Is a car needed in Windham, CT?

As of early 2026, 76% of users say car is needed

Is parking easy in Windham, CT?

As of early 2026, 74% of users say parking is easy

Is Windham, CT quiet?

As of early 2026, 74% of users say it's quiet

Is there wildlife in Windham, CT?

As of early 2026, 70% of users say there's wildlife

Is Windham, CT dog-friendly?

As of early 2026, 68% of users say it's dog friendly

Are yards well-kept in Windham, CT?

As of early 2026, 67% of users say yards are well-kept

Do kids play outside in Windham, CT?

As of early 2026, 57% of users say kids play outside

Would people walk alone at night in Windham, CT?

As of early 2026, 53% of users say people would walk alone at night

Are neighbors friendly in Windham, CT?

As of early 2026, 52% of users say neighbors are friendly

Does Windham, CT show holiday spirit?

As of early 2026, 47% of users say there's holiday spirit

Are the streets well-lit in Windham, CT?

As of early 2026, 41% of users say streets are well-lit

Is Windham, CT walkable to restaurants?

As of early 2026, 37% of users say it's walkable to restaurants

Are there community events in Windham, CT?

As of early 2026, 36% of users say there are community events

Does Windham, CT have sidewalks?

As of early 2026, 32% of users say there are sidewalks

Do residents of Windham, CT plan to stay at least 5 years?

As of early 2026, 32% of users say they plan to stay for at least 5 years

Is Windham, CT walkable to grocery stores?

As of early 2026, 30% of users say it's walkable to grocery stores

OFF MARKET

39 Hilltop Dr
North Windham, CT 06256

3 Beds
2 Baths
1,176 sqft

$285,900

Trulia Estimate

as of Jul 13, 2026

Est. Refi. Payment $1,912/mo*

Refinance Your Home

$285,900

Trulia Estimate

as of Jul 13, 2026

Est. Refi. Payment $1,912/mo*

Refinance Your Home

3 Beds

2 Baths

1,176 sqft

Local Information

Map ViewExplore the area around 39 Hilltop Dr.
Schools2 Elementary Schools2 Middle Schools1 High School
Shop & Eat

-- mins to

Commute Destination

Description

This condo is located at 39 Hilltop Dr, North Windham, CT. 39 Hilltop Dr is in North Windham, CT and in ZIP code 06256. This property has 3 bedrooms, 2 bathrooms and approximately 1,176 sqft of floor space. This property was built in 2000.

39 Hilltop Dr, North Windham, CT 06256 is a 3 bedroom, 2 bathroom, 1,176 sqft condo built in 2000. It last sold for $135,900 on Feb 26, 2002. It is currently off market. The Trulia Estimate is $285,900, with a rent estimate of $2,224/month.

Home Highlights

Parking

Garage

Outdoor

No Info

A/C

Heating only

HOA

None

Price/Sqft

No Info

Listed

Less than a day ago

Home Details for 39 Hilltop Dr

Interior Features
Interior Details BasementNumber of Rooms: 5
Heating & Cooling Heating: Other, OilHeating Fuel: Other
Levels, Entrance, & Accessibility Stories: 1

Property Information
Year Built Year Built: 2000
Property Type / Style Property Type: CondoArchitecture: Other

Exterior Features
Parking & Garage GarageParking: Garage Attached

Community
Units in Building: 1

Price History for 39 Hilltop Dr

Date	Price	Event	Source
02/26/2002	$135,900	Sold	N/A
Recording Date 02/26/2002 County Transfer Tax N/A Total Transfer Tax N/A

Market trends in Windham

Last updated June 2026

Avg. sale price

—

Sale-to-List Price

—

Price per sq ft

—

Available listings

2MoM

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Property Tax and Assessment

Year	2025
Tax	$4,720
Assessment	$158,110

Home facts updated by county records

Comparable Sales for 39 Hilltop Dr

Address	Distance	Property Type	Sold Price	Sold Date	Bed	Bath	Sqft
6 Skyline Dr, North Windham, CT	0.08	Condo	$270,000	04/28/26	3	2	1,158
6 Skyline Drive #6, North Windham, CT	0.09	Condo	$270,000	04/24/26	3	2	1,158
34 Hilltop Drive #34, North Windham, CT	0.03	Condo	$293,000	08/11/25	3	2.5	1,922
40 Eastbrook Heights #C, Mansfield, CT	1.55	Condo	$236,500	05/12/26	3	1.5	1,032
51 Eastbrook Heights #C, Mansfield, CT	1.52	Condo	$195,000	10/31/25	2	1.5	982
54 Eastbrook Heights #A, Mansfield, CT	1.55	Condo	$223,000	02/27/26	2	1.5	1,192
19 Eastbrook Heights #C, Mansfield, CT	1.48	Condo	$250,000	12/18/25	2	2	1,408
366 Ash Street APT 2, Willimantic, CT	1.57	Condo	$225,000	11/11/25	2	1.5	1,210
48 Eastbrook Heights #C, Mansfield, CT	1.54	Condo	$240,000	04/06/26	2	1.5	946
29 Eastbrook Heights #A, Mansfield, CT	1.52	Condo	$198,000	11/25/25	1	1.5	1,013

Nearby homes

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

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OFF MARKET
Est. $232,100
2 bd
1 ba
1,220 sqft
41 Hilltop Drive,
North Windham, CT 06256
Home Selling Team
OFF MARKET
Est. $344,000
3 bd
2.5 ba
1,651 sqft
34 Hilltop Drive,
North Windham, CT 06256
Home Selling Team
OFF MARKET
Est. $309,900
3 bd
2.5 ba
1,922 sqft
34 Hilltop Drive #34,
North Windham, CT 06256
RE/MAX Coast and Country
OFF MARKET
Est. $288,500
3 bd
2 ba
1,362 sqft
40 Hilltop Drive,
North Windham, CT 06256
Home Selling Team
OFF MARKET
Est. $245,100
3 bd
2 ba
1,160 sqft
33 Hilltop Drive,
North Windham, CT 06256
FERRIGNO-STORRS, REALTORS
OFF MARKET
Est. $253,000
3 bd
2 ba
1,160 sqft
10 Skyline Drive,
North Windham, CT 06256
FERRIGNO-STORRS, REALTORS
OFF MARKET
Est. $268,200
3 bd
1.5 ba
1,320 sqft
12 Skyline Drive,
North Windham, CT 06256
FERRIGNO-STORRS, REALTORS
OFF MARKET
Est. $268,200
3 bd
1.5 ba
1,320 sqft
8 Skyline Drive,
North Windham, CT 06256
FERRIGNO-STORRS, REALTORS
OFF MARKET
Est. $309,200
3 bd
1.5 ba
1,320 sqft
8 Skyline Drive #8,
North Windham, CT 06256
Weichert,REALTORS-Four Corners
SOLD
APR 24, 2026
$270,000
3 bd
2 ba
1,158 sqft
6 Skyline Drive #6,
North Windham, CT 06256
William Raveis Real Estate
OFF MARKET
Est. $326,300
3 bd
2.5 ba
1,392 sqft
46 Hilltop Drive,
North Windham, CT 06256
Home Selling Team
OFF MARKET
Est. $268,200
3 bd
1.5 ba
1,320 sqft
4 Skyline Drive,
North Windham, CT 06256
FERRIGNO-STORRS, REALTORS

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Additional Cost

Assigned Schools

These are the assigned schools for 39 Hilltop Dr.

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 Windham

At least 25 Trulia users voted on each feature.

76 % Say car is needed
74 % Say parking is easy
74 % Say it's quiet
70 % Say there's wildlife
68 % Say it's dog friendly
67 % Say yards are well-kept
57 % Say kids play outside
53 % Say people would walk alone at night
52 % Say neighbors are friendly
47 % Say there's holiday spirit
41 % Say streets are well-lit
37 % Say it's walkable to restaurants
36 % Say there are community events
32 % Say there are sidewalks
32 % Say they plan to stay for at least 5 years
30 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.

Kissle26
Resident
3mo ago
"Its fine. My office is only a 10 minutes drive (or less). It’s mostly back roads but they are usually cleaned off and whatnot!"
0
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Lindsay F.
Resident
7y ago
"very quiet and friendly community, close enough to commute to and from hartford county but far enough away from the city to be able to enjoy rural settings"
1
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Bobbyquiles
Resident
7y ago
"Living here for 3 years now and we love the area. Quite and peaceful. The wild turkeys, deer, and he hummingbirds"
1
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Tiffany H.
Resident
8y ago
"Its 75% Puerto Rican. The taxes are very high. You pay for police, but they won't come. Only state police do, when they get around to it. "
0
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D L.
12y ago
"I lived in this area for 26 years. It has always been a great neighborhood! You have plenty of privacy while still being close to others to feel comfortable and supported. It is a great neighborhood for children or retirees. Beacon Rd. is only five miles from downtown where there are several restaurants and a variety of shopping for food and other needs. The schools do not get the credit that they deserve, but they are very progressive and they offer a variety of educational support services, both for the students and the staff. The student population is diverse and there is a brand-new state-of-the-art science-based school for grades K thru 8. They offer a variety of sports and other extra-curricular activities; football, soccer, track, swimming, baseball, softball, wrestling and tennis. They also offer before and after-school child care programs for grades K thru 8. There is a State University in the town of Willimantic, Eastern CT State University and UCONN (the University of CT') is only 17 miles away. Manchester CT is only about 25 miles away and there is all the shopping and stores that you could think of available there. Beacon Rd. has always been a great neighborhood to live in and to raise our kids in. It is well known as one of the "better" areas of Windham/Willimantic. The people take pride in their properties and the area has maintained a good value, even through these difficult times. There is ample parking for family and friends and the road is well maintained. Check it out! "
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