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$1,425,000

Experience the very best of Pine Island waterfront living in this exceptional harbor front estate, where panoramic Charlotte Harbor views, unmatched boating access, and breathtaking sunrises and sunsets create a lifestyle few properties can offer. Tucked away behind a private gated entrance, this custom waterfront retreat features an impressive 400-foot private dock with two 10,000-pound boat lifts, water and electric service, and direct, no-bridge access to some of Southwest Florida's most sought-after destinations, including Boca Grande, Cayo Costa, North Captiva, Cabbage Key, and world-class fishing waters. Designed to capture spectacular water views from nearly every angle, the main living level is easily accessed by either the staircase or your private elevator. Inside, soaring cathedral ceilings and an open-concept great room frame spectacular Charlotte Harbor views, creating a bright and inviting space designed for entertaining. The updated kitchen is beautifully appointed with premium stainless-steel appliances, a Viking range hood, gas cooktop, beverage cooler, trash compactor, abundant cabinetry, and generous workspace, making it ideal for both everyday living and entertaining. The spacious primary suite offers a zero-entry walk-in shower, and handicap accessibility. Three additional guest bedrooms on the main level provide plenty of room for family and friends. The lower level offers exceptional flexibility with a fully equipped private guest suite featuring its own kitchen, living room, bedroom, full bathroom, den, and screened lanai with above ground hot tub. Whether used for multigenerational living, extended guests, a home office, or as a potential income-producing rental, this separate living space adds tremendous value and versatility. Outside, the waterfront lifestyle truly comes to life. Spend your mornings enjoying coffee from the end of your private dock as the sun rises over Charlotte Harbor, then return in the evening to watch unforgettable sunsets over Boca Grande Pass. Launch your boat from one of two lifts and be cruising to secluded beaches, waterfront restaurants, or some of Florida's finest fishing grounds within minutes. Dolphins, manatees, and spectacular coastal wildlife are frequent visitors, making every day feel like a vacation. Built with peace of mind in mind, the home also features a durable metal roof, impact-resistant windows, electric hurricane shutters, propane service, and a private elevator, combining comfort, accessibility, and storm-ready construction. Properties offering this level of privacy, protected harbor frontage, boating convenience, and flexible living space are exceptionally rare. Whether you're searching for a full-time residence, seasonal retreat, or waterfront legacy property, this remarkable home offers an unparalleled opportunity to embrace the very best of the Pine Island lifestyle.

5 Beds ⋅ 3 Baths ⋅ 2026029600 MLS

Experience the very best of Pine Island waterfront living in this exceptional harbor front estate, where panoramic Charlotte Harbor views, unmatched boating access, and breathtaking sunrises and sunsets create a lifestyle few properties can offer. Tucked away behind a private gated entrance, this custom waterfront retreat features an impressive 400-foot private dock with two 10,000-pound boat lifts, water and electric service, and direct, no-bridge access to some of Southwest Florida's most sought-after destinations, including Boca Grande, Cayo Costa, North Captiva, Cabbage Key, and world-class fishing waters. Designed to capture spectacular water views from nearly every angle, the main living level is easily accessed by either the staircase or your private elevator. Inside, soaring cathedral ceilings and an open-concept great room frame spectacular Charlotte Harbor views, creating a bright and inviting space designed for entertaining. The updated kitchen is beautifully appointed with premium stainless-steel appliances, a Viking range hood, gas cooktop, beverage cooler, trash compactor, abundant cabinetry, and generous workspace, making it ideal for both everyday living and entertaining. The spacious primary suite offers a zero-entry walk-in shower, and handicap accessibility. Three additional guest bedrooms on the main level provide plenty of room for family and friends. The lower level offers exceptional flexibility with a fully equipped private guest suite featuring its own kitchen, living room, bedroom, full bathroom, den, and screened lanai with above ground hot tub. Whether used for multigenerational living, extended guests, a home office, or as a potential income-producing rental, this separate living space adds tremendous value and versatility. Outside, the waterfront lifestyle truly comes to life. Spend your mornings enjoying coffee from the end of your private dock as the sun rises over Charlotte Harbor, then return in the evening to watch unforgettable sunsets over Boca Grande Pass. Launch your boat from one of two lifts and be cruising to secluded beaches, waterfront restaurants, or some of Florida's finest fishing grounds within minutes. Dolphins, manatees, and spectacular coastal wildlife are frequent visitors, making every day feel like a vacation. Built with peace of mind in mind, the home also features a durable metal roof, impact-resistant windows, electric hurricane shutters, propane service, and a private elevator, combining comfort, accessibility, and storm-ready construction. Properties offering this level of privacy, protected harbor frontage, boating convenience, and flexible living space are exceptionally rare. Whether you're searching for a full-time residence, seasonal retreat, or waterfront legacy property, this remarkable home offers an unparalleled opportunity to embrace the very best of the Pine Island lifestyle.

8550 Ebbtide Way, Bokeelia

$784,900

Built to last and designed for the waterfront lifestyle, this custom 2018 Insulated Concrete Form (ICF) home combines exceptional strength, energy efficiency, and storm resilience with quick, deep, direct access to the Gulf of America. Offering 3 bedrooms, 2.5 baths, and quality construction rarely found on the island, this home features impact windows and doors, a standing seam metal roof, and solid ICF construction for outstanding durability and peace of mind. The elevated second-floor living area is designed to maximize breathtaking intersecting canal views and spectacular Southwest Florida sunsets. The open-concept great room flows seamlessly into the well-appointed kitchen featuring island seating, tile backsplash, stainless steel appliances, and a versatile flex space ideal for a home office, pantry, or hobby area. The primary suite offers private lanai access, a spacious en-suite bath with dual vanities, a walk-in shower with rain shower feature, and generous closet space, while a convenient half bath completes the main living level. The first floor provides two spacious guest bedrooms, a full guest bath, an in-residence laundry area, and an oversized two-car garage with a rear overhead door for easy access to your boating equipment and waterfront toys. A paver driveway offers plenty of parking for family and guests. Outside, the waterfront setting is ready for relaxing or entertaining with a patio, beach-style lounging area, freestanding hot tub, and room to add a custom pool. The 2017 seawall, composite dock, and 10,000-pound covered boat lift make getting on the water quick and effortless. From here, enjoy easy, deep-water boating with direct access to the Gulf of America, world-class fishing, nearby barrier islands, waterfront restaurants, and endless days exploring Southwest Florida by boat. Whether you're searching for a full-time residence, seasonal escape, or weekend waterfront retreat, this home delivers exceptional construction, low-maintenance living, and the boating lifestyle you've been dreaming of.

3 Beds ⋅ 3 Baths ⋅ 2026028974 MLS

Built to last and designed for the waterfront lifestyle, this custom 2018 Insulated Concrete Form (ICF) home combines exceptional strength, energy efficiency, and storm resilience with quick, deep, direct access to the Gulf of America. Offering 3 bedrooms, 2.5 baths, and quality construction rarely found on the island, this home features impact windows and doors, a standing seam metal roof, and solid ICF construction for outstanding durability and peace of mind. The elevated second-floor living area is designed to maximize breathtaking intersecting canal views and spectacular Southwest Florida sunsets. The open-concept great room flows seamlessly into the well-appointed kitchen featuring island seating, tile backsplash, stainless steel appliances, and a versatile flex space ideal for a home office, pantry, or hobby area. The primary suite offers private lanai access, a spacious en-suite bath with dual vanities, a walk-in shower with rain shower feature, and generous closet space, while a convenient half bath completes the main living level. The first floor provides two spacious guest bedrooms, a full guest bath, an in-residence laundry area, and an oversized two-car garage with a rear overhead door for easy access to your boating equipment and waterfront toys. A paver driveway offers plenty of parking for family and guests. Outside, the waterfront setting is ready for relaxing or entertaining with a patio, beach-style lounging area, freestanding hot tub, and room to add a custom pool. The 2017 seawall, composite dock, and 10,000-pound covered boat lift make getting on the water quick and effortless. From here, enjoy easy, deep-water boating with direct access to the Gulf of America, world-class fishing, nearby barrier islands, waterfront restaurants, and endless days exploring Southwest Florida by boat. Whether you're searching for a full-time residence, seasonal escape, or weekend waterfront retreat, this home delivers exceptional construction, low-maintenance living, and the boating lifestyle you've been dreaming of.

2391 Oleander Street, St James City

$659,000

This waterfront stilt home and guest house are on a big, beautiful, property with lots of lush vegetation and a pond. The main living area is upstairs and gives the feeling of living in a treehouse. The home has beautiful wood planked cathedral ceilings and wood flooring The lovely, tiled bathroom has a jetted soaking tub and multiheaded shower. The upstairs living area is surrounded by connected decks and screened patios with a large, screened area off the kitchen which is perfect for enjoying the breezes and watching the birds and wildlife around the pond. A new outdoor lift, drain field and pavers on the circular driveway all add to the value of this property. The upstairs windows are all protected by manual hurricane shutters. The 1-bedroom guest home is connected by the boardwalk, has a full bathroom and kitchen as well as its own deck for outdoor relaxation. Downstairs under the main living area is a multipurpose room that is perfect for an office, studio or extra bedroom. It has an additional full bathroom and French doors that open up to a covered deck area. There is an enclosed 1 car garage with plenty of storage and space for a workshop. This fabulous home is located at the center of Pine Island and is within easy walking distance of the public pool, playground, library, and local museum. It is just minutes from shopping, and restaurants. This fabulous home combines natural beauty with functional living spaces, making it the perfect retreat. Schedule a visit today to experience the charm and tranquility of this exceptional property!

3 Beds ⋅ 3 Baths ⋅ 2026023398 MLS

This waterfront stilt home and guest house are on a big, beautiful, property with lots of lush vegetation and a pond. The main living area is upstairs and gives the feeling of living in a treehouse. The home has beautiful wood planked cathedral ceilings and wood flooring The lovely, tiled bathroom has a jetted soaking tub and multiheaded shower. The upstairs living area is surrounded by connected decks and screened patios with a large, screened area off the kitchen which is perfect for enjoying the breezes and watching the birds and wildlife around the pond. A new outdoor lift, drain field and pavers on the circular driveway all add to the value of this property. The upstairs windows are all protected by manual hurricane shutters. The 1-bedroom guest home is connected by the boardwalk, has a full bathroom and kitchen as well as its own deck for outdoor relaxation. Downstairs under the main living area is a multipurpose room that is perfect for an office, studio or extra bedroom. It has an additional full bathroom and French doors that open up to a covered deck area. There is an enclosed 1 car garage with plenty of storage and space for a workshop. This fabulous home is located at the center of Pine Island and is within easy walking distance of the public pool, playground, library, and local museum. It is just minutes from shopping, and restaurants. This fabulous home combines natural beauty with functional living spaces, making it the perfect retreat. Schedule a visit today to experience the charm and tranquility of this exceptional property!

10545 Habitat Trail, Bokeelia

$1,700,000

Welcome to a rare direct Gulf access waterfront estate in the highly sought-after Pine Island Shores community. Perfectly positioned to capture expansive bay views and abundant marine wildlife, this property offers a front-row seat to dolphins playing, manatees gliding by, and unforgettable Southwest Florida sunsets—all from your own backyard. With no bridges to open water, you’ll enjoy effortless access to Pine Island Sound and the Gulf of Mexico. This spacious 2-story coastal retreat features 3 bedrooms + den and 3 bathrooms, designed with a bright open floor plan, cathedral ceilings, and large windows that showcase the stunning waterfront setting throughout the home. The outdoor living experience is truly exceptional. Relax or entertain around your private saltwater pool and spa, expansive patio, gazebo, and multiple balconies are all perfectly oriented to take in the sweeping bay views and coastal breezes. Boating enthusiasts will appreciate the private dock with lift, water, and electric, making it easy to spend your days on the water. Inside, the home offers a well-appointed kitchen with ample cabinetry and eat-in space, a generous primary suite with dual sinks and separate tub and shower, and flexible living areas including a den/home office. Additional highlights include a metal roof, electric storm shutters, fireplace, surround sound wiring, and abundant storage throughout. Located in a gated boating community, this property combines privacy, space, and a true connection to the water. Whether you’re looking for a full-time residence, seasonal retreat, or luxury waterfront escape—this is Pine Island living at its finest.

3 Beds ⋅ 3 Baths ⋅ 2026020265 MLS

Welcome to a rare direct Gulf access waterfront estate in the highly sought-after Pine Island Shores community. Perfectly positioned to capture expansive bay views and abundant marine wildlife, this property offers a front-row seat to dolphins playing, manatees gliding by, and unforgettable Southwest Florida sunsets—all from your own backyard. With no bridges to open water, you’ll enjoy effortless access to Pine Island Sound and the Gulf of Mexico. This spacious 2-story coastal retreat features 3 bedrooms + den and 3 bathrooms, designed with a bright open floor plan, cathedral ceilings, and large windows that showcase the stunning waterfront setting throughout the home. The outdoor living experience is truly exceptional. Relax or entertain around your private saltwater pool and spa, expansive patio, gazebo, and multiple balconies are all perfectly oriented to take in the sweeping bay views and coastal breezes. Boating enthusiasts will appreciate the private dock with lift, water, and electric, making it easy to spend your days on the water. Inside, the home offers a well-appointed kitchen with ample cabinetry and eat-in space, a generous primary suite with dual sinks and separate tub and shower, and flexible living areas including a den/home office. Additional highlights include a metal roof, electric storm shutters, fireplace, surround sound wiring, and abundant storage throughout. Located in a gated boating community, this property combines privacy, space, and a true connection to the water. Whether you’re looking for a full-time residence, seasonal retreat, or luxury waterfront escape—this is Pine Island living at its finest.

2096 Macadamia Street, St James City

$524,500

Welcome to this beautifully maintained and move-in-ready home that perfectly blends comfort, style, and convenience. Nestled in the private community of Isle of Pines, this property offers an inviting open-concept layout filled with natural light, ideal for both everyday living and entertaining. The spacious kitchen features modern appliances, a gas stove, ample cabinetry, two pantries and a generous island that flows seamlessly into the living and dining areas. The oversized primary suite provides a relaxing retreat with a well-appointed en-suite complete with soaking tub, a large tiled shower, his and hers walk-in closets and sliding doors to a private lanai. Two additional bedrooms are perfect for guests, each with their own en suite and large closets. Step outside to enjoy the heated pool and private clubhouse with pool table, and a bonus guest apartment for overflow company. This community has a private waste water system, so you’ll never have to worry about a septic. With thoughtful upgrades throughout, and pride of ownership evident in every detail, this home truly stands out. Walk to nearby Pineland Marina and Alden Pines Golf Course, or enjoy a five star dinner at the world renowned Tarpon Lodge, right in your back yard! A brand new outdoor lift and maintenance free landscaping complete this beautiful property .This home sustained no damage or flooding from any of the recent storms. Don’t miss your opportunity to make this exceptional island home your own—schedule your showing today! Motivated Seller!! New asking price Now $524500

3 Beds ⋅ 3 Baths ⋅ 226014250 MLS

Welcome to this beautifully maintained and move-in-ready home that perfectly blends comfort, style, and convenience. Nestled in the private community of Isle of Pines, this property offers an inviting open-concept layout filled with natural light, ideal for both everyday living and entertaining. The spacious kitchen features modern appliances, a gas stove, ample cabinetry, two pantries and a generous island that flows seamlessly into the living and dining areas. The oversized primary suite provides a relaxing retreat with a well-appointed en-suite complete with soaking tub, a large tiled shower, his and hers walk-in closets and sliding doors to a private lanai. Two additional bedrooms are perfect for guests, each with their own en suite and large closets. Step outside to enjoy the heated pool and private clubhouse with pool table, and a bonus guest apartment for overflow company. This community has a private waste water system, so you’ll never have to worry about a septic. With thoughtful upgrades throughout, and pride of ownership evident in every detail, this home truly stands out. Walk to nearby Pineland Marina and Alden Pines Golf Course, or enjoy a five star dinner at the world renowned Tarpon Lodge, right in your back yard! A brand new outdoor lift and maintenance free landscaping complete this beautiful property .This home sustained no damage or flooding from any of the recent storms. Don’t miss your opportunity to make this exceptional island home your own—schedule your showing today! Motivated Seller!! New asking price Now $524500

7655 Myrsine Circle, Bokeelia

$345,000

Stilt home on an oversized lot in Saint James City! Has a closed in garage and workshop downstairs with additional room for guests. This property offers a quiet island retreat with all the convenience for waterfront living. Boating enthusiasts will love this location in Tropical Point! The home is just a few minutes’ walking distance from Tropical Point Park water access, perfect for kayaking and boating, which also provides easy access to explore the surrounding islands, some of the best fishing just right down the road. The home features a NEW metal roof, and a recently updated (UP-2-CODE) Electrical panel, and is ready for you to make it your own!!

2 Beds ⋅ 3 Baths ⋅ 2026010703 MLS

Stilt home on an oversized lot in Saint James City! Has a closed in garage and workshop downstairs with additional room for guests. This property offers a quiet island retreat with all the convenience for waterfront living. Boating enthusiasts will love this location in Tropical Point! The home is just a few minutes’ walking distance from Tropical Point Park water access, perfect for kayaking and boating, which also provides easy access to explore the surrounding islands, some of the best fishing just right down the road. The home features a NEW metal roof, and a recently updated (UP-2-CODE) Electrical panel, and is ready for you to make it your own!!

3660 Tropical Point Drive, St James City

$975,000

Experience true coastal luxury in this beautifully remodeled 3BD/3BA waterfront retreat in Saint James City with direct Gulf access—no bridges. Located just north of the Sanibel Causeway, this elevated oasis offers 2,383 sqft of open living, soaring ceilings, & 5 sets of impact sliding doors for seamless indoor-outdoor flow. The east-facing lanai features a heated pool, large screened cage, & full outdoor kitchen w/quartz island, grill, bar fridge & burners --perfect for shaded afternoons & evening entertaining. Inside, enjoy two primary suites (1 up,1 down), an additional bedroom, plus a loft & private balcony. All 3 spa-inspired baths feature rainfall showers, a freestanding tub & designer finishes. Smart home features include Samsung Bespoke washer/dryer, 4-door Flex fridge, Ring, Nest, & more. Built on 10-ft elevation, no flood issues, with impact windows/doors, 2023 roof, new garage door, composite dock (2021), plantation shutters, Minka Aire fans, custom closet systems & lush tropical landscaping w/lighting & irrigation. This home is your private boating paradise! Move-in ready & unforgettable.

3 Beds ⋅ 3 Baths ⋅ 2025002846 MLS

Experience true coastal luxury in this beautifully remodeled 3BD/3BA waterfront retreat in Saint James City with direct Gulf access—no bridges. Located just north of the Sanibel Causeway, this elevated oasis offers 2,383 sqft of open living, soaring ceilings, & 5 sets of impact sliding doors for seamless indoor-outdoor flow. The east-facing lanai features a heated pool, large screened cage, & full outdoor kitchen w/quartz island, grill, bar fridge & burners --perfect for shaded afternoons & evening entertaining. Inside, enjoy two primary suites (1 up,1 down), an additional bedroom, plus a loft & private balcony. All 3 spa-inspired baths feature rainfall showers, a freestanding tub & designer finishes. Smart home features include Samsung Bespoke washer/dryer, 4-door Flex fridge, Ring, Nest, & more. Built on 10-ft elevation, no flood issues, with impact windows/doors, 2023 roof, new garage door, composite dock (2021), plantation shutters, Minka Aire fans, custom closet systems & lush tropical landscaping w/lighting & irrigation. This home is your private boating paradise! Move-in ready & unforgettable.

2372 Cherimoya Lane, St James City

$1,470,000

Beautiful home south end of the island! Poured concrete construction, a metal roof , minutes to Sanibel beachs , ADA Accessible home* Sunrise and Sunset views , fire sprinkler system *Elevator- #900 capacity Impact resistant doors & windows. *1000 sq ft of 'man cave' next to the garage + apartment w/ bedroom & kitchen *Each level has a bedroom suite. Top floor master suite- best views on the island- kitchenette, walk-in shower, soaking tub. Main level, 2nd floor- outdoor gas grill hook up, fireplace, plantation shutters, the kitchen: double oven & gas range. Pool & HotTub: Heated/saltwater/self cleaning. One of the most well built homes in SWFL.. Generator hook ups. Deep canal direct access to the gulf. Covered 10000 lb boat lift & jet ski lift on dock. Every room has waterviews! St. James City has bars, restaurants, seafood markets, farm fresh markets, fishing & access to the best beaches minutes away!

3 Beds ⋅ 3 Baths ⋅ 2025000268 MLS

Beautiful home south end of the island! Poured concrete construction, a metal roof , minutes to Sanibel beachs , ADA Accessible home* Sunrise and Sunset views , fire sprinkler system *Elevator- #900 capacity Impact resistant doors & windows. *1000 sq ft of 'man cave' next to the garage + apartment w/ bedroom & kitchen *Each level has a bedroom suite. Top floor master suite- best views on the island- kitchenette, walk-in shower, soaking tub. Main level, 2nd floor- outdoor gas grill hook up, fireplace, plantation shutters, the kitchen: double oven & gas range. Pool & HotTub: Heated/saltwater/self cleaning. One of the most well built homes in SWFL.. Generator hook ups. Deep canal direct access to the gulf. Covered 10000 lb boat lift & jet ski lift on dock. Every room has waterviews! St. James City has bars, restaurants, seafood markets, farm fresh markets, fishing & access to the best beaches minutes away!

3430 1st Avenue, St James City

$335,000

Charming Pine Island Stilt Home with Attached Apartment – Ideal for Bed & Breakfast or Airbnb Ventures! This distinctive Pine Island property – a rare find among stilt homes with a fully permitted lower level, adding valuable space and versatility. This beautifully remodeled home offers over 1,600 sq. ft. of modern living, with stylish updates throughout, making it perfect as an investment opportunity or a spacious family retreat. With new roof, New mini split AC, New tankless water heater, 2 New Kitchens and 3 New Bathrooms - This property is ready for you to move in and experience the best of Pine Island living. Don’t miss the chance to own a versatile, income-generating home in one of Florida’s most unique coastal communities. Seller is offering $5000 towards concessions.

3 Beds ⋅ 3 Baths ⋅ 225014802 MLS

Charming Pine Island Stilt Home with Attached Apartment – Ideal for Bed & Breakfast or Airbnb Ventures! This distinctive Pine Island property – a rare find among stilt homes with a fully permitted lower level, adding valuable space and versatility. This beautifully remodeled home offers over 1,600 sq. ft. of modern living, with stylish updates throughout, making it perfect as an investment opportunity or a spacious family retreat. With new roof, New mini split AC, New tankless water heater, 2 New Kitchens and 3 New Bathrooms - This property is ready for you to move in and experience the best of Pine Island living. Don’t miss the chance to own a versatile, income-generating home in one of Florida’s most unique coastal communities. Seller is offering $5000 towards concessions.

10925 Russell Road, Bokeelia