Active Under Contract
Price CutPrice Drop: $200K (11/03)
Single family home for sale at 40 Ruffin Rd, Woodbury, CT 06798 | MLS# 24184948 | Listing updated on 2026-11-03
Photo 1 of Single family home for sale at 40 Ruffin Rd, Woodbury, CT 06798 | MLS# 24184948 | Listing updated on 2026-11-03
Photo 2 of Single family home for sale at 40 Ruffin Rd, Woodbury, CT 06798 | MLS# 24184948 | Listing updated on 2026-11-03
Photo 3 of Single family home for sale at 40 Ruffin Rd, Woodbury, CT 06798 | MLS# 24184948 | Listing updated on 2026-11-03
Photo 4 of Single family home for sale at 40 Ruffin Rd, Woodbury, CT 06798 | MLS# 24184948 | Listing updated on 2026-11-03
36+
Beds Icon

Street View

$1,590,000

Monthly Est:$7,914

  • Beds Icon4 Beds
  • Beds Icon
    3 Baths
  • Beds Icon2,732sqft

40 Ruffin Rd, Woodbury, CT 06798

$7,914/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1881

  • $-- HOA

  • 6.3 acres lot

  • $582/sq.ft

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 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. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.

  • Houzeo last checked: 25 minutes ago
  • Listing updated: November 3, 2026 at 2:06 pm
  • Listing Provided by: Mary Ann Bennett | Drakeley Real Estate, Inc.
  • Source: SMART MLS-CT | MLS#: 24184948 SMART MLS-CT

Property Details

  • Status

    Active Under Contract

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Litchfield County

  • City

    Woodbury

  • Neighborhood

    --

  • Year Built

    1881

  • HOA Fees

    -

  • Finished Area

    2,732 sqft

  • Lot Size

    6.3 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24184948

  • MLS Status

    Under Contract - Continue to Show

  • Days on Market

    141

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 4

    Bathrooms: 3

Interior

  • Sewer

    Septic

  • Interior Features

    Auto Garage Door Opener, Cable Pre Wired, Central Vacuum, Security System

  • Cooling

    Central Air

  • Heating

    Hot Water, Oil

  • Exterior Features

    Porch Screened, Shed, Porch, Barn, Gutters, Garden Area, Stone Wall, French Doors, Patio

  • Appliances

    Gas Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer

Construction

  • Year Built

    Year Built: 1881

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial

  • Foundation Details

    Concrete, Stone

  • Roof

    Asphalt Shingle, Wood Shingle

Utilities & Energy

  • Parking Features

    Barn, Detached Garage, Driveway

  • Basement

    Crawl Space, Full, Interior Access

  • Laundry Features

    Main Level

  • Water Source

    Private Well

  • Pool Features

    Vinyl, In Ground Pool

Other Features

  • Subdivision Name

    N/a

  • Lot Features

    Level Lot, Professionally Landscaped, Water View

Price History

DateEventPrice

11/03/2026

Source: mls_logoSMART MLS-CT #24184948

Contingent (Active Under Contract)

$1,590,000

$582/sqft

08/31/2026

Source: mls_logoSMART MLS-CT #24184948

Price Decreased

$1,590,000 -11.17%

$582/sqft

07/17/2026

Source: mls_logoSMART MLS-CT #24184948

Price Decreased

$1,790,000 -5.79%

$655/sqft

06/19/2026

Source: mls_logoSMART MLS-CT #24184948

Listed for Sale

$1,900,000 +204.00%

$695/sqft

12/10/1999

Source: mls_logoSMART MLS-CT #98053129

Sold

$625,000

$229/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Nov 07, 2026, 04:45AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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