40 Ruffin Road
Woodbury, CT, 06798 $ 1,900,000
Bedrooms4 Baths2.1 Sq 2,732 Monthly Estimate*
$ 11,699
for $1,900,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,732 square foot home was built in 1881 on a lot size of 6.3.
It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. This private setting is less than five minutes to Historic Woodbury's town center and only 10 minutes to Washington Depot. Woodbury is Voted top three best places to live in CT according to Travel & Leisure.
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FeaturesGeneralZoning OS100
Neighborhood N/A
County Litchfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 6.3
Directions Ruffin Road is a private dirt road go all the way to the end. No RE sign at the beginning of the road just after or before the steel bridge pending approaching direction Wayz will work use Google maps
High School Nonnewaug
City Woodbury
Elementary School Mitchell
Sq Ft Total 2732
DOM 1
Year Built 1881
Style Colonial
Year Built Source Public Records
Pool Description Vinyl In Ground Pool
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InteriorCooling System Central Air
Total Rooms 8
Basement Description Crawl Space Full Interior Access
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ExteriorWater Source Private Well
Lot Description Level Lot Professionally Landscaped Water View
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* Excluded FeaturesList ByMary Ann BennettListing Agent
Drakeley Real Estate, Inc.Broker
maryann@drakeley.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $11,699
- Monthly Property Taxes
- $837
- 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 NearbySingle family listings in Woodbury, CT
Average List Price $822,466
Percent of Sale Price 57%
About Woodbury, CT 9,775 Population
6% Since 2002
$ 82,000 Median Income
50.35 Median Age
26% Households with Children
Trends Information provided by ATTOM Data Solutions.
1233322 Elementary School
1232807 Middle School
Nonnewaug High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 6/19/2026 | $1,900,000 | | Listed Price |