40 Ruffin Rd

Woodbury, CT 06798

$1,900,000
Price
4
Beds
2,732 Sq. Ft.
$695 / Sq. Ft.
2,732
Sq. Ft.
$695
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Hobbyist dream heated work shop
Prefer a party barn? AI generated
Oversized tandem garage bays off workshop
Amazing potential for studio
Imagine what this studio space could be! (Virtually staged)
This potential studio space overlooks the pool and grounds - super light for painting!

Description

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...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.
  1. Listed by Mary Ann Bennett • Drakeley Real Estate, Inc.
    P: (203)-206-7048 C: (203)-206-7048 maryann@drakeley.com

Property Details for 40 Ruffin Road

Basement Description
Crawl Space, Full, Interior Access
Direct Waterfront
Yes
Garages Number
5
Neighborhood
N/A
Style
Colonial
Garage Parking Info
Barn, Detached Garage, Driveway
Swimming Pool
Yes
LISTING UPDATED: 06/25/2026 03:24 PM

Property Details for 40 Ruffin Road

StatusActive
MLS #24184948
Days on Market9
Taxes$10,041 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1881
Lot Size6.30 AC / 274,428 SF
CountyLitchfield County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Drakeley Real Estate, Inc., Mary Ann Bennett
Add your commute

Building Information for 40 Ruffin Road

Stories-Year Built1881Building Size-Lot Size6.30 AC / 274,428 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$10,305 per month

30 year fixed, 6.36% Interest

Principal and Interest

$9,468

Property Taxes

$837

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 40 Ruffin Road

Summary
Property and Location
  • Acres Source: Public Records
  • 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 not work, use Google maps
  • Elementary School: Mitchell
  • High School: Nonnewaug
  • Latitude: 41.564397
  • Longitude: -73.218672
  • Neighborhood Amenities: Golf Course, Health Club, Library, Medical Facilities, Private School(s), Stables/Riding, Tennis Courts
  • State: Connecticut
Parking
  • Parking Total Spaces: 20
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $10,041
Interior and Exterior Features
Exterior Features
  • Exterior Features: Porch-Screened, Shed, Porch, Barn, Gutters, Garden Area, Stone Wall, French Doors, Patio
  • Pool Description: Vinyl, In Ground Pool
  • Waterfront Description: River
Interior Features
  • Appliances Included: Gas Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
  • Attic Description: Access Via Hatch
  • Cooling System: Central Air
  • Heat Type: Hot Water
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Security System
  • Laundry Room Info: Main Level
  • Laundry Room Location: in butler's pantry off kitchen
  • Rooms Additional: Workshop
  • Rooms Total: 8
Room 1
  • Room Entry Order: 1
  • Room Features: Beams,Dining Area,Fireplace,French Doors,Patio/Terrace,Wide Board Floor
  • Room Level: Main
  • Room Type: Great Room
Room 2
  • Room Entry Order: 2
  • Room Features: Built-In Hutch,Dining Area,Dry Bar,Pantry,Wide Board Floor
  • Room Level: Main
  • Room Type: Kitchen
Room 3
  • Room Entry Order: 3
  • Room Features: Bay/Bow Window,Wide Board Floor
  • Room Level: Main
  • Room Type: Living Room
Room 4
  • Room Entry Order: 4
  • Room Features: Wide Board Floor
  • Room Level: Main
  • Room Type: Den
Room 5
  • Listing Key: 5479D4DFBABE5264E063E201100A7C76
  • Room Entry Order: 5
  • Room Features: Wide Board Floor
  • Room Level: Main
  • Room Type: Office
Room 6
  • Room Entry Order: 6
  • Room Features: Book Shelves,Bedroom Suite,Built-Ins,Full Bath,Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 7
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 9
  • Listing Key: 5479D4DFBABE5264E063E201100A7C76
  • Room Entry Order: 9
  • Room Features: Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Color: white
  • Construction Description: Frame
  • Driveway Type: Private, Gravel
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete, Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Wood Shingle
  • Year Built: 1881
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 2732
Lot Information
  • Lot Description: Level Lot, Professionally Landscaped, Water View
  • Parcel Number: 933676
  • Sq Ft Est Heated Above Grade: 2732.0
  • Sq Ft Total: 2732.0
  • Zoning: OS100
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: No
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 40 Ruffin Road

DateEvent & SourcePriceAppreciation
Dec 9, 1999

Closed (Public Record)

Public Record #91983421

$625,000—
DateEvent & SourcePrice
12/09/1999

Closed (Public Record)

Public Record #91983421

$625,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 40 Ruffin Road

Taxable ValueLand$73,360Additions$351,750Total$425,110
Tax Record2024$10,041 ($837 / month)
Home Facts
Beds5Baths2.5Total Finished SqFt2,732 SqFtAbove Grade Finished SqFt2,732 SqFtUnfinished Basement SqFt1,467 SqFtStories2Lot Size274,428 SqFtStyleSingle Family ResidenceYear Built1881Year Renovated1999ZoningOS100CountyNAUGATUCK VALLEYAPNWOOD M:039 B:013Fireplace TypeHas Fireplace

Schools near 40 Ruffin Road

This home is within Regional School District 14.
Rating
School
Type
Grades
Distance
Bethlehem Elementary School
Public - PK to 5
Mitchell Elementary School
Public - PK to 5
Woodbury Middle School
Public - 6 to 8
Nonnewaug High School
Public - 9 to 12
Rating
School
Distance
Bethlehem Elementary School
PublicPK to 5

Mitchell Elementary School
PublicPK to 5

Woodbury Middle School
Public6 to 8

Nonnewaug High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Explore Nearby Homes

More information about 40 Ruffin Road, Woodbury, CT 06798

40 Ruffin Road is a single family home for sale in Woodbury, CT 06798. This property was listed for sale on June 18, 2026 by Drakeley Real Estate, Inc., it's currently listed at $1,900,000. It has been on the market for a total of 9 days and was last sold on December 9, 1999. This listing's school district is Regional School District 14. Nearby schools include Bethlehem Elementary School, Mitchell Elementary School and Woodbury Middle School. 40 Ruffin Road is a 4-bed, 3-bath, 2,732 sqft single family home built in 1881.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Drakeley Real Estate, Inc., Mary Ann Bennett

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.