Browse All Glen Head NY Historical Properties for Sale

THE "ULTIMATE" GLEN HEAD OPPORTUNITY — HARBOR VIEW, IN-GROUND POOL & TREMENDOUS POTENTIAL — OFFERED AT JUST $799,000 Located in the desirable Harbor View section of Glen Head, within the Hamlet of Oyster Bay, this expanded Cape offers an exceptional opportunity for buyers looking to renovate, customize, and create a home that reflects their own vision. Situated on an approximately 7,035-square-foot lot, the property offers a compelling combination of location, outdoor living, privacy, and future potential. The interior is ready for updating and renovation, providing the perfect canvas for a buyer to re imagine the space and make it their own. The backyard is a true highlight and is designed for entertaining, featuring a fenced-in backyard featuring an in-ground swimming pool with a Salt water conversion system , expansive patio areas, an enclosed/covered porch overlooking the pool, and a separate gazebo ideal for outdoor dining, entertainment, relaxing, and enjoying the warmer months. Conveniently located near the LIRR, shopping, restaurants, and everyday amenities, and situated within the highly regarded North Shore School District. North Shore Senior High School was recently ranked No. 2 among Nassau County’s Top 10 High Schools in the ranking provided. With its sought-after Harbor View location, generous lot size, impressive outdoor amenities, and substantial renovation potential, this property presents an exciting opportunity to create something truly special in Glen Head. Pool -Property -Potential & Location Offered at just $799,000. Come see the possibilities this Harbor View home has to offer. The home is being sold as-is and offers an excellent opportunity for updating, expansion, customization. The kitchen ,Baths and interior finishes are dated and ready for renovation,while the property offers tremendous potential to create a home that suits your style and needs. Whether you’re an end user, investor, or contractor, this is a unique opportunity to unlock the full potential of the home and property. BRING YOUR VISION and make 2 Ruth Place your own.

2 RUTH Place, Glen Head

$789,000

5 Beds ⋅ 2 Baths ⋅ 1040374 MLS

This double dormered Cape Cod features a living room, formal dining room, a kitchen, a den, two bedrooms and a full bath on the main floor and three bedrooms including the primary bedroom ( full with primary bedroom is huge and could easily be divided into two separate bedrooms ) and a bath on the second floor. There is a full basement, a one car garage that is not in good shape, an in-ground pool that needs to be repaired or replaced, hardwood floors, tile floors, a newer main roof, all gas cooking and Heating and a very quiet location that is walk to most things. This house needs a lot of work but is a diamond in the rough.

1 Glen Cove Drive, Glen Head

$929,000

4 Beds ⋅ 2 Baths ⋅ 1039687 MLS

A Builder’s Dream in Hill Terrace! Bring your vision and your contractor—this well-located home offers an exciting opportunity for buyers looking to renovate, customize, and create their dream home. Nestled in the desirable Hill Terrace neighborhood of Glen Head, this property is surrounded by beautiful homes and offers incredible potential. Enjoy a top-rated school district and a prime location close to everything—charming village shops and dining, beautiful beaches, schools, and the railroad for an easy commute. Whether you're looking to build, renovate, or invest in a sought-after community, this is an opportunity not to be missed. Builders and savvy buyers—come now! The possibilities are endless.

35 Washington Avenue, Glen Head

$1,099,998

3 Beds ⋅ 2 Baths ⋅ 1038251 MLS

Welcome to this charming three-bedroom, two-bathroom home in the heart of Glen Head, offering comfortable living spaces, thoughtful updates, and wonderful outdoor amenities. The formal living room features a beautiful fireplace, creating a warm and inviting setting for relaxing or entertaining, while the adjacent dining room provides an ideal space for family meals and gatherings. The updated kitchen offers modern convenience and functionality, and the spacious family room provides plenty of room for everyday living, movie nights, or entertaining guests. The primary bedroom is a private retreat with its own balcony, while two additional bedrooms provide comfortable spaces for children, guests, or a home office. With ample storage throughout and a full unfinished basement, there is plenty of space for organization, hobbies, recreation, or future expansion. Outside, enjoy a fully fenced backyard designed for both relaxation and entertaining. A covered patio provides a comfortable outdoor living area, while a separate fire pit area creates the perfect spot for gathering with family and friends. Ideally located in Glen Head, this home offers convenient access to the Long Island Rail Road, Tappan beach, nearby parks and recreational areas, and the highly sought-after North Shore community and school district. A wonderful opportunity to enjoy the space, charm, and convenience of Glen Head living.

40 Plymouth Drive S, Glen Head

$1,299,000

4 Beds ⋅ 4 Baths ⋅ 1035793 MLS

Welcome to this DIAMOND, beautifully renovated Colonial offering approx. 2400 sq ft of stylish living space in the sought after North Shore Acres neighborhood. With exceptional curb appeal and extensive renovations completed in 2023, this move in ready home perfectly blends modern updates with timeless charm. The spacious interior features four generously sized bedrooms and three and half baths, including a primary suite with a stunning en-suite marble bathroom with radiant heated floors. Designed for both everyday living and entertaining, the home offers a bright living room with an additional sitting area, dining room,versatile playroom or home office, updated eat in kitchen with stainless steel appliances, spacious attic, and a large outdoor storage shed. Included in the renovation is a new roof, siding, windows, boiler, & A/C. Situated on over 1/3 of an acre, the property offers a beautiful patio for outdoor entertaing and a large, flat, beautiful piece of property. Easy access to NYC, Covenient to all, North Shore Schools. Must See!

53 Beechwood Drive, Glen Head

$888,000

3 Beds ⋅ 1 Baths ⋅ 1027250 MLS

Charming Corner Property "The Promenade" – Glen Head Tucked into one of Glen Head's most walkable and welcoming pockets, this Charming 3-bedroom, 1-bath ranch sits proudly on a coveted corner lot along The Promenade — offering both character and convenience in equal measure. Step inside and be greeted by warm, original wood floors that flow throughout the home, adding timeless charm to every room. The cozy fireplace serves as a natural gathering point, perfect for quiet evenings in or entertaining friends and family on a crisp fall night. Sun-filled rooms and a comfortable layout make this home as practical as it is inviting. Outdoor living is just as special here. Start your mornings on the classic front porch with a cup of coffee, or unwind in the evening on the spacious back deck — both finished with durable, low-maintenance Trex decking designed to look beautiful for years to come. Whether you're hosting a summer barbecue or simply enjoying some fresh air, these outdoor spaces extend your living area beautifully. Practicality meets opportunity with the attached 1-car garage, offering easy parking and extra storage, while the unfinished basement is a blank canvas — ideal for a home gym, workshop, media room, or simply valuable extra storage space. Perhaps best of all is the unbeatable location. Situated within the highly regarded North Shore School District, this home is just moments from the elementary school, making morning drop-offs a breeze. Commuters will love the close proximity to the train station, while everyday errands are simplified with a grocery store and local shops just around the corner, and the Long Island Sound down the road. Here, small-town charm meets everyday convenience — a rare combination that's hard to find. This is more than just a house — it's a place to put down roots, build memories, and enjoy the very best of Glen Head living. 3 Bedrooms | 1 Bathroom | 1-Car Garage | Unfinished Basement | North Shore Schools Schedule your private showing today — homes like this in The Promenade don't come along often!

38 Hill Drive, Glen Head

$1,199,000

4 Beds ⋅ 3 Baths ⋅ 1030036 MLS

Pride of ownership is evident in this charming 4 bedroom Colonial that beautifully blends timeless character with thoughtful updates. Lovingly expanded and meticulously maintained by its current owners, this warm and inviting home is ready for its next chapter. Inside you'll find comfortable living spaces filled with charm and character, making this a home that has been cherished over the years Nestled in the highly coveted Harbor View Community, and set on a private, level property, the outdoor space is ideal for entertaining and everyday enjoyment, featuring a spacious patio, buit-in BBQ area, grass yard, storage shed and access to the garage. . Opportunities to own a home in this sought-after neighborhood are few and far between. This property is a true gem and will not last long!

10 Polly Lane, Glen Head

$2,775,000

4 Beds ⋅ 4 Baths ⋅ 1025463 MLS

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

$1,088,000

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

$935,000

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. Upstairs apartment has 2 bedrooms, 1 bath and large loft. 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

$649,000

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

$1,688,000

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

$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

$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

$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

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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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