Is parking easy in Brattleboro, VT?

As of early 2026, 92% of users say parking is easy

Is Brattleboro, VT dog-friendly?

As of early 2026, 91% of users say it's dog friendly

Are yards well-kept in Brattleboro, VT?

As of early 2026, 82% of users say yards are well-kept

Does Brattleboro, VT show holiday spirit?

As of early 2026, 81% of users say there's holiday spirit

Is a car needed in Brattleboro, VT?

As of early 2026, 81% of users say car is needed

Is there wildlife in Brattleboro, VT?

As of early 2026, 80% of users say there's wildlife

Would people walk alone at night in Brattleboro, VT?

As of early 2026, 72% of users say people would walk alone at night

Is Brattleboro, VT walkable to restaurants?

As of early 2026, 66% of users say it's walkable to restaurants

Does Brattleboro, VT have sidewalks?

As of early 2026, 62% of users say there are sidewalks

Are neighbors friendly in Brattleboro, VT?

As of early 2026, 60% of users say neighbors are friendly

Is Brattleboro, VT walkable to grocery stores?

As of early 2026, 58% of users say it's walkable to grocery stores

Do kids play outside in Brattleboro, VT?

As of early 2026, 55% of users say kids play outside

Are the streets well-lit in Brattleboro, VT?

As of early 2026, 50% of users say streets are well-lit

Are there community events in Brattleboro, VT?

As of early 2026, 50% of users say there are community events

Do residents of Brattleboro, VT plan to stay at least 5 years?

As of early 2026, 48% of users say they plan to stay for at least 5 years

Is Brattleboro, VT quiet?

As of early 2026, 38% of users say it's quiet

What is 729 Upper Dummerston Rd estimated to be worth?

Trulia's estimated value for 729 Upper Dummerston Rd in Brattleboro, VT is $309,400 .

What is the price history for 729 Upper Dummerston Rd?

729 Upper Dummerston Rd in Brattleboro, VT last sold for $235,000 in January 2022.

Is Brattleboro a buyer's or seller's market?

Brattleboro is currently a seller's market, based on recent for-sale activity.

What do residents say about Brattleboro?

Residents describe Brattleboro, VT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Brattleboro, VT .

How big is the lot at 729 Upper Dummerston Rd?

The lot at 729 Upper Dummerston Rd in Brattleboro, VT is about 2.3 acres .

Does 729 Upper Dummerston Rd have a garage?

Yes, 729 Upper Dummerston Rd in Brattleboro, VT has a garage.

OFF MARKET

729 Upper Dummerston Rd
Brattleboro, VT 05301

2 Beds
1 Bath
1,186 sqft (on 2.30 acres)

$309,400

Trulia Estimate

as of Aug 19, 2026

$309,400

Trulia Estimate

as of Aug 19, 2026

2 Beds

1 Bath

1,186 sqft

(on 2.30 acres)

Home Value

Trulia Estimate

$309K

Since last month

$2K (+0.6%)

Since last year

$11K (+3.7%)

Since last sale

$73K (+31.1%)

Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +84% in the last 10 years

Month	Estimated value
2026
August 2026	$308K
July 2026	$306K
June 2026	$308K
May 2026	$304K
April 2026	$297K
March 2026	$295K
February 2026	$283K
January 2026	$288K
2025
December 2025	$289K
November 2025	$292K
October 2025	$294K
September 2025	$297K
August 2025	$297K
July 2025	$299K
June 2025	$301K
May 2025	$300K
April 2025	$298K
March 2025	$297K
February 2025	$295K
January 2025	$288K
2024
December 2024	$296K
November 2024	$297K
October 2024	$305K
September 2024	$304K
August 2024	$309K
July 2024	$309K
June 2024	$312K
May 2024	$304K
April 2024	$300K
March 2024	$293K
February 2024	$286K
January 2024	$286K
2023
December 2023	$286K
November 2023	$285K
October 2023	$290K
September 2023	$288K
August 2023	$282K
July 2023	$278K
June 2023	$332K
May 2023	$293K
April 2023	$286K
March 2023	$282K
February 2023	$278K
January 2023	$281K
2022
December 2022	$285K
November 2022	$289K
October 2022	$294K
September 2022	$294K
August 2022	$294K
July 2022	$297K
June 2022	$294K
May 2022	$288K
April 2022	$278K
March 2022	$271K
February 2022	$261K
January 2022	$253K
2021
December 2021	$258K
November 2021	$257K
October 2021	$260K
September 2021	$257K
August 2021	$258K
July 2021	$256K
June 2021	$259K
May 2021	$240K
April 2021	$222K
March 2021	$209K
February 2021	$197K
January 2021	$191K
2020
December 2020	$191K
November 2020	$190K
October 2020	$187K
September 2020	$186K
August 2020	$186K
July 2020	$188K
June 2020	$188K
May 2020	$187K
April 2020	$184K
March 2020	$184K
February 2020	$183K
January 2020	$184K
2019
December 2019	$184K
November 2019	$183K
October 2019	$182K
September 2019	$182K
August 2019	$181K
July 2019	$180K
June 2019	$179K
May 2019	$179K
April 2019	$178K
March 2019	$177K
February 2019	$176K
January 2019	$174K
2018
December 2018	$173K
November 2018	$173K
October 2018	$172K
September 2018	$172K
August 2018	$172K
July 2018	$172K
June 2018	$171K
May 2018	$171K
April 2018	$171K
March 2018	$170K
February 2018	$170K
January 2018	$164K
2017
December 2017	$164K
November 2017	$161K
October 2017	$161K
September 2017	$162K
August 2017	$163K
July 2017	$182K
June 2017	$179K
May 2017	$178K
April 2017	$175K
March 2017	$190K
February 2017	$190K
January 2017	$192K
2016
December 2016	$194K
November 2016	$194K
October 2016	$162K
September 2016	$166K
August 2016	$167K

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
1082 W River Road, Brattleboro, VT	0.82	Single-Family Home	$305,000	09/23/25	3	1	1,222
137 Pleasant Valley Road, Brattleboro, VT	0.68	Single-Family Home	$389,000	05/08/26	1	1	650
672 East Orchard Street, Brattleboro, VT	0.22	Single-Family Home	$470,000	09/26/25	3	3	3,148
131 Pleasant Valley Rd, Brattleboro, VT	0.64	Single-Family Home	$15,000	05/13/26	2	1	792
155 Upper Dummerston Road, Brattleboro, VT	1.06	Single-Family Home	$407,000	11/21/25	3	1.5	1,655
387 Meadow Brook Road, Brattleboro, VT	0.91	Single-Family Home	$439,000	05/13/26	4	2	1,568
23 Meetinghouse Lane, Brattleboro, VT	1.15	Single-Family Home	$495,000	12/29/25	3	2.5	3,415
187 Hillwinds Road, Brattleboro, VT	0.99	Single-Family Home	$476,000	11/20/25	4	3	2,372
1555 W River Road, Dummerston, VT	1.73	Single-Family Home	$243,000	02/26/26	2	1	903
1644 Upper Dummerston Road, Dummerston, VT	1.76	Single-Family Home	$325,000	08/12/26	2	2	1,499

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.

Address	Distance	Price	Bed	Bath	Sqft	Status
672 East Orchard Street, Brattleboro, VT 05301	0.22	$483,700	3	3	3,148	Off Market
94 Brets Road, Brattleboro, VT 05301	0.22	$475,000	3	2.5	2,594	Recently Sold
863 Upper Dummerston Road, Brattleboro, VT 05301	0.24	$582,500	3	2.5	2,112	Off Market
0 East Orchard Street, Brattleboro, VT 05301	0.31	-	-	-	-	Off Market
680 West River Road, Brattleboro, VT 05301	0.37	$145,000	-	-	-	Recently Sold
0 Gibson Road Lot #56, Brattleboro, VT 05301	0.44	-	-	-	-	Off Market
568 West River Road, Brattleboro, VT 05301	0.54	$374,800	2	1.5	1,312	Off Market
395 Hillwinds Road, Brattleboro, VT 05301	0.61	$689,800	4	2.5	2,226	Off Market
1073 Upper Dummerston Road, Brattleboro, VT 05301	0.63	$541,800	3	2	2,456	Off Market
137 Pleasant Valley Road, Brattleboro, VT 05301	0.68	$389,000	1	1	650	Recently Sold
396 East Orchard Street, Brattleboro, VT 05301	0.73	$798,600	4	5	4,300	Off Market
336 Hillwinds Road, Brattleboro, VT 05301	0.72	$762,200	4	3	3,257	Off Market

Local Information

Map ViewExplore the area around 729 Upper Dummerston Rd.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Property Type

Single-Family Home

Year Built

1934

Lot Size

2.3 acres

Living Area

1,186 sqft

Price/Sqft

$261

Parking

Garage

About this House

This single-family home is located at 729 Upper Dummerston Rd, Brattleboro, VT. 729 Upper Dummerston Rd is in Brattleboro, VT and in ZIP code 05301. This property has 2 bedrooms, 1 bathroom and approximately 1,186 sqft of floor space. This property has a lot size of 2.30 acres and was built in 1934.

729 Upper Dummerston Rd, Brattleboro, VT 05301 is a 2 bedroom, 1 bathroom, 1,186 sqft single-family home built in 1934. It last sold for $235,000 on Jan 31, 2022. It is currently off market. The Trulia Estimate is $309,400, with a rent estimate of $2,293/month.

Home Details for 729 Upper Dummerston Rd

Interior Features
Heating & Cooling Heating: GasHeating Fuel: Gas
Interior Details Types of Rooms: Dining Room
Appliances & Utilities Cable Ready
Windows, Doors, Floors & Walls Double Paned Windows
Levels, Entrance, & Accessibility Floors: Carpet, Linoleum Vinyl

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: OtherGardenPorch
Parking & Garage GarageParking: Garage Detached

Property Information
Year Built Year Built: 1934
Property Type / Style Property Type: Single Family Home

Lot Information
Lot Area: 2.30 acres

Price and Tax history

Date	Event	Price
Jan 31, 2022 Source: PrimeMLS #4896758	Sold	$235,000
Feb 20, 2018 Source: PrimeMLS #4609899	Sold	$169,900
Dec 11, 2017 Source: Agent Provided	PendingToActive	$169,900
Dec 11, 2017 Source: Agent Provided	Pending	$169,900
Nov 2, 2017 Source: Agent Provided	PendingToActive	$169,900
Oct 28, 2017 Source: Agent Provided	Pending	$169,900
Aug 18, 2017 Source: Agent Provided	PriceChange	$169,900 Price decreased by 8%
Aug 9, 2017 Source: Agent Provided	PriceChange	$184,900 Price decreased by 3%
Apr 17, 2017 Source: Agent Provided	PriceChange	$189,900 Price decreased by 5%
Nov 23, 2016 Source: Agent Provided	Listed For Sale	$200,000
Dec 8, 2006 Source: N/A	Sold	$184,000

Year	Property tax	Tax assessment
2024	Unavailable	$180,550

Additional Cost

Market trends in Brattleboro

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

Around this home

Academy School
PK-6
Public
418 Students
Windham Southeast Unified Union School District #96
6/10
GreatSchools Rating
Parent Rating Average
Our last public school experience was at a 10/10 on Great Schools. While we had high hopes for that school, they were only able to meet the needs of one type of learner. Here at Academy, they pride themselves on meeting many different learning styles exactly where they are...we are forever grateful.
Other Review
5y ago
3 Reviews

View nearby schools on GreatSchools

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Brattleboro

At least 47 Trulia users voted on each feature.

92 % Say parking is easy
91 % Say it's dog friendly
82 % Say yards are well-kept
81 % Say there's holiday spirit
81 % Say car is needed
80 % Say there's wildlife
72 % Say people would walk alone at night
66 % Say it's walkable to restaurants
62 % Say there are sidewalks
60 % Say neighbors are friendly
58 % Say it's walkable to grocery stores
55 % Say kids play outside
50 % Say streets are well-lit
50 % Say there are community events
48 % Say they plan to stay for at least 5 years
38 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.

Greycella
Resident
2mo ago
"Great neighborhood for learning to ride bikes, trick-or-treating, making friends with other families."
0
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Brenda Nichols
Resident
9mo ago
"Yes! Lots of space for walking and running around with dogs. Quiet countryside with not a lot of traffic."
0
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Kelly Dias
Resident
1y ago
"People watch out for each other, sometimes we go Christmas caroling, we watch each others’ pets; we have a messaging group for neighborhood news"
1
Flag
Kelly Dias
Resident
1y ago
"It’s a great neighborhood to walk dogs. Sometimes bears come through so if it’s bear season you have to be careful. People are respectful and greet each other and we know each others’ dogs. "
0
Flag
Jessica Brown
Resident
2y ago
"I drive through downtown to work and there is some negativity on the streets by way of homelessness and drug abuse/ mental illness. But this neighborhood is still overall a place that I love to live . "
0
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Kelly Dias
Resident
2y ago
"Pet friendly, willing to help out and get to know pets. Lots if grass and forested trails for walking and hiking with dogs. "
0
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Isaac S.
Resident
7y ago
"Great small town in New England-artsy, funky, liberal. Nice amenities for the size of the town. Still some amount of crime-like everywhere these days."
5
Flag
Isaac S.
Resident
7y ago
"Dogs are welcome. Neighbor s are friendly. Houses are well maintained. I feel safe. Walkable neighborhood."
3
Flag
Jcoursem3
Resident
7y ago
"Neighbors are friendly and help each other out. Get together’s are organic and easy because of our close proximity. "
0
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Deanshippee
Resident
7y ago
"A lot of people trust their dogs without a leash. It’s really annoying especially when every dog owner in. Brattleboro should know about our leash law."
7
Flag
Isaac S.
Resident
7y ago
"Car, 5 minutes to work. Few stoplights in town. Friendly drivers except those from Massachusetts and New York. Main Street gets bogged down with traffic but there are several back ways to get around town. Good city for driving in general."
3
Flag
Grace
Resident
8y ago
"I grew up in this neighborhood & am raising my daughter here. I love how bike friendly the neighborhood is and that we can walk both downtown & to the farmer’s market."
11
Flag
rhc3vt
14y ago
"Deteriorating economics, falling home prices, difficult to sell homes, few jobs, really bad schools, more and more poor people in trailer parks. There's not much of a future here."
0
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LGBTQ Local Legal Protections

Frequently asked questions about 729 Upper Dummerston Rd

What is 729 Upper Dummerston Rd estimated to be worth?
Trulia's estimated value for 729 Upper Dummerston Rd in Brattleboro, VT is $309,400.
What is the price history for 729 Upper Dummerston Rd?
729 Upper Dummerston Rd in Brattleboro, VT last sold for $235,000 in January 2022.
Is Brattleboro a buyer's or seller's market?
Brattleboro is currently a seller's market, based on recent for-sale activity.
What do residents say about Brattleboro?
Residents describe Brattleboro, VT as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Brattleboro, VT.
How big is the lot at 729 Upper Dummerston Rd?
The lot at 729 Upper Dummerston Rd in Brattleboro, VT is about 2.3 acres.
Does 729 Upper Dummerston Rd have a garage?
Yes, 729 Upper Dummerston Rd in Brattleboro, VT has a garage.