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$899,000
4 Beds ⋅ 3 Baths ⋅ 1024630 MLS
A charming split-level home set on land that was once part of the historic Waldheim Estate of James and Ellin Speyer. Tucked into a peaceful setting just minutes from the heart of Briarcliff Manor, this inviting property reflects the area's rich history while offering the comfort of everyday living. Offering 4 bedrooms and 3 bathrooms, the home is filled with warmth, character, and a wonderful connection between indoor and outdoor living. From the moment you arrive, the tranquil surroundings make a lasting impression. Mature trees, established gardens, and natural landscaping provide exceptional privacy and create a beautiful backdrop that changes with the seasons—from colorful spring blooms to vibrant autumn foliage. Thoughtfully maintained over the years, the gardens offer a peaceful retreat that's as beautiful as it is easy to enjoy. Inside, soaring ceilings and abundant natural light enhance the home's welcoming atmosphere. The main living area is centered around a beautiful fireplace, creating a cozy gathering place, while large windows bring the beauty of the outdoors inside. The comfortable layout flows effortlessly to the outdoor living spaces, making everyday living and entertaining equally enjoyable. Step outside to the flagstone patio, where you can enjoy outdoor dining, entertain family and friends, or simply relax while taking in the peaceful surroundings. The in-ground cement pool complements the backyard, providing the perfect setting for warm summer days. Whether hosting gatherings or enjoying a quiet morning coffee surrounded by nature, the outdoor spaces offer endless opportunities to relax and unwind. Lovingly cared for over the years, the home presents an opportunity for its next owner to bring their own vision while enjoying its timeless charm, generous living space, and exceptional setting. Located just minutes from the many amenities of Briarcliff Manor, you'll enjoy access to Briarcliff Manor Recreation, nearby parks, scenic hiking trails, top-tier golf courses, charming shops, and local restaurants. The nearby Scarborough Train Station provides a convenient Hudson River commute to New York City, making this peaceful retreat as practical as it is picturesque. 54 Holbrook Road is more than a home—it's a place where nature, comfort, and community come together in one of Westchester's most desirable locations.

54 Holbrook Road, Briarcliff Manor
$639,500
4 Beds ⋅ 2 Baths ⋅ 1021344 MLS
Welcome home to this beautifully maintained 4-bedroom, 2-bath Cape Cod nestled in one of the desirable Hudson Valley River towns. Combining classic charm with everyday comfort, this move-in-ready home features gleaming hardwood floors, spacious living areas, and a flexible floor plan perfect for today's lifestyle. The private backyard offers a peaceful retreat with a patio ideal for outdoor dining, entertaining, or simply relaxing. Experience the best of Hudson Valley living with convenient access to the scenic Hudson River waterfront, parks, hiking and biking trails, local restaurants, shopping, and year-round community events. Whether you're commuting, exploring the outdoors, or enjoying the vibrant Rivertown lifestyle, this home offers the perfect balance of tranquility and convenience. Don't miss this opportunity to own a beautiful home in one of the Hudson Valley's most sought-after communities.

42 Pershing Avenue, Ossining
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 1021711 MLS
"Living at Beechwood has been a truly special experience. The beauty, serenity, and wonderful sense of community make it a place that feels like home from the moment you arrive. Some of my favorite memories have been simply sitting on the balcony, watching breathtaking sunsets paint the sky, greeting the peaceful sunrise with a cup of coffee, and enjoying the quiet glow of the moonlight in the evenings. The natural beauty that surrounds the home changes with every season, creating a tranquil retreat that is both inspiring and relaxing. Combined with the warmth and kindness of the lovely neighbors, Beechwood offers a rare lifestyle where every day feels peaceful, welcoming, and connected to nature." (Seller's words) 32 Beechwood Way is part of an 80-acre private parkland. Beechwood was designed by Frederick Law Olmsted (who also designed Central Park in NYC and Prospect Park in Brooklyn). Its expansive lawns, grove of large beech trees, imported trees, and Italianate Garden with an alcove, fountain, and small pool with wisteria-covered gazebo have been well-preserved. Serene, tranquil, alluring is at the essence of Beechwood. Natural light abounds from large windows in living room and sky lights in entrance foyer. The primary bedroom has en-suite bath, double walk-in closet (it is a room all its own!), walk-in-shower for ease in entry/exit, & private terrace with seasonal Hudson River views. Scarborough Station/Metro North is less than a mile away (.9 miles). Working remotely? Two additional bedrooms on main & lower level easily accommodate your lifestyle. Efficient & responsive resident property manager. Entire house painted within the year. Floors refinished and stained in the last 2 years. Whole-house water filtration system installed less than a year ago. Roof less than 3 years old. Residents at Beechwood may avail themselves of the Olympic-size pool, library, & elegant formal ballroom to celebrate life events in style.

32 Beechwood Way, Briarcliff Manor
$419,000
1 Beds ⋅ 1 Baths ⋅ 1025908 MLS
Welcome to Eagle Bay, a sought-after gated community overlooking the Hudson River in Ossining. This beautiful 1st floor unit is freshly painted and offers the perfect combination of privacy, convenience, and resort-style living. Relax on your private deck while enjoying a peaceful natural setting just minutes from Metro-North, shopping, and dining. The bright, open floor plan features hardwood floors throughout and a wood-burning fireplace that creates a warm and inviting living space. The updated eat-in kitchen is appointed with granite countertops, and the bedroom features a walk-in closet while the primary bath offers a relaxing Jacuzzi tub. Additional highlights include an assigned parking space and the washer/dryer in unit. Residents of Eagle Bay enjoy an exceptional lifestyle with outstanding amenities, including a swimming pool, tennis and basketball courts, clubhouse, fitness center, and playground. Ideally located near the vibrant villages of Ossining and Croton-on-Hudson, you'll have easy access to restaurants, shopping, parks, and Metro-North for a convenient commute to New York City.

101 Eagle Bay Drive, Ossining
$1,045,000
4 Beds ⋅ 3 Baths ⋅ 1023043 MLS
Welcome to this beautifully renovated Dutch Colonial, where timeless charm meets modern comfort and breathtaking Hudson River views create an unforgettable setting. Thoughtfully redesigned, the sun-filled chef's kitchen is the heart of the home, featuring crisp white cabinetry, expansive quartz countertops, abundant storage, and a seamless flow into the dining and living areas, perfect for everyday living and effortless entertaining. The spacious living room is warm and inviting, highlighted by a beautiful fireplace and elegant French doors that open to a covered patio, creating an ideal space to gather with family and friends. Just beyond, the expansive west-facing deck showcases spectacular Hudson River vistas and provides the perfect place to unwind while taking in stunning sunsets. A private office or study with sliding glass doors to the deck allows you to work while enjoying the scenic surroundings, and a beautifully renovated full bath completes the main level. Upstairs, the primary suite is a true retreat, offering a generous walk-in dressing area and a spa-inspired bath with a soaking tub, separate shower, and picturesque views. Three additional spacious bedrooms and another beautifully updated full bath provide ample room for family and guests. Additional highlights include a built-in speaker system throughout much of the home, an expansive yard, abundant parking, an oversized two-car garage, and a full basement, offering endless possibilities for storage, recreation, or future living space. Combining exceptional renovations, generous living spaces, and captivating vistas, this is a home you'll want to experience in person.

27 Ryder Road, Ossining
$1,150,000
4 Beds ⋅ 3 Baths ⋅ 1013378 MLS
Some homes ask you to imagine what they could be. This one is already there and waiting for you. This classic colonial has been lovingly updated and impeccably maintained by owners/designer who cared about every detail. Large, sun-drenched rooms, a layout that feels both timeless and completely livable, and the big-ticket items already handled: new roof, new HVAC, new kitchen and appliances, new bathrooms, new garage doors, mostly new windows, new Trex deck, freshly painted throughout, and beautiful landscaping. The to-do list has already been done! The kitchen tells you everything about how this home was tended. Expanded windows pour light across generous counter space, the pantry closet and large cabinets keep things organized, and an induction cooktop and eat-in area make everyday life feel a little more considered. Sliding doors open directly to the new Trex deck, because good kitchens don't end at the walls. Upstairs, four well-proportioned bedrooms and two fully updated bathrooms offer real comfort. The primary bedroom includes a stunning new bathroom and a fabulous walk-in closet that makes the everyday routine feel a little more special. On the first floor, a powder room and a flexible den with fireplace work as a home office, playroom, or guest room, depending on what this season of life calls for. A sunny mudroom and laundry room with its own separate entrance off the kitchen keep the household running smoothly, and the two-car garage rounds out a home that was designed to actually live in. The walk-out lower level adds a chapter still to be written. Full, unfinished, with high ceilings and direct outdoor access and windows, it's ready for whatever you decide it should become. The flat, beautifully landscaped backyard with a fire pit patio turns an ordinary evening into a reason to stay outside a little longer. Less than a mile to the Scarborough Train Station for an easy city commute, Briarcliff Manor recreation right down the road with pool, tennis, pickleball, and summer camps, and the award-winning Ossining School District, this is a community that feels like home.

629 Scarborough Road, Briarcliff Manor
$675,000
3 Beds ⋅ 2 Baths ⋅ 1013329 MLS
Make every day, one of leisure and delight. Perched above the Hudson River, discover this impeccably maintained, spacious 3 bedroom, 2 full bath, at the highly coveted Scarborough Manor. High on the 6th floor, this corner unit has 9ft ceiling and oversized rooms, creating a most expansive and tranquil oasis. Its light wood floors, custom blinds/shades, sleek kitchen, and renovated baths mingle luxury with practicality. Best of all, you can enjoy majestic vistas from your private terrace and banquet of large windows. Allow yourself to be treated to a daily lifestyle that nurtures your spirit, as you enjoy the many amenities the complex offers: Clubhouse with fitness center, sauna, billiards, library, ping-pong, and event space • Outdoor Heated Pool surrounded by mature trees with Hudson River views • Beautiful Park-Like Grounds with walking paths and benches • 24/7 Gated Security for peace of mind and to accept your packages • Free Outdoor Parking for all (Indoor parking is wait listed at $85 per month) • Full Generator no power outages. Hallways redecorated one year ago with contemporary wallpaper and carpeting • Unique Features: Convenient laundry on each floor • New HVAC units in LR, Dining Room, and Bedrooms • New windows throughout • New lobby restoration underway • Storage units are on a wait list and the rent is ($30-$50/month). Scarborough Manor offers the best of both worlds – a tranquil, riverside setting with easy access to both the Scarborough and Ossining Metro-North stations, Route 9, and nearby shops and restaurants.

16 Rockledge Avenue Unit ##6E-1, Ossining
$625,000
3 Beds ⋅ 3 Baths ⋅ 1013828 MLS
A tri-level gem, just minutes from downtown Ossining, this three bedroom home is perfect for those who need more space, but want less maintenance. Park either in the driveway or pull into the garage (with extra storage space). There is additional parking shortly down the street. Entering the home on the first floor, you will find a flexible bonus room, great for storage, an office or more. There are multiple closets here as well. Up one level is the open living and dining room. Centered on a wood-burning fireplace with granite hearth and featuring new floors, this is a wonderful space. There are sliding doors here, out to the rear deck and tree ensconced lawn beyond. The eat-in kitchen is well laid out, with good counter and cabinet space. Off of the kitchen, find the large balcony - a great place to enjoy a cup of tea in the early morning, or something a little stronger at the end of the day. Also on this floor is the hall bathroom and the large laundry closet. Up one more level, we reach the bedrooms. The primary bedroom, with an ensuite bathroom that has a tub and a shower, has a deep walk-in closet. In this room, and every bedroom, natural light shines through oversized windows with views out to trees. The second and third bedrooms share a full hall bath with a tub. In Ossining, there are few options for three bedroom condominiums. The Deerfield community has a beautiful, large pool - a perfect place to sunbathe even if you don't swim. There are also walking trails, easily accessible from this unit. All of this, just a short drive to shopping, restaurants and parks, and easily accessible to commuting by train or highway. What more can you ask for?

83 Deerfield Lane, Ossining
$3,500,000
10 Beds ⋅ 6 Baths ⋅ 999615 MLS
Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing sophistication or convenience, this is the ultimate retreat. From the moment you arrive, the estate feels transported from another era. A winding cobblestone driveway crafted from salvaged historic Bronx street stones loops through rolling lawns, curated gardens, and towering trees before revealing the magnificent manor overlooking its own private 3-acre pond. The original boathouse sits at the water’s edge, while a heated pool, tennis court, Japanese garden, orchard, vegetable and berry gardens, greenhouse, and heated pottery studio create a lifestyle reminiscent of a private European country estate. The nearly 9,000-square-foot residence is rich with warmth, grandeur, and unforgettable architectural detail. The awe-inspiring Great Room is nothing short of spectacular, anchored by a massive stone fireplace, soaring 40-foot oak-beamed ceilings, and dramatic walls of glass opening to sweeping pond views. Every room tells a story, from the stately oak-paneled library and elegant entertaining spaces to intimate sitting rooms, hidden carved staircases, and beautifully preserved plaster walls that showcase the home’s old-world craftsmanship. Designed for luxurious multi-generational living and grand entertaining alike, the estate features 10 bedrooms spread across thoughtfully designed wings, including guest accommodations and private caretaker quarters. The newly renovated primary suite rivals a five-star hotel, complete with its own fireplace, lounge/office with kitchenette, spa-like bath, dressing room, and tranquil views over the grounds. Nearly every fireplace throughout the home is operational, bringing warmth and romance to every season. Three separate tax lots, including an additional lot near the guest house, add a level of rarity and long-term value seldom found in estates of this caliber. Modern upgrades quietly support the property’s timeless elegance, including heated garages, multiple propane generators, upgraded well systems, mixed central air, and extensive utility and storage spaces. Private, historic, and impossibly romantic, this is more than a home. It is a destination, a lifestyle, and a once-in-a-generation opportunity to own one of the Hudson Valley’s most magical estates, all within easy reach of New York City.

335 Croton Dam Road, Ossining
$1,750,000
9 Beds ⋅ 8 Baths ⋅ 1005133 MLS
Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities. The beautifully renovated 5,337-square-foot Main House features 5 spacious bedrooms and 3.5 bathrooms, showcasing refined craftsmanship and sophisticated updates throughout. At the center of the home is a stunning chef’s kitchen equipped with premium Sub-Zero appliances, designed for both everyday living and elegant entertaining. Recent upgrades include new windows, a new roof, and solar panels on the Main House, offering enhanced efficiency and sustainability. Beyond the main residence, the estate includes a charming 1,020-square-foot Guest House with 3 bedrooms and 2 bathrooms, ideal for long term guests, or private office space. A separate Gate House with 2 bedrooms and 2 bathrooms adds even more versatility and privacy. Surrounded by lush grounds and mature landscaping, the property offers resort-style amenities including an in-ground swimming pool and private tennis courts, creating a true retreat just outside the city. A rare opportunity to own a distinguished estate that delivers privacy, luxury, and convenience in one of Westchester County’s most coveted locations.

51 Pinesbridge Road, Ossining
$999,900
3 Beds ⋅ 3 Baths ⋅ 981714 MLS
Set in one of Briarcliff Manor's most distinctive communities, this pond-front three-bedroom townhouse offers a rare combination of natural beauty and thoughtful updates. Enjoy peaceful pond views, seasonal views of the Hudson River, and 33 acres of Olmsted-designed grounds with lush gardens and mature landscaping as your backdrop. The recently updated eat-in kitchen anchors the bright main level with a functional, open layout, flowing into the dining room and living room with a French door to the patio—overlooking the pond. Powder room, laundry, and access to the two-car attached garage complete the first floor. Upstairs you’ll find the primary bedroom suite with pond views and large walk-in-closet. The primary suite includes 5 spacious closets and an ensuite bathroom with double vanity, tub, and shower. Two additional spacious bedrooms and a full hall bath finish the second level. The lower level offers finished storage space and recreation room. 2443 sq footage First & Second floor plus 909 sq ft Recreation Room in lower level for a total of 3352 sq ft. Beechwood's 37-home community on 33+ acres includes an Olympic-sized pool, tennis courts, and a historic mansion with a ballroom and library available to residents. A full-time on-site manager oversees the grounds. Less than half a mile to Scarborough Metro-North, with shops and park nearby.

29 Beechwood Way, Briarcliff Manor
$2,900,000
7 Beds ⋅ 7 Baths ⋅ 942815 MLS
Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country setting less than an hour on the express train from NYC. The main residence features a warm and welcoming checkerbox marble foyer opening to elegant formal rooms, and flowing to a cozy bar and family room overlooking the grounds through walls of windows. A sparkling chef’s kitchen, convenient butler’s pantry, and finely restored period details make the home ideal for both everyday living and entertaining. Upstairs, there is extensive accommodation, including a spacious primary suite with elevated views of the private lake, along with three additional bedrooms and multiple baths. A generous home office and dedicated home theater provide exceptional flexibility for work and leisure. The uppermost floor offers two more expansive bedrooms, or flex space for a creative studio. Beyond the main residence, the estate includes a 5-car garage connected to a stables complex by an elegant breezeway. An additional and completely remodelled 1-bedroom apartment above the stable wing, and a charming separate 2-bedroom stone cottage provide versatility for guests, multigenerational living, or rental/Airbnb income. Landscaped grounds with nature paths, sweeping lawns, and exceptional stonework make this a true retreat. Located in the quaint riverfront community of Ossining, known for its scenic Hudson views, vibrant downtown, and abundant parks and trails, this property offers a rare opportunity to own a thoughtfully preserved and modernized Hudson Valley estate.

83 Somerstown Road, Ossining

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.