Homes for Sale near Mt. Anthony Union Middle School

/35
$379,900
- 4 Beds
- 2.5 Baths
- 2,530 Sq Ft
93 Russett Dr, Bennington, VT 05201

Welcome to this charming mid-century home set on 1.27 acres, offering 4 bedrooms and 3 bathrooms. This property blends character, functionality, and unique design throughout.At the heart of the home, a beautiful open concept kitchen and living area creates the perfect space for gathering and entertaining. A stunning fireplace anchors the room, offering warmth and ambiance whether you’re

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 416-3661

93 Russett Dr, Bennington, VT 05201
/42
$565,000
- 3 Beds
- 2 Baths
- 1,748 Sq Ft
211 Rod and Gun Club Rd, Shaftsbury, VT 05262

Welcome to Rod and Gun Club Rd. Offering 1748 sq ft, with a full useable basement, sitting on 4.43 acres of land, with a 3-bay garage with carport as well as, an attached 2-car garage, a barn with stalls if you want to have some animals. This newly renovated ranch style home with thoughtful design offers 3B,2Bath, with a spacious and flexible layout with a fireplace with a gas insert in the

Wendy Larson

Hooscik Realty

(802) 526-6197

211 Rod and Gun Club Rd, Shaftsbury, VT 05262
/52
$725,000
- 4 Beds
- 2 Baths
- 2,424 Sq Ft
2 Cold Spring Rd, North Bennington, VT 05257

Welcome to 2 Cold Spring Road a cherished homestead steeped in history, beauty, and Vermont tradition. This 1785 Center Hall Colonial has been in the same family for generations and is now ready for its next chapter. With five spacious bedrooms, two full baths, and a classic layout that captures the warmth of country living, this property offers timeless charm with endless potential.Set on 50

Brooke Thomson Drew

Mahar McCarthy Real Estate

(802) 810-8873

2 Cold Spring Rd, North Bennington, VT 05257
/60
$875,000
- 4 Beds
- 3 Baths
- 2,462 Sq Ft
636 Dexter Rd, Shaftsbury, VT 05262

In 1922, poet laureate and Shaftsbury resident Robert Frost was inspired by the bucolic local backroads to write “Stopping by the Woods on a Snowy Evening." The Dexter Road Farmhouse, dating back 225 years, remains a testament to the enduring charm of Vermont and the simpler rhythms of country life. Nestled at the end of a serene, tree-lined town road, this charming 1800 farmhouse captures the

Kristin Comeau

TPW Real Estate

(802) 727-7584

636 Dexter Rd, Shaftsbury, VT 05262
/60
$405,000
- 2 Beds
- 2 Baths
- 1,729 Sq Ft
1260 Cider Mill Rd, Shaftsbury, VT 05262

Tucked away on a peaceful country road in Shaftsbury, this 2-bedroom, 2-bath contemporary ranch offers the perfect balance of privacy and convenience—just 10 minutes to Bennington. Set on 1.5 acres, the home features easy one-level living with an open, light-filled layout. The heart of the home is the bright, sunny kitchen with ample workspace and modern finishes. The spacious primary suite

Vicki Wilson Maple Leaf Realty

1260 Cider Mill Rd, Shaftsbury, VT 05262
/27
$259,000
- 3 Beds
- 1 Bath
- 1,612 Sq Ft
895 Barber Pond Rd, Pownal, VT 05261

Turnkey and impeccably maintained, this charming 3-bedroom, 1-bath ranch offers effortless single-level living on a picturesque 1.3-acre lot. Inside, you’ll find gleaming hardwood floors and a thoughtfully updated interior, highlighted by a fully renovated kitchen and bathroom that blend modern finishes with everyday functionality. The home is truly “neat as a pin,” reflecting pride of ownership

Faith Rhodes Maple Leaf Realty

895 Barber Pond Rd, Pownal, VT 05261
/45
$295,000
- 3 Beds
- 1 Bath
- 1,344 Sq Ft
951 Gage St, Bennington, VT 05201

This charming village home offers the perfect blend of tranquility and convenience. Situated on a spacious double lot, you'll enjoy plenty of room for outdoor activities and relaxation, all while listening to the soothing sounds of a nearby babbling brook. The home is well maintained and located at the edge of town, providing easy access to amenities yet offering a peaceful back

Dan Mason Perrott Realty

951 Gage St, Bennington, VT 05201
/60
$425,000
- 3 Beds
- 2.5 Baths
- 1,764 Sq Ft
2603 N Pownal Rd, Pownal, VT 05261

Perched like a storybook retreat and affectionately known as “the treehouse,” this one-of-a-kind home rises from it’s owner-built frame, nestled atop a natural rock outcrop with sweeping views of the Taconic Range.Inside, the home unfolds with a sense of wonder. Sunlight dances beneath a dramatic 20-foot ceiling, softly illuminated from above, while a living rock outcrop emerges through the

Lindsey Martin Maple Leaf Realty

2603 N Pownal Rd, Pownal, VT 05261
/30
$219,000
- 4 Beds
- 1 Bath
- 1,127 Sq Ft
20 Sage St, North Bennington, VT 05257

Charming home in the heart of the Village of North Bennington, set on a beautiful village lot and offering solid bones with great potential. This well-maintained property features 4 bedrooms and a 3/4 bath, along with a first-floor bonus room. Wood floors lie beneath the carpet, ready to be revealed. Laundry hookups are in place for added convenience. Some updates are needed, providing an

Abi Gregorio

20 Sage St, North Bennington, VT 05257
/47
$845,000
- 5 Beds
- 5.5 Baths
- 3,875 Sq Ft
1629 Mann Hill Rd N, Pownal, VT 05261

Facing west to capture breathtaking mountain views and unforgettable sunsets from nearly every room, this stunning modern farmhouse seamlessly blends timeless character with thoughtful updates. Rich hardwood floors and cozy alcoves create warmth and charm throughout, while original beams in the living room add a touch of history and authenticity. The spacious layout offers 5 bedrooms, each with

Kelley Mccarthy Mahar McCarthy Real Estate

1629 Mann Hill Rd N, Pownal, VT 05261
/50
$465,000
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
1284 Granger Hollow Rd, Shaftsbury, VT 05262

Magnificent setting on 4 scenic acres in rural Shaftsbury, this classic 1979 Saltbox offers the perfect blend of Vermont charm, functional space, and meaningful updates. Surrounded by rolling landscape and mountain views, the vibe is peaceful and inviting—ideal for those seeking privacy without sacrificing convenience. Inside, the home features a warm and welcoming layout highlighted by natural

Jenifer Prouty Hoffman Hoffman Real Estate

1284 Granger Hollow Rd, Shaftsbury, VT 05262
/55
$239,500
- 3 Beds
- 2 Baths
- 1,280 Sq Ft
38 Cyr Ct, Bennington, VT 05201

This classic 1975 ranch offers comfortable single-level living with great potential to make it your own. Featuring three bedrooms, including a primary with its own bath. The home provides a functional layout suited to a variety of lifestyles. A spacious living area and eat-in kitchen create a welcoming foundation for everyday living and entertaining. While the home could benefit from some

Catherine Cairns Maple Leaf Realty

38 Cyr Ct, Bennington, VT 05201
/49
$275,000
- 2 Beds
- 1 Bath
- 1,124 Sq Ft
42 Overlook Rd, Pownal, VT 05261

Tucked away in a rural setting, this 2 bedroom, 1 bath, ranch style home offers spectacular views overlooking Barber Pond. Inside, you’ll find a warm and inviting cabin style interior, complete with natural wood accents and a Vermont Castings wood stove set on a stunning stone hearth for cozy ambiance during the colder seasons. The galley style, eat-in kitchen has rustic cabinetry, water views, a

Casey Scott Southern Vermont Realty Group

42 Overlook Rd, Pownal, VT 05261
/37
$525,000
- 3 Beds
- 3 Baths
- 3,182 Sq Ft
4 Stonehedge Dr, Bennington, VT 05201

Beautiful 3-bedroom, 3-bath home offering stunning views from a spacious two-tier deck-perfect for relaxing or entertaining. Designed for comfortable main-level living, the home features a generous primary suite and an open, light-filled living room with a dramatic wall of windows that captures the surrounding scenery. Warm and inviting, the home includes two gas fireplaces, gleaming wood floors,

Kelley Mccarthy Mahar McCarthy Real Estate

4 Stonehedge Dr, Bennington, VT 05201
/32
$275,000
- 1,680 Sq Ft
318 North St, Bennington, VT 05201

Versatile mixed-use property with strong potential as a duplex or owner-occupied investment in a highly visible downtown North Street location. Currently configured with a beautifully renovated 1-bedroom, 1-bath apartment on the second floor and a spacious first-floor commercial unit, this property offers multiple paths for income and future use. Zoning supports multi-family, single-family, and a

Jenifer Prouty Hoffman Hoffman Real Estate

318 North St, Bennington, VT 05201
/40
$289,000
- 6 Beds
- 4 Baths
- 2,520 Sq Ft
111 Booth Terrace, Bennington, VT 05201

Exceptional opportunity to own a beautifully maintained duplex in the heart of Bennington. Each spacious unit offers 3BR and 1.5BA, featuring warm wood floors, generous living space, and thoughtful layouts that appeal to both tenants and owner-occupants alike. Renovated and updated through the years, the property has been meticulously cared for and has an organized, efficient setup throughout.

Abi Gregorio

111 Booth Terrace, Bennington, VT 05201
/7
$997,000
- Land
- 0.53 Acre
- $1,881,132 per Acre
153 Northside Dr, Bennington, VT 05201

Level, .53-acre lot situated in Bennington’s high-traffic Planned Commercial (PC) District. This site offers a rare opportunity to save significantly on demolition costs and move straight into the design and permitting phase for a new commercial project. This busy corridor lot is located entirely outside of the flood zone, providing a clean slate for development and a more streamlined path for

Lori Hurley Four Corner Properties LLC

153 Northside Dr, Bennington, VT 05201
/12
$865,000
- 12 Beds
- 8 Baths
- 5,568 Sq Ft
1931 Vermont Route 67 E, Shaftsbury, VT 05262

Rare investment opportunity in one of the area’s most desirable neighborhoods! This unique offering includes two historic buildings set on a spacious 1-acre lot, featuring a total of 8 well-maintained units—comprised of (4) two-bedroom apartments and (4) one-bedroom apartments. Each building offers shared covered front porches, perfect for enjoying the charm of this pleasant street setting. The

Julie Glover Mahar McCarthy Real Estate

1931 Vermont Route 67 E, Shaftsbury, VT 05262
/13
$295,000
- 4 Beds
- 2 Baths
- 2,022 Sq Ft
124 S Branch St, Bennington, VT 05201

Don’t miss this two-family gem! Each spacious unit features 2 bedrooms, eat-in kitchen, large living room with hardwood floors and tin ceiling throughout, spacious full bathroom, and in-unit laundry hookups—perfect for comfortable living or strong rental potential. The downstairs unit offers a side porch for sitting and both units get to enjoy a charming covered front porch on a side street. With

Julie Glover Mahar McCarthy Real Estate

124 S Branch St, Bennington, VT 05201
/9
$295,000
- 4 Beds
- 2 Baths
- 2,206 Sq Ft
116 S Branch St Unit 118, Bennington, VT 05201

Well-maintained two-family home offering spacious units, each featuring 2 bedrooms, a cozy kitchen, dining room, living room, full bath, and convenient in-unit washer and dryer hookups. Enjoy relaxing on the inviting covered front porch or the private covered back decks for each unit. Situated on a level half-acre lot, this property also includes off-street parking with a driveway and a 2-car

Julie Glover Mahar McCarthy Real Estate

116 S Branch St Unit 118, Bennington, VT 05201
/23
$90,000
- 2 Beds
- 2 Baths
- 924 Sq Ft
15 Blake Dr, Pownal, VT 05261

Brand-new construction! Excellent opportunity to get affordable housing in Southern Vermont. 2 bedrooms and 2 bathrooms. Full kitchen with dishwasher. Short drive to Bennington, VT or North Adams, MA, 1 hour or so to Albany. Act quick, properties like these sell fast!

Zachary Zupan EXP Realty

15 Blake Dr, Pownal, VT 05261
/12
$234,995
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
240 Church St, Shaftsbury, VT 05262

Ready for its next owner! This charming home offers a great opportunity for anyone looking to put their personal touch on a property with tons of potential. Sitting on an acre-sized lot, there’s plenty of room to expand. Inside, the home needs some TLC—but that’s where the value lies. With the right updates, you can truly bring your vision to life. The layout also provides potential for an in-law

Derek Greene Derek Greene

240 Church St, Shaftsbury, VT 05262
/44
$199,000
- 2 Beds
- 2.5 Baths
- 1,156 Sq Ft
106 Park St Unit 2, Bennington, VT 05201

Freshly updated 2-story townhouse in a convenient downtown Bennington location! This 2BR home features brand new stainless steel appliances, new vinyl plank flooring, and a fresh interior paint palette throughout. The open-concept main level offers a bright kitchen, dining, and living area—perfect for everyday living and entertaining—along with a pantry, half bath, and dedicated laundry room for

Vicki Wilson Maple Leaf Realty

106 Park St Unit 2, Bennington, VT 05201
/17
$159,900
- 2 Beds
- 1.5 Baths
- 852 Sq Ft
432 South St Unit B2, Bennington, VT 05201

Updated and ready to go. This 2 bedroom upstairs condo is perfect for those who don't want to rent, would like to build equity and would like low maintenance. A corner unit with great light and being upstairs means no neighbors overhead. 2 bedrooms, 2 bathrooms (one 3/4 and one half bath). With rents in the area rising this is a great option for most!

Max Squiers KW Vermont - Brenda Jones Real Estate Group

432 South St Unit B2, Bennington, VT 05201
/17
$65,000
- Land
- 5.6 Acres
- $11,607 per Acre
80 Crossover Rd, Bennington, VT 05201

This 5.6-acre lot is ideally situated at the edge of town, offering a peaceful retreat surrounded by nature. Furnace Brook winds through the backside of the property, providing a soothing sound that lulls you to sleep each night. Observe the abundant wildlife as they visit the stream with the Mountain view as the backdrop, this location is perfect for building your Vermont dream home.

Dan Mason Perrott Realty

80 Crossover Rd, Bennington, VT 05201
/8
$65,000
- Land
- 1.24 Acres
- $52,419 per Acre
2041 East Rd, Bennington, VT 05201

Partial cleared 1.2 acre lot where you can listen the stream flow as you watch the abundant wild life.

Dan Mason Perrott Realty

2041 East Rd, Bennington, VT 05201
/34
$450,000
- 3 Beds
- 2.5 Baths
- 2,343 Sq Ft
760 W Mountain Rd, Shaftsbury, VT 05262

Tucked away in a private setting in Shaftsbury, this inviting home sits on 2.12 acres, offering both tranquility and convenience-just a short drive to both Manchester and Bennington. With 2,350 square feet of living space, the home features 3 bedrooms and 2.5 baths, thoughtfully designed for comfort and functionality. Many upgrades were completed in 2006, enhancing both efficiency and livability.

Kelley Mccarthy Mahar McCarthy Real Estate

760 W Mountain Rd, Shaftsbury, VT 05262
/36
$539,000
- 3 Beds
- 2 Baths
- 2,065 Sq Ft
262 Dwyers Camp Rd, Shaftsbury, VT 05262

Well designed and newer home on 10.085 acres in Shaftsbury, VT. Offering 3 bedrooms, including main level primary bedroom and 2 full bathrooms. Cathedral ceiling formal dining room and modern kitchen with dining area and breakfast bar. Large living room with vaulted ceiling and lots of light. Main level laundry and rear mudroom finish the first floor. Upstairs there is a wonderful loft area, 2

Max Squiers KW Vermont - Brenda Jones Real Estate Group

262 Dwyers Camp Rd, Shaftsbury, VT 05262
/15
$165,000
- 2 Beds
- 1 Bath
- 806 Sq Ft
415 County St, Bennington, VT 05201

STOP RENTING and start building equity! Call your lender today to discover the latest programs that could MAKE HOMEOWNERSHIP A REALITY. Owning may be closer than you think. The transformation inside this home is nothing short of spectacular. This move-in-ready, one-floor living bungalow has been thoughtfully designed to maximize every square foot, including a brand-new bathroom and updated

Lori Hurley Four Corner Properties LLC

415 County St, Bennington, VT 05201
/21
$215,000
- 2 Beds
- 1 Bath
- 938 Sq Ft
55 Eden Way Unit 3, Bennington, VT 05201

Move right in to this immaculate 2-bedroom condo in the highly desirable Apple Ridge community! Meticulously maintained and thoughtfully cared for, this home offers effortless one-level living with nothing left to do but unpack. Step inside to discover a freshly painted interior complemented by new flooring and carpeting throughout. The bright and inviting kitchen features beautiful cabinetry and

Angela Bevin Maple Leaf Realty

55 Eden Way Unit 3, Bennington, VT 05201
/51
$1,795,000
- 3 Beds
- 3 Baths
- 5,228 Sq Ft
2167 Myers Rd, Shaftsbury, VT 05262

Welcome to Hidden Ponds Farm - a breathtaking retreat set on 40 sprawling acres where history and refined country living meet in perfect harmony. This extraordinary early 1800s post-and-beam converted barn has been thoughtfully reimagined, preserving its authentic character while seamlessly integrating modern comforts. A magnificent 1,000-foot hand-placed stone wall winds gracefully across the

Kelley Mccarthy Mahar McCarthy Real Estate

2167 Myers Rd, Shaftsbury, VT 05262
/26
$199,000
- 4 Beds
- 2 Baths
- 1,980 Sq Ft
210 Division St, Bennington, VT 05201

Turnkey Two-Unit Investment Opportunity in a Prime Downtown Location!This beautifully renovated duplex is perfect for a first-time investor or owner-occupant looking to build equity while generating income. The property features a two-bedroom unit and a one-bedroom unit, both thoughtfully updated and well maintained.The first-floor unit has been fully renovated, including an updated

Lilli West Maple Leaf Realty

210 Division St, Bennington, VT 05201
/46
$1,550,000
- 5 Beds
- 5 Baths
- 6,129 Sq Ft
1035 Holy Smoke Rd, Shaftsbury, VT 05262

Experience the quintessential Vermont lifestyle in this masterfully renovated (2021) contemporary farmhouse, offering 6,100 sq. ft. of finished living space. Tucked at the end of a breathtaking maple-lined driveway, this 17± acre property offers panoramic mountain views and a private sanctuary for hiking, cross-country skiing, snowshoeing, and snowmobiling right from your door.The heart of

Lori Hurley Four Corner Properties LLC

1035 Holy Smoke Rd, Shaftsbury, VT 05262
/23
$120,000
- 2 Beds
- 1 Bath
- 880 Sq Ft
818 Old Depot Rd, Shaftsbury, VT 05262

Discover quintessential Vermont along this idyllic country road embodying peace and serenity. The property features mature trees and a peaceful, quiet location. Close to Lake Shaftsbury State Park and Lake Paran as well as many hiking trails and ski areas. This would make a perfect weekend getaway, vacation rental, or full-time home. New vinyl siding, a recent metal roof, and newer furnace. Enjoy

Lisa Friedman Great American Dream Realty

818 Old Depot Rd, Shaftsbury, VT 05262
/31
$100,000
- 3 Beds
- 1 Bath
- 1,508 Sq Ft
109 Evergreen Dr, Bennington, VT 05201

House flippers and rehabbers rejoice: an excellent opportunity to put some sweat equity into this charming WWII-era gem at an accessible price. Last house on the right on a quiet dead-end road in a residential area of Bennington, this property boasts a lovely stream running along the northwest of the parcel, a cozy wood stove within, three bedrooms with more space adjoining, enclosed front porch,

Zachary Zupan EXP Realty

109 Evergreen Dr, Bennington, VT 05201
/36
$269,900
- 3 Beds
- 1.5 Baths
- 900 Sq Ft
2092 N Bennington Rd, North Bennington, VT 05257

Waterfront Bungalow style house offering 3 bedrooms and 2 bathrooms. This home has 2 bedrooms upstairs and a pocket half bathroom. downstairs has a master bedroom with a newly remodeled ensuite, kitchen with breakfast table area, 4 seasons living space in the back and a front livingroom with new flooring. The previous owner used the 4 seasons room as a formal dining room since it has

Max Squiers KW Vermont - Brenda Jones Real Estate Group

2092 N Bennington Rd, North Bennington, VT 05257
/58
$1,950,000
- 9 Beds
- 7 Baths
- 6,956 Sq Ft
1086 West Rd, Bennington, VT 05201

Built in 1866, this French Provençal–inspired stone estate is a rare and distinguished offering, blending historic grandeur with pastoral beauty on 94.56 acres just outside historic Bennington, Vermont. Commanding sweeping mountain views, the property delivers exceptional privacy while remaining conveniently close to town amenities. The main residence offers 9 bedrooms and 7 bathrooms,

Kelley Mccarthy Mahar McCarthy Real Estate

1086 West Rd, Bennington, VT 05201
/39
$359,900
- 3 Beds
- 2 Baths
- 1,404 Sq Ft
38 Oak Ridge Ln, Bennington, VT 05201

Convenient one-level living meets modern style and design in this beautifully crafted ranch home, situated on a spacious 1.4-acre lot within a newer, private four-home subdivision. Relax on the impressive 52-foot farmer’s porch—perfect for enjoying cool summer breezes, stunning sunsets, entertaining guests, or simply taking in the expansive yard and thoughtfully designed plantings. Inside the

Matt Waddington Hoffman Real Estate

38 Oak Ridge Ln, Bennington, VT 05201
/8
$35,000
- Land
- 1 Acre
- $35,000 per Acre
0 Barber Pond Rd, Pownal, VT 05261

Tucked into the scenic rural landscape of Pownal, Vermont, this approximate one-acre parcel of raw land offers a blend of natural privacy and water frontage on Barber Pond. Ideal for recreational use or future development, subject to local zoning and permitting. Enjoy the charm of the southern Vermont countryside while remaining within easy reach of nearby towns and outdoor amenities. Known for

Vicki Wilson Maple Leaf Realty

0 Barber Pond Rd, Pownal, VT 05261
/25
$1,425,000
- 3 Beds
- 2.5 Baths
- 2,560 Sq Ft
1058 Granger Hollow Rd, North Bennington, VT 05257

A private Vermont sanctuary set on over 40 acres of meadows, rolling hills, stone walls, and mature forest. This sophisticated modern farmhouse offers rare peace, privacy, and natural beauty, and sweeping seasonal views from every room.Designed to blend seamlessly into the land, the light-filled home features expansive Marvin windows and refined custom finishes throughout. The chef’s kitchen

Andrea Kaplan Four Seasons Sotheby's Int'l Realty

1058 Granger Hollow Rd, North Bennington, VT 05257

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