The Matthews TeamWilliam Raveis

The Matthews Team

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 Team with any questions about buying a vacation home or to schedule a private viewing. You may also be interested in browsing lake homes.

4 Cider Mill Road Newtown CT 06482
Pending Continue to Show

MLS Number 170454972

  • Single Family
  • Square Feet 4,900
  • Property Style Colonial
  • Year Built 2003
  • Bathroom 5

This is the dream home you have been waiting for! Welcome to this meticulously maintained 4 Bedroom Colonial situated on a cul de sac with impressive and expansive sunset views. An entertainer's dream - this home features a butler's pantry, one of a kind patio and outdoor kitchen. The main level is full of wonderful surprises such as a dedicated home office with built ins, recently renovated laundry room and a bonus room with skylights - currently being used as a playroom - that is perfect for a second home office. The gourmet kitchen features stainless steel and Subzero appliances, granite countertops, a walk in pantry and an eat in area. The oversized great room impresses all with its abundance of light, vaulted ceilings, and both a pellet stove and wood burning fireplace. Take the grand staircase to the second level to be greeted by 2 bedrooms, a Jack and Jill bathroom, and a guest suite. Around the corner, you will find the Primary Bedroom Suite complete with a sitting area, his and hers closets and vanities, and a jacuzzi tub. The lower level of this home offers additional living space, kitchenette an oversized mudroom and attached garage access. Schedule your showing before this home is SOLD!

Listing Courtesy of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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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13A Osborn Road Sherman CT 06784

Sherman, CT13A Osborn Road

Price$750,000

Est. Mortgage: $/month

MLS Number 170453986

  • Single Family
  • Square Feet 2,400
  • Property Style Contemporary, Ranch
  • Bedrooms 3
  • Year Built 2022

Custom built contemporary ranch + breathtaking views = YOUR DREAM HOME! This 'to be built' home has direct western exposure capturing sunsets all year long with stunning views to NY. The driveway, front and side of the home are mostly level and the rear slopes capturing the most beautiful sunset views. Don't miss this beautiful 2400+/- square foot home with 3 bedrooms, 2 full and 2 half baths, with walk-up attic spacious enough for future bonus room, partially finished lower level and so much more. Interested in one level living? You can have it here with a two car attached main level garage. High efficiency propane heating and cooling, this home is energy efficient and will keep your costs low year round. To be built by one of the area's finest construction and design teams. If you act fast, you will have the opportunity to customize your finishes with the firms highly accredited lead interior designer! Construction to begin Spring of 2022 and completion is anticipated for Fall 2022. Only 70 miles from NYC, this is the perfect second home or primary residence. Enjoy country, vacation living at its' finest. Schedule your showing today!

Listing Courtesy of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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: 3.56% last updated on Jan 20, 2022
* 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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145 Bentley Circle Goshen CT 06756

MLS Number 170444887

  • Single Family
  • Square Feet 4,318
  • Bedrooms 4
  • Property Style Other
  • Bathroom 4

This Woodridge Lake Craftsman style home offers family style living at it's best. High ceilings, lots of light through the windows and multiple French floors make this a perfect year round or vacation home. Hardwood and tile floors are located throughout the main floor. The kitchen offers granite and Corian style countesr and features stainless steel appliances and hardwood cabinetry. The home has a central vacuum, A/C, oil heat on the main two levels. The master en-suite has a separate tub and steam shower. All bedrooms on the second floor have carpeting and some with ceiling fans. There is a screened in porch off the breakfast area which leads onto the main deck. The master bedroom has a private deck as one passes through the French doors. Lawn and grass area have plenty of room to play or to garden. A stone wall lines one edge of the property. A hot tub is at ground level and offers a retreat from the ordinary. The lower level of this home is finished and includes a full bath and fireplace stove.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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 Washington Road Woodbury CT 06798

Woodbury, CT72 Washington Road

Price$102,999

Est. Mortgage: $/month

MLS Number 170447761

  • Condo
  • Square Feet 544
  • Property Style Ranch, Studio Apt
  • Year Built 1965
  • Bathroom 1

Owner/Agent is looking to sell now! Priced to sell! An easy level stroll from parking to this immaculate, move-in-ready condo. Are you just starting out or scaling down? Have you been leasing and want to have a place of your own? Its an opportune time to take advantage of low interest rates. You can purchase and own for less than most area rentals. You might also consider purchasing a unique quaint and affordable, second home escape... so many scenarios that could provide a perfect fit for you! Close to Town with easy sidewalk access, goods and services. A commute to I-84 is a breeze! The condo has a picturesque, level yard area. A stack washer and dryer is included for your convenience. Per The condo association, there is mandatory dryer vent cleaning each autumn. The dryer-vent was cleaned out for the current year. Plan your visit to quintessential Woodbury soon. Visit Flanders Nature Center, Hollow Park, Boutiques, garden centers, gift and antique shops. Woodbury features numerous award winning restaurants, many featuring farm to table cuisine.

Listing Courtesy of Adams & Adams Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.56% last updated on Jan 20, 2022
* 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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