Bennington Real Estate

Bennington Real Estate

Welcome to Bennington, a charming city nestled in the heart of Wyoming County, New York. With its picturesque landscapes and friendly community, Bennington offers a peaceful and idyllic setting for residents and visitors alike.

Located in western New York, Bennington is surrounded by the natural beauty of the region. Rolling hills, lush forests, and serene farmland create a scenic backdrop that is perfect for those seeking a tranquil lifestyle. The area's rich agricultural heritage is evident in the many farms and orchards that dot the countryside.

Despite its rural setting, Bennington is conveniently located near larger cities and amenities. The city is within easy reach of Buffalo and Rochester, providing residents with access to a wide range of shopping, dining, and entertainment options. Additionally, the nearby Finger Lakes region offers opportunities for outdoor recreation, including boating, fishing, and hiking.

Bennington is also home to a close-knit community that values its small-town charm. Residents enjoy a strong sense of community and take pride in their city. The local schools are highly regarded, making Bennington an attractive option for families looking for a safe and nurturing environment for their children.

Whether you're looking for a peaceful place to call home or simply want to escape the hustle and bustle of city life, Bennington offers the perfect blend of tranquility and convenience. Come and discover the beauty and charm of this hidden gem in Wyoming County, New York.

Newest Listings in Bennington

5 Beds ⋅ 3 Baths ⋅ B1701254 MLS

Solid rental in high demand area. Side by side unit. 3 bedrooms and 2 full bath owner unit. 2 bedrooms and 1 bath. Additional barn for parking or storage.

246 Clinton Street, Bennington

4 Beds ⋅ 2 Baths ⋅ B1699547 MLS

40 acres in Bennington? Let's go! Awesome opportunity with frontage on both French and Hoover Roads. House and outbuildings on property that need extensive rehabilitation. Excellent recreational use. Renovate the current home or build new. Selling as-is with all contents on property. Buyer and buyer's agents must sign a Hold Harmless Agreement prior to showing. Delayed negotiations through Monday, July 27, 2026 @ 12 noon.

1214 French Road, Bennington

40 acres in Bennington? Let's go! Awesome opportunity with frontage on both French and Hoover Roads. House and outbuildings on property that need extensive rehabilitation. Excellent recreational use. Renovate the current home or build new. Selling as-is with all contents on property. Buyer and buyer's agents must sign a Hold Harmless Agreement prior to showing. Delayed negotiations through Monday, July 27, 2026 @ 12 noon.

1214 French Road, Bennington

5 Beds ⋅ 3 Baths ⋅ B1699337 MLS

An investors dream awaits! A turn-key, updated, beautifully renovated, clean, and fully rented 3 unit in the heart of Cowlesvillle. Ready for immediate income generation. The list of updates to each apartment is endless over the last 11 years. Each unit has been taken down to the studs and completely rebuilt, to include drywall/insulation (2015/2018/2025), flooring, kitchens (2015/2018/2025), baths (2015/2025), laundry (2022), electrical (2015), plumbing (2015), connection to EC public water (2015), appliances (2016/2025), windows and doors (2015). Roof was a TTO (2014), new gutters (2024). Most recently, Apt 1 was completely renovated in Sept of 2025, and got a new cement step for the entrance just this month. Apt 3 had new deck in 2017, with updated steps just this month. Apt 2 is a 2 story apartment with both bedrooms and the bath on the 2nd floor. Apt 2 furnace 2015, Apt 3 furnace 2016. HWT and pex plumbing lines to all 3 apartments 2015. All separate gas and electric meters (panel in each apartment with main panel in the basement), all tenant responsibility. Landlord currently handles lawn, snow removal, and water. Other than the basics, there could be years of maintenance free living here! The home is connected to public water, there is still a well on the property but it has been disconnected. Incredible opportunity for owner occupied, first time investors, or seasoned investors looking to expand their portfolio. Must have 24+ hrs notice for all showings, so we can get tenant permission to enter. Smile! You're on camera in a couple of the apartments! Showings start immediately, seller reserves the right to set a delayed negotiation date.

170 Bullis Road, Bennington

4 Beds ⋅ 4 Baths ⋅ B1695487 MLS

Welcome to 1589 Bailey Rd, a one-of-a-kind custom-built ranch nestled on 5 acres! Built in 2002, this impressive home offers approx. 3,500 sq. ft. of living space (per plans), featuring 4 beds, 3 full baths & 1 half bath. A property like this is nearly impossible to duplicate at today's construction costs. Step inside to an inviting open-concept layout with soaring vaulted ceilings & oversized rooms throughout. The spectacular GREAT room is the centerpiece of the home, showcasing a massive floor-to-ceiling stone fireplace w/ a beautiful red oak mantel, expansive backyard views & enough space for even the largest sectional. The formal DR is ideal for hosting holidays & flows seamlessly into the spacious kitchen, complete with solid hickory cabinetry, abundant storage, generous counter space, a commercial-grade range & professional exhaust hood. Just off the kitchen you'll find a convenient 1/2 bath, 1st floor laundry, & access to the attached 2.5-car garage. The primary suite accommodates a king-size bed & walk-in closets plus a private ensuite featuring a Jacuzzi tub, marble tile & walk-in shower. Another 1st floor bed also enjoys its own private full bath, making it perfect for guests or multigenerational living! The walkout lower level expands your living space w/ beds 3 & 4, both featuring egress windows, another full ensuite bath, a cozy wood-burning fireplace, 2 additional rooms ideal for home offices & wine cellar. Radiant Heated floors, HWT (2025), AC (2024) & permanent generator. Outside, the possibilities continue - the shop has space for equipment or hobbies. The heated greenhouse has its own dedicated well, so easy to grow your own produce. The property has gorgeous grounds, multiple sheds, mature fruit trees, nut trees & plenty of room to create the self-sufficient lifestyle you've been dreaming about—all surrounded by the privacy & beauty of nature. Whether you're looking for room to grow, space to pursue your passions or simply a peaceful place to call home, this home delivers a lifestyle that's hard to find. 15 mins to Rt 400 & EA. Bennington Town & Attica Schools. This one is a MUST SEE!! Open House SUN 7/12 from 1-3 PM!

1589 Bailey Road, Bennington

4 Beds ⋅ 3 Baths ⋅ B1691144 MLS

Wake up to the sound of the water and sip your morning coffee from your back deck overlooking the lake. This is the lifestyle 13 n Shore delivers. Tucked away in a private setting with a true backyard oasis, this 4-bed, 3-bath multi-level home blends comfortable everyday living with spectacular outdoor access. The main level welcomes you with a bright, open living room featuring a fireplace and huge windows that flood the space with natural light. The eat-in kitchen is outfitted with stainless steel appliances and flows seamlessly to the back deck through a sliding glass door, an effortless setup for morning routines or entertaining. The primary bedroom is a true retreat, complete with a large walk-in closet and a private bath featuring a separate shower and bath. Another bedroom completes this level. Head downstairs to a versatile lower level that's ready for whatever you need it to be, a fully equipped in-law suite, a teen hangout, or a media room. With gas and water hookups already in place, adding a second kitchen is a breeze. A bedroom, full bath, and laundry complete this level, along with its own sliding door to a lower deck overlooking the lake. The basement level offers two large windows, plenty of natural light, and side-by-side closets with sliding mirror doors, making it a 4th bedroom or bonus flex space. Beyond your door, Highland Glens delivers an outdoor lifestyle like no other. Three stocked fishing ponds, kayak or non-motorized boat, explore over 300 acres of hiking and ATV trails, or simply enjoy the peace and privacy that this community is known for. OPEN HOUSE Saturday 6/20/26 11am-1pm

13 N Shore Drive, Bennington

Great opportunity to build your dream home! Over 2 acres with 260 ft of frontage in the Attica School District. Escape the hustle and bustle and secure your own slice of nature with this pristine 2 acre lot. Perfectly balancing seclusion and convenience, this property is ready for your vision.

Clinton Street, Bennington

4 Beds ⋅ 2 Baths ⋅ B1679861 MLS

Set on a stunning 17-acre parcel, on a country road located on the edge of a wooded area this charming and unique 4-bedroom, 2 full bath 'Geodesic Home' offers the perfect blend of privacy, nature, and comfort. Surrounded by mature gardens and scenic hiking trails, the property invites you to enjoy the outdoors year-round. A large pond provides the ideal setting for fishing, swimming, or simply relaxing by the water. Inside, you’ll find a beautifully updated kitchen with granite countertops that serves as the heart of the home, along with spacious living areas filled with natural light and beautiful views of the property. Two additions added a breakfast room and a sunroom for extra living space! Based on seller measurements, the total square footage is 1,825, which includes this Sun Room/Breakfast Room addition not currently reflected in public records. The four bedrooms offer ample space for sleeping, a home office, or a home gym. Large living area for entertaining family and friends or enjoying quiet moments. Exterior decks surround the home for more entertaining or relaxing! The detached four car garage and heated workshop is a hobbyist's dream! The garage is a perfect building for lots of storage and hobbies! Garage has heat, water, and electric. Whether you are looking for a peaceful retreat or a place to entertain, this property delivers space, serenity, and endless possibilities. The home also offers multiple heating and air conditioning options, a 1/2 house generator, a newer hot tub to enjoy, and a Kohler awning on the back deck. Mature gardens throughout and a greenhouse for extending your growing season! This is a true gem, one of a kind!

311 Ortner Road, Bennington

Incredible commercial lot available in Bennington's business district. High visibility and excellent location. Perfect opportunity to build your own business.

Alleghany Road, Bennington

4 Beds ⋅ 1 Baths ⋅ B1662113 MLS

Good Bones and History is what you get with 270 Clinton St. This home has had the same family for over 100 years. Now it is time for a fresh start and the next chapter of history. Sitting on just over an acre this home features newer furnace and HWT. No space was spared as this house has room after room. 5 rooms upstairs with two entry ways. 6 more rooms downstairs with spacious dining room at the center of the home. first floor laundry is nice plus. This is an estate, New York State has final say on price, at this point any offers below $50k would be a waste of time. Property being sold as is, without warranty as to condition, express or implied. Utilities are currently off and will not be turned on prior to closing. Buyer responsible for septic. This property needs a lot of work, you are touching every surface. Offers will be reviewed as presented.

270 Clinton Street, Bennington

Start Your Search