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Home Located in St. James with Smithtown Schools and close to town. This Ranch has 3 Bedrooms, 3 Full Baths, potential M/D set-up with OSE for extended Family. Home Features 2-Car Detached Garage, Flat .25acre of property with Fenced Yard for Kids or Pets to enjoy. Gas Heat, Large EIK with Gas Cooking, Hardwood Floors, Brand New Roof less than 1 Year, Fireplace in Living Room, Den with wall of windows overlooking the Yard, Patio in backyard, In-Ground Sprinklers and More. Want to live in the Heart of St. James close to town then view this home.

3 Beds ⋅ 3 Baths ⋅ 983758 MLS

Home Located in St. James with Smithtown Schools and close to town. This Ranch has 3 Bedrooms, 3 Full Baths, potential M/D set-up with OSE for extended Family. Home Features 2-Car Detached Garage, Flat .25acre of property with Fenced Yard for Kids or Pets to enjoy. Gas Heat, Large EIK with Gas Cooking, Hardwood Floors, Brand New Roof less than 1 Year, Fireplace in Living Room, Den with wall of windows overlooking the Yard, Patio in backyard, In-Ground Sprinklers and More. Want to live in the Heart of St. James close to town then view this home.

229 4th Street, Saint James

$690,000

Welcome Home! This charming ranch is perfectly situated in the heart of St. James and offers the ease of one-level living. Featuring 3 bedrooms and 1 full bathroom, the home boasts a welcoming living room with a wood-burning fireplace, a dining area, and an updated kitchen with granite countertops. Additional highlights include vaulted ceilings with skylights, hardwood floors throughout, Andersen windows, 200-amp electrical service, a welcoming front porch, and a full unfinished basement with outside entrance (OSE) offering endless possibilities for additional living space, recreation, or storage. Set on a beautiful, fully fenced corner lot, the backyard is perfect for entertaining with a maintenance-free composite deck and plenty of outdoor space to enjoy. Conveniently located just 0.07 miles from the LIRR and moments from St. James Village, local beaches, Smith Haven Mall, shopping, dining, and major roadways. Located within the Smithtown Central School District, serving St. James Elementary School, Nesaquake Middle School, and Smithtown High School East. Photos have been digitally edited. If you're looking for a ranch offering comfort, convenience, and easy living, look no further—this is the one you've been waiting for!

3 Beds ⋅ 1 Baths ⋅ 1018871 MLS

Welcome Home! This charming ranch is perfectly situated in the heart of St. James and offers the ease of one-level living. Featuring 3 bedrooms and 1 full bathroom, the home boasts a welcoming living room with a wood-burning fireplace, a dining area, and an updated kitchen with granite countertops. Additional highlights include vaulted ceilings with skylights, hardwood floors throughout, Andersen windows, 200-amp electrical service, a welcoming front porch, and a full unfinished basement with outside entrance (OSE) offering endless possibilities for additional living space, recreation, or storage. Set on a beautiful, fully fenced corner lot, the backyard is perfect for entertaining with a maintenance-free composite deck and plenty of outdoor space to enjoy. Conveniently located just 0.07 miles from the LIRR and moments from St. James Village, local beaches, Smith Haven Mall, shopping, dining, and major roadways. Located within the Smithtown Central School District, serving St. James Elementary School, Nesaquake Middle School, and Smithtown High School East. Photos have been digitally edited. If you're looking for a ranch offering comfort, convenience, and easy living, look no further—this is the one you've been waiting for!

265 Sixth Avenue, Saint James

$685,000

Welcome to 287 Sixth Avenue — a beautifully maintained ranch in the heart of St. James, offering the perfect blend of comfort, convenience, and untapped potential! This 3-bedroom, 1.5-bath home sits on a generous quarter-acre lot and features classic hardwood floors throughout as well as a 200-amp electrical system and central air. The layout offers effortless single-level living, making it an ideal option for first-time buyers, downsizers, or anyone seeking simplicity without compromise. A large garage adds both convenience and storage, and the yard has room to entertain. The home’s full, unfinished basement provides approximately 800 square feet of additional space — a blank canvas ready to be transformed into a home gym, media room, office, or extended living area tailored to your lifestyle. Located within the highly regarded Smithtown School District, this home also delivers exceptional proximity to everything you need. Just minutes away, you’ll find the vibrant shops and restaurants along Lake Ave, as well as major retail destinations like Smith Haven Mall, Whole Foods, and Trader Joe’s, and much more, making everyday errands and weekend outings limitless. For commuters, the nearby St. James train station offers convenient access to New York City. And for those who value coastal living, you’re just a short 10-minute drive to some of Long Island’s beautiful North Shore beaches. Whether you’re looking to move right in or create your dream space over time, this is an excellent opportunity to own a home in one of Long Island’s most desirable communities.

3 Beds ⋅ 2 Baths ⋅ 984041 MLS

Welcome to 287 Sixth Avenue — a beautifully maintained ranch in the heart of St. James, offering the perfect blend of comfort, convenience, and untapped potential! This 3-bedroom, 1.5-bath home sits on a generous quarter-acre lot and features classic hardwood floors throughout as well as a 200-amp electrical system and central air. The layout offers effortless single-level living, making it an ideal option for first-time buyers, downsizers, or anyone seeking simplicity without compromise. A large garage adds both convenience and storage, and the yard has room to entertain. The home’s full, unfinished basement provides approximately 800 square feet of additional space — a blank canvas ready to be transformed into a home gym, media room, office, or extended living area tailored to your lifestyle. Located within the highly regarded Smithtown School District, this home also delivers exceptional proximity to everything you need. Just minutes away, you’ll find the vibrant shops and restaurants along Lake Ave, as well as major retail destinations like Smith Haven Mall, Whole Foods, and Trader Joe’s, and much more, making everyday errands and weekend outings limitless. For commuters, the nearby St. James train station offers convenient access to New York City. And for those who value coastal living, you’re just a short 10-minute drive to some of Long Island’s beautiful North Shore beaches. Whether you’re looking to move right in or create your dream space over time, this is an excellent opportunity to own a home in one of Long Island’s most desirable communities.

287 6th Avenue, Saint James

$680,500

Welcome to 3 Bayberry Drive in the heart of Saint James! This beautifully updated home has been renovated from top to bottom within the last six years and offers the perfect blend of style, comfort, and functionality. The stunning kitchen, renovated in 2022, features quartz countertops, stainless steel appliances, custom tile backsplash, recessed lighting, glass display cabinetry, and thoughtful designer finishes throughout. The main bathroom was also completely updated in 2022. There is a full basement with an outside entrance. For added convenience, washer and dryer hookups are available on both the main level and in the basement. Additional updates include beautifully refinished hardwood floors on the main level (2022), central air conditioning on the main floor, and ductless split units in the basement for year-round comfort. Step outside to enjoy the private backyard retreat featuring a spacious deck leading to a large patio—perfect for entertaining guests, outdoor dining, or simply relaxing after a long day. Nestled in a picturesque, storybook neighborhood, this home offers a prime Saint James location close to everything the community has to offer. With countless updates and amenities throughout, this is truly a home that must be seen to be appreciated. Schedule your private showing today before this exceptional opportunity is gone!

3 Beds ⋅ 2 Baths ⋅ 1006934 MLS

Welcome to 3 Bayberry Drive in the heart of Saint James! This beautifully updated home has been renovated from top to bottom within the last six years and offers the perfect blend of style, comfort, and functionality. The stunning kitchen, renovated in 2022, features quartz countertops, stainless steel appliances, custom tile backsplash, recessed lighting, glass display cabinetry, and thoughtful designer finishes throughout. The main bathroom was also completely updated in 2022. There is a full basement with an outside entrance. For added convenience, washer and dryer hookups are available on both the main level and in the basement. Additional updates include beautifully refinished hardwood floors on the main level (2022), central air conditioning on the main floor, and ductless split units in the basement for year-round comfort. Step outside to enjoy the private backyard retreat featuring a spacious deck leading to a large patio—perfect for entertaining guests, outdoor dining, or simply relaxing after a long day. Nestled in a picturesque, storybook neighborhood, this home offers a prime Saint James location close to everything the community has to offer. With countless updates and amenities throughout, this is truly a home that must be seen to be appreciated. Schedule your private showing today before this exceptional opportunity is gone!

3 Bayberry Drive, Saint James

$675,000

Welcome to this well-maintained 3 bedroom, 2 full bath ranch offering comfort, convenience and endless potential. Featuring hardwood floors throughout and central vac, this home boasts a warm and inviting layout perfect for everyday living. Enjoy your morning coffee on the charming front porch, or take advantage of the spacious interior ready for your personal touch. The large basement offers incredible versatility, complete with a full bath and finished rooms-ideal for extended living, a home office or recreation space. Conveniently located close to town, shopping, and dining, this home is a fantastic opportunity to make it your own. Don’t miss out on this one!

3 Beds ⋅ 3 Baths ⋅ 983666 MLS

Welcome to this well-maintained 3 bedroom, 2 full bath ranch offering comfort, convenience and endless potential. Featuring hardwood floors throughout and central vac, this home boasts a warm and inviting layout perfect for everyday living. Enjoy your morning coffee on the charming front porch, or take advantage of the spacious interior ready for your personal touch. The large basement offers incredible versatility, complete with a full bath and finished rooms-ideal for extended living, a home office or recreation space. Conveniently located close to town, shopping, and dining, this home is a fantastic opportunity to make it your own. Don’t miss out on this one!

307 6th Avenue, Saint James

$670,000

This Colonial home features three bedrooms, 2 1/2 baths, eat in kitchen, formal dining room, large living room, family room with fireplace, basement, two car garage, large fenced yard - on a Dead End Street!

3 Beds ⋅ 3 Baths ⋅ 997288 MLS

This Colonial home features three bedrooms, 2 1/2 baths, eat in kitchen, formal dining room, large living room, family room with fireplace, basement, two car garage, large fenced yard - on a Dead End Street!

43 Vanderbilt Avenue, Saint James

$665,000

Welcome to this diamond "Ranch Model" located in the desirable 55+ community of Saint James. This spacious ranch w/ garage has been totally updated! Features include.....An EIK w/ granite counter tops, and updated appliances, Dining room, large living room w/ 10 ft ceilings and french doors to an extended new patio, primary ensuite w/ accessible roll-in shower, a spacious 2nd bedroom or den, and an additional updated full bathroom, All Updated windows Doors and wood vinyl flooring throughout-Also Handicap Accessible! Country Club living at its best... amenities include a beautiful clubhouse, tennis courts, pickle ball, indoor and 2 outdoor swimming pools, nature trails, buses provided weekly for shopping and lots of clubs to join!

2 Beds ⋅ 2 Baths ⋅ 1008586 MLS

Welcome to this diamond "Ranch Model" located in the desirable 55+ community of Saint James. This spacious ranch w/ garage has been totally updated! Features include.....An EIK w/ granite counter tops, and updated appliances, Dining room, large living room w/ 10 ft ceilings and french doors to an extended new patio, primary ensuite w/ accessible roll-in shower, a spacious 2nd bedroom or den, and an additional updated full bathroom, All Updated windows Doors and wood vinyl flooring throughout-Also Handicap Accessible! Country Club living at its best... amenities include a beautiful clubhouse, tennis courts, pickle ball, indoor and 2 outdoor swimming pools, nature trails, buses provided weekly for shopping and lots of clubs to join!

1003 Gotham Drive, Saint James

$665,000

Possible Mother Daughter with proper permits! The home is a split level with three bedrooms up and bath*main level has a large sunny living room, dining room and kitchen with energy star appliances and an office/studio apartment. There is a basement for great storage with new boiler and hot water heater. There is an oversized two car garage and a beautiful large yard with a new deck off the sliders of the dining room. Endless Possibilites!

4 Beds ⋅ 3 Baths ⋅ 988297 MLS

Possible Mother Daughter with proper permits! The home is a split level with three bedrooms up and bath*main level has a large sunny living room, dining room and kitchen with energy star appliances and an office/studio apartment. There is a basement for great storage with new boiler and hot water heater. There is an oversized two car garage and a beautiful large yard with a new deck off the sliders of the dining room. Endless Possibilites!

67 Cleremont Avenue, Saint James

$655,000

Welcome to 7 Applewood Road located in the Smithtown School District. This lovely Ranch style home features a spacious eat-in-kitchen with newer appliances and a bay window, living room with a sunny bow window, family room with a wood burning fireplace which leads you into a beautiful four season sun room, a sizable primary bedroom with his/her closets, 2nd bedroom with double closet, 3rd bedroom with a nice size closet, updated full bathroom, hardwood floors, 2014 CAC, Gas heating and cooking, 40 gal. hot water heater, forced hot air heat, appropriate outlet for portable generator, 6 zone sprinkler system, 2015 roof, very sunny .25 acre fully fenced, full basement with newer washer only & dryer, partially finished. This property incorporates peaceful suburban living with easy access to everything North Shore has to offer. There is a lovely park right down the road and playground. Visit down town St. James for a wonderful experience shopping, dining, parks and major roadways, easy access to the Smith Haven Mall. A stones throw away from the beautiful villages of Port Jefferson and Stony Brook. Come and have an ice cream cone down by the Harbor or shop til you drop! Enjoy the summertime concert and all events all year long! Close to public transportation, LIRR, Port Jefferson Ferry to Bridgeport CT, Long Island Expressway, along with Northern State Parkway. Taxes: $12,285.59 - Star Deduction $877.00

3 Beds ⋅ 1 Baths ⋅ 990572 MLS

Welcome to 7 Applewood Road located in the Smithtown School District. This lovely Ranch style home features a spacious eat-in-kitchen with newer appliances and a bay window, living room with a sunny bow window, family room with a wood burning fireplace which leads you into a beautiful four season sun room, a sizable primary bedroom with his/her closets, 2nd bedroom with double closet, 3rd bedroom with a nice size closet, updated full bathroom, hardwood floors, 2014 CAC, Gas heating and cooking, 40 gal. hot water heater, forced hot air heat, appropriate outlet for portable generator, 6 zone sprinkler system, 2015 roof, very sunny .25 acre fully fenced, full basement with newer washer only & dryer, partially finished. This property incorporates peaceful suburban living with easy access to everything North Shore has to offer. There is a lovely park right down the road and playground. Visit down town St. James for a wonderful experience shopping, dining, parks and major roadways, easy access to the Smith Haven Mall. A stones throw away from the beautiful villages of Port Jefferson and Stony Brook. Come and have an ice cream cone down by the Harbor or shop til you drop! Enjoy the summertime concert and all events all year long! Close to public transportation, LIRR, Port Jefferson Ferry to Bridgeport CT, Long Island Expressway, along with Northern State Parkway. Taxes: $12,285.59 - Star Deduction $877.00

7 Applewood Road, Saint James

$649,700

Welcome to 259 Woodlawn Avenue in the heart of St. James. This well-maintained and tastefully updated Cape offers 3 bedrooms, 1.5 bathrooms, and a move-in ready interior filled with warmth and character. The open kitchen features granite countertops and flows seamlessly into the main living areas, while updated bathrooms and newer vinyl flooring add modern comfort throughout. Major improvements include a newer boiler, oil tank, hot water heater, updated electric service, younger vinyl replacement windows, and a new composite rear deck. Situated on a flat, fully fenced quarter-acre property with young vinyl fencing, the backyard provides plenty of space for entertaining, gardening, pets, or play. Set back with driveway access from 7th Avenue, the property enjoys a surprisingly private feel while remaining convenient to shopping, restaurants, parks, and transportation. Combining the charm of an older home with the peace of mind of numerous updates, this meticulously maintained residence is ready for its next owner to move right in and enjoy.

3 Beds ⋅ 2 Baths ⋅ 1016001 MLS

Welcome to 259 Woodlawn Avenue in the heart of St. James. This well-maintained and tastefully updated Cape offers 3 bedrooms, 1.5 bathrooms, and a move-in ready interior filled with warmth and character. The open kitchen features granite countertops and flows seamlessly into the main living areas, while updated bathrooms and newer vinyl flooring add modern comfort throughout. Major improvements include a newer boiler, oil tank, hot water heater, updated electric service, younger vinyl replacement windows, and a new composite rear deck. Situated on a flat, fully fenced quarter-acre property with young vinyl fencing, the backyard provides plenty of space for entertaining, gardening, pets, or play. Set back with driveway access from 7th Avenue, the property enjoys a surprisingly private feel while remaining convenient to shopping, restaurants, parks, and transportation. Combining the charm of an older home with the peace of mind of numerous updates, this meticulously maintained residence is ready for its next owner to move right in and enjoy.

259 Woodlawn Avenue, Saint James

$645,000

Welcome to this beautifully maintained home nestled on ashy 1/2 acre in the heart of Saint James, offering a perfect blend of comfort, and curb appeal: This home features a stucco exterior and an inviting presence, highlighted by a circular driveway that provides both convenience and elegance. Step inside to discover a spacious layout with radiant heated floors throughout, delivering year-round comfort and efficiency. The interior offers bright, sun-filled living spaces, well-proportioned bedrooms, and a functional layout ideal for both everyday living and entertaining. The home is equipped with 200-amp electric service, supporting modern living with ease. Out back, you’ll find a new 2-car detached garage (approx. 3 years old) with a loft/bonus space, perfect for storage, a workshop, or potential creative use. The private yard offers plenty of space for outdoor enjoyment, gatherings, or future enhancements. Conveniently located near shopping, dining, parks, and major roadways, this property combines peaceful suburban living with easy access to everything the North Shore has to offer. A move-in ready home with valuable upgrades—don’t miss this opportunity.

3 Beds ⋅ 1 Baths ⋅ 985300 MLS

Welcome to this beautifully maintained home nestled on ashy 1/2 acre in the heart of Saint James, offering a perfect blend of comfort, and curb appeal: This home features a stucco exterior and an inviting presence, highlighted by a circular driveway that provides both convenience and elegance. Step inside to discover a spacious layout with radiant heated floors throughout, delivering year-round comfort and efficiency. The interior offers bright, sun-filled living spaces, well-proportioned bedrooms, and a functional layout ideal for both everyday living and entertaining. The home is equipped with 200-amp electric service, supporting modern living with ease. Out back, you’ll find a new 2-car detached garage (approx. 3 years old) with a loft/bonus space, perfect for storage, a workshop, or potential creative use. The private yard offers plenty of space for outdoor enjoyment, gatherings, or future enhancements. Conveniently located near shopping, dining, parks, and major roadways, this property combines peaceful suburban living with easy access to everything the North Shore has to offer. A move-in ready home with valuable upgrades—don’t miss this opportunity.

276 Woodlawn Avenue, Saint James

$625,000

Welcome to this charming 3-bedroom, 1 1/2-bath ranch perfectly situated on a spacious corner lot in the heart of highly desirable St. James and located within the acclaimed Smithtown Central School District. With inventory in St. James remaining extremely limited, this is an exceptional opportunity to own in one of Long Island’s most sought-after communities. Lovingly maintained over the years, this home offers the perfect blend of comfort, character, and endless potential to make it truly your own. Features include a functional ranch-style layout, 1-car garage, partial basement ideal for storage or future possibilities, and in-ground sprinklers for easy lawn maintenance. Step outside to enjoy the expansive yard — perfect for entertaining, gardening, outdoor gatherings, or simply relaxing in your own private retreat. Conveniently located near shopping, restaurants, parks, schools, and all local amenities, this home offers both tranquility and convenience in an unbeatable location. Whether you’re looking to settle into St. James for the first time, downsize, or create your dream home, this is an opportunity you won’t want to miss.

3 Beds ⋅ 2 Baths ⋅ 999669 MLS

Welcome to this charming 3-bedroom, 1 1/2-bath ranch perfectly situated on a spacious corner lot in the heart of highly desirable St. James and located within the acclaimed Smithtown Central School District. With inventory in St. James remaining extremely limited, this is an exceptional opportunity to own in one of Long Island’s most sought-after communities. Lovingly maintained over the years, this home offers the perfect blend of comfort, character, and endless potential to make it truly your own. Features include a functional ranch-style layout, 1-car garage, partial basement ideal for storage or future possibilities, and in-ground sprinklers for easy lawn maintenance. Step outside to enjoy the expansive yard — perfect for entertaining, gardening, outdoor gatherings, or simply relaxing in your own private retreat. Conveniently located near shopping, restaurants, parks, schools, and all local amenities, this home offers both tranquility and convenience in an unbeatable location. Whether you’re looking to settle into St. James for the first time, downsize, or create your dream home, this is an opportunity you won’t want to miss.

270 7th Street, Saint James

$599,000

Rare End-Unit Ranch with Garage in the Desirable 55+ Community of Fairfield at St. James! This move-in-ready home offers comfortable and convenient living with a formal dining room and a spacious living room featuring sliders to the rear patio, where you can enjoy lush landscaped grounds, sunny southern exposure, and beautiful cherry trees! The updated kitchen features Silestone countertops, wood cabinetry, and a tile backsplash. Down the hallway, you’ll find a pantry/utility closet, updated full bathroom, and two generously sized bedrooms, including a primary en-suite, both with California Closet systems. The home is equipped with York central air conditioning and electric baseboard heating for year-round comfort. Additional updates include an updated electric panel, new carpeting, new vinyl flooring, a new dishwasher, and a new storm door. Residents enjoy outstanding amenities, including a clubhouse, indoor pool, two outdoor pools, fitness center, library, billiards, tennis, bocce, pickleball, and scenic walking trails.

2 Beds ⋅ 2 Baths ⋅ 968859 MLS

Rare End-Unit Ranch with Garage in the Desirable 55+ Community of Fairfield at St. James! This move-in-ready home offers comfortable and convenient living with a formal dining room and a spacious living room featuring sliders to the rear patio, where you can enjoy lush landscaped grounds, sunny southern exposure, and beautiful cherry trees! The updated kitchen features Silestone countertops, wood cabinetry, and a tile backsplash. Down the hallway, you’ll find a pantry/utility closet, updated full bathroom, and two generously sized bedrooms, including a primary en-suite, both with California Closet systems. The home is equipped with York central air conditioning and electric baseboard heating for year-round comfort. Additional updates include an updated electric panel, new carpeting, new vinyl flooring, a new dishwasher, and a new storm door. Residents enjoy outstanding amenities, including a clubhouse, indoor pool, two outdoor pools, fitness center, library, billiards, tennis, bocce, pickleball, and scenic walking trails.

908 Drew Lane, Saint James

$575,000

Charming 2-bedroom, 1-bath home in Saint James set on a 0.34-acre lot. Hardwood floors throughout, gas heating and cooking, and three ductless mini-split units for supplemental heating and air conditioning. Basement provides ample storage and includes a new washer and dryer and a newly added outside entrance. Updated 200-amp electrical service. Detached garage and fully fenced yard. Beautiful large property with new extensive pavers in both the front and back yards. Low annual taxes of $5,277. Great opportunity to own in a desirable neighborhood, won't last!

2 Beds ⋅ 1 Baths ⋅ 983480 MLS

Charming 2-bedroom, 1-bath home in Saint James set on a 0.34-acre lot. Hardwood floors throughout, gas heating and cooking, and three ductless mini-split units for supplemental heating and air conditioning. Basement provides ample storage and includes a new washer and dryer and a newly added outside entrance. Updated 200-amp electrical service. Detached garage and fully fenced yard. Beautiful large property with new extensive pavers in both the front and back yards. Low annual taxes of $5,277. Great opportunity to own in a desirable neighborhood, won't last!

183 Lake Avenue, Saint James

$560,000

Welcome to easy living in this beautiful 3-bedroom, 2.5-bath condo located in the 55+ Fairfield at St. James sought-after community. This bright and spacious home features an updated kitchen, a mix of wood and carpeted flooring, and newer rear sliding door that fills the home with natural light. The home offers central A/C, many closets including walk-in closets, recessed lighting, and ceiling fans, providing both comfort and functionality. Step out back to your private patio and enjoy a beautiful, peaceful, picturesque views, perfect for relaxing with morning coffee. Additional storage area located outside. This desirable 55+ gated community offers many enjoyable activities; including both an indoor pool with spa and outdoor pool, tennis, pickle ball, recreation room and more. A perfect combination of comfort, style, and low-maintenance living in a welcoming community.

3 Beds ⋅ 3 Baths ⋅ 970144 MLS

Welcome to easy living in this beautiful 3-bedroom, 2.5-bath condo located in the 55+ Fairfield at St. James sought-after community. This bright and spacious home features an updated kitchen, a mix of wood and carpeted flooring, and newer rear sliding door that fills the home with natural light. The home offers central A/C, many closets including walk-in closets, recessed lighting, and ceiling fans, providing both comfort and functionality. Step out back to your private patio and enjoy a beautiful, peaceful, picturesque views, perfect for relaxing with morning coffee. Additional storage area located outside. This desirable 55+ gated community offers many enjoyable activities; including both an indoor pool with spa and outdoor pool, tennis, pickle ball, recreation room and more. A perfect combination of comfort, style, and low-maintenance living in a welcoming community.

506 Drew Drive, Saint James

$550,000

Welcome to 102 Gotham Way in a desirable 55+ community. This beautifully maintained home offers easy, low-maintenance living with a bright, open layout designed for comfort and everyday enjoyment. The main level features a spacious primary en suite, providing convenience and privacy, along with generous living and dining areas perfect for entertaining or relaxing. Large windows fill the home with natural light, creating a warm and inviting atmosphere throughout. Enjoy a vibrant active-adult lifestyle with access to community amenities, social activities, and beautifully landscaped grounds. Conveniently located near shopping, dining, parks, and major roadways, this home offers the perfect balance of peaceful community living and neighborhood convenience. A wonderful opportunity to enjoy carefree living in a sought-after location.

3 Beds ⋅ 3 Baths ⋅ 901666 MLS

Welcome to 102 Gotham Way in a desirable 55+ community. This beautifully maintained home offers easy, low-maintenance living with a bright, open layout designed for comfort and everyday enjoyment. The main level features a spacious primary en suite, providing convenience and privacy, along with generous living and dining areas perfect for entertaining or relaxing. Large windows fill the home with natural light, creating a warm and inviting atmosphere throughout. Enjoy a vibrant active-adult lifestyle with access to community amenities, social activities, and beautifully landscaped grounds. Conveniently located near shopping, dining, parks, and major roadways, this home offers the perfect balance of peaceful community living and neighborhood convenience. A wonderful opportunity to enjoy carefree living in a sought-after location.

102 Gotham Way, Saint James

$542,200

Charming, warm and truly one of a kind, this very special storybook cottage is rich in character and classic, timeless details with a top, top location in North Saint James & nestled on the cusp of sought after Head Of The Harbor, close to the Saint James General Store, Route 25A Shopping, Schools, Stony Brook Village & just a short drive to Port Jefferson Village! Perfect as a year round home (with room for expansion) or a wonderful charming second home/summer getaway...The home offers two well sized bedrooms, immaculate full bathroom, a large great room (living room & dining room) with a striking stone fireplace taking center stage, beautifully framed by two stunning trapezoid shaped stained-glass windows that flood the space with warmth. Custom cabinetry & original details throughout including a hand carved front door, built in corner cabinet in the dining room (crafted by the homeowner), a cabinet lined kitchen, garage & large basement with ample storage, and meticulously manicured property wrapped in perennial gardens, stone walls, flowering bushes, perennials & trees. A rare and unique opportunity for those seeking craftsmanship, charm and an exceptional setting.

2 Beds ⋅ 1 Baths ⋅ 957742 MLS

Charming, warm and truly one of a kind, this very special storybook cottage is rich in character and classic, timeless details with a top, top location in North Saint James & nestled on the cusp of sought after Head Of The Harbor, close to the Saint James General Store, Route 25A Shopping, Schools, Stony Brook Village & just a short drive to Port Jefferson Village! Perfect as a year round home (with room for expansion) or a wonderful charming second home/summer getaway...The home offers two well sized bedrooms, immaculate full bathroom, a large great room (living room & dining room) with a striking stone fireplace taking center stage, beautifully framed by two stunning trapezoid shaped stained-glass windows that flood the space with warmth. Custom cabinetry & original details throughout including a hand carved front door, built in corner cabinet in the dining room (crafted by the homeowner), a cabinet lined kitchen, garage & large basement with ample storage, and meticulously manicured property wrapped in perennial gardens, stone walls, flowering bushes, perennials & trees. A rare and unique opportunity for those seeking craftsmanship, charm and an exceptional setting.

22 Hill Road, Saint James

$540,000

Rare opportunity in Fairfield at St. James

1 Beds ⋅ 2 Baths ⋅ 994244 MLS

Rare opportunity in Fairfield at St. James

607 Cabot Court, Saint James

$539,000

Discover the perfect opportunity to build your dream home in the prestigious and picturesque Village of Nissequogue. This 2-acre parcel is situated at the end of a serene cul-de-sac, offering privacy and tranquility in one of Long Island's most sought-after locations. Key Features: - Approved DEC and Health Department permits for a 5,000 square-foot custom home. - Elevated lot, providing stunning potential views and a commanding presence. - Located just minutes from the breathtaking Long Island Sound, where you can enjoy pristine beaches, scenic views, and all the natural beauty the area has to offer. - Proximity to renowned vineyards, stables, and golf courses, ensuring a lifestyle of leisure and sophistication. Don't miss this rare opportunity to own a piece of Nissequogue's serene and scenic beauty.

856145 MLS

Discover the perfect opportunity to build your dream home in the prestigious and picturesque Village of Nissequogue. This 2-acre parcel is situated at the end of a serene cul-de-sac, offering privacy and tranquility in one of Long Island's most sought-after locations. Key Features: - Approved DEC and Health Department permits for a 5,000 square-foot custom home. - Elevated lot, providing stunning potential views and a commanding presence. - Located just minutes from the breathtaking Long Island Sound, where you can enjoy pristine beaches, scenic views, and all the natural beauty the area has to offer. - Proximity to renowned vineyards, stables, and golf courses, ensuring a lifestyle of leisure and sophistication. Don't miss this rare opportunity to own a piece of Nissequogue's serene and scenic beauty.

8 Steep Bank Road, Saint James

$518,400

Lovingly maintained 2bd 1 1/2 bath unit located in the desirable Gotham section. Living room with 12ft ceilings and recessed lighting. Primary Bedroom suite, second bedroom with 1/2 bath. Completely updated , including new eat in kitchen with granite counter tops, stainless appliances ,updated baths with Primary bath walk in shower, new flooring, and custom closets. New Anderson windows and sliding glass door that leads to a beautiful patio area with new awning. Garage, which includes above attic storage with stair access. This unit is ready for you to move in settle down and enjoy. A few of the many amenities included in The Fairfield Community are a pool, tennis courts, and clubhouse just to to name a few.

2 Beds ⋅ 2 Baths ⋅ 1015354 MLS

Lovingly maintained 2bd 1 1/2 bath unit located in the desirable Gotham section. Living room with 12ft ceilings and recessed lighting. Primary Bedroom suite, second bedroom with 1/2 bath. Completely updated , including new eat in kitchen with granite counter tops, stainless appliances ,updated baths with Primary bath walk in shower, new flooring, and custom closets. New Anderson windows and sliding glass door that leads to a beautiful patio area with new awning. Garage, which includes above attic storage with stair access. This unit is ready for you to move in settle down and enjoy. A few of the many amenities included in The Fairfield Community are a pool, tennis courts, and clubhouse just to to name a few.

1305 Gotham Court W, Saint James

$515,000

Welcome to Fairfield at St. James, a desirable 55+ gated community! This spacious first-floor corner condo offers 2 bedrooms and 2 full baths with no one above. Enter into a foyer with large coat closet from your covered front porch. Enjoy an eat-in kitchen with stone countertops, dishwasher and electric oven with Microwave hood. A formal dining room comfortably fits a large table to seat 6+ and hutch. Spacious living room with sliders to a private patio. This unit has an in-unit washer and dryer, central air and electric heat. The patio features an awning and a charming garden area. Ideally located directly across from the clubhouse, pool and tennis courts!

2 Beds ⋅ 2 Baths ⋅ 1031076 MLS

Welcome to Fairfield at St. James, a desirable 55+ gated community! This spacious first-floor corner condo offers 2 bedrooms and 2 full baths with no one above. Enter into a foyer with large coat closet from your covered front porch. Enjoy an eat-in kitchen with stone countertops, dishwasher and electric oven with Microwave hood. A formal dining room comfortably fits a large table to seat 6+ and hutch. Spacious living room with sliders to a private patio. This unit has an in-unit washer and dryer, central air and electric heat. The patio features an awning and a charming garden area. Ideally located directly across from the clubhouse, pool and tennis courts!

302 Bentley Court W, Saint James

$509,000

Discover peaceful waterfront living in this well-maintained 2-bedroom, 2-full-bath condo situated directly on a serene pond. With only two buildings sharing the water view, the residence offers privacy and lasting vistas from every room. The spacious living/dining room combination creates an open, comfortable entertaining space, while the eat-in kitchen provides casual dining options. Recent updates include a newer roof, serviced central air conditioning, professionally cleaned carpeting and fresh paint in the main living area. Ideally located directly across from the clubhouse for easy access to community amenities. Low taxes and low common charges enhance the value. This active 55+ community rarely has waterfront units available—bring your finishing touches and make it your own.

2 Beds ⋅ 2 Baths ⋅ 982741 MLS

Discover peaceful waterfront living in this well-maintained 2-bedroom, 2-full-bath condo situated directly on a serene pond. With only two buildings sharing the water view, the residence offers privacy and lasting vistas from every room. The spacious living/dining room combination creates an open, comfortable entertaining space, while the eat-in kitchen provides casual dining options. Recent updates include a newer roof, serviced central air conditioning, professionally cleaned carpeting and fresh paint in the main living area. Ideally located directly across from the clubhouse for easy access to community amenities. Low taxes and low common charges enhance the value. This active 55+ community rarely has waterfront units available—bring your finishing touches and make it your own.

707 Bentley Court, Saint James

604 Cabot Court E Unit #604, Saint James

$499,999

Welcome to Fairfield at St James. This 55+ community features low taxes and green spaces with parkland, sidewalks, and pond, plus a Clubhouse with library, fitness center, billiards room, indoor pool, 2 outdoor pools, tennis and pickle ball courts. This 2 bedroom, 2 bath Condo is move-in ready. Enter the Condo and view a large front to back space with coat closet, Dining area and Living Room with sliding glass door to the patio that fill the room with natural light. Continue to the eat-in kitchen with light wood cabinetry, white appliances, a roomy space for table and chairs and a large window to enjoy the garden view. The hallway has fixed skylights that provide more natural light and acess to the pantry, the 2nd bedroom and the full bath with tub and shower. Next is the spacious primary bedroom with large windows, an adjoining dressing room with closets, a vanity with sink and door to a separate room for the shower and toilet.

2 Beds ⋅ 2 Baths ⋅ 993563 MLS

Welcome to Fairfield at St James. This 55+ community features low taxes and green spaces with parkland, sidewalks, and pond, plus a Clubhouse with library, fitness center, billiards room, indoor pool, 2 outdoor pools, tennis and pickle ball courts. This 2 bedroom, 2 bath Condo is move-in ready. Enter the Condo and view a large front to back space with coat closet, Dining area and Living Room with sliding glass door to the patio that fill the room with natural light. Continue to the eat-in kitchen with light wood cabinetry, white appliances, a roomy space for table and chairs and a large window to enjoy the garden view. The hallway has fixed skylights that provide more natural light and acess to the pantry, the 2nd bedroom and the full bath with tub and shower. Next is the spacious primary bedroom with large windows, an adjoining dressing room with closets, a vanity with sink and door to a separate room for the shower and toilet.

604 Cabot Court E Unit #604, Saint James

$499,000

Beautiful 2 bedroom, 2 bath lower-level 55+ condo located in the gated community of Fairfield at Saint James. This well-maintained one-floor unit offers an ideal blend of comfort and convenience. The spacious eat-in kitchen features ample cabinetry and plenty of natural light, flowing seamlessly into the formal dining and living room. Sliding doors lead to a private patio with peaceful greenery views, perfect for relaxing or entertaining. The primary bedroom includes a large en-suite bathroom and a generous walk-in closet, creating a comfortable retreat. A second bedroom, full bathroom, large hallway closet, and a laundry/utility room provide added functionality and convenience. Features 2 year old AC and hot water heater. Brand new roof. This highly desirable 55+ community offers an impressive array of amenities, including a clubhouse, tennis courts, two outdoor pools, an indoor pool, fitness center, library, and billiards room. Residents also enjoy access to convenient bus service for shopping. Ideally located near Smith Haven Mall, restaurants, a movie theater, and other everyday conveniences, this home is one you don’t want to miss.

2 Beds ⋅ 2 Baths ⋅ 951936 MLS

Beautiful 2 bedroom, 2 bath lower-level 55+ condo located in the gated community of Fairfield at Saint James. This well-maintained one-floor unit offers an ideal blend of comfort and convenience. The spacious eat-in kitchen features ample cabinetry and plenty of natural light, flowing seamlessly into the formal dining and living room. Sliding doors lead to a private patio with peaceful greenery views, perfect for relaxing or entertaining. The primary bedroom includes a large en-suite bathroom and a generous walk-in closet, creating a comfortable retreat. A second bedroom, full bathroom, large hallway closet, and a laundry/utility room provide added functionality and convenience. Features 2 year old AC and hot water heater. Brand new roof. This highly desirable 55+ community offers an impressive array of amenities, including a clubhouse, tennis courts, two outdoor pools, an indoor pool, fitness center, library, and billiards room. Residents also enjoy access to convenient bus service for shopping. Ideally located near Smith Haven Mall, restaurants, a movie theater, and other everyday conveniences, this home is one you don’t want to miss.

901 Fenway Road, Saint James

$499,000

Build Your Dream Home in Spectacular and Peaceful Nissequogue Village. Building permit was issued on 12/9/25. Located in the heart of the serene and prestigious Nissequogue Village, this exceptional property offers the rare opportunity to bring your vision to life. Key Features: • Approved blueprints for a luxurious 5-bedroom, 5.5-bathroom home designed with modern elegance and functionality. • All permits in place, ensuring a smooth and hassle-free building process. • Nestled in a tranquil setting, perfect for those seeking privacy and natural beauty. This is your chance to create a custom masterpiece in one of Long Island's most coveted communities. With its stunning surroundings and proximity to beaches, golf courses, and fine dining, Nissequogue Village offers an unparalleled lifestyle.

856152 MLS

Build Your Dream Home in Spectacular and Peaceful Nissequogue Village. Building permit was issued on 12/9/25. Located in the heart of the serene and prestigious Nissequogue Village, this exceptional property offers the rare opportunity to bring your vision to life. Key Features: • Approved blueprints for a luxurious 5-bedroom, 5.5-bathroom home designed with modern elegance and functionality. • All permits in place, ensuring a smooth and hassle-free building process. • Nestled in a tranquil setting, perfect for those seeking privacy and natural beauty. This is your chance to create a custom masterpiece in one of Long Island's most coveted communities. With its stunning surroundings and proximity to beaches, golf courses, and fine dining, Nissequogue Village offers an unparalleled lifestyle.

260 Old Mill Road, Saint James

$490,000

Stunning 2 Bedroom 2 Bath Renovated Upper Andover Model in the Highly Desired 55+ Fairfield @ St. James Gated Condominium Complex. This Andover Unit Renovation was Just Completed to Include a Remodeled Kitchen With New Stainless Steel Appliances, Recessed Lighting, Waterproof Laminate Flooring. All Doors, Hardware, Moldings, Electrical Outlets & Switches, Lighting Fixtures are New and Unit is Freshly Painted. Unit has Super Spacious Sized Rooms with Loads of Natural Light Coming in Through Updated Windows. Sliding Doors Lead to Private Covered Deck Area with Nice Wooded Views. There is a Separate Utility Room W/ Washer & Dryer, HVAC System, Hot Water Heater. HVAC System Serviced in December. Amenities Include Trips, Fitness Center, Indoor & Outdoor Swimming Pools, Billiards, Library, Tennis, Bocce, Pickleball, & Clubhouse Activities. LOW TAXES AND HOA!! COME SEE THIS GORGEOUS UNIT AND MAKE IT YOUR HOME!

2 Beds ⋅ 2 Baths ⋅ 966450 MLS

Stunning 2 Bedroom 2 Bath Renovated Upper Andover Model in the Highly Desired 55+ Fairfield @ St. James Gated Condominium Complex. This Andover Unit Renovation was Just Completed to Include a Remodeled Kitchen With New Stainless Steel Appliances, Recessed Lighting, Waterproof Laminate Flooring. All Doors, Hardware, Moldings, Electrical Outlets & Switches, Lighting Fixtures are New and Unit is Freshly Painted. Unit has Super Spacious Sized Rooms with Loads of Natural Light Coming in Through Updated Windows. Sliding Doors Lead to Private Covered Deck Area with Nice Wooded Views. There is a Separate Utility Room W/ Washer & Dryer, HVAC System, Hot Water Heater. HVAC System Serviced in December. Amenities Include Trips, Fitness Center, Indoor & Outdoor Swimming Pools, Billiards, Library, Tennis, Bocce, Pickleball, & Clubhouse Activities. LOW TAXES AND HOA!! COME SEE THIS GORGEOUS UNIT AND MAKE IT YOUR HOME!

909 Fenway Road, Saint James

$477,500

Welcome to Fairfield at St. James, a desirable 55+ gated community. This completely remodeled 2-bedroom (1 Bedroom was the dining room closed currently)., 1.5-bath ranch-style condo offers an open and spacious layout with gleaming hardwood floors throughout. The formal living room flows seamlessly into a modern kitchen featuring stainless steel appliances, stone countertops, and a detailed backsplash. The home includes a beautifully updated full bath and half bath, plus the convenience of an in-unit washer and dryer. Enjoy your own private, secluded patio—perfect for relaxing outdoors on warm summer days. Community amenities and low-maintenance living make this home a wonderful opportunity. Fairfield Community Amenities include a Clubhouse, 1 indoor pool and 2 outdoor pools, tennis court, billiards, pickleball, bocce and fitness center. Located close to shopping and restaurants, including the Smith Haven Mall.

2 Beds ⋅ 2 Baths ⋅ 963252 MLS

Welcome to Fairfield at St. James, a desirable 55+ gated community. This completely remodeled 2-bedroom (1 Bedroom was the dining room closed currently)., 1.5-bath ranch-style condo offers an open and spacious layout with gleaming hardwood floors throughout. The formal living room flows seamlessly into a modern kitchen featuring stainless steel appliances, stone countertops, and a detailed backsplash. The home includes a beautifully updated full bath and half bath, plus the convenience of an in-unit washer and dryer. Enjoy your own private, secluded patio—perfect for relaxing outdoors on warm summer days. Community amenities and low-maintenance living make this home a wonderful opportunity. Fairfield Community Amenities include a Clubhouse, 1 indoor pool and 2 outdoor pools, tennis court, billiards, pickleball, bocce and fitness center. Located close to shopping and restaurants, including the Smith Haven Mall.

201 Bentley Court E, Saint James

$475,000

Enjoy the condo lifestyle in this stunning, fully renovated, one-level condo in the Fairfield at St. James 55+ gated community featuring an open and beautifully updated kitchen with quartz countertops, oversized island, custom backsplash, abundant cabinetry, stainless steel appliances and a pantry closet, central air conditioning, hardwood floors, crown molding, recessed lighting, solar tubes, new luxury bathroom, new doors, fresh paint, two walk in closets, young washer and dryer, new extended paver patio with electric awning, taxes of only $2,198.10 after basic star and common charges of $302/month (including cable). Community amenities include clubhouse, an indoor pool, two outdoor pools, fitness center, library, billiards, tennis, bocce, pickleball and a scenic walking trail all in an unbeatable location near the Smith Haven Mall, with easy access to restaurants, shopping, and virtually every retailer and convenience imaginable. With everything updated and low taxes, low utilities, and low maintenance—low bills—this is easy living at its best. Come see for yourself.

1 Beds ⋅ 1 Baths ⋅ 955663 MLS

Enjoy the condo lifestyle in this stunning, fully renovated, one-level condo in the Fairfield at St. James 55+ gated community featuring an open and beautifully updated kitchen with quartz countertops, oversized island, custom backsplash, abundant cabinetry, stainless steel appliances and a pantry closet, central air conditioning, hardwood floors, crown molding, recessed lighting, solar tubes, new luxury bathroom, new doors, fresh paint, two walk in closets, young washer and dryer, new extended paver patio with electric awning, taxes of only $2,198.10 after basic star and common charges of $302/month (including cable). Community amenities include clubhouse, an indoor pool, two outdoor pools, fitness center, library, billiards, tennis, bocce, pickleball and a scenic walking trail all in an unbeatable location near the Smith Haven Mall, with easy access to restaurants, shopping, and virtually every retailer and convenience imaginable. With everything updated and low taxes, low utilities, and low maintenance—low bills—this is easy living at its best. Come see for yourself.

203 Cabot Court S, Saint James

$475,000

Fairfield at St. James - 55+ Community. Diamond Condition 1 Bedroom, l.5 Bath. Completely redone unit featuring a beautifully updated kitchen, new bathrooms, Lifeproof Vinyl Flooring throughout. Energy efficient upgrades to include new baseboards, thermostats, lighting, electrical panel, outlets, bathroom heaters/fans and hot water heater. New appliances (dishwasher never used). Ample closets and storage. Move-in ready. Community amenities include inground pool, tennis, pickleball, bocce, billiards, clubhouse, gym, library, organized trips and transportation to Smithtown Senior Center and Smithhaven Mall. This is an active senior community. Basic Cable included in HOA. Private location! Low taxes $3,200 and HOA $313. This unit will not last!

1 Beds ⋅ 2 Baths ⋅ 935978 MLS

Fairfield at St. James - 55+ Community. Diamond Condition 1 Bedroom, l.5 Bath. Completely redone unit featuring a beautifully updated kitchen, new bathrooms, Lifeproof Vinyl Flooring throughout. Energy efficient upgrades to include new baseboards, thermostats, lighting, electrical panel, outlets, bathroom heaters/fans and hot water heater. New appliances (dishwasher never used). Ample closets and storage. Move-in ready. Community amenities include inground pool, tennis, pickleball, bocce, billiards, clubhouse, gym, library, organized trips and transportation to Smithtown Senior Center and Smithhaven Mall. This is an active senior community. Basic Cable included in HOA. Private location! Low taxes $3,200 and HOA $313. This unit will not last!

401 Cabot Court E, Saint James

$470,000

First floor/ground floor unit in the charming 55+ Fairfield at St. James Community. This lovely move-in ready unit situated on a cul-de-sac for added privacy offers high ceilings with natural light and stunning views of the sunset with patio exposure facing west. One car attached garage, Hard wood floors throughout, In-unit washer and dryer for added convenience, Private patio with sliding doors, beautiful primary suite with two double door closets. Fairfield Community Amenities include a Clubhouse, pool, tennis court and fitness center. There is a No pets allowed policy. Make this beautiful unit your own!

1 Beds ⋅ 2 Baths ⋅ 967542 MLS

First floor/ground floor unit in the charming 55+ Fairfield at St. James Community. This lovely move-in ready unit situated on a cul-de-sac for added privacy offers high ceilings with natural light and stunning views of the sunset with patio exposure facing west. One car attached garage, Hard wood floors throughout, In-unit washer and dryer for added convenience, Private patio with sliding doors, beautiful primary suite with two double door closets. Fairfield Community Amenities include a Clubhouse, pool, tennis court and fitness center. There is a No pets allowed policy. Make this beautiful unit your own!

1205 Gotham Drive, Saint James