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!

145 Bentley, Goshen, CT 06756

MLS Number 170141737

  • Rental
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.9

Located within the prestigious private lake community of Woodridge Lake in West Goshen, the timeless design of this New England Country home is loaded with refined features. Whether you are looking for a turn-key vacation home within walking distance of Sunset Beach, with more amenities than you can imagine, or the best that year round lake/resort living can offer, this stylish home offers a spacious floor plan of 4300 sf and includes 4 generous sized bedrooms, a main floor office that can easily be a 5th bedroom, 3.5 bathrooms - all with quality finishes. The master bath has a jetted tub and a self-contained steam shower that you will especially enjoy in the winter months. The gourmet kitchen is accented with custom cabinetry, granite counters and newer stainless steel appliances. The lower level is completely finished and functions as a playroom, private guest suite for your visitors or large entertainment area that walks out through double French doors onto an idyllic grassy playyard and your private hot tub overlooking the woods that easily seats 6 guests. There are new wooden floors in the living room, office and family room as well as new carpeting in the upper level. Also listed for sale

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

145 Bentley, Goshen, CT 06756

Price$625,000

Est. Mortgage: $/month

MLS Number 170141659

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.9

Located within the prestigious private lake community of Woodridge Lake in West Goshen, the timeless design of this New England Country home is loaded with refined features. Whether you are looking for a turn-key vacation home within walking distance of Sunset Beach, with more amenities than you can imagine, or the best that year round lake/resort living can offer, this stylish home offers a spacious floor plan of 4300 sf and includes 4 generous sized bedrooms, a main floor office that can easily be a 5th bedroom, 3.5 bathrooms - all with quality finishes. The master bath has a jetted tub and a self-contained steam shower that you will especially enjoy in the winter months. The gourmet kitchen is accented with custom cabinetry, granite counters and newer stainless steel appliances. The lower level is completely finished and functions as a playroom for family members, private guest suite for your visitors or large entertainment area that walks out through double French doors onto an idyllic grassy play yard and your private hot tub overlooking the woods that easily seats 6 guests. There are new wooden floors in the living room, office and family room as well as new carpeting in the upper level. Priced to move quickly, this beauty must be seen to be truly appreciated.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

98 Ball Pond, Danbury, CT 06811

MLS Number 170141639

  • Single Family
  • Property Style Ranch
  • Bedrooms 7
  • Bathroom 7
  • Acreage 12.03

A deal you don't want to loose out on. This is an investors dream! This is a once in a lifetime opportunity in a prime location, less than 30 minutes to the NY border via I-684 highway and just minutes away from the Metro North Station, with the potential gross income currently at $6000 and additional land to build on. ..There are two separate homes on this 12 acre property - each unit subdivided with an in-law apartment and in excellent condition. The main house has three bedrooms, kitchen, dining, living, sunroom with brick fireplace and brick siding with a new roof added within the last 5 years. The second home with vinyl siding has an attached two car garage, outdoor deck, ,upper level partitioned 1 bedroom apartment and 3 bedroom apartment each with own bathrooms and also a lower level 1 bedroom accessory apartment. The Property is perfect for entertaining with nice frontage, plenty of backyard space and a huge enclosed gazebo. Remember there are 2 separate Multifamily homes included in this Deal!! . Perfect for in-law and / or investment purposes. It's a currently a well maintained great owner occupied property and also a great Investment opportunity for someone wanting to maximize on this 12 acres of sub dividable land in the future! Out of flood zone . No flood insurance needed

Listing Courtesy of Century 21 Scala Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

98 Ball Pond, Danbury, CT 06811

MLS Number 170133728

  • Multi Family Multi-Family For Sale
  • Bedrooms 7
  • Bathroom 7
  • Acreage 12.03
  • Square Feet 3,628

A deal you don't want to loose out on. This is an investors dream! This is a once in a lifetime opportunity in a prime location, less than 30 minutes to the NY border via I-684 highway and just minutes away from the Metro North Station, with the potential gross income currently at $6000 and additional land to build on. ..There are two separate homes on this 12 acre property - each unit subdivided with an in-law apartment and in excellent condition. The main house has three bedrooms, kitchen, dining, living, sunroom with brick fireplace and brick siding with a new roof added within the last 5 years. The second home with vinyl siding has an attached two car garage, outdoor deck, ,upper level partitioned 1 bedroom apartment and 3 bedroom apartment each with own bathrooms and also a lower level 1 bedroom accessory apartment. The Property is perfect for entertaining with nice frontage, plenty of backyard space and a huge enclosed gazebo. Remember there are 2 separate Multifamily homes included in this Deal!! . Perfect for in-law and / or investment purposes. It's a currently a well maintained great owner occupied property and also a great Investment opportunity for someone wanting to maximize on this 12 acres of sub dividable land in the future! Out of flood zone . No flood insurance needed

Listing Courtesy of Century 21 Scala Group

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

101 Eastview, Plymouth, CT 06786

MLS Number 170126686

  • Land
  • Acreage 0.12

This corner lot with views of the lake would make the perfect summer vacation home or stay for the year and make it year round. Established lake community with city sewer available in the street. Well required. Prefer a larger lot or additional privacy? The lot next door, Lot 99, is also available for sale. Buy both and uild the home of your dreams!

Listing Courtesy of Naugatuck Office

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

99 Eastview, Plymouth, CT 06786

MLS Number 170126684

  • Land
  • Acreage 0.03

This Corner lot is waiting for you to build you dream vacation home with beach rights to the lake, access and yera round views. Well is required but city sewer is available in the street. Need more space? Buy Lot #101 which is also for sale and not only have the home of your dreams but the privacy and acreage.

Listing Courtesy of Naugatuck Office

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

1206 Bassett, Watertown, CT 06795
Pending

MLS Number 170013872

  • Single Family
  • Property Style Colonial, Other
  • Bedrooms 6
  • Bathroom 6
  • Acreage 24

Your very own oasis at AKIN's FARM....Stunning Watertown Home in private location on 24 acres. This beautiful home is surrounded by nature, it's a stay-vacation home...... Nothing but peace and serenity. 10 rooms, 6 bedrooms with the Master Bedroom on main level. Family room with sliders to deck looking over beautiful view of the pond. Eat in Country Kitchen, formal Living room, office/study, wow 6 fireplaces for those cold cozy nights. Two barns, one having an apartment for your in laws. Plus a single family home for rent or for your visiting family members. 4 car garage, and so much more. Call for private tour today.

Listing Courtesy of Westbury Realty CT

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

216 Brick School, Warren, CT 06754

Price$589,000

Est. Mortgage: $/month

MLS Number 170115898

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3
  • Acreage 4.3

This rambling one level 3 bedroom home is set well back from a little traveled town road behind old stone walls. Designed for minimal care, this is the perfect second home in the country. In addition to the spacious rooms, there are 4 fireplaces (LR, DR, Study and MBR) and two large and luxurious bathrooms open on the back deck and the view of the pond. There is also a 1152 sq.ft. 3 car heated garage with a bath and workhsop space (think studio or guest house). There is also 1000 sq.ft. upper level now used for storage, but loaded with possibilities. First time offered. Builder's own home. Thoughtfully designed.

Listing Courtesy of Bain Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

36 Chimney Point, New Milford, CT 06776

MLS Number 170110911

  • Single Family
  • Property Style Chateau, Cottage
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.33

AMAZING REDUCTION Iconic Stone & Cedar Waterfront, in sought after Candlewood Lake Club, offers incredible western exposure w/expansive lake views, exceptional updates quality finishes creating an authentic lake home design. A vaulted great room framed by beams, stone fireplace & hardwood floors opens to a renovated kitchen w/off white cabinetry, quartz counters, stainless appliances and island bar. The circular dining area occupies one of 2 stone turrets surrounded by windows & lake views. The second turreted area offers a wonderful entertaining space with built-in bar & cabinetry and adjoining enclosed hot tub area for private relaxation.The master suite occupies an entire floor of it's own, with private bath, walk-in closet and lake views. Two additional main level bedrooms, with updated bath and additional option for half bath ( plumbed), offer great space for family & guests alike. Stunning stone terraces, stone walls and walks, U-shaped dock, lake side cabana, carport, circular drive & professionally landscaped gardens create the ultimate lake getaway! The Lake Club community offers tennis, private beach, clubhouse and 9 hole golf course available to members. Club bond of 10K is transferred with the property, $10,000 initiation fee for club membership, annual dues of only $4,000.00, $525 for water and $775 for capital road improvement, $500 for other. A true lake getaway with all the amenities for a fun vacation home or choose the "Lake Club" lifestyle all year long!

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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.

Virtual TourSave FavoriteSchedule A VisitAsk A QuestionMore Details

27 East Hyerdale, Goshen, CT 06756

Price$329,900

Est. Mortgage: $/month

Pending

MLS Number 170112960

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.85

Snuggled into the woods you will find this second tier home offering you the serenity that you long for in your vacation resort. Its bright open floor plan invites you to come in and relax in front of the fire on the chilly New England evenings. Observe nature at its finest on your two tiered deck off the dining room or appreciate the seasonal views of Woodridge Lake off your balcony. Your master suite offers you a romantic soaking tub surrounded by a gas fireplace and corner windows to look out at the stars. The double walk in closets offer plenty of storage for your treasures. Just a short distance in either direction will bring you to s sandy beach! The Woodridge Lake lifestyle offers you tennis courts, a club house, exercise facilities, pools, beaches, a play ground, marina, fishing and so much more! So whether you are looking for a year round or a vacation home, this one is the one for you! Bonus! A new furnace was just installed!

Listing Courtesy of Integrity Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

3 Beaver Dam, Newtown, CT 06470

Price$619,900

Est. Mortgage: $/month

MLS Number 170109973

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 2.38

READY FOR IMMEDIATE OCCUPANCY! The very best new construction in town! Gorgeous new subdivision, majestic views, a beautiful level back yard and a thoughtful layout. The expansive front porch greets you and is perfect for relaxing and enjoying quiet evenings. A formal dining room and study flank the bright and refreshing foyer. The builder has taken into consideration all of the latest in his design, keeping it trending yet classic. Hardwoods throughout the main level, with the exception of the tile mudroom/pantry off of the attached two car garage. The light and gracious eat-in kitchen opens to the great room with a fireplace, plenty of windows and sliders out to the back deck. Upstairs a beautiful master suite with sitting room and fireplace, beautiful bath with soaking tub and huge walk-in closet. The level back yard is the perfect spot for a pool, playground a little bocce or just a lovely spot to hang out in. This is the second home in a 6 home subdivision, surrounded by other established homes - New England living at it's finest. The property across the street is forever protected!!! We are ready for you to move right in!!! Energy Star High Efficiency home!!! Nothing but the best!!!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

18 Ranney Hill, Roxbury, CT 06783

Price$975,000

Est. Mortgage: $/month

MLS Number 170091589

  • Single Family
  • Property Style Other
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.49

New construction by Master Craftsman on 5.49 acre lot in beautiful Roxbury. Built to or exceeds todays energy efficiency standards and includes a one year warranty. This beautiful home is located close to town center on a quiet country road. This 4 bedroom, 3.5 bath, 3326 square foot shingle style home is built with the finest workmanship as well as the finest materials. The gourmet kitchen is amazing and features a center island and a stone fireplace. Thermador appliances include a 6 burner gas cooktop, a wall oven, built in microwave, a warming drawer, dishwasher and a refrigerator. The open floor plan features a large open area that can be set up as a living room/dining room combination or a variety of different ways as your life style dictates. There is a lovely sun room off the kitchen. There is a mud room area coming in from the garage and a half bath close by. The upper floor includes a lovely master suite with 2 walk in closets and a luxurious master bath with soaking tub, dual sinks and a tiled shower. There are 3 additional bedrooms, 1 en-suite and 2 share a hall bath. There are beautiful wood floors throughout and the beams used are from trees that were on the property. The house sits up high with mountain views. It is gently sloping with a level area with plenty of room for that soccer game. In the rear of the house is a blue stone patio with a site for a pool close by. Located within 90 minutes of NYC makes this a great second home or a full time home! Taxes TBD

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.94% last updated on Nov 15, 2018
* 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

Information contained in this Smart MLS listing has been compiled from various sources, all of which may not be completely accurate. Smart MLS makes no warranty or representation as to the accuracy of listing information. All information that influences a decision to purchase a listed property should be independently verified by the purchaser. Copyright 2017 Smart MLS, Inc. All rights reserved.