Homes for Sale in 05201

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  /38

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,829 Sq Ft

  89 Merson St, Woodford, VT 05201

  Welcome to 89 Merson Street! This charming Cape style home offers 3 bedrooms, 1 full bathroom and a half bathroom, and nearly an acre of land on a quiet in town street. Inside, you’ll find beautifully refinished hardwood floors, an updated kitchen, a spacious family room with a fireplace, and a new Weil-McLain boiler installed in February 2026.What truly sets this property apart is its

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 523-3711

  89 Merson St, Woodford, VT 05201
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  /33

  $279,000

  $20K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  8 West St, Bennington, VT 05201

  Nestled in the heart of the charming North Bennington community, this lovingly maintained 3 bedroom, 1.5 bath home is ready for its next chapter. Recently refreshed with newly painted interiors, rejuvenated floors, updated electrical, a recently repointed foundation, and repointed chimney, this home blends classic character with thoughtful updates throughout.Enjoy the convenience of first

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 551-3900

  8 West St, Bennington, VT 05201
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  /41

  $550,000

  • 5 Beds
  • 2 Baths
  • 1,974 Sq Ft

  971 S Stream Rd, Bennington, VT 05201

  Have you been searching for the Vermont farmhouse that truly feels like home? The one with the land, the barns, the mountain views, the wraparound driveway, the screened in porch, and the beautiful front porch where you can sit and enjoy quiet mornings and peaceful evenings? This is that home.Situated on over 17 acres, this property offers not one but two barns, established fenced pastures,

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 566-5234

  971 S Stream Rd, Bennington, VT 05201
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  /53

  $200,000

  • Land
  • 58.1 Acres
  • $3,442 per Acre

  1073 Chapel Rd, Bennington, VT 05201

  Unlock the potential of this spectacular 58.1 +/- acre woodland property in historic Bennington. The groundwork for your future home or getaway is already laid with a State-approved wastewater permit in place for a three-bedroom single-family residence, allowing you the flexibility to design your build. Further simplifying your plans, the property offers the rare advantage of connecting to the

  Curtis Trousdale Preferred Properties

  1073 Chapel Rd, Bennington, VT 05201
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  /27

  $209,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,075 Sq Ft

  1083 Main St, Bennington, VT 05201

  Charming two-bedroom, one-bath bungalow located just outside of Bennington. This inviting home features beautiful hardwood floors throughout, a spacious kitchen with a dedicated dining area, a comfortable living room, and a versatile office or study perfect for a variety of needs. Enjoy the convenience of main-level laundry and relax in the cozy three-season porch. Additional highlights include a

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  1083 Main St, Bennington, VT 05201
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  /29

  $250,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  103 Jennings Brook Dr, Bennington, VT 05201

  Located in the desirable Jennings Brook community, this condominium offers a wonderful opportunity to add your own personal touches while enjoying a convenient Bennington location. The spacious living room features a cozy fireplace, beautiful built-ins, and abundant natural light, while the large dining room provides an ideal setting for gatherings and entertaining. The foyer is currently used as

  Kelley Mccarthy Mahar McCarthy Real Estate

  103 Jennings Brook Dr, Bennington, VT 05201
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  /14

  $237,700

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  117 Putnam St, Bennington, VT 05201

  This beautifully renovated 2-unit home by JDN Properties offers exceptional flexibility for buyers, allowing for a variety of living arrangements to suit your needs. Whether you choose to enjoy it as a spacious two-story single family residence with a luxurious upstairs primary suite and kitchenette, use it as an owner-occupied property with a rental unit to help offset your mortgage, or maximize

  Dan Mason Perrott Realty

  117 Putnam St, Bennington, VT 05201
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  /31

  $90,000

  $35K PRICE DROP

  • 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
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  /6

  $199,900

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  2 Hamlin Ave, Bennington, VT 05201

  2-Unit Multi-Family with Professional-Grade Workshop!Versatile property with high-yield setup, perfect for a contractor, carpenter, or owner-occupant. The standout feature is a professional-grade workshop fully optimized for year-round productivity with radiant heat, bright lighting, and the added convenience of an existing sink and toilet. Whether utilized for a trade, automotive enthusiast,

  Lori Hurley Four Corner Properties LLC

  2 Hamlin Ave, Bennington, VT 05201
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  /32

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,443 Sq Ft

  21 Pageant St, Bennington, VT 05201

  This well-maintained ranch-style home offers the convenience of one-level living with 3 bedrooms plus a spacious primary suite. Set on a large lot, the property features two decks, providing plenty of outdoor space for entertaining, relaxing, or enjoying the backyard. An easy walk to the local golf course adds to the appeal of this desirable location. The updated kitchen boasts beautiful granite

  Kelley Mccarthy Mahar McCarthy Real Estate

  21 Pageant St, Bennington, VT 05201
• 

  

  /11

  $179,900

  • 2 Beds
  • 1 Bath
  • 848 Sq Ft

  302 U S 7 S, Woodford, VT 05201

  Over 3 acres, a brook and lots of woods for walking. Room for a terraced garden, tons of parking and minutes to Bennington! This 2 bedroom ranch style home has a huge eat in kitchen and a lovely big living room with lots of windows. There is a bonus sun room with laundry. Owners are using an attached shed as a chicken coop! Sweet find at this affordable price!

  Christine Lewis Brattleboro Area Realty

  302 U S 7 S, Woodford, VT 05201
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  /52

  $230,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  113 Main St, Bennington, VT 05201

  Charming downtown family home with modern upgrades and timeless appeal. This beautifully updated 3-bedroom home is perfectly situated on a corner lot in the heart of downtown. Thoughtfully designed for both comfort and convenience, the home features a recently added first-floor primary bedroom and a new mudroom entry.Step inside to find gleaming newly upgraded flooring, a warm and inviting

  Lindsey Martin Maple Leaf Real Estate

  113 Main St, Bennington, VT 05201
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  /53

  $599,000

  $96K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,715 Sq Ft

  58 Mount Anthony Rd, Bennington, VT 05201

  Welcome to one of the most coveted locations in Bennington, Vermont known to locals as the West End. Steeped in history, this remarkable property was built c.1928 with ties to the Colgate Estate located on Mount Anthony. A stones throw away is the original Fillmore Farm, primarily known for its sheep. In 1929, the farm began production of milk and then built its large dairy plant in 1939. It can

  Monique Geannelis Mahar McCarthy Real Estate

  58 Mount Anthony Rd, Bennington, VT 05201
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  /59

  $419,000

  $10K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,119 Sq Ft

  131 Pine Cir, Bennington, VT 05201

  A must-see! Nestled in a quiet neighborhood just minutes from downtown dining and shopping, this beautifully maintained home offers comfort, flexibility, and thoughtful upgrades throughout. Completely renovated approximately 10 years ago, the home features a well-designed gourmet kitchen with granite countertops, a copper sink, soft-close cabinetry, and a custom built-in wine rack. French doors

  Vicki Wilson Maple Leaf Real Estate

  131 Pine Cir, Bennington, VT 05201
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  /43

  $579,000

  • 3 Beds
  • 2 Baths
  • 2,501 Sq Ft

  856 Matteson Rd, North Bennington, VT 05257

  Nestled on 5 private acres, this custom-built log home offers the perfect blend of rustic charm and refined comfort. Surrounded by beautifully curated gardens, mature apple trees, lilacs, maples, plum trees, oaks, and stone walls, the setting is both tranquil and picturesque—yet just minutes from town conveniences. There is even a targeting golf green! Inside, the home showcases a stunning great

  Faith Rhodes Maple Leaf Real Estate

  856 Matteson Rd, North Bennington, VT 05257
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  /27

  $189,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,485 Sq Ft

  432 South St Unit D2, Bennington, VT 05201

  Welcome to easy living at Nathaniel Court! This spacious and light-filled tri-level condo offers the perfect blend of comfort, flexibility, and convenience in the heart of Bennington. Privately situated in a standalone building at the edge of the development, this well-maintained 3BR, 3BA home features generous living spaces, abundant natural light, and dedicated parking. A rare opportunity to

  Abi Gregorio

  432 South St Unit D2, Bennington, VT 05201
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  /7

  $997,000

  • Land
  • 23,086 Sq Ft
  • $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
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  /9

  $279,000

  $16K PRICE DROP

  • 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
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  /13

  $279,000

  $16K PRICE DROP

  • 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
• 

  

  /15

  $389,000

  New Construction

  • 4 Beds
  • 2 Baths
  • 2,516 Sq Ft

  319 Chester Knoll Dr, Bennington, VT 05201

  Build Your Dream Home—Without Starting From Scratch Now is your chance to own a brand-new home and still make it your own.This beautifully designed new construction home is currently underway and offers buyers the exciting opportunity to select their own finishing touches and create a space that reflects their style and vision.Featuring 4 bedrooms and 2 full bathrooms, this thoughtfully

  Lilli West Maple Leaf Real Estate

  319 Chester Knoll Dr, Bennington, VT 05201
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  /52

  $289,000

  • 3 Beds
  • 1.5 Baths
  • 1,411 Sq Ft

  262 Union St, Bennington, VT 05201

  Just a short walk to downtown shopping and dining you can move right into this well-maintained and thoughtfully updated 3-bedroom, 2-bath home offering comfortable living spaces, modern conveniences, and plenty of room to spread out both inside and out.The heart of the home is the spacious, updated kitchen featuring a center island, abundant counter top space, and generous cabinetry, and even

  William Paquin Maple Leaf Real Estate

  262 Union St, Bennington, VT 05201
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  /24

  $215,000

  $20K PRICE DROP

  • 1,300 Sq Ft

  340 Pleasant St, Bennington, VT 05201

  Downtown Bennington duplex offering an excellent opportunity for first-time homebuyers, owner-occupants, or investors. The first-floor unit has been completely renovated with a new kitchen, updated bathroom, and new flooring throughout. Recent improvements include a repointed foundation, fully completed siding, a new roof, and a gravel driveway. Live in one unit and help offset your mortgage with

  Melissa Nebelski Real Broker LLC

  340 Pleasant St, Bennington, VT 05201
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  /45

  $275,000

  $20K PRICE DROP

  • 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
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  /7

  $145,000

  $30K PRICE DROP

  • Land
  • 15.49 Acres
  • $9,361 per Acre

  00 Silk Rd, Bennington, VT 05201

  Fifteen and a half level, mowed acres, suitable for a home build, agriculture, or a small subdivision. Passing over the iconic Silk Road Covered Bridge crossing the Walloomsac River, on the right you'll find this flat, cleared parcel ready for farming or development. With over 500 feet of road frontage, plenty of acreage, and the beautiful river across the street, the possibilities here are

  David White OwnerEntry.com

  00 Silk Rd, Bennington, VT 05201
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  /55

  $225,000

  • 4 Beds
  • 2 Baths
  • 1,518 Sq Ft

  142 Pine Cir, Bennington, VT 05201

  Opportunity is knocking... answer the door! This home in a sought-after neighborhood on an almost half acre lot is the investment you've been looking for. Close to downtown shopping and dining, as well as the award-winning Southwestern Vermont Medical Center. Features include an attached two car garage, wood floors, mini-split in living room, fireplace, wood floors, dining room, primary bedroom

  Justine Curry Maple Leaf Real Estate

  142 Pine Cir, Bennington, VT 05201
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  /25

  $950,000

  $300K PRICE DROP

  • 8,888 Sq Ft

  124 Elm St, Bennington, VT 05201

  An exceptional opportunity to own a prominent historic Victorian property in the heart of Bennington, offered as a residential or multifamily real estate asset only. Built in 1887 by renowned architect William C. Bull, this meticulously restored property offers flexible residential and mixed-use potential within the Village of Bennington, subject to applicable municipal approvals. The main

  Marek Kovac TPW Real Estate

  124 Elm St, Bennington, VT 05201
• 

  /2

  $2,190,000

  • Land
  • 1.16 Acres
  • $1,887,931 per Acre

  301 Northside Dr, Bennington, VT 05201

  Prime commercial investment opportunity at 301 Northside Drive, Bennington. This 1.16-acre corner lot offers exceptional visibility on a heavily traveled road, making it well-suited for high-exposure commercial uses. Commercial zoning allows for a range of development or redevelopment options. Strategically located near major highways, providing strong regional access and long-term demand

  Paul Carroccio TPW Real Estate

  301 Northside Dr, Bennington, VT 05201
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  /42

  $279,000

  • 2 Beds
  • 1 Bath
  • 2,142 Sq Ft

  32 Albe Dr, Bennington, VT 05201

  MOVE RIGHT IN AND MAKE YOURSELF AT HOME This beautifully maintained residence is perfect for those looking for the convenience of first floor living. Featuring tastefully painted rooms, bamboo flooring and modern appliances.The kitchen includes a dedicated eating area for family dining while the living room offers a warm and cozy gathering space. Both bedrooms are generously sized with large

  Beatrice O'Connell Maple Leaf Real Estate

  32 Albe Dr, Bennington, VT 05201
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  /60

  $695,000

  • 4 Beds
  • 2 Baths
  • 1,614 Sq Ft

  515 Quarry Rd, Bennington, VT 05201

  Peaceful, private, and completely surrounded by nature, this beautifully renovated contemporary home offers the perfect mountain retreat nestled on 14.7 acres on the side of Mt. Anthony with seasonal views and unmatched tranquility. Enjoy direct access to miles of hiking trails, abundant wildlife, and the rare protection of no future development permitted above this elevation, preserving the

  Vicki Wilson Maple Leaf Real Estate

  515 Quarry Rd, Bennington, VT 05201
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  /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. Perk test were positive for a inground leaching system, results available.

  Dan Mason Perrott Realty

  2041 East Rd, Bennington, VT 05201
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  /33

  $295,000

  • 4 Beds
  • 2 Baths
  • 1,792 Sq Ft

  254 Union St, Bennington, VT 05201

  Welcome to this well-maintained, solid income-producing two-family home located in the heart of town—just steps from shops, dining, and downtown events. Perfect for owner-occupants or savvy investors, this property combines classic charm with modern efficiency and low operating costs. Each two-bedroom unit features spacious, light-filled living areas, eat-in kitchen and comfortable bedrooms.

  Cassie Barbeau Mahar McCarthy Real Estate

  254 Union St, Bennington, VT 05201
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  /29

  $399,000

  $16K PRICE DROP

  • 5,208 Sq Ft

  126 Washington Ave, Bennington, VT 05201

  Circa 1913 carriage barn converted into a mixed-use property in the heart of downtown Bennington. This distinctive 5,208± sq. ft. building combines residential and commercial opportunity, featuring three apartments and a ground-floor retail space. Original architectural details evoke the property’s historic character, while modern updates support comfortable living and reliable income potential.

  Vicki Wilson Maple Leaf Real Estate

  126 Washington Ave, Bennington, VT 05201
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  /20

  $499,000

  • 6 Beds
  • 6 Baths
  • 9,000 Sq Ft

  425 Main St, Bennington, VT 05201

  15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R

  Chris Long BHG Masiello Brattleboro

  425 Main St, Bennington, VT 05201
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  /14

  $125,000

  • 3 Beds
  • 1 Bath
  • 768 Sq Ft

  347 Hickory Rd, Bennington, VT 05201

  Your wait is over—an exceptional opportunity to own in the highly sought-after Woodford Lake Estates! This unique property offers direct access to the beauty of the surrounding Green Mountain National Forest and is ideally located near VAST snowmobile trails, making it a year-round haven for outdoor enthusiasts. Enjoy cross-country skiing just minutes away at Prospect Mountain, along with beach

  Faith Rhodes Maple Leaf Real Estate

  347 Hickory Rd, Bennington, VT 05201
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  /8

  $59,000

  • Land
  • 12,632 Sq Ft
  • $203,448 per Acre

  420 Burgess Rd, Bennington, VT 05201

  Level building lot with town sewer and water at the edge of town.Possible owner financing.

  Dan Mason Perrott Realty

  420 Burgess Rd, Bennington, VT 05201
• 

  

  /3

  $74,900

  • Land
  • 2.25 Acres
  • $33,289 per Acre

  0 Brambley Ln, Bennington, VT 05201

  Expansive 2.25-acre level lot situated on a quiet, private dead-end street. This is an amazing opportunity to build a dream home, a weekend retreat, or a spec house for investment. The property features 306 feet of road frontage, has been perc tested, and includes septic plans for a three-bedroom system. Located on the outskirt of town, but still close proximity to historic downtown Bennington

  Matt Waddington Hoffman Real Estate

  0 Brambley Ln, Bennington, VT 05201
• 

  

  /3

  $475,000

  • Land
  • 12.82 Acres
  • $37,051 per Acre

  22 Morse Rd, Bennington, VT 05201

  Positioned in the heart of Bennington’s commercial corridor on 12.82 open acres, 22 Morse Road present a prime development opportunity. Offering excellent visibility and accessibility along one of the area’s primary commercial arteries, the property is ideally situated for a variety of commercial, retail, service, mixed-use, or redevelopment possibilities. The location provides convenient access

  Paul Carroccio TPW Real Estate

  22 Morse Rd, 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
• 

  

  /16

  $96,406

  New Construction

  • 2 Beds
  • 2 Baths
  • 777 Sq Ft

  32 Cassie Ln, Bennington, VT 05201

  Welcome to 32 Cassie Lane, Bennington, VT, where modern comfort meets affordability in Catamount Park! This brand-new Redman NWS F25206-58 model manufactured home offers 2 bedrooms, 2 bathrooms, and 777 sq. ft. (13'4"x58) of thoughtfully designed living space. Step inside to an open-concept layout with stylish finishes, a bright living area, and a well-appointed kitchen. The home features

  Kate Barry EXP Realty

  32 Cassie Ln, Bennington, VT 05201
• 

  

  /26

  $359,900

  $10K PRICE DROP

  • 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

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