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.

10 Gatehouse New Milford CT 06776
Open House

MLS Number 170393492

  • Single Family
  • Next Open House: Sun 05/16 12:00 pm. to 2:00 pm.
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 5

Tucked away on a quiet cul de sac in a sought after town of Litchfield County, This stunning 5 bedroom/4.5 bath estate-like colonial will leave you in awe offering carefully designed spaces that achieve the perfect harmony between comfort, luxury, work and play for every generation. The sweeping views abound the most discerning homeowner - acres of green level lawns, private walking trails and lake access - simply your own oasis. The classic fa├žade draws you into the sprawling 4,550 sqft. builder's home. The attention to detail is noticeable from the minute you enter the home - some highlights include high ceilings, hardwood floors and custom mill work. The large Chef's kitchen offers stainless steel appliances and custom cabinetry. The adjacent family room is perfect for entertainment and features a floor to ceiling Fieldstone fireplace. The main level also boasts an impressive master suite that would be ideal for an in-law setup as well as a large office with oversized closet that can easily accommodate a work station. Upstairs, you will find the additional bedrooms and the second large master suite that is simply unmatched with great closet space, a sitting area and a bonus room that could easily become a second home office. If that isn't enough, there are two laundry rooms and the partially finished lower level is a walk-out with endless possibilities that can be suited for today's new norm whether you need your own class room at home or an alternative in-law suite.

Listing Courtesy of Compass Connecticut, LLC

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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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116 East Shore Washington CT 06777
Pending Continue to Show

MLS Number 170386816

  • Single Family
  • Property Style Cottage
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.46

Rare opportunity to own on beautiful Lake Waramaug. This bright and spacious lake front cottage (just under 2500 sq ft) is ready for you to call home, or serve as an unbelievable summer destination. Complete with its own cabana and amazing beach front pier which includes a large area for entertainment. Inside there are 6 skylights that will brighten any day! The cathedral ceilings add to the openness of the home. The stone fireplace is a great spot to curl up to a book in the winter months. Enjoy breakfast at the breakfast bar overlooking the lake or take your coffee to the screened in porch for even more breath taking views. The master bedroom is spacious and and not only does it have views of the lake, there is a babbling brook that will help put your mind at ease to catch those perfect ZZZ's. The other bedrooms are spacious and both have their own balcony with amazing lake views. The Pinnacle trail access is a short walk from the home as well! Nothing better than a Lake House with a mountain feel! If you are looking for a Lake front home where you can build lasting memories, then look no further than 116 E Shore Rd! Build a second home, guest house or preserve your privacy with the purchase of the 31 June Road building lot. Nearly 1000 feet of lakefront with both lots. Located in the highly coveted Region 12 School District.

Listing Courtesy of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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

MLS Number 170380573

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

Outstanding Opportunity with Two 2004 Build Homes on over 3 Acres in Morris. Live in One House and Rent the Other to Live Free or Rent Both for Great Investment! One house has 4 bedrooms and 2 and 1/2 baths with eat in kitchen, formal dining room, fireplaced living room, office, and laundry rrom on main level with hardwood floors throughout. Brand new kitchen with stainless steel appliances. Large bedrooms with plenty of closet space. Master bathroom and bath with jet-tub and shower. Sliders off of family room lead to deck, large lot and huge shed. Basement is finished mother-daughter with an additional kitchen, bath, bedrooms, and living room, and direct access to 2 car garage. The second home has 2 huge bedrooms with master baths, beautiful, new eat in kitchen, formal dining room, and big fireplaced living room. Possibility to finished mother-daughter in basement area with direct access to one car garage. Best Investment Value for Owner Occupied Opportunity with over 4,500 sqft Total. Call before someone else gets it!

Listing Courtesy of Heflin Group Realty

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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: 2.94% last updated on May 13, 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: 2.94% last updated on May 13, 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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26 Craigemore Avon CT 06001

Avon, CT26 Craigemore Circle

Price$406,000

Est. Mortgage: $/month

MLS Number 170387359

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 0.69

This supremely constructed home sits kitty corner on a flat lot. Four (4) bedroom, 2 full & 2 half bath traditional center hall colonial home. Hardwood floors throughout, except for kitchen and entry hall. Super location: great for walks and bikes, quiet yet close to shopping, and pool club down the street. Front to back sunny living room with fireplace and dining room are accented with dental molding. Great den with pretty bay window. Kitchen is set to go with brand new oven and great breakfast nook! The laundry, mudroom and handy office are accessible from separate entrance - good for a home business. Main floor: kitchen, dining room, large living room with fireplace, den, hall closet, 1/2 bath, laundry room with half bath, second home office, 2 car garage. Upper floor: master bedroom suite with attached bath and walk-in closet, additional three bedrooms (all good size), hall closet, full bath. The lower level includes 20-foot shuffle board table for Covid-compliant parties.

Listing Courtesy of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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: 2.94% last updated on May 13, 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$314,900

Est. Mortgage: $/month

MLS Number 170384465

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

Turn key property with 2 homes on 1 lot! Great for family with in-laws or investors to rent and get excellent cash flow! 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 with roofs less then 1 year old. 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. Both homes remodeled w/ brand new features, take advantage of this unique opportunity!

Listing Courtesy of Showcase Realty, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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
Pending Continue to Show

MLS Number 170349132

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 3
  • Acreage 1.55

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: 2.94% last updated on May 13, 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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230 Boyd Winchester CT 06098
Open House

MLS Number 170396443

  • Single Family
  • Next Open House: Sun 05/16 10:00 am. to 12:00 pm.
  • Property Style Colonial
  • Bedrooms 3
  • Bathroom 2

Great opportunity to be steps from Highland Lake! This 3 bed, 2 full bath home is moderately updated. Will make a great main residence, second home or investment. Walk to public boat launch/ lakefront. Beautiful lakeview from the front of the house. Antique charm, 3 spacious bedrooms, a large enclosed & heated porch, updated kitchen and baths and new roof in 2020 are some of the features of this home. As-is. Will qualify for FHA.

Listing Courtesy of Tier 1 Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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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14 Aquatic Barkhamsted CT 06063
Pending Continue to Show

MLS Number 170392777

  • Single Family
  • Property Style Cottage
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.12

Welcome to West Hill Lake! If you're looking for a summer vacation home or a weekend getaway, this cottage is for you! Enjoy years of mini vacations, even when traveling isn't an option. Cute as a button and right across the street from the lake, all you need to do is bring your towels. Enjoy live music every weekend at the North End Store from the privacy of your oversized back deck. With updated electrical, a brand new septic, and 7 tons of new gravel for the driveway, you'll have nothing to do except personalize your new oasis. This cottage comes with beach rights to the private LAPOA beach where you can enjoy the sun, the sand, and the clean, spring-fed lake water. Book your private showing today! You won't find a better value and this cottage won't last long!

Listing Courtesy of Berkshire Hathaway NE Prop.

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.94% last updated on May 13, 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 2021 Smart MLS, Inc. All rights reserved.