Second Homes for Sale CT - Litchfield County

Find all vacation properties and second homes for sale in Litchfield County.

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!

36 Chimney Point New Milford CT 06776

MLS Number 170110911

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

AMAZING PRICE 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. 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: 4.28% last updated on Mar 21, 2019
* 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

5 Mill Pond Sherman CT 06784

Price$1,000,000

Est. Mortgage: $/month

MLS Number 170018911

  • Land
  • Acreage 12.63

Finally, the place to build the perfect second home on Candlewood Lake- located in an gated community with private tennis, beach, marina, and the most spectacular views. This approved site with over 12 acres of incredible views affords the discerning buyer the ability to build a stunning home with ample garage space, a pool, a greenhouse- let your imagination be your guide! This is a one of a kind opportunity on Candlewood Lake- less than 1.5 hours from NYC. The possibilities and the views are magical!

Listing Courtesy of Douglas Elliman of Connecticut

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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

86 & 88 Lake New Fairfield CT 06812

MLS Number 170046607

  • Single Family
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.62
  • Square Feet 3,200

DRASTIC REDUCTION due to damage from May 2018 Tornado. Being Listed AS IS until spring. Buy and rebuild to your liking. Great opportunity for stunning direct waterfront compound in one of Candlewood Lake's finest gated communities, Candlewood Isle. All photos are PRIOR to Tornado! Main house minimally damaged, guest house has extensive damage. Two, Two bedroom direct waterfront cottages with stunning water views from almost every room. Rebuild as was or possibly a larger main house, many possibilities on a large lot in great location! Each cottage with 2 bedrooms, 2 full baths. The outdoor space is amazing. Stone driveway leads to a 2 car garage. The stone patios and decks let you take the party outside to enjoy the lake views and western sunsets! Lakeside there is a lovely stone patio and total of 4 docks, two for each house. There is also a fishing shed waterside. Candlewood Isle amenities include a lovely club house, community beach and boat slips, a play ground, tennis courts and so much more. There are summer camps for the children. This is a great life style and would make a great full time or vacation home. Opportunity to make it your own! Call listing agent for showings and details! Located 75 minutes from NYC!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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$900,000

Est. Mortgage: $/month

MLS Number 170091589

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

REDUCED $200,000 from original asking price!New construction by Master Craftsman on 5.49 acre lot in Roxbury. Built to or exceeds energy efficiency standards and includes a one year warranty. 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 with 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: 4.28% last updated on Mar 21, 2019
* 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 Wheaton Washington CT 06794

MLS Number 170166214

  • Single Family
  • Property Style Cape Cod, Cottage
  • Bedrooms 1
  • Bathroom 1
  • Acreage 13.17

Enter tree-lined driveway. Cape/ Cottage home w/ 1 bdrm on 1st floor. Loft on upper level. Amazing views of rolling hills in the serenity of a private landscape. Open land with lightly wooded edges, stone walls and flowing East Aspetuck river on west side of property. Located in the heart of Washington Depot, it boasts privacy sitting on a quiet road, while still close to the center of town. With nearby pleasures of Lake Waramaug just 1 mile away. The lake also has world class restaurants, nearby vineyards and EnRoute of CT Wine Trail, enjoy wine tastings, a golf course, and shopping. This beautiful 13.17 acres, displaying a 1100 sq ft cape cod house, an antique barn, stables, paddock and fenced in areas for the ponies. Endless opportunities, this property is perfect for agricultural farming with a reported 85% solar potential, possibility of subdividing or a perfect vacation home. This is truly worth a showing! Right side of property 225 ft road front. Left side 60 ft road front. Center driveway in right-of-way of 31 Wheaton Rd property.

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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 Wheaton Washington CT 06794

MLS Number 170147740

  • Land
  • Acreage 13.17

Enter tree-lined driveway. Watch sunrises and sunsets while enjoying the view of the rolling hills. Open land with lightly wooded edges, stone walls and flowing East Aspetuck river on west side of property. Located in the heart of Washington Depot, it boasts privacy sitting on a quiet road, while still close to the center of town. With nearby pleasures of Lake Waramaug just 1 mile away. The lake also has world class restaurants, nearby vineyards and EnRoute of CT Wine Trail, enjoy wine tastings, a golf course, and shopping. This beautiful 13.17 acres, displaying a 1100 sq ft cape cod house, an antique barn, stables, paddock and fenced in areas for the ponies. Endless opportunities, this property is perfect for agricultural farming with a reported 85% solar potential, possibility of subdividing or a perfect vacation home. This is truly worth a showing! Right side of property 225 ft road front. Left side 60 ft road front. Center driveway in right-of-way of 31 Wheaton Rd property.

Listing Courtesy of Coldwell Banker Residential Brokerage

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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

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: 4.28% last updated on Mar 21, 2019
* 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

2 individual houses** for the price of one , both parcels are multi families . Great return on investment , 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 $6,000 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: 4.28% last updated on Mar 21, 2019
* 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

339 South Litchfield CT 06759

Price$149,900

Est. Mortgage: $/month

MLS Number 170154552

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.52

Close to the center of the Litchfield Green. This home is being sold in "as-is" condition. There are 3 bedrooms 1 bath and a lower level that could be finished off for additional living space. This home needs renovation works and is priced accordingly. Easy to show, please schedule today. Located less than 2 hrs from NY this would make an ideal small second home.

Listing Courtesy of Marrin Santore Realty LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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 Coldwell Banker Realty 2000

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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 Coldwell Banker Realty 2000

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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

66 Westwoods Road 2 Sharon CT 06069

MLS Number 170175161

  • Rental
  • Property Style Barn
  • Bedrooms 6
  • Bathroom 6
  • Acreage 10.12

Available July or August at $19k per month.. Gorgeous Barn Style Home with Pool on Level acres, Open Floor Plan and patio for great entertaining... all in quiet a private setting, just minutes from Kent and Sharon Centers in Ellsworth Area of Sharon. Granite Fireplace with Beamed ceiling in Living Room. Gourmet Kitchen, Master Suite with Cathedral Ceiling, his and her Master Bath, Walk in Closet, 3 brs Ensuite. Private guest or in law apartment. Beautiful Pastoral Area,... The ultimate in Vacation Homes!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 4.28% last updated on Mar 21, 2019
* 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.