Is a car needed in Middlebury, VT?

As of early 2026, 89% of users say car is needed

Would people walk alone at night in Middlebury, VT?

As of early 2026, 76% of users say people would walk alone at night

Are yards well-kept in Middlebury, VT?

As of early 2026, 72% of users say yards are well-kept

Is Middlebury, VT dog-friendly?

As of early 2026, 71% of users say it's dog friendly

Is there wildlife in Middlebury, VT?

As of early 2026, 64% of users say there's wildlife

Is parking easy in Middlebury, VT?

As of early 2026, 61% of users say parking is easy

Is Middlebury, VT walkable to restaurants?

As of early 2026, 60% of users say it's walkable to restaurants

Does Middlebury, VT show holiday spirit?

As of early 2026, 59% of users say there's holiday spirit

Are neighbors friendly in Middlebury, VT?

As of early 2026, 54% of users say neighbors are friendly

Is Middlebury, VT quiet?

As of early 2026, 52% of users say it's quiet

Is Middlebury, VT walkable to grocery stores?

As of early 2026, 50% of users say it's walkable to grocery stores

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

As of early 2026, 50% of users say they plan to stay for at least 5 years

Does Middlebury, VT have sidewalks?

As of early 2026, 48% of users say there are sidewalks

Are there community events in Middlebury, VT?

As of early 2026, 45% of users say there are community events

Do kids play outside in Middlebury, VT?

As of early 2026, 39% of users say kids play outside

Are the streets well-lit in Middlebury, VT?

As of early 2026, 27% of users say streets are well-lit

What is 2 Overbrook Dr estimated to be worth?

Trulia's estimated value for 2 Overbrook Dr in Middlebury, VT is $315,300 .

What is the price history for 2 Overbrook Dr?

2 Overbrook Dr in Middlebury, VT last sold for $235,000 in February 2021.

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

Middlebury is currently a balanced market, based on recent for-sale activity.

What do residents say about Middlebury?

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

Does 2 Overbrook Dr have laundry facilities?

Yes, 2 Overbrook Dr in Middlebury, VT has in-unit laundry.

OFF MARKET

$315,300

Trulia Estimate

2 Beds
1 Bath
1,008 sqft

2 Overbrook Dr, Middlebury, VT 05753

Est. Refi. Payment $2,140/mo*

Refinance Your Home

Currently Off Market - Sold Feb 12, 2021 for $235,000

Home Value

Trulia Estimate

$315K

Since last month

$800 (-0.3%)

Since last year

$6K (-1.8%)

Since last sale

$80K (+33.9%)

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 +61% in the last 10 years

Month	Estimated value
2026
August 2026	$315K
August 2026	$314K
July 2026	$316K
June 2026	$326K
May 2026	$319K
April 2026	$320K
March 2026	$318K
February 2026	$315K
January 2026	$310K
2025
December 2025	$313K
November 2025	$318K
October 2025	$324K
September 2025	$320K
August 2025	$321K
July 2025	$322K
June 2025	$322K
May 2025	$328K
April 2025	$323K
March 2025	$317K
February 2025	$314K
January 2025	$314K
2024
December 2024	$318K
November 2024	$315K
October 2024	$317K
September 2024	$320K
August 2024	$322K
July 2024	$321K
June 2024	$324K
May 2024	$319K
April 2024	$317K
March 2024	$313K
February 2024	$306K
January 2024	$304K
2023
December 2023	$307K
November 2023	$311K
October 2023	$317K
September 2023	$316K
August 2023	$317K
July 2023	$316K
June 2023	$309K
May 2023	$308K
April 2023	$304K
March 2023	$300K
February 2023	$295K
January 2023	$291K
2022
December 2022	$292K
November 2022	$294K
October 2022	$295K
September 2022	$299K
August 2022	$296K
July 2022	$275K
June 2022	$275K
May 2022	$269K
April 2022	$269K
March 2022	$267K
February 2022	$265K
January 2022	$262K
2021
December 2021	$261K
November 2021	$249K
October 2021	$248K
September 2021	$246K
August 2021	$241K
July 2021	$240K
June 2021	$239K
May 2021	$238K
April 2021	$237K
March 2021	$236K
February 2021	$236K
January 2021	$239K
2020
December 2020	$235K
November 2020	$224K
October 2020	$220K
September 2020	$219K
August 2020	$218K
July 2020	$221K
June 2020	$220K
May 2020	$219K
April 2020	$216K
March 2020	$215K
February 2020	$215K
January 2020	$216K
2019
December 2019	$215K
November 2019	$214K
October 2019	$213K
September 2019	$209K
August 2019	$233K
July 2019	$231K
June 2019	$227K
May 2019	$230K
April 2019	$229K
March 2019	$227K
February 2019	$226K
January 2019	$225K
2018
December 2018	$223K
November 2018	$223K
October 2018	$222K
September 2018	$221K
August 2018	$221K
July 2018	$221K
June 2018	$221K
May 2018	$220K
April 2018	$220K
March 2018	$219K
February 2018	$217K
January 2018	$218K
2017
December 2017	$208K
November 2017	$204K
October 2017	$205K
September 2017	$198K
August 2017	$201K
July 2017	$200K
June 2017	$199K
May 2017	$194K
April 2017	$193K
March 2017	$191K
February 2017	$196K
January 2017	$197K
2016
December 2016	$189K
November 2016	$194K
October 2016	$195K
September 2016	$196K

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
1 Overbrook Drive, Middlebury, VT	0.06	Condo	$379,000	09/30/25	2	1	1,008
22 Overbrook Dr, Middlebury, VT	0.04	Condo	$259,000	05/05/26	2	1	1,616
31 Evergreen Lane, Middlebury, VT	0.40	Condo	$340,000	08/18/26	2	2	1,397
17 Twin Circle, Middlebury, VT	0.29	Condo	$385,000	05/13/26	2	2.5	1,894
36 Brush Lane #8.3A, Middlebury, VT	0.51	Condo	$480,000	05/01/26	2	2	1,434
14 Brush Lane #8.1A, Middlebury, VT	0.51	Condo	$480,000	02/19/26	2	2	1,434
28 Brush Lane #8.2A, Middlebury, VT	0.51	Condo	$480,000	03/05/26	2	2	1,434
50 Brush Lane #8.4A, Middlebury, VT	0.52	Condo	$636,500	06/05/26	2	2	1,434
54 Brush Lane #8.4B, Middlebury, VT	0.51	Condo	$510,000	08/07/26	3	2	1,660
24 Brush Lane #8.2B, Middlebury, VT	0.51	Condo	$717,700	03/19/26	3	2	1,660

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
26 Overbrook Drive, Middlebury, VT 05753	0.07	$363,800	2	1	1,016	Off Market
1 Overbrook Drive, Middlebury, VT 05753	0.06	$395,200	2	1	1,008	Off Market
18 Overbrook Drive, Middlebury, VT 05753	0.06	$384,700	2	1	1,829	Off Market
19 Overbrook Drive #19, Middlebury, VT 05753	0.07	$392,200	2	1	1,008	Off Market
5 Swanage Court, Middlebury, VT 05753	0.09	$495,000	3	1.5	1,764	For Sale
13 Overbrook Drive, Middlebury, VT 05753	0.10	$395,700	3	2	1,812	Off Market
12 Overbrook Drive, Middlebury, VT 05753	0.10	$424,400	3	2	1,875	Off Market
23 Fairview Circle, Middlebury, VT 05753	0.16	$538,400	4	2	1,400	Off Market
276 Monroe Street, Middlebury, VT 05753	0.18	$415,600	3	2	1,704	Off Market
89 Court Street, Middlebury, VT 05753	0.19	$280,000	4	2	1,344	For Sale
209 Danyow Drive, Middlebury, VT 05753	0.20	$442,000	3	1	2,197	Off Market
235 Rogers Road, Middlebury, VT 05753	0.21	$390,300	3	1	1,120	Off Market

Local Information

Map ViewExplore the area around 2 Overbrook Dr.
Schools1 Preschool School1 Elementary School1 Middle School1 High School
Shop & Eat

-- mins to

Commute Destination

Home Highlights

Condo

Built in 1988

1,008 sqft

$313/sqft

Garage

About this House

This condo is located at 2 Overbrook Dr, Middlebury, VT. 2 Overbrook Dr is in Middlebury, VT and in ZIP code 05753. This property has 2 bedrooms, 1 bathroom and approximately 1,008 sqft of floor space. This property was built in 1988.

2 Overbrook Dr, Middlebury, VT 05753 is a 2 bedroom, 1 bathroom, 1,008 sqft condo built in 1988. It last sold for $235,000 on Feb 12, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $315,300, with a rent estimate of $1,893/month.

Home Details for 2 Overbrook Dr

Interior Features
Heating & Cooling Heating: Baseboard, Electric, GasHeating Fuel: Baseboard
Interior Details Types of Rooms: Dining Room
Appliances & Utilities Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility Floors: Carpet, Concrete, Linoleum Vinyl

Exterior Features
Exterior Home Features Roof: AsphaltDeckExterior: Vinyl
Parking & Garage GarageParking Space: 1Parking: Garage Detached

Property Information
Year Built Year Built: 1988
Property Type / Style Property Type: CondoArchitecture: Contemporary

Price and Tax history

Date	Event	Price
Feb 12, 2021 Source: PrimeMLS #4841405	Sold	$235,000
Dec 23, 2020 Source: PrimeMLS #4841405	Contingent	$239,000
Dec 10, 2020 Source: Agent Provided	Listed For Sale	$239,000
Jul 3, 2019 Source: N/A	Sold	$210,000
Sep 30, 2004 Source: N/A	Sold	$143,000

Year	Property tax	Tax assessment
2024	Unavailable	$192,500

Additional Cost

Market trends in Middlebury

Last updated July 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

Around this home

Mary Hogan School
PK-5
Public
484 Students
Addison Central Unified School District
8/10
GreatSchools Rating
Parent Rating Average
Excellent parent communication, small class sizes and plentiful access to educators beyond the core subjects make Mary Hogan an amazing school!
Parent Review
4y ago
2 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 Middlebury

At least 17 Trulia users voted on each feature.

89 % Say car is needed
76 % Say people would walk alone at night
72 % Say yards are well-kept
71 % Say it's dog friendly
64 % Say there's wildlife
61 % Say parking is easy
60 % Say it's walkable to restaurants
59 % Say there's holiday spirit
54 % Say neighbors are friendly
52 % Say it's quiet
50 % Say it's walkable to grocery stores
50 % Say they plan to stay for at least 5 years
48 % Say there are sidewalks
45 % Say there are community events
39 % Say kids play outside
27 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.

Jaimelshelfon
Resident
2y ago
"Great school district College town but not a party school Historically charm meets modern style and interests Easy and convenient public transportation for after school activities "
1
Flag
Drobinson
Resident
8y ago
"I’ve lived in this neighborhood for almost 30 years. Neighbors are friendly, but also respect privacy. Wooded area, but close to town center. "
2
Flag

LGBTQ Local Legal Protections

Frequently asked questions about 2 Overbrook Dr

What is 2 Overbrook Dr estimated to be worth?
Trulia's estimated value for 2 Overbrook Dr in Middlebury, VT is $315,300.
What is the price history for 2 Overbrook Dr?
2 Overbrook Dr in Middlebury, VT last sold for $235,000 in February 2021.
Is Middlebury a buyer's or seller's market?
Middlebury is currently a balanced market, based on recent for-sale activity.
What do residents say about Middlebury?
Residents describe Middlebury, VT as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Middlebury, VT.
Does 2 Overbrook Dr have laundry facilities?
Yes, 2 Overbrook Dr in Middlebury, VT has in-unit laundry.