Browse All Glen Head NY Historical Properties for Sale

Nestled on two private acres, this stunning 4-bedroom, 3.5-bath ranch combines timeless comfort with resort-style living, featuring over 3,100 square feet, an in-ground pool, and beautifully designed indoor-outdoor spaces, all within the acclaimed North Shore School District.

153 Brookville Lane, Glen Head

$999,999

3 Beds ⋅ 2 Baths ⋅ 1025046 MLS

Beautifully remodeled home offering a bright, open layout with soaring vaulted ceilings, gleaming hardwood floors, and timeless finishes throughout. The inviting living room is anchored by a stunning fireplace, creating the perfect space to relax or entertain. The updated interior seamlessly blends style and comfort, while large windows fill the home with natural light. Step outside to a private patio, ideal for outdoor dining, entertaining, or simply enjoying the peaceful surroundings. Located in the highly desirable North Shore School District, this move-in-ready home is a wonderful opportunity to enjoy modern living in the heart of Glen Head.

56 Glen Cove Drive, Glen Head

$1,188,000

4 Beds ⋅ 2 Baths ⋅ 1024196 MLS

Located in the highly coveted, award-winning North Shore School District.Welcome home to this move-in-ready, newly renovated Colonial perfectly situated at the beginning of a charming, quiet cul-de-sac. This 4-bedroom, 2-full-bath home beautifully balances classic warmth with modern upgrades and an open space concept. The expanded 2,300 sq. ft. layout (1,561 sq. ft. livable) begins on the first floor with an inviting living room, a beautifully updated open-concept kitchen/dining room, a full bathroom, and an attached garage. Upstairs, find 4 spacious, sun-drenched bedrooms and a second full bath. Full finished basement provides incredible additional space for a home gym, media room, or play area. Enjoy seamless everyday living with unbeatable convenience—just minutes to the LIRR for an easy commute, plus nearby supermarkets, fine dining, and premier shopping. All information is deemed reliable but not guaranteed. Don't miss this Blue-ribbon North Shore gem!

7 Locust Street, Glen Head

$975,000

4 Beds ⋅ 2 Baths ⋅ 1022186 MLS

Welcome to 22 Locust Avenue, a legal two-family residence ideally located in the heart of Glen Head. This property offers two spacious apartments, each featuring two bedrooms, one full bath, hardwood floors, comfortable living areas, updated kitchens and baths, and separate entrances for added privacy and convenience. Additional highlights include a fenced backyard, detached two-car garage, and conveniently located to local shops, dining, parks, and the Long Island Rail Road. With its flexible layout, desirable location, and income producing potential, this property presents an excellent opportunity for investors or owner occupants.

22 Locust Avenue, Glen Head

$727,100

3 Beds ⋅ 2 Baths ⋅ 1016764 MLS

AUCTION/OCCUPIED. 3- bedroom, 2 bath 1,499 square feet home sitting on 6,200 square foot lot in Glenwood Landing. Home is a short distance from Glen Head LIRR station, 3 different golf courses and Sea Cliff Beach. Property is sold “as is” with NO property disclosures, NO inspection reports, NO interior photos, NO lease in place, NO access- The seller does not represent or guarantee occupancy status. NO VIEWINGS of this property. Please DO NOT DISTURB the occupant. Buyer is responsible for obtaining possession of the property upon closing.

31 Glenwood Road, Glen Head

$999,000

3 Beds ⋅ 3 Baths ⋅ 1007334 MLS

Lovingly updated, this warm and inviting home in the Promenade section of prime Glen Head offers a versatile multi-level layout with 3 bedrooms and 2.5 bathrooms, including a spacious primary ensuite. Featuring multiple living and entertaining spaces across different levels, including a lower-level den/playroom and a generous backyard with multi-level decking. This home blends comfort and functionality with ease. Centrally located, near the Glen Head train station, local shops and restaurants at the four corners, and within the sought-after North Shore School District.

7 Cedar Lane, Glen Head

$1,050,000

4 Beds ⋅ 2 Baths ⋅ 1006246 MLS

Welcome to this beautifully updated 4-bedroom, 2-full-bath Cape Cod located in the heart of Glen Head, one of Long Island’s most sought after North Shore communities. Situated within the acclaimed North Shore School District, this charming home offers the perfect blend of comfort, convenience, and location. The main level features a spacious first floor primary bedroom, a full bath, and inviting living spaces designed for everyday living and entertaining. Enjoy the luxury of radiant heated floors in the kitchen, dining room, and family room, while gas heat serves the remainder of the home. Central air conditioning provides year-round comfort. Upstairs, you’ll find three additional bedrooms and a second full bath, offering flexibility for family, guests, home offices, or hobbies. The partially finished full basement provides valuable bonus space for recreation, storage, a gym, or playroom. Step outside to a beautifully landscaped, fully fenced backyard featuring a patio ideal for outdoor dining, entertaining, or simply enjoying a quiet evening at home. A one-car garage and mature landscaping further enhance this property’s appeal. Beyond the home itself, enjoy all that Glen Head and the North Shore lifestyle have to offer. Conveniently located near parks, local shops, restaurants, and the Glen Head LIRR station, commuting to New York City and surrounding areas is effortless. Appreciate the area’s tree-lined streets, proximity to the Long Island Sound, recreational opportunities, traditional village, and strong sense of community that make the North Shore such a desirable place to call home. Move right in and enjoy the perfect combination of updated living, outdoor enjoyment, and an exceptional North Shore location

10 Radcliff Boulevard, Glen Head

$1,699,000

5 Beds ⋅ 6 Baths ⋅ 992632 MLS

Set in the heart of Glen Head, this exceptional expanded farm ranch at 30 Todd Drive is full of surprises — a home that truly goes on and on, offering far more space than you would ever imagine from the moment you arrive. Rebuilt and substantially enlarged in 2002, this meticulously maintained residence features 5 bedrooms with potential for a 6th bedroom, 4 full bathrooms, and 2 powder rooms across an expansive and thoughtfully designed layout, including an additional 1,535 square feet of finished lower-level space with egress access to the backyard. A welcoming foyer introduces beautifully scaled interiors highlighted by oversized rooms, rich hardwood flooring, and custom architectural details throughout. The spectacular eat-in kitchen serves as the heart of the home, featuring a large center island with seating, granite countertops, stainless steel appliances, extensive cabinetry, and generous dining space with sliding glass doors opening to the backyard. The formal dining room is perfectly positioned with oversized windows overlooking the private grounds, filling the space with natural light. The impressive family room showcases soaring vaulted ceilings and a dramatic stone wood-burning fireplace, creating a warm and inviting atmosphere with an additional set of sliding doors leading outdoors. The main-level primary suite offers a peaceful retreat complete with a spa-inspired bath and oversized walk-in closet. A second first-floor ensuite bedroom provides ideal accommodations for guests, extended family, or multigenerational living. Upstairs, an additional ensuite bedroom is complemented by two spacious bedrooms, a shared full bath, and a bonus den. The finished lower level provides exceptional additional living space with approximately 1,535 square feet, including laundry, abundant storage, and an expanded area with direct egress access to the rear property. Outside, the secluded backyard is surrounded by mature landscaping and designed for effortless outdoor enjoyment, featuring a patio, gas cooking hookup, basketball area, and exceptional privacy. An oversized two-car garage completes this outstanding offering. A rare North Shore opportunity combining expansive living space, thoughtful design, and timeless appeal, all conveniently located near shopping, dining, public transportation, and within the acclaimed North Shore School District.

30 Todd Drive E, Glen Head

$925,000

4 Beds ⋅ 2 Baths ⋅ 1002600 MLS

Nestled in the highly desirable Glen Knolls neighborhood of Glen Head, this beautifully maintained 4-bedroom, 1.5-bath Cape Cod blends timeless charm with everyday comfort. Rich in character, the home showcases original mill work, stained glass, and a stunning wood-burning fireplace that creates a warm, inviting ambiance. Featuring gleaming hardwood floors and an open floor plan, this home offers many updates, gas heating and cooking, ductless air conditioning, a full unfinished basement with laundry, and an attached one-car garage with electric vehicle charging station. Step through glass doors to a spacious deck overlooking private lush property, where vibrant perennial gardens create a serene outdoor oasis surrounding the blue stone patio, perfect for relaxing or entertaining. Conveniently located with bus to Glenwood Landing Elementary and proximity to North Shore Middle and High Schools. Enjoy all the benefits of living in the Town of Oyster Bay, including access to TOBAY beaches, parks, and recreation and new Gold Coast Library. Low taxes: $12,444.26!

5 Salem Way, Glen Head

$1,688,000

5 Beds ⋅ 4 Baths ⋅ 989458 MLS

Room for everyone in this expanded and updated Glen Head center hall colonial offering 5 bedrooms and inviting living spaces. The impressive entrance highlights the custom stairs and millwork. An open floor plan is convenient for today's lifestyle. The spacious living room features a fireplace and opens to the gracious formal dining room with double doors leading to the private rear patio complete with outdoor kitchen. An expansive kitchen offers Wolf gas cooking, double ovens and lots of counter space making cooking and entertaining a breeze. The second floor highlights the sun drenched primary bedroom with soaring 11 ft ceilings and french doors to bath featuring radiant heated floors. The additional 4 bedrooms are all spacious with generous storage spaces. Two additional full baths are located on the second floor. A lower level introduces ample recreation areas, laundry room and full bath. This home does not disappoint. Conveniently located within steps to the North Shore Middle/High Schools, close to LIRR, shopping, dining and Tappen Beach.

1 Kissam Lane, Glen Head

$710,000

6 Beds ⋅ 3 Baths ⋅ 994281 MLS

Public online Auction: Bidding opens 5/26/26 @ 1 pm & Ends 5/28/26 1 pm (approx). The price of property exclusively represents the suggested opening bid & not the price of the property. Sold "as-is". Great opportunity for a buyer who does their homework & is looking to purchase a 2 family fixer-upper in Glen Head. Please read all information-your due diligence is necessary. Registration deadline 5/27/26 4 pm

2 Huron Street, Glen Head

$975,000

3 Beds ⋅ 2 Baths ⋅ 990103 MLS

Welcome to this charming Ranch in Glen Knolls, offering 3 bedrooms and 2 beautifully renovated bathrooms. Sunlight pours through skylights, filling the home with an easy, uplifting feel, while multiple fireplaces bring comfort and charm through every season. A cozy den creates the perfect spot to unwind, gather, or simply enjoy a quiet moment. Set on a nicely sized property, the home extends effortlessly outdoors with a large deck, spacious yard, and sprinkler system—ideal for relaxing, entertaining, or play. Ideally located near the LIRR and within the North Shore School District, this home offers everyday convenience with a special bonus for train lovers: the gentle, passing sound of the train can be enjoyed right from your backyard, adding a uniquely nostalgic touch to this special setting.

53 Plymouth Drive S, Glen Head

$1,265,000

3 Beds ⋅ 2 Baths ⋅ 988963 MLS

Welcome to this beautifully renovated Colonial nestled in the highly desirable Hill Terrace area, offering the perfect blend of classic charm and modern updates. A welcoming entry foyer sets the tone, leading into a sun-filled living room featuring a cozy fireplace—ideal for relaxing or entertaining. The formal dining room provides a space for gatherings, while the updated eat-in kitchen boasts granite countertops, stainless steel appliances, and sliders that open to the deck overlooking the yard. This home offers three well-appointed bedrooms and two full baths, including a convenient full bath on the main level. The full, unfinished basement provides excellent potential and includes a laundry area, ample storage, and walk-out access through the garage. Step outside to a wonderful, private yard complete with a deck, patio and shed—perfect for outdoor entertaining, gardening, or simply enjoying your own peaceful retreat. Located within the North Shore School District. Just minutes from Tappen Beach, shopping and dining. Move in ready for you to make this home your own.

61 Cleveland Avenue, Glen Head

$2,699,000

5 Beds ⋅ 4 Baths ⋅ 989507 MLS

Welcome to this exceptional home located in Brookville Village, within Jericho School District. Perfectly situated in a peaceful and quiet neighborhood, this property offers both comfort and convenience. Close to schools, making daily routines effortless; Easy access to major highways for a smooth commute; Minutes from shopping, dining, and everyday essentials; New attic insulation for improved energy efficiency; Brand new roof for long-term peace of mind; Newly installed 22 kW whole-house generator; Chimney recently repointed with new lining; Recently redone gunite pool – perfect for relaxation and entertaining; Spacious outdoor area ideal for gatherings and activities; This home combines modern upgrades with a tranquil setting, offering a rare opportunity to own this move-in ready gem!

14 Ormond Park Road, Glen Head

$1,099,999

5 Beds ⋅ 2 Baths ⋅ 988576 MLS

Welcome home to this charming expanded cape nestled on a quiet street in desirable Glenwood Landing. This 5-bedroom, 2-bath residence is just a short distance from local schools and golf course. The main level features an inviting open-concept layout, highlighted by a warm and welcoming living room with a cozy wood-burning fireplace. The dining area is ideal for entertaining, while the kitchen boasts a peninsula with seating—perfect for casual meals or gathering with guests. A versatile bonus room with sliding glass doors opens to the backyard, creating seamless indoor-outdoor living. Two bedrooms and a full bath with double sinks and a walk-in shower complete this level. Upstairs, you’ll find three additional bedrooms and another full bath. One standout bedroom features vaulted ceilings and sliding glass doors leading to a private deck—an ideal spot to unwind and enjoy sunset views. The full basement offers a separate entrance, generous storage space, and a washer and dryer. Step outside to a beautiful backyard featuring both a deck and patio—perfect for entertaining or relaxing—along with a detached two-car garage. Don’t miss this opportunity to own a beautiful home in a highly sought-after location.

11 Edgewood Avenue, Glen Head

$898,000

3 Beds ⋅ 2 Baths ⋅ 986756 MLS

Welcome to this charming split-level home offering a perfect blend of comfort, functionality, and outdoor beauty. Featuring 3 bedrooms and 1.5 baths, this well-maintained residence provides a versatile layout ideal for everyday living and entertaining. Step outside to a true gardener’s paradise—lush, thoughtfully landscaped grounds filled with vibrant plantings, mature greenery, and peaceful garden spaces. A charming patio provides the perfect setting for outdoor dining, morning coffee, or simply enjoying the serene surroundings. This home is a wonderful opportunity for those seeking both indoor comfort and exceptional outdoor living.

1106 Glen Cove Avenue, Glen Head

$1,375,000

4 Beds ⋅ 2 Baths ⋅ 981017 MLS

As spring arrives, an exceptional opportunity awaits to own this beautifully updated original Stern Family home, thoughtfully reimagined and extensively renovated in 2024, ideally situated in Glen Head’s sought-after Hill Terrace and overlooking the prestigious Engineers Country Club golf course. This high-end center hall Colonial seamlessly blends classic Tudor-inspired design with modern luxury and offers a true turn-key lifestyle where every detail has been thoughtfully addressed. Newly refinished hardwood floors run throughout, complemented by a freshly painted interior, all new Pella windows, updated bathrooms featuring new toilets throughout, and a slate roof that has been professionally cleaned and well maintained. The fully renovated eat-in kitchen is a true showpiece, featuring a quartzite waterfall island, Wolf 6-burner gas range with pasta water spout, Sub-Zero refrigerator, beverage refrigerator, and radiant heated floors. The kitchen flows effortlessly into the dining area with direct access to the backyard. The living room offers a wood-burning fireplace and connects to a heated sunroom with access to the yard, providing additional living space. The second level features a sun-filled primary bedroom along with three additional bedrooms. The fully finished walk-out lower level adds approximately 650 square feet of living space and includes a recreation area and a new, modern laundry room. Step outside to your private outdoor oasis, complete with an in-ground saltwater pool with a new liner, heated spa with waterfall feature, and an outdoor kitchen equipped with a BBQ, sink, and refrigerator. The property is enhanced with mature plantings, in-ground sprinklers, and outdoor lighting. Additional features include a two-car detached garage, oversized driveway, and an electric vehicle charging station conveniently located by the garage. Conveniently located near shopping, dining, transportation, and major roadways, and located within the sought-after North Shore School District. Don’t miss this exceptional opportunity.

60 Roosevelt Avenue, Glen Head

$1,895,000

5 Beds ⋅ 5 Baths ⋅ 975020 MLS

A Rare 2-Acre North Shore Estate-Like Setting Offering Privacy, Presence, and Endless Potential Set on approximately 2 acres of private, park-like grounds, this timeless Colonial with vintage charm presents a truly rare opportunity in the heart of Glen Head. Privately set back and gently elevated from the road along a long, tree-lined approach, the property offers an exceptional sense of space and seclusion—an increasingly rare offering on the North Shore. Overlooking the surrounding area, the home enjoys beautiful natural light and the opportunity to take in stunning sunset views from its elevated setting. Inside, the home features a classic and functional layout with expansive living areas, a formal dining room, and a bright breakfast nook designed for both everyday living and effortless entertaining. A charming original butler’s pantry adds character and functionality, while central air provides year-round comfort. A standout feature is the detached 3-car garage with electric, offering exceptional flexibility for vehicles, storage, or a workshop. The true highlight remains the land—flat, usable, and rich with possibility—offering the perfect canvas to create a custom outdoor retreat, expand, or simply enjoy the tranquility of your own private setting. Recent updates include a roof and gutters less than one year old, a burner approximately 6 years old, and a hot water heater approximately 3 years old, adding additional value and peace of mind. Ideally located just moments from shopping, dining, and transportation, this property delivers the rare balance of privacy, scale, and convenience.

195 Cedar Swamp Road, Glen Head

$899,000

3 Beds ⋅ 2 Baths ⋅ 971961 MLS

Welcome to this charming home located in the heart of Glen Head! This well-maintained property features 3 spacious bedrooms and 2 full bathrooms. The bright eat-in kitchen offers beautiful granite countertops and a skylight ceiling that fills the space with natural light. An additional versatile 10'2"x20' room provides the perfect opportunity for a potential 4th bedroom, home office, or guest space. Step outside to enjoy the well-maintained 24x12 covered Trex deck, ideal for entertaining or relaxing. The home also includes a Generac Generator for added convenience and peace of mind. A wonderful opportunity to own a comfortable and inviting home in a prime location close to shops, dining, and transportation.

29 Glen Cove Drive, Glen Head

$825,000

3 Beds ⋅ 2 Baths ⋅ 957740 MLS

Opportunity knocks! This charming three-bedroom, one-and-a-half-bath ranch is in desirable Glen Head with North Shore Schools. Convenient to the train, highways, and shops. A blank canvas ready to make your own, with endless possibilities and easy expansion potential!

856 Glen Cove Avenue, Glen Head

$2,480,000

5 Beds ⋅ 4 Baths ⋅ 937836 MLS

Exquisite 5-bedroom residence on a private cul-de-sac set within the highly-regarded Jericho School District. This home features approximately 3,959 sq ft of living space on a flat, pristine 2-acre parcel. Built in 1952 and lovingly maintained, the property offers timeless appeal with modern comforts — two fireplaces, central air-conditioning, and a fully finished lower level. Outdoors, enjoy a resort-style in-ground gunite pool, adjacent pool-house and bocce court, all tucked away among lush landscaping for ideal entertaining or tranquil everyday living. A rare opportunity to reside in one of the North Shore’s most exclusive enclaves — schedule your private tour today.

4 Norgate Road, Glen Head

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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.

Glen Head Historical Real Estate

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