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$1,150,000
3 Beds ⋅ 2 Baths ⋅ 1048523 MLS
Celebrating the 100th birthday of this timeless Oyster Bay classic, this cherished home is ready for its next owner to love and enjoy, just as it has been for more than 40 years. by current owners, Historic charm blends seamlessly with exceptional modern updates throughout. A welcoming four-season front porch leads to elegant living and dining rooms, original beautiful wood floors, crown molding accents, highlighted by a stunning new staircase. to second floor, The Elegant showstopping 2025 custom kitchen features natural marble countertops, custom cabinetry, a designer backsplash, a coffee-wine bar, and a large center island, opening seamlessly to a sun-drenched family room with soaring ceilings, skylights, and a custom gas fireplace accented with stone facade. Sliding glass doors lead to a private, oversized PVC-fenced backyard 50x150 depth, with a spacious custom deck, creating the perfect setting for indoor-outdoor entertaining living. a custom play ground swing set is included with sale . From the custom elegant new staircase, to second floor , you'll find a spacious primary bedroom, two additional bedrooms, all with wood floors and brand new ductless air conditioning , a beautifully updated full bath, and a third-floor bonus loft with breathtaking winter water views via 2 custom oversized windows of Oyster Bay Harbor. The Full walkout basement includes a workshop, ideal for hobbies, projects, and unlimited additional storage. Completely renovated within the past three years, this home offers extensive improvements, including a beautifully renovated front porch, new windows, a custom kitchen and baths, new flooring, a new staircase, ductless split air conditioning, a custom gas fireplace, recessed lighting, a custom paver driveway, an oversized deck, and a private PVC-fenced backyard. Ideally located in the heart of historic Oyster Bay, this exceptional home is just a short stroll to Quaint shops, Fabulous restaurants, Theodore Memorial park, Sandy beaches, Fishing pier, playgrounds, Sagamore Hill National Park, Famed Oyster Bay Waterfront Center, Tennis-Pickle ball Courts, Marina, public transportation, and everything this beloved historic waterfront community has to offer. Located within the highly regarded Oyster Bay School District.

182 School Street, Oyster Bay
$979,000
3 Beds ⋅ 2 Baths ⋅ 1045148 MLS
Welcome to 64 Tooker Avenue, a beautifully restored 1893 colonial offering approximately 2000 ft.; of character filled living space in the heart of Oyster Bay. Thoughtfully improved and meticulously maintained, this 3 bedroom, 2 bathroom home blends original craftsmanship with comfortable modern living. Inside, refinished hardwood floors, painstakingly restored original millwork, period details and custom built-ins reflect the home’s history, while a sun filled southern exposure creates bright, inviting spaces throughout. The first floor offers a formal dining room, living room, renovated kitchen, sunroom, mud/laundry room and a handsome home office with custom doors, cabinetry and bookshelves. Upstairs 3 bedrooms and a finished attic provide flexible space for work, play, guests, or additional storage. An exceptionally clean and bright, lower level provides abundant storage, pantry space, and a dedicated room for a workshop or hobbies. The home’s outdoor spaces have been transformed into a private retreat. Thoughtfully designed landscaping surrounds a fenced yard with a Trex deck, Cambridge paver patio, bluestone walkways, perennial gardens and raised vegetable beds, all supported by a 10 zone irrigation system. A detached garage and freshly painted exterior complete the property. Set on approximately 0.186 acres in Oyster Bay-East Norwich School District, 64 Tooker Avenue offers the rare combination of historic character, thoughtfully updated living spaces and beautifully designed outdoor areas all meticulously cared for and ready for its next chapter. Ideally located just blocks from Oyster Bay Hamlet’s restaurants, shops, and museums, with the LIRR, local beaches and waterfront parks all nearby.

64 Tooker Avenue, Oyster Bay
$1,284,999
4 Beds ⋅ 3 Baths ⋅ 1045875 MLS
Welcome to 10 Highwood Road. This home offers a perfect combination of modern upgrades while retaining the homes natural charm. An extensively updated 4-bedroom, 3-bath California split on a quiet tree lined block. Open Floor concept with cathedral ceilings accented by wood beams and paneling. Short runs of stairs separate living, sleeping, and lower-level space so the house feels open without feeling oversized. The updated kitchen is the showpiece. Custom KraftMaid maple cabinetry, quartz counters, a marble backsplash, stainless workstation sink, Zephyr ducted range hood, and LG French-door refrigerator give you a room that actually works for entertaining. A new Andersen patio door ties the main living area to the backyard. Comfort is handled by 5-zone Mitsubishi heating and cooling. The lower level is finished with porcelain flooring and a standing shower, so it functions as real living space — family room, guest suite, or office — not leftover basement. A custom staircase railing ties the levels together. Outside, the work is recent and usable: new backyard concrete and paver hardscaping, new partial fence and lighter stone retaining walls, smart multi-zone irrigation, landscape lighting, and motion-sensing garage lights. A new driveway with paver accents is coming soon. Systems were just reset in 2026: Peerless oil-fired boiler with Riello F5 burner, 40-gallon indirect water heater, new copper water piping, and new heating/hot-water zone valves with Honeywell thermostat. Limited-lifetime warranties on the boiler and water heater and a 3-year qualifying labor warranty come with the house. Partial roof and chimney work date to 2018. Improvement documentation and select protection plans are available. Located in a small, wooded hamlet with Oyster Bay village, beaches, and marinas a few minutes north, Rothmann’s and Pine Hollow nearby, and two miles from the LIRR options. Close to shops, restaurants, parks and schools.

10 Highwood Road, East Norwich
$4,995,000
3 Beds ⋅ 3 Baths ⋅ 1008706 MLS
Spectacular Waterfront Retreat on 2 Verdant Acres This extraordinary 2-acre waterfront retreat is where privacy, elegance, and natural beauty come together in perfect harmony. Designed by Brian Shore, it extends over 360 feet of waterfront and was built to take advantage of the panoramic views of Cold Spring Harbor and the Long Island Sound. This magnificent Post Modern boasts seamless indoor-outdoor living with high ceilings and a spacious open floor plan filled with abundant natural light that streams through expansive windows. The great room has a vaulted ceiling with beams, a fireplace, and wall-to-wall windows framing incredible water views. Adjacent is the dining room and an open kitchen with professional-grade Wolf and Sub-Zero appliances, an ocean-hued backsplash, and nautical-inspired fixtures, forming the perfect coastal backdrop for the stunning vistas. Off the great room, there is a generous composite deck that spans the entire length of the house. The tranquil master suite has equally exquisite views and features 3 walk-in closets and an expansive master bath. On the walk-out lower level, a water-view family room is complemented by a study, two bedrooms, a full bath, a laundry room, and a beach shower. Property highlights include hardwood floors throughout the main floor, central vacuum, sprinklers, 4-Zone air-conditioning, a 3-car garage, and park-like property. Close to dining, shopping, beaches, parks, and LIRR. Whether enjoying sunrise views over the water, relaxing on the beach, or entertaining against a backdrop of spectacular scenery, this remarkable estate presents a rare opportunity to own a truly special waterfront property.

47 Laurel Cove Road, Laurel Hollow
$1,150,000
4 Beds ⋅ 4 Baths ⋅ 907283 MLS
Great Investment Opportunity! Currently being used as a Medical Practice, but it can be converted to Family Residence. The property sits on a 12,001 SF Corner Lot with a beautiful curb appeal. The building consists of 4524 SF. Total of 13 rooms. The 1st Floor features 3 Exam Rooms, 2 Doctor's Offices, Reception Area, Waiting Room, 2 Half Baths, Additional Lounge Room for Staff w/ Kitchen, Dining Area, and Full Bath. Basement is partially finished and has lots of Extra Storage Space. Walk-Out-Basement. New Roof. The building has an accessory 1-Bedroom apartment on the 2nd Floor. Large Driveway newly paved, parking space available for 11 cars. Zoning is permitted for Medical Practices Related. Zoning can be changed though a Special Use Permit application with the Oyster Bay Zoning Board of Appeals office, but only for professional services. Prime Location with high visibility and easy access to parkways. Near the LIRR, shops, schools, parks, beaches, restaurant and entertainment.

188 W Main Street, Oyster Bay

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.