Refine Search
Sort by
$665,000
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

$655,000
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
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
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
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
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

$550,000
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
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

$539,000
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

$509,000
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

$499,999
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
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
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
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
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
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
1 Beds 2 Baths 954627 MLS
Beautifully Updated 1 Bedroom, 1.5 Bath Ranch Located In The Highly Sought-After 55+ Active Community at Fairfield Saint James. This Move In Ready Home Features A New White Kitchen W/Quartz Countertops, New Appliances, Full Size Washer Dryer, Modern Baths, Central Air Conditioning And New Vinyl Flooring Throughout. Additional Features Include Oversized Closets, Recessed Lighting, Generous Sized Rooms, Formal Dining Area & Den With Glass Sliders To Private Patio. Fairfield Saint James Is A Gated Community Offering A Vibrant Lifestyle With Numerous Activities: Clubhouse, Pool(s), Tennis/Pickleball, Gym, Sauna & Walking Trails Throughout. Conveniently Located Close To Restaurants, Parks & Shops. Offering A Shuttle Service To All. *Taxes $3,453

101 Flair Court E, Saint James

$475,000
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

$445,000
1 Beds 2 Baths 993174 MLS
Don’t miss this bright and spacious 1-bedroom, 1.5-bath condo located in the 55+ Fairfield community in St. James. Thoughtfully maintained, this home features a well-designed layout with a large living and dining area, a light-filled eat-in kitchen, and a generously sized primary suite complete with its own private bath. The bright, open layout creates a warm and welcoming atmosphere, making everyday living feel effortless and enjoyable. Enjoy added conveniences such as in-unit laundry, generous storage, drive-way parking and easy low-maintenance living. The community is peaceful and beautifully maintained, offering outstanding value with low taxes and affordable HOA dues. Community amenities include in-ground pool, tennis, pickleball, bocce, billiards, clubhouse, gym

604 Gotham Drive, Saint James

$430,000
1 Beds 1 Baths 1012236 MLS
Incredible Opportunity to Enjoy the Lifestyle You’ve Been Waiting For in the Highly Desirable Fairfield 55+ Community in St. James! This exceptional first-floor condominium offers true no-step living, making everyday life effortless and convenient. Ideally located just steps from your assigned parking space, this light-filled home features an open and inviting floor plan designed for comfortable living and entertaining. The spacious living room showcases recessed lighting and a large sliding glass door that fills the space with natural light while providing access to your private patio. The eat-in kitchen offers white cabinetry, white appliances, a stackable washer and dryer, recessed lighting, a ceiling fan, and abundant cabinet and counter space. Custom plantation shutters throughout allow you to enjoy natural sunlight or complete privacy at any time. The oversized primary bedroom features a large walk-in closet, while the updated full bathroom includes a white vanity, black-framed mirror, and spacious walk-in shower. Additional highlights include central air conditioning, an exterior storage closet, assigned parking, and ample guest parking. Enjoy a carefree, resort-style lifestyle with low taxes and access to outstanding community amenities, including indoor and outdoor saltwater pools, a fitness center, clubhouse, library, billiards room, card room, tennis courts, pickleball courts, walking trails, a gazebo, picturesque pond, and a full calendar of social activities. Conveniently located near shopping, dining, and transportation, this is an exceptional opportunity to enjoy active adult living at its finest. HOA approval required. Low taxes.

703 Drew Drive Unit #D7, Saint James

$419,000
1 Beds 2 Baths 983224 MLS
Welcome to 209 Cabot Ct, located in the highly sought-after 55+ adult community of Fairfield in St. James. This desirable ground-level end unit is situated near a peaceful pond and offers convenient access to nearby shopping and restaurants. The home is well maintained and provides a great opportunity for updates to make it your own. The spacious, light-filled living room flows into the dining area, featuring sliding doors that open to a private patio with a storage shed. While this unit does not include a garage, it offers a private driveway along with ample additional parking directly in front of the condo. Residents enjoy a wide range of amenities, including a clubhouse, pool, tennis courts, pickleball courts, and a fitness center. The HOA covers exterior and common area maintenance, snow removal, and trash service. Low taxes add to the overall appeal of this wonderful community.

209 Cabot Court S, Saint James

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.