Second Homes for Sale CT - Litchfield County

Find all vacation properties and second homes for sale in Litchfield County. Narrow down results by selecting criteria on the right-hand side to find the home that meets your needs. Determine a price range, specify a town, how many bedrooms, etc. Knowing what you're looking for will not only help you focus your search but will also help your real estate agents understand your needs so that we can best assist you in the process. 

Sign up with our site to get a leg up on your property search and be the first to hear about new listings! Already registered? Log in to save your searches and favorite listings to start reaping the benefits!

We are available around the clock to help with your search or answer your questions, give us a call or contact us now!

29 Griswold Ln, Winchester, CT 06098

InternalID G10231854

  • Residential
  • Bedrooms 3
  • Bathroom 1
  • Acres 0.67
  • SqFt 600

1 of only 15 parcels on an private lake. includes dock and 200 ft of lake frontage. Price below appraised value. Must be seen to be appreciated. Very private and clean, great fire pit on property and fenced in. Plenty of room for parking. New pump for water source. Make this your next vacation home. Seller financing available to qualified buyers. Annual membership fee is determined at end of season meeting. ($400 - $800 usually)

Listing Courtesy of Morrow Realty, LLC

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

4 W Lakeview Rd, Plymouth, CT 06782

InternalID G10226224

  • Residential
  • Bedrooms 2
  • Bathroom 1
  • Acres 0.24
  • SqFt 780

Own for less than you can rent! Calculations show that you could own this home for less than $1000 a month with no money down if you qualify! Beautiful one floor living by Lake Plymouth! This ranch features 2 beds, 1 bath and 2 car garage with new roof. Situated on a level lot, enjoy the lake year round with 2 beaches or have a beautiful summer/vacation home! A great value - come look today!

Listing Courtesy of BHHS New England Properties

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

67 River Rd, Washington, CT 06794

InternalID L10225783

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Acres 0.78
  • SqFt 2240

This 4BR/3.5B Country Oasis awaits you, perfect for a second home or year round living. Fall in love with the backyard, soon as you set eyes on the picturesque Thomas Kinkade-like scenery with stone bridge, stream with stone walls and gorgeous flowers. Built by a local craftsman in 1954, yet totally renovated with old world charm, while preserving the original granite fireplace, wood floors and chestnut cabinetry, built-ins & molding. There is a first floor bedroom with sliders to enjoy the views from the stone terrace, and at one time there was also a first floor master bedroom, which is now used as a formal dining room. Recent renovations include: newer roof, siding, dormers, double pane windows, garage doors, kitchen/addition and upgraded electric and plumbing. Also, a new well was put in 2006 and septic system in 2004. The pristine Shepaug River is right across the street, and Steep Rock preserve is right down the road, offering incredible hiking trails, cross country skiing, biking and fishing. The quaint Litchfield County town of Washington Depot and surrounding towns offer gorgeous lakes, chic shops, wineries, great restaurants, galleries and private schools. For those who want to move right in to a home that is updated and ready, this is it!

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

39 Cemetery Hill Rd, Cornwall, CT 06796

InternalID L10221332

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acres 6.47
  • SqFt 4240

This exceptional custom built 10 room home is located on 6.4 private acres in the hills of Litchfield County, Connecticut. The charming cedar shingled home is beautifully sited with an gardens, open lawn, mature trees, pergola, & stone fences. Entering the home you'll notice 9' ceilings, natural lightening, cherry floors, & enticing flow of the floor plan. The living room with wood burning fireplace & French doors lead to the Trex deck; family room with built-ins; dining room; & kitchen with custom cherry cabinets, granite countertops, Wolf propane stove are on the first floor. Each room is generously sized in this 4-5 bedroom home with 4½ bathrooms. Custom made mahogany doors & moldings, French doors, & built-in's are throughout the house. Master bedroom with full bath & balcony. There are 3 additional bedrooms & sitting room on the upper levels. Recently remodeled lower level has engineered hardwood floors & includes an exercise room, a recreation room or bedroom, walk-in closet & full bath. Propane forced air heating, 14 KW whole house generator, 2 car attached garage, wood stove & whole house sprinkler system. The 600 square foot au pair or in-law apartment is also perfectly suited as an office. 730 sf workshop with cathedral ceiling is ideal as an artist studio, office, or party barn. Complete with radiant heat in the floor & new metal roof. Meticulously cared for this turnkey home with high-end finishes is perfect for full time or for second home living.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

2 Hillside Ave, Plymouth, CT

InternalID P10221665

  • Multi Family
  • Property Style Other
  • Acreage 0.4
  • Square Feet 3276

Imagine the possibilities! Two houses on one lot! House number one is multi family with excellent rental history a multi which has replacement windows, new roof in 2010, newer boiler in 2008. First floor electrical rewired in 2013. Security lighting and blown in insulation make this a great investment or home. The second home is a single family loaded with character awaiting the right owner to restore it to its original condition. Plus a barn and a brook make this an incredible find.

Listing Courtesy of Select Realty Associates, LLC

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

72 Washington Rd, Woodbury, CT 06798

InternalID W10219190

  • Condo
  • Bedrooms 1
  • Bathroom 1
  • Square Feet 544

Convenient close to everything location with just a gentle stroll from parking to the front door. (No stairs to climb) Low maintenance for easy living. This is a perfect starter home or home for folks wishing to scale down. An ideal second home for anyone wishing to get out of the routine of a hectic city lifestyle. Updated kitchen with the added bonus of a stack washer/dryer. Lease Purchase possible.

Listing Courtesy of Adams & Adams Real Estate

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

Westside Rd, Goshen, CT 06756

Price$75,000

Est. Mortgage: $/month

InternalID L10216135

  • Land
  • Acreage 3.2

Located on a quiet road, this 3.2 acre level lot would make a great place to build a primary or vacation home. Lightly wooded, gentle elevation, area of nice homes. A-s survey completed.

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

35 Bohun Rd, Colebrook, CT 06021

InternalID P10210333

  • Land
  • Acreage 2.67

Privacy awaits you in this approved building lot located on private dirt road near end of cul-de-sac located on the State line of Connecticut and Massachusetts! In the heart of the Litchfield and Berkshire counties; local activities include summer and winter festivals, hiking, bicycling, skiing, antiquing, music, theatre, dance, film, white water tubing, golf and fly fishing plus much much more! Perfect place to build your permanent residence or even your vacation home as a winter cabin or summer getaway! With under half an hour from the Berkshires you are sure to keep busy with all of the celebrations of the seasons, or just sit back and relax in the beauty that surrounds this natural retreat. Just under 3 acres available for purchase as well as additional abutting 9+ acre parcel. With a walk away from a sprawling 350+ acre Camp Bobriwka your options are endless with the neighboring private camp resort! One mile from YMCA Camp Jewel, 31 miles from Lenox, MA (location of Tanglewood Festival), 20 miles from Great Barrington, MA (location of Ski Butternut), 22 miles from Torrington, CT (location of Warner Theater), 23 miles from Lakeville, CT (location of Music Mountain), 21 miles from New Hartford, CT (location of Ski Sundown & Farmington River Tubing) and 9 miles from Norfolk, CT (location of Infinity Hall and the Yale Summer School of Music and Norfolk Chamber Music Festival). Schedule your showings today!

Listing Courtesy of RE/MAX Edge

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

33 Bohun Rd, Colebrook, CT 06021

InternalID P10206442

  • Land
  • Acreage 1.84

Privacy awaits you in this approved building lot located on private dirt road near end of cul-de-sac located on the State line of Connecticut and Massachusetts! In the heart of the Litchfield and Berkshire counties; local activities include summer and winter festivals, hiking, bicycling, skiing, antiquing, music, theatre, dance, film, white water tubing, golf and fly fishing plus much much more! Perfect place to build your permanent residence or even your vacation home as a winter cabin or summer getaway! With under half an hour from the Berkshires you are sure to keep busy with all of the celebrations of the seasons, or just sit back and relax in the beauty that surrounds this natural retreat. Just over 9+ acres available for purchase as well as additional abutting 2.5+ acre parcel. With a walk away from a sprawling 350+ acre Camp Bobriwka your options are endless with the neighboring private camp resort! One mile from YMCA Camp Jewel, 31 miles from Lenox, MA (location of Tanglewood Festival), 20 miles from Great Barrington, MA (location of Ski Butternut), 22 miles from Torrington, CT (location of Warner Theater), 23 miles from Lakeville, CT (location of Music Mountain), 21 miles from New Hartford, CT (location of Ski Sundown & Farmington River Tubing) and 9 miles from Norfolk, CT (location of Infinity Hall and the Yale Summer School of Music and Norfolk Chamber Music Festival). Schedule your showings today!

Listing Courtesy of RE/MAX Edge

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

2 Dillon Beach Rd, Barkhamsted, CT 06063

InternalID G10210345

  • Residential
  • Bedrooms 4
  • Bathroom 5
  • Acres 0.64
  • SqFt 3500

Thinking vacation? It's better “for keeps”! An absolute gem, this original circa 1850 home was expanded and remodeled for its completion in 2005, and includes “#3 Dillon Beach Road”, direct waterfront on one of CT's most spectacular bodies of water, West Hill Lake. The spacious cedar clad residence overlooks the lake and it's own private beach and two docks. The 260 acres of sparkling spring fed water attracts swimmers, SUP's, kayaks, canoes and year round fishing for trout, bass, and Kokanee salmon.Other local recreation includes hiking, camping, river fishing, tubing, and winter skiing. With 3500+ sq.ft, the home offers a rare sanctuary, yet ideal for entertaining. An expansive kitchen features island work area & seating, farm sink, granite counters, built in hutch, and double ovens. Adjacent space continues to the formal dining area accented with architectural detail. A great room offers a massive stone fireplace and full wet bar opening directly to the huge 700' deck. 1st floor suite also opens onto the deck, has it's own fireplace, dressing area, full bath, and private sauna. First floor also has office & bonus room with separate entrance. Endless possibilities here; perhaps professional use? Vacation home? Sure. But why not stay year round? Location is ideal; under 15 mins to Litchfield, 30 minutes to Bradley Int'l Airport, and under an hour to the Berkshires, Stockbridge, Tanglewood, shopping outlets, antique markets, summer theatre and festiva

Listing Courtesy of William Raveis Real Estate

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

1240 Bantam Rd, Litchfield, CT 06750
Pending

InternalID L10197936

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Acres 3.95
  • SqFt 1698

Nestled in the Litchfield Hills of historic Litchfield, this circa 1742 antique saltbox is situated on almost 4 acres. Lovingly updated and maintained, this historic home features wide board wood flooring, exposed beams, a central fireplace, updated kitchen, bathroom and newer roof. Exterior features include a patio, stonewalls, fenced in backyard and outbuilding. Mechanical features include updated electrical panel, central air, well and septic. Minutes away from Bantam center. Enjoy the area hiking, skiing, biking, fishing, golfing, health club and horseback riding. Approximately two hours to New York City. A fine full-time or second home. "Let me live in my house by the side of the road and be a friend to man."

Listing Courtesy of William Pitt Sotheby's Int'l Realty

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details

95 Shinar Mountain Rd, Washington, CT 06794
Under Agreement

InternalID G10188397

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Acres 3.71
  • SqFt 2312

Ultimate gettaway property! enjoy all the views Washington has to offer! enjoy this house as a Connecticut vacation home or stay here all year long! 3 beds 3 full baths and over 2300 sqft. in ground pool, central air, large master w/ fireplace and surrounded by protected land. one of Washingtons most desirable and recognizable street names!

Listing Courtesy of Agnelli Real Estate LLC

The Matthews Group
4 Green Hill Road
Washington Depot CT, 06794
Office: 860.868.0511

Do not fill in this field:

Do not fill in this field:

$
$
%
$/month over payments
Federal 30-year interest rate: 3.95% last updated on Apr 27, 2017
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Save FavoriteSchedule A VisitAsk A QuestionMore Details