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Anchors Aweigh Houses Sold

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Results 17 of 17
Sold - Jul 9, 2026
Shell Harbor, 734 Anchor Dr, Sanibel, Florida 33957, image 1
$850,000$350K
  • 3 Beds
  • 2 Baths
  • 1,451 SqFt
  • $586/SqFt
House sold in Shell Harbor
734 Anchor Dr, Sanibel, FL 33957
Nestled on the peaceful east end of sanibel along tranquil anchor drive, this unique ground-level home offers the ultimate in easy island living. Positioned on a desirable canal front lot, this property is a boater's dream, complete with a private boat dock. The canal provides quick access to open water, with just one picturesque bridge to navigate along the way. Surrounded by lush, natural vegetation, this home feels like a private retreat, where wildlife lovers will delight in daily sightings of tropical birds, jumping fish, and perhaps even a curious manatee or dolphin passing through the canal. Imagine relaxing on your screened lanai, taking in the serene water views and the sounds of nature. For beach enthusiasts, a short walk or bike ride down a deeded path leads to sanibel's stunning sandy shores. The home’s thoughtful design includes a large kitchen window that slides open, allowing fresh breezes to flow inside and providing convenient access to the lanai for effortless outdoor dining. This property offers exciting potential for a fresh start. A new roof and relined drainpipes were added in 2019, and now, following hurricane helene and milton, it’s ready for the next owner to reimagine and remodel it into their perfect island escape. Whether you're a boater, a beachcomber, or a nature lover, this east end gem provides the perfect canvas to create your sanibel dream home.
Sold - Jun 15, 2026
Anchors Aweigh, 739 Anchor Dr, Sanibel, Florida 33957, image 1
$1,600,000$95K
  • 3 Beds
  • 2 Baths
  • 2,209 SqFt
  • $724/SqFt
Mid-Tier
House sold in Anchors Aweigh
739 Anchor Dr, Sanibel, FL 33957
Driving up to this property you immediately notice the brick paved park-like road. It leads to a secluded home on an oversized lot that resembles a botanical garden. Blooming hibiscus, ginger, jasmine and fragrant gardenia surround this raised home on the sought after east end. As you enter the open living and dining room with raised ceilings you are greeted by a wood burning fireplace all nestled next to an open kitchen with granite counter tops and new appliances, including an induction stove that cooks like gas. Deeded beach access a short walk away, 10, 000lb boat lift and a private kayak launch flank a beautiful pool with outdoor grill area. A large open-covered deck overlooking pool and mangrove lined canal plus roof top solar panels tied to the grid where the electric company pays you for electricity. This home is truly one of a kind.
Sold - Apr 24, 2026
Anchors Aweigh, 668 Anchor Dr, Sanibel, Florida 33957, image 1
$1,100,000
  • 3 Beds
  • 2 Baths
  • 1,999 SqFt
  • $550/SqFt
Mid-Tier
House sold in Anchors Aweigh
668 Anchor Dr, Sanibel, FL 33957
Beautiful east-end sanibel retreat offering gulf access, a private tropical pool setting, and convenient beach access just steps away. This charming 3bd/2ba home has been completely remodeled and thoughtfully reinvented, blending modern coastal elegance with relaxed island living. The updated kitchen serves as the heart of the home, featuring custom cabinetry, quartz countertops, designer lighting, new appliances, and a built-in wall pantry. An open split floor plan provides comfortable living and easy entertaining, with a spacious family room and full bath conveniently located just off the pool and lanai. The home offers abundant storage throughout, including a large storage closet off the family room and an expansive laundry room with a built-in desk/work area. Outdoor living shines with a screened lanai and sparkling pool surrounded by lush tropical landscaping, creating a private island retreat on an oversized 19, 000+ sq. Ft fenced lot. The peaceful canal setting offers gulf access and exceptional privacy, while beach access is just moments away via the charming footbridge at the end of anchor drive.
Sold - Mar 6, 2026
Anchors Aweigh, 732 Windlass Way, Sanibel, Florida 33957, image 1
$1,475,000
  • 4 Beds
  • 31/2 Baths
  • 3,003 SqFt
  • $491/SqFt
Mid-Tier
House sold in Anchors Aweigh
732 Windlass Way, Sanibel, FL 33957
Enter this dreamy island retreat, a beautifully appointed and updated canal home that captures the essence of sanibel living at its finest. This four-bedroom residence blends coastal elegance with relaxed sophistication. It’s on a lovely private street with a cul-de-sac in one of the island’s desirable east-end neighborhoods. Ideally close to everything, including a private beach path with deeded access to the gulf’s world-class shelling beaches, scenic bike trails, restaurants in short distance, and easy on- and off-island access. Designed with comfort and ease in mind, the home features quality finishes and amenities that make island living effortless. The home has been beautifully updated with a timeless coastal palette and a thoughtful list of improvements. Blending beauty with function, the home has been recently enhanced with all-new appliances, a new whole-house generator, a 1, 000-gallon buried propane tank, new air-conditioner, new gutters, impact-resistant windows and more. It’s a mix of practicality and understated luxury. The oversized 47-foot private dock rests just beyond your lanai along a gulf-access canal, offering an ideal setting to keep your boat, launch a kayak or cast a line. Upstairs, a private balcony overlooks the treetops and canal, a peaceful hideaway where mornings are calm and quiet, and evenings turn magical. The inviting pool and spa area offers complete privacy, surrounded by lush tropical landscaping, the ideal place to unwind after a day on the water or at the beach. Enjoy breakfast on the lanai surrounded by tropical foliage and island breezes or follow your private path to the beach for a quiet morning walk along the soft white sands just minutes away. A serene haven where every day feels effortlessly relaxed.
Sold - Feb 2, 2026
Anchors Aweigh, 748 Windlass Way, Sanibel, Florida 33957, image 1
$1,210,000
  • 3 Beds
  • 3 Baths
  • 2,849 SqFt
  • $425/SqFt
Mid-Tier
House sold in Anchors Aweigh
748 Windlass Way, Sanibel, FL 33957
An incredible opportunity! Offering an exceptional amount of home and lifestyle, a find unlikely to be seen again. On sanibel’s desired east end, this home on an elevated lot, offers one of the island’s convenient and desirable locations. A deeded beach path leads directly to a pristine gulf shoreline, known for its endless shells and soft white sand. Everything that makes sanibel special, the beaches, the bike paths, the island’s vibrant yet peaceful atmosphere, is right at your doorstep. From this home, you’re just moments from charming cafés, restaurants, and shops, with easy on and off island access. The wide canal-front retreat embodies the essence of sanibel living, where tranquility meets adventure. From your own private oversized dock with a 10, 000-pound boat lift, you can cast a line, paddleboard through winding mangrove-lined canals, or launch your boat for easy direct access to the gulf. Dolphins are frequently spotted right off your dock, adding a touch of everyday magic. The home itself is generously scaled and thoughtfully designed for gathering and quiet retreat. Recently updated, it features a new kitchen with all new appliances, updated baths, a new roof and numerous additional upgrades throughout. The pool area is ideal for relaxed afternoons or a refreshing dip after a day at the beach. Two inviting balconies capture gentle gulf breezes and offer vantage points to enjoy the island’s best times of day, from soft morning light to glowing sunset skies. This is your time to stop dreaming and start living the sanibel life.
Anchors Aweigh, 736 Windlass Way, Sanibel, Florida 33957, image 1
$1,225,000
  • 3 Beds
  • 2 Baths
  • 2,096 SqFt
  • $584/SqFt
Mid-Tier
House for sale in Anchors Aweigh
736 Windlass Way, Sanibel, FL 33957
Wake up to the soothing sounds of birdsong and step through elegant french doors into a lush, tropical garden where the morning sun filters through swaying palms. Enjoy your coffee by the shimmering saltwater pool, surrounded by vibrant flowers and the gentle rustle of island breezes, or wander down to your private wraparound dock to cast a line as the first light of day reflects off the water. Bordered on two sides by navigable, intersecting canals, this exceptional property offers a rare combination of privacy and waterfront access. A charming footbridge at the end of the street provides an easy and scenic stroll to the deeded beach access, where soft sands and gulf waters await. Whether you're spending the day on the water or enjoying the tropical landscape of your expansive yard, this home seamlessly blends island charm with the ultimate boating lifestyle. With expansive canal frontage, a boathouse, and a 10, 000-pound boat lift, your days can be spent exploring the waterways with your boat, kayaking at sunrise or setting off for an afternoon on the bay in just minutes. The quick and easy access to open water makes this a boater’s paradise, where spontaneous sunset cruises and island-hopping adventures are always within reach. This beautifully remodeled home is designed for effortless island living, with inviting spaces that flow seamlessly between indoors and out. A cozy fireplace offers the spot to unwind on cooler evenings, while high-end finishes, including commercial-grade luxury flooring and quartz countertops, add a refined touch to the home’s relaxed coastal feel. With a new trane air conditioner and roof, every detail has been thoughtfully considered for comfort and peace of mind. On an oversized lot with exceptional privacy, this is a place where nature and tranquility take center stage. On sanibel’s desirable east end, the home is just a short stroll from pristine beaches, charming shops and local restaurants, and offers easy on-and-off access to the island, though with a setting this idyllic, you may never want to leave. This is more than a home, it’s a sanctuary where every day feels like a vacation. Don’t miss this rare opportunity to live the island life you’ve always dreamed of.
Anchors Aweigh, 707 Anchor Dr, Sanibel, Florida 33957, image 1
$2,600,000
  • 3 Beds
  • 21/2 Baths
  • 3,284 SqFt
  • $792/SqFt
Mid-Tier
House for sale in Anchors Aweigh
707 Anchor Dr, Sanibel, FL 33957
Captivating coastal retreat on sanibel island! This completely renovated two-story gem epitomizes modern coastal living. Nestled in a prime east-end location, this gulf access property offers a seamless blend of sophistication & the relaxed charm that defines the island lifestyle. As you step inside, the attention to detail is immediately evident. The residence has undergone a complete transformation, featuring a brand-new interior adorned with transitional finishes, a gourmet kitchen & butler's pantry equipped with wolf and sub-zero appliances, and fully integrated smart house features (security, media, lighting, locks, cameras, etc.). The open-concept design bathes the space in natural light. The result is a home that not only meets but exceeds the expectations of modern luxury. The spacious living areas effortlessly extend to the outdoors. Imagine entertaining on the expansive deck, overlooking the sparkling pool, or relishing the convenience of the private dock with a boat lift—your gateway to gulf waters for endless maritime adventures. A quick 5-minute walk, across the cul-de-sac foot bridge, to the beach. Don't miss the opportunity to call this retreat your home.
Anchors Aweigh, 698 Anchor Dr, Sanibel, Florida 33957, image 1
$1,615,000
  • 5 Beds
  • 51/2 Baths
  • 3,220 SqFt
  • $502/SqFt
Mid-Tier
House for sale in Anchors Aweigh
698 Anchor Dr, Sanibel, FL 33957
Bring your boat to this spanish style canal front home with dock and lift offering access to the gulf of mexico and san carlos bay. Located on the east end of the island, this community enjoys deeded beach access by way of a charming bridge or bike on the nearby path to close-by restaurants, shops, marina, and historic lighthouse. This 5br/5.5ba ground-level home has been remediated from the effects of the storm and is ready to be customized. Very spacious layout with open concept kitchen/dining/living area with high ceilings. There is a detached casita with 1br/1ba and living room with french doors leading to a private screened porch. The backyard is a private oasis, and the pool has been cleaned and restored and is surrounded by a beautiful paver deck. This home is located on one of the most picturesque streets and is a beach and boating lover’s paradise!
Anchors Aweigh, 740 Windlass Way, Sanibel, Florida 33957, image 1
$845,000
  • 2 Beds
  • 2 Baths
  • 1,152 SqFt
  • $734/SqFt
Mid-Tier
House for sale in Anchors Aweigh
740 Windlass Way, Sanibel, FL 33957
Sanibel estates with deeded beach access! Don’t miss this incredible opportunity to own an oversized windlass way lot boasting over130 feet of canal frontage on one of the widest canals in the community. This 2 bedroom, 2 bathroom home offers pool with a spa, double car garage, screened lanaiand over 1150 square feet. All drywall has been removed and home has been fully remediated. Screen enclosure still intact just needing replacement screens.Seawall repair contract in place. 2015 tile roof in great condition! Windlass way waterway wraps around to a 4-way intersecting canal, with two bridges out to thegulf of mexico. Convenient east-end location with proximity to restaurants, retail, and ease on/off island.
Anchors Aweigh, 760 Windlass Way, Sanibel, Florida 33957, image 1
$925,000
  • 3 Beds
  • 3 Baths
  • 2,238 SqFt
  • $413/SqFt
Mid-Tier
House for sale in Anchors Aweigh
760 Windlass Way, Sanibel, FL 33957
Spanning nearly half an acre of land, this canal front property sits at the end of a quiet cul-de-sac on the east end of sanibel island. With only one bridge to cross under, boaters can be in the gulf waters in no time. This spacious ground-level pool home has been gutted following hurricane ian and is ready for your renovation. Enjoy a large yard, canal with dock, metal roof with solar panels still intact, and easy access to the causeway. This property was appraised at $2m following hurricane ian.
Anchors Aweigh, 746 Windlass Way, Sanibel, Florida 33957, image 1
$2,150,000
  • 4 Beds
  • 3 Baths
  • 2,615 SqFt
  • $822/SqFt
Mid-Tier
House for sale in Anchors Aweigh
746 Windlass Way, Sanibel, FL 33957
East end home! Wonderfully spacious, renovated, ground level home offers cathedral ceilings in the great room with living room, kitchen and dining. Super floorpan with four bedrooms and three bathrooms, including a spacious master with top notch bathroom. Beautiful terrazzo floors throughout this house. Seawall canal in the shell harbour canal system with boat dock and jet ski landing, plus tropical pool and spa. The beach is a short walk away. Impact windows and doors. Kitchen offers a gas cooktop, wall oven, jennaire stainless refrigerator, wine cooler, warming drawer, custom solid wood cabinetry, granite counter tops and large center island with vegetable sink.
Anchors Aweigh, 719 Periwinkle Way, Sanibel, Florida 33957, image 1
$1,750,000
  • 4 Beds
  • 3 Baths
  • 2,768 SqFt
  • $632/SqFt
Mid-Tier
House for sale in Anchors Aweigh
719 Periwinkle Way, Sanibel, FL 33957
Warmly welcoming mediterranean style east end canal home with 4 br/3ba and fabulous new artist studio/office space (which could be converted to additional bedrooms and bath, if preferred). From your separate ground level suite, your screened lanai and the 4th bedroom /media room you can view the lush mangrove-bordered canal and hear the splashes of the jumping mullet. The home features nicely flowing interior space with mexican tile floors. The charming courtyard pool is surrounded by tropical plants and trees including a show-stopping ficus and a bountiful mango. From your private dock, the canal gives easy access to san carlos bay and the gulf of mexico. The home is right at the bike path, and it’s close to the causeway for easy on/off the island. Don’t miss your chance to own this unique piece of paradise!
Anchors Aweigh, 699 Anchor Dr, Sanibel, Florida 33957, image 1
$2,395,000
  • 4 Beds
  • 4 Baths
  • 3,010 SqFt
  • $796/SqFt
Mid-Tier
House for sale in Anchors Aweigh
699 Anchor Dr, Sanibel, FL 33957
This meticulous three-story home checks all the boxes! East end, intersecting canal front, dock with 10, 000 lb boat lift. Four-minute walk to beach path, completely renovated inside and out. Four bedrooms and four bathrooms, elevator, large screened lanai, sun deck, newer roof, impact windows, exterior siding and garage doors. Remodel in 2019 includes new bathrooms, beautiful kitchen open to family room with custom cabinetry, quartz countertops, stainless steel appliances and large center island with bar seating. Living room open to dining room and sundeck. Primary suite includes large open deck, unique custom-vaulted ceilings, and a luxurious bathroom. Canal views, oversized lot, large, heated pool, soaring ceilings, fully furnished, excellent lower-level storage, new landscaping just completed. If you are looking for privacy, seclusion, steps to the beach, boat dockage and easy access to the causeway this east end beauty has it all! Don't delay. This unique opportunity won’t last!
Anchors Aweigh, 752 Windlass Way, Sanibel, Florida 33957, image 1
$1,150,000
  • 3 Beds
  • 2 Baths
  • 2,018 SqFt
  • $570/SqFt
Mid-Tier
House for sale in Anchors Aweigh
752 Windlass Way, Sanibel, FL 33957
Welcome to this meticulously cared-for, elevated 3-bedroom, 2-bathroom canal-front home, located on a peaceful cul-de-sac on the popular east end of sanibel island. With quick gulf access just minutes away, bring your boat and enjoy the waterways right from your backyard. This home boasts beautiful wood floors throughout, adding warmth and charm to the space. The updated kitchen features stainless steel appliances, stunning quartz countertops, and an open layout that seamlessly flows into the family room. Sliders from the family room lead to a screened porch that overlooks the canal, offering beautiful western exposure – the perfect spot to enjoy the breathtaking sanibel sunsets. The spacious primary bedroom also offers access to the porch and features an en-suite bathroom for added privacy and comfort. The two generous guest rooms share a well-appointed hall bathroom, providing ample space for family or visitors. The living room is another inviting area that opens to the porch, making this home perfect for entertaining. Additional highlights include a brand-new roof, a large 2-car garage, under-house storage, a separate laundry room, and updated lighting throughout. Located in a prime spot, you’ll be just minutes from the bike path, shops, restaurants, marina, and the bridge for easy access on and off the island. Don't miss out on this beautiful home in a fantastic location!
Anchors Aweigh, 748 Windlass Way, Sanibel, Florida 33957, image 1
$1,395,000
  • 3 Beds
  • 3 Baths
  • 2,849 SqFt
  • $490/SqFt
Mid-Tier
House for sale in Anchors Aweigh
748 Windlass Way, Sanibel, FL 33957
Experience the ultimate island lifestyle in this beautifully remodeled 3-bedroom, 3-bath canal-front home on sanibel's desirable east end. Nestled on a tranquil cul-de-sac, this property boasts a private boat dock and lift, offering direct gulf of mexico access for boating enthusiasts. The open-concept design features a chef’s kitchen with high-end appliances, a spacious island, and elegant quartz countertops. Large sliders lead to the screened lanai, overlooking a sparkling pool and serene canal views. Deeded beach access provides a quick stroll to sanibel's renowned sandy shores, while nearby shops, restaurants, the bike path, the historic lighthouse, and the marina add to the home's appeal. Recent updates include re-piping, fresh exterior paint, and a new roof set for installation in january 2025. Whether you’re hosting guests or savoring quiet moments, this home perfectly combines luxury, convenience, and coastal charm.
Anchors Aweigh, 659 Anchor Dr, Sanibel, Florida 33957, image 1
$2,895,000
  • 3 Beds
  • 31/2 Baths
  • 3,063 SqFt
  • $945/SqFt
Mid-Tier
House for sale in Anchors Aweigh
659 Anchor Dr, Sanibel, FL 33957
The perfect sanibel home does exist and can be found on the desirable east end at 659 anchor drive! Upon arrival to the oversized .45 acre canal-front lot you are greeted by a gorgeous newer (2019) custom built 3, 100+/- sf home that was executed to exacting standards, thoughtfully and tastefully finished, and meticulously cared for by the original owners. The end result is an island masterpiece that lives lavishly, shows like a model, and is perfectly positioned to enjoy the island lifestyle to the fullest. Take a short walk over the eclectic footbridge to the beach, bike to the historic lighthouse, meander down to some of the islands best shops/dining, and appreciate the quick on/off island access with close proximity to the causeway or by boat from your private composite dock. The homebody in you will appreciate the desirable floor plan with distinguished vaulted ceilings and hardwood floors throughout, a large private master retreat, gourmet kitchen with all the bells and whistles + walk in pantry, hydraulic elevator, tankless water heaters, guest wing with 2 ensuite bedrooms, large office, additional den, spacious lanais, heated pool + spa, a 2 car+ garage, and so much more!
Anchors Aweigh, 727 Periwinkle Way, Sanibel, Florida 33957, image 1
$1,475,000
  • 3 Beds
  • 3 Baths
  • 2,154 SqFt
  • $685/SqFt
Mid-Tier
House for sale in Anchors Aweigh
727 Periwinkle Way, Sanibel, FL 33957
Discover the perfect blend of luxury, comfort & coastal charm in this stunning & remodeled 3 bedroom & 3 full baths canal-front home. Enjoy easy on & easy off in a sought-after east end location. You will appreciate the complete renovation with every detail carefully curated for modern living. All mechanical systems have been upgraded, including metal roof, wind-rated garage door, new electric, plumbing, sewer pipes, 2-zoned central air units, water heater, pool equipment, & impact-resistant windows, sliders & doors. Step inside to find a spacious open floor plan, where the kitchen serves as the heart of the home. With upscale ge monogram appliances, gas cooktop, quartz countertops, & soft close cabinets, the gourmet kitchen is both functional & timeless—perfect for the family cook or entertaining guests. A dry bar acts as an adjacent extension of the kitchen. The living, dining & family rooms surround the kitchen & feature views of the lush yard & sparkling pool, while a wall of impact-glass sliding doors invite the outside in. Vaulted ceilings & recessed lighting throughout add an extra layer of sophistication. Tile floors offer easy care & maintenance. Your very spacious primary suite is a true retreat, offering a serene space with a luxurious en-suite bath featuring a dual-sink vanity, walk-in shower, & an oversized custom walk-in closet for ultimate convenience. Sliding doors offer access to the pool & large screened lanai. An office nook is located adjacent to the primary suite. The all en-suite split bedroom floor plan allows privacy for guests & owners alike. Outside, your private oasis awaits. Newly resurfaced, heated pool with anti-slip, quick dry, natural shell stone deck basks in south & west-facing sunlight throughout the day. Lush, native landscaping with many salt tolerant plants & bushes, ensure privacy, while a covered sun porch offers the perfect space to relax, read, or unwind. For boating & fishing enthusiasts, the canal provides access to the gulf, along with a pier, fish cleaning table & water & electricity for added convenience. Perfect for kayaks & smaller boats. Easy access to the sanibel marina & grandma dots restaurant, plus other venues for dining & shopping, the historic lighthouse & of course, sanibel’s world-renowned beaches—just a short walk or bike away. Location, luxury, & lifestyle come together in this spectacular island home. Make it yours today & start living the sanibel dream! Most furnishings are negotiable.

Subdivision Amenities

Bike And Jog Path
Boat Storage
Community Gulf Boat Access
Fish Cleaning Station
Fishing Pier
Guest Room
Hobby Room
Internet Access
Marina
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Storage
Beach Access
None

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Walk Score®
Car-Dependent. Almost all errands require a car
18

100
Bike Score®
Very Bikeable. Biking is convenient for most trips
79

100
Sound Score®
Bearable noise
81

100
Airport Score
Close to airports. Noticeable airport activity
0

100
Traffic Score
Congested area. Frequent traffic delays
25

100
Local Score
Limited local amenities nearby
0

100

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