Browse All Old Westbury NY Historical Properties for Sale

5 Beds ⋅ 5 Baths ⋅ 1020445 MLS

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 spacious living rooms, each with a fireplace, provide flexible living and gathering spaces. The gourmet kitchen showcases ceramic tile flooring, an oversized island, custom cabinetry, and an open-concept design ideal for everyday living and entertaining. Outdoor amenities include a private in-ground pool, bar area, and two balconies, creating a resort-style setting for relaxation and entertaining. Additional features include four ensuite bedrooms, a two-car garage, and ample storage. Located in the Jericho School District, close to shopping, dining, golf, major highways, and with convenient access to New York City. Total taxes reflect Village of Old Westbury annual taxes of 10,846.36

32 Valley Road, Old Westbury

$3,175,000

5 Beds ⋅ 9 Baths ⋅ 978369 MLS

Situated on two flat acres of beautifully landscaped grounds along one of Old Westbury's most sought-after and prestigious streets, 9 Applegreen Drive is a striking contemporary estate offering exceptional privacy, scale, and luxury amenities. Surrounded by lush, mature plantings, the property provides a serene, park-like setting rarely found in such a prime location. A dramatic spiral staircase creates an unforgettable first impression upon entering the residence, setting the tone for the home's distinctive contemporary architectural character. Designed for both comfortable living and grand-scale entertaining, the home features 5 spacious bedrooms and 9 bathrooms (7 full and 2 half), with every bedroom enjoying its own private en-suite full bathroom. The luxurious primary suite serves as a private retreat, highlighted by a spa-inspired bathroom complete with an in-home sauna. A conveniently located first-floor laundry room enhances everyday functionality and ease of living. The chef's kitchen is equipped with premium Sub-Zero, Wolf, Bosch, and Miele appliances, along with a newly installed trash compactor, offering exceptional functionality and refined design. Complementing the main kitchen is a fully equipped butler's pantry functioning as a secondary kitchen, complete with its own refrigerator, stove, and microwave, ideal for entertaining, catering, and everyday convenience. The residence has been meticulously maintained and enhanced with numerous recent improvements, including new basement flooring, a new boiler, a new water heater, and updated deck, all installed within the past year. Outdoor living is equally impressive. A wraparound deck spans the rear of the home, providing the perfect setting for relaxing or entertaining while overlooking the expansive grounds. The estate also features a Har-Tru tennis court and a gunite swimming pool with newly installed pumps, creating a true resort-style experience. Adding tremendous versatility and value is the fully equipped pool house, thoughtfully designed for year-round enjoyment with its own dedicated heating and cooling systems. The pool house features a full kitchen complete with refrigerator, stove, and microwave, a comfortable living area, a full bathroom, dedicated washer and dryer, and charming herringbone brick flooring that creates a warm, rustic ambiance throughout the space. Whether used for entertaining, hosting guests, or relaxing poolside, the pool house offers a complete private retreat. Additional highlights include an attached two-car garage, a recently installed cesspool, freshly resealed driveway, brand-new sprinkler pump and heads, robust 400-amp electrical service, and an additional 150-amp service dedicated to the pool house and cabana amenities. Combining striking contemporary architecture, extensive capital improvements, resort-style amenities, and an exceptional location in the heart of Old Westbury, 9 Applegreen Drive presents a rare opportunity to own a meticulously maintained estate in one of Long Island's most coveted luxury enclaves.

9 Applegreen Drive, Old Westbury

$2,499,000

4 Beds ⋅ 5 Baths ⋅ 1016084 MLS

Fully renovated 2025 luxury Ranch on 2.3 private acres in prestigious Old Westbury. This 4-bedroom, 4.5-bath home features soaring cathedral ceilings, spacious rooms with two fireplaces, renovated gourmet eat-in kitchen, and a fabulous two-room primary suite with walk-in closets. Resort-style backyard features a large gunite pool, deck, and tennis court — ideal for entertaining. Conveniently near upscale shopping (Roosevelt Field & Broadway Mall), fine restaurants, and public transportation (LIRR & NICE Bus). Top-rated East Williston School District (Wheatley School). A rare gem with privacy and modern upgrades — must be seen!

249 Glen Cove Road, Old Westbury

$2,999,000

5 Beds ⋅ 5 Baths ⋅ 993215 MLS

JERICHO SCHOOLS * OLD WESTBURY * LUXURIOUS GILDED-AGE GOLD COAST ESTATE --set on several beautifully landscaped acres on a private cul-de-sac along prestigious Clock Tower Lane. Positioned at one of the highest elevations on Long Island, this exceptional property offers privacy, scale, and timeless elegance. The grand interior features soaring ceilings, exquisite millwork, expansive formal rooms, and 8 original woodburning fireplaces. A state-of-the-art Rutt kitchen with premium Viking ovens anchors the home. Everything has been upgraded for today's elegance and style. Resort-style grounds include a sparkling pool with pool house, beautiful patio, and private tennis court, surrounded by lush perennial gardens. Additional amenities include central air, full-house generator, Tesla charger, security system, 2-car garage, and handicap accessibility. Located in the award-winning Jericho School District. A rare opportunity to own a truly iconic Gold Coast estate.

42 Clocktower Lane, Old Westbury

$1,600,000

5 Beds ⋅ 4 Baths ⋅ 961318 MLS

4 August Lane is an extraordinary, once-in-a-lifetime Signature Estate this opportunity to acquire a custom-built 1970 estate set on 2.2 acres of private, gated grounds in the prestigious village of Old Westbury — one of Long Island’s most affluent and historically significant communities. Privately owned by the same family for nearly 50 years, this is a rare generational offering. Gated entry with tree-lined drive and 2nd access directly to the LIE service road. 5,000 taxable sq ft plus full basement leading to 6-car garage and 2 car garage off the 1st floor. Six bedrooms, incl. maid’s quarters. Second floor features oversized primary suite w/ ensuite bath + 3 additional bedrooms and full hall bath. First floor includes foyer, formal dining room, formal den, guest bedroom, kitchen, laundry, and garage access. Dramatic 25’ x 40’ great room w/ 20’ ceilings, fireplace, full bath, loft area, and large sliders. Property was formerly two lots now combined into one 2.2-acre parcel. The grounds are truly amazing and reason enough to purchase this is a opportunity for a Home requires full renovation and is being sold as-is. Limited financing options. Convenient to parkways, LIRR, and approx. 22 miles to Manhattan.

4 August Lane, Old Westbury

$3,295,000

7 Beds ⋅ 8 Baths ⋅ 916110 MLS

OLD WESTBURY. ICONIC COLONIAL-REVIVAL MANOR - Set on 2.26 private acres, this 1932 William Lawrence Bottomley–designed Colonial-Revival estate is distinguished by its remarkable architectural form. A four-story brick center residence is flanked by two sweeping first-floor wings that extend in a graceful semi-circle, creating both symmetry and a sense of grandeur rarely seen. Inside, timeless details include a dramatic spiral floating staircase, arched windows, intricate moldings, multiple fireplaces, and light-filled entertaining spaces. The home features 7 bedrooms, 5 full and 3 half baths, including a regal primary suite with study, dual baths, and walk-in closets. Elegant gathering rooms include a banquet-sized dining room, a solarium with wet bar and billiards area, and a stunning octagonal library with imported, fluted, conical ceiling and incredible acoustics. The grounds are equally impressive, offering a heated gunite pool with brick surround, outdoor kitchen, and a pool house with party room, kitchenette, and baths, a circular courtyard with 5 garage bays, and slate and copper roofing complete this one-of-a-kind estate. A must see!!

88 Wheatley Road, Old Westbury

$2,499,000

5 Beds ⋅ 3 Baths ⋅ L3591033 MLS

HUGE PRICE REDUCTION Stunning Ranch in Jericho School District on 2.1 Acres This beautiful property offers the perfect blend of space, comfort, and luxury living. Featuring a spacious 5-bedroom, 2-bathroom home with a large, inviting living room and a cozy family room complete with a fireplace. Enjoy year-round relaxation with both an indoor and outdoor pool, or take advantage of the private tennis court for outdoor recreation. The property also includes a charming barn, ideal for additional storage or hobbies. Located in Jericho School District, this is the perfect place to call home., Additional information: Separate Hotwater Heater:Yes

20 Rolling Hill Road, Old Westbury

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