220 Upper Grassy Hill Road Woodbury, CT $ 759,900
220 Upper Grassy Hill Road
$ 759,900
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220 Upper Grassy Hill Road

Woodbury, CT, 06798
$ 759,900
Bedrooms3 Baths3.0 Sq 2,420

Monthly Estimate*

$ 4,679

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Single Family Home for sale in Woodbury, CT

for $759,900 with 3 bedrooms and 3 full baths. This 2,420 square foot home was built in 1960 on a lot size of 2.45.

Recently renovated from the studs up, this single-family ranch on the Woodbury/Roxbury town line offers the rare chance to own a truly like-new home with immediate availability. This three-bedroom home features all-new electrical, HVAC, spray-foam insulation, trim, drywall, hardwood floors, a beautifully updated kitchen, and three brand-new bathrooms. The main level offers a spacious layout with three bedrooms featuring wide pine flooring, two full tiled baths, a living room with a fireplace, and a stunning new eat-in kitchen. The finished walkout lower level adds approximately 800 square feet of versatile living space. This space is ideally suited for an in-law apartment, with a family room and fireplace, a full bath, space for a kitchen, and a private entrance. Set on a gorgeous 2+ acre lot at the top of Woodbury, the property also includes a small portion in Roxbury.

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Single Family Active

Price

$ 759,900

Bedrooms

3

Full Bath

3

Property Type

Single Family

Taxes

$ 5,936

Style

Lot Size

2.45

Year Built

1960

Town/City

Woodbury

MLS | Web ID

24163591

Features
General
Zoning OS80
Neighborhood Grassy Hill
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 2.45
Directions Rt 317 to Upper Grassy Hill Road
High School Nonnewaug
City Woodbury
Elementary School Mitchell
Sq Ft Total 2420
DOM 3
Year Built 1960
Style Ranch
Year Built Source Public Records
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Interior
Cooling System Central Air
Total Rooms 7
Basement Description Full Heated Cooled Partially Finished Walk-out Liveable Space Full With Walk-Out
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Exterior
Water Source Private Well
Lot Description Lightly Wooded Level Lot
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* Excluded Features
List By
Timothy Drakeley

Listing Agent

Drakeley Real Estate, Inc.

Broker

tim@drakeley.com

Email

Affordability Calculator

$5,174
Per Month
90%
10%
0%
Monthly Principal & Interest
$4,679
Monthly Property Taxes
$495
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.
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Nearby
1233322 Elementary School
1232807 Middle School
Nonnewaug High School High School
Pricing History
DatePricePrice ChangeDescription
4/4/2026$759,900 Listed Price

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220 Upper Grassy Hill Road, Woodbury, CT, 06798 is a Single Family Home for sale at $759,900 with 2,420 sqft and a lot size of 2.45. 220 Upper Grassy Hill Road has 3 bedrooms, 3.0 baths, and was built in 1960. The property's zip code is 06798 which is in Woodbury, CT