Is Bennington, VT dog-friendly?

As of early 2026, 92% of users say it's dog friendly

Is a car needed in Bennington, VT?

As of early 2026, 82% of users say car is needed

Are yards well-kept in Bennington, VT?

As of early 2026, 79% of users say yards are well-kept

Is parking easy in Bennington, VT?

As of early 2026, 78% of users say parking is easy

Does Bennington, VT have sidewalks?

As of early 2026, 71% of users say there are sidewalks

Does Bennington, VT show holiday spirit?

As of early 2026, 69% of users say there's holiday spirit

Is there wildlife in Bennington, VT?

As of early 2026, 66% of users say there's wildlife

Is Bennington, VT walkable to restaurants?

As of early 2026, 63% of users say it's walkable to restaurants

Do kids play outside in Bennington, VT?

As of early 2026, 62% of users say kids play outside

Would people walk alone at night in Bennington, VT?

As of early 2026, 59% of users say people would walk alone at night

Are neighbors friendly in Bennington, VT?

As of early 2026, 56% of users say neighbors are friendly

Are the streets well-lit in Bennington, VT?

As of early 2026, 48% of users say streets are well-lit

Is Bennington, VT quiet?

As of early 2026, 44% of users say it's quiet

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

As of early 2026, 38% of users say they plan to stay for at least 5 years

Are there community events in Bennington, VT?

As of early 2026, 33% of users say there are community events

Is Bennington, VT walkable to grocery stores?

As of early 2026, 28% of users say it's walkable to grocery stores

FOR SALE

Listed by Catherine Cairns, Maple Leaf Real Estate, (802) 447-3210

99 Coolidge Avenue
Bennington, VT 05201

3 Beds
1 Bath
1,047 sqft

$219,000

$225,000

$219,000

$225,000

3 Beds

1 Bath

1,047 sqft

We estimate this home will sell faster than 97% nearby.

Local Information

-- mins to

Commute Destination

Last check for updates: about 3 hours ago

Listing courtesy of Catherine Cairns

Maple Leaf Real Estate, (802) 447-3210

Source: PrimeMLS, MLS#5088016

Also Listed on PrimeMLS.

Description

This cute 3-bedroom, 1-bath cape offers comfortable in-town living with a fully fenced yard and recently renovated kitchen and bath. The laundry hookups are on the first floor which adds everyday convenience. Enjoy morning coffee or evening relaxation in the enclosed 3-season porch with outdoor fenced space perfect for pets, play, or gardening. The upstairs bedroom features unique built-ins that add both charm and storage. Conveniently located close to shopping, dining, recreation, and just minutes to the Bennington Recreation Center, this home combines comfort, character, and accessibility in a desirable neighborhood.

We estimate this home will sell faster than 97% nearby.

Home Highlights

Parking

No Info

Outdoor

Porch

A/C

Heating only

HOA

None

Price/Sqft

$209

Listed

37 days ago

Home Details for 99 Coolidge Avenue

Active Status
MLS Status: Active

Interior Features
Interior Details Basement: Bulkhead,Concrete,Unfinished,Basement Stairs,Interior EntryNumber of Rooms: 5
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 1Number of Bathrooms (full): 1
Dimensions and Layout Living Area: 1047 Square Feet
Appliances & Utilities Utilities: CableAppliances: Dishwasher, Dryer, Electric Range, Refrigerator, WasherDishwasherDryerLaundry: 1st Floor LaundryRefrigeratorWasher
Heating & Cooling Heating: Oil,BaseboardNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Oil
Gas & Electric Electric: 100 Amp Service
Windows, Doors, Floors & Walls Flooring: Carpet, Manufactured
Levels, Entrance, & Accessibility Stories: 1.5Levels: One and One HalfAccessibility: 1st Floor Bedroom, 1st Floor Full Bathroom, 1st Floor LaundryFloors: Carpet, Manufactured
View No View

Exterior Features
Exterior Home Features Roof: ShinglePatio / Porch: Enclosed PorchFencing: FullExterior: GardenFoundation: ConcreteGarden
Parking & Garage No GarageParking: Crushed Stone,Paved
Frontage Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: Paved
Water & Sewer Sewer: Public Sewer
Farm & Range Frontage Length: Road frontage: 110
Finished Area Finished Area (above surface): 1047 Square Feet

Days on Market
Days on Market: 37

Property Information
Year Built Year Built: 1930
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Bungalow
Building Construction Materials: Wood Frame, Aluminum SidingNot a New Construction

Price & Status
Price List Price: $219,000Price Per Sqft: $209

Location
Direction & Address City: Bennington
School Information Elementary School District: Southwest VermontJr High / Middle School: Mt. Anthony Union Middle SchJr High / Middle School District: Southwest VermontHigh School: Mt. Anthony Sr. UHSD 14High School District: Southwest Vermont

Agent Information
Listing Agent Listing ID: 5088016

Building
Building Area Building Area: 1659 Square Feet

Lot Information
Lot Area: 8276.4 sqft

Miscellaneous
BasementMls Number: 5088016Above Grade Unfinished Area: 1047Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 462Below Grade Unfinished Area Source: AssessorBelow Grade Unfinished Area Units: Square Feet

Market trends in Bennington

Last updated May 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

7MoM

Price History for 99 Coolidge Avenue

Date	Price	Event	Source
06/12/2026	$219,000	PriceChange	PrimeMLS #5088016
Price Change $6,000 (-3%)
05/10/2026	$225,000	Listed For Sale	PrimeMLS #5088016

08/14/2024	$199,500	Sold	N/A
Recording Date 08/14/2024 Contract Date 08/12/2024 County Transfer Tax N/A Total Transfer Tax $10
05/26/2024	$194,000	Pending	N/A

05/10/2024	$194,000	Listed For Sale	N/A

03/28/2019	$116,500	Sold	PrimeMLS #4736108
Recording Date 03/28/2019 County Transfer Tax N/A Total Transfer Tax N/A
02/11/2019	$119,000	Listed For Sale	Agent Provided

10/04/2018	$49,300	ListingRemoved	Agent Provided

09/08/2018	$49,300	PriceChange	Agent Provided
Price Change $5,400 (-10%)
08/24/2018	$54,700	PriceChange	Agent Provided
Price Change $2,200 (-4%)
08/10/2018	$56,900	PriceChange	Agent Provided
Price Change $4,600 (-7%)
07/25/2018	$61,500	PriceChange	Agent Provided
Price Change $7,400 (-11%)
07/08/2018	$68,900	Listed For Sale	Agent Provided

05/29/2018	$55,000	Sold	N/A
Recording Date 05/29/2018 Contract Date 04/26/2018 County Transfer Tax N/A Total Transfer Tax N/A
12/01/2004	$38,850	Sold	N/A
Recording Date 12/01/2004 Contract Date 11/18/2004 County Transfer Tax N/A Total Transfer Tax $194
08/17/1999	$75,000	Sold	N/A
Recording Date 08/17/1999 Contract Date 08/13/1999 County Transfer Tax N/A Total Transfer Tax N/A

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Property Tax and Assessment

Year	2024
Tax
Assessment	$94,900

Home facts updated by county records

Comparable Sales for 99 Coolidge Avenue

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
116 Morgan Street, Bennington, VT	0.15	Single-Family Home	$206,000	02/20/26	3	2	1,680
20 Rockwood Street, Bennington, VT	0.45	Single-Family Home	$241,000	09/25/25	3	1	1,070
130 Beech Street, Bennington, VT	0.21	Single-Family Home	$217,000	07/10/25	3	2	1,416
107 Coolidge Avenue, Bennington, VT	0.03	Single-Family Home	$225,000	02/18/26	4	2	1,702
100 Webb Street, Bennington, VT	0.33	Single-Family Home	$190,000	09/16/25	3	1	1,416
755 Main Street, Bennington, VT	0.19	Single-Family Home	$130,000	01/28/26	3	1.5	1,485
229 Division Street, Bennington, VT	0.28	Single-Family Home	$150,000	10/31/25	2	2	1,104
1016 County Street, Bennington, VT	0.38	Single-Family Home	$250,000	12/15/25	2	1	900
215 Maple Street, Bennington, VT	0.26	Single-Family Home	$191,500	02/26/26	4	2	1,278
235 Maple Street, Bennington, VT	0.31	Single-Family Home	$141,000	04/01/26	2	1.5	1,060

Nearby homes

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

Skip to last item

SOLD
FEB 18, 2026
$225,000
4 bd
2 ba
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PrimeMLS, Closed
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Skip to first item

Additional Cost

Assigned Schools

These are the assigned schools for 99 Coolidge Avenue.

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 Bennington

At least 58 Trulia users voted on each feature.

92 % Say it's dog friendly
82 % Say car is needed
79 % Say yards are well-kept
78 % Say parking is easy
71 % Say there are sidewalks
69 % Say there's holiday spirit
66 % Say there's wildlife
63 % Say it's walkable to restaurants
62 % Say kids play outside
59 % Say people would walk alone at night
56 % Say neighbors are friendly
48 % Say streets are well-lit
44 % Say it's quiet
38 % Say they plan to stay for at least 5 years
33 % Say there are community events
28 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Jowasieleuski
Resident
6y ago
"I have lived here 20 years and it has gone down hill in this time. No real growth here. Drug use is rampant and jobs are few and far."
3
Flag
Thomayera
Resident
6y ago
"Nothing special about Bennington it may be pretty some times but that’s about it. When it’s pretty we have too many tourists so no win"
1
Flag
Thomayera
Resident
6y ago
"Lived on this part of Gage street for 10 years now. It’s been pretty decent. Had some theft once but other than that was okay"
1
Flag
Kjae_pristine
Resident
6y ago
"I lived in Bennington over 20 years. Bennington has a different type of living. One minute you are in the center of town the next minute you are in the country with nothing but mountains to look at"
0
Flag
Bryonbleau0217
Resident
7y ago
"Minimal traffic,I travel less then 5 miles to work most business are within walking distance.all town roads and no highways are needed if you work and live in Bennington"
0
Flag
s. lowers
Resident
7y ago
"There are other dogs around, all over. So when one barks, they all do. They’re friendly most of the time though, but I guess your dog would pull when walking? I don’t know. I’m sure everything will be great! "
0
Flag
Shennajeann
Resident
7y ago
"Not many people travel up and down the road, and the neighbors are very nice. My neighbors inform me if anybody is on my property or anything "
0
Flag
Tiggacrandall79276
Resident
7y ago
"the Neighborhood is clean and there is no drug activity here it's quite next to the Jr high school. and watch them play baseball or football"
1
Flag
Starlene G.
Resident
8y ago
"people genuinely stay to them self's ,very quiet ,always seem to be rushing around though ,and they stay busy!😊 very clean and nice place to live ,every thing is pretty much accessible!"
0
Flag
renbisson
11y ago
"I was born here. I have lived in CA, and visited several areas of the country. I came here to raise my kids."
0
Flag
mymusic54
13y ago
"Live here - very quiet, close to App hiking trail, new Highway, still super quiet and convenient travel in all directions. Although in town, beautiful countryside within miles."
0
Flag

LGBTQ Local Legal Protections

Catherine Cairns, Maple Leaf Real Estate, (802) 447-3210

Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-06-16 13:44:48 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

99 Coolidge Avenue, Bennington, VT 05201 is a 3 bedroom, 1 bathroom, 1,047 sqft single-family home built in 1930. This property is currently available for sale and was listed by PrimeMLS on May 10, 2026. The MLS # for this home is MLS# 5088016.

99 Coolidge Avenue
Bennington, VT 05201

$219,000

$219,000

Local Information