
Meet Cummings & Co

Lisa Kelley
price range
sales last 12 months

Jeffrey Sheehan
price range
sales last 12 months

Jessica Citera
price range
sales last 12 months

Chris Cummings
price range
sales last 12 months

Dan McKenna
price range
sales last 12 months

Peggy O'Neill
price range
sales last 12 months
Get to know Cummings & Co
Licensed Broker/Owner
Forging Relationships Throughout Vermont
Alison has intimate knowledge of our local area due to the fact that she has lived here since she was a small child. Not a Vermonter (just because your cat has kittens in the oven doesn’t make them muffins), Ali considers herself almost a Native. She attended Flood Brook Elementary, Vermont Academy, and the University of Vermont. Alison spent much of her youth ski racing, in both alpine and cross-cou...
Team sales and listings (606)
This map and property list shows the most recent 100 sales and 100 listings
Sold (584)
- $573,500
- 3 bd
- 4 ba
- 2,250 sqft
883 Smead Road, Wardsboro, VT 05355Sold 3 days agoBuyer
- $437,500
- 4 bd
- 2 ba
- 1,568 sqft
8 Okemo Heights, Lot, VT 05149Sold 16 days agoBuyer
- $107,500
- -- bd
- -- ba
- -- sqft
111 Gib Lockerby Road, Grafton, VT 05146Sold 17 days agoSeller
- $313,265
- 5 bd
- 2 ba
- 1,944 sqft
2015 Vermont Route 30, Townshend, VT 05353Sold 18 days agoBuyer
- $125,000
- -- bd
- -- ba
- -- sqft
0 Stratton View Road #62-63, Bondville, VT 05340Sold 24 days agoBuyer
For sale (22)
- $350,000
- 4 bd
- 2 ba
- 2,022 sqft
73 Robinson Lane, West Wardsboro, VT 05360House for SaleWood-burning fireplace
- $599,000
- 3 bd
- 3 ba
- 2,700 sqft
60 Bowlsville S Road, East Wallingford, VT 05742House for SaleSoaring cathedral ceilings
- $619,000
- 4 bd
- 4 ba
- 3,716 sqft
1918 VT RTE 155, East Wallingford, VT 05742House for SaleLarge deck
- $349,000
- 4 bd
- 3 ba
- 3,332 sqft
397 River Street, Chester, VT 05143House for SaleWood stove
- $319,000
- 3 bd
- 2 ba
- 1,539 sqft
380 South Main Street, Brattleboro, VT 05301House for SaleBright sun-filled dining porch
Team reviews (54)
Reviews represent all team members.
- 5.0
- 3/2/2026
- • Andrew Hasselbring
Bought a Single Family home in 2025 in Chester, VT.
Review for: Alison CummingsAlison Cummings is a terrific realtor. She helped us successfully search from Texas for our dream home in Vermont. We looked at several counties in Vermont and Ali knew...Alison Cummings is a terrific realtor. She helped us successfully search from Texas for our dream home in Vermont. We looked at ...5.0- 2/26/2026
- • bpv6v
Bought a Single Family home in 2023 in Woodstock, VT.
Review for: Alison CummingsAli Cummings was willing to strap on her mud boots and guide us to somewhat remote parcels of raw Vermont land when no other real estate agents responded to our inquiries...Ali Cummings was willing to strap on her mud boots and guide us to somewhat remote parcels of raw Vermont land when no other real ... - Alison was excellent in all areas helping us to buy and sell a house in Vermont. She was helpful and incredibly knowledgable. We would definitely use her services again!Alison was excellent in all areas helping us to buy and sell a house in Vermont. She was helpful and incredibly knowledgable. We w...I have known Alison and Chris Cummings for 10 years, having developed a professional relationship when I decided to sell my home in Vermont. They worked incredibly hard w...I have known Alison and Chris Cummings for 10 years, having developed a professional relationship when I decided to sell my home i...
- 5.0
- 2/24/2026
- • elizabet albert
Bought a Vacant Land home in 2020 in Andover, VT.
Review for: Alison CummingsAlison is a very knowledgeable and super personable realtor. She listens carefully and was able to answer my many questions. She has extensive knowledge of the region and...Alison is a very knowledgeable and super personable realtor. She listens carefully and was able to answer my many questions. She h...Ali was great to work with! She was attentive, honest, engaged, patient, creative, thoughtful, and the consummate teammate for the process of buying a house. She was ge...Ali was great to work with! She was attentive, honest, engaged, patient, creative, thoughtful, and the consummate teammate for th... - 5.0
- 2/12/2025
- • jonathan7987
Bought a Multiple Occupancy home in 2025 in Rutland city, Rutland city, VT.
Review for: Lisa KelleyExcellent job negotiating a fair, quick deal on a multi family purchase. Highly recommend! In our area is hard to find someone who has both great local knowledge as well...Excellent job negotiating a fair, quick deal on a multi family purchase. Highly recommend! In our area is hard to find someone wh...Lisa was very responsive, supportive, and most importantly patient with us through our home buying journey. Her advice and guidance through the process made us feel comfo...Lisa was very responsive, supportive, and most importantly patient with us through our home buying journey. Her advice and guidanc... - 5.0
- 10/19/2024
- • lisa196768
Bought a Single Family home in 2024 in Chester, VT.
Review for: Lisa KelleyShe worked w/for almost a yr! From the time we started to look. when we still lived in MA she diligently called, email & produced videos for us to review. She met up w/u...She worked w/for almost a yr! From the time we started to look. when we still lived in MA she diligently called, email & produced...5.0- 8/4/2024
- • robert eppsteiner
Bought a Single Family home in 2024 in Wardsboro, VT.
Review for: Jeffrey SheehanOur experience with Jeff was excellent from start to finish. He has a lot of expertise and his assessment of properties was really helpful in our decision making. He made...Our experience with Jeff was excellent from start to finish. He has a lot of expertise and his assessment of properties was really...




