Ossining Homes under $500,000

Ossining Homes under $500,000

Welcome to Ossining, New York, a charming village nestled in the picturesque Westchester County. With its rich history, vibrant community, and stunning riverside views, Ossining is an ideal place for those seeking a tranquil yet connected lifestyle. Located just 50 miles north of Manhattan, this hidden gem offers the perfect blend of suburban comfort and urban accessibility.

Ossining is well-known for its diverse array of cultural attractions, including the historic Sing Sing Prison Museum, which tells the story of the infamous correctional facility, and the scenic waterfront parks that offer breathtaking views of the Hudson River. Enjoy leisurely strolls along the riverfront, or immerse yourself in the local arts scene with galleries and theaters that showcase the talents of the community. The village is also home to a variety of dining options, from cozy cafes to exquisite restaurants, ensuring that there’s something for every palate.

For homebuyers seeking affordability without sacrificing quality of life, Ossining offers an impressive selection of homes under $500,000. Whether you’re looking for a charming single-family home, a modern townhouse, or a quaint condo, Ossining’s real estate market accommodates a variety of preferences and budgets. With its excellent schools, family-friendly neighborhoods, and convenient access to public transportation, Ossining is an ideal choice for first-time homebuyers, families, and anyone looking to enjoy the charm of small-town living while being close to the hustle and bustle of New York City.

Discover the delightful community of Ossining, where your dream home awaits!

Newest Ossining Homes under $500,000

53 Hudson Watch Drive, Ossining
$499,000
2 Beds ⋅ 3 Baths ⋅ 1064126 MLS
Welcome to 53 Hudson Watch, a 2-bedroom, 2.5-bath townhouse with an attached garage and 1,629 square feet of well-planned living space in one of Ossining’s most desirable communities. This is a wonderful opportunity to make a home your own in a setting with resort-style amenities and a true sense of community. The main level is designed for both everyday living and easy entertaining. The eat-in kitchen anchors the home, while the sunken living room with a wood-burning fireplace makes a warm and inviting place to gather on cool evenings. Step outside to your private stone patio, a serene spot for morning coffee, weekend grilling, or winding down at the end of the day. A convenient half bath and an open den/office area with a charming window seat complete the first floor, ideal for working from home, a reading nook, or a homework station. Upstairs, the bedroom level offers comfort and convenience, including laundry right where you need it. The primary suite is a true retreat, featuring an en-suite bath with a whirlpool tub and freestanding shower, a spacious walk-in closet, and a private balcony that gives you a second outdoor space of your own. A second bedroom and a second full bath complete the upper level, offering great flexibility for guests or additional workspace. A brand-new water heater and central air add peace of mind and year-round comfort, and the attached garage brings everyday convenience. Life at Hudson Watch extends well beyond your front door. Residents enjoy a community swimming pool, tennis and pickleball courts, and beautifully landscaped grounds in an elevated setting with Hudson River views from the complex. Commuters will appreciate being just 1.1 miles from the Ossining Metro-North Hudson Line station, with downtown Ossining’s waterfront, restaurants, and shops close by. Whether you’re a first-time buyer, ready to downsize, or simply looking for comfortable, convenient living with room to spread out, this home offers a great blend of space, amenities, and location. Bring your vision, add your personal touches, and make it yours.

53 Hudson Watch Drive, Ossining
131 -2 S Highland Avenue Unit #A 5, Ossining
$160,000
1 Beds ⋅ 1 Baths ⋅ 1064424 MLS
Beautifully Updated One-Bedroom Co-op in Ossining Welcome to this charming and beautifully updated one-bedroom, one-bath co-op located on the second floor. Enter into spacious foyer perfect for a variety of uses, such as work space, dining, or reading nook. The updated kitchen features gorgeous white cabinetry, granite countertops, and a butcher-block breakfast bar, perfect for casual dining and entertaining. The kitchen opens to a spacious living room, creating a welcoming and comfortable living space. The updated bathroom adds a fresh, modern touch, while the generously sized bedroom offers plenty of room to relax and unwind. A wonderful opportunity to own a stylish, move-in-ready home that combines comfort, functionality, and modern updates. Don't miss the chance to make this lovely co-op your own!

131 -2 S Highland Avenue Unit #A 5, Ossining
133-3 S Highland Avenue Unit #5B, Ossining
$220,000
2 Beds ⋅ 1 Baths ⋅ 1065268 MLS
Welcome to Highland Terrace, a light-filled, top-floor end unit in a pet-friendly community. This bright and well-maintained two-bedroom apartment features an updated kitchen with granite counters, newer appliances, and a convenient pass-through to the living and dining area. The spacious living room offers plenty of space and great natural light, while both bedrooms include good sized closets. A flexible bonus space off the entrance is perfect for a dining nook or home office. Highland Terrace is a pet-friendly complex (up to two pets allowed) offering assigned parking, an outdoor pool, basketball court, and beautifully maintained grounds. Ideally located just minutes from shops, restaurants, parks, and the Ossining and Scarborough Metro-North stations, making commuting to NYC simple and convenient.

133-3 S Highland Avenue Unit #5B, Ossining
7-10 Briarcliff Drive S Unit #10, Ossining
$330,000
1 Beds ⋅ 1 Baths ⋅ 1058862 MLS
Charming First Floor, One-Bedroom, One Bath Condo in the desirable Briarcliff Woods, where comfort, convenience and a relaxed lifestyle come together! This inviting one-bedroom, one bath condominium offers an excellent opportunity to enjoy easy living in a beautifully landscaped, park-like community. The generously-sized living room has sliding doors to a private patio. Ideally situated in Ossining, Briarcliff Woods provides convenient access to shopping, dining, parks, major roadways and the Croton Harmon Metro-North Station. The complex provides a Jitney to the station for further convenience. Don't miss this outstanding opportunity to make Briarcliff Woods your new home and enjoy easy living with wonderful amenities, such as the large community pool with a club house that offers saunas, a kitchen and bathroom which can be reserved for your private functions as well as tennis and basketball courts.

7-10 Briarcliff Drive S Unit #10, Ossining
1408 Eagle Bay Drive, Ossining
$469,000
1 Beds ⋅ 2 Baths ⋅ 1061876 MLS
Welcome to Eagle Bay, a gated community on the Hudson River. Minutes to Croton Train Station. Recently renovated townhouse has everything you want. The light and bright first floor has an open floor plan and includes a living room with high ceilings/skylight/fireplace and sliders to a large private deck. Large kitchen with stainless steel appliances, washer-dryer closet, large formal dining room- hallway leads to the main bedroom with a walk-in closet and bathroom. The 2nd floor, which includes an additional bedroom/office loft area with a skylight, full bathroom and (the biggest walk-in closet I have ever seen in a townhouse). Unit has central air. Heat is supplied by the Condo (so you have no boiler to worry about) and each unit pays a % per month One detached garage space plus an additional assigned spot #91. Complex features- pool, tennis & basketball courts, clubhouse, gym, gated community etc. Unit also for rent at $3,800. There is an ongoing assessment in the amount of $81 per month.

1408 Eagle Bay Drive, Ossining
21 Knoll View, Ossining
$450,000
2 Beds ⋅ 2 Baths ⋅ 1059219 MLS
Welcome to this beautiful, move-in-ready pet-friendly townhome in the desirable Liberty Knoll community! Featuring a thoughtfully designed open-concept kitchen with abundant natural light, this home offers spacious living areas, comfortable bedrooms, and a finished basement with an inviting entertainment/family room, office, or playroom. The roof and HVAC system were updated in 2021, adding comfort and peace of mind for years to come. Enjoy seamless indoor-outdoor living, tranquil surrounding grounds, and fantastic community amenities, including a swimming pool, clubhouse, and playground. Ideally located near Metro-North stations, with a weekday reimbursement program for transportation to Scarborough Station, as well as major highways, local shops, and dining. Move right in and enjoy everything this Westchester gem has to offer!

21 Knoll View, Ossining
135 South Highland Ave Unit #3B3, Ossining
$223,000
2 Beds ⋅ 1 Baths ⋅ 1058239 MLS
Sun-drenched and spacious, this two-bedroom, one bathroom co-op in the desirable Highland Terrace offers the perfect blend of serene nature and urban convenience. The versatile layout begins with a welcoming foyer, currently utilized as a flexible bonus space. A generous kitchen features abundant cabinet storage and sleek stainless-steel appliances, flowing seamlessly into a bright, airy living room bathed in natural light. The primary bedroom provides expansive closet space, while the flexible second bedroom is ideal for guests, a home office, or additional living area. Residents enjoy exceptional community amenities, including a refreshing swimming pool, basketball court and access to the historic Old Croton Aqueduct Trail—a paradise for outdoor enthusiasts and their pets in this pet-friendly community. Ideally situated less than two miles from the Ossining Metro-North station, this home provides a seamless commute while keeping you close to the natural beauty and vibrant energy of the Hudson River region. An exceptional opportunity for those seeking space, style, and accessibility that combines privacy, luxury, and convenience—a rare opportunity to own a truly turnkey home in one of Ossining's most sought-after complexes. Close to all shopping and amenities. Laundry and storage located in the basement of this building. Come see your new home in the exquisite Hudson Valley! ***Be advised that there are carpet rules. 100% of all BR's & LR are required to have fully padded, tacked down carpet. ***

135 South Highland Ave Unit #3B3, Ossining
135 Main Street Unit #302, Ossining
$215,000
1 Beds ⋅ 1 Baths ⋅ 1057950 MLS
Why rent when you can own? Welcome to your new home! In the heart of the Village of Ossining, is this charming 1-bedroom condo that offers the perfect combination of comfort and convenience! Enjoy a vibrant, walkable lifestyle with easy access to the train station, restaurants, shops, farmers' market, seasonal festivals, waterfront park, community recreation center, library, and more. Pet-friendly for both cats and dogs, with a maximum of two pets per unit. There is also laundry facilities in the basement available to all residents. Each unit has its own storage unit for added convenience. Owners may also obtain parking permits for both Village and train station parking. A new parking garage is currently being built behind the building providing more parking options as seen in the aerial photos. This property is part of the "Fair and Affordable" housing program and is subject to HOME Program affordability requirements. Prospective purchaser(s) must meet applicable income eligibility guidelines, be a first time homebuyer and occupy the unit as their primary residence; investors are not permitted. As of September 2026, household income may not exceed 80% of the Westchester County Area Median Income (AMI), with the following limits: 1 occupant: $95,000, 2 occupants: $108,600, 3 occupants: $122,150 - Income limits are subject to change. There is a $30,000 Westchester County subsidy is available for this unit which has already been accounted for in the listing price. Note: Photos have been digitally enhanced for informational purposes only. Property is being sold as-is. AGENTS: Please review the confidential remarks and all MLS attachments for additional requirements, eligibility information, and further instructions.

135 Main Street Unit #302, Ossining
30 Campwoods Grounds, Ossining
$280,000
2 Beds ⋅ 1 Baths ⋅ 1057825 MLS
What an absolutely excellent opportunity! Come see this adorable cottage in the charming, unique, and AMAZING 44-home community that is Campwoods Grounds! As you walk through the property, you will notice the care that owners put into their homes...The attention to detail, the personal landscaping - in addition to the common areas, and the overall meticulousness is evident across the grounds. This two-bedroom cottage is ready for the lucky buyer(s) to add THEIR own personal touches, but plenty of wonderful features are already in place: A nice-sized eat in kitchen, beautiful hardwood floors downstairs, and a 120-square foot screened in porch are just some of these highlights. There are also two split heat/ac systems for efficiency, one up and one downstairs, as well as a gas furnace if desired for those absolutely frigid winter days/nights. The Campwoods Grounds community also boasts an extensive community garden, LARGE auditorium for neighborhood functions and other events, and a schedule of neighbohood get togethers to enjoy when you want to stay close to home. All of this, so convenient to all, and at a superb price point for the Ossining School District! Taxes with the STAR discount would be $4302/yr.

30 Campwoods Grounds, Ossining
4 Charter Circle Unit #4, Ossining
$225,000
2 Beds ⋅ 1 Baths ⋅ 1041072 MLS
Opportunity awaits at this 2-bedroom, 1-bath bi-level co-op in the High Meadow Cooperative! This home offers comfortable, functional living that has been lovingly lived-in and ready for your personal touch, it's a great chance to build equity and make it your own. The monthly maintenance covers heat, hot water, sewer, trash, and grounds — a simple, low-hassle way to own. Commuters will love the location: about 1 mile to the Scarborough Metro-North station for an easy 45-minute ride to Grand Central, plus shopping and restaurants nearby. Don't miss this value-priced opportunity in a convenient location! Make your appointment today!

4 Charter Circle Unit #4, Ossining
127-1 S Highland Avenue Unit #B5, Ossining
$228,000
2 Beds ⋅ 1 Baths ⋅ 1051780 MLS
Move right into this beautiful top-floor co-op in Highland Terrace! From the moment you enter, you will appreciate the spacious foyer with hardwood floors, suitable as a entryway drop zone, office space, or breakfast nook. Just beyond is the open galley-style kitchen, featuring granite countertops, a tile backsplash, and a double-basin sink with an under-sink water filtration system. The kitchen opens seamlessly to the living and dining area, complete with a breakfast bar that’s perfect for casual meals or entertaining. The living space features BRAND NEW carpeting, which continues into both bedrooms, and the entire unit has been freshly painted. Down the hallway, you will find a tiled bathroom with a BRAND NEW vanity, toilet, medicine cabinet, and light fixture, plus a bathtub that has just been reglazed. The primary bedroom offers ample closet space, and the second bedroom can function as a guest room, home office, or additional living space. Outside, enjoy the beautifully landscaped grounds, complete with a swimming pool and direct access to the Old Croton Aqueduct Trail. Bring your four-legged companions, as Highland Terrace is a pet-friendly community. Enjoy the best of both convenience and surroundings with this ideally situated home, just under two miles from the Ossining Metro-North station and close to the many stores, restaurants, recreation, and natural beauty of the Hudson River area. Come see it today!

127-1 S Highland Avenue Unit #B5, Ossining
58 Hudson View Hill, Ossining
$380,000
1 Beds ⋅ 1 Baths ⋅ 1051520 MLS
Welcome to Hudson View Hills community in Ossining, NY! This adorable 1-bedroom, 1-bath unit offers approximately 832 square feet of comfortable, open-concept living. The inviting layout features a spacious living room, dining area, and kitchen, along with the convenience of in-unit laundry. Enjoy plenty of natural light throughout and step out onto your private, freshly painted unit, deck—perfect for relaxing or enjoying your morning coffee. Additional features include an updated bathroom, ample storage located beneath the unit that is shared, and a private outdoor carport included with the home. The pet-friendly community also offers a pool for residents to enjoy. Conveniently located near Metro-North, the historic Hudson River waterfront, shopping, restaurants, and more. With low common charges and a self-managed HOA, this is a wonderful opportunity to own instead of rent. Come see for yourself why this charming unit is a must-see! Great location for commuting with train within close proximity, restaurants, shopping and tons of Ossining community events through out the year.

58 Hudson View Hill, Ossining
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