Browse All Upper Brookville NY Properties for Sale

Nestled at the end of a long private driveway on a Hampton shingle-style estate spanning 3.5 acres in Upper Brookville, this masterpiece includes five bedrooms, six full baths, and two half baths, all surrounded by mature specimen plantings, enchanting flowering gardens, and a captivating recirculating pond with a tranquil waterfall. As you approach, a pathway flanked by picturesque koi ponds and lush flora welcomes you to the residence. Beyond the glass French doors, the foyer bathes in natural light beneath soaring vaulted ceilings, seamlessly connecting to the inviting living room with a majestic stone fireplace and an elegant dining room, offering sweeping vistas of the sprawling yard and the inviting bluestone patio. The renovated, designer chef's kitchen showcases Zebrawood custom cabinetry paired with pristine white Caesarstone countertops, a substantial center island for gathering, and an array of top-of-the-line appliances, including a six-burner gas Thermador cooktop and oven, Sub-Zero refrigerator and freezer. Radiant heat extends to an informal dining area and a sun-drenched vaulted sunroom with patio access, affording delightful views of the meticulously curated gardens. This home's thoughtful design encompasses two distinct wings; one includes a refined library/home office with a cozy fireplace and built-in cabinetry, a powder room, a capacious family room, and two bedrooms, each graced with its own ensuite bath. Ascend the wing's private staircase to discover the primary suite, featuring a sitting room with French doors opening to a balcony overlooking the pond and backyard. Within the primary suite, indulge in the opulence of two sumptuous marble ensuite baths and two dressing rooms adorned with custom closets and cabinetry. The opposite upstairs wing reveals another private staircase leading to an inviting guest quarters replete with two additional bedrooms and ensuite baths, a charming sitting room, ample storage, and a dedicated exercise room. Ascending further, a bonus room on the third level beckons. Completing this magnificent estate is a spacious three-car garage and a generator for added convenience and peace of mind.

41 Wheatley Road, Upper Brookville

$2,599,000

5 Beds ⋅ 4 Baths ⋅ 3454307 MLS

A Tuscan-style farm ranch with extra living quarters for extended stays is a stunning and spacious residence that embodies the charm and elegance of the Tuscan countryside. This magnificent home has been fully updated with modern amenities and features, making it the perfect blend of old-world charm and contemporary luxury. The property boasts a stunning pool and spa area, where you can relax and soak up the sun on warm days. For those cozy evenings, a beautiful movie theater is available to watch your favorite movies. In addition to the main house, this property also includes a 1 bedroom cottage, perfect for accommodating guests. The cottage is fully equipped with all the necessary amenities, ensuring a comfortable stay. The centerpiece of the home is the big eat-in kitchen, which features granite counters, beautiful hardwood floors, and a wood-burning pizza oven. The kitchen is the perfect place to prepare meals for family and friends, and the wood-burning pizza oven adds a unique touch of authenticity to the cooking experience. The banquet-sized dining room has a wood-burning fireplace and is perfect for large gatherings. This beautiful home is a perfect retreat for those looking for a luxurious and comfortable home. The beautiful surroundings and modern amenities make it a truly unique and special property. Must See to Appreciate .

1 Pine Valley Road, Upper Brookville

$3,988,000

5 Beds ⋅ 6 Baths ⋅ 3500393 MLS

LOCATION! Young 5 BR Brick Colonial (7725 Sq ft) On Picturesque PRIVATE 5+ Acres! Tranquil Setting with IG Pool W/ flowing Hot tub, BBQ, & Entertainment Area.Majestically Located On A Private Cul-De- Sac. ABSOLUTELY STUNNING!

3 Fairway Court, Upper Brookville

$2,475,000

4 Beds ⋅ 5 Baths ⋅ 3496567 MLS

Set on 3.16 Acres, This 4 Bedroom Residence has been totally renovated for Today's Lifestyle. This sprawling light-filled single-level residence has an Open Floor plan for easy living and entertaining. A Large Living Room, Den, Sun Room and Dining Room are sophisticated and stylish. Walls of sliding glass doors and oversized bay windows provide sunlight-filled rooms with lovely views and access to expansive patios and gardens. Gleaming Oak Floors , new gourmet kitchen, luxurious bathrooms adds to the cohesive warmth and design. The tranquil primary suite has an oversized bow window and sliders that open onto and a deck. Two additional bedrooms are comfortably scaled and a fourth bedroom is a suite with separate sitting room. The outdoor swimming pool complex with living room and bedroom offer additional entertaining space. Must See.

1281 Wolver Hollow Road, Upper Brookville

$2,950,000

6 Beds ⋅ 5 Baths ⋅ 3495498 MLS

1167 Pine Valley Road is a luxurious home in Upper Brookville, Long Island, with a captivating California vibe. Inspired by Frank Lloyd Wright's architectural style, this residence rests on nearly four acres of stunningly landscaped gardens, including front and rear ponds and a mesmerizing waterfall by the primary bedroom. Enjoy country club living with amenities offering privacy, luxury, and convenience within reach of New York City, this property embodies the perfect blend of California charm on Long Island.

1167 Pine Valley Road, Upper Brookville

$7,450,000

6 Beds ⋅ 9 Baths ⋅ 3489197 MLS

A 11,200 Sq.Ft. Mansion, Constructed in 2013, located on 1.99 pristine acres in Upper Brookville, NY. Interior details include 10ft Ceilings, a spacious Chef's Kitchen with Viking Appliances, Herringbone Wood Floors throughout, a solid Stucco and Wrought-Iron facade and 3 marble fireplaces. At 6 Bedrooms and 7.55 Bathrooms total, this home features a whole-house generator, a theater, 2-story wine cellar, wet-bar, fitness area and game-room. The beautiful property boasts a large gunite in-ground pool and jacuzzi, an outdoor kitchen, commercial-grade playground, a vegetable garden with irrigation and a detached Cabana with a full-kitchen. Located within the Oyster Bay-East Norwich Central School District.

353 Juniper Drive, Upper Brookville

$5,995,000

6 Beds ⋅ 9 Baths ⋅ 3488297 MLS

Welcome to this exquisite ultra luxury home located in the prestigious Upper Brookville neighborhood of Long Island. Situated on a tranquil 2.2-acre plot, this custom-built brick colonial with imported stone accents on the facade presents an unparalleled level of craftsmanship and opulence. Meticulous attention to detail is evident throughout the property, from the stunning soffit molding and copper gutters to the use of the highest quality exterior materials available. Approaching the home, you'll be captivated by the professionally landscaped grounds, showcasing mature foliage carefully selected to enhance the property's beauty. As you step through the heavy steel front door, perfectly befitting this grand residence, you'll be greeted by a double-height entry foyer. The sweeping staircase and magnificent chandelier set the tone for the elegance and sophistication that awaits. No expense has been spared in the interior design of this home. Custom crown molding, coffered ceilings, and exquisite wainscot millwork adorn every room. The windows are adorned with handcrafted, custom window treatments made from the finest materials, adding a touch of luxury to every living space. The living room features a stunning mantle and a grand piano, creating an ideal space for entertaining guests. The sunroom boasts floor-to-ceiling windows and elegant French doors that open up to the expansive back patio. Its abundance of natural light and lighter color scheme create a unique ambiance, while a double-sided fireplace connects it to the neighboring family room. The family room exudes warmth and traditional charm, with its rich mahogany and cream-colored coffered Venetian plaster ceilings. The kitchen is a chef's dream, featuring high-end appliances, a generous center island, double sink, and double oven. Adjacent to the kitchen, a butler's pantry with an additional sink leads into the spacious dining room, perfect for hosting lavish dinner parties. The home office, crafted entirely in mahogany, offers a regal space for work or relaxation. French doors lead out to a private patio, providing a serene retreat. On the main level, you'll discover a guest bedroom suite complete with a full bathroom, ensuring comfort and privacy for visitors. The temperature-controlled three-car garage, equipped with a car lift, is a car enthusiast's dream, offering ample space for working on vehicles and motorcycles. Ascending to the second floor, the grand master suite awaits, encompassing multiple rooms. This expansive sanctuary features a sitting room, separate "his" and "her" walk-in closets, an oversized master bathroom with a standalone tub, an exercise room, and a balcony overlooking the sprawling yard. Additionally, four bedrooms with en suite bathrooms and walk-in closets provide luxurious accommodations for family members or guests. The convenience of a second-floor laundry room adds to the home's functionality. The basement is an entertainment haven, boasting a custom-made theater, game room, recreation room with a wet bar, gym area, full bathroom, and a wine cellar, providing endless opportunities for leisure and relaxation. Outside, the backyard oasis beckons with a stunning bluestone patio featuring a fully equipped outdoor kitchen, pizza oven, and a cozy fire pit. Adjacent to the heated gunite pool, complete with a sun deck, jacuzzi, waterfalls, and seating, a gazebo lounge awaits, offering two televisions, a wood fire pit, and ample space for relaxation and enjoyment. Ascending the stairs towards the pool house, you'll discover a second fully equipped outdoor kitchen, while the raised patio area boasts another gas fire pit. The pool house exudes a rustic charm reminiscent of Vail, Colorado, with exposed beams, a kitchenette, a lounge area, and a full bathroom. Completing the outdoor amenities is a professional bocce ball court, providing a perfect setting for friendly competition and leisure activities. This home truly has it all, reflecting the owner's unwavering commitment to luxury and attention to detail. Nestled within the highly sought-after Locust Valley school district and in close proximity to the exclusive shopping and entertainment of the Gold Coast, this property presents a once-in-a-lifetime opportunity to experience the epitome of luxurious living.

1 Victor Court, Upper Brookville

$7,800,000

7 Beds ⋅ 9 Baths ⋅ 3485647 MLS

UPPER BROOKVILLE. An incredible renovation, and new story to tell, within this Architectural Gem in Upper Brookville. A modernized spin, exquisitely crafted and designed with the finest of materials and craftmanship to provide luxury and casual elegance, on the Old World Charm estate, sitting privately and serenely on over 5 acres of formal gardens, with several patios, inground pool, pool house, porte cochere, and more. Incredible floor plan that encompasses a unique and open feeling, with spectacular staircases on either sides of the home. Featured in the May 2000 Issue of "Architectural Digest."

N Chestnut Hill Drive, Upper Brookville

$7,800,000

7 Beds ⋅ 9 Baths ⋅ 3485634 MLS

Chateau de L' Amour is a stunning interpretation of the original creativity of renowned architects,Ike Kligerman Barkley, known for enhancing Life through Design. With a talented eye for design, the owners of this magnificent property succeeded in completely transforming this exquisite Gold Coast Estate and created a Masterpiece that defines Living a Life of Luxury. Spanning over 10,000 sqft with 7 bedrooms & 7.55 Baths, the Interior boasts a balance of modern & traditional design elements with a harmonious blend of artisan woods, soft palettes & bespoke materials. The privacy & relaxed seclusion of this property creates entertaining ease with an indoor/outdoor flow for social engagement, whether grand scale or more intimate gatherings. Additional Interior features include Lower Level Playroom,MediaRm,Salon,MassageRm,WineRm & Gym. This Magnificent Gem is set on 5 acres with Landscape Lighting,Gated Courtyard Entrance, Porte Cochere passage to Service Courtyard & Heated Four-Car Garage,Enchanting Vistas,Formal Gardens,Multiple Patios,Expansive Pool Patio, IG Salt Water Pool/Jacuzzi,Fire Pit, & Fully Renovated Pool House with expansive Kitchen/Entertainment Rm/2 Full Baths/ Private Changing Room

A Chestnut Hill Drive, Upper Brookville

$1,495,000

5 Beds ⋅ 5 Baths ⋅ 3487483 MLS

Unlimited Opportunities to Renovate or Build a Brand-New Home. 1185 Pine Valley Road is a Prime, 2+ Acre property beautifully landscaped, located in the heart of Upper Brookville, NY. Situated down a Private, cul-de-sac road, this 5 Bedroom Expansive Ranch has a scenic long driveway, an open layout, an in-ground heated pool and a 4+ car attached garage. Located within the esteemed Locust Valley Central School District.

1185 Pine Valley Road, Upper Brookville

$2,475,000

8 Beds ⋅ 5 Baths ⋅ 3471317 MLS

7,800sf Contemporary!

70 Wolver Hollow Road, Upper Brookville

$6,995,000

10 Beds ⋅ 10 Baths ⋅ 3477761 MLS

Introducing GRAY HORSE FARM: This magnificent iconic estate on desirable Piping Rock Road is situated on 9 flat acres and offers 13,324 square feet of luxe living plus beautiful apartments, exquisite pool and pool house, stable, paddocks, barn, tennis and sports court. The impressive scale of the home is enhanced by vintage millwork, antique hand-painted wallpaper, and priceless Samuel Yellin front gates from the JP Morgan estate. Built in 1924 and designed by architect James W. O'Connor and landscape architect Robert Ludlow Fowler, this classic brick Georgian Colonial resonates with old-world charm and grace. Original architectural details combine beautifully with a modern lifestyle for exceptional entertaining. With amazing property and amenities, make this home your own spectacular residence! Part of Locust Valley School District, convenient to private schools, fine dining, Americana shopping, 27 miles to Manhattan. Equestrian's delight! keep your favorite horses near you!

60 Piping Rock Road, Upper Brookville

$3,900,000

7 Beds ⋅ 10 Baths ⋅ 3445976 MLS

7 BR, 10 BA, 10,000 Sq. ft. Colonial in Upper Brookville

66 Wolver Hollow Road, Upper Brookville

$1,199,000

3474501 MLS

INCREDIBLE, SECLUDED LOCATION! (Currently a 4 BR Colonial.) *A TEAR DOWN* AS IS. FABULOUS PRIVATE COUNTRY RD!!

1029 Friendly Road, Upper Brookville

$3,688,000

5 Beds ⋅ 5 Baths ⋅ 3470774 MLS

This exceptional estate is located just 30 miles east of Manhattan in the Incorporated Village of Upper Brookville. Introduced by handsome herringbone patterned brick piers with lights at the foot of the drive, the residence's forecourt welcomes guests to the impressive five-bedroom residence. Perfectly situated on 2.68 level acres, there is room for both a swimming pool and tennis court. Newly constructed, the residence's architecture is inspired by timeless Colonial design. Architectural details play across the white cedar-clad facade. Features dentil molding and a chic board and batten surround, the entry portico is refined and inviting. The grand double height foyer opens to a light-filled and spacious floor plan with beautifully proportioned rooms trimmed with layered moldings and paneled wainscoting. A curved staircase climbs to the second level. Gleaming oak flooring adds warmth, and ten-foot high ceilings give volume to the interior spaces. Columns introduce the formal living room which is anchored by a tall fireplace with an attractive red brick herringbone patterned firebox. The dining room is set for gracious gatherings. The spacious great room has a fireplace that adds to the warm ambiance of the room. It seamlessly flows into the well-appointed kitchen that is furnished with crisp white custom cabinetry, quartz backsplashes and countertops, an island with seating for four, and a suite of top-of-the-line JennAir stainless appliances for the chef. French doors open to a Cambridge paver stone patio that expands the living and entertaining spaces to the outdoors. There is a wet bar with wine refrigeration and a butler's pantry. A second entrance opens into a well-equipped mudroom with storage. There is a second staircase that travels to the second and lower levels, a laundry room, a powder room and access to a two-bay attached garage. At the opposite end of the residence, a quiet library/study with French doors to the backyard is perfect for work from home. There is a comfortable main level bedroom overlooking the front courtyard and a full bath.The second level opens to a serene primary suite. It features a generous dressing closet with custom fittings and a luxurious en suite bath that boasts a double rainfall steam shower with exquisite polished mosaic patterned marble. There is a deep Hydro System soaking tub, and luxurious radiant heat offers comfortable warm flooring. In addition, there are three additional restful bedrooms and two full baths that complete this level. Third floor offers a full walk up attic. The lower level is an open multi-function space with high ceilings and access to the outdoor. It can be styled for recreation, home theatre and/or wellness. This new construction five-bedroom residence is fitted with luxurious and stylish finishes and a floor plan for gracious living and entertaining in a beautiful Upper Brookville, New York setting. The area is rich in history and offers the acclaimed 416-acre Planting Fields Arboretum, New York State Historic Park and fine shopping and dining nearby.

80 Mill River Road, Upper Brookville

$5,875,000

7 Beds ⋅ 9 Baths ⋅ 3468763 MLS

NEW CONSTRUCTION, TO BE BUILT by one of North Shore's premium builders and to be completed 2nd QTR 2024. The time to customize is now! Architectural plans available for review. Make this luxury residence your dream home, with 7 bedrooms, in-ground heated salt-water pool and outdoor cabana on 2 beautiful acres in Upper Brookville.

3 Donna Drive, Upper Brookville

$1,000,000

3 Beds ⋅ 1 Baths ⋅ 3463318 MLS

Property For Sale In The Heart Of Brookville. Offering a Great Opportunity To Build On Land And Invest In Dream Home. Beautiful and Quiet Neighborhood. Peaceful Living in a More Rural Landscape.

8 Remsens Ln, Upper Brookville

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