Browse All Old Westbury NY Historical Properties for Sale

Welcome to this beautiful estate, where you will be immersed in luxury and convenience. This shy 5,000 sq-ft home is an entertainer's delight, smart technology and multiple settings to impress. The bespoke "Bar Room" with a lighted alabaster bar, vaulted stamped copper ceiling and dual fireplace is a unique entertaining spot. This ‘Lifestyle’ home features radiant heat, an expansive kitchen with 2 breakfast areas, and a unique 'Show Kitchen' that opens to the dining room. The great room features high coffered ceilings with custom lighting, a large fireplace and walls of glass doors to the patios. The Primary suite boasts 2 Primary baths and 2 large walk-in closets, as well as 2 private balconies and an impressively grand fireplace. The finished Basement provides maid's quarters with outside entrance, a huge gym plus a full bath with a large steam shower. This spectacular residence is situated on 1.17 acres and boasts an all-new driveway, patios, wall, landscaping, new heated salt-water pool, new separate hot tub, 2-car garage, and renovated 1,152 sq-ft Pool/Guest house. With 5 fireplaces, 2 outdoor kitchens, a huge covered dining area with pizza oven and outdoor movie screen, this property is the perfect setting for cherished memories to come! Wheatley Schools, Village of Old Westbury

213 Guinea Woods Road, Old Westbury

$1,899,900

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

$2,550,000

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

$2,599,000

4 Beds ⋅ 3 Baths ⋅ 993811 MLS

Welcome to 55 Rolling Hill Road in Old Westbury, a truly distinctive ranch-style 4-bedroom, 2.5-bath residence tucked away on a quiet dead-end cul-de-sac backing the prestigious Glen Oaks Country Club. Inspired by Japanese-influenced landscape design and natural elements, this home offers a rare blend of architectural character, serenity, and timeless craftsmanship. Set among mature trees, curated plantings, and Japanese-inspired gardens, the property creates a peaceful sense of arrival from the moment you enter. From an aerial view, the home reveals its full estate-like presence, beautifully framed by layered landscaping, vibrant specimen plantings, winding garden beds, and lush green surroundings. Inside, natural woodwork, stone accents, expansive windows, and warm organic textures define the home’s character. The dramatic family room features soaring wood ceilings, built-in shelving, a fireplace, and walls of windows that frame picturesque greenery, creating a space that feels both grand and grounded. The main level offers an ideal layout with an entrance foyer, formal dining room, open eat-in kitchen with island, first-floor bedroom, full bath, and inviting living spaces designed for both everyday comfort and entertaining — all enhanced by the ease and convenience of ranch-style living. The kitchen blends function and style with generous prep space, open shelving, and views of the surrounding landscape. The home also features a spacious laundry room, full walk-out basement, and four-car garage with driveway parking. Outdoors, the in-ground gunite pool is tucked into the garden setting, creating a private retreat surrounded by natural beauty, color, and calm. A beautifully designed stone patio provides the perfect setting for outdoor dining, lounging, and entertaining amid tranquil landscaped grounds. Stone pathways, specimen trees, mature shrubs, and layered plantings continue the home’s seamless connection to nature and design. Located within the highly regarded Jericho School District, including Cantiague Elementary, Jericho Middle School, and Jericho Senior High School, this exceptional Old Westbury home offers privacy, beauty, scale, and a story unlike any other.

55 Rolling Hill Lane, 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

$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

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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.

Old Westbury Historical Real Estate

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