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$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
$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
$1,149,000
4 Beds ⋅ 3 Baths ⋅ 1026156 MLS
Welcome to 43 Kellogg Street, a Wonderful Blend of Historic Charm and Contemporary Living Located in the Heart of Oyster Bay. At First Glance, the Home's Victorian-inspired Architecture and Inviting Wraparound Porch set a Gracious Tone. Inside Gleaming Hardwood Floors Introduce a Warm and Welcoming Interior Featuring a Spacious Living Room with an Archway to the Beautiful Formal Dining Room that Seamlessly Blends into the Newly Renovated Open-Concept Kitchen with Quartz Countertops, a Striking Marble Backsplash, Pantry and Stainless Steel Appliances. The Counter Seating Enjoys an Open View into the Expansive Sun-filled Great Room and Adjacent is a Delightful Three-Season Room Offering the Perfect Place to Relax or Read. A New Powder Room and Additional Access to the Beautifully Landscaped Private Yard with a Stone Wall and Steps to Vibrant Seasonal Flowers, Lush Perennial Bushes and Specimen Plantings plus a Charming Stone Pathway Further Enhance the Peaceful Backyard Sanctuary. The Second Level Features a Spacious and Light Filled Primary Suite with WIC and Vaulted Ceiling Overlooking the Backyard Oasis Along with Three Additional Bedrooms and a Full Bath. A Generous Sized Three Room Attic with Vaulted Ceiling, Enhanced by Abundant Natural Light and Lovely Views, Provides Wonderful Additional Space and Versatility. This Special Home is Ideally Located just a Short Distance from Oyster Bay's Vibrant Downtown Where you can enjoy Charming Shops, Cafes, and Acclaimed Restaurants that Give this Historic Hamlet it's Distinctive Character. Nearby, Theodore Roosevelt Memorial Park offers a Sandy Beach, Marina, Ballfields, Tennis, Pickleball Courts and Most of all Breathtaking Sunsets. The Oyster Bay LIRR Station is Conveniently Located Nearby. 43 Kellogg Street Offers an Inviting Combination of Character, Modern Updates, Beautiful Outdoor Space, and an Exceptional Oyster Bay Lifestyle.

43 Kellogg Street, Oyster Bay
$4,288,888
7 Beds ⋅ 8 Baths ⋅ 1019177 MLS
Welcome to 314 Mill Hill Rd Mill Neck located in the Luxurious Gold Coast. This Exquisite home has been built by William Townsend the historic mansion was widely known as the Chancellor's Mansion, which was built in 1834. The estate has passed through several notable historical figures, including Theodore Roosevelt III and fashion designer Oleg Cassini. This estate sits on almost 6 Acres . The property has additional 2 Large guest homes . Which can make a wonderful compound for friends, staff or guests. Each guest house is about 2300 SF and nicely updated . The main Estate consists of 7 Bedrooms 8 bathrooms, Stunning Chefs Kitchen, And A Grand Formal Dining Room, This home a true masterpiece of workmanship. The gorgeous wrap around porch adds so much character and comfort ,The beautiful large balcony on the 2nd floor is ideal for relaxing and enjoying the Stunning Water views of Oyster bay Harbor. The property has a custom built greenhouse which is ideal for growing your own farm to table fruits and vegetables. This home is in close proximity to the local private Beach which is only 2 blocks away. The history of this home has been written up in multiple books and periodicals. A true gem not to be missed AN VERY LOW TAXES !

314 Mill Hill Road, Mill Neck
$2,874,000
4 Beds ⋅ 3 Baths ⋅ 955339 MLS
Nestled in the Prestigious hamlet of Oyster Bay Cove in part of the exclusive Laurel Cove private association. This magnificent custom French Chateau enchants the moment you arrive. A grand estate entrance framed by lush privacy gardens sets the tone for a true storybook experience. Inside a breathtaking wedding style staircase makes a dramatic first impression. The elegant library wing features coffered ceilings, custom built-in book shelving, and a charming marble faux-tiled fireplace that creates a warm and refined retreat. The primary suite is a sanctuary of luxury, boasting 14-foot ceilings and floor-to-ceiling French doors that open seamlessly to the pool and gardens. A boutique-style formal dressing room-complete with a sliding ladder to maximize storage-leads to a spa-inspired bath. The soaking tub, perfectly positioned beside French doors opening to the gardens, offers a serene indoor-outdoor experience. Designed for grand entertaining, the formal living room parlor features soaring 14-foot ceilings, six French doors opening to the pool and front porch terrace, a stately Rumford fireplace-evoking the elegance of a private ballroom. The formal dining room is equally refined, with coffered ceilings and custom built-in cabinetry for fine China and serving pieces. The farmhouse-style kitchen is both inviting and dramatic, centered around a second Rumford fireplace and flowing through French doors into a spectacular wall-of-glass conservatory-greenhouse. Rich hardwood floors run throughout the main level enhancing the warmth and sophistication. Two graceful staircases lead to separate bedroom wings, offering both privacy and architectural distinction. The second floor east Wing has 2 bedrooms sharing a Jack and Jill Bathroom. The west wing is set to be a 5th bedroom currently being used as a office-storage space, Heat and AC access is avaialble, oversized laundry/ storage room. The The tranquil park-like grounds are an entertainer's dream, accessible through 17 French doors. The property features a gunite in-ground-pool, custom paver patio, fountain, firepit, and lush, professionally landscaped gardens. Every modern luxury is included: Central air conditioning, generator, in-ground sprinkler system, 300-amp electrical service, central vacuum, wine cellar, part-finished basement, workshop and a 2 1/2 car garage. Enjoy private beach access, enjoy swimming, boating , playground, with breathtaking views of Cold Spring Harbor, along with deeded-mooring rights, racks for kayaks. Ideally located near " Sagamore Hill "summer home of Theodore Roosevelt. fine dining, shopping, and the Long Island Railroad, this extraordinary estate offers a rare opportunity to live a truly enchanted lifestyle. A storybook life awaits on the North Shore's most desirable coastal communities.

38 Tiffany Road, Oyster Bay Cove

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.