Second Homes for Sale CT - Litchfield County

Vacation Home in CTLooking for your perfect vacation home in Connecticut? Here you’ll find all vacation properties and second homes for sale in Litchfield County. From waterfront retreats to land ready to build on, you’ll find a variety of properties. 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!

CT Vacation Homes for Sale

Contact The Matthews Group with any questions about buying a vacation home or to schedule a private viewing.

57 Far Hills Avon CT 06001

Avon, CT57 Far Hills Drive

Price$1,350,000

Est. Mortgage: $/month

MLS Number 170336567

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 7
  • Acreage 2.14

Elegant, stately sophistication abounds in this grand brick-and-stone Colonial atop Far Hills Drive on over 2 acres, with 5 bedrooms, 5.2 baths, 4 car garage and 8,123 sqft in one of Avon's most sought-after neighborhoods on a quiet Cul-De-Sac road. Outstanding Kitchen offers DCS gas cooktop w/4 burners plus griddle, double wall ovens, Sub-Zero Refrigerator, large Island, Butler's Pantry w/wet bar & wine cooler, and gracious breakfast dining area that opens to large deck & fireplaced Family Room. Large Mud Room is conveniently located right off the Garage & Kitchen, w/1st floor laundry room & back stairway. The Foyer opens to a Grand Dining Rm w/elaborate molding details & tray ceilings, w/French doors that open to the Formal, gas-fireplaced Living Rm. More French doors open to the Library/Home Office with beautiful cherry built-ins. Commodious, incredibly well-appointed Master suite has a total of 3 walk-in closets, gas fireplace, tray ceiling, 2 full bathrooms, steam shower, a deep jetted tub, a second home office with more built-ins completing the Suite. Upstairs Bedrooms include dramatic vaulted ceilings & large closets, 2 bedrooms share Jack & Jill Bath, the fourth bed ensuite bath. 2nd floor Laundry Room. The walkout lower level is perfect for entertaining, with an open floorplan that offers a full wet bar, game area, Family Room, full bath & ample storage. Very Private, tree-lined rear yard. Conveniently located on Avon's East Side. A wonderful address to call Home!

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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760 Lake Winchester CT 06098

Winchester, CT760 Lake Drive

Price$739,900

Est. Mortgage: $/month

MLS Number 170328177

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.12
  • Square Feet 1,764

**Exciting direct waterfront property! This is your escape to paradise! Highland Lake is approx.2 hrs. from NYC or Boston, minutes to Rt 8 and close to all the restaurants, wine trails and breweries Litchfield County has to offer. This exquisite home was entirely rebuilt in 2012! Enjoy lots of beautiful sunsets, sun filled rooms, 3 fireplaces and all the accoutrements of lakeside living. This home has it all! Three bedrooms, 3 bathrooms, and a great room with beautiful vaulted ceilings and many windows, allowing natural light to fill your home. The beautiful view from your trex decks and dock will inspire you! Beautiful open living and kitchen area with all the appliances and work space any chef would want. Lovely master bedroom with gas fireplace vaulted ceiling, hardwood floors and walk in closet. This is a home or hideaway for every season! Pay for your own vacation home with weekly rentals at $3000 or nightly at $400 as current owner has been doing!!

Listing Courtesy of Northwest CT Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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680-B Mountain Torrington CT 06790

Torrington, CT680-B Mountain Road

Price$729,900

Est. Mortgage: $/month

MLS Number 170296067

  • Single Family
  • Property Style Ranch
  • Bedrooms 2
  • Bathroom 1
  • Acreage 113.8

INDIAN LOOKOUT Historic site with expansive breathtaking views on over 113 acres +/- offering crisp clean air and making an ideal weekend retreat, second home, or year-round living. The charming 1946 brick country ranch is sited at the top point of the property offering eastern and western mountain views of Litchfield county for miles. The entire parcel is comprised of seven separate parcels. Abundant wildlife is everywhere with trails and plenty of room for horses and or farm animals (as there are outbuildings) and gardens and additional building sites with views and privacy. Buyers must have pre-approval before showing.

Listing Courtesy of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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37 Forge Hill Barkhamsted CT 06063
Pending

MLS Number 170325772

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 5
  • Acreage 28.15

A perfect primary residence or picturesque second home, this stunning property offers 28+ acres with space to raise animals. Absolute privacy is guaranteed on this cul-de-sac, boasting with views to the southwest and Ski Sundown in winter. Filled with character, this freshly painted and move-in-ready home has 9 ft. ceilings, 2 vintage fireplaces, wainscoting, crown molding, built in cabinets, and refinished cherry and oak floors with walnut inlay. Large windows allow for plentiful natural light, including custom blinds. New stainless steel appliances accentuate the sizable kitchen with sufficient storage and pantry space. The eat-in kitchen area includes laundry and a mini-bar. Step out to 1 of 2 decks on the property, overlooking landscaped gardens. In addition to 4 bedrooms, all with walk-in closets, this home also provides a WFH office space and insulated 3-season porch with new ductless HVAC. Downstairs, the finished basement has full-height ceilings, half bath, rec area, and new ductless HVAC. It also includes roughed-in-piping for a future kitchen and a private entrance from the 3-car garage. Extra property features include but not limited to: a mudroom, central A/C, 5-zone LP gas boiler, an additional in-line wood boiler, sprinkler system, and a gravel road for future outbuilding. This one-of-a-kind-property is set within the Fuller Farms subdivision and has future development potential along with approved in-law or accessory plans and accompanying septic.

Listing Courtesy of Berkshire Hathaway NE Prop.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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168 Watertown Morris CT 06763

Morris, CT168 Watertown Road

Price$649,900

Est. Mortgage: $/month

MLS Number 170333870

  • Single Family
  • Property Style Colonial
  • Bedrooms 7
  • Bathroom 6
  • Acreage 3.18

2 Separate homes on over 3 acres of land in Morris. The main house offers 4 bedrooms and 2 and 1/2 baths. Living room, eat in kitchen, dining room on main level. Hardwood floors throughout first floor. Sliders off of family room lead to deck. Great kitchen with stainless steel appliances. Large bedrooms with plenty of closet space. Master bathroom has jet tub. Basement is finished with an additional kitchen and bath. Perfect for apartment or in law set up. First home has 2 car garage, large lot and shed. The second home has 2 bedrooms, living room with fireplace, eat in kitchen and one car garage. Square footage and rooms are combined for both homes for listing. Plenty of space for everyone! Don't miss this rare opportunity.

Listing Courtesy of Dave Jones Realty, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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22 Candlewood New Milford CT 06776

MLS Number 170327041

  • Single Family
  • Property Style Raised Ranch
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.32

Welcome to the neighborhood! Enjoy all the benefits of New England living! Mountain and lake views, beaches, boating, and horses, all perfectly nestled between the rolling meadows of Candlelight Farm and Inn and the shores of Candlewood Lake. This impeccable, light filled contemporary ranch features a vaulted living room with hardwood floors, year round lake views, and a wood burning stove. Home has been recently painted and updated with modern bathroom and lighting fixtures throughout. The expansive lower level family room also offers year round lake views and sliders to a patio area. French doors from the dining room lead to a 620 square foot deck, perfect for entertaining as your private community beach, boat dock and boat slip are all just a walk away. Easy commute to New York City, and minutes to Sherman, CT. Ideal as a year round or vacation home. Boat dock available for $1500 per season. Full house generator stays.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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8 Riverton Colebrook CT 06021
Pending

MLS Number 170316472

  • Single Family
  • Property Style Cape Cod, Cottage
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.08

The Historic BASS HOUSE circa1847 is located on Colebrook's Historic Row. This brick storybook cottage style home is punctuated with historic detail inside and out and offers a spacious light-filled living and open dining-kitchen. The primary bedroom is privately sited at the rear of the house with two additional bedrooms and a bath on the second level. A charming study is tucked away offering multiple uses. A spacious covered front porch overlooks lush grounds that offer privacy and a quaint two-bedroom cottage for use as a guest house or for an income-producing venue. The location is close to a variety of recreational choices and charming historical villages making it an ideal year-round or second home. The Bass House literally presents a quaint precious postcard setting.

Listing Courtesy of Elyse Harney Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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349 New Harwinton Torrington CT 06790

MLS Number 170240179

  • Multi Family Multi-Family For Sale
  • Property Style Other
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.48

GREAT INCOME PRODUCING OPPORTUNITY! TWO on ONE lot each with attached garages. Currently brings in $2,700 a month! The front home is 1,907 square feet, 4 bedrooms, 1 full bath, stone fireplace & attached private garage. The second home is 1,090 square feet, 2 bedrooms, 1 full bathroom, a 1/4 bath upstairs in the master suite with a walk-in close, and an attached garage. Great for someone looking for an in-law set up. Live in one & rent the other or a great opportunity to build your real estate portfolio or to start one. The location is wonderful, the back yard is ample, and the curb appeal is simply lovely. Both properties are solidly built & feature wonderful upgrades making them desirable, not to mention the income they can provide with their great rents. Upgrades include roof, siding, appliances, paved driveway and windows on both homes. One of them offers newer water heater, oil furnace, and front & back doors all leaving you with a peace of mind that your new homes are well maintained. Torrington hosts the historical Warner Theater, a most wonderful children's museum-Kid's Play, schools, playgrounds, Eastwood Country Club, fantastic downtown community with a plethora of shopping and multiple dining options. Route 8 & Route 44 easily guide you to New York City & Massachusetts!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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195 Scout Southbury CT 06488

Southbury, CT195 Scout Road

Price$187,500

Est. Mortgage: $/month

Pending

MLS Number 170318820

  • Single Family
  • Property Style Ranch
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.46

downsizing, vacation home? Looking for one level. Needs TLC. but you can get into Southbury for under 200K. almost a half acre lot, 2 car det gar. Very close to the state boat launch. short walk! 2 bedrooms, 1 bath, LR w HW floors. 2 unf rooms in lower level, warm air heat. come take a look and make offers, house is an estate.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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7 Tanmar Danbury CT 06810

Danbury, CT7 Tanmar Drive

Price$119,000

Est. Mortgage: $/month

MLS Number 170312238

  • Land
  • Acreage 1.12

Situated on 1.22 ac of private wooded home site for a 4 br home. Private road with few houses. Level to slight slope site for walkout basement if desired. Great getaway on west side of town with easy access to highway, one of the largest mall, golf, restaurants, commuting. Perc test witnessed by town . Build a year round main or vacation home

Listing Courtesy of Blue Lighthouse Realty, Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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108 Quanopaug Woodbury CT 06798

Woodbury, CT108 Quanopaug Trail

Price$109,900

Est. Mortgage: $/month

MLS Number 170190670

  • Land
  • Acreage 1.05

Surrounded by Open Space and Flander's Nature Preserve, yours to enjoy for eternity, this 1.05 acres of improved land is located on one of Woodbury's charming quintessential country roads. The ready to build lot is at the end of a private drive and abuts seemingly endless acres of woods, vernal streams, and abundant wildlife. Building your home here is all about enjoying nature yet being under 15 minutes to interstate 84. Owners donated over 100 acres to Flander's, preserving the land around you for eternity. Pay taxes on 1.05 acres but have all the benefits of being surrounded by Nature Preserve, yours to enjoy. The picturesque tree-lined Main Street and antiques shops aplenty have helped Woodbury earn Reader's Digest magazine's Most Charming Small Town in Connecticut designation in 2018. Come build your full time residence or your dream weekend/vacation home.

Listing Courtesy of Drakeley Real Estate, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.87% last updated on Sep 17, 2020
* 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.

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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.