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$1,250,000
4 Beds ⋅ 3 Baths ⋅ 1048168 MLS
This beautifully reimagined Colonial blends historic Oyster Bay character with the comfort and sophistication of extensive modern updates.Thoughtfully renovated throughout, the home features comprehensive interior and exterior improvements while preserving the warmth and character of its original architecture. Wood floors flow throughout the home, complemented by Andersen windows that bring in abundant natural light. The beautifully updated kitchen is appointed with Viking stainless steel appliances, custom cabinetry and designed for both everyday living and entertaining. With four bedrooms and three full baths, the home offers a flexible and well-proportioned layout suited to today’s lifestyle. A newly fully fenced backyard, landscaping and patio are an ideal setting for outdoor dining, entertaining, or simply relaxing at home. Sprinklers throughout the property. A rare opportunity to enjoy the character of a classic Oyster Bay Colonial with the benefit of extensive modern updates, all within one of Long Island’s most storied villages.

61 Anstice Street, Oyster Bay
$999,000
4 Beds ⋅ 4 Baths ⋅ 1025962 MLS
Beautifully renovated 4-Bedroom,3.5-Bath Colonial in the Heart of Oyster Bay. Completely renovated in 2024, this stunning Colonial combines timeless charm with modern finished. A welcoming wraparound front porch along with a fully fenced yard, creating the perfect place to relax and enjoy the neighborhood or have your privacy. Step inside to discover an inviting angled bay window, creating a cozy reading nook or sitting area. The spacious eat-in kitchen features marble countertops, abundant cabinetry, and plenty of room for everyday dining and entertaining. A convenient laundry room is located just off the kitchen, with direct access to the patio for fun and entertaining. An inviting dining room, with a door leading onto the wraparound porch. The second floor offers a luxurious primary suite with a spa-inspired bath featuring a freestanding soaking tub and floor-to-ceiling marble finishes. Two additional bedrooms and a beautiful appointed full hall bath complete this level. The above grade lower level provides exceptional additional living space, including a comfortable den with a fireplace, a full bathroom, generous storage, and a private entrance to the side yard-ideal for guests, a home office or recreation. This move-in-ready home offers the perfect blend of comfort, style and location in the heart of Oyster Bay.

58 Summit Street, Oyster Bay
$979,000
3 Beds ⋅ 2 Baths ⋅ 1050245 MLS
Single level living at its finest! This updated and meticulously maintained ranch home features three bedrooms and two full bath, including a primary en-suite. It is a perfectly situated residence offering proximity to shopping, top-rated schools, and everything that living next to the charming village of Oyster Bay brings, including fine dining, parks and beach. It provides the perfect blend of comfort and functionality. The sunny and bright kitchen is thoughtfully updated with ample space for casual dining, beautiful natural wood cabinetry, granite countertops and brand new appliances. Formal Living Room and spacious Dining Room with crown molding and gleaming hardwood floors, lead into a cozy den with a woodburning fireplace and sliders to a fabulous bonus room with glass walls. And there’s more….a large basement, the full length of the house, provides additional room for entertaining and plenty of storage including a huge walk-in pantry and cedar closet. The professionally landscaped property is ideal for summer fun and is a gardener’s delight. Special highlights include *gas furnace *gas powered Generac generator *updated electric *CAC *CVAC *IGS *two-car garage with polyurea garage flooring *Andersen windows

24 Peerless Drive, Oyster Bay
$1,398,000
4 Beds ⋅ 3 Baths ⋅ 1050679 MLS
Picture-perfect and beautifully renovated, this 4-bedroom, 2.5 bath Colonial is located in Oyster Bay's sought-after Forest Estates private pool community. Thoughtfully updated throughout, the home combines sophisticated finishes with a wonderful open floor plan designed for both everyday living and entertaining. European white oak floors flow throughout the home. The spacious living room features a wood-burning fireplace and a wall of windows that fills the space with natural light, while sliding doors open to a Trex deck and an exceptional, retreat-like backyard. The beautifully landscaped outdoor setting features a new heated in-ground vinyl pool, outdoor bar,expansive new terraces, new retaining walls, handsome masonry and a 7-zone irrigation system-creating an incredible setting for outdoor entertaining and relaxation. The chef's eat-in kitchen is beautifully appointed with quartzite countertops, a large center island, stainless steel appliances, wine refrigerator, abundant cabinetry and chic lighting. The adjoining dining room features a bay window and custom built-ins with quartz countertops, providing both stylish display space and excellent storage. Upstairs, the spacious primary bedroom offers a lovely bay window and en-suite bath with double vanity. Three additional bedrooms and a beautifully updated hall bath complete the second floor. Additional amentites include Lutron Caseta smart lighting, smart thermostats, a finished lower-level media room/play room with built-in air humidifier system, new hot water tank and attached 2 car garage. Enjoy the privacy of your own backyard oasis along with membership in the desirable Forest Estates private pool community. A truly special, move-in-ready Oyster Bay home offering exceptional indoor-outdoor living, modern conveniences and timeless style. Permanent outdoor fire pit.

10 Hilltop Lane, Oyster Bay
$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
$1,979,000
3 Beds ⋅ 4 Baths ⋅ 1042505 MLS
Impeccably maintained and thoughtfully designed, this expanded Cove model offers beautifully appointed living spaces throughout. A light-filled, spacious entry welcomes you into the home, with a formal living room to the left featuring vaulted ceilings and French doors opening to the deck, and an elegant dining room to the right highlighted by a stunning coffered ceiling. The inviting eat-in kitchen is designed for both everyday living and entertaining, with crisp white cabinetry, gas cooking, generous storage, and an adjacent dining area and family room. The family room is anchored by a woodburning fireplace surrounded by extensive built-ins, creating a warm and comfortable gathering space. A conveniently located laundry/mudroom offers direct access to the two-car garage. The first-floor primary suite offers exceptional convenience and privacy, with dual closets and a luxurious en-suite bath featuring a soaking tub, walk-in shower, and separate water closet. Upstairs, an impressive office with a coffered ceiling is complemented by an adjacent sitting area overlooking the main level, along with two spacious en-suite bedrooms. The walk-out lower level provides even more flexibility, with abundant space for recreation, storage, or future customization and direct access to the patio. Located on private road in Fieldstone Homeowners Association $595/monthly (dues) which includes snow removal, landscaping and common area maintenance.

3 Fieldstone Lane, 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
$899,000
3 Beds ⋅ 3 Baths ⋅ 1030222 MLS
Beautifully renovated and filled with natural light, this exceptional Victorian is set on a picturesque property in the heart of Oyster Bay. Thoughtfully updated while preserving its original character, the home showcases updated kitchen and baths, freshly painted rooms, timeless architectural details and incredible backyard gardens. The main level offers an ideal layout for today's lifestyle, featuring a spacious chef's eat-in kitchen with pantry, a full bath, formal living and dining rooms, a welcoming family room, and a private office or gym perfect for working from home. Upstairs, the expansive primary suite serves as a peaceful retreat with a beautifully updated en-suite bath. Two additional bedrooms and another renovated full bath complete the second floor. A finished third-floor bonus space provides endless possibilities as a playroom, studio, guest area, or additional office. Also has EV Charger. Combining historic elegance with modern updates, this move-in ready home offers the perfect blend of character, comfort, and convenience just moments from Oyster Bay's vibrant downtown, restaurants, shops, parks, beaches, and the LIRR.

51 Tooker Avenue, 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
$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
$749,000
3 Beds ⋅ 2 Baths ⋅ 1006593 MLS
Price Reduction!!! 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
$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
$3,480,000
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
$1,200,000
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
$1,150,000
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.