30 Upland Road Winchester, CT $ 220,000
30 Upland Road
$ 220,000
Recently Listed
Share Save

30 Upland Road

Winchester, CT, 06098
$ 220,000
Bedrooms4 Baths2.0 Sq 1,844

Monthly Estimate*

$ 1,355

30 Upland Road, Winchester, CT 06098 - Image 1
30 Upland Road, Winchester, CT 06098 - Image 2
30 Upland Road, Winchester, CT 06098 - Image 3
30 Upland Road, Winchester, CT 06098 - Image 4
30 Upland Road, Winchester, CT 06098 - Image 5
30 Upland Road, Winchester, CT 06098 - Image 6
30 Upland Road, Winchester, CT 06098 - Image 7
30 Upland Road, Winchester, CT 06098 - Image 8
30 Upland Road, Winchester, CT 06098 - Image 9
30 Upland Road, Winchester, CT 06098 - Image 10
30 Upland Road, Winchester, CT 06098 - Image 11
30 Upland Road, Winchester, CT 06098 - Image 12
30 Upland Road, Winchester, CT 06098 - Image 13
30 Upland Road, Winchester, CT 06098 - Image 14
30 Upland Road, Winchester, CT 06098 - Image 15
30 Upland Road, Winchester, CT 06098 - Image 16
30 Upland Road, Winchester, CT 06098 - Image 17
30 Upland Road, Winchester, CT 06098 - Image 18
30 Upland Road, Winchester, CT 06098 - Image 19
30 Upland Road, Winchester, CT 06098 - Image 20
30 Upland Road, Winchester, CT 06098 - Image 21
30 Upland Road, Winchester, CT 06098 - Image 22
30 Upland Road, Winchester, CT 06098 - Image 23
30 Upland Road, Winchester, CT 06098 - Image 24
30 Upland Road, Winchester, CT 06098 - Image 25

Single Family Home for sale in Winchester, CT

for $220,000 with 4 bedrooms and 2 full baths. This 1,844 square foot home was built in 1869 on a lot size of 0.17.

Located in the charming community of Winsted, this 4-bedroom home is tucked away in a quiet, low-traffic neighborhood while still being close to many local amenities. Hardwood floors run throughout the home, adding warmth and character, and the tree-lined backyard offers a private outdoor setting to enjoy year round. This home also features a beautiful enclosed second-floor sun porch, perfect for relaxing with morning coffee, reading, or enjoying the changing seasons. A large walk-up attic provides abundant storage space and may offer the potential to be finished for additional living area, office space, or a hobby room. Just a short distance away, you will find the local library, coffee shops, parks, restaurants, and a variety of neighborhood shops and conveniences. Outdoor enthusiasts will appreciate nearby Highland Lake, offering opportunities for boating, swimming, and recreation throughout the warmer months. This home does need some TLC and updating, but with vision and effort, it has the potential to truly shine. Whether you are looking for a primary residence or an investment opportunity, this property offers excellent potential in a desirable location.

See more

Single Family Active

Price

$ 220,000

Bedrooms

4

Full Bath

2

Property Type

Single Family

Taxes

$ 3,204

Style

Lot Size

0.17

Year Built

1869

Town/City

Winchester

MLS | Web ID

24176921

Features
General
Zoning R-3
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 0.17
Directions Route 44 Main Street to Upland Rd
High School Per Board of Ed
City Winchester
Elementary School Per Board of Ed
Sq Ft Total 1844
DOM 0
Year Built 1869
Style Colonial
Year Built Source Public Records
See more
Interior
Cooling System None
Total Rooms 8
Basement Description Full Unfinished
See more
Exterior
Water Source Public Water Connected
Lot Description Level Lot Sloping Lot
See more
* Excluded Features
List By
Jeffrey Liskin

Listing Agent

Northwest Ct Realty

Broker

jliskinrealty@gmail.com

Email

Affordability Calculator

$1,622
Per Month
84%
16%
0%
Monthly Principal & Interest
$1,355
Monthly Property Taxes
$267
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3092524 Elementary School
1232933 Middle School
Per Board of Ed High School High School
Pricing History
DatePricePrice ChangeDescription
5/19/2026$220,000 Listed Price

Map


See all

30 Upland Road, Winchester, CT, 06098 is a Single Family Home for sale at $220,000 with 1,844 sqft and a lot size of 0.17. 30 Upland Road has 4 bedrooms, 2.0 baths, and was built in 1869. The property's zip code is 06098 which is in Winchester, CT