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

New Fairfield, CT45 Sail Harbour Drive

Price$1,695,000

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: 3.69% last updated on Nov 7, 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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76 Lake New Fairfield CT 06812

New Fairfield, CT76 Lake Drive South

Price$1,500,000

Est. Mortgage: $/month

MLS Number 170209894

  • Land
  • Acreage 1.58

This is the opportunity of a lifetime to build your dream waterfront home! Absolutely the best direct waterfront parcel on Candlewood Lake with breathtaking, expansive, southwestern exposure and an easy walk to the water. 1.58 acres of pure beauty in the exclusive, guarded, highly desirable Candlewood Isle water community. Approved, level building lot, deep water harbor & 300 feet of water frontage protected by a stone seawall. Wonderful home owner's association offering tennis, beach, clubhouse and much more!! Candlewood Lake itself is recognized as one the most desirable lakes on the East Coast. Just 65 miles from NYC, it is a popular tourist destination & the area is home to both year-round & second homes. The lake is used for recreation year-round for swimming, fishing and boating. Along its approximately 60-mile shoreline are tourist resorts & recreational facilities, including restaurants, beaches & marinas. Paddleboarding, water skiing, tubing & other water sports are commonly seen taking place on the lake, as well as sunbathing & more from the many docks & beaches. Create your own weekend retreat or full time residence. Approved building concept includes: 5 Bedrooms Main Home, separate 2 Bedroom Guest House and amazing Pool w/several outdoor terraces along the lake side. See rendering in supplements and photos. Convenient Getaway Destination - Less than 90 Minutes from NYC! It truly does not get better than this...Live the Dream!

Listing Courtesy of Neumann Real Estate

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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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: 3.69% last updated on Nov 7, 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

Sherman, CT39 Orchard Rest Road

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: 3.69% last updated on Nov 7, 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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312 Bantam Lake Morris CT 06758

Morris, CT312 Bantam Lake Road

Price$899,000

Est. Mortgage: $/month

Pending

MLS Number 170233403

  • Single Family
  • Property Style Bungalow
  • Bedrooms 3
  • Bathroom 1
  • Acreage 1.63

Charming 20th century bungalow anchors this Bantam Lake compound with TWO additional houses. Bright and sunny 1.6 acre lot with direct waterfront, major eastern views. Wide and open grassy lawn slopes to water with concrete and stone seawall. Steps to dock location. Three bedroom bungalow has great bones, stone fireplace, covered porch, attached three car garage. Second home is currently rented - two bedrooms, full bath, enclosed porch overlooking lake, classic pine paneling. Third cottage - two bedrooms, full bath, not winterized. Shed for storage. Very rare to find a three dwelling compound all on town sewer with waterfront. Multiple options: personal use, rental income, or build your dream lake house. VIEWS cannot be beat - property on "50 yard line" of Connecticut's largest natural lake.

Listing Courtesy of William Raveis Real Estate

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$
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$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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: 3.69% last updated on Nov 7, 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: 3.69% last updated on Nov 7, 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. 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: 3.69% last updated on Nov 7, 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

Goshen, CT62 Sherbrook Drive

Price$354,900

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

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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

Sherman, CT4 Liz Ann Lane

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: 3.69% last updated on Nov 7, 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

Warren, CT28 Brick School Road

Price$264,900

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.

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$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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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 $2,500 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

$
$
%
$/month over payments
Federal 30-year interest rate: 3.69% last updated on Nov 7, 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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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.