$977,334Average Value$615Average Price per Sq Ft28Homes For Sale
Oyster Bay is rich with Colonial secrets
With a history steeped in a famous Revolutionary War spy ring’s accomplishments, it’s perhaps fitting that Oyster Bay remains a well-kept secret. At first glance, few would suspect the small hamlet played such an essential role in the Revolutionary War, but it was here that the Queen’s Rangers, led by Lieutenant Colonel John Graves Simcoe, were stationed in the home of Samuel Townsend. Samuel Townsend’s son, Robert Townsend, was a member of George Washington’s famous Culper Spy Ring, though he was so secretive that his role in the ring wasn’t discovered until the 1930s. Townsend’s sister, Sally, may also have been a spy for the ring, and it was in this home that legends say she overheard Simcoe and Adjutant General John André discussing the plan for Benedict Arnold to turn West Point over to the British. Regardless of how the information was gathered, Robert reported it to Washington, preventing the capture of the fort and leading to André’s arrest. The home, which was built in 1740, still stands with a second lease on life as the Raynham Hall Museum. Today, Oyster Bay remains a small, almost sleepy hamlet with a diverse selection of restaurants and a large park along the harbor.
Lean about the rich history Oyster Bay at the Raynham Museum.
A lot can be learned from a quick trip to the Oyster Bay Historical Society.
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Swimming and playing sports at Theodore Roosevelt Memorial Park
Theodore Roosevelt Memorial Park, named for the U.S. president who made his home in nearby Cove Point, hugs the coast. The park offers sandy beaches, soccer and baseball fields, tennis and basketball courts and a playground. Locals can also use the marina and boat launches to get out onto the harbor. “It’s one of the prettiest places, I think, on Long Island,” says Mara Navaretta, broker for Homes by Mara Realty, who’s been selling properties in the area since 1997. “The park is all waterfront and just gorgeous. You can see all the big, beautiful boats and feel the breeze from the ocean.” Just south of the neighborhood, Pine Hollow Club has an 18-hole golf course, tennis, pickleball and padel courts. Roosevelt's home, Sagamore Hill, is part of a national historic site that's 2 miles north, and has a museum and nearly 2 miles of nature trails.
Shoot and score at the athletic fields at Roosevelt park in Oyster Bay.
Oyster Bay residents enjoy the peach and tranquility of Theodore Roosevelt Park.
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Colonial-style homes starting in the $500,000s
Streets are lined with colonial-style, simple folk Victorian and bungalow Craftsman homes, many featuring large front porches. Most homes sit in traditional suburbs with cul-de-sacs, but there are also a few waterfront properties available. Homes from the early-to-mid 20th century typically sell for $500,000 to $900,000, while houses from the late 20th century usually go for $1 million to $1.5 million. “And what’s also good about Oyster Bay real estate-wise, is it’s also one of the few places around us that has a lot of legal two-families,” says Navaretta. “So, if anyone’s looking to increase their investments, they should come to Oyster Bay.” These one-to-two-bedroom properties tend to sell individually for $250,000 to $500,000. The CAP Index gives Oyster Bay a crime score of 2 out of 10, lower than the national average of 4.
Oyster Bay offers many older and newer colonial styled homes alike.
Many homes in Oyster Bay feature a Gambrel roof often with dormers for added living space.
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Top grades for Oyster Bay-East Norwich Public Schools
Students may start at Theodore Roosevelt Elementary, which earns an A from Niche, for kindergarten through second grade, before going to James H. Vernon School, which also gets an A, for third to sixth grade. Seventh through 12th graders attend Oyster Bay High, which receives an A-minus and operates with a student-to-teacher ratio of 8-to-1.
Theodore Roosevelt Elementary School in Oyster Bay has a student to teacher ratio of 11 to 1.
Oyster Bay High School receives an A- rating from niche.com.
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Summer events in downtown Oyster Bay
From June to July, the Oyster Bay Music Festival hosts emerging artists at the Christ Church of Oyster Bay. The concerts are free, and there are also lectures and master classes open to the public throughout downtown. Also in July, St. Rocco’s Festival is a four-day event celebrating the area’s Italian heritage. The festival features carnival rides, food trucks, games, live music and a fireworks show.
This original '65 Mustang hails from Santa Monica, CA for the Oyster Bay Cruise Night.
Enjoy a free concert at the Oyster Bay Music Festival in Oyster Bay.
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Shopping and dining along Pine Hollow Road
Along Pine Hollow Road, there’s a Stop & Shop for groceries and Mario’s Pizzeria, which has been serving the area since 1969. There are also sit-down restaurants near South Street, including Taby's Burger House for classic American food and Home Sweet Home Cafe for Chilean dishes. Another popular choice is The Homestead, whose cozy tavern atmosphere, bar and live music have been a staple of the community since 1896.
Pop into Mario's Pizza in Oyster Bay for take out or a sit down meal.
Shoot and score at the athletic fields at Roosevelt park in Oyster Bay.
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Commuting to Manhattan on the Long Island Rail Road
Oyster Bay residents can walk or bike to nearby shops and parks but may still want a car to explore the rest of Long Island. Oyster Bay’s train station connects the community to Manhattan via the Long Island Rail Road, with the ride taking about 80 minutes.
Head to the city or out east from the Oyster Bay train stop.
All aboard at Oyster Bay Train Station.
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Written By
Logan Soter-Reardon
Photography Contributed By
Jeff Rainone
Video By
Jackson Nacey
Interested in learning more about homes in this area?
Reach out to
Karyn Dietrich,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Oyster Bay, NY sell after 82 days on the market compared to the national average of 56 days. The median sale price for homes in Oyster Bay, NY over the last 12 months is $1,492,500, down 10% from the median home sale price over the previous 12 months.
Beautiful completely remodeled Waterfront Colonial. New kitchen, baths, hardwood flooring w/new gas heating.& hot water. Massapequa District 23 schools w/extras including new windows, carpeting, paver patio & all appliances. Newer bulkheading on wide canal suitable for large watercraft. No water intrusion in the house from Hurricane Sandy w/$742 annual flood insurance quote on file !
Nestled in the prestigious community of Old Westbury, 32 Valley Road is a recently renovated 5-bedroom, 3.5-bath residence offering approximately 3,900 sq. ft. of refined living space designed for comfort and entertaining. Sun-filled interiors and an open layout create a seamless flow throughout the home. The main-level primary suite features a walk-in closet and spa-like ensuite bath. Two
Completely redesigned and renovated, this exceptional home offers 5 spacious bedrooms and 3 full bathrooms, set on an expansive ~10,000 sq ft property featuring a beautiful backyard pool. Upon entry, you’re welcomed by a dramatic open floor plan with a stunning porcelain heated tile floor and a thoughtfully designed open kitchen—the true heart of the home. Oversized windows with transoms, custom
Welcome to this spacious 4-bedroom, 3 full bath Splanch located in the highly sought-after Fams Development of Plainview. Offering a mix of open space and privacy, this home is designed for both comfortable everyday living and effortless entertaining. The main living area features an open, airy feel with sliding doors leading to an oversized deck and private backyard, creating a seamless
This beautifully maintained ranch offers the perfect blend of comfort and modern updates. Featuring stunning oak floors throughout, the home is equipped with three ductless A/C and heat units for year-round comfort. The updated kitchen boasts granite countertops and stainless steel appliances, a renovated bath, oil boiler, 150 amp electric service, and a nicely finished full basement offering
Beautiful completely remodeled Waterfront Colonial. New kitchen, baths, hardwood flooring w/new gas heating.& hot water. Massapequa District 23 schools w/extras including new windows, carpeting, paver patio & all appliances. Newer bulkheading on wide canal suitable for large watercraft. No water intrusion in the house from Hurricane Sandy w/$742 annual flood insurance quote on file !
This is an excellent opportunity to own a beautiful home with a stunning backyard oasis featuring a pool, located in the award-winning Jericho School District. Nestled in a peaceful neighborhood, the inviting living room flows seamlessly into the brand-new kitchen, which opens to an oversized patio and backyard—perfect for entertaining and relaxation. The home offers 4 spacious bedrooms and 2.5
Welcome to 20 Sagamore Way, Jericho — a beautifully appointed home offering comfort, space, and luxury living. This residence features 4 spacious bedrooms and 2.5 bathrooms. The first floor offers a private office room, perfect for working from home. Enjoy a chef’s kitchen equipped with stainless steel appliances, a pantry room, and ample cabinetry. The main level also includes a formal dining
Designer Showplace! Experience the pinnacle of refined living in this top-of-the-line expanded ranch, ideally situated mid-block in Muttontown with Jericho SD. Thoughtfully designed with both elegance and modern convenience in mind, this exceptional home showcases superior craftsmanship and meticulous attention to detail throughout. A dramatic vaulted grand foyer and living room set the tone upon
Welcome To A TRUE SHOWCASE In The Heart Of Locust Valley - PRIVATE CUL-DE-SAC LOCATION -Where Luxury, Scale, And Lifestyle Converge. This Extraordinary Estate Offers The Perfect Blend Of Classic Charm And Modern Comfort - An Unparalleled Living Experience, Combining Sophisticated Design With Resort-Style Amenities. Thoughtful Details And High-End Finishes Are Evident Throughout The Home.A
Nestled in the prestigious community of Old Westbury, 32 Valley Road is a recently renovated 5-bedroom, 3.5-bath residence offering approximately 3,900 sq. ft. of refined living space designed for comfort and entertaining. Sun-filled interiors and an open layout create a seamless flow throughout the home. The main-level primary suite features a walk-in closet and spa-like ensuite bath. Two
A Private Waterfront Estate of Distinction! Set behind the gates of the prestigious Hamlet Estate and overlooking tranquil pond vistas, 50 Holiday Pond is a rare expression of architectural elegance and modern indulgence—crafted for those who expect nothing less than exceptional. Spanning approximately 6,000 square feet of total living space, this custom-built Colonial residence unfolds with
A True Unicorn in Plainview!Discover this stunning fully renovated 3-bedroom, 2-bathroom ranch set on an expansive 1/3-acre lot located in a highly sought-after school district graded A+ by Niche. This home offers the perfect blend of privacy, flexibility, and modern living. Featuring an open-concept main level, split air conditioning units, recessed LED lighting throughout, an attached
Some homes just feel happy the moment you walk in — and this light-filled Sea Cliff village charmer is one of them.Highlights: Sun-drenched interiors. Flexible finished basement space. Spacious, fully fenced backyard. Detached garage and ample parking. North Shore School District. A bright, enclosed porch welcomes you in, leading to the first floor, where a warm living room, an eat-in
Welcome to 227 Prospect Avenue in Sea Cliff—a meticulously rebuilt residence that blends thoughtful designwith exceptional craftsmanship. This inviting home, spanning 5,180 square feet, marries modern efficiency withall-new systems: HVAC, electrical, plumbing, certified septic system, dry wells, and a full generator.Rich oak hardwood floors, laid in custom herringbone patterns, set an
Discover your dream retreat at 4 Shorewood Drive in Bayville! This gorgeous 4-bedroom, 2-bathroom home perfectly combines comfort and luxury in a peaceful setting. Fully furnished (if necessary) and ready for you to move in, it features a private yard and exclusive access to your private beach—perfect for soaking in those spectacular sunsets. We’re pet-friendly and welcome your dog to join the
This fully renovated 3-bedroom, 2-bath ranch is situated on an oversized lot and offers modern comfort with high-end finishes throughout. Located in Plainedge Schools and close to shopping. From the moment you enter, you'll notice the attention to detail and quality workmanship in every corner of the home. The kitchen features brand-new white shaker cabinets, sleek quartz countertops, and
Amazing luxury residence directly across from the Long Island Sound. Brand new in 2020. 2 bedrooms, 2 full baths, gourmet kitchen with granite counters. Wood floors, central A/C, heat and vacuum. Tankless hot water heater. Private deck and elevator. Includes private parking space.
ELEGANT LIVING IN A BEAUTIFUL CLEARVIEW VILLAGE SPLIT, FURNISHED. This beautiful split offers a perfect blend of comfort and style. Thoughtfully designed with tasteful furnishings throughout, the house has 3 bedrooms with 2 and a half bathrooms, a large den with a powder room, a warm, inviting sunroom that opens out into a paved patio, and a gorgeous, treelined, beautifully landscaped backyard.
Welcome to this beautifully maintained split-level house in the heart of Syosset. Featuring 4 bedrooms & 2 full baths, 244 Martin Drive has central air conditioning, gas cooking & heating, inground sprinkler system, and a fully-fenced in backyard. It is conveniently located near the elementary school, a variety of eateries, grocery stores, shops, and major highways. Better yet, the school
Welcome to 210 Fulton Street Apt. 1F - Perfectly situated in the heart of Farmingdale, Kingswood Garden Apartments offers exceptional convenience just minutes from the LIRR, vibrant Farmingdale Village, Bethpage State Park, and the renowned Bethpage State Golf Course. Surrounded by beautifully maintained grounds, the community features inviting outdoor sitting areas—perfect for relaxing
Water View Apartment For Rent Just Renovated. Great Space With Hardwood Floors And Heat Included. Lots Of Closets, Located On The First Floor. 1 Month Security, Renters Insurance Required. Credit Check.Appointments Set By Phone Call To Office Only.
Modern Living in Syosset’s Best Location! Welcome to 20 Cherry Lane — where style meets comfort. This stunning home offers a chef’s kitchen with stainless steel appliances, spacious sunlit rooms, finished lower level and a beautifully landscaped yard. Located in the prestigious Syosset School District, close to everything. Perfect for those seeking space, luxury and convenience.
Glen Head – Beautifully updated 2-bedroom, 1-bath home in a convenient Glen Head location close to the LIRR, local shops, restaurants, and schools. This bright and inviting home features a spacious open floor plan that’s great for everyday living and entertaining. The modern kitchen is the centerpiece of the home, complete with a large island with seating, granite countertops, and stainless steel
Tucked away on a quiet lane in the heart of Glenwood Landing, 2 Ruth Lane offers true privacy and sun-drenched rooms. This charming home features an open living and dining area that’s perfect for relaxing or entertaining, with natural light pouring through large windows. The updated kitchen has a large bay window, which is the ideal spot to read a book while dinner cooks. The backyard is fully
Ground Floor Apartment With New Eat In Kitchen, Large Living Room. Washer And Dryer In Unit With Heat Included And Use Of Yard, 2 Off Street Parking Spots 1 Month Security Tenant Pays Own Electric. Renters Insurance Required, Credit Check.Call Office To Set Up A Appointment.
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