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. You may also be interested in browsing lake homes.

59 Ore Hill Salisbury CT 06039
Pending Continue to Show

MLS Number 170348686

  • Single Family
  • Property Style Contemporary, Modern
  • Bedrooms 2
  • Bathroom 2
  • Acreage 23.82

Very Special Home with Spectacular Pond This modern home combines stunning views with high energy-efficiency and low maintenance and taxes. The offering includes 4 abutting parcels which incorporate a +/-12 acre gorgeous Pond. The in-the-hillside home features a spacious open floor plan, high ceilings, 2 Bedrooms, 2 Full Baths, a very large Living Room, Kitchen, Dining Area, and Gym/Office/Studio all facing the Pond. There is also a potential for a second home with a septic system already in place. This remarkable home is on an exceptional property in the Lakeville section of Salisbury, CT - only minutes to Millerton, NY.

Listing Courtesy of Elyse Harney Real Estate

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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88 West Hyerdale Goshen CT 06756
Pending Continue to Show

MLS Number 170367463

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.01

This craftsman style country home offers wide open spaces. Set within the Woodridge Lake community with plentiful amenities, this home affords the luxuries both year round and vacation home owners have been looking for. Large viewing windows with south facing views of the lake and lawn offer many opportunities in furnishing this bright and artsy home. Indoors, there are 4 bedrooms and 3.5 baths, cherry hardwood, tile and carpeted floors. Stainless steel gas fired oven and refrigerator in kitchen, granite counters, sliders and eat in spaces. The grand room enjoys a fireplace, recessed lighting, large area for tables and chairs, and multiple areas for seating. Possible home office space upstairs. Lower level could be an in-law suite or au pair suite. A large outdoor deck sprawls cross the back of the house and includes a hot tub. A hand built stone wall and circular drive finish the landscaped setting. A must see at the lake.

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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12 Baker Roxbury CT 06783

Roxbury, CT12 Baker Road

Price$575,000

Est. Mortgage: $/month

MLS Number 170373157

  • Single Family
  • Property Style Cottage, Saltbox
  • Bedrooms 2
  • Bathroom 1
  • Acreage 3.71

Unique opportunity to acquire a Roxbury property with two homes that has been in the same family for nearly 45 years. The original ~1850 Salt Box with inviting lines and charm is ready for a new owner to introduce the comforts of their choice. In the rear of the property there is a second home built in 1995 that has an open space kitchen/dining/living room area and two bedrooms that share a hall bathroom. The ground level features a three-bay open garage created with the help of 14 inch steel beams that run 30 feet. The first bay is ~20 feet long and the other two are ~30 feet long with 8 foot clearance to the beams. The 3.7 acre parcel has plenty of cleared, level terrain. The land is rich with old growth spruce, pine, maple and other specimen trees. A brook runs east/west across the property between the two homes and feeds into a pond along the western edge.

Listing Courtesy of William Pitt Sotheby's Int'l

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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3 Peace Pipe Sherman CT 06784

MLS Number 170364802

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 1.93

1969 Sherman Connecticut Colonial, 1.93 acres, 2974 Square ft with original wood floors all rooms. Year round or a great vacation home just 70 miles from NYC and 30 minutes from Brewster North Train Station. The main level, the living room has a to ceiling Stone fireplace. Adjacent to that is a roughed in addition with sub floor and electricity intended to be a family room with stairs to second level 19x22 rec room. There is a large formal dining room and eat in kitchen and laundry room. Off of the kitchen is a large screened in porch with cement floor that runs the length of the home and could be glass in or finished to extend the kitchen or family area. The upstairs has 4 bedrooms but currently is set up as three with a sitting area. The ack yard has small flat fenced. Behind this area are steps that lead to about quarter acre that is mostly treed but was a formerly the pool area. Lastly, This area is near to Lake Mauweehoo which is ideal for canoeing or your kayaks. iTown Sherman offers a public beach on Candlewood Lake exclusively for residents. This home has great bones but needs extensive updating and is being sold as is with the new owner responsible for the clean out of debree.

Listing Courtesy of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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103 Toddy Hill Newtown CT 06482

MLS Number 170365971

  • Single Family
  • Property Style Cape Cod, Ranch
  • Bedrooms 3
  • Bathroom 2
  • Acreage 4.55

Two Homes for the price of one on 4.55 Wooded Acres. Rent from Second Home will reduce your mortgage payments while building equity. Perfect set up for a loved one to live privately next door. Many updates already completed to both properties. Cape a pleasure to show updated kitchen and bathrooms Ranch is 624 square feet, private deck. basement for storage, gas heat. Located in one of Connecticut's most desirable communities, with excellent schools. Convenient commute, 5 minutes to I-84 Route 34 and Route 25. Cape showing direct. Appointment with Tenant to show Ranch

Listing Courtesy of William Raveis Real Estate

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%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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173 Christian Middlebury CT 06762

Middlebury, CT173 Christian Road

Price$349,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170370267

  • Single Family
  • Bedrooms 3
  • Bathroom 1
  • Acreage 1.38
  • Square Feet 1,410

Where awesomeness happens! Cool landscape and privacy to be shared with friends and loved ones. Property features ample room so everyone has their own space to unplug and unwind. Home offers many upgrades: on demand hot water system, remodeled kitchen and baths, adorably redone guest house, central air, newer mechanicals, excellently maintained, completely turn key. Patio area includes grilling/cooking facility, private outdoor shower, lovely gardens overlooking a flat meadow for earthing. Walk to the lake for day fun and enjoy all water sports or experience a magical sunset... an abundance of peaceful country life within 73 miles of NYC. The charming historic Tribury area with hiking, biking paths, parks, antique and luxury shopping, theater, restaurants, and a huge variety of wellness facilities: fitness, yoga, meditation, beauty, massage-spa services, and a well renowned organic health food market. Each season in Connecticut has it's own magical aesthetics and events. Wedged between the hills of Litchfield County and coastal Fairfield County, commuting anywhere is a breeze. Perfect for full time residence, second home, or a fantastic AIRBNB opportunity. Middlebury is proud of the award winning school system and its' upward thinking about philanthropic endeavors. Come visit and see.

Listing Courtesy of Coldwell Banker Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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169 French Watertown CT 06795

Watertown, CT169 French Street

Price$329,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170363230

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 5
  • Bathroom 2
  • Acreage 0.95

Fantastic opportunity for investors or owner occupants with 2 houses including an in-law home. Both roofs less then 1 yr! Excellent cash flow for investment or to live with a large family. 5/6 bedrooms, 2 kitchens, 2 full bathroom. One home has 1900 sq feet the 2nd approx 900 sq feet totaling aprx 2800 sq feet of space. This lot has 2 individual cape cod homes with 2 separate sheds & plenty of lawn space & parking. Both homes have been remodeled and are turn key ready. The 1st home has hardwood floors through out the 1st & 2nd floor. The eat in kitchen offers plenty of counter space & new stainless steel appliances. Off the kitchen is a large 1st floor bedroom with plenty of light. There is a large living room with tons of natural light and a fire place. Upstairs are two larger bedroom with hardwood floors in each. The roof on this unit is less then a year old. The second home is remodeled as well with a newer roof, new replaced windows, paint and more. Hardwood floors in 2nd home are brand new in living room and 1st fl bed. Kitchen has upgraded flooring, new stainless steel appliances & a fully remodeled bathroom. Upstairs you have brand new carpet walking into a large 1-2 bedroom space. Outside you will find there is plenty of yard space for both homes, allowing each occupant to have their own areas. A huge newer shed and an additional smaller one. Plenty of parking, separate utilities, city water city sewer & natural gas heat. Take advantage of this unique turn key homes!

Listing Courtesy of Showcase Realty, Inc.

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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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 Old Turnpike North Canaan CT 06024
Open House

MLS Number 170349132

  • Single Family
  • Next Open House: Sat 03/6 2:00 pm. to 4:00 pm.
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 3

Spacious Antique home built in late 1700's. This historical home includes a large living room with original Rumford fireplace and beehive oven, five bedrooms (two with fireplaces and shared bath on main floor), three full baths and family room with cathedral ceiling. Two car garage. Property consists of 1.55 acres that include a second home that can be used for rental income or as a guest house.

Listing Courtesy of Raynard & Peirce Realty,LLC

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$
%
$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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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47 Spring Garden Waterbury CT 06708
Pending Continue to Show

MLS Number 170365336

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.19

Welcome to a place where all of your dreams can come true! Whether investing, buying a second home, or a place to live and love, this completely updated three bedroom Ranch awaits you, not for long! Situated on a private and quiet street, this home boasts a beautifully leveled yard, a spacious front porch for relaxing, and a lovely back patio perfect for entertaining and enjoying the warmer weather. Walk into your gorgeous living room complete with hardwood floors, recessed lighting, and plenty of natural light. The living room leads seamlessly into the large kitchen that features a breakfast bar, granite countertops, tile floors, and ample cabinet space. There is an open sightline from the living room all the way to the dining room which could also be utilized as a family room, making this house perfect for entertaining! The dining room is complete with a vaulted ceiling and conveniently walks out to your backyard oasis including a patio and a shed for those tools you want to keep stored. All three bedrooms feature hardwood floors, and are perfect for guests or if you need an in-home office. The updated full bathroom is located right next to all of the bedrooms and boasts a granite vanity and a full tub. Want more? You will be pleased to discover the updated lower level, so get ready to relax! This huge space can be used as a family room, exercise room, extra bedroom...the possibilities are endless! This also leads directly to a one car garage and large laundry/storage room.

Listing Courtesy of Keller Williams Prestige Prop.

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$
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$/month over payments
Federal 30-year interest rate: 3.02% last updated on Mar 4, 2021
* 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: 3.02% last updated on Mar 4, 2021
* 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.