Oyster Bay Real Estate

Welcome to Oyster Bay, a picturesque gem nestled on the North Shore of Long Island, New York, in the heart of Nassau County. This charming town is steeped in rich history and natural beauty, making it a perfect destination for those seeking a vibrant community with a touch of coastal elegance.

Oyster Bay is renowned for its stunning waterfront views, where the serene waters of the bay meet lush landscapes. The town is a haven for outdoor enthusiasts, boasting an array of parks, hiking trails, and recreational activities. Enjoy a leisurely stroll along the scenic Oyster Bay Harbor or explore the expansive trails of the nearby Planting Fields Arboretum, where seasonal blooms bring the gardens to life.

History buffs will appreciate Oyster Bay’s storied past, highlighted by the legacy of Theodore Roosevelt, the 26th President of the United States, who was born here. The town is home to the Theodore Roosevelt Sanctuary and Audubon Center, where visitors can learn about wildlife conservation while enjoying the beauty of nature.

In addition to its natural allure, Oyster Bay offers a charming downtown area filled with unique boutiques, delightful cafes, and fine dining options. The local community is vibrant, hosting various events throughout the year that celebrate the arts, culture, and the spirit of togetherness.

With its blend of scenic beauty, rich history, and a welcoming community, Oyster Bay is more than just a place to live; it’s a lifestyle. Discover your dream home in this enchanting town and experience the warmth and charm that Oyster Bay has to offer.

Newest Listings in Oyster Bay

$975,000

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

$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 winter water 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

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, pickleball courts, Long Island Rail Road, restaurants and the library.

107 Sidney Street, Oyster Bay

$375,000

1 Beds ⋅ 1 Baths ⋅ 1013323 MLS

Welcome to Lexington Estates in the heart of Oyster Bay! This bright & spacious corner one bedroom co-op offers an abundance of natural light, a desirable open layout, and the added privacy of a corner location. Featuring hardwood floors, oversized windows, a generously sized living room and dining area, and a well-appointed kitchen, this home provides comfortable everyday living. Nestled within a beautifully maintained garden-style community with landscaped grounds, residents enjoy on-site laundry, storage, & ample parking. Conveniently located just moments from Oyster Bay Village, restaurants, shops, parks, beaches, marinas & the LIRR, offering an ideal blend of North Shore charm & commuter convenience.

200 Lexington Avenue Unit #8B, Oyster Bay

$304,999

1 Baths ⋅ 1014455 MLS

Beautifully landscaped and well maintained co-op apartment complex with walkways, patios and sitting areas with on-site superintendent. Second floor studio with high ceilings, 1 AC, open layout, and kitchen with stainless steel appliances. Basement common level offers storage and laundry facilities including bicycle storage room. Conveniently located in the heart of Oyster Bay which is in close proximity to beaches & parks, tennis courts, baseball fields, restaurants, shops, schools, recreational clubs and the Long Island Railroad. Maintenance fee includes taxes, heat, water, garbage removal, landscaping, snow removal, and parking.

200 Lexington Ave Unit #12E, 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

$489,000

2 Beds ⋅ 1 Baths ⋅ 1010580 MLS

Welcome To Top Of The Harbour In The Heart Of Beautiful Oyster Bay! Pristine And Thoughtfully Designed Two Bedroom, Second Floor Corner Unit, With Harbor Views From Balcony. The Eat In Kitchen Boasts Quartz Counters, Tile Flooring, Stainless Steel Appliances And Large Pantry. An Open Plan DR/LR Offers Elegant Hardwood Floors And Crown Molding. The Primary Bedroom Is Spacious, Detailed With Crown Molding And Oyster Bay Harbor View. A Generous Sized Second Bedroom Offers Large Closet Space And Crown Molding. Other Features Include A Walk In Hall Closet, Newer AC Units And Ceiling Fans. Convenient To Charming Historic Oyster Bay With Shops, Restaurants, Park, Waterfront And LIRR.

11 Harbour Lane Unit #1B, 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. ***The oversized deck has been removed to create a larger yard***. 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

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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.