Saint James Real Estate

Welcome to Saint James, a charming hamlet nestled in the heart of Suffolk County, New York. This picturesque community is part of the Town of Smithtown and offers a delightful blend of suburban tranquility and vibrant local culture. With its tree-lined streets, historic homes, and a welcoming atmosphere, Saint James is an ideal place for families, retirees, and anyone looking to enjoy the beauty of Long Island living.

Saint James boasts an array of amenities that cater to all lifestyles. Residents enjoy easy access to pristine parks, including the scenic Caleb Smith State Park Preserve, which offers opportunities for hiking, fishing, and picnicking amidst nature’s splendor. The local shopping scene is equally appealing, featuring charming boutiques, cozy cafes, and popular restaurants that serve everything from gourmet fare to casual bites.

Education is a cornerstone of the community, with highly-rated schools that provide exceptional learning environments for children. Saint James is served by the Smithtown Central School District, known for its commitment to academic excellence and student development.

For those who appreciate the arts, the nearby Smithtown Performing Arts Center hosts a variety of theatrical productions and events throughout the year, fostering a rich cultural experience. Plus, with its convenient location, residents can easily access the vibrant attractions of New York City, making it the perfect balance of small-town charm and metropolitan convenience.

Whether you're looking to buy your first home, retire in peace, or simply explore a new neighborhood, Saint James offers a welcoming community with something for everyone. Come and discover the beauty and charm of Saint James, where your dream home awaits!

Newest Listings in Saint James

$399,000

1 Beds ⋅ 2 Baths ⋅ 1033101 MLS

Well Maintained And Spacious Condo Unit At Desirable Fairfield 55+ Community. Features Include Eat-In-Kitchen With Washer/Dryer And Dishwasher, Dining Room, Living Room With Sliders Leading To Patio, Primary Bedroom, Full Bathroom, Half Bathroom, Garage, Freshly Painted, Brand New Laminate Flooring, Lots Of Organized Closet Space. Great Amenities Include Basketball Courts, Indoor/Outdoor Pool, Clubhouse, Tennis, Recreational Facilities, Snow Removal, Security, Gated. All Info Must Be Verified by Buyers & Buyers Agents

1006 Cabot Path, Saint James

$1,190,000

5 Beds ⋅ 3 Baths ⋅ 1032455 MLS

Located on a picturesque, tree-lined street in the heart of St. James, this stunner checks every box! Flooded with sunlight, the spacious kitchen features custom white cabinetry, a large center island and stainless steel appliances and opens seamlessly into a large den with fireplace. The expansive living space overlooks the private, resort-like yard. The two-story entry foyer, coupled with the 9 foot ceilings on the entire first floor and the tray ceiling in dining room enhance the bright and airy feel of this entertainers dream. All of the principle rooms are large and there are hardwood floors throughout. The oversized primary suite has a tray ceiling, walk-in closet and a double vanity spa-like en-suite bath with soaking tub. Additional bedrooms are all well-sized with excellent closet space, and a fifth bedroom with full bath on main level is ideal for home office or guest suite. Outside, an in-ground heated, saltwater pool is complimented by a serene waterfall feature and has a large paver patio perfect for abundant seating, lounging and entertaining. The full basement offers high ceilings. Generator panel in garage and portable generator that stays with the home. Plus, 200 amp service provides added peace of mind. Updated CAC, Andersen windows. In-ground sprinklers. This home will not last!

61 Hillside Avenue, Saint James

$649,990

3 Beds ⋅ 2 Baths ⋅ 1029446 MLS

Charming Ranch on Oversized Lot in Desirable St. James! Welcome home to this warm and inviting 3-bedroom, 2-bathroom Ranch nestled on an oversized property in the heart of St. James. Offering the ease of single-level living paired with incredible expansive outdoor space, this home is perfect for both relaxed daily living and effortless entertaining. Features Main Level with Bright, fluid layout featuring three comfortable bedrooms and one full bathroom. Finished Basement: with Additional finished space and 2nd Full Bathroom. Outdoor Oasis is Set on an unusually deep/large lot. Limitless potential for a pool, outdoor kitchen, or garden expansion. Prime St. James Location: Enjoy proximity to local shops, dining, top-rated schools, and convenient LIRR access. Don’t miss this rare combination of prime St. James property.

101 Lake Avenue, Saint James

$678,000

4 Beds ⋅ 3 Baths ⋅ 1031653 MLS

Classic Colonial home offering spacious, and comfortable living . The expansive living room and beautiful wood floors throughout the home create a warm and inviting atmosphere. The eat-in kitchen flows seamlessly into the den, featuring a cozy wood-burning fireplace—perfect for everyday living and entertaining. The primary bedroom boasts an updated marble en-suite bath, while the additional bathrooms have also been tastefully renovated with quality finishes. In addition there are 3 nicely sized bedrooms on the second floor. The recently remodeled basement features durable luxury vinyl plank flooring and an outside entrance, providing versatile space for recreation, or a home office.. Step outside to enjoy the backyard deck with retractable awning, ideal for relaxing or hosting gatherings. Conveniently located near local shopping, the Long Island Rail Road, area beaches, fine dining, and Stony Brook University, and Stony Brook University Medical Center, this home offers the perfect combination of comfort, and accessibility. Smithtown Schools

322 2nd Avenue, Saint James

$399,000

1 Beds ⋅ 1 Baths ⋅ 1030363 MLS

Welcome to 1203 Cabot Court, the greatest opportunity in one of Long Island’s most sought-after 55+ developments located in the heart in historic Saint James on 50 acres. This condo features 1 bedroom and 1 full bath. Design your own open layout to your personal taste. Plan where to locate your in-unit laundry & central air vents! Sliding glass doors lead to a private patio plus attached garage with storage & shared driveway with one space. The Fairfield at Saint James community provides resort-style amenities including a clubhouse, fitness center, basketball, tennis & new pickleball courts. Enjoy swimming no matter the season! The indoor pool is open during the winter season & two outdoor in-ground pools are open during the summer season. Residents enjoy a vibrant social calendar, there are beautifully manicured grounds, well maintained blacktop trails and benches run throughout this lush community affording residents ability to take in the lake views and water features throughout this secure gated community. The Fairfield which has 675 units built from the early 1970's throughout the 1990's offers low common charges, low taxes and is close proximity to Smith Haven Mall shopping, top dining, golf, Award Winning Stonybrook Hospital 4.7 miles away, beautiful North Shore beaches & major highways. Only 2.1 miles to Saint James LIRR Station for an easy commute to Manhattan. One can experience a comfortable lifestyle within a 30 minute plus drive to vineyards, farmstands & seasonal resorts throughout the coveted North Fork of Long Island. This opportunity of a lifetime will not last long!

1203 Cabot Court, Saint James

$499,000

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

$990,000

4 Beds ⋅ 3 Baths ⋅ 1028829 MLS

Welcome home to this Post Modern Colonial, where an impressive two-story entry foyer creates a grand first impression. Beautiful hardwood floors, finished in a modern gray tone, extend throughout the entry foyer, staircase, formal living room, and formal dining room, creating a warm and cohesive flow. Designed for today's lifestyle, the home features a desirable open-concept kitchen and family room with a wood-burning fireplace flanked by custom built-ins, making it the perfect gathering space. The spacious primary suite offers a walk-in closet and a private ensuite bath, while a conveniently located first-floor laundry/mudroom with a new front-load washer and dryer adds everyday functionality. Set on a landscaped .43-acre property in the heart of St. James, the private, fenced backyard is an entertainer's dream, featuring an expansive paver patio with a built-in firepit plus a separately fenced saltwater inground pool with waterfall. Pool updates include new filter, heat pump, and Loop-Loc cover, as well as new pavers surround the pool area, while the gazebo provides the perfect place to relax. Thoughtfully updated for today's modern lifestyle, the home features a Smart Home system allowing you to control lights, doors, and central air from your smartphone, along with a security system with cameras for added peace of mind. Additional improvements include a 2020 roof, a 2024 natural gas heating system, CAC with the second-floor compressor replaced in 2023, a separate gas hot water heater, 200-amp electric service with a dedicated panel for an EV charger, and owned solar panels installed in 2020, providing lower electric costs and valuable property tax exemptions. (Note: Taxes being professionally grieved with an estimated $3,300 reduction; grievance is transferable to the Buyer.) Ideally located on a cul-de-sac and just a short walk to Lake Avenue's shops and restaurants, including the new Galiano Wine Bar. This home also offers beach rights to multiple Town of Smithtown beaches, proximity to parks, hiking trails, and nature preserves, and is situated within the highly regarded Smithtown Central School District.

4 Patricks Way, Saint James

$739,000

3 Beds ⋅ 2 Baths ⋅ 1028816 MLS

Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of St. James! Convenient distance to shops, restaurants and transportation with taxes under 9k! The stunning 2025 kitchen renovation is the centerpiece of the home. Showcasing natural quartzite countertops, full height backsplash, a 9 ft island with waterfall, professional grade appliances featuring a 6 burner gas range with vented hood. A bar area with beverage center and secondary workstation sink. Original hardwood floors run throughout the home. The fully enclosed, heated and air-conditioned front porch offers year-round enjoyment. The main level also features a formal living room, a full bathroom, recessed lighting, and efficient 4-zone heating and 3-zone cooling for personalized comfort. Upstairs, you'll find the three bedrooms, and another full bathroom, served by 3-zone heating and 2-zone cooling. The partially finished basement was completed in 2024 and provides additional living space. It has its own dedicated heating and cooling zone, along with a front-loading washer and gas dryer. A new high-efficiency Laars wall-mounted gas boiler was installed in 2025. In 2026, the home was fully insulated and finished with maintenance-free Cedar Impressions vinyl siding. The oversized detached two-car garage is equipped with a 60-amp subpanel, multiple 20-amp outlets, and hot and cold water with waste plumbing—ideal for a workshop or hobby space. The property also features a beautifully designed paver patio complete with a wet bar (2024)—perfect for entertaining, ample driveway parking, RV parking, hot and cold exterior water spigots. Additional highlights include Andersen® Thermopane windows, newer architectural roof, new exterior doors, 200-amp electrical service with generator hookup, wifi smart thermostats & porch lights, and eight surveillance cameras. Ideally located a short walk to Lake Avenues shop and restaurants. This home also offers beach rights to multiple Smithtown beaches, close proximity to parks, hiking trails and nature preserves. Situated in the highly regarded Smithtown Central School District.

116 Railroad Avenue, Saint James

$2,375,000

5 Beds ⋅ 4 Baths ⋅ 1027926 MLS

Tucked away on two acres at the end of a quiet cul-de-sac, in the prestigious enclave of Head of the Harbor, this magnificent five-bedroom, four-bath estate offers an unparalleled blend of modern luxury and serene privacy. The entire residence has undergone a comprehensive transformation over the past six years, resulting in a home that feels brand new while retaining its sophisticated, timeless character. The heart of the home is the stunning new kitchen, designed with a modern aesthetic that features sleek finishes, built-in Sub-zero refrigerator, Wolf oven, Jenn Air cooktop- with an intuitive layout perfect for both daily living and large-scale hosting. The large center island with seating, waterfall-edge quartz countertop and second sink invites entertaining on a grand scale, or just a perfect intimate gathering. The new picture window provides a panoramic view of the pristine outdoor, resort-like grounds. Off the kitchen, enjoy casual meals in the glass-enclosed dining area. The main floor also features a formal dining room, a bedroom and full bathroom, in addition to the entertaining spaces, which include an expansive family room with fireplace and access to the patio, an adjacent living room, and a bright, open sitting room off the kitchen with floor-to-ceiling windows looking out to the parklike property. Each of the four full bathrooms has been exquisitely renovated with designer fixtures, heater floor in the primary suite, and contemporary tiling, providing a spa-like experience in every corner of the house. The home's electric service has been upgraded to 450 amp in 2022, and also has a whole house natural gas generator, providing comfort along with style across the entire living space! Beyond the interior, the property serves as a private sanctuary. A brand-new patio leads to a sparkling pool with all new equipment installed in 2022, creating an outdoor oasis framed by mature trees and fenced-in expansive greenery across the 2 acre property. You will also find a dining pavilion offering shade and comfort, a bar, and a cabana with a changing area, bath and outdoor shower for added convenience. The commitment to quality is evident in the structural upgrades as well, including a new balcony off of the primary suite, new roof and the addition of owned solar panels for exceptional energy efficiency. The lower level reveals a fully finished basement, offering versatile space including a summer kitchen, new full bathroom, home gym, media room and recreation area. With every detail meticulously addressed—from the expansive living spaces to the secluded acreage—this estate represents a rare opportunity to enjoy a turnkey lifestyle in one of the most sought-after locations on the North Shore. Note: please see the attached document for a full list of upgrades to this home!

5 Meadow Gate W, Saint James

$700,000

4 Beds ⋅ 2 Baths ⋅ 1027335 MLS

This Hi-Ranch Style Home Features 4 Bedrooms, 2 Full Baths, Formal Dining Room, Kitchen & 1 Car Garage. The information provided is estimated to the best of our abilities at this time.

47 Cleremont Avenue, Saint James

$749,999

3 Beds ⋅ 2 Baths ⋅ 1026215 MLS

Nestled on an expansive 12,195 sq. ft. fully fenced property in the heart of St. James and located within the highly acclaimed Smithtown School District, this beautifully maintained farmhouse style Cape Cod is the perfect place to call home. Offering 3 spacious bedrooms and 2 full bathrooms, this inviting residence blends timeless charm with thoughtful updates throughout. Beautifully refinished hardwood floors, a sun filled living room with recessed lighting, a formal dining room, and an updated kitchen create a warm and welcoming atmosphere that's ideal for both everyday living and entertaining. Main-floor laundry adds everyday convenience. The second-floor features three generously sized bedrooms, a full bathroom, a huge walk-in closet, and a large walk-up attic, providing exceptional storage and flexibility. A full basement offers even more storage space and endless possibilities. Step outside to enjoy your private fully fenced front and backyard, complete with a newly updated patio perfect for summer barbecues, outdoor gatherings, gardening, or simply relaxing while enjoying the oversized yard. Ideally located just minutes from the St. James LIRR station, shopping, restaurants, parks, and major roadways, this exceptional home offers the perfect combination of charm, space, convenience, and location. Don't miss the opportunity to own this move-in-ready gem in one of Long Island's most sought-after communities.

214 1st Street, Saint James

$1,589,000

5 Beds ⋅ 4 Baths ⋅ 1024519 MLS

Spectacular 5 BR, 3.5 Bath Post-Modern Colonial in a premier 24hr gated community. This home has been extensively updated with incredible attention to detail. Features include brand-new solid oak hardwood floors throughout the entire house. The spacious kitchen is beautifully updated with a brand-new dishwasher, a high-efficiency exhaust fan, and sleek new countertops with a deep-basin sink. Enjoy a grand open layout, sun-drenched principal rooms, a family room with a fireplace, and a massive primary suite. Pristine 0.41-acre property with a 3-car garage and full basement. Resort-style community amenities include a private clubhouse, sparkling pool, fitness center, and Playground. Smithtown School District. Impeccably maintained with too many updates to list—this turn-key gem feels brand new!

35 Monterrey Drive, Saint James

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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.