The Matthews GroupWilliam Raveis

The Matthews Group

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.

28 Lake Drive South New Fairfield CT 06812
Open House

MLS Number 170408824

  • Single Family
  • Next Open House: Sun 08/1 1:00 pm. to 3:00 pm.
  • Square Feet 2,446
  • Bedrooms 4
  • Bathroom 4

Beautiful Western Exposure one of a kind waterfront in sought after Candlewood Isle! The house sits up high on the property providing lake views from almost every window! Just one easy step from the 2-car garage into the sun-filled foyer welcomes you into the home and the well equipped Kitchen. The main level Living Room/Dining Room has a cozy gas fireplace with an adjacent study/office with pocket doors for privacy. The house sports 4 bedrooms and 4 baths with a secluded Master Suite with gas fireplace and private balcony. The additional 3 bedrooms each have a full wall of windows facing the water that accommodate a comfortable sleeping space (one with its own private bath). Anderson Thermopane windows throughout including the 7 sliders on the enclosed porch which opened provide for the summer breeze as well as a passive solar feel when closed for extended 4 seasons use. A black topped driveway takes you down to a level grassy oversized yard that extends out to your own private point with 140 ft of shoreline providing 180-degree water views! The waterfront provides a floating dock, a stationary dock with boat lift, a dual floating jet ski dock, a waterside deck, sand beach patio, and an elevated patio with a shed that has electricity for refrigeration plus storage. Isle amenities: Clubhouse, protected swim & beach area, marina(slips available), lighted tennis & bocci courts, basketball court and summer kid's camp! Simply, the perfect year-round home or second home for all!!

Listing Courtesy of Keller Williams Realty

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%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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43 Gaylord Road New Milford CT 06755

MLS Number 170419757

  • Single Family
  • Square Feet 3,808
  • Bedrooms 4
  • Bathroom 5
  • Year Built 1725

Step back in time into this 18th Century Colonial - with its inherent charm and character - which has since been transformed into a beautiful, much-treasured 21st Century home. Thought to be only the second home ever built in Gaylordsville and the last house standing that was built by a Gaylord, the home has been lovingly updated and expanded by the owner who was born and raised here, and then raised a family of his own. A beautiful open plan chef's kitchen and large adjoining pantry anchor the main level, which also includes a spacious family room with an original fireplace - Dutch oven and swing arm in place. The main level also offers a window-lined den and dining room, a living room and a main level bedroom with full bath. On the upper level is a vaulted master bedroom with en suite bath, 3 walk-in closets and a Juliet balcony. There are three further bedrooms - all with hardwood floors - and a partially-finished lower level. Interior details include chestnut and random width flooring, chestnut beams, and original hardware. Situated on a perfectly level lot, the property includes a 2-car attached garage, a 2-car detached garage, a large backyard and an inviting in-ground heated swimming pool with adjacent cabana. Surrounded by historic homes on a quiet, handsome country road and walking distance to several preserved hiking trails over varied terrain. Just 90 minutes from Manhattan and 10 minutes each to Metro North trains and the towns of Kent, Sherman and New Milford.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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760 Lake Drive Winchester CT 06098

Winchester, CT760 Lake Drive

Price$735,000

Est. Mortgage: $/month

MLS Number 170414426

  • Single Family
  • Square Feet 838
  • Bedrooms 3
  • Bathroom 3
  • Year Built 1910

**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!! Town hall square footage does not include finished upper story.

Listing Courtesy of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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 Road Morris CT 06763

MLS Number 170380573

  • Single Family
  • Square Feet 4,500
  • Bedrooms 7
  • Bathroom 6
  • Year Built 2004

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: 2.78% last updated on Jul 22, 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

Price$575,000

Est. Mortgage: $/month

MLS Number 170373157

  • Single Family
  • Square Feet 1,169
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1850

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: 2.78% last updated on Jul 22, 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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457 North Street Norfolk CT 06058

MLS Number 170418713

  • Single Family
  • Square Feet 1,984
  • Bedrooms 4
  • Bathroom 3
  • Year Built 1893

Wonderful 1890s farmhouse in an excellent location with truly lovely property. There are 4 Bedrooms with 2 and a half baths and a roughed-in full bath off the master. The kitchen has a great old farm sink, wide-board wood flooring, a gas range and a double wall oven and an amazing soapstone wood stove. The dining room has plenty of space for a large table and is just off the kitchen. The living room is large and sunny. There is a study/den on the main level with built-in bookshelves. There are front and back stairs to the second floor. There is great space on the 3rd floor too. The exterior was professionally painted in the spring of 2021 and is in excellent condition. The house has 3 lovely porches from where one can relax and enjoy the pretty views of all the property. The driveway was recently re-done with two entrances to North Street. There is a detached 2 car garage/barn and a second lovely old barn. The land has fields, lawn, gardens and nice woods. This would be great for horses or animals, small farming, for a full-time home or a great weekend/vacation home. Norfolk was selected as Connecticut's best small town by Connecticut Magazine for the last 3 years in a row and is home to several state parks, loads of hiking trails and protected land, Tobey Pond for swimming, Yale Summer School of Music, Infinity Hall, an excellent library and so, so much more. This is a great home! Showing on the property will be allowed beginning Sunday, July 18th. Hurry!!!

Listing Courtesy of Locust Lane Realty LLC

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%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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50 Cornwall Road Warren CT 06754

Warren, CT50 Cornwall Road

Price$574,900

Est. Mortgage: $/month

MLS Number 170412029

  • Single Family
  • Square Feet 2,923
  • Bedrooms 3
  • Bathroom 4
  • Year Built 2005

Located in the desirable Litchfield Hills of Connecticut this light filled home with central air conditioning is in mint condition and located on 2 acres with a natural spring fed pond. The wood burning fieldstone fireplace, hardwood floor, and vaulted ceiling are highlights of the living room. A spacious kitchen includes plentiful cabinetry, breakfast bar, and stainless steel appliances including a gas stove. The dining area has French doors opening to a delightful sunroom with views of the yard and pond, and a Trex deck. This lovely home has 2 bedrooms and 2 full bathrooms conveniently located on the 1st floor. A 3rd bedroom with a wall of closets and a full bath is on the second floor. The large family room with radiant heat and a half bathroom are located on the lower level which leads to the patio. An oversized attached 2 car garage has cabinetry and radiant heat. You'll find it easy to relax by the pond, deck, porch, or patio. The house is wired for a generator and plumbed for a central vacuum. This meticulously maintained home is on the market for the first time and is perfect as a primary or second home. An added plus is the Warren town Beach on beautiful Lake Waramaug, the second largest fresh water lake in Connecticut. Located only 85 miles from Manhattan and with nearby Metro North train stations heading to points south you'll find it's a great place to live!

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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 Lake Avenue Danbury CT 06810

Danbury, CT26 Lake Avenue

Price$499,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170412282

  • Multi Family Multi-Family For Sale
  • Square Feet 1,000
  • Bedrooms 8
  • Bathroom 4
  • Year Built 1938

This Very Unique Property Consists of 2 Adjacent Lots Containing 1 Multi-Family House, One Single Family House, Plus Out Buildings Under One Deed. The Property is Being Sold As One Parcel. The Lot Size is .61 Acres of Lovely Level Yard, with Open Area Between the Houses and Continuing Past the Second Home to Crofut Place. The Front Two Family Home has a Welcoming Front Porch and Two Apartments, Each with Two Bedrooms and a Full Bathroom. Both have their own Rear Porch too! The Second House has a Nice Spacious Main Level with Kitchen, Dining Room & Living Room and Four Bedrooms & 1 1/2 Baths, and a Screened In Porch. There is a Two Car Detached Garage and a One Car Free Standing Garage As Well. Plenty of Parking Here. The Yard is Beautifully Maintained As You Can See by the Sprawling Grass Areas. There is also a Cool Stone Built BBQ area for Seasonal Fun/Outdoor Enjoyment. The Houses need Some Updating but are Built Well, with their Foundations of Stone and Concrete. Showings Must Be Coordinated with Listing Agent. Highest & Best is Due by Monday, June 28, at 5:00 P.M.

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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72 Alpine Circle Newtown CT 06482
Pending Continue to Show

MLS Number 170414601

  • Single Family
  • Square Feet 1,176
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1955

Need a Peaceful Retreat, Second Home, Privacy, Peace & Tranquility in a water community? Looking to downsize or purchase your 1st home? No Need to look any further! Escape to the Lake! Just imagine owning your own bit of paradise in this charming 1176 sq ft Ranch with open concept/living/dining/kitchen with 2 cozy bedrms, double closets, ceiling fans, updated remodeled bathrm & separate private home office. Home makes for a perfect summer get a away, but is fully heated which makes it just as perfect for year round living. Lake Zoar Beach Club is a walk away & provides lots of amenities ($80.00 per year-not mandatory) fishing, boating, water sports or a cool refreshing swim on those hot days of summer. As you enter your New Home & Step onto Hardwood flrs, you immediately notice a Beautifully Sun Lite Family Rm that open to a Fabulous Kitchen with walk in pantry (Newer Stove & Refrigerator) & Entire back Kitchen Wall covered with Cultured Stone that surrounds a Gorgeous Stone Gas Fireplace. "Did I forget to mention, home has Newer Roof & Furnace & C/Air have been well-maintained & professionally serviced yearly. Plenty of parking on this .23 acre property. Detached one car garage & plenty of private off street parking. For an amazingly affordable price...Needs a little TLC. Whether you're downsizing, retiring or investing in that rental property you've always wanted. This is it!

Listing Courtesy of Coldwell Banker Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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4 Cedar Lane Barkhamsted CT 06063

Barkhamsted, CT4 Cedar Lane

Price$199,000

Est. Mortgage: $/month

MLS Number 170408461

  • Single Family
  • Square Feet 742
  • Bedrooms 2
  • Bathroom 1
  • Year Built 1957

Escape from the world! This cozy retreat in the woods is a minutes walk to pristine West Hill Lake and around the corner from the West Hill boat launch. 4 Cedar Lane is a totally remodeled cabin/cottage that can be enjoyed year round and offers a serene atmosphere on a private road. Quite the package here! Upgrades all done within the last few years and include the following: standing seam metal roof, vinyl siding, all new plumbing (new ABS wastelines and PEX waterlines), complete electrical upgrade (all wiring boxes and devices replaced with a complete panel upgrade), the private well has new pump and expansion tank, waterproof luxury vinyl flooring throughout, quality steel entry doors and energy star Harvey classic windows. Designed with a rustic mix of wood and cedar throughout with clean, neutral colors. Nature abounds as you step out onto the private two tier deck overlooking acres of woods to explore and enjoy. Whether you like to fish, boat, kayak, swim or just enjoy the most nature has to offer, this remodeled cabin can be your vacation home all year around. Property being sold As Is. Call today for your private showing!

Listing Courtesy of Realty Executives Capitol Reg.

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$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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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342 Jackson Street Thomaston CT 06787

Thomaston, CT342 Jackson Street

Price$187,900

Est. Mortgage: $/month

MLS Number 170402281

  • Single Family
  • Square Feet 1,478
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1972

Unique opportunity available in a quiet private country setting! One acre property has two separate smaller homes that have been with the current owners for the past 34 years. First home is a two bedroom cape with one bathroom all on the first floor. Very clean and cozy! The second home is a ranch, under 700 square feet with one bedroom and one bathroom and is currently rented. New well pump in 2015 and septic is serviced annually. Separate utilities for each home. Great starter home or those downsizing or real estate investors! Bring your offers as soon as possible because this will not last!

Listing Courtesy of Coldwell Banker Premier Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

342 Jackson Street Thomaston CT 06787

Thomaston, CT342 Jackson Street

Price$187,900

Est. Mortgage: $/month

MLS Number 170405339

  • Multi Family Multi-Family For Sale
  • Square Feet 1,478
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1972

Unique opportunity available in a quiet private country setting! One acre property has two separate smaller homes that have been with the current owners for the past 34 years. First home is a two bedroom cape with one bathroom all on the first floor. Very clean and cozy! The second home is a ranch, under 700 square feet with one bedroom and one bathroom and is currently rented. New well pump in 2015 and septic is serviced annually. Separate utilities for each home. Great starter home or those downsizing or real estate investors! Bring your offers as soon as possible because this will not last!

Listing Courtesy of Coldwell Banker Premier Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.78% last updated on Jul 22, 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.

Save FavoriteSchedule TourAsk A QuestionMore Details

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2021 SmartMLS, Inc.