, screen-enclosed lanai, and pre-wiring for a future pool—ideal for both relaxation and entertaining. Additional upgrades include epoxy-coated garage floors and built-in garage storage, rounding out a home that truly feels dialed-in and complete. Compass Landing is known for its welcoming, community-driven atmosphere, featuring a resort-style clubhouse, pool and spa, fitness center, shaded playground, and a full calendar of neighborhood events. Zoned for Bear Creek Elementary and Gulf Coast High School, and just minutes from Founders Square—where dining, coffee, fitness, and everyday conveniences are easily reached by golf cart, bike, or car—this home delivers style, comfort, and location in one seamless package.

3387 Pilot CIR, Naples
3865 Helmsman DR, Naples
$645,000
3 Beds ⋅ 2 Baths ⋅ 226020581 MLS ⋅ CLOSED Status
UPGRADED HOME WITH A 3-CAR GARAGE - OVERSIZED LOT & PRESERVE VIEWS! Welcome to this customized residence showcasing PREMIUM FINISHES and upgrades throughout on ONE OF THE LARGEST LOTS IN THE COMMUNITY. Ideally positioned near the end of a quiet cul-de-sac in the highly sought-after community of Compass Landing, this beautifully maintained 2020 home offers 2,176 square feet of well-designed living space with 3 bedrooms, 2 bathrooms, and a versatile den with French glass doors. Enhanced with DESIGNER FINISHES, the home features upgraded cabinetry, QUARTZ COUNTERTOPS, custom lighting and fixtures, TILE FLOORING throughout (no carpet), tray ceilings with recessed lighting, detailed CROWN MOLDING, 8-foot doors, and abundant storage. The CHEF’S KITCHEN serves as the centerpiece with premium 42” cabinetry, bronze hardware, stainless steel Whirlpool appliances, a large pantry, and an oversized island with decorative detailing. The spacious owner’s suite offers TWO WALK-IN CLOSETS and a luxurious en-suite bath with Sonos speakers, dual vanities, linen closet, and oversized walk-in shower. A fully built-out laundry room includes additional cabinetry, counter space, and a sink. Enjoy seamless indoor-outdoor living from the screened lanai overlooking peaceful preserve views, complete with a brick-paved patio and room to add a pool. Additional highlights include a full 3-CAR GARAGE with overhead storage, speaker system, upgraded gutters and downspouts, and a combination of impact glass, roll-down, and plexiglass shutters for added peace of mind. Residents of Compass Landing have access to resort-style amenities including a clubhouse, pool and spa, fitness center, playground, and year-round community events. Conveniently located in North Naples near Founder’s Square, shopping, dining, and top-rated schools. THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER, INQUIRE FOR MORE DETAILS. Renderings that showcase furniture have been virtually staged

3865 Helmsman DR, Naples
3529 Pilot CIR, Naples
$640,000
3 Beds ⋅ 2.5 Baths ⋅ 225082047 MLS ⋅ CLOSED Status
MOTIVATED SELLERS! Rare opportunity to own like-new construction in North Naples! This craftsman-style home offers charm and premium south-facing lake with fountain views from all of its extended back lanai. Built in 2020 and very well maintained, the home features a chef’s kitchen with upgraded cabinets and a stunning open layout designed for everyday living and indoor/outdoor entertaining. The welcoming front porch leads into a bright entry with high ceilings. Two guest bedrooms and a full bathroom are positioned toward the front of the home, offering separation from the main living areas. The open-concept chef’s kitchen includes premium cabinetry, a large bar seating area, walk-in pantry, serving space, updated light fixtures, and connects seamlessly to the main living and dining areas. The den includes fully opening glass doors and provides flexible use as a home office or additional living space. The primary bedroom suite features a luxurious spacious shower and a walk-in closet. Sliding doors open to an extended, no-see-um screened lanai offering outdoor living space with water views and added privacy. Accordion and motorized shutters provide storm protection with quick closure. The home is conveniently located within walking, biking, or golf-cart distance to Founders Square, with restaurants, fitness options, medical offices, and retail nearby. Compass Landing amenities include a pool and spa, clubhouse, fitness center, event space, locker rooms with showers, and a covered playground, along with low HOA fees and an active community calendar. Some photos include reality renovation/reality staging. This property includes interior design services, making furnishing this property easy for your buyer.

3529 Pilot CIR, Naples
3480 Pilot CIR, Naples
$630,000
3 Beds ⋅ 2.5 Baths ⋅ 226015992 MLS ⋅ CLOSED Status
The book says, "Buy the least expensive home in the best neighborhood". Don’t miss your chance. First time being offered by its original owner. Welcome to 3480 Pilot Circle, an exceptional West Indies-inspired residence located in the private, gated community of Compass Landing in highly desirable North Naples. This like-new, single-family home blends modern craftsmanship, thoughtful upgrades, and timeless architectural design to create a truly standout living experience, featuring Mattamy Homes’ most successful Banyan floor plan with the ease and convenience of single-story living. From the moment you enter, soaring vaulted ceilings, oversized doors, and abundant natural light set the tone for a bright, open, and inviting interior. The thoughtfully designed floor plan offers a seamless flow between living spaces, emphasizing both comfort and functionality. The open-concept layout is ideal for everyday living and entertaining alike, with a distinct separation between the main living areas and guest bedrooms to ensure privacy for family and visitors. At the heart of the home, the chef’s kitchen impresses with a large center island, stainless steel appliances, sleek cabinetry, and generous storage, perfectly suited for casual meals or hosting gatherings. The spacious living and dining areas extend effortlessly, creating a cohesive space that feels both expansive and welcoming. Step outside to enjoy a rare, oversized backyard with additional green space, ideal for pets, play, or simply relaxing, set against a peaceful and private preserve backdrop. Compass Landing is known for its warm, community-oriented atmosphere and resort-style amenities, including a 2,600 square foot clubhouse, pool and spa, fitness center, shaded playground, and a full calendar of social activities. Residents also enjoy being just moments from Founders Square, offering a vibrant mix of restaurants, coffee shops, wellness services, Ace Hardware, and everyday conveniences, all easily accessible by car, bike, or golf cart. Perfectly positioned near I-75, Mercato, Waterside Shops, and the white sandy Gulf beaches, this home offers unmatched convenience. Zoned for top-rated Collier County “A” schools, including Gulf Coast High School, Oakridge Middle, and Bear Creek Elementary, the location is as desirable as the home itself. Modern, move-in ready, and effortlessly stylish, this property delivers the ultimate blend of luxury, comfort, and North Naples lifestyle. Don’t miss this exceptional opportunity to experience the very best of Southwest Florida living.

3480 Pilot CIR, Naples
3292 Pilot CIR, Naples
$625,000
4 Beds ⋅ 2 Baths ⋅ 226027215 MLS ⋅ CLOSED Status
One or more photo(s) has been virtually staged, AI generated or rendered. Welcome to 3292 Pilot Circle in the highly sought-after gated community of Compass Landing. This beautifully maintained 4-bedroom, 2-bath residence offers an open-concept floor plan with over 2,100 square feet of thoughtfully designed living space, combining comfort, functionality, and modern style. The spacious kitchen is the heart of the home, featuring a large center island, stainless steel appliances, abundant cabinetry, and generous counter space—perfect for everyday living and entertaining. Natural light fills the great room, creating a bright and inviting atmosphere, while the flexible den provides the ideal space for a home office, playroom, or additional guest accommodations. The private primary suite offers a relaxing retreat with a walk-in closet, dual vanities, and a spacious walk-in shower. Step outside to enjoy the newly screened lanai, overlooking a backyard with plenty of room to design your dream outdoor oasis or add a custom pool. Compass Landing is a gated community with low HOA fees and exceptional amenities, including a clubhouse, fitness center, and community pool. Conveniently located near top-rated schools, shopping, dining, and everything Naples has to offer, this home presents an outstanding opportunity to enjoy the Southwest Florida lifestyle. Competitively priced and move-in ready, this home represents one of the best values in Compass Landing. Don't miss this opportunity to own a beautiful home in one of North Naples' most desirable gated communities.

3292 Pilot CIR, Naples

The data relating to real estate for sale on this web site comes in part from the Broker Reciprocity Program (BR Program) of M.L.S. of Naples, Inc. Properties listed with brokerage firms other than this company are marked with the BR Program Icon or the BR House Icon and detailed information about them includes the name of the listing brokers. The properties displayed may not be all the properties available through the BR Program. The information provided is for consumers’ personal, non-commercial use and may not be used for any other purpose.