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$500,000
3 Beds ⋅ 3 Baths ⋅ 1005194 MLS
Welcome to this beautiful triplex. Taxes do not reflect STAR. It’s a short distance to the Metro North train station and downtown Ossining with it’s restaurants, shops and Farmer’s Market. 3rd floor unit is occupied and can only be shown when the tenant is present for pre-arranged appointments. There is a cistern behind the house with stones on top of it. Please do not disturb it. The garage was probably originally a stable. The water main and sewer lines were replaced in 2025

237 Spring Street, Ossining
$499,000
3 Beds ⋅ 3 Baths ⋅ 1005560 MLS
A rare three-bedroom condo with the kind of extra space that makes daily life feel easier. This spacious tri-level end unit offers a flexible layout that lives more like a home, with ground-level entry, main-level living, a finished lower level, and a detached garage. The main level features wood floors, an updated kitchen with counter seating, a dining area, and a living room with a fireplace and sliding glass doors to the deck. Two bedrooms are located on this level, including the primary suite with full bath, plus an additional full hall bath. Upstairs, a spiral staircase leads to an open loft area, ideal for a home office, reading space, or flex use, with a separate third bedroom beyond. The finished lower level is a standout, offering a large recreation room, laundry area, full bath, storage room, and an impressive workshop space rarely found in condo living. Additional conveniences include a detached garage, an assigned parking spot right in front of the unit, and access to community amenities including a clubhouse, fitness area, sauna, pool, and tennis court. Conveniently located close to Metro-North, shopping, dining, and parks. Freshly painted in most rooms, clean, and ready for its next chapter, this home offers space, function, and value.

4 Steven Drive Unit #1, Ossining
$450,000
3 Beds ⋅ 1 Baths ⋅ 995689 MLS
20 Samstag Ave is the kind of home that sparks ideas the moment you enter. Tucked into an established Ossining neighborhood just minutes from the Hudson River, this classic 2-story Cape-style home with charming dormers and a cheerful red-painted front porch is ready for its next chapter, and for the right buyer, that chapter could be something special. Inside, three bedrooms, a full bath, and 930 square feet of light-filled living space stretch across two levels. The walls have stories to tell, the spaces invite imagination, and every room offers an opportunity to restore, reinvent, or simply bring fresh life to what is already here. The standout living room features warm knotty-pine wood paneling and an incredible mid-century modern built-in shelf and wall divider that feels straight out of another era. It's the kind of architectural detail you simply cannot recreate with a quick trip to a big box store. The kitchen offers a more updated counterpoint with maple-tone cabinetry, a gas range, and tile flooring that flows through the main level, while the upstairs bedrooms tuck under classic Cape sloped ceilings, ideal as cozy retreats or a quiet home office. Outdoors, one of the home's most surprising gifts comes into view: a generous, fully fenced backyard with mature shade trees, a level lawn, and a private rear entry. It's a rare bonus at this price point and a versatile space for entertaining, gardening, or simply enjoying the outdoors. The basement adds another layer of potential. Whether the vision is a workshop, studio, recreation space, or simply more room to spread out, the opportunity is there for someone willing to bring it to life. The location does a lot of the heavy lifting, too. Ossining is one of the Hudson Valley's most loved river towns and one of the smartest commutes north of the city. The Croton Metro-North and other stations on the Hudson Line are just a short drive away, putting Grand Central roughly 45 to 55 minutes from your front door, making this an ideal opportunity. Downtown Ossining is minutes from the house, with its growing roster of restaurants, cafes, and shops, the Sing Sing Kill Greenway, and Louis Engel Waterfront Park where the Hudson and the Palisades stretch out in front of you. Weekends nearby look like the Old Croton Aqueduct trail, Teatown Lake Reservation, Rockefeller State Park Preserve, and the antique-and-eatery rhythm of neighboring Croton-on-Hudson and Sleepy Hollow. For buyers who appreciate homes with character, history, and room to create something personal without giving up an easy commute to NYC, 20 Samstag Ave offers a rare opportunity to shape a space into something truly your own.

20 Samstag Avenue, Ossining
$499,900
3 Beds ⋅ 2 Baths ⋅ 985319 MLS
Truly a standout and seldom available opportunity! Presenting a rare and exceptional offering in one of Ossining’s most coveted communities. This impeccably renovated MOVE IN READY 3 bedroom, 2 full bath ground-level END UNIT residence defines effortless luxury and refined living, featuring one of the most spacious layouts sought after by today’s buyers. From the moment you enter, you are greeted by sophisticated design and superior craftsmanship, featuring all new solid wood shaker-style interior doors with elevated hardware, rich engineered hardwood flooring, high end dimmed light switches, elegant crown molding and designer light fixtures throughout. Every detail has been thoughtfully curated to create a seamless blend of comfort and style. The designer eat-in kitchen is both timeless and on-trend, featuring crisp white shaker cabinetry built to the ceiling, luxurious quartz countertops, impressive crown molding, wood flooring, recessed lighting, Bosch stainless steel appliances w/the dishwasher being panel covered for a seamless look, a large built-in pantry and a wall-mounted pot filler above the stove for filling your large pots at the cooktop. This stunning kitchen is perfect for everyday living and a space you will truly enjoy. The expansive living room is a true showpiece, centered around an attractive wood-burning fireplace, recessed lighting and sliding glass doors that lead to a large newly constructed deck all fenced-in for your added privacy. The outside deck is an outdoor retreat ideal for entertaining, grilling, or quiet relaxation. Impressive spacious primary bedroom, complete with a full en-suite bathroom. Two additional generously sized bedrooms offer comfort and flexibility, each with ample closet space, including one with a walk-in closet. A dedicated walk-in closet in the entry hall enhances the home with extra storage capacity. Each full bathrooms have been tastefully renovated, showcasing fresh, modern finishes. A new top-of-the-line washer and dryer provide added convenience located in the kitchen. Enjoy the unparalleled ease of direct, no-step entry with your own dedicated parking space just outside your door. This pet-friendly community offers resort-style amenities, including a sparkling in-ground pool with expansive sun deck, tennis and basketball courts, and exquisitely maintained grounds adorned with mature trees and vibrant seasonal plantings. A complimentary jitney to the Croton train station further enhances the lifestyle of convenience. And it gets even better - Briarcliff Woods has its own on-site superintendent. Moments away, enjoy the scenic Senasqua Riverfront Park, offering breathtaking Hudson River sunsets, walking trails, picnic areas, beach access, summer concerts, movies and events. Perfectly situated near major highways, shopping, and a diverse array of dining options, this home offers the ultimate in accessibility without compromising tranquility. Homes of this caliber, condition, and location are rarely found, making your find an exceptional opportunity to own a truly turnkey residence in a premier setting.

3 Briarcliff Drive S Unit #9, Ossining
$499,900
2 Beds ⋅ 2 Baths ⋅ 968945 MLS
Offering an open floorplan with sophistication and style filled with designer finishes. This wonderfully maintain unit offers an impressive eat in kitchen with granite counters, stainless steel appliances and rich cabinetry, the dining room flows into the living area complete with fireplace and vaulted ceilings with skylight. The primary bedroom is located on the main level, with vaulted ceilings, custom built-ins closets, beautiful flooring and your own on suit bath, an additional bedroom across the hall with vaulted ceilings and custom built-in closets, hall bath, laundry panty, and enjoy the outside with sliders leading to a private rear deck with awning. Head up the stairs and you'll find an open-loft with an abundance of natural light, and a den or perfect office area. Enjoy all the amenities with your own clubhouse, gym, pool, tennis and basketball court. All of this and move in ready with modern finishes throughout, ideal for both everyday living and entertaining. A convenient location and minutes to the metro north station, restaurants, shopping, parks and parkway. Act now and make this beautiful home your own!

9 Nicole Circle Unit #8, Ossining
$475,000
2 Beds ⋅ 2 Baths ⋅ 960654 MLS
Welcome to 46 Hudson View Hill, a bright and inviting end-unit home set in the quiet and well-maintained Riverview Condos community. This spacious layout offers nearly 1,400 sq ft of comfortable living, highlighted by oversized windows, an abundance of natural light, and the privacy of an "entire floor" floor plan. The main level features an open and airy feel that flows seamlessly into the inviting eat-in kitchen. Designed for both functionality and style, the kitchen offers a breakfast bar, ample cabinetry, and plenty of counter space—making it a perfect hub for daily meals or casual entertaining. Large windows throughout the home provide a serene backdrop of the natural surroundings, flooding the living space with light. A convenient powder room is also located on this level. Upstairs, the home features two generously sized bedrooms, both complemented by great natural light. The well-appointed full bathroom offers dual-entry access from both the primary bedroom and the hallway, providing a suite-like feel for the primary bedroom. A standout feature of this home is the private patio, providing a dedicated outdoor space to enjoy the fresh air. Additional highlights include the quiet end-unit location, baseboard heating, a flexible layout that can easily accommodate a home office, and a pet-friendly policy. Residents of Riverview Condos enjoy wonderful community amenities, including an outdoor pool and beautiful views of the Hudson River from the common grounds—perfect for summer relaxation. Ideally located within the Ossining Union Free School District and just steps from Claremont and Anne M. Dorner schools, this home offers exceptional convenience. Residents are only minutes away from Ossining’s vibrant waterfront, local shopping, diverse dining, and the Metro-North station, providing an easy commute and access to the best of Hudson Valley living.

46 Hudson View Hill Unit #46, 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.