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$3,900,000
5 Beds ⋅ 5 Baths ⋅ 972146 MLS
Perfectly set on a winding country lane, this charming colonial combines timeless craftsmanship with modern luxury on over two level, landscaped acres designed by Steven Dubner. The home showcases fine millwork and mouldings with hardwood flooring throughout the first floor. A welcoming entry leads to a gracious living room with a gas fireplace, dentil moulding surround, and built -in bookcases leading into a formal dining room. French doors open to a new bluestone terrace with flower beds, a full outdoor kitchen, views of the saltwater, and gunite pool with an electric cover and expansive grounds. The gourmet kitchen features black marble countertops, imported tile backsplash, a quartz center island with a prep sink and top -tier appliances, including a Wolf cooktop, double wall ovens, Subzero refrigerator/freezer, Miele dishwasher, Sharp microwave and wine refrigerator. A breakfast room with banquette flows into the spectacular great room with cathedral ceilings, exposed beams, a brick wood-burning fireplace, built-in bar, Palladium window and terrace access. An office, laundry/mudroom and guest room with en suite bath complete the first floor. Upstairs, the Primary suite offers a sunlit sitting room/office, spacious bedroom, a luxurious marble bath with radiant heat, dual sinks, vanity, and two fully fitted dressing rooms. Additional accomodations include an en suite bedroom, two additional bedrooms with a shared new bath, a second washer/dryer and ample storage. A finished basement provides a playroom, storage, and easy access to the mechanicals. This is an exceptional home blending the charm of classic Long Island living with every modern convenience.

51 Linden Lane, Upper Brookville
$3,550,000
5 Beds ⋅ 5 Baths ⋅ L3574927 MLS
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, Additional information: Appearance:Pristine,Interior Features:Guest Quarters,Marble Bath,Separate Hotwater Heater:Yes

5 Peacock Lane, Upper Brookville
$3,300,000
6 Beds ⋅ 5 Baths ⋅ 872615 MLS
La Isabella : A Gracious 2 Acre Estate In Prestigious Upper Brookville Offering Timeless Colonial Architecture With Modern Luxury. Set Behind A Sweeping Drive And Surrounded By Mature Magnolia, Dogwood, And Maple Trees, This Home Is Crafted For Multigenerational Living With Privacy And Sophistication. Inside, A Dramatic Double-Height Foyer And Sweeping Staircase Welcome You To Spacious Sunlit Rooms Perfect For Entertaining And Everyday Life. The Formal Living And Dining Rooms Provide Elegant Settings, While The Expansive Kitchen Features Stainless Steel Appliances, A Large Island With Seating, Walk-In Pantry, And Eat-In Area Opening To A Stone Patio. The Family Room Includes A Gas Fireplace, Custom Built-Ins, And Wet Bar With Wine Cooler. Main-Level In-Law Suite With Full Bath Offers Flexibility And Privacy. Upstairs, The Luxurious Primary Suite Has A Private Terrace, Electric Fireplace, And Space For A Spa Bath. A Second En Suite Bedroom, Third Bedroom, And Bonus Room Complete The Upper Level. Outdoors, Unwind By A Stunning Pool Accented With A Natural Stone Waterfall, Expansive Lawns, And A Three-Season Room. The Lower Level Offers Storage And Potential For A Gym Or Media Room. Near Top Golf, Schools, And New York City.

13 Locust Lane, Upper Brookville
$3,200,000
6 Beds ⋅ 5 Baths ⋅ 1014387 MLS
Welcome to luxury living in Upper Brookville's most desirable location. This stunning furnished residence features 6 bedrooms, 5 bathrooms, an office, and a luxurious master suite with a steam shower, jacuzzi tub and a huge walk-in closet. Spread across beautifully landscaped grounds, enjoy amenities such as a Har-Tru tennis court, a heated Olympic-size pool with a spa, and a sun filled deck with an outdoor kitchen ideal for entertaining. The home boasts an integrated Sonos speaker system both indoors and outdoors, providing high-quality sound throughout. For fitness enthusiasts, there's an in-house gym, playground. The fenced property ensures privacy and security with gated access. Experience unparalleled comfort and elegance in this prestigious estate.

110 Linden Lane, Upper Brookville
$3,000,000
4 Beds ⋅ 5 Baths ⋅ 949252 MLS
Set on a deep two-acre parcel, this bespoke, reimagined property is enhanced by new landscaping and mature trees, offering a private and tranquil setting. New life has been breathed into this 1920s residence, creating an intimate and inviting milieu reminiscent of a European country villa. Enveloped in quiet elegance, the natural beauty of the fine materials and architectural details take center stage throughout. Renovated down to the studs, the home features all new plumbing, electric, air conditioning and septic system. Radiant heat throughout the first floor and all upper level bathrooms. Primary suite includes radiant heat in both bedroom and bath. Carlisle solid white oak tongue-and-groove random-width wide-plank flooring and custom woodwork are found throughout. Duravit bath fixtures, honed travertine marble, and all new windows and doors complete the interiors. The stunning living room and dining room offer high ceilings and French doors, with the dining area opening directly to a bluestone patio featuring a fire pit and seating area, ideal for additional outdoor entertaining. An open floor plan for the kitchen and family room features Christopher Peacock cabinetry, Carrera marble countertops, and Wolf appliances. Bedrooms include walk-in closets and en-suite baths. The primary suite offers a new veranda and a Chesney wood-burning fireplace flanked by custom built-ins. Finished lower level includes a bedroom, full bath, and laundry and playroom or gym space. The entire gunite heated pool has been completely redone and features automated pool heat and controls, allowing remote operation via iPhone through a Zodiac-style smart system, complemented by a bluestone surround and two additional patios.

1347 Chicken Valley Road, Upper Brookville
$2,950,000
4 Beds ⋅ 6 Baths ⋅ 926494 MLS
This elegant 4-bedroom home (with a 5th bedroom in the finished lower level), Hillwinds, set on 3.78 acres offers a perfect blend of traditional craftsmanship and modern luxury. The sun-filled living formal living room features custom wainscoting, coffered ceilings, soaring to 9.5' feet, and a wood-burning fireplace. The gourmet kitchen boasts marble & granite countertops, brand new high-end appliances (Wolf & Subzero), new wet bar, and a generous island open to the family room-ideal for entertaining. Formal dining room with marble floors and stylish millwork. The serene primary suite offers a vaulted ceiling, spa like marble bath with jet tub and new steam shower, and an impressive walk-in dressing room with custom built-ins. Upstairs spacious bedrooms connected by a Jack & Jill bathroom just beautifully renovated. Additional features include a full house generator, hardwood floors, and extensive updates inside and out. Step outside to your private oasis with lush landscaping, bluestone patios, and a newly appointed heated Gunite pool equipped with a new Jandy Smart System and pool cabana. Outdoor living is enhanced by new stone wood fire feature overlooking the pastoral property. A truly turnkey residence offering comfort, elegance, and privacy in a beautiful setting.

1173 Pine Valley Road, Upper Brookville
$2,700,000
3 Beds ⋅ 4 Baths ⋅ 925151 MLS
Sophisticated Colonial set on two flat, beautifully landscaped acres, offering the best of modern luxury and timeless elegance. Built in 2016, this custom home features an ideal floor plan designed for today’s lifestyle. The main level boasts a Ken Kelly–designed kitchen with premium appliances, a spacious dining area, and a comfortable family room centered around a gas fireplace. A formal living room with gas fireplace and formal dining room provide refined spaces for entertaining. Upstairs, the primary suite is a true retreat, featuring two large walk-in closets, a gas fireplace, and a luxurious ensuite bath. Two additional bedrooms share a beautifully appointed full bathroom, both upstairs baths enhanced with radiant heated floors for added comfort. The fully renovated walk-out basement is an entertainer’s dream—complete with a gym, TV lounge, and bar—offering the perfect space for recreation or relaxation. Step outside to an outdoor oasis featuring a heated gunite saltwater pool with integrated spa (added in 2018), automated pool cover, and a pavilion with outdoor kitchen and TV—perfect for entertaining and effortless indoor-outdoor living. Located in a prime Upper Brookville setting, this home offers peaceful privacy while remaining convenient for commuting, with easy access to nearby train stations, and village amenities. This turnkey home combines the comfort of new construction with the beauty of curated design, set within one of Upper Brookville’s most desirable neighborhoods.

183 Linden Lane, Upper Brookville
$2,500,000
6 Beds ⋅ 5 Baths ⋅ 868377 MLS
Experience exceptional luxury living at this exquisite Tuscan-inspired estate, nestled on 2 acres of lush, professionally landscaped grounds. Fully rebuilt and meticulously renovated in 2005, this private retreat blends timeless European charm with modern sophistication, offering 6 bedrooms, 4 full baths, and 1 half bath, along with an exceptional layout for both grand entertaining and relaxed everyday living. A dramatic two-story entryway with a grand sweeping staircase sets the tone, leading to a formal living room with a charming fireplace and an inviting den—also with a fireplace—perfect for intimate gatherings or quiet moments. At the heart of the home lies the chef’s custom kitchen, thoughtfully designed with a large center island, stainless steel appliances, a farmhouse sink, double ovens, and bespoke cabinetry—tailor-made for culinary excellence and effortless entertaining. Just off the kitchen, a versatile guest suite features a full bath, laundry area, and a bedroom that can also function as an office, providing comfort and convenience for visitors or family members. The lavish primary suite is a private sanctuary, featuring an additional flexible room ideal for use as an office, nursery, bedroom, or fitness space. This suite also includes an expansive walk-in closet and a spa-caliber bath with a steam shower, Jacuzzi tub, and dual private terraces for serene outdoor moments. From the suite, enjoy panoramic views of the grounds—perfect for sunrise coffee or peaceful evenings. A second primary suite on the main level provides added flexibility and privacy for guests or multigenerational living. Each of the generously sized bedrooms offers ample space and natural light, creating stylish, peaceful retreats throughout the home. The finished lower level walks out to the rear grounds and unveils a stunning slate terrace with a covered patio featuring dramatic brick archways—perfect for outdoor dining, entertaining, or simply enjoying views of the rolling lawn. With plenty of room for a pool, this backyard oasis invites resort-style living in your own secluded paradise. Additional features include rich hardwood flooring throughout, a full-house propane generator. Ideally located just 50 minutes from Manhattan, this remarkable property offers luxurious country living with unmatched convenience. Impeccably maintained and truly mint condition—this is a home that defines refined living.

1039 Friendly Road, Upper Brookville
$2,400,000
5 Beds ⋅ 4 Baths ⋅ 966577 MLS
Welcome To #422 Mill River Rd., On A Private Picturesque Location, A Flat Acre Property in Upper Brookville! This extraordinary, fully renovated residence is a true masterpiece of craftsmanship and design, reimagined over the past three years with uncompromising attention to details. From the moment you enter, soaring ceilings and three dramatic skylights flood the interior with natural light, creating an airy, luminous atmosphere. Exquisite custom moldings and architectural details and depth and character throughout, blending classic sophistication with a sleek contemporary aesthetic inspired by refined European design. At the heart of the home lies a state-of-the-art chef's kitchen appointed with top-tier appliances, custom cabinetry, and premium finishes - a seamless balance of beauty and functionality. The primary suite is a private sanctuary, featuring a stunning designer walk-in closet, cathedral ceilings and spa-caliber bathroom with heated floors, a soaking Jacuzzi tub, and a separate glass-enclosed shower-creating the ultimate retreat experience. Thoughtfully designed lower level, offers an unparalleled lifestyle experience a professional home theater, gym, recreation room, billiard room, serene meditation space and sauna with the separate access to the backyard. This level provides both luxury and versatility for entertaining or relaxation. This residence features beautiful hardwood floors, radiant heated bathrooms, spacious guest suite on the first floor, 24 Hr. video security system, Sonos sound system, full house humidifier and water filter. Fenced park like backyard, low taxes and convenient location. This is not simply a home - it is a statement of style, comfort, and elevated living.

422 Mill River Road, Upper Brookville
$2,400,000
5 Beds ⋅ 6 Baths ⋅ 935491 MLS
Special Contemporary 5 bedrooms, 5.5 bath home filled with light and space! From the moment you step into the grand foyer with its soaring cathedral ceiling, this contemporary home impresses with its light and open design. Walls of windows throughout create a seamless connection between indoors and outdoors, bathing every room in natural light. Each of the five bedrooms features its own private bath. The gourmet kitchen is equipped with top of the line viking stainless steel appliances. Just beyond the kitchen, the expansive great room features hardwood floors, a double-sided fireplace, and sliding glass doors that open to a wraparound terrace- an ideal space for gatherings or quiet relaxation. The adjacent dining room completes this elegant and functional main living area. The private primary suite offers a serene retreat with a fully renovated bathroom, plenty of closet space and two walls of windows overlooking the property. Outside, surrounded by nature, is a 3 car garage, and a heated gunite salt water pool. This home is truly unique and special.

40 W View Drive, Upper Brookville
$2,300,000
5 Beds ⋅ 5 Baths ⋅ 819570 MLS
A Legendary Estate with a Sports Sanctuary Step into a world where luxury meets athletic excellence at this exceptional Georgian Colonial estate in Upper Brookville. Set on over two acres along the most prestigious street in the area, this residence offers an unparalleled blend of history, elegance, and recreation. The centerpiece of this property is an oversized indoor sports sanctuary, designed for the ultimate sports professional or enthusiast. With a private tennis court, heated pool, and spa, this estate is built for year-round enjoyment. The expansive indoor court is adaptable for multiple sports, including hockey, basketball, badminton, and more—perfect for training or leisure. The grand circa-1930 home, once owned by Josephine Hartford Douglas of the Great Atlantic & Pacific Tea Company legacy, exudes timeless sophistication. Inspired by her passion for sports, she constructed the original "Playhouse" after finding the renowned Piping Rock Club fully booked for a game of tennis. The recreation building originally housed a swimming pool, tennis court, music room, and drawing room—echoing a heritage of grandeur and entertainment. Inside, the spacious residence boasts a beautifully updated kitchen, a luxurious master en-suite, and elegant living and dining spaces. Guest quarters provide comfort and privacy, while marble baths and exquisite architectural details enhance the home’s superb appearance. This is more than a home—it’s a private sports retreat, a legacy property, and a rare opportunity to own a piece of history in an exclusive setting.

199 Terrace Lane, Upper Brookville
$2,200,000
6 Beds ⋅ 5 Baths ⋅ 923990 MLS
Welcome to 21 Overbrooke Lane, Upper Brookville, a magnificent custom residence nestled on a private road with breathtaking views of a serene pond. This elegant estate offers over 5900 square feet of refined living space set on 1.24 acres of picturesque grounds. As you enter, you’re greeted by a grand custom staircase, intricate millwork, and a hand-painted dome ceiling that reflect true artistry and attention to detail. The open living room features marble floors and floor-to-ceiling windows, flooding the space with natural light and framing stunning views of the tranquil landscape and pond. The kitchen boasts a large center island with generous space for both cooking and gathering. Upstairs, the lavish primary suite serves as a private retreat, offering multiple spacious closets and a spa-inspired bathroom with sweeping views of the pond. With 5 additional bedrooms, 4 additional bathrooms, a home sauna, and a fully finished basement with soaring ceilings, this home is designed for both luxury and comfort. Further highlights include a 3-car garage, expansive water front space - ideal for entertaining, and the peace and privacy that come with its exclusive setting.

21 Overbrooke Lane, Upper Brookville
$1,800,000
5 Beds ⋅ 3 Baths ⋅ 970340 MLS
Private Hilltop Estate with Mother-Daughter Layout in Upper Brookville Located in the prestigious community of Upper Brookville, this exceptional 4,000 sq. ft. home sits on over 2 private acres at the top of a hill, offering outstanding privacy and beautiful natural surroundings. The property borders the Mill River Club and is surrounded by mature trees, creating a peaceful and secluded setting while still being close to everything the North Shore has to offer. This fully renovated Expanded Ranch features a spacious mother-daughter layout. The home offers bright open spaces, high ceilings, and large windows that bring in natural light while showcasing beautiful views of the surrounding landscape. The heart of the home is a large modern chef’s kitchen designed for both everyday living and entertaining. It features a massive waterfall island, custom cabinetry that extends to the ceiling, stainless steel appliances, elegant lighting, and generous space for gathering with friends. The oversized primary suite is designed for comfort and relaxation. It includes a large walk-in closet and a spa-style bathroom designed by Porcelanosa, featuring radiant heated floors, a freestanding soaking tub, a large glass-enclosed rain shower with custom tile work, and a modern double vanity. The home offers 5 spacious bedrooms and 3 beautifully renovated bathrooms, providing flexibility for guests, or home office space. Outdoor living is perfect for entertaining with a fully equipped outdoor kitchen that includes a built-in grill, sink, refrigerator, and stone finishes. The multi-level patio with premium pavers and turf creates an inviting space for gatherings, outdoor dining, or relaxing evenings, while a modern fire feature adds warmth and ambiance to the outdoor setting. The home is accessed through a long private driveway that leads up the hill to the residence, creating a grand entrance while enhancing the privacy of the property. The driveway is wide and spacious, offering ample room for multiple vehicles and guest parking. In addition, the home features a 3-car attached garage, providing convenience, storage, and additional parking. This property stands out for its rare hilltop setting, privacy, and location next to the Mill River Country Club. Opportunities to own a private estate on over two acres in Upper Brookville are truly special.

111 Mill River Road, Upper Brookville
$1,710,000
5 Beds ⋅ 6 Baths ⋅ 889827 MLS
Exceptional Opportunity – Contemporary Home in Sagamore Woods Private Cul-De-Sac Set on five private acres in Sagamore Woods Private Cul De Sac this 5,900 sq. ft. contemporary home presents a rare opportunity to reimagine and renovate to your taste. A circular driveway welcomes you to this architecturally dramatic residence, where soaring ceilings and expansive spaces offer endless potential. The heart of the home is the striking living room with a two-story ceiling, statement fireplace, and a wall of windows that seamlessly brings the outdoors in. Ideal for entertaining, the layout includes a separate breakfast room, an efficient, chef’s kitchen with a center island, and an intimate den for quiet moments. There is an additional bedroom and bathroom on the main level that is the ideal location for a guest suite. On the mid level there is a versatile multipurpose entertainment room perfectly suited for a media room, playroom, or home office. The main-level primary suite offers privacy and comfort, complete with its own sitting room or study. Upstairs are three additional bedrooms, providing flexible living options for family and guests. Scenic circular driveway, large finished basement, three-car garage. Outdoors, the property includes a swimming pool and a charming footbridge that leads to a picturesque, man-made pond—ready to be restored to their full potential. Surrounded by mature trees and open space, the expansive acreage offers a tranquil backdrop with ample room for enhancement. With great bones and a sought-after layout, this is truly an exceptional opportunity to create your dream retreat on the North Shore.

2 West View Drive, Upper Brookville
$1,675,000
6 Beds ⋅ 5 Baths ⋅ 906455 MLS
Incredible opportunity to own and live in prestigious Upper Brookville! Make this amazing 6 bedroom colonial your next dream home. Beautiful layout and flow along with 2 bedroom guest quarters above garage with back stairs off kitchen. Amazing picturesque wide open flowing and very private stunning 2 acre property with pool. All perfectly located on private cul de sac. Property has been in same family since the early 1960’s, please note, property being sold in "As Is condition" and in need of complete updating.

1233 The Knoll, Upper Brookville

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.