Upper Brookville NY Real Estate, Homes, Condos for Sale

Upper Brookville - "Casa Blanca" This stunning residence offers an unparalleled blend of sophisticated elegance, modern amenities, and exceptional craftsmanship. With 4/5 spacious bedrooms and 4 meticulously designed bathrooms, this home provides the perfect sanctuary for both relaxation and entertainment. As you approach the property, you are greeted by a beautifully landscaped front yard, featuring lush greenery and elegant stone pathways that lead you to the grand entrance. Step inside to a breathtaking foyer, showcasing high ceilings, a sweeping wrought iron staircase, and an abundance of natural light that floods through expansive windows. Off the entry foyer you have a beautiful space which can be used as a first floor bedroom ensuite or a private office. The main level features numerous intricate moldings and detailed wainscoting throughout. The formal dining room offers and large space suited for large scale formal dinner parties. The open concept living spaces are thoughtfully designed to offer seamless flow and connectivity, perfect for modern living. The living room, adorned with exquisite light fixtures, custom moldings & gas fireplace, transitions into the kitchen creating a grand open entertaining space. Sliding glass doors off the living room/kitchen open to a paved patio creating a beautiful indoor/outdoor living concept. The heart of the home is the state-of-the-art kitchen, a culinary enthusiast's dream. This gourmet kitchen boasts top-of-the-line stainless steel appliances, custom cabinetry, large center island with stunning granite countertops, wetbar as well as a large pantry. The second level features a one of a kind second floor living space with double glass doors which open to a gorgeous balcony overlooking the property. The four upstairs bedrooms are generously proportioned, each offering serene views and ample closet space. The primary suite is a true retreat, featuring a spa-like en-suite bathroom with a soaking tub, a glass-enclosed steam shower, and double vanities. The additional bathrooms are equally luxurious, with high-end fixtures, designer tiles, and elegant finishes. The finished basement is perfect for entertaining and includes a beautiful glass enclosed wine storage space. The backyard oasis features an in-ground pool, cabana as well as multiple patio spaces. Luxury living at its finest. A Masterpiece Listing.

9 Locust Lane, Upper Brookville

$1,745,000

3581058 MLS

Build your dream home on this secluded 2.22 acre level lot! This property features a very special location at the end of of a private country lane which is serene & quiet yet close to roadways, schools, shopping and clubs.

No # Linden Lane, Upper Brookville

$1,749,000

4 Beds ⋅ 4 Baths ⋅ 3580392 MLS ⋅ Village Upper Brookville BLDG.

Discover Luxury Living on the Gold Coast in this pristine, recently renovated Farm Colonial, nestled on just over 2 Acres at the end of a long, private driveway on prestigious Wolver Hollow Road. This Sun-filled gem exudes charm and luxury, boasting opulent moldings with granite accents, along with hardwood floors throughout. The eat-in-kitchen features sleek cabinetry with built-ins and stunning marble countertops, perfect for both culinary adventures and casual family gatherings. The expansive family room, with its vaulted and large windows, offers impeccable views of the vast property and includes a large wood-burning fireplace as the centerpiece of this open-concept floor plan. On the first level, you'll also find a formal living room, dining room, half bath, and entertainment room-perfect for hosting guests. The full basement provides additional living space, laundry, and ample storage. Upstairs, the primary bedroom is a sanctuary with built-ins, a sizable marble bathroom, and a walk-in closet. Another large bedroom includes an ensuite bathroom, and generous-sized additional bedrooms offer comfort, with one featuring a staircase leading to a unique loft or attic area. Generator, Propane, French Drain, Granite Walkway plus 27-Zone Inground Sprinkler system, and more. With taxes, including village, at just $20,000, this marvel won't last long. Don't miss your chance to experience luxury living in Upper Brookville.

100 Wolver Hollow Road, Upper Brookville

$38,500,000

13 Beds ⋅ 17 Baths ⋅ 3578383 MLS

Behold Applewood Estate, an expansive 35+ acre serene property nestled within the prestigious Village of Upper Brookville. This unmatched North Shore architectural masterpiece with 6+ dwellings, offers both grandeur and elegance. The unrivaled property was meticulously designed with professional landscaping, decorated with mature privacy hedges, formal gardens with water features and rolling green lawn space. Rooted in history, this magnificent estate was once an Apple Orchard Farm back in the early 1900's and was also formerly owned by the celebrated 19th-century American Artist Montague Flagg. The bespoke Main Residence encompasses an impressive 13,000 Sq.Ft. of living space, was custom built with Slate, Brick and Stone in 2005 and is a testament to high-end design and luxury living. Designer details include Onyx Marble installations, spacious primary rooms, oversized parquet wood floors, handmade iron fireplaces, thick-cut millwork and more. A grand Foyer with a winding staircase, a Great Room with intricate coffered 23 foot ceilings and a magnificent Library loft and a handcrafted Meditation Room, a Billiards/Game room with a Wet-Bar and a Eat-In-Kitchen with a Breakfast Room overlooking the peaceful backyard are just a few of the interior highlights that make this home truly special. Additionally, this unrivaled estate features several detached houses including a 2 Bedroom Colonial Residence and a meticulously reconstructed circa 1914 Stone Barn, now serving as a guest retreat. This distinguished horse-property includes a newly resurfaced tennis court, a separate sports court, a 6-door detached garage, a commercial-grade 150kW generator, a long tree-lined driveway and a secure gated entrance, ensuring peace, beauty and privacy. Equestrian enthusiasts will appreciate the formal horse stables complete with a training ring. The property further boasts a heated in-ground pool pavilion with a jetted jacuzzi spa and a built-in outdoor kitchen, as well as a 1 bedroom Pool House and numerous other refined amenities, making it a Gold Coast sanctuary of relaxation and sophistication.

Applewood Estate, Upper Brookville

$3,695,000

6 Beds ⋅ 5 Baths ⋅ 3577621 MLS

Situated in the prestigious Upper Brookville, this exquisite property offers a serene pond view with a charming fountain that enchants during the summer time. This stunning brick colonial home boasts six spacious bedrooms and four-and-a-half bathrooms. Completely renovated in 2019, this elegant residence combines classic charm with modern designs located in the highly sought-after North Shore School District, renowned as the top district in the area. This property offers an idyllic lifestyle in one of the most luxury and tranquility coveted neighborhoods.

23 Overbrook Lane, Upper Brookville

$2,650,000

6 Beds ⋅ 5 Baths ⋅ 3576064 MLS

Located on the picturesque Overbrook Lane in Upper Brookville, this exquisite full-brick estate is set on 1.24 acres of serene land with breathtaking views of a private pond. Spanning over 7,300 sq. ft., this luxurious masterpiece offers 6 spacious bedrooms and 4.5 elegantly appointed baths, all wrapped in a blend of modern sophistication and timeless craftsmanship. From the moment you enter, you're greeted by custom-designed Staircase, millwork and hand-painted ceilings that speak to the impeccable attention to detail throughout the home. The gourmet kitchen, complete with a large center island, seamlessly connects to the exquisite are and breakfast rooms, ideal for both entertaining and intimate gatherings. The opulent primary suite is a retreat unto itself, featuring a spa-like bath and three walk-in closets, while five additional bedrooms offer generous space and comfort. In addition a dedicated spa/sauna invites you to unwind in ultimate relaxation. The fully finished basement, with its soaring ceilings, provides endless possibilities for recreation and entertainment. Step outside to your private oasis: a beautifully landscaped backyard with a tranquil pond, offering a peaceful escape or the perfect setting for outdoor activities. Energy-efficient solar panels further enhance this estate, offering significant savings on electricity costs. The round driveway leads to a spacious 3-car garage, adding both convenience and grandeur to this must-see property.

21 Overbrook Lane, Upper Brookville

$2,650,000

6 Beds ⋅ 5 Baths ⋅ 3575359 MLS

Discover the perfect blend of luxury and tranquility in this extraordinary hilltop estate. Nestled on over 2.5 acres of beautifully secluded landscape, this stunning 6,500+ sqft Expanded Colonial home offers an inviting retreat with elegance and charm. Enter this gorgeous home and you will discover six generously sized bedrooms offering both comfort and privacy, along with five welcoming fireplaces, including a gas double-sided fireplace and a wood-burning double-sided fireplace, creating a warm and inviting atmosphere. The eat-in kitchen features gas cooking with two ovens. The extraordinary solarium, with its radiant heated floors, serves as a sunlit haven meant to be enjoyed in all four seasons. Each bathroom has been thoughtfully renovated with exquisite custom finishes. Step outside to a world of serene outdoor living, surrounded by lush greenery that invites relaxation and impressive entertaining space. This home is a true sanctuary, offering warmth, elegance, and the ultimate in refined living. The property also offers a convenient commute to NYC and located within the Locust Valley School District. A Must See!

999 Wolver Hollow Road, Upper Brookville

$3,699,000

5 Beds ⋅ 5 Baths ⋅ 3574927 MLS ⋅ Gated Estate BLDG.

Rare Opportunity on Private Gated Upper Brookville Lane. Only 11 Homes Built & Seldom Offered For Sale. Pride of Ownership throughout This Turn Key Brick Colonial on Quiet Interior 2A+ Site. Attention to Detail, Functional Floor Plan for Contemporary Living & Entertaining Indoors and Outdoors. Magnificent Landscaped Grounds Complete with Outdoor Kitchen, Oversized Patio, Gunite Pool with Waterfall, Gazebo, Koa Pond, Bocce Court & Generator. A Must See

5 Peacock Lane, Upper Brookville

$2,399,999

5 Beds ⋅ 5 Baths ⋅ 3568815 MLS

Welcome to Boulder Vista complete with a rocking chair front porch one-bedroom cottage. Looking for solace from a crazy world? A place where you and your loved ones can relax in peace and security far from worldly cares yet close to all you need and enjoy? Then this magnificent, gated, three-acre property in the heart of peaceful Upper Brookville, just thirty miles from Manhattan, is waiting to fulfill your dreams. Tucked away up a 560ft driveway with electronic gate and surrounded by several estates separated from you by lush woodland, this country-club-like property, with pool, spa, playground, guest house, pavilions, wooded pathways, and patios, plus a 4,000sf house, will take your breath away with its secluded, sprawling space and beauty. So serene and secluded, its 3.1 acres have been masterfully designed to provide all you could want for year-round enjoyment. Summer will delight you with expansive paving-stone patios and walkways, two dining pavilions, one with outdoor kitchen off the main house, and a second one on a huge patio surrounding the oversized, estate-fenced, freeform, inground pool. A scenic guest cabin with front porch, bath, bedroom, and outdoor shower and changing area, features a full eat-in kitchen with access to the poolside dining pavilion. A playground tucked in a shady corner of the property and a paved pathway wending through the woods provide additional areas to enjoy. In the winter, the property provides snowy vistas and a great area to practice your cross-country skiing before tackling the trails at nearby Muttontown Preserve. An outbuilding across the large parking area from the attached 4-car garage offers ample storage space. And a large hot tub accessed from the basement and rear patio is an inviting destination no matter the season. Ideal for entertaining year-round, the home's interior boasts huge interior spaces with a plethora of windows flooding the home with sunny views of the property and its visiting fowl and fauna. Renovated in 2005, it has been expanded over the years to provide room after room for many guests and activities. These include a welcoming living room with large bay window, a banquet-sized dining room off an updated kitchen that provides ample cherry cabinetry, granite countertops, ceramic tile backsplash, a huge sink, a bar sink, and high-end stainless-steel appliances including a Sub-Zero refrigerator with in-door ice and water, a built-in double oven, dishwasher, and a glass cooktop. Ceramic-tile floors flow into the immense four-season room (22'3" x 16'6") with serving bar extension of the kitchen, breakfast area, and access to the dining pavilion and outdoor kitchen. With glass walls and ceiling, this room offers spectacular views of the property. A few steps down from the living room, the entrance foyer, with access to one large walk-in closet, a powder room, guest bedroom, and laundry/mudroom opening to the four-car garage. The spacious and inviting den, a cozy getaway offers sliders (with retractable awning) opening to the dining patio plus a stone wall with raised hearth, fireplace, and built-in bookcases. Down a few stairs, the finished basement includes a large recreation room, with wall of closets, spacious storage area, utility room, and a guest suite with outside entrance accessing the rear patio and hot tub. Its bath has a tub/shower and dual access to bedroom and rec room. A few steps up from the living room, the upper level features a spacious primary suite with bath and large walk-in closet, two additional bedrooms and baths, and a hallway leading to a huge (22'1" x 39') bonus room with sixteen windows on three exposure, two double closets, carpeting, and room for anything you want from using as is (recreation room), or converting into more bedrooms and/or baths, etc. No matter your needs or desires, this exceptional offering can fill the bill. And its most important feature is its secluded setting. With about 200ft between your house and your neighbors' homes, plus a thick wall of pristine woodland and a long, gated driveway, you will be in a world of your own but still close to all Long Island's North Shore has to offer. Complete with a diesel generator in case of an emergency. Upper Brookville is a quiet residential enclave of about 1800 residents enjoying rolling wooded hills and gorgeous estates. It provides easy access to major highways, train stations, quaint village shops and restaurants and more. View 3D Tour and Floor Plan.

95 Wheatley Road, Upper Brookville

$5,980,000

7 Beds ⋅ 9 Baths ⋅ 3561364 MLS

Chateau de L' Amour is an immaculate 10,500 Sq.Ft. estate located within the heart of Upper Brookville, New York. Fully redesigned in 2023, this bespoke Gold Coast showpiece boasts unmatched interior customizations including thick-cut millwork, unique parquet floors, stained glass windows, round-top doors, coffered ceilings and hand-carved staircases. At 7 Bedrooms and 7.55 Bathrooms, this residence features multiple formal entertaining rooms, beautiful stone gas fireplaces, a finished walk-out basement and a sunlit eat-in-kitchen with marble countertops, Butler's Pantry, Viking and True Kitchen Appliances and a round, sunlit Breakfast nook. The spacious Primary Wing has tall ceilings, a sizable walk-in closet and a luxurious 'His & Hers' marble en-suite bathroom with a freestanding tub. An exceptional piece of North Shore architecture, the exterior of the home was masterfully constructed with brick, stone, slate and cedar shake. The 5+ acre property features a private electric gate, Porte Cochere, 4 Car Attached Garage, professionally landscaped gardens, a heated Salt Water Pool & Spa, a built-in firepit and a detached poolside cabana with a brand new center-island kitchen. Located close to esteemed Golf/Country Clubs, the vibrant village of Locust Valley and the LIRR.

35 Chestnut Hill Drive, Upper Brookville

$8,499,900

9 Beds ⋅ 13 Baths ⋅ 3559974 MLS

Located in a gated community in Upper Brookville, this 10,000-square-foot majestic Gold Coast estate welcomes you with a circular driveway, soaring ceilings, and a grand double staircase. This luxurious home boasts a balcony on the second floor, a raised panel mahogany ceiling, and built-in cabinets and bookcases. It contains a Chef's custom eat-in kitchen with double all Wolf appliances. This Estate features six fireplaces. All bedrooms enjoy en suite baths. The Main bedroom has four closets and an en suite bath with a fireplace, jacuzzi, and an enormous walk-in shower. The main house has seven elegant bedrooms, nine full baths, and two half baths. For the car lover, there is a three-car garage attached to the main house and a nine-car detached garage with heat and air conditioning. Over the detached garage, there is an elegant one-bedroom apartment. The basement contains a state-of-the-art media room, a 1200-bottle wine cellar, perfect for the collector or investor, a humidor for the cigar smoker, a game room, and a gym for those who enjoy staying fit at home. The full-house generator ensures uninterrupted power for this five-acre estate. For all those who appreciate nature, this home enjoys a garden that contains a variety of unique trees, vegetable gardens, and marvelous sprawling lawns. The Olympic pool is complemented by a pool house, a one-bedroom guest cottage, two outdoor kitchens, and a travertine patio for dining. Summer fun can be enjoyed by playing tennis and basketball, visiting nearby beaches, and enjoying North Shore luxury and amenities. The seller is willing to hold the mortgage to a qualified buyer.

9 Colonial Drive, Upper Brookville

$1,788,000

5 Beds ⋅ 4 Baths ⋅ 3559477 MLS

Welcome to this exceptional Upper Brookville Colonial, a timeless gem originally built in 1938 and thoughtfully extended and completely renovated in 2008. Despite the modern upgrades, the home retains its original charm, seamlessly blending classic elegance with contemporary comforts. Two Primary Suites: This home offers the luxury of two primary suites, one conveniently located on the main level and the other on the second floor, providing flexibility and comfort for multi-generational living or guest accommodations. The spacious Great room features soaring ceilings, creating an open and airy atmosphere. Large windows offer picturesque views of the lush, beautifully landscaped property, bringing the beauty of the outdoors inside. Throughout the home, you'll find meticulously renovated spaces that honor the original architecture while incorporating modern amenities and finishes. Hardwood floors, custom moldings, and high-end fixtures are just a few of the thoughtful details. Keeping up with modern needs, the home includes a car charging station, making it convenient for electric vehicle owners. The Chef's kitchen is equipped with state-of-the-art appliances, ample counter space, and custom cabinetry, perfect for preparing meals and entertaining guests. The outdoor entertainment area is an oasis designed for relaxation and fun. The in-ground saline vinyl pool offers a refreshing escape on hot summer days, surrounded by a beautifully landscaped patio. Extend your living space outdoors with an outdoor shower and a fully equipped outdoor kitchen, ideal for hosting summer barbecues and pool parties. The property is beautifully landscaped, providing a serene and private setting. Mature trees, flowering plants, and well-maintained lawns create a park-like atmosphere. This special home is a rare find, offering the perfect balance of historic charm and modern luxury.

729 Remsens Lane, Upper Brookville

$5,890,000

10 Beds ⋅ 10 Baths ⋅ 3554087 MLS

Welcome to GRAY HORSE FARM! This magnificent iconic equestrian estate on desirable Piping Rock Road is situated on 9 gorgeous acres and offers 13,324 square feet of gracious living with 10 bedrooms, 7.555 baths and 10 fireplaces, plus beautiful apartments, exquisite 20' x 55' pool and pool house with kitchen and full bath , stable, paddocks, run-in horse shed, tennis and sports courts. 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 and boasts a 17-year old slate roof. Original architectural details provide the perfect canvas for a modern lifestyle and exceptional entertaining. Renovations include the apartments, pool, pool house, tennis court, and HVAC system, ready for you to 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! 7-car garage, 600-AMP electrical service, whole house generator. Must see Special Features and video of antique wall covering- (click virtual tour link above to view). Taxes are being grieved.

60 Piping Rock Road, Upper Brookville

$3,348,000

7 Beds ⋅ 8 Baths ⋅ 3551746 MLS

Location, Location, Location! Equestrian Property. Magnificent Colonial set on 4.5 flat acres in the desirable Village of Upper Brookville. Horse Property! This stately Colonial has grand entertaining rooms, 7 bedrooms, 6.55 baths. Spacious Eat in Kitchen with Granite Counter tops. Mud room with cubbies. Elevator from garage up through 2nd floor perfect! Huge Primary Suite with (2) fireplaces,sitting room, balcony, walk in closet, bath with steam shower. 2 additional bedrooms on suite, 2 bedrooms with jack & jill bath, den. 2 additional bedrooms and 2 baths. Spectacular property with in-ground gunite pool, cabana, barn, stable and paddock. Professionally landscaped with things blooming all year. Convenient to 25A, Hwys, Schools, Shopping, LIRR, Town, Restaurants, Parks and Library.

963 Ripley Lane, Upper Brookville

$3,998,500

5 Beds ⋅ 5 Baths ⋅ 3534999 MLS

"Brookhaven" selected as a Masterpiece Collection Property is situated on 2.0 prime acres located on a quiet lane in the coveted Locust Valley area. This stately colonial feature 7,200 sq.ft. of sophisticated decor, impeccable craftsmanship, state-of-the-art infrastructure and security systems, convenient to schools, nature preserves, shops, dining, and waterfront creating an enviable country lifestyle. The luxurious main floor flows from the gracious double height entry hall with handsome millwork to the elegant living room with fireplace and formal dining room to the richly paneled library with fireplace then onto the spacious family room with fireplace. The sun-filled gourmet kitchen is equipped with top-of-the-line appliances and informal dining overlooking the sweeping lawn, glorious gardens, and shimmering new heated 20x50 gunite pool designed by Gibbons. The graceful spiral center stairway leads to the luxurious primary suite and boasting three spacious bedrooms/baths with a second staircase. The lower level where every detail has been considered for your enjoyment: Guest bedroom and bath; Theatre Room; Recreation Room; Storage. A magical setting to enjoy a true haven and to create memories! Enjoy the spectacular attached video.

12 Locust Lane, Upper Brookville

$2,450,000

4 Beds ⋅ 4 Baths ⋅ 3527038 MLS

Prime location in the Village of Upper Brookville on 2 flat acres. Locust Valley School District. The residence features a large guest wing bedroom all part of larger separate suite with den on the 1st floor plus the primary bedroom and two bedrooms on the 2nd floor. A gated entrance leads to a circular courtyard and ample parking in front. In-ground heated saltwater pool, waterfall, expansive stone patio, pool cabana and outdoor bar are phenomenal places to enjoy the scenic property. A fully equipped movie theatre, Poker Room and Wet Bar has a separate entrance. 2 car attached garage with electric vehicle charger. Natural gas heat has been piped in, rare for the area. Interior layout allows for a variety of ways in which to enjoy the spaces. The welcoming front porch enters into a two-story foyer and spacious den. A formal dining room is off the gourmet kitchen plus an adjacent stone lounge that flows to the outside. Hand built pizza oven. This property is located on a dead end street north of 25A. Nearby the Planting Fields Arboretum State Park and both the towns of Locust Valley and Oyster Bay. Enjoy North Shore living within proximity to numerous golf clubs and tennis clubs, nature preserves, bicycle trails, working farms and cultural destinations. This is a beautiful country setting not far from Manhattan and the perfect place to enjoy immediately.

1 Pine Valley Road, Upper Brookville

$5,875,000

7 Beds ⋅ 9 Baths ⋅ 3468763 MLS

NEW CONSTRUCTION, currently under construction by one of North Shore's premium builders and to be completed 4th QTR 2024. Now scheduling site tours. Make this luxury residence your dream home, with 6 bedrooms, in-ground heated salt-water pool and outdoor cabana on 2 beautiful acres in Upper Brookville.

3 Donna Drive, Upper Brookville

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