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.

59 Ore Hill Salisbury CT 06039

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 3 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: 2.72% last updated on Nov 25, 2020
* 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 Winchester CT 06098

Winchester, CT760 Lake Drive

Price$739,900

Est. Mortgage: $/month

MLS Number 170328177

  • Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.12
  • Square Feet 1,764

**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!!

Listing Courtesy of Northwest CT Realty

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$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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680-B Mountain Torrington CT 06790

Torrington, CT680-B Mountain Road

Price$729,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170296067

  • Single Family
  • Property Style Ranch
  • Bedrooms 2
  • Bathroom 1
  • Acreage 113.8

INDIAN LOOKOUT Historic site with expansive breathtaking views on over 113 acres +/- offering crisp clean air and making an ideal weekend retreat, second home, or year-round living. The charming 1946 brick country ranch is sited at the top point of the property offering eastern and western mountain views of Litchfield county for miles. The entire parcel is comprised of seven separate parcels. Abundant wildlife is everywhere with trails and plenty of room for horses and or farm animals (as there are outbuildings) and gardens and additional building sites with views and privacy. Buyers must have pre-approval before showing.

Listing Courtesy of Elyse Harney Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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5 Garland Washington CT 06777

MLS Number 170353362

  • Single Family
  • Property Style Colonial, Modern
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1.2

This Litchfield Hills compound has two homes and is perfect for a work-from-home scenario, a large family, or for additional rental income. The home most predominantly featured in the photographs is a remodeled Mid-Century modern home with 20 foot ceilings, abundant natural and North light (previously a painters studio) Well equipped with a cozy fireplace, barn board paneling, an open floor plan consisting of a large bedroom and 3 separate lofts for guest overflow and additional utility. The second home is a remodeled antique farmhouse comprised of 9 rooms, 3 bedrooms, 3 full baths, and an open floor plan featuring exposed hand-hewn beams, stone fireplace, remodeled farmhouse kitchen with soapstone counters and sink, and stainless steel appliances. This home is equipped with a newer oil fired heating system and new water heater for more efficient utility bills. Multiple covered porches, decks, and stone terraces framed with perennial flowers and stone walls. An additional detached carriage house accommodates two cars or is suitable for a workshop or art studio. Short stroll to Mount Tom State Park for hiking, swimming, fishing, boating etc. Very proximate to Washington Montessori, Rumsey Hall, Community table, Bantam Market. Home ownership provides access to town beach at Lake Waramaug. Previous residence of actress Mary Pickford. Listing agent is related to owner. First showing restricted to Mid-century home.

Listing Courtesy of William Pitt Sotheby's Int'l

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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: 2.72% last updated on Nov 25, 2020
* 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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37 Curtiss Woodbury CT 06798

Woodbury, CT37 Curtiss Meadows

Price$555,000

Est. Mortgage: $/month

MLS Number 170340055

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 1.85

Seriously like new condition! Exceptionally maintained. Private Colonial at the end of a quiet cul de sac neighborhood within minutes to Southbury and Woodbury town centers. The large eat in kitchen was remodeled with a center island with preparation sink, a breakfast peninsula, garden window, huge pantry and bright eat in area. Granite and Stainless, gas range/oven, dishwasher and microwave 2 years new. French door to recently installed 40x16 granite patio and stone wall surround. The family room has a welcoming propane fireplace w beautiful mantel and tumbled brick front, 12' ceilings, and hardwood flooring. 9' ceilings thru out balance of first floor and hardwood in all but kitchen. (re finished in 2018) Large formal dining room will nicely accommodate the upcoming seasons gatherings. Glass French doors are a beautiful touch. Formal living room is currently being used as second home office/den and there is an additional office off the kitchen with another garden window and a full bath. Bedrooms are all generous in size, master has double doors to full bath w shower and whirlpool in separate areas, double sinks, great use of space. One bedroom has direct access to 2nd full bath. Full laundry room on second floor. House was freshly painted 2 years ago. Three car garage with workbench and storage space. Full basement with high ceilings. Amazing sunsets and fall foliage views. Improved landscaping and irrigation system keep this lawn lush all season.

Listing Courtesy of Drakeley Real Estate, Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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21 Bruce Avon CT 06001

Avon, CT21 Bruce Lane

Price$449,900

Est. Mortgage: $/month

Pending Continue to Show

MLS Number 170351757

  • Single Family
  • Property Style Colonial
  • Bedrooms 5
  • Bathroom 5
  • Acreage 1.25

Make this YOUR OWN hidden retreat! Large estate located at the end of a cul-de-sac on a quiet street that is conveniently located to Route 44. This spacious colonial is move in ready! The main floor of this home offers an updated eat-in kitchen with stainless steel appliances and granite counters, a formal dining-room and formal living-room, a cozy family room with wood paneled walls, a 4-season porch AND an office that can be used as a first-floor bedroom. On the upper level the master-suite offers vaulted ceilings, a wood burning fire place and master bath. There are three additional oversized bedrooms and two full bathrooms on the second floor. If you're in need of even more space, then head on down to the lower level where you will find a large playroom with fire place, an additional bedroom with full bath and a flex room that was previously used as a second home office. Once you venture outside, you can enjoy an oversized level yard that offers all the privacy that one can want. A short walk will lead you to a secondary outdoor space that includes a fenced in pool area. Delight in some summer fun hosting cookouts with your friends and family or kick back and relax in the private gazebo overlooking the pool. Don't wait, call today to schedule your private showing.

Listing Courtesy of Coldwell Banker Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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250 Hunter Litchfield CT 06759
Pending Continue to Show

MLS Number 170341534

  • Condo
  • Property Style Townhouse
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,943

Majestically set into 77 wooded acres in the historic town of Litchfield, Hunters Chase is one of a kind private resort style community in the Northwest Hills. Exceptional Churchill unit constructed with the finest materials and upgrades . New to the market! Featuring a delightful chef's kitchen with farmers sink, Carrera marble countertops, Wolf gas range, Viking microwave, Subzero refrigerator, and wine cooler, ASKO dishwasher. Private composite deck off kitchen that faces the treed conservation area. Open floor plan with wood floors; dining room off kitchen as well as the living room with gas fireplace and built-in cabinets; Powder room and access to 2 car garage. Second level also with 9 ft ceilings, 3 bedrooms and 2 full baths with double sinks, including luxury master bath off master bedroom with double sinks, jacuzzi and separate shower; atrium ceiling and large walk in closet. Laundry area on 2nd level. Finished walk out lower level to patio and privacy! Lower level has 10 ft ceilings, carpeted, full bath and storage/mechanical room. Mechanical features, 3 zone central air and heat, security system. Amenities include a beautiful community clubhouse with social hall, kitchen and bar. Elevator and stairway to lower level with fitness center, aerobic and strength training equipment, locker room with showers, outdoor inground heated pool and patio. Basket ball court and private roads for running, bicycling and walking. Full time or second home! Agent/Owner

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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66 Kent Cornwall CT 06754

MLS Number 170319813

  • Single Family
  • Property Style Saltbox
  • Bedrooms 3
  • Bathroom 3
  • Acreage 1.5

Beautiful 3 bedroom New England Saltbox has seasonal views of Housatonic River. Open floor plan takes you from updated kitchen with stainless appliances, granite counters, sweet breakfast nook to large family room with sliders to deck overlooking lovely landscaped yard. Sit and relax by the fire in either fireplace on these crisp Fall evenings. Great year round or vacation home. Generator ready with 2 car attached garage. Price recently reduced, sellers are relocating. Minutes from Mohawk Ski Area, Appalachian Trail, Town Beach, Restaurants and Shops.

Listing Courtesy of Integrity Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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

MLS Number 170349132

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

Spacious Antique home built in late 1700's. Home includes large living room with fireplace, 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 which is currently rented to a long term tenant.

Listing Courtesy of Raynard & Peirce Realty,LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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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706 West Wakefield Winchester CT 06098

MLS Number 170353941

  • Single Family
  • Property Style Cottage
  • Bedrooms 2
  • Bathroom 1
  • Acreage 0.09

Rarely available cottage with 50' of waterfront on Highland Lake. This 2 bedroom, 1 bath home is the perfect 3 season retreat with many features: Main level consisting of large entry way, bedroom, bathroom and living room with brick fireplace and access to a large screened porch with beautiful views of the lake. Upstairs there is a loft bedroom that comfortably fits 2 beds. On the lower level you will find an eat-in kitchen with access to another large porch with amazing water views. New roof, new siding and backyard area with access to your private dock completes this vacation home.

Listing Courtesy of Century 21 AllPoints Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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 Kenyon Morris CT 06758

Morris, CT102 Kenyon Road, Lakeside

Price$235,000

Est. Mortgage: $/month

MLS Number 170344077

  • Single Family
  • Property Style Ranch
  • Bedrooms 3
  • Bathroom 2
  • Acreage 2.4

Charming rustic ranch surrounded in nature and privacy, (2.4 acres) awaits you in the Lakeside section of Morris. Every window looks out to your private yard to enjoy the changing seasons. You'll feel like you have escaped to Vermont once you enter the LR/DR with it's cathedral wood ceiling, hardwood floors, wood-burning fireplace and wood paneling adding to the cozy charm. This 3 bedroom, 2 bath home with separate mud / utility room makes this place a great starter home, downsizer or second vacation home! Owner is using one bedroom as a den. Recent owner improvements included: 2019 updated electrical service, 2019 new septic system, all SS appliances, and 9 yr old roof with heated side steps to ensure clear walkway no matter the weather. Maintenance free vinyl siding and a rear deck to enjoy the peaceful outdoors. House has been electrically wired for a generator. 1st shed is a workshop. Bright sunny flat lot with 2 sheds to provide plenty of extra storage. Just minutes to Bantam Lake, Litchfield White Memorial, Steep Rock or Mt. Tom and 2.30 hrs from NYC.

Listing Courtesy of Showcase Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 2.72% last updated on Nov 25, 2020
* 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

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.