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.

204 Long Ridge Road Danbury CT 06810

MLS Number 170440434

  • Single Family
  • Square Feet 5,128
  • Bathroom 3
  • Property Style Colonial, Ranch
  • Year Built 1952

A truly unique and amazing property to make wonderful memories. A 2 Bedroom, 2 Bath Colonial Home and a 2 Bedroom, 1 Bath Ranch Home, blended into one very special home. The first home is a 2 Bedroom, 2 Bath Colonial, built in 2003. Kitchen with Granite, Custom Cabinetry, and Island installed in 2017. Dining Room with Pellet Stove and Sliders to a Wrapround Deck with Awning. Living Room with Hardwood. Loft above Living Room. Master Bedroom Suite with Sitting Area, Hardwood Floor, French Doors to Wraparound Deck, Office, Walk-in Closet, and Master Bath with Jacuzzi, Shower and Marble Floor. Central Air. The second home is a 2 Bedroom, 1 Bath Ranch, built in 1952. It was lovingly remodeled in 2016. Updated Kitchen with Gas Stove, Double Sink, Huge Pantry, Breakfast Bar and Pergo Floor. The Living Room has a fireplace, and Knotty Pine Built-ins. Enclosed Porch, Dining Room, Mudroom, and Deck. All New Windows, Carpeted Hardwood Floors, and Central Air. Full Basement. Generator Hookup runs the entire home. Both homes have their own Laundry Room. 4 Heating Zones. 3 Currently being used. Beautiful 1.36 acres of property. 3 Car Garage, with one bay being a finished room with Bar and Separate Zone for Heating/Cooling. Storage located in the front of the 2 Bays of the Garage. Charming Shed with Basement. 5 Bedroom Septic, Well and Roof 2003. A short distance to West Redding Train Station, Shopping, and Restaurants, yet this inviting home offers privacy and serenity. A great location.

Listing Courtesy of Coldwell Banker Realty

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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: 3.05% last updated on Oct 14, 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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102-A Chambers Road Danbury CT 06811

Danbury, CT102-A Chambers Road

Price$649,921

Est. Mortgage: $/month

Open House

MLS Number 170443809

  • Single Family
  • Next Open House: Sun 10/17 12:00 pm. to 2:00 pm.
  • Square Feet 3,408
  • Year Built 1988
  • Bedrooms 4

Welcome to your PRIVATE RETREAT! This expansive Cape/Colonial home is nestled back from the road and sits on 2+ acres of flat property backing to green space for added protection and privacy. Just a quick hour's drive outside of Manhattan, this is an ideal second home, weekend reprise or primary residence just waiting for your special touch. The floor plan of this home offers great spaces for everyday living and/or entertaining, Your summers will be filled with relaxing afternoons by the pool, dining al-fresco on the deck or sitting around the fire pit with family & friends. When the weather cools you can take comfort cozying up by the fireplace or watching Sunday football in the spacious family room that adjoins the eat-in kitchen. A home office/library with a FP and french doors to the front covered porch makes working from home a delight. The formal DR is large enough to host large holiday gatherings too. A bonus room makes an deal space for a play/rec room and the walkout LL offers expansion possibilities. Upstairs is an enormous master suite with a separate sitting room, full bath and walk in closet. Three addtl' bedrooms and a full hall bath complete the UL. 2 car garage with main level entry for added convenience. Close proximity to I-84/I-684, Danbury schools, shopping, restaurants, Richter Park golf course and walking distance to the Upper Kohanza Reservoir and trails. Not To Be Missed. COME MAKE IT YOURS!

Listing Courtesy of Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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
Open House

MLS Number 170380573

  • Single Family
  • Next Open House: Sun 10/17 2:00 pm. to 5:00 pm.
  • Square Feet 4,500
  • Bedrooms 7
  • Bathroom 6

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: 3.05% last updated on Oct 14, 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 Valley Field Road South Newtown CT 06470

MLS Number 170411336

  • Single Family
  • Square Feet 2,056
  • Bedrooms 3
  • Bathroom 2
  • Year Built 1938

Welcome Autumn! Treat Yourself to the Quintessential New England Lifestyle in a Storybook Setting… Escape to this gracious cottage-style vintage colonial on over 8 magnificent acres in a bucolic country setting, complete w/ glistening pond & rowboat! Original 1938 build completely renovated w/ addition in 2000. Looking for that special "Second Home First"? This charming year-round or weekend country home is just 90 mins. from Manhattan and perfect for lazy summer days or fabulous entertaining on the stone terrace! Relax to the tranquil sounds of nature from the master balcony overlooking the water. Lush manicured landscaping, irrigation system, colorful perennials and rambling stone walls! Whether you're the chef or simply enjoy a great meal with friends and family - you'll love this stunning new (2021) kitchen with sleek quartz counters and stainless appliances! This home offers the perfect layout for the new necessity of "together, but separate" living spaces! Hardwood throughout; French doors; nooks & crannies! Updated baths. Freshly painted inside and out! Stroll down the quiet country lane. Retreat to the cozy double-sided fireplace during the cooler nights, and delight in an old fashioned ice skating party during the winter months! Pristine and meticulously maintained. Plenty of parking space in private driveway. Just minutes to highway, great restaurants and shopping, tennis courts, parks and community pool/rec center. Unwind & Discover the Charm that is Newtown!

Listing Courtesy of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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18 South Main Street Kent CT 06757

Kent, CT18 South Main Street

Price$357,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170433310

  • Single Family
  • Square Feet 1,420
  • Bedrooms 4
  • Bathroom 2
  • Year Built 1840

This Renovated 1840 home is located in the Kent village center! Filled with charm this 8 room home has hardwood floors, quartz countertops and stainless steel appliances in the kitchen, first floor laundry, 4 bedrooms, 1 1/2 baths, covered porch, full unfinished basement, detached garage, level yard, and has public water and sewer. Located in the commercial zone of town there are countless opportunities for this property. It is perfect as a full time residence, second home, and in-home occupation. Currently used as a B&B. And it's so convenient to restaurants, boutiques, private schools, art galleries, and stores! You'll discover lakes, hiking trails, biking, kayaking, fishing, skiing at Mohawk Mountain, and professional NSCAR racing at nearby Lime Rock Park. Located approximately 85 miles from Manhattan and only 20 minutes from a Metro North station with trains to Grand Central station. You'll find Kent a great place to live!

Listing Courtesy of William Pitt Sotheby's Int'l

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$
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$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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 White Road Litchfield CT 06778

MLS Number 170443224

  • Single Family
  • Square Feet 960
  • Year Built 1950
  • Bedrooms 2
  • Property Style Ranch

WOW! What a stunning transformation this adorable Ranch in the Northfield section of Litchfield has gone through! Taken down to the studs, this home has been REMODELED from the roof down! Within the past 2 years the work completed is: New Roof, New Windows, New Pergo Outlast Waterproof Flooring, New Natural Beams (spanning the entire LR & Kitchen), reimagined Living Room w/Vaulted Ceiling, reconfiguration of the Bedrooms, including the Primary that can fit a King Sized Bed! Remodeled Eat-In-Kitchen w/Center Island, Granite Countertops & Full Bath w/tub & shower, New Insulation & Sheetrock, Split system for heating & cooling (4 splits) w/heat pump, New Well Tank & New Septic Tank. This open floor plan concept makes you feel like you're on vacation all the time starting from the blue stone fireplace in the LR for those cool fall evenings, water view of Northfield Pond (public access) to the smooth & easy flow into the EIK w/all the storage you'll need in the soft close custom cabinets & drawers. There's 2 choices of laundry area, either in the pantry (stackable) or in the Full Basement w/hybrid electric Rheem HW heater & Garage. Perfect starter home or downsize w/distinction. Minutes to all shopping, dining, Rts 254, 6 & 8 yet in a charming Country setting on a quiet & peaceful street. Looking for a weekend retreat/vacation home?? This is it! Pack your bags and move right in! Schedule your showing today to see the fall foliage & be settled by the Holidays! Only 2 HRS from NYC!

Listing Courtesy of Showcase Realty,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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19 A Old Creamery Road Colebrook CT 06021

Colebrook, CT19 A Old Creamery Road

Price$269,450

Est. Mortgage: $/month

MLS Number 170427154

  • Single Family
  • Square Feet 1,296
  • Bedrooms 3
  • Property Style Cape Cod
  • Bathroom 2

Price reduced in Litchfield County! Low taxes, a huge private flat back yard, stone walls, a main floor bedroom, hardwood floors and and move in ready are just a few of the features of this Northwest Corner 3 bedroom 2 bath cape. Pride of ownership is on display with this well maintained beautifully landscaped home with a two car garage that sits back from the main road. Install a pool, build a playscape, the possibilities are endless. Would make a great second home as well. Nearby enjoy the Colebrook river, lake and dam, Norbrook Farm Brewery. Highland lake, Algonquin State Forest just minutes away. 30 min from Torrington, 2 hours from NYC and Boston. Sits on the Winsted side of Colebrook. Minutes from Town Center shops and restaurants.

Listing Courtesy of Turning Point Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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1067 Lakeside Road Southbury CT 06488

Southbury, CT1067 Lakeside Road

Price$255,000

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170443645

  • Single Family
  • Square Feet 1,002
  • Year Built 1961
  • Bathroom 1
  • Bedrooms 2

RENOVATED 2-BEDROOM RANCH IN A LAKE COMMUNITY. Living room w/ working fireplace. 2 bedrooms, one w/ barn door. Modern kitchen with stone countertops, s/s appliances & kitchen island. Separate laundry room with washer & dryer. 1,002 sq.ft., with additional 174 sq.ft. Screened-in porch. Detached 283 sq.ft. one-car garage. Additional 524 sq.ft. basement for storage. New windows with efficient double paned low-e glass with argon gas. New solid doors and hardware. Hardwood floors in living room and one bedroom. NEW septic system & public water. Updated plumbing and electric. Serene backyard with stone walls & also usable front & side yards. Detached garage for car or storage plus driveway can accomoodate 3 additional cars. Water enthusiasts with love living in this Lake community. Lake Zoar is walking distance and public boat launch is 3 mins away. Perfect starter home in Region 15 school district or second home for fun weekends in Connecticut.

Listing Courtesy of Gina Jacobs Real Estate & Property Management

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$
%
$/month over payments
Federal 30-year interest rate: 3.05% last updated on Oct 14, 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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