$950,200Average Value$599Average Price per Sq Ft23Homes 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
Kieran Rodgers,
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 70 days on the market compared to the national average of 54 days. The median sale price for homes in Oyster Bay, NY over the last 12 months is $1,475,000, down 10% from the median home sale price over the previous 12 months.
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
Don’t miss this stunning, recently fully updated and sun-drenched 4-bedroom, 4-bathroom residence located in the highly desirable Jericho community and award-winning Jericho School District. Designed with both comfort and sophistication in mind, the home features a bright, open floor plan and beautifully proportioned living spaces. The designer kitchen showcases custom cabinetry, quality
Calling all investors and first-time homebuyers! Enjoy super low taxes and one of the lowest carrying costs in Jericho.This stunning fully renovated residence has been completely updated from top to bottom within the past two years and offers the rare advantage of true move-in-ready luxury living. Designed for both comfort and efficiency, the home features a brand-new roof with solar panels, a
Welcome to this wonderful 5 bedroom, 3.5 bath Colonial which is set on one of Syosset's most desirable streets, convenient to the Long Island Railroad, Village Elementary, shopping and houses of worship. The main level features a dining room and living room, a young eat in kitchen which offers a traditional layout- perfect for entertaining and daily living. There is a generously sized den with a
Welcome home to this beautifully renovated four-level residence, offering modern luxury and true move-in-ready convenience. This bright, open-layout home features brand-new oak hardwood floors, recessed lighting, and a stunning designer kitchen crafted to impress. The kitchen is outfitted with quartz countertops, two-tone shaker cabinetry, a subway tile backsplash, a Samsung gas range, Samsung
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
Welcome to your dream home in the exclusive enclave of Old Harbour Green, complete with deeded rights to the Harbour Green Shore Club and Marina. Situated mid-block in this pristine waterfront community, this sprawling split-level residence offers the perfect blend of comfort, space, and lifestyle. A large, welcoming foyer sets the tone as you enter this beautifully maintained home, featuring
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
Don’t miss this stunning, recently fully updated and sun-drenched 4-bedroom, 4-bathroom residence located in the highly desirable Jericho community and award-winning Jericho School District. Designed with both comfort and sophistication in mind, the home features a bright, open floor plan and beautifully proportioned living spaces. The designer kitchen showcases custom cabinetry, quality
Welcome to 11 Buckingham Ct — an exceptional Colonial-style residence in the prestigious gated community of Stone Hill, Muttontown. This one-of-a-kind, custom-built young home offers approximately 5,500 sq. ft. of refined living space, seamlessly blending timeless architecture with modern luxury. The impressive entry sets the tone for this elegant yet inviting residence. Step inside through the
Calling all investors and first-time homebuyers! Enjoy super low taxes and one of the lowest carrying costs in Jericho.This stunning fully renovated residence has been completely updated from top to bottom within the past two years and offers the rare advantage of true move-in-ready luxury living. Designed for both comfort and efficiency, the home features a brand-new roof with solar panels, a
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 with a warm living room, eat-in kitchen, and
Welcome home to 203 Woodbury Road! This expansive 5-bedroom, 3-full-bathroom Hi-Ranch offers over 2,600 square feet of versatile living space. Built in 1988, this incredible property has been lovingly maintained by its original owners and pride of ownership truly shines throughout. A standout feature of this home is the highly desirable main-level layout. It boasts a spacious first-floor bedroom
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 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
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.
Recent Renovation, Hardwood Floors Use Of Yard, Tenant Storage And Off Street Parking. Laundry Area. Near Village And Park. 1 Month Security, Tenant Pays Own Gas And Electric Renters Insurance Required. Credit Check.
Great Apartment In Village, Hardwood Floors, Recent New Lighting Installed Private Entrance. Tenant Pays Own Gas And Electric, 1 Month Security Deposit. Renters Insurance Required.
Beautifully updated pet-friendly 3-Bedroom, 1-Bath ground-floor rental in the heart of Hicksville! This spacious first-floor unit in a well-maintained two-family home features a brand-new kitchen with modern finishes, a completely renovated bathroom, and newly refinished hardwood floors throughout. Enjoy a bright eat-in kitchen perfect for everyday living and entertaining. Additional highlights
For Rent – Entire House with Finished Basement, Garage & Large BackyardLocated at 46 Elmira Street in Hicksville, this spacious entire home for rent offers generous indoor and outdoor space.The property sits on a 120 ft × 120 ft lot and features a large backyard, providing ample outdoor space for recreation or relaxation. The home also includes a garage, and additional parking may be
This stunning ranch in the Gates of Woodbury sits on a full acre of landscaped property, offering a rare combination of elegance, comfort, and resort-style amenities. Inside, you’ll find 4 spacious bedrooms and 3 full bathrooms, thoughtfully designed for both relaxation and convenience. The open-concept kitchen is a chef’s dream, featuring sleek new stainless steel appliances, ample cabinetry,
Move right into this pet-friendly, freshly renovated 5-bedroom, 2-bath expanded Cape for rent in Hicksville, set on an oversized lot with a full basement and a new oversized driveway offering plenty of off-street parking. The new kitchen offers contemporary finishes and flows seamlessly into the spacious living and dining areas. With bedrooms on both levels, the home provides a flexible layout
BEACHFRONT BLISS on Long Island Sound! The main home offers 2 BRs and 2.5 Baths, listed for $6500/mo, and the separate 1-BR cottage can be included for ADDITIONAL rent. This totally rebuilt residence offers amazing 180-degree views of Long Island Sound with spectacular sunsets and access to the beach right in your own backyard!Located in the exclusive Pine Lane HOA, this home is part of the
Welcome to the mint condision colonial in Jericho! Renovated eat-in kitchen with many updated finishes. Spacious living room and den. Convenient first-floor powder room. Three generously sized bedrooms. Fully finished basement offers additional living or recreational space. Close to schools, library, grocery stores, and other local conveniences. Gas cooking & heating, Central AC, 1 car garage
Welcome home to this stunning one family for rent. Recently updated, with 5 spacious bedrooms, dining/living area, spare room, 2 full bathrooms, new kitchen, storage, driveway, & yard. Walking distance to schools. Close to shopping and highway. Whole house for rent; renter is responsible for snow removal, garbage, lawn, & utilities.
Located in Glen Head, situated in a cul-de-sac block. The main floor showcases a gracious Living Room, a well-appointed Eat-In-Kitchen, a formal Dining Room, an elegant Wet-Bar, a Full Bath, and a conveniently situated Laundry Room. A standout feature of the residence is the inviting and expansive Den, complete with a fireplace, adorned with cathedral ceilings, skylights, and sliding doors that
Great Location With Long Island Sound At End Of Block With Beach Rights. Spacious Colonial With Formal Living Room And Dining Room. 1 Month Security Tenant Pays Their Own Gas, Electric And Water. House Has Solar Panels Which Lowers The Electric Bills. Renters Insurance Required.
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