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$1,250,000
3 Beds ⋅ 2 Baths ⋅ 1026168 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. Historic charm blends seamlessly with exceptional modern updates throughout. A welcoming four-season front porch leads to elegant living and dining rooms, highlighted by a stunning new staircase. The showstopping 2025 custom kitchen features marble countertops, custom cabinetry, a designer backsplash, a coffee bar, and a large center island, opening seamlessly to a sun-filled family room with soaring ceilings, skylights, and a custom gas fireplace. Sliding glass doors lead to a private, PVC-fenced backyard with a spacious custom deck, creating the perfect setting for indoor-outdoor living. Upstairs, you'll find a spacious primary bedroom, two additional bedrooms, a beautifully updated full bath, and a third-floor bonus loft with breathtaking views of Oyster Bay Harbor. The finished walkout basement includes a workshop, ideal for hobbies, projects, or 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 shops, restaurants, parks, beaches, public transportation, and everything this beloved waterfront community has to offer. Located within the highly regarded Oyster Bay School District.

182 School Street, Oyster Bay
$4,998,000
3 Beds ⋅ 3 Baths ⋅ 1026267 MLS
Immerse yourself in this stunning waterfront villa on Centre Island. Although newly rebuilt inside and out, the original character of this 1929 colonial creates an amazing synergy between modernity and history. Perched comfortably above the bay, the backyard slopes gracefully towards the water's edge with a new seawall. The professional landscape plan not only created beautiful grounds, but a number of entertaining and play areas, including a dining terrace with built-in barbeque/prep station. On the eastern side of the home, you are met by a sizeable driveway and a separate two car garage. Upon entering the front door, a beautiful onyx kitchen welcomes you. The charming dining room anchored by its fireplace, French doors face west, allowing you to take in the spectacular views. The cozy living room and its complementary fireplace. Through large French doors is an inviting covered terrace, making it the perfect place to entertain guests, or for intimate moments looking at sunsets over the bay. In addition to the stairs, all floors are accessible via a new elevator. The grand master bedroom comes complete with two large fully outfitted closets and a spa quality bathroom with unparalleled water views from shower and tub. A private balcony off the master offers the perfect place to enjoy a sunset or morning coffee. There are two additional bedrooms, a marble bath, and a small office on the second floor. The perfect weekend getaway or main residence this Centre Island home offers a turnkey option for any waterfront buyer could want. Truly A One-Of-A-Kind! Call For Details.

353 Centre Island Road, Oyster Bay
$1,298,000
4 Beds ⋅ 3 Baths ⋅ 1018691 MLS
Welcome to this classic Center Hall Colonial, perfectly situated in the heart of Oyster Bay. A charming front porch sets the stage for this timeless home, offering an inviting place to relax and enjoy the neighborhood. Inside a spacious and thoughtfully designed layout features generously sized rooms, creating an effortless flow for both everyday living and entertaining. Sun-filled living spaces combine traditional charm with comfortable functionality, formal living and dining rooms boast lovely, detailed millwork- making this home ideal for today's lifestyle. Step outside to a beautifully landscaped rear property, complete with a deck and hot tub overlooking lush specimen plantings - your own private retreat for outdoor dining, gatherings, or quiet moments surrounded by nature. Ideally located just minutes from Oyster Bay's beautiful beaches, vibrant shopping, acclaimed restaurants, parks and convenient transportation, this exceptional home offers the perfect blend of a classic layout, elegance, comfort and convenience.

6 W Oak Hill, Oyster Bay
$1,350,000
4 Beds ⋅ 4 Baths ⋅ 1017289 MLS
>>>>>SEALED BIDS 4pm THURSDAY, JULY 16tth>>>>> Welcome to one of the original homes built in Florence Park. It is an unusual community with a Neighborhood Association for its 88 homes. Dues are collected annually and are $30 per household. It covers a beach cleanup, a block party, and a holiday party. The Association has a private bay beach and small boat launching area. The home was built in 1920 and has the charm of the era. Enter through the front covered porch, which is a wonderful place to enjoy quiet summer days and to watch the fire flies light up the night. The Foyer opens into a bright Living Room with wood burning fireplace and century old sliding doors leading to the detailed Dining Room. Directly off the Dining Room is a large screened-in Porch where hours can be spent relaxing. There is a first class eat-in kitchen with marble counter tops and stainless steel appliances with gas cooking. The second floor encompasses the primary Bedroom with walk in closet and Bath, 2 well sized Bedrooms, a full Bath and Laundry. The third floor is spacious and paneled and provides an additional Bedroom and Bath. It is cooled by two window units. The basement is unfinished. The basement door gives access to the outdoor shower, deck and the yard. The basement shelving will remain. There is a second laundry in the basement. The yard provides room for flowers, vegetables and play space. The oversized two car garage with pull down stairs leads to a loft for storage. The garage has had many uses through the years. There is much to enjoy at the house and in the neighborhood. Swimming, kayaking, paddle boarding and sailing from the private neighborhood bay beach only minutes away. The Town of Oyster Bay provides many beaches on the Sound side on the North Shore and the Ocean on the South Shore. The property is convenient to schools, stores, beaches, tennis courts, picketball courts, Long Island Rail Road, restaurants and the library.

107 Sidney Street, Oyster Bay
$2,500,000
7 Beds ⋅ 5 Baths ⋅ 1009840 MLS
Short Sale - cash offers only- it is only unable to be financed. Offer subject to third-party approvals

1117 Cedar Ridge Road, Oyster Bay
$949,000
4 Beds ⋅ 2 Baths ⋅ 1009941 MLS
All Information Deemed Accurate But Should Be Independently Verified. **Nestled in a desirable Oyster Bay location, this beautifully updated split-level residence offers the perfect blend of timeless elegance and modern comfort.** Boasting 4 generously sized bedrooms and 2 tastefully renovated baths, the home features a thoughtfully designed layout with spacious, light-filled interiors ideal for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into inviting living and dining spaces, creating an effortless atmosphere for gatherings. Beautiful hardwood floors throughout the main level. A partial basement with a versatile bonus room provides exceptional flexibility, perfect for a private home office, fitness studio, media room, or guest retreat. Outside, the fully fenced property offers a private backyard oasis with ample space for relaxation and outdoor entertaining. Additional amenities include an attached garage and meticulous upkeep throughout. Ideally situated near Oyster Bay's charming waterfront, boutiques, restaurants, parks, and transportation, this exceptional home presents a rare opportunity to enjoy refined North Shore living in one of Long Island's most sought-after communities.

15 Wood Drive, Oyster Bay
$1,149,000
4 Beds ⋅ 3 Baths ⋅ 1008723 MLS
Welcome to 134 Singworth Street, Oyster Bay! Situated on a desirable corner lot, this spacious and well-appointed home offers the perfect blend of classic charm and modern comfort. A welcoming entry foyer leads to an elegant interior featuring hardwood floors, high ceilings, crown moldings, and hi-hat lighting throughout. The main level boasts a formal living room with a cozy gas fireplace, a private office, a comfortable den, a formal dining room, a well-equipped kitchen with a wine refrigerator, and a full bathroom—providing an ideal layout for both everyday living and entertaining. Upstairs, the primary suite serves as a private retreat, complete with its own full bathroom and an attached sunroom perfect for relaxing year-round. Three additional bedrooms and another full bathroom complete the second floor. A walk-up attic offers excellent storage potential. Additional highlights include a full unfinished basement with an outside entrance and laundry area, 200-amp electrical service, an updated boiler and hot water heater, roof is only 6 years old and a dual-zone HVAC system for enhanced comfort and efficiency. Step outside to enjoy the large backyard featuring a patio, ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. This exceptional Oyster Bay home offers abundant space, thoughtful features, and endless possibilities in a sought-after location. Don't miss this wonderful opportunity to make it your own!

134 Singworth Street, Oyster Bay
$799,000
3 Beds ⋅ 2 Baths ⋅ 1006593 MLS
Introducing 81 Summers...Welcome to this charming 3-bedroom, 2-bath colonial style home in the heart of desirable Oyster Bay! Boasting hardwood floors throughout, the entry foyer leads to a spacious living room, a formal dining room, and a kitchen with a pantry area. The finished basement features bilco doors for easy access and added convenience. Step out to a porch, and a tremendous yard, perfect for entertaining! With plenty of driveway parking leading to a two car garage, you're just moments away from downtown Historic Oyster Bay and all it has to offer -- beaches, parks, restaurants, and shops. Bring your TLC and make this home yours!

81 Summers Street, Oyster Bay
$1,225,000
4 Beds ⋅ 3 Baths ⋅ 990545 MLS
Nestled in Oyster Bay, this beautifully updated Cape-style home blends timeless coastal charm with modern comfort—just moments from the waterfront and vibrant downtown village. This spacious 4-bedroom, 2.5-bath residence offers a warm and inviting layout designed for both everyday living and entertaining. The sun-drenched family room with fireplace creates the perfect gathering space, while an additional den provides flexible living options for a home office or playroom. The large eat-in kitchen with adjoining dining area serves as the heart of the home, ideal for casual meals and hosting alike. Thoughtfully updated throughout, including the kitchen, baths and roof, the home also features new windows, soffits and extensive tree work completed in 2026—offering both peace of mind and enhanced curb appeal while preserving its classic character. Step outside to a private backyard oasis with a porch perfectly positioned to enjoy beautiful golden-hour sunsets and tranquil outdoor living. Additional highlights include a full, dry, ready to-finish basement. A rare opportunity to experience Oyster Bay living at its finest, with close proximity to the waterfront, shops, restaurants, LIRR and all the charm this coastal town has to offer.

1 Seawanhaka Place, Oyster Bay
$2,299,000
5 Beds ⋅ 5 Baths ⋅ 998428 MLS
Welcome to this stunning contemporary residence nestled in the prestigious Sherwood Gate community of Oyster Bay Hills. Situated on a breathtaking 2-acre property, this exceptional home offers over 5,038 square feet of luxurious living space designed for both elegant entertaining and everyday comfort. A dramatic two-story entry welcomes you into a sophisticated interior featuring a formal living room, dining room, private library, and an open-concept floor plan filled with natural light. The gourmet chef’s kitchen is beautifully appointed with premium Thermador appliances, a Sub-Zero refrigerator, quartz countertops, and a spacious Butler’s pantry, all seamlessly flowing into the inviting den with a cozy fireplace. The expansive primary suite is a true retreat, showcasing cathedral ceilings, dressing area, two oversized closets, and a spa-inspired en-suite bath. Three additional generously sized bedrooms include a dual-entry bath and an updated en-suite bathroom, providing comfort and privacy. Designed with convenience in mind, the home features two staircases leading to the second floor — one from the grand main entry and another from the kitchen area. The fully finished lower level offers exceptional bonus space including a recreation room, gym, abundant storage, additional entertainment area, and direct access to the garage. Step outside to your own private resort-style oasis. The spectacular backyard is an entertainer’s dream, highlighted by a magnificent custom-designed pool, elegant fire pit lounge area, and expansive grounds offering endless possibilities for relaxation and outdoor living. This extraordinary property combines timeless elegance, modern luxury, and unparalleled amenities in one of Oyster Bay Hills’ most sought-after communities

31 Sherwood Gate, Oyster Bay
$1,325,000
5 Beds ⋅ 5 Baths ⋅ 996701 MLS
Existing 3800 sq ft, second floor can be added for an additional 2800 sq ft. Total useable sq ft (with extension) can be above 6400 sq ft. Great Opportunity for extension: Total 2 acre land, you can extend and build your dream house as you like.

19 Tiffany Road, Oyster Bay
$1,550,000
5 Beds ⋅ 4 Baths ⋅ 992517 MLS
This beautifully appointed and meticulously maintained Oyster Bay residence blends thoughtful design with high end finishes across three spacious levels. Featuring hardwood floors throughout, five bedrooms and four full bathrooms. The home offers exceptional flexibility, including a first floor bedroom with attached en-suite bath with walk-in shower and attached den, perfect for extended guests. Three of the four bathrooms are en suite including a luxurious third floor primary retreat. The main living room is both grand and inviting, with soaring 11 foot ceilings, a gas fireplace with a custom mantel. A formal dining room with pocket doors leads to a gourmet kitchen with radiant heat and an eight foot island outfitted with quartz countertops. The island also offers an oversized prep-sink, microwave and additional seating. Completing the kitchen are two Bosch dishwashers, gas stove, wall oven, premium stainless appliances, pull out drawers, a double water filtration system, under counter lighting and a second oversized sink. An additional option for casual dining is an attached eat in kitchen area. A sun lit spacious den with French doors leads to an expansive outdoor setting, featuring an alfresco dining area, a brick patio, composite decking and a pebbled fire pit for cozy evenings. Completing the home is a full unfinished basement of over one thousand square feet of usable space, new windows, refinished cement stucco walls with high ceilings that leads to an underground attached two car garage. Central air conditioning, five zone heat, newly paved driveways, radiant heat in the foyer and kitchen, pull-down attic stairs with additional storage, surround sound speakers inside and out make this an exceptional home for elegance, entertaining and functionality. Please note some images include virtual staging.

2 W Oak Hill Drive, Oyster Bay
$3,800,000
5 Beds ⋅ 6 Baths ⋅ 983376 MLS
Enjoy the splendor and many amenities of your private country estate just an hour from Manhattan. This gorgeous property sits nestled in historic Oyster Bay Cove, the home of President Theodore Roosevelt’s Sagamore Hill. The home features 5 bedrooms and 6 baths and sits on an exquisitely landscaped nearly 4 acre parcel. Inside, sweeping staircases, cathedral ceilings and fine woodworking and cabinetry frame a perfect oasis for the family. Outside, among the wooded expanse are a swimming pool, tennis court and putting green. The home also boasts a gourmet kitchen, formal dining room, home theater, large office and 3 fireplaces.

10 Redmond Lane, Oyster Bay
$1,995,000
6 Beds ⋅ 6 Baths ⋅ 969523 MLS
Oyster Bay Cove Estate with Water Views This exceptional estate located in the bucolic community of Oyster Bay Cove has been completely and meticulously renovated over a two-year period and now features a brand-new Certificate of Occupancy for the home, barn, and site work. The residence has been structurally reinforced and certified to New York State standards, ensuring quality and longevity for generations to come. Set on 2.4 serene acres near the bay, the property blends old-world North Shore charm with luxurious modern upgrades, all thoughtfully designed with an elegant Hamptons-inspired aesthetic. Recent improvements include new electrical, plumbing, landscaping, flooring, bathrooms, kitchen, moldings, and structural upgrades. The grounds have been beautifully reimagined with red maple trees, screening trees, and curated plant specimens, creating a private and picturesque setting. The home is located within a historic North Shore community (not landmarked) and includes exclusive beach and mooring rights for residents of Oyster Bay Cove, offering easy access to boating, kayaking, and waterfront recreation on Oyster Bay. Inside, the residence offers warm elegance and modern comfort, including: • A chef’s kitchen with quartz countertops and premium appliances, perfect for everyday living and entertaining • An enclosed sunroom, providing cozy year-round enjoyment and stunning water views • A spacious primary suite featuring a spa-like bath and custom walk-in dressing room • A grandfathered third floor, ideal for a home office, studio, or additional guest accommodations Additional highlights include: • Separate renovated guest quarters with private entrance, kitchen, and bath • Large multi-purpose barn, a giant loft, and electricity • Natural spring-fed pond with fountain flowing directly toward the bay • Outdoor patio with fire pit, perfect for entertaining or peaceful evenings Residents enjoy the convenience of walking distance to town, where charming shops and renowned restaurants line the harbor in Oyster Bay. Located just 30 minutes from New York City, the property offers the feel of a Hamptons retreat with easy city access. The area is served by excellent schools and is close to several top-rated institutions. This rare property offers timeless character, tranquility, water views, and exceptional craftsmanship in one of the North Shore’s most desirable and appreciating communities.

77 Cove Road, Oyster Bay
$595,000
2 Beds ⋅ 2 Baths ⋅ 980900 MLS
Welcome to 46 Irving Place, a charming Colonial tucked away at the end of a quiet street in the heart of Oyster Bay. Perfectly situated just minutes from the train, waterfront, dining, and local restaurants, this home offers both convenience and character. Warm and inviting layout, where classic details blend seamlessly with everyday comfort. Two Bedrooms (possible 3) and 1.5 baths. Its prime location makes it ideal for those who want to enjoy all that this vibrant town has to offer—whether it’s an easy commute, a stroll to the harbor, or nights out at nearby eateries. A true Oyster Bay gem with the perfect balance of privacy and accessibility.

46 Irving Place, Oyster Bay
$1,200,000
4 Beds ⋅ 1 Baths ⋅ 978908 MLS
Location, location, location! This charming house is in beautiful Oyster Bay with private beach. Beautiful scenery, more than just a home, it's a way of life.

424 Centre Island Road, Oyster Bay
$1,850,000
4 Beds ⋅ 4 Baths ⋅ 945280 MLS
This beautiful standalone townhome is a perfect blend of modern elegance and timeless charm. One of the highly desireable cove models nestled in a serene neighborhood, it features a stunning facade and landscape, creating an inviting first impression. Inside, the open-concept design floods the space with natural light, highlighting the sleek hardwood floors that flow throughout. The spacious living area boasts high ceilings and large windows, offering picturesque views of the surrounding nature. Two contemporary fireplaces serve as a cozy focal point, ideal for gatherings with friends. The gourmet kitchen is a chef's dream, equipped with state-of-the-art appliances, quartzite countertops, and a generous island for meal preparation and casual dining. Adjacent to the kitchen, the dining area seamlessly connects to an outdoor patio, perfect for entertaining and alfresco dining with a natural gas BBQ. The luxurious primary suite located on the main level features walk-in closets and an en-suite bathroom with double sinks, two toilets, and a spacious stone tile and glass shower. Additional bedrooms are designed with comfort in mind, each with ample closet space and large windows. Outside, the private backyard is screened. This beautiful standalone townhome combines comfort, style, and a sense of community, making it the ideal place to call home. Two car attached garage wiht expoxy floor. Close to all. Full house back up automatic generator.

38 Fieldstone Lane, Oyster Bay
$6,995,000
5 Beds ⋅ 7 Baths ⋅ 914210 MLS
On the tranquil shores of Cove Neck in Oyster Bay, this extraordinary waterfront estate offers something increasingly rare: two private acres, 200 feet of shoreline, and panoramic views of the Long Island Sound that greet you from virtually every room in the house. Set just minutes from the charming villages of Oyster Bay and Huntington, with their acclaimed restaurants, boutique shopping, and vibrant waterfront dining, and fifteen minutes to the LIE, this is a property that offers the serenity of a private resort with the convenience of everything the North Shore has to offer. Hamptons Living Closer to NYC. The residence spans more than 9,000 square feet and was designed for those who want to live at full scale. A dramatic entry foyer opens into expansive living areas anchored by floor-to-ceiling windows framing the water. The formal living and dining rooms, a sophisticated lounge, and a 1,600 square foot great room with wet bar and wood-burning fireplace create a seamless flow for entertaining. A library with its own bath offers a quiet retreat on the main level. Upstairs, three ensuite bedrooms each open to private balconies overlooking the Sound. The primary suite is a sanctuary of its own, with a fireplace, spa bath with dual vanities, and an oversized walk-in dressing closet. Every room. Every view. The chef's kitchen is equipped with granite counters, custom cabinetry, and professional appliances including three ovens and two dishwashers. The lower level extends the lifestyle further with an indoor pool and hot tub, an entertainment space with wet bar, a full guest suite with private entrance, and a 4-car garage. Outside, more than 1,800 square feet of wraparound decking, a tennis court, a gazebo, and direct water access for kayaking and jet skiing complete a property that operates entirely on its own terms. This is waterfront living on the North Shore at its most complete.

26 Tennis Court Road, Oyster Bay
$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
$999,000
4 Beds ⋅ 3 Baths ⋅ 898143 MLS
Fully Renovated & Move-In Ready Split-Level Home! Welcome to this beautifully updated split-level residence that perfectly blends modern comfort with timeless charm. Featuring 4 spacious bedrooms and 2.5 well-appointed bathrooms, this home is thoughtfully designed to suit today’s lifestyle.Step into a sun-filled, open-concept layout showcasing a stylish living room, formal dining area, cozy family room, and a modern eat-in kitchen with sleek finishes—ideal for both everyday living and entertaining. Elegant hardwood floors, recessed lighting, and tasteful upgrades throughout add warmth and sophistication.The fully finished basement offers versatile space for a home office, playroom, or media lounge, providing flexibility to meet your needs. Outside, enjoy a lush, private backyard perfect for relaxing, gardening, or hosting gatherings.Additional conveniences include a private driveway and ample street parking. Located near top-rated schools, parks, shopping, and major amenities, this move-in-ready gem offers the perfect combination of space, style, and location.Don’t miss the opportunity to make this exceptional home yours!

16 Huckleberry Lane, 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.