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!

Contact The Matthews Group with any questions about buying a vacation home or to schedule a private viewing.

45 Sail Harbour New Fairfield CT 06812

Price$1,795,000

Est. Mortgage: $/month

MLS Number 170186026

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

A Dramatic Waterfront Private Retreat, on over 4.29 acres, with 380+ ft frontage, showcases scenic property, with over 2000 SF of multi-level decks & patios with 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 storage space. The two car detached garage hosts a 500 SF loft for play area, office space & many other potential uses. New roof, freshly painted in and out, cedar shake exterior , many recent updates including a fabulous sane patio with massive stone fireplace and lakeside patio area for inning , relaxation and outdoor fun. New dock complex, incredible wide lake views and an exceptional lake community with tennis, beach, clubhouse, Bocci court &more! Just 70minutes 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: 3.73% last updated on Sep 19, 2019
* 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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36 Chimney Point New Milford CT 06776

MLS Number 170224883

  • Single Family
  • Property Style Chateau, Cottage
  • Bedrooms 3
  • Bathroom 2
  • Acreage 0.33

AMAZING PRICE REDUCTION Iconic Waterfront, in sought after Candlewood Lake Club, offers incredible western exposure w/expansive lake views, exceptional updates quality finishes creating an authentic lake home design. A vaulted great room framed by beams, stone fireplace & hardwood floors opens to a renovated kitchen w/off white cabinetry, quartz counters, stainless appliances and island bar. The circular dining area occupies one of 2 stone turrets surrounded by windows & lake views. The second turreted area offers a wonderful entertaining space with built-in bar & cabinetry and adjoining enclosed hot tub area for private relaxation.The master suite occupies an entire floor of it's own, with private bath, walk-in closet and lake views. Two additional main level bedrooms, with updated bath and additional option for half bath ( plumbed), offer great space for family & guests. Stunning stone terraces, stone walls and walks, U-shaped dock, lake side cabana, carport, circular drive & professionally landscaped gardens create the ultimate lake getaway! The Lake Club community offers tennis, private beach, clubhouse and 9 hole golf course available to members. BEING SOLD FURNISHED. $10,000 initiation fee for club membership, annual dues of only $4,000.00, $525 for water and $775 for capital road improvement, $500 for other. A true lake getaway with all the amenities for a fun vacation home or choose the "Lake Club" lifestyle all year long!

Listing Courtesy of Coldwell Banker Residential Brokerage

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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

Price$949,000

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: 3.73% last updated on Sep 19, 2019
* 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.

Listing Courtesy of William Raveis Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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: 3.73% last updated on Sep 19, 2019
* 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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125 Strathmore Middlebury CT 06762

Price$549,000

Est. Mortgage: $/month

MLS Number 170183110

  • Single Family
  • Property Style Other
  • Bedrooms 4
  • Bathroom 4
  • Acreage 2.02

MAKE AN OFFER! Motivated sellers! One of Middlebury's most prestigious established neighborhoods! First time on the market is this contemporary colonial that has been meticulously maintained for over 3 decades. Located at the end of the cul de sac, the decorative driveway apron welcomes you & your guests to this private oasis. Don't let the driveway fool you! This home sits on a level usable lot that is fully fenced in. Perfect for your 4 legged friends. Enjoy a 4 season sun room overlooking the heated in-ground pool. Indoor entertaining is also a breeze w/ large living room & traditional formal dining room. Glass pocket doors between the living & family room. There is a finished bonus room over the garage that can serve many purposes such as a playroom, office, exercise room, or even a 5th bedroom or guest room. It doesn't end there. The walk out lower level is finished w/Owens Corning wall panels for added sound absorption & versatility that you can't get with ordinary drywall. It also has a separate entrance & half bathroom so this space is very multi functional, as well. This house would work well for the needs of a multi-generational family. House has central vac, Pella windows, & a whole house generator - never be inconvenienced by a power outage again! Would also be well suited for a 2nd or vacation home for those looking to escape NYC chaos. Middlebury is home to Lake Quassapaug Amusement Park & town residents have exclusive beach privileges at the lake.

Listing Courtesy of Gina Jacobs Real Estate & Property Management

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$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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62 Sherbrook Goshen CT 06756

Price$368,500

Est. Mortgage: $/month

MLS Number 170190680

  • Single Family
  • Property Style Colonial
  • Bedrooms 4
  • Bathroom 3
  • Acreage 0.86

A Woodridge lake home for all seasons. This 4 bedroom and 2. 5 bath home boasts an open floor plan with living room/Dining room combo featuring a gas fireplace built in cabinets, and kitchen with granite counters, stainless steel appliances, pantry, hardwood floors and more. The bedrooms are located on the second level with a master bedroom with a full tile bath, plus three additional bedrooms of various sizes. There is an office that can serve as a fifth bedroom. The lower level is mostly finished as a game room/rec/den/TV room. Extra storage is available. Outdoors you will find a raised 10 x 20 deck with stair case leading down to a custom stone patio with raised stone walls. This is a must see for a year round or vacation home.

Listing Courtesy of William Pitt Sotheby's Int. Re

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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205 Aspetuck Ridge New Milford CT 06776

MLS Number 170227286

  • Single Family
  • Property Style Cape Cod
  • Bedrooms 4
  • Bathroom 2
  • Acreage 1.66

PRIVACY, PRIVACY, PRIVACY! Drive up to your secluded 4 bedroom, 2 full bath Cape Cod. Gated in-ground pool area with pool house set back from the main house. Home is set on level portion of acreage surrounded by trees for your private enjoyment! This property offers a peaceful setting that gives you a feeling of a year round vacation home! Hardwood floors through out home except Family Room....carpeted Living Room and Dining Room (hardwood underneath). Family Room with beamed cathedral ceiling, skylights and large windows looking out to serene back yard. Upstairs Master Bedroom has a bonus room with window. This could easily be converted into a Master Bath/ Laundry Room! Stairs to access large walk-up attic (expansion possibility) are located in the over sized 2 Car Garage. Shed on property offers extra storage space. Full unfinished Basement with laundry hook ups. New well pump installed 2019. CT Basement System installed 2019. Home is waiting for your personal updating. Make sure you take a look at the Virtual Tour!!

Listing Courtesy of William Raveis Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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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28 Brick School Warren CT 06754

Price$274,900

Est. Mortgage: $/month

MLS Number 170227449

  • Single Family
  • Property Style Contemporary
  • Bedrooms 3
  • Bathroom 2
  • Acreage 2.65

Unique well maintained Contemporary Dome. Brand new septic.Beautiful Warren Location Private and secluded. Short distance to lake (private beach access for Warren residents).Turnkey updated kitchen and baths. Under 2 hours from NYC. Perfect for a family or vacation home.

Listing Courtesy of Showcase Realty, Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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

Price$265,000

Est. Mortgage: $/month

MLS Number 170224502

  • 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk A QuestionMore Details

21 Hubbard Litchfield CT 06759

Price$245,000

Est. Mortgage: $/month

MLS Number 170154021

  • Single Family
  • Property Style Cottage
  • Bedrooms 2
  • Bathroom 1
  • Acreage 1.8

Privacy & serenity in a charmingly redesigned country cottage in the woods directly on the Marshepaug River. This is an all year around weekend and vacation home. Sit on the screened porch and enjoy the view and the sound of the rushing water. This is a perfect weekend or full time home which escapes from the stress of our daily lives.The kitchen has been redone with new cabinets and appliances. Open level lot with woods on the perimeter providing complete privacy. On a private road in Milton, part of Litchfield, it is located in the woods, but only 5 minutes from the Litchfield Green with great shopping and fine restaurants and cultural activities. Important note: there is a new propane furnace that keeps the house toasty warm in the cold months.

Listing Courtesy of William Pitt Sotheby's Int'l

$
$
%
$/month over payments
Federal 30-year interest rate: 3.73% last updated on Sep 19, 2019
* 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 A VisitAsk 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.