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.

306 West Hyerdale Goshen CT 06756

MLS Number 170311743

  • Single Family
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.86
  • Square Feet 2,771

Enjoy all the amenities of Woodridge Lake, in this fabulous light-filled country home, overlooking the West Shore of the lake. Walk across the road to West Beach to launch your kayaks or paddleboards, or take a swim. One of the most spectacular features of this home is the three-season views of the lake. Designed with the comforts & conveniences of a primary residence, yet as the open floor plan allows, can be used as a multi-generational second home. Perched upon a hill with a professionally landscaped yard, & perennial gardens, the wrap-around front porch will be your "go-to-place" for coffee in the morning, cocktails in the evening, or reading a& relaxing. The expansive back deck is the perfect place to enjoy the serenity of the beautiful garden or for hosting large events. The main living area includes hardwood floors, designer kitchen featuring a six-burner Viking stove, granite countertops, large island & a separate breakfast area that opens out to the back deck, grand living room with fieldstone gas fireplace and wooded views, a separate dining room facing the lake, and a den/office that provides a quiet work-from-home area & can double as an extra guest room. Also on the first level is the much-desired Master bedroom suite with a gas fireplace, surrounded by tumbled marble, & large bathroom with double marble vanity, whirlpool tub, and walk-in closets. Three bedrooms on the upper level with a Jack & Jill bath. Many expansion opportunities in the Attic and Lower level.

Listing Courtesy of Murphy E J Realty

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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.

Listing Courtesy of Elyse Harney Real Estate

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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41 Loon Meadow Norfolk CT 06058

Norfolk, CT41 Loon Meadow Drive

Price$695,000

Est. Mortgage: $/month

MLS Number 170296282

  • Single Family
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 3
  • Acreage 20.39

"THREE FEATHERS FARM" A safe haven offering an operating farm in pristine Norfolk Ct. This magical multipurpose property offers an upgraded country home on 20.39 acres with three barns, open pastures, and corals making it an ideal horse property. There are two ponds, trails throughout the property, organic gardens, fruit trees, and wide-open spaces. The farm offers a variety of uses from a working farm, second home, or country retreat. The completely upgraded home offers 3 bedrooms 2 1/2 baths, fully applianced kitchen. first-floor master bedroom suite offering a spacious bath, large walk-in closet, and French doors overlooking the farm. There is an in-law/studio apt and additional building sites for future use. There is abundant wildlife, forest, long-range views, and stunning blue skies. Solar panels for the option of living off the grid and a full generator. Close to dining choices, art, and entertainment, varieties of recreational choices, and cultural activities. Come home to fresh country air, endless opportunities, and a new sustainable way of living.

Listing Courtesy of Elyse Harney Real Estate

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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16 Bridge End Farm Newtown CT 06482

Newtown, CT16 Bridge End Farm Lane

Price$619,000

Est. Mortgage: $/month

Pending

MLS Number 170296571

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1.6
  • Square Feet 3,185

LIVE THE DREAM!! DIRECT WATERFRONT PROPERTY WITH DOCK ON LAKE ZOAR. Enjoy Boating, Jet Skiing, Kayaking, Canoeing, Swimming & Fishing here at your own PRIVATE RESORT! The VIEWS OF THE LAKE from the floor to ceiling windows surrounding the FAMILY ROOM are breathtaking. A roaring fire burning in the Family Room's CUSTOM FIELDSTONE FIREPLACE on the cooler days, while gazing out at the lake, is the tranquility you deserve. Step out to the freshly painted deck, overlooking the large level backyard w/PANORAMIC VIEWS OF THE LAKE. Located in a fabulous neighborhood, this spacious, 3,125 sq.ft., 3/4 bedroom, 3 full bath Contemporary Colonial has been freshly PAINTED inside, has a NEWER ROOF, CEDAR SIDING, FURNACE, A/C and a NEWLY SEALED DRIVEWAY. You'll savor your culinary experiences in the KITCHEN, using the updated stainless steel appliances, as you glance up & capture the PLACID WATERVIEW in front of you. The lovely dining room will accommodate all of your guests. One of the bedrooms & full bath is LAKE FRONT on the main level. Upstairs FACING THE WATER is the large MASTER BEDROOM w/FULL BATH, FIREPLACE, WALK-IN CLOSET & SITTING AREA. Completing the upper level is another bedroom, full bath, office/4th bedroom & laundry room. There is an oversized 2 car garage as well as a garage for storing your boat, jet ski/s, & canoe/s. This is a home to truly enjoy living life. Come make this your own STAYCATION or VACATION HOME!! ***ONLY 90 MINUTES FROM NYC***

Listing Courtesy of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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33 Wheaton Washington CT 06794

MLS Number 170147740

  • Land
  • Acreage 13.17

Price Reduced to SELL! 13+ acres w/ Barn 7 stalls & Cape/cottage. House needs work and is being sold AS IS. 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, golf course, and shopping. This beautiful 13.17 acres, displaying a 1100 sq ft Cape Cod style home, 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 Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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33 Wheaton Washington CT 06794

MLS Number 170166214

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

Price Reduced to SELL! House, Barn and 13+ acres. 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. House needs work sold AS IS.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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11 College Hill North Canaan CT 06024

MLS Number 170268623

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.4

OWLS NEST is located on a hillside adjacent to a gentle forest with open spaces. The colonial-style home offers a large private deck with a hot tub overlooking the private grounds. A large rustic screened-in porch provides privacy while maintaining an outdoor feeling. There are 3/4 bedrooms and 3 1/2 baths. The formal entry opens to a spacious living room with a large stone fireplace and french doors. There is also a spacious formal dining room off the foyer. The kitchen is filled with amenities and a private informal dining area. The family room off the kitchen has a stunning raised stone fireplace. The partially finished basement provides a variety of choices for additional living space. There is abundant storage. The privacy of the grounds provides a haven for gentle wildlife such as deer, owls, and turkey. OWLS NEST is ideal for year-round living or a second home. Also available on a separate deed is a two-story barn/2stall garage on 6.50 acres.

Listing Courtesy of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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28 Brick School Warren CT 06754

Warren, CT28 Brick School Road

Price$264,900

Est. Mortgage: $/month

MLS Number 170292434

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 2
  • Acreage 2.65

Well maintained contemporary Dome on private setting. New septic system! Main level features Living Room, Lovely Kitchen, Dining Room, Family Room, 2 Bedrooms, Full Bath, and Laundry. Upstairs features Master Bedroom with Full Bath, adjoining Sitting room, and large walk-in closet. Nice deck to barbeque on. This is a must see!! Enjoy Warren Woods and the town beach on Lake Waramaug. Enjoy shops, vineyard, and restaurants just a short drive away along with hiking and ski trails. Great vacation home or full time residence!

Listing Courtesy of Showcase Realty, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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 Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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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2 Dilliston Barkhamsted CT 06063

MLS Number 170308167

  • Single Family
  • Property Style Bungalow
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.1

Location... Location... Location... of your new seasonal vacation home. Just steps away to the pristine waters of West Hill Lake and The North End General Store, known for their lobster rolls and live music. Home has deeded beach rights to private LAPOA beach. Interior has 2 bedrooms, eat in kitchen, living room with fireplace, and can sleep 6+ people. Beautiful enclosed porch and outdoor patio expands your outdoor living space. Nice level yard with mature perennial landscaping, shed for your beach toys and a circular driveway. Beach rights and shared community well water is supplied by association with annual fees. Summer has just begun ... don't miss out on spending this summer in your new getaway!

Listing Courtesy of The D'Amore Agency, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.03% last updated on Jul 9, 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$139,000

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: 3.03% last updated on Jul 9, 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: 3.03% last updated on Jul 9, 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.