348 Weekeepeemee Road, Woodbury, Connecticut

$2,149,900

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5

Beds

5

Baths

5,973

Square feet

9.48

Acres

About 348 Weekeepeemee Road

Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully designed living space. Multiple bedroom suites and an open floor plan provide room for everyone, with inviting spaces for both everyday living and entertaining. The beautiful kitchen opens to a covered porch overlooking an expansive patio and gunite pool, creating a seamless connection between indoor and outdoor gatherings. Car enthusiasts will appreciate the remarkable garage and barn space. An attached, heated three-car garage is complemented by a lower-level garage with room for several additional vehicles. An impressive detached barn, constructed with steel and concrete, accommodates another six to eight cars and features heat, a half bath, glass garage doors, and both upper- and lower-level access. Outside, meticulous landscaping and a paved driveway enhance the setting, while a spacious front patio provides the perfect spot to enjoy the sunsets. An open meadow offers room for outdoor celebrations or potential equestrian use. With its generous living spaces, exceptional vehicle storage, and beautifully maintained grounds, this distinctive property offers far more than the ordinary.

Features of 348 Weekeepeemee Road

MLS® # 24209591
Price $2,149,900
Bedrooms 5
Bathrooms 5.00
Full Baths 4
Half Baths 1
Square Footage 5,973
Acres 9.48
Type Single Family For Sale
Style Colonial
Status Active

Community Information

Address 348 Weekeepeemee Road
Area Weekeepeemee
City Woodbury
County Litchfield
State Connecticut
Zip Code 06798

Amenities

Features Thermopane Windows
Parking Barn, Attached Garage, Under House Garage
# of Garages 10
Is Waterfront No
Waterfront Not Applicable
Has Pool Yes
Pool Gunite, Spa, In Ground Pool

Interior

Interior Features Auto Garage Door Opener, Open Floor Plan, Security System
Appliances Gas Range, Subzero, Dishwasher, Washer, Dryer
Heating Hot Air, Hydro Air, Oil
Cooling Central Air
Fireplace Yes
# of Fireplaces 4
Has Basement Yes
Basement Full, Unfinished, Storage, Walk-out, Concrete Floor, Full With Walk-Out

Exterior

Exterior Clapboard
Exterior Features Terrace, Barn, Gutters, Patio, Sidewalk, Porch, Garden Area, Covered Deck, Stone Wall
Lot Description Fence - Wood, Farm Land, Level Lot, Cleared, Professionally Landscaped, Rolling
Roof Asphalt Shingle
Foundation Concrete

School Information

Elementary Per Board of Ed
Middle Woodbury
High Nonnewaug

Additional Information

Date Listed September 27th, 2026
Days on Market 3
Zoning OS100
RE / Bank Owned No

Listing Details

OfficeDrakeley Real Estate, Inc.

Listing Map

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Listing information last updated on October 6th, 2026 at 10:14pm EDT.