Litchfield Hills

Connecticut

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Steeped in historic charm, the scenic Litchfield Hills offers gracious country living amid a wealth of cultural and recreational opportunities

Tucked away in Connecticut’s rural northwest corner, Litchfield County encompasses 945 square miles, making it the largest county in the state. Known as the Litchfield Hills, the county, with 25 towns, two boroughs and two cities, is also the state’s least populated. Long a weekend enclave for artists and writers, the area boasts lovely historic homes, charming farmhouses and grand estates amid a stunning setting of pristine lakes, lush forests and rolling hills. The countryside evokes classic New England charm with its meandering stone walls, quaint antiques shops, historic inns, winding back roads, verdant wineries and fertile farmland.

Outdoor enthusiasts enjoy a plethora of recreational options, from hiking the Appalachian Trail to fly fishing on the Housatonic or water-skiing, boating or sailing on one of the county’s many pristine lakes. Residents and visitors enjoy annual events and festivities, including old-time country fairs, arts and crafts festivals, the Litchfield Jazz Festival, historic house tours, community theater, top-notch music venues and so much more.

Tucked away in Connecticut’s rural northwest corner, Litchfield County encompasses 945 square miles, making it the largest county in the state. Known as the Litchfield Hills, the county, with 25 towns, two boroughs and two cities, is also the state’s least populated. Long a weekend enclave for artists and writers, the area boasts lovely historic homes, charming farmhouses and grand estates amid a stunning setting of pristine lakes, lush forests and rolling hills. The countryside evokes classic New England charm with its meandering stone walls, quaint antiques shops, historic inns, winding back roads, verdant wineries and fertile farmland.

Outdoor enthusiasts enjoy a plethora of recreational options, from hiking the Appalachian Trail to fly fishing on the Housatonic or water-skiing, boating or sailing on one of the county’s many pristine lakes. Residents and visitors enjoy annual events and festivities, including old-time country fairs, arts and crafts festivals, the Litchfield Jazz Festival, historic house tours, community theater, top-notch music venues and so much more.

Tucked away in Connecticut’s rural northwest corner, Litchfield County encompasses 945 square miles, making it the largest county in the state. Known as the Litchfield Hills, the county, with 25 towns, two boroughs and two cities, is also the state’s least populated. Long a weekend enclave for artists and writers, the area boasts lovely historic homes, charming farmhouses and grand estates amid a stunning setting of pristine lakes, lush forests and rolling hills. The countryside evokes classic New England charm with its meandering stone walls, quaint antiques shops, historic inns, winding back roads, verdant wineries and fertile farmland.

Outdoor enthusiasts enjoy a plethora of recreational options, from hiking the Appalachian Trail to fly fishing on the Housatonic or water-skiing, boating or sailing on one of the county’s many pristine lakes. Residents and visitors enjoy annual events and festivities, including old-time country fairs, arts and crafts festivals, the Litchfield Jazz Festival, historic house tours, community theater, top-notch music venues and so much more.

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Litchfield Hills

Area Map

Litchfield Hills is in Connecticut and borders Fairfield County, The Berkshires.

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All of our

Litchfield Hills Communities

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Litchfield Hills

Market Snapshot

Units Sold

January 2026

77 TOTAL UNITS

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Median Sales Price

January 2026 - Single Family Homes

$595K
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Percentage of Asking Price

January 2026 Single Family Homes

95%
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95%
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95%
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95%
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95%
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95%
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Featured Listings

62 Big Bear Hill Road
New Milford, CT $8,200,000

62 Big Bear Hill Road

New Milford, CT

$8,200,000
  • 6 Beds
  • 7/2 Baths
  • 8,457 Sqft
23 Mauwee Brook Road
Kent, CT $7,400,000

23 Mauwee Brook Road

Kent, CT

$7,400,000
  • 4 Beds
  • 5/1 Baths
  • 5,400 Sqft
132 Curtiss Road
Warren, CT $6,999,999

132 Curtiss Road

Warren, CT

$6,999,999
  • 7 Beds
  • 7/3 Baths
  • 6,010 Sqft
102 South Shore Road
Salisbury, CT $5,875,000

102 South Shore Road

Salisbury, CT

$5,875,000
  • 4 Beds
  • 6/1 Baths
  • 6,100 Sqft
L7&l8 Willow Brook Drive
Roxbury, CT $5,499,000

L7&l8 Willow Brook Drive

Roxbury, CT

$5,499,000
  • 5 Beds
  • 3/1 Baths
  • 6,729 Sqft
210 Doolittle Drive
Norfolk, CT $4,490,000

210 Doolittle Drive

Norfolk, CT

$4,490,000
  • 6 Beds
  • 7/1 Baths
  • 5,671 Sqft
31a June Road
Washington, CT $4,000,000

31a June Road

Washington, CT

$4,000,000
  • 4 Beds
  • 3/1 Baths
  • 3,285 Sqft
79 Hilltop Road
Sharon, CT $3,995,000

79 Hilltop Road

Sharon, CT

$3,995,000
  • 6 Beds
  • 5/1 Baths
  • 6,121 Sqft