Bennington, VT Homes

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  /19

  $249,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,070 Sq Ft

  20 Rockwood St, Bennington, VT 05201

  As sweet and tidy as can be, this 3BR/1BA home on a residential street offers one level living just outside of town. Gleaming wood floors in the living room and kitchen; kitchen is efficiently laid out and the dining area opens out to a deck overlooking the landscaped back yard and creates a private retreat for your morning coffee. Full basement has been partially finished with a room perfect

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 441-6757

  20 Rockwood St, Bennington, VT 05201
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  Explore Bennington

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  /14

  $2,275 per month

  • 2 Baths
  • 1,120 Sq Ft
  • Property for Rent

  343 Dewey St, Bennington, VT 05201

  Well-maintained provider office space available for lease, offering approx. 1,120 sq ft. Layout includes a waiting room with half bath, reception area, 2 operatories (or rooms), private office, and an additional half bath. Shared kitchen with the adjacent unit. Staff enjoy a separate entrance and designated parking, distinct from the public entry and lot. Rent includes electric, heat/AC,

  

  Peter West

  BISHOP WEST REAL ESTATE

  (802) 347-1295

  343 Dewey St, Bennington, VT 05201
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  /57

  $190,000 Sold Sep 16, 2025

  • 1,416 Sq Ft
  • $134/SF
  • 75 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1943

  100 Webb St, Bennington, VT 05201

  Enchanted Historic Home with Storybook Charm – A Hidden Gem Near Downtown!Step into a fairytale in this one-of-a-kind, lovingly maintained home — a true magical retreat nestled just minutes from downtown. Owned and cherished by the same family since 1951, this architectural treasure blends old-world artistry with everyday comfort.From the moment you arrive, you're greeted by the

  Lindsey Martin Maple Leaf Realty

  100 Webb St, Bennington, VT 05201
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  /13

  Est $55,770 Not Listed For Sale

  231 Chapel Rd, Bennington, VT 05201

  231 Chapel Rd, Bennington, VT 05201
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  /50

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 2,675 Sq Ft

  55 Monument Ave, Bennington, VT 05201

  Step back in time while enjoying modern comforts in this stunning c. 1787 Colonial home located in the heart of Old Bennington. Brimming with character and charm, this 3BR/3BA residence combines historic elegance with contemporary updates for today’s lifestyle. Inside, you’ll find a brand-new chef’s kitchen designed for culinary enthusiasts, complete with high-end appliances and ample counter

  

  Vicki Wilson

  Maple Leaf Realty

  (802) 849-4742

  55 Monument Ave, Bennington, VT 05201
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  /18

  $1,500 per month

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft
  • Condo for Rent

  432 South St Unit B4, Bennington, VT 05201

  Discover a delightful living experience at 432 South St. Unit B4, a welcoming 2-bedroom, 1.5-bathroom condo nestled in the highly sought-after Nathaniel Court neighborhood of Bennington, VT. Enjoy a range of amenities, including laundry hookups, a dedicated parking space, lawn care, plowing, and garbage taken care of by the association. Please note that pet will not be considered and smoking

  432 South St Unit B4, Bennington, VT 05201
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  /35

  $220,000 Sold Sep 16, 2025

  • 1,554 Sq Ft
  • $142/SF
  • 83 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1930

  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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  /27

  Est $178,042 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,155 Sq Ft

  731 Main St, Bennington, VT 05201

  731 Main St, Bennington, VT 05201
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  /41

  $399,900 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,792 Sq Ft

  882 East Rd, Bennington, VT 05201

  Welcome to 882 East Road! This spacious first-floor ranch, set on 1.97 acres, offers comfort, convenience, and room to grow. Built in 2002, the home features three bedrooms and two and half baths, all thoughtfully designed for easy single level living.The open kitchen provides plenty of working space, a beautiful pantry, and excellent flow into a large living room, perfect for gathering and

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 215-3662

  882 East Rd, Bennington, VT 05201
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  /15

  $1,200 per month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Condo for Rent

  210 Beech St Unit 2, Bennington, VT 05201

  This 1 bedroom unit comes with a massive utility room for tons of extra storage space! The unit includes heat, water/sewer, and garbage in the rental price. Credit and background checks required. Sorry no pets Sorry no smoking. First/Last/Security due at lease signing.

  210 Beech St Unit 2, Bennington, VT 05201
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  /23

  $89,499 Sold Sep 11, 2025

  • 746 Sq Ft
  • $120/SF
  • 90 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2024

  92 Ethans Way, Bennington, VT 05201

  Welcome to 92 Ethans Way, Bennington, VT 05201, where modern comfort meets affordability in Catamount Park! This brand-new Polo model manufactured home offers 2 bedrooms, 1 bathroom, and 746 sq. ft. (14 x 56 ft.) 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

  92 Ethans Way, Bennington, VT 05201
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  /35

  Est $243,721 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft

  312 School St Unit 314, Bennington, VT 05201

  312 School St Unit 314, Bennington, VT 05201
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  /39

  $259,000 Under Contract

  • 3 Beds
  • 1.5 Baths
  • 1,264 Sq Ft

  139 Mckinley St, Bennington, VT 05201

  Welcome to 139 McKinley Street in Bennington! This charming 1920 New Englander blends character and convenience in a great village location. Inside, you'll find a first-floor primary bedroom with laundry and a half bath downstairs, a cozy living room with a beautiful woodstove, and hardwood floors upstairs with easy care laminate throughout the main level.A standout feature is the

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (607) 437-6795

  139 Mckinley St, Bennington, VT 05201
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  /10

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  130 Union St Unit D, Bennington, VT 05201

  This 1-bedroom, 1-bathroom apartment located within the downtown of Bennington offers 700 square feet of living space. The living room features ample natural light and connects directly to the kitchen, which includes essential appliances. The bedroom provides sufficient space for a queen-sized bed and includes plenty of closet space for storage. The bathroom is equipped with standard fixtures and

  130 Union St Unit D, Bennington, VT 05201
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  /54

  $225,000 Sold Sep 10, 2025

  • 2,162 Sq Ft
  • $104/SF
  • 15 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1890

  304 North St Unit 6, Bennington, VT 05201

  Great Investment Opportunity! This well-maintained 3-unit property is a fantastic opportunity for savvy investors. Two of the units are currently rented, providing immediate income potential. Situated just a short stroll from downtown, you'll find charming shops, popular restaurants, and close proximity to the Bennington trail system—perfect for outdoor enthusiasts. Just 1 hour from Albany and

  Thomas Martins Maple Leaf Realty

  304 North St Unit 6, Bennington, VT 05201
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  /34

  Est $456,743 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 1,901 Sq Ft

  647 Fox Hill Rd, Bennington, VT 05201

  647 Fox Hill Rd, Bennington, VT 05201
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  /38

  $595,000 Under Contract

  • 3 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  359 Hickory Hill Rd, Bennington, VT 05201

  Welcome to 359 Hickory Hill! Tucked away at the end of a peaceful cul-de-sac on 2.58 acres, this beautifully updated Center Hall Colonial offers privacy, space, and convivence just minutes from downtown Bennington and major highways to New York City, Boston, and beyond.This three bedroom, two and a half bath home is truly turnkey and move in ready. Inside, you'll find gleaming hardwood and

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 633-6530

  359 Hickory Hill Rd, Bennington, VT 05201
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  /8

  $1,425 per month

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • House for Rent

  104 Abbott St, Bennington, VT 05201

  Please do NOT click the "Request To Apply" button. This will cause a delay in our ability to respond to you. Read below for instructions on how to apply through our website.2br MANUFACTURED HOME for rent!Unit: A-104Apply To: Mountain View CommunityRent: $1425/moBeds/Baths: 2 beds 1.5 bathsSize: 926 square feetPets: Cat & Dog friendly, all animals must be

  104 Abbott St, Bennington, VT 05201
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  /26

  $265,000 Sold Sep 09, 2025

  • 1,576 Sq Ft
  • $168/SF
  • 55 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1930

  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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  /39

  Est $538,926 Not Listed For Sale

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

  557 Fox Hill Rd, Bennington, VT 05201

  557 Fox Hill Rd, Bennington, VT 05201
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  /22

  $650,000

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  203 Northside Dr, Bennington, VT 05201

  Welcome to 203–205 Northside Drive, a truly unique property that combines residential living with commercial potential all in one. Are you looking for the flexibility to live in an apartment while generating income from multiple rental units, or would you prefer to restore the property back into a spacious single-family residence? This property gives you both options. Currently configured with

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 471-3591

  203 Northside Dr, Bennington, VT 05201
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  /24

  $1,100 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  174 S Branch St Unit 174, Bennington, VT 05201

  Second floor two bedroom in quiet neighborhood.- two good sized bedrooms, each with closet- living room- eat in kitchen with new floor- bathroom with shower stall- new windows- newer carpet / newly painted- great quiet neighborhood but still close to downtown- propane heat (tenant pays)- off peak electric hot water (tenant pays)- property owner pays for

  174 S Branch St Unit 174, Bennington, VT 05201
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  /34

  $90,000 Sold Sep 08, 2025

  • 1,366 Sq Ft
  • $66/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  40 Washing Brook Rd, Bennington, VT 05201

  This property offers a secluded retreat with stunning mountain views and the South Stream flowing through it. Bordered by wetlands and woods, it provides a sense of being truly "away from it all."While the house requires significant work, making it an ideal candidate for a cash or rehab loan, it presents a fantastic opportunity for transformation. The living room features a beautiful

  Lilli West Maple Leaf Realty

  40 Washing Brook Rd, Bennington, VT 05201
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  /38

  Est $631,908 Not Listed For Sale

  • 5 Beds
  • 3 Baths
  • 3,266 Sq Ft

  3347 West Rd, Bennington, VT 05201

  3347 West Rd, Bennington, VT 05201
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  /41

  $295,000

  • 5 Beds
  • 2 Baths
  • 2,418 Sq Ft

  226 North St, Bennington, VT 05201

  This beautifully detailed 1880 Victorian in Bennington's residential commercial district offers flexibility and income potential all in one. Currently operating as a successful, fully furnished Airbnb, this 5-bedroom, 2-bath property is ready for its next owner. Whether you're an investor looking for cash flow or a buyer seeking a spacious and charming single family home. The main level

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 327-7149

  226 North St, Bennington, VT 05201
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  /2

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • House for Rent

  165 Benmont Ave, Bennington, VT 05201

  Property Id: 1488761I bed 1 bath small house.The tenants pay their own utilities:heat electric etc…

  165 Benmont Ave, Bennington, VT 05201
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  /28

  $398,350 Sold Sep 04, 2025

  • 1,620 Sq Ft
  • $246/SF
  • 0 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 2025

  315 Chester Knoll Dr, Bennington, VT 05201

  This stunning new construction home offers the perfect blend of modern efficiency and serene natural surroundings. Located in a highly desirable neighborhood, this energy-efficient home is a testament to quality craftsmanship and thoughtful design.Step inside to an open-concept living space flooded with natural light. The main level flows seamlessly to a spacious deck, where you'll enjoy

  Lilli West Maple Leaf Realty

  315 Chester Knoll Dr, Bennington, VT 05201
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  /19

  Est $139,336 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 975 Sq Ft

  1 Division Place, Bennington, VT 05201

  1 Division Place, Bennington, VT 05201
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  /26

  $295,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,640 Sq Ft

  235 Elm St Unit 3, Bennington, VT 05201

  This three-unit building features one unit per floor and is ideally located downtown. Set back from the road, it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. Highlights include a large back deck, a spacious partially fenced yard, and a shared driveway with MLS #5057051. The seller prefers to sell both properties together. Listing agent is related to the seller.

  

  Erica Hale

  Ridgeline Real Estate

  (802) 210-4437

  235 Elm St Unit 3, Bennington, VT 05201
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  /44

  $1,350 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Condo for Rent

  254 Union St Unit B, Bennington, VT 05201

  Second Floor Renovated Two Bedroom Apartment- second floor 2 bedroom, each bedroom has a closet- renovated, new windows and entry door- washer/dryer hookups in kitchen- new stove, new fridge- egress windows and carbon monoxide detectors- includes heat, garbage, plowing and lawncare- tenant pays hot water (electric) and electric - all new!- walk to all amenities,

  254 Union St Unit B, Bennington, VT 05201
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  /37

  $256,250 Sold Sep 03, 2025

  • 1,259 Sq Ft
  • $204/SF
  • 7 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1940

  1236 Morgan St, Bennington, VT 05201

  Charming and solid 1940s Cape with detached 2-car garage. On the outskirts of town with 0.63 acres, this property has a rural vibe, but only 1.2 miles from Main Street... enjoy both the quiet and convenience! Large rear deck overlooks the backyard and is a welcome entryway to the sunny breakfast nook and kitchen. All appliances are staying, including the washer/dryer in the basement. Dining

  Jenifer Prouty Hoffman Hoffman Real Estate

  1236 Morgan St, Bennington, VT 05201
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  /21

  Est $166,025 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  106 Park St Unit 16, Bennington, VT 05201

  106 Park St Unit 16, Bennington, VT 05201
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  /17

  $270,000 Pending

  • 6 Beds
  • 3 Baths
  • 2,900 Sq Ft

  239 - 241 Elm St, Bennington, VT 05201

  Located downtown, this three-unit building it offers a scenic view of Dewey Brook, which flows from the Walloomsac River. The property includes an unfinished space with the potential to add an additional unit, offering great investment upside. Recent updates include a brand-new roof installed this year. Shared driveway with MLS #5057052; seller is seeking to sell both properties together. Listing

  

  Erica Hale

  Ridgeline Real Estate

  (802) 278-6021

  239 - 241 Elm St, Bennington, VT 05201
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  /50

  $1,700 per month

  • 4 Beds
  • 1.5 Baths
  • 1,750 Sq Ft
  • Condo for Rent

  129 Grandview St Unit 129, Bennington, VT 05201

  Very large 1,750 square foot apartment (don't hold me to that exact figure)* 9 foot ceilings on both first floor and second floor. Great space, charming* Has the old world feel to it. Building was erected in the late 1800s* It has a living room, dining room (with bay window) and home office on the first floor* It also has a decent sized kitchen on the first floor with fully

  129 Grandview St Unit 129, Bennington, VT 05201
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  /32

  $170,000 Sold Sep 03, 2025

  • 1,155 Sq Ft
  • $147/SF
  • 66 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1993

  106 Park St Unit 1, Bennington, VT 05201

  Welcome to Unit #1 at Norton Potters, a quaint and quiet townhouse community nestled in a lovely neighborhood setting. This end-unit two-bedroom home is full of character and natural light, offering a peaceful retreat with a deck that overlooks a serene stream.The main level features a spacious living room, dining area, kitchen with a generous pantry, a convenient half bath, and laundry

  Faith Rhodes Maple Leaf Realty

  106 Park St Unit 1, Bennington, VT 05201
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  /19

  Est $169,351 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  106 Park St Unit 10, Bennington, VT 05201

  106 Park St Unit 10, Bennington, VT 05201
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  /33

  $229,900 Under Contract

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft

  5 Center St, Bennington, VT 05201

  Welcome to 5 Center Street in the heart of Bennington! This charming single level home offers 3 bedrooms and 1 full bath across a well designed 1,144 sq. ft. floor plan the perfect size for easy living and energy efficiency. Whether you’re looking to downsize, purchase your first home, or simply enjoy the convenience of one floor living, this home is a wonderful fit.Inside, you’ll find a

  

  Brooke Thomson Drew

  Mahar McCarthy Real Estate

  (802) 553-3433

  5 Center St, Bennington, VT 05201
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  /8

  $1,475 per month

  • 3 Beds
  • 1.5 Baths
  • 980 Sq Ft
  • House for Rent

  86 Bell St, Woodford, VT 05201

  Please do NOT click the "Request To Apply" button. This will cause a delay in our ability to respond to you. Read below for instructions on how to apply through our website.3br MANUFACTURED HOME for rent!Unit: B-086Apply To: Mountain View CommunityRent: $1475/moBeds/Baths: 3 beds 1.5 bathsSize: 980 square feetPets: Cat & Dog friendly, all animals must be

  86 Bell St, Woodford, VT 05201
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  /19

  $225,000 Sold Aug 29, 2025

  • Land
  • 16.68 Acres
  • $13,489 per Acre

  • 34 Days On Market

  1801 S Stream Rd, Bennington, VT 05201

  Welcome to 1801 South Stream Road a picturesque 16.68 acres of timeless Vermont charm property. This beautiful parcel features two classic Vermont red barns full of character and charm, that offer endless potential. With some repairs, they could be ideal for livestock, storage, or workshop space ready to support your vision for country living. A picturesque pond, in need of a little TLC, offers

  Brooke Thomson Drew Mahar McCarthy Real Estate

  1801 S Stream Rd, Bennington, VT 05201
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  /29

  Est $483,463 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 1,752 Sq Ft

  9378 Vt Route 9, Bennington, VT 05201

  9378 Vt Route 9, Bennington, VT 05201

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