21$179,000
1 bd · 1 ba · 700 sqft
40 Brookside Drive 2, Brattleboro, VT
Angela Sherman · Brattleboro Area Realty
Homes Under $500K in Brattleboro, VT
Hide MapHomes Under $500K in Brattleboro, VT
24 of 49 Listings
21$179,000
1 bd · 1 ba · 700 sqft
40 Brookside Drive 2, Brattleboro, VT
Angela Sherman · Brattleboro Area Realty
30$350,000
3 bd · 2 ba · 1,406 sqft
36 Pine Street, Brattleboro, VT
Christine M Lewis · Brattleboro Area Realty
53$379,000
4 bd · 2 ba · 1,704 sqft
19 Blakeslee Street, Brattleboro, VT
Kristen Ziter Taylor · Brattleboro Area Realty
23$270,000
2 bd · 1 ba · 1,061 sqft
41 Organ Street, Brattleboro, VT
Desiree Stango · Berkley & Veller Greenwood Country
44$319,000
2 bd · 2 ba · 1,883 sqft
59 Highland Street, Brattleboro, VT
Rebecca Seymour · Brattleboro Area Realty
19$289,000
3 bd · 1 ba · 1,056 sqft
145 Belmont Avenue, Brattleboro, VT
Teddy C Kramer · Berkley & Veller Greenwood Country
27$299,000
3 bd · 1 ba · 1,104 sqft
48 Wilsons Woods Road, Brattleboro, VT
Cassandra Ehrlich · BHG Masiello Brattleboro
32$149,900
3 bd · 2 ba · 1,232 sqft
14 Deepwood Park, Brattleboro, VT
Steve Schoppmeyer · BHG Masiello Brattleboro
24$120,000
2 bd · 1 ba · 924 sqft
21 Winding Hill, Brattleboro, VT
Christine M Lewis · Brattleboro Area Realty
21$190,000
2 bd · 1 ba · 930 sqft
39 Brookside Drive 5, Brattleboro, VT
Angela Sherman · Brattleboro Area Realty
17$439,000
2 bd · 2 ba · 1,550 sqft
77 Buttonwood Drive, Brattleboro, VT
Christine M Lewis · Brattleboro Area Realty
19$479,000
2 bd · 2 ba · 1,775 sqft
162 Buttonwood Drive, Brattleboro, VT
Christine M Lewis · Brattleboro Area Realty
26$290,000
5 bd · 2 ba · 2,167 sqft
207 Elliot Street, Brattleboro, VT
Bill Hickok · Berkley & Veller Greenwood Country
50$250,000
2 bd · 2 ba · 1,056 sqft
147 Morningside Commons, Brattleboro, VT
Sally Fegley · BHG Masiello Brattleboro
Price Reduced35$230,000
2 bd · 2 ba · 1,248 sqft
9 Evergreen Lane, Brattleboro, VT
Ayden Hardy · BHG Masiello Keene
Price Reduced35$315,000
2 bd · 1 ba · 640 sqft
203 Fairview Street, Brattleboro, VT
Kristen Ziter Taylor · Brattleboro Area Realty
29$289,000
4 bd · 2 ba · 1,860 sqft
110 Western Avenue, Brattleboro, VT
Wilma Skovinski · Berkley & Veller Greenwood Country
4$182,000
3 bd · 2 ba · 1,114 sqft
23 Williams Street, Brattleboro, VT
Christine M Lewis · Brattleboro Area Realty
24$59,000
2 bd · 1 ba · 744 sqft
9 Village Drive, Brattleboro, VT
Rebecca Seymour · Brattleboro Area Realty
Price Reduced26$230,000
2 bd · 2 ba · 1,248 sqft
11 Evergreen Lane, Brattleboro, VT
Janet Lucier · Barrett & Valley Assoc. Inc
Price Reduced12$285,000
3 bd · 1 ba · 1,050 sqft
455 South Main Street, Brattleboro, VT
Christine M Lewis · Brattleboro Area Realty
Price Reduced35$56,000
2 bd · 1 ba · 552 sqft
22 Valley Road, Brattleboro, VT
Grayson VanHendrick · Flex Realty
Price Reduced37$265,000
3 bd · 3 ba · 1,872 sqft
412 Western Avenue, Brattleboro, VT
Keith Nowak · Four Seasons Sotheby's Int'l Realty
Price Reduced31$299,000
2 bd · 3 ba · 1,607 sqft
136 Morningside Commons, Brattleboro, VT
Desiree Stango · Berkley & Veller Greenwood Country
PrimeMLSSource: HJN community data
August 2026
Selling at 96.9% of asking price
Buyers here are paying below asking. MLS · 19 sales · as of Aug 31, 2026