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.

Town Line Roxbury CT 06783

Roxbury, CTTown Line Road

Price$16,000,000

Est. Mortgage: $/month

MLS Number 170254324

  • Single Family
  • Property Style Colonial
  • Bedrooms 10
  • Bathroom 10
  • Acreage 320

Greyledge Estate - one of the largest and most spectacularly situated properties in Litchfield County - is available for acquisition for the first time, in its entirety. In the event no transaction is effected by January 31, 2020, each parcel and any associated view sheds will be offered for sale individually, in a sequence to be determined. Greyledge Estate sits at the gateway to the Litchfield Hills, a popular and growing second home market defined by community and rural tranquility, that is only 80 miles from New York City. The Estate is one of the most spectacularly situated properties in Litchfield County in that it occupies an elevated position on a picturesque ridge running along the border of Bridgewater and Roxbury, Connecticut. The 320±-acre property is comprised of contiguous land parcels that are bordered by over 500 acres of perpetually protected Land Trust property to the north and to the east of the estate. Greyledge Estate is further differentiated by its scale and scarcity as it is one of the largest parcels of unencumbered, prime land in Western Connecticut. The property offers a rare combination of near 360-degree views to the horizon, multiple elevated build sites, more than 100 acres of farm fields, woods, and approximately 25,000 square feet of beautifully maintained homes and out-buildings. The purchaser can maximize the value of the existing land by reconfiguring select parcels and performing lot line adjustments with neighboring properties

Listing Courtesy of William Pitt Sotheby's Int'l

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Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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86 & 88 Lake New Fairfield CT 06812

MLS Number 170274173

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 5
  • Acreage 0.62

Located in the gated community of Candlewood Isle - be the owner of two homes that have the perfect views of Candlewood Lake. The first home has an open floor plan featuring an octagon shaped area off the living room with amazing views of the lake. The kitchen has granite counter tops, ample storage and skylights for natural sunlight. The hardwood flooring flows throughout the entire dining area, living room area and both bedrooms. The first of 2 bedrooms is a master suite which has a master bathroom featuring a separate shower and tub, double sinks and storage. The 2nd bedroom and 2nd full bathroom are off the hallway. The living room has a large stone fireplace and slider doors which lead out to either the stone patio or deck areas which go down to lower decks for more entertaining areas come down to the water line of the lake where you will find a shed for storage of water toys, fishing gear, etc. There are a total of 4 docks for all the summer fun. The second home has a two car garage and has been totally renovated to absorb the spectacular lake views. From the glistening floors to the new kitchen and bathroom. A true must see!

Listing Courtesy of Reilly Biasetti Real Estate

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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45 Sail Harbour New Fairfield CT 06812

New Fairfield, CT45 Sail Harbour Drive

Price$1,595,000

Est. Mortgage: $/month

MLS Number 170186026

  • Single Family
  • Property Style Contemporary
  • Bedrooms 4
  • Bathroom 5
  • Acreage 4.29

Reduced 250K from original list, this Dramatic Waterfront Private Retreat is a special Sail Harbor Opportunity. Situated on over 4.29 acres, with 380+ ft frontage this scenic property, with over 2000 SF of multi-level decks & patios showcases an exquisite stone fireplace and wide lake views. An open floor plan, with a towering 28 ft window wall brings the lake Views in. A main level master suite provides a relaxing oasis with double pedestal sinks, soaking tub , separate shower and walk-in closet with built-ins. two spacious bedroom suites on the upper level offer generous walk-n closets handful baths with space for two queen size beds in each room. The finished walk -out offers a game room with media center, 4th bedroom, full bath and plenty of storage space. The two car detached garage hosts a 500 SF loft for play area, office space or Artist's Loft with balcony and views of the lake! Below Market Value with over 450K in improvements. New roof, freshly painted in and out, cedar shake exterior , many recent updates including a fabulous stone patio with massive stone fireplace and lakeside patio area for relaxation and exceptional privacy & views! New dock complex, incredible wide lake views and an exceptional lake community with tennis, beach, clubhouse, Bocci court &more! Just 70 minutes to NY city. Come see why Candlewood Lake is your vacation and or second home destination.

Listing Courtesy of Coldwell Banker Residential Brokerage

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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39 Orchard Rest Sherman CT 06784

Sherman, CT39 Orchard Rest Road

Price$895,000

Est. Mortgage: $/month

MLS Number 170185855

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.93

Open Plan Waterfront Contemporary, in a private Sherman location, with an ideal NY commute , just 70 min to NY city offers an open floor plan with 3 bedrooms, 3 full updated baths and flex spaces for easy entertaining. The expansive wrap deck surrounds the home with options of entertaining indoors to out. Bright lake colors, hardwood floors, 2 brick fireplaces that warm the heart of the home and serene surroundings with lofty lake views, make this an ideal lakefront getaway. The Updated kitchen showcases stainless appliances, breakfast bar, granite counters & built in pantry for expanded storage plus a dining area with sliders to private deck. The vaulted great room with adjacent open dining area is ideal for large gatherings & easy entertaining options indoors to out. A main level guest room with stylish full bath offers ideal space for guests. The upper level showcases a private, vaulted master suite with multiple closets, loft seating & private porcelain tiled bath. The lower level offers a spacious family room with dining area as well as a private guest bedroom and newer full bath with whirlpool and shower . Lofty views, easy access stairs to lakefront, private stone terrace with fire pit and private dock w/serene lake views, deep water harbor, wide paved drive & 220 ft frontage make this an excellent choice for your second home or weekend/summer getaway. Don't miss a fresh look at this great lake opportunity! No common fees & low Sherman taxes!

Listing Courtesy of Coldwell Banker Residential Brokerage

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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33 Wheaton Washington CT 06794

MLS Number 170147740

  • Land
  • Acreage 13.17

Price Reduced to SELL! 13+ acres w/ Barn 7 stalls & Cape/cottage. House needs work and is being sold AS IS. Enter tree-lined driveway. Watch sunrises and sunsets while enjoying the view of the rolling hills. Open land with lightly wooded edges, stone walls and flowing East Aspetuck river on west side of property. Located in the heart of Washington Depot, it boasts privacy sitting on a quiet road, while still close to the center of town. With nearby pleasures of Lake Waramaug just 1 mile away. The lake also has world class restaurants, nearby vineyards and EnRoute of CT Wine Trail, enjoy wine tastings, golf course, and shopping. This beautiful 13.17 acres, displaying a 1100 sq ft Cape Cod style home, an antique barn, stables, paddock and fenced in areas for the ponies. Endless opportunities, this property is perfect for agricultural farming with a reported 85% solar potential, possibility of subdividing or a perfect vacation home. This is truly worth a showing! Right side of property 225 ft road front. Left side 60 ft road front. Center driveway in right-of-way of 31 Wheaton Rd property.

Listing Courtesy of Coldwell Banker Residential Brokerage

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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33 Wheaton Washington CT 06794

MLS Number 170166214

  • Single Family
  • Property Style Cape Cod, Cottage
  • Bedrooms 1
  • Bathroom 1
  • Acreage 13.17

Price Reduced to SELL! House, Barn and 13+ acres. Enter tree-lined driveway. Cape/ Cottage home w/ 1 bdrm on 1st floor. Loft on upper level. Amazing views of rolling hills in the serenity of a private landscape. Open land with lightly wooded edges, stone walls and flowing East Aspetuck river on west side of property. Located in the heart of Washington Depot, it boasts privacy sitting on a quiet road, while still close to the center of town. With nearby pleasures of Lake Waramaug just 1 mile away. The lake also has world class restaurants, nearby vineyards and EnRoute of CT Wine Trail, enjoy wine tastings, a golf course, and shopping. This beautiful 13.17 acres, displaying a 1100 sq ft cape cod house, an antique barn, stables, paddock and fenced in areas for the ponies. Endless opportunities, this property is perfect for agricultural farming with a reported 85% solar potential, possibility of subdividing or a perfect vacation home. This is truly worth a showing! Right side of property 225 ft road front. Left side 60 ft road front. Center driveway in right-of-way of 31 Wheaton Rd property. House needs work sold AS IS.

Listing Courtesy of Coldwell Banker Residential Brokerage

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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22 Chestnut Hill Litchfield CT 06759

MLS Number 170234327

  • Single Family
  • Property Style Cottage
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.4

TWO tastefully renovated homes comprise this classic compound. Tucked into a private, lightly wooded lot this property is contiguous to both White Memorial Land Trust land and three classic Chestnut Hill farm properties. Originally part of the Haight Vineyard estate, current owner carefully renovated main dwelling to include two bedrooms, combined dining and living space, beautifully appointed kitchen and bonus room that could serve as office, den or third bedroom. Newly finished hardwood floors, exposed brick and beams, vaulted ceilings, modern fittings in both bathrooms and porcelain tile backsplash are only a few of the details in the main house. Brand new mechanical systems and wiring. Blue stone patio and classic boxwood plantings. Newer septic and well. In addition, there is a two bedroom second home that could be used as a guest house, office or studio. Also fully renovated with kitchen, loft, office, living space, small private deck and patio. Property can serve as compound, studio space, rental income - the opportunities here are ENDLESS. Walk or drive - one mile to Litchfield town Green for restaurants, shopping, events.

Listing Courtesy of William Raveis Real Estate

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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11 College Hill North Canaan CT 06024

MLS Number 170268623

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 4
  • Acreage 5.4

OWLS NEST is located on a hillside adjacent to a gentle forest with open spaces. The colonial-style home offers a large private deck with a hot tub overlooking the private grounds. A large rustic screened-in porch provides privacy while maintaining an outdoor feeling. There are 3/4 bedrooms and 3 1/2 baths. The formal entry opens to a spacious living room with a large stone fireplace and french doors. There is also a spacious formal dining room off the foyer. The kitchen is filled with amenities and a private informal dining area. The family room off the kitchen has a stunning raised stone fireplace. The partially finished basement provides a variety of choices for additional living space. There is abundant storage. The privacy of the grounds provides a haven for gentle wildlife such as deer, owls, and turkey. OWLS NEST is ideal for year-round living or a second home.

Listing Courtesy of Elyse Harney Real Estate

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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349 New Harwinton Torrington CT 06790

MLS Number 170240179

  • Multi Family Multi-Family For Sale
  • Property Style Other
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.48

GREAT INCOME PRODUCING OPPORTUNITY! TWO on ONE lot each with attached garages. Currently brings in $2,700 a month! The front home is 1,907 square feet, 4 bedrooms, 1 full bath, stone fireplace & attached private garage. The second home is 1,090 square feet, 2 bedrooms, 1 full bathroom, a 1/4 bath upstairs in the master suite with a walk-in close, and an attached garage. Great for someone looking for an in-law set up. Live in one & rent the other or a great opportunity to build your real estate portfolio or to start one. The location is wonderful, the back yard is ample, and the curb appeal is simply lovely. Both properties are solidly built & feature wonderful upgrades making them desirable, not to mention the income they can provide with their great rents. Upgrades include roof, siding, appliances, paved driveway and windows on both homes. One of them offers newer water heater, oil furnace, and front & back doors all leaving you with a peace of mind that your new homes are well maintained. Torrington hosts the historical Warner Theater, a most wonderful children's museum-Kid's Play, schools, playgrounds, Eastwood Country Club, fantastic downtown community with a plethora of shopping and multiple dining options. Route 8 & Route 44 easily guide you to New York City & Massachusetts!

Listing Courtesy of Keller Williams Realty

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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4 Liz Ann Sherman CT 06784

Sherman, CT4 Liz Ann Lane

Price$255,000

Est. Mortgage: $/month

MLS Number 170270250

  • Single Family
  • Property Style Ranch
  • Bedrooms 2
  • Bathroom 2
  • Acreage 0.23

Wonderful opportunity to own a home in historic Sherman Connecticut, for less that the cost of purchasing a condo! Plus, low Sherman taxes. Nestled in secluded Candlewood Echoes, this recently renovated home offers boaters, kayakers, and beach lovers access to a private beach and boat dock on Squantz Pond, while hikers can head to the nearby Appalachian Trail. Owners may also use the town boat launch on Candlewood Lake. Property is centrally located and is ideal as a full-time residence or vacation home as it is only 90 minutes from Manhattan and 15 minutes from Metro North trains. The tastefully decorated kitchen features granite counters, stainless steel appliances, and sliders to a spacious deck. A fully finished lower level includes a large living/family room, 3rd bedroom/den, and a walkout to the side yard. Basement has recently received a certificate of occupancy, and there is a fully finished shower behind wall in lower level bathroom that can be easily accessed. Furnace installed 2018. Annual district tax of $405.00 covers beach, docks and insurance. Home opposite is empty and being renovated. Please excuse disarray.

Listing Courtesy of Coldwell Banker Residential Brokerage

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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108 Quanopaug Woodbury CT 06798

Woodbury, CT108 Quanopaug Trail

Price$109,900

Est. Mortgage: $/month

MLS Number 170190670

  • Land
  • Acreage 1.05

Surrounded by Open Space and Flander's Nature Preserve, yours to enjoy for eternity, this 1.05 acres of improved land is located on one of Woodbury's charming quintessential country roads. The ready to build lot is at the end of a private drive and abuts seemingly endless acres of woods, vernal streams, and abundant wildlife. Building your home here is all about enjoying nature yet being under 15 minutes to interstate 84. Owners donated over 100 acres to Flander's, preserving the land around you for eternity. Pay taxes on 1.05 acres but have all the benefits of being surrounded by Nature Preserve, yours to enjoy. The picturesque tree-lined Main Street and antiques shops aplenty have helped Woodbury earn Reader's Digest magazine's Most Charming Small Town in Connecticut designation in 2018. Come build your full time residence or your dream weekend/vacation home.

Listing Courtesy of Drakeley Real Estate, Inc.

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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321 Cliffside Torrington CT 06790
Pending

MLS Number 170285179

  • Condo
  • Property Style Townhouse
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,410

" SERENITY" Crisp clean country air surrounds this Stunning Contemporary Lakeridge Condominium in a secured gated community offering unbelievable amenities for a country retreat/vacation home or year-round living. Just over 2 hours from NYC located in a rural area yet close to major amenities. This Woodhaven model offers multiple tasteful upgrades. A Totally private deck overlooks the forest. There are 3 bedrooms and 2 full baths. Upgrades include, but are not limited to, central heat and air, a gas log fireplace insert and remote control, custom kitchen cabinets and counters, engineered hardwood floors throughout the first floor, new carpet on the second floor, newly painted throughout, all new 6 panel interior doors, all new blinds and interior access to a heated storage area. A skylight in the living area floods the space with light. The Lakeridge community offers security services, a clubhouse, spa and health club, indoor and outdoor pools, indoor and outdoor tennis courts, basketball court, Lakeridge Cafe "in season", playground, Tot Lot, lake and beach access, walking trails nearby, stables, garden area, and skiing and much more. The website for the Lakeridge Community: www.lakeridgect.com

Listing Courtesy of Elyse Harney Real Estate

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$/month over payments
Federal 30-year interest rate: 3.33% last updated on Apr 9, 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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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.