Bennington, VT Homes

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  /47

  $399,000

  • 5 Beds
  • 3.5 Baths
  • 3,600 Sq Ft

  46 Duffy Dr, Bennington, VT 05201

  This spacious 5-bedroom, 4-bath Colonial in Bennington's sought-after Maplewood neighborhood offers over 3,600 sq ft of flexible living space, including a finished walk-out in-law suite with full kitchen and private entry. Thoughtfully updated with granite counters, stainless steel appliances, and a smart home system including ADT security, glass break sensors, and a smart thermostat. The vaulted

  Nick Sicard EXP Realty

  46 Duffy Dr, Bennington, VT 05201
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  /38

  $193,800 Sold May 30, 2025

  • 1,008 Sq Ft
  • $192/SF
  • 31 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1915

  134 Imperial Ave, Bennington, VT 05201

  Perched high on Imperial Avenue, this delightful Cape-style home is brimming with character, charm, and endless potential. Gorgeous wood floors and abundant natural light set the tone for a warm, inviting space that’s ready for your personal touch. The main level offers a comfortable flow between the living room, dining area, and kitchen—all boasting sweeping views of downtown Bennington and the

  Angela Bevin Maple Leaf Realty

  134 Imperial Ave, Bennington, VT 05201
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  /32

  Est $294,899 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft

  14 Town Line Rd, Bennington, VT 05201

  14 Town Line Rd, Bennington, VT 05201
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  /37

  $524,900

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  245 Southshire Dr, Bennington, VT 05201

  Nestled at the end of a quiet cul-de-sac in one of Bennington’s most sought-after neighborhoods, this elegant 4-bedroom, 2.5-bath center-hall Colonial offers space, privacy, and timeless charm—all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS).The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal

  Ann Greenwood Alton + Westall Real Estate Agency, LLC

  245 Southshire Dr, Bennington, VT 05201
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  /28

  $213,200 Sold May 30, 2025

  • 1,872 Sq Ft
  • $114/SF
  • 50 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1920

  1004 Main St, Bennington, VT 05201

  Triplex located downtown. Barney brook runs through the property, land includes yard across the brook from the property. Property is located in a flood zone. Flood map shows only one corner of the building in flood zone. There is no indication that the property has flooded in the past. Listing agent is related to the seller.

  Erica Hale Ridgeline Real Estate

  1004 Main St, Bennington, VT 05201
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  /40

  Est $388,706 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,463 Sq Ft

  42 Maple Grove Rd, Bennington, VT 05201

  42 Maple Grove Rd, Bennington, VT 05201
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  /21

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,365 Sq Ft

  339 Chester Knoll Dr, Bennington, VT 05201

  A completely renovated gem in a fantastic location awaits its new owner. This beautifully restored cape-style home in Bennington's desirable Chester Knoll community offers a stunning and worry-free living experience. Adhering to the newest Vermont energy codes, this energy-efficient home boasts an Energy Star propane heating system for optimal comfort and savings.Chester Knoll provides an

  Lori Hurley Four Corner Properties LLC

  339 Chester Knoll Dr, Bennington, VT 05201
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  /22

  $289,000 Sold May 30, 2025

  • 1,833 Sq Ft
  • $158/SF
  • 93 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1920

  214 Prospect St, Bennington, VT 05201

  Beautiful in-town, 3-bedroom, 2-bathroom home is completely turn-key and ready to be your Vermont home! Perfectly situated in a sought-after neighborhood near the hospital, shops, and Bennington's many Main Street parades and festivals, it offers just the ideal blend of convenience and charm. So many recent upgrades and renovations, including a brand-new roof, furnace, significant tree removal

  Lori Hurley Four Corner Properties LLC

  214 Prospect St, Bennington, VT 05201
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  /35

  Est $176,918 Not Listed For Sale

  • 3 Beds

  1213 Gore Rd, Bennington, VT 05201

  1213 Gore Rd, Bennington, VT 05201
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  /26

  $289,900

  • 3 Beds
  • 1.5 Baths
  • 1,576 Sq Ft

  519 South St, Bennington, VT 05201

  Welcome to this beautifully maintained 3-bedroom, 1.25-bath home nestled on a corner lot in Bennington. This inviting property blends classic charm with thoughtful updates, offering comfort and style both inside and out.Step into the spacious kitchen featuring stunning wood cabinetry, granite countertops, and a functional island with a bar sink-perfect for entertaining or everyday living. The

  Kelley Mccarthy Mahar McCarthy Real Estate

  519 South St, Bennington, VT 05201
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  /18

  $155,000 Sold May 23, 2025

  • 819 Sq Ft
  • $189/SF
  • 170 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  432 South St Unit A11, Bennington, VT 05201

  This beautiful two-bedroom, one-and-a-half-bath condominium offers comfortable one-level living in the desirable Nathaniel Court community. With numerous updates, this home is move-in ready and perfect for anyone seeking modern amenities in a serene setting.Enjoy the convenience of being within walking distance to downtown Bennington, with its charming shops, restaurants, and cultural

  Kelley Mccarthy Mahar McCarthy Real Estate

  432 South St Unit A11, Bennington, VT 05201
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  /34

  Est $263,695 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 1,809 Sq Ft

  544 Gore Rd, Bennington, VT 05201

  544 Gore Rd, Bennington, VT 05201
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  /46

  $425,000

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft

  4 Bank St, Bennington, VT 05201

  Across from the 5th Fairway of the Mount Anthony Country Club you’ll find this charming, meticulously maintained 3 bedroom 2 bath home. The spacious open layout, custom kitchen, and expansive deck are warm and inviting. Relax on your front porch and enjoy the scenic mountain vistas of Mount Anthony and the Bennington Monument. Fabulous, convenient location! The home began as a bungalow, the

  Margretta Fischer Wohler Realty Group

  4 Bank St, Bennington, VT 05201
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  /46

  $800,000 Sold May 21, 2025

  • 3,560 Sq Ft
  • $225/SF
  • 34 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1790

  1 Monument Ave, Bennington, VT 05201

  This beautifully restored Old Bennington 4-bedroom Colonial, originally built in 1790 by Captain David Robinson, Jr., grandson of the founder of Bennington, seamlessly blends rich history with modern luxury. Located in the heart of the historic district, the home boasts breathtaking views of the Bennington Battle Monument, Mount Anthony, and the surrounding mountains. Meticulously updated, the

  Kelley Mccarthy Mahar McCarthy Real Estate

  1 Monument Ave, Bennington, VT 05201
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  /40

  Est $607,458 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,706 Sq Ft

  402 Middle Pownal Rd, Bennington, VT 05201

  402 Middle Pownal Rd, Bennington, VT 05201
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  /30

  $349,000

  • 3 Beds
  • 1 Bath
  • 2,032 Sq Ft

  198 Weeks St, Bennington, VT 05201

  Step into this beautiful 1930s classic home, filled with character and endless possibilities. This home offers three bedrooms, one bathroom, and a layout that seamlessly combines classic details with comfortable living spaces. The heart of the home is the large dining area, perfect for hosting gatherings or enjoying quiet family meals. Adjacent, you will find a spacious living room with a

  Margretta Fischer Wohler Realty Group

  198 Weeks St, Bennington, VT 05201
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  /45

  $750,500 Sold May 20, 2025

  • 2,576 Sq Ft
  • $291/SF
  • 27 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2015

  688 Rice Ln, Bennington, VT 05201

  Imagine sitting on your wraparound porch or second story deck looking out over 16 protected acres, your own pond and a view of the White Rocks. Now, imagine going inside to your custom kitchen with cherry cabinets, granite counters and a large butcher block island. The open plan continues throughout the first floor living area with one of two fireplaces, half bath, laundry and a tiled mudroom.

  Cassie Barbeau Mahar McCarthy Real Estate

  688 Rice Ln, Bennington, VT 05201
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  /40

  Est $247,602 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,259 Sq Ft

  1236 Morgan St, Bennington, VT 05201

  1236 Morgan St, Bennington, VT 05201
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  /55

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,664 Sq Ft

  93 Pace Rd, Bennington, VT 05201

  Welcome Home to Your Private Woodland Retreat! ??Tucked away on a serene 2.75-acre wooded lot, this charming 3-bedroom, 1.5-bath home offers a rare blend of comfort, updates, and outdoor magic. With approximately 1,664 sq ft of living space, you’ll have plenty of room to stretch out—and three spacious decks to soak in those treetop views from every angle!? What’s New? Just about everything:All

  Harvey Roettinger RE/MAX North Professionals

  93 Pace Rd, Bennington, VT 05201
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  /34

  $175,000 Sold May 16, 2025

  • 1,056 Sq Ft
  • $166/SF
  • 9 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1993

  106 Park St Unit 8, Bennington, VT 05201

  Bright and sunny with gleaming floors, this second floor flat is absolutely turnkey! 2BR/2BA with dedicated laundry room, open kitchen/living/dining opens onto a covered balcony with room for outdoor seating and taking in the mountain views. Brand new boiler, assigned parking. Walking distance to all things downtown Bennington. Well managed COA offers peace of mind, this is a great

  Vicki Wilson Maple Leaf Realty

  106 Park St Unit 8, Bennington, VT 05201
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  /40

  Est $556,784 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,846 Sq Ft

  88 Southshire Dr, Bennington, VT 05201

  88 Southshire Dr, Bennington, VT 05201
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  /35

  $264,900

  • 2 Beds
  • 2 Baths
  • 1,554 Sq Ft

  115 Jefferson Ave, Bennington, VT 05201

  Located in a charming Bennington neighborhood, this home offers both convenience and comfort, with shopping, schools, the post office, and the hospital just a short distance away. The welcoming three-season front porch is perfect for enjoying your morning coffee or winding down after a long day. Inside, the spacious, eat-in kitchen has brand-new flooring and newer appliances, adding a fresh and

  Kelley Mccarthy Mahar McCarthy Real Estate

  115 Jefferson Ave, Bennington, VT 05201
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  /32

  $300,000 Sold May 15, 2025

  • 2,272 Sq Ft
  • $132/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1970

  17 Tel Rd, Bennington, VT 05201

  Charming 4-Bedroom Ranch with Walk-Out Lower Level!Discover this well-maintained 4-bedroom, 2.5-bath ranch-style home, featuring a spacious walk-out lower level. Enjoy the modern convenience of brand-new appliances, a large deck, and a handy storage shed.A stunning sunroom addition on the lower level boasts cathedral ceilings, skylights, and a sliding glass door leading to the hot tub, creating

  Kelley Mccarthy Mahar McCarthy Real Estate

  17 Tel Rd, Bennington, VT 05201
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  /40

  Est $553,236 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,483 Sq Ft

  377 Southshire Dr, Bennington, VT 05201

  377 Southshire Dr, Bennington, VT 05201
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  /47

  $299,900

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft

  120 Imperial Ave, Bennington, VT 05201

  Nestled in the charming village of Bennington, Vermont, this stately 4-bedroom, 2.5-bath home blends timeless elegance with thoughtful updates. Built in 1895 and set on 0.41 acres, the property offers a rare combination of historic character and modern livability. A large Trex front deck with handicap accessible ramp to the front and kitchen doors welcomes you to the home, where you'll find

  Kelley Mccarthy Mahar McCarthy Real Estate

  120 Imperial Ave, Bennington, VT 05201
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  /17

  $175,000 Sold May 12, 2025

  • 1,056 Sq Ft
  • $166/SF
  • 72 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1900

  220 Division St, Bennington, VT 05201

  Cute, Comfortable and affordable. This 3 bedroom 1 and a half bath home has an in-town location with great walkability. Close to schools convenience stores and a short walk to downtown. Offers large kitchen, formal dining with built-ins, living room, first floor bedroom and half bath. Upstairs 2 more bedrooms, an office space and full bath. Outside you'll find a 3 season porch, 2 car garage/barn

  Max Squiers KW Vermont - Brenda Jones Real Estate Group

  220 Division St, Bennington, VT 05201
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  /40

  Est $539,263 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,336 Sq Ft

  179 Southshire Dr, Bennington, VT 05201

  179 Southshire Dr, Bennington, VT 05201
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  /30

  $295,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,042 Sq Ft

  221 Grandview St, Bennington, VT 05201

  Charming renovated cape with mountain views! Perched high on Grandview Street on a spacious and level lot, this beautifully renovated Cape-style home offers comfort, style, and lovely views of Mount Anthony and beyond. Step inside to a bright and welcoming first floor, where an open-concept layout easily accommodates both living and dining areas, enhanced by large windows that fill the space with

  Angela Bevin Maple Leaf Realty

  221 Grandview St, Bennington, VT 05201
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  /58

  $275,000 Sold May 08, 2025

  • 1,903 Sq Ft
  • $145/SF
  • 49 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1973

  44 Harbour Rd, Bennington, VT 05201

  Comfortable Ranch home with 3 bedrooms and 1 bath. Inside there's lots of room... whether you need a dedicated office to work from home, space to exercise or do projects, whip up a meal or bake goodies, chat around the fireplace, or watch movies by the cozy wood stove. Kitchen is original... you could give it an easy facelift by painting the cabinets and installing new counters and a vinyl

  Jenifer Prouty Hoffman Hoffman Real Estate

  44 Harbour Rd, Bennington, VT 05201
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  /36

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  351 Gore Rd, Bennington, VT 05201

  351 Gore Rd, Bennington, VT 05201
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  /36

  $265,000 Under Contract

  • 2 Beds
  • 1 Bath
  • 1,512 Sq Ft

  82 Oakes St, Bennington, VT 05201

  Charming Two-Bedroom Home in Convenient Bennington LocationWelcome to this inviting two-bedroom, one full bath home offering spacious and versatile living areas. The main floor features a large living room perfect for relaxing or entertaining, a formal dining room, and an eat-in kitchen with a door leading out to a generous deck-ideal for outdoor gatherings.The lower level boasts a large family

  Kelley Mccarthy Mahar McCarthy Real Estate

  82 Oakes St, Bennington, VT 05201
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  /24

  $190,000 Sold May 07, 2025

  • 2,270 Sq Ft
  • $84/SF
  • 6 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1910

  105 County St, Bennington, VT 05201

  3 Unit located downtown. Listing Agent is related to the seller. Unit 2 is considered a 2 bedroom, columned room divider separates room from living room. Delayed showings till 03/09/2025

  Erica Hale Ridgeline Real Estate

  105 County St, Bennington, VT 05201
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  /27

  Est $235,655 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,490 Sq Ft

  43 East St, Bennington, VT 05201

  43 East St, Bennington, VT 05201
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  /46

  $269,000 Under Contract

  • 4 Beds
  • 1 Bath
  • 1,875 Sq Ft

  4 Pine Rd, Bennington, VT 05201

  Motivated seller of this beautifully ranch home on a dead-end road boasts 4 Bedroom. Enjoy the warmth of the sunroom during the day. The living room centered in the middle of the house has plenty of space to spread out and enjoy the pellet stove insert with a brick hearth on those cool nights. Locally crafted Cushman Style cabinet in the dining area with delightful wood cabinets in the kitchen.

  Dan Mason Perrott Realty

  4 Pine Rd, Bennington, VT 05201
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  /33

  $210,000 Sold May 02, 2025

  • 1,215 Sq Ft
  • $173/SF
  • 7 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1989

  852 East Rd, Bennington, VT 05201

  Ideal location just minutes from town, with a country setting and amazing sunset views. This ranch home has nearly 1 and half acres of land with some out buildings. There is a deck overlooking the quiet rolling hill. Open concept kitchen and dining room with glass doors to the deck. Spacious living room with entry closet. 3 bedrooms with closets and a large full bathroom with double vanity. Full

  Lilli West Maple Leaf Realty

  852 East Rd, Bennington, VT 05201
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  /40

  Est $265,670 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,719 Sq Ft

  25 Center St, Bennington, VT 05201

  25 Center St, Bennington, VT 05201
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  /44

  $100,000

  • 5 Beds
  • 1 Bath
  • 1,952 Sq Ft

  273 Union St, Bennington, VT 05201

  This village property has great bones and potential!! First floor includes generously sized kitchen, formal dining room and living room as well as a small office offering the opportunity to expand the full bath to include laundry. The second floor includes four bedrooms including a primary that has a sitting area/dressing room/nursery, whatever suits your needs. Separate barn that while

  Catherine Cairns Maple Leaf Realty

  273 Union St, Bennington, VT 05201
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  /25

  $219,000 Sold Apr 29, 2025

  • 1,213 Sq Ft
  • $181/SF
  • 159 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1860

  1041 N Branch St, Bennington, VT 05201

  Charming 2-3 bedroom, 1-bath home nestled on a peaceful country lot just outside of town. First floor bedroom and bathroom, town water and sewer for convenience and versatility. Property has an oversized 2-car garage with unfinished bonus space upstairs ready to customize. This property features new flooring, updated structural repairs, and the serene beauty of a babbling brook across the

  Lori Hurley Four Corner Properties LLC

  1041 N Branch St, Bennington, VT 05201
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  /40

  Est $280,735 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,313 Sq Ft

  14 Center St, Bennington, VT 05201

  14 Center St, Bennington, VT 05201
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  /31

  $150,000

  • 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

  Zachary Zupan EXP Realty

  109 Evergreen Dr, Bennington, VT 05201

Showing Results 41 - 80, Page 2 of 18