Litchfield County, CT Rentals

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  $6,500 total monthly price

  • 5 Beds
  • 3 Baths
  • 3,428 Sq Ft
  • House for Rent

  38 Strawberry Ridge, Warren, CT 06777

  Strawberry Ridge Chalet is nestled between two pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is the 4 to 5 bedroom home. Eat in kitchen with seating area and stone fireplace. Living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and stream. Office/5th bedroom and full bath complete the 1st floor. The 2nd floor

  Joseph Lorino Klemm Real Estate Inc

  38 Strawberry Ridge, Warren, CT 06777
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  /22

  $2,800 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,260 Sq Ft
  • House for Rent

  10 Sentry Hill Rd, Roxbury, CT 06783

  Upper 3-bedroom, 2-bath now available from February 2026 @ $2,800! Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 3-bedroom, 2 bath home rests on five acres with a gentle stream running through it. State of the art chef's kitchen with

  Melinda Dubow Klemm Real Estate Inc

  10 Sentry Hill Rd, Roxbury, CT 06783
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  $5,800 total monthly price

  • 2 Beds
  • 2.5 Baths
  • 2,500 Sq Ft
  • House for Rent

  55 Still Meadow Rd, Sharon, CT 06069

  Fabulous Converted Barn Rental Available November 2025 to May 2026. This beautifully converted barn offers a peaceful and luxurious retreat on 40 private acres at the end of a quiet, dead end road. Located within walking distance to the village of Sharon and near Lakeville, Salisbury, Kent, Cornwall, Warren, Millbrook, and Millerton. Close to Washington, Litchfield, Rhinebeck, Hudson, and Great

  Ann Stettner Neil Charles Real Estate

  55 Still Meadow Rd, Sharon, CT 06069
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  $19,500 total monthly price

  • 6 Beds
  • 5 Baths
  • 3,450 Sq Ft
  • House for Rent

  321 W Shore Rd, New Preston Marble Dale, CT 06777

  Available May 15 - Sept 15, 2026 at $19,500 a month. Inquire about custom terms, more time or annual terms. Inquire for details about use of Luxury pontoon boat for cruising and waterskiing. Enjoy this chic and renovated home on glamorous Lake Waramaug. Walk across the street to the fabulous dock with spacious lake side lawn. Canoe is available for use. 6 bedrooms (3 en-suite) with plenty of room

  Stacey Matthews W. Raveis Lifestyles Realty

  321 W Shore Rd, New Preston Marble Dale, CT 06777
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  $7,500 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 3,026 Sq Ft
  • House for Rent

  18 Bear Burrow Rd, Roxbury, CT 06783

  Charming barn-style home on 15.27 acres off quiet country road. Four bedrooms and two and one half baths. Open floor plan. Exposed timber. Double sided stone fireplace. French doors to rear patio. In ground pool and barrel sauna. The perfect summer retreat in the beautiful town of Roxbury. Available short term between September to May for $7,500 per month. Contact agent for availability. Just 90

  Maria Taylor Klemm Real Estate Inc

  18 Bear Burrow Rd, Roxbury, CT 06783
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  $12,900 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • House for Rent

  23 Painter Hill Rd, Roxbury, CT 06783

  Pristine hilltop art filled home with views and only a short walk to Maple Bank Farm Stand, Toplands Farm and historic Roxbury Center. Wood burning fireplace, vaulted master bedroom with balcony and private bath. Dine or relax on the flagstone terrace. Ping pong, trampoline, croquet, badminton, gas BBQ, fire pit, bikes and board games. SUMMER June - August $18,900/month; OFF-SEASON September -

  Peter Klemm Klemm Real Estate Inc

  23 Painter Hill Rd, Roxbury, CT 06783
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  $6,900 total monthly price

  • 1 Bed
  • 1.5 Baths
  • 995 Sq Ft
  • House for Rent

  141 Melius Rd, Warren, CT 06754

  Comfortable One-Bedroom Cottage on Warren's best farm walking, running, bike riding road near Warren Town Center. Set on a 20-acre site. Older shared tennis court. Close to Mohawk Skiing, Lake Waramaug Town and State Beaches, Washington. Kent and Litchfield Restaurants.SUMMER June - August $13,900/month; Memorial - Labor Day $34,900;OFF-SEASON September - May $6,900/month. If over 3 months,

  Peter Klemm Klemm Real Estate Inc

  141 Melius Rd, Warren, CT 06754
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  $1,600 total monthly price

  • 1 Bed
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  104 Main St, Torrington, CT 06790

  AVAILABLE THIS UNIT IS LARGER WITH A 1 FULL BEDROOM ! Be a part of the newest studio style apartments right here in the hub of Litchfield County. Completely brand-new units located in a refurbished historic building in downtown Torrington. Located steps away from theatre, restaurants, and shopping - The Clayton features this brand-new unit ready to be lived in - with features such as led

  Travis Lipinski W. Raveis Lifestyles Realty

  104 Main St, Torrington, CT 06790
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  $13,900 total monthly price

  • 4 Beds
  • 3.5 Baths
  • 3,400 Sq Ft
  • House for Rent

  143 Melius Rd, Warren, CT 06754

  Pristine barn-style home on scenic dirt road with stream and small ponds. Walk or bike ride along this scenic road into a land preserve and historic farms. Magnificent stone fireplace, vaulted beam living room. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea. Tennis. Close to Lake Waramaug and Mohawk Mountain Skiing. Main House:

  Peter Klemm Klemm Real Estate Inc

  143 Melius Rd, Warren, CT 06754
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  $1,750 total monthly price

  • 2 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Apartment for Rent

  90 24 Bumper Rd, Harwinton, CT 06791

  Welcome to Bumper Brook Estates, Harwinton's finest and newest Active Adult 55 + rental community. These garden style units are situated on the western side of Harwinton. This community will contain all of the finest concepts that active adults love about a home without the maintenance cares. There will be a total of 36 spacious units. Bumper Brook Estates is unique in many ways. All units

  Scott Bayne Century 21 Bay-Mar Realty

  90 24 Bumper Rd, Harwinton, CT 06791
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  $11,900 per month

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft
  • House for Rent

  Unlisted Address

  Meander down the most scenic of Roxbury dirt roads to reach "Tunnel Road 4-BR" tucked between the Shepaug River, historic wood Judd's Bridge and Farm and 1000 acres of Steep Rock land trust with endless hiking trails. Pristine renovated private country home with year round 8'x 16' spa pool, wood burning fireplace and open floor plan. Dine or relax on the granite terrace or covered front porch.

  Peter Klemm Klemm Real Estate Inc

  Unlisted Address
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  $14,900 total monthly price

  • 7 Beds
  • 9 Baths
  • 15,000 Sq Ft
  • House for Rent

  10 Sunny Ridge Rd, Washington, CT 06793

  Major estate with the highest standards of construction located within the Sunny Ridge historic district. Situated on 10 private, park-like acres with an over-sized heated pool, fabulous stonewalls, giant dining terraces, pond and orchard. 7+ bedrooms, Billiard room, screening room, paneled library, sunroom, new country kitchen, 100-person party room boasts a restaurant size bar, sound system and

  Peter Klemm Klemm Real Estate Inc

  10 Sunny Ridge Rd, Washington, CT 06793
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  $12,900 total monthly price

  • 4 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • House for Rent

  47 Calhoun St, Washington Depot, CT 06794

  Charming mint renovated Nantucket-style cottage set on 25 acres of meadows with apple trees and 200-year old maples. Breathtaking hilltop views overlook farms, the Town of Washington and church steeples. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.SUMMER June - August $26,900/month; Memorial - Labor Day $69,900; OFF-SEASON

  Peter Klemm Klemm Real Estate Inc

  47 Calhoun St, Washington Depot, CT 06794
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  $12,900 total monthly price

  • 4 Beds
  • 4 Baths
  • 2,396 Sq Ft
  • House for Rent

  247 Painter Hill Rd, Roxbury, CT 06783

  Mint St. Barth's-style home in perfect hilltop neighborhood with heated pool. Exceptional interior design with two wood burning fireplaces and vaulted ceilings. SUMMER June - August $26,900/month, Memorial - Labor Day $69,900. OFF-SEASON: September - May $12,900/month--If over 3 months, subtract $1,000 per month. And no tax is due. ANNUAL: $159,000. Inquire for other/shorter rental terms.

  Peter Klemm Klemm Real Estate Inc

  247 Painter Hill Rd, Roxbury, CT 06783
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  $13,900 total monthly price

  • 3 Beds
  • 3.5 Baths
  • 4,251 Sq Ft
  • House for Rent

  45 Moosehorn Rd, Roxbury, CT 06783

  Perfect 6BR 3.5 Bath home with heated pool and child's play gym on a scenic country dirt road that leads into a land preserve along the Shepaug River - perfect for walking, jogging, biking. The most desirable rural historic location within 2 hours of NYC - Roxbury and Washington CT. Home to actors, writers, artists and the owners of luxury estate vacation homes. Many world class restaurants, inns

  Peter Klemm Klemm Real Estate Inc

  45 Moosehorn Rd, Roxbury, CT 06783
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  $10,900 total monthly price

  • 2 Beds
  • 2 Baths
  • 2,153 Sq Ft
  • House for Rent

  17 Kirby Rd, Washington, CT 06793

  Pristine Arts & Crafts Carriage House. Perfect setting on Washington's Historic Green surrounded by the Frederick Gunn School and historic shingle-style Rossiter mansions. Ground floor ensuite primary bedroom, office with sleeper sofa and cozy den with wood-burning fireplace. Upstairs, king bedroom with ensuite bath, large living room, dining room and eat-in kitchen. Fabulous mahogany deck for

  Peter Klemm Klemm Real Estate Inc

  17 Kirby Rd, Washington, CT 06793
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  $13,900 total monthly price

  • 6 Beds
  • 3.5 Baths
  • 2,716 Sq Ft
  • House for Rent

  33 Sentry Hill Rd, Roxbury, CT 06783

  Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

  Peter Klemm Klemm Real Estate Inc

  33 Sentry Hill Rd, Roxbury, CT 06783
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  $11,900 total monthly price

  • 3 Beds
  • 3 Baths
  • 1,933 Sq Ft
  • House for Rent

  110 Shearer Rd, Washington, CT 06793

  Restored country cottage furnished with antiques, fine furnishings & oriental rugs. New gunite in-ground pool and terrace. Wonderful scenic dirt road walking or bike riding through historic estate neighborhood. Relax or dine with a bbq on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.SUMMER June - August $24,900/month; Memorial - Labor Day

  Peter Klemm Klemm Real Estate Inc

  110 Shearer Rd, Washington, CT 06793
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  $13,900 total monthly price

  • 4 Beds
  • 3 Baths
  • 3,530 Sq Ft
  • House for Rent

  51 Senff Rd, Washington, CT 06793

  Pristine 5-bedroom private home on scenic dirt road ideal for walking, jogging and biking. Magnificent design with 2 gas fireplaces and filled with the art of Thomas McKnight. 2 over-sized wood decks overlooking the heated pool surrounded by endless summer hydrangea and 3 acres of lawns. The perfect location minutes from the center of Washington, the Mayflower and Winrian Inns & Spas.SUMMER:June

  Peter Klemm Klemm Real Estate Inc

  51 Senff Rd, Washington, CT 06793
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  $2,000 total monthly price

  • 2 Beds
  • 1.5 Baths
  • 995 Sq Ft
  • Townhouse for Rent

  115 Beard Dr, New Milford, CT 06776

  Beautiful and well-maintained Two bedroom condo for rent in desirable Prospect Common in Milford. This charming unit features a cozy fireplace, an updated and functional kitchen with washer and dryer , and a bright, comfortable layout. Enjoy the convenience of condo living with access to the community swimming pool and clubhouse/rec house. Great location close to shopping, dining, and major

  Holly Mullins Coldwell Banker Realty

  115 Beard Dr, New Milford, CT 06776
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  $20,000 total monthly price

  • 3 Beds
  • 3 Baths
  • 2,384 Sq Ft
  • House for Rent

  40 Camps Flat Rd, South Kent, CT 06785

  Experience the ultimate country retreat with this charming, fully furnished 3-bedroom, 3-bathroom cottage set on 13+ private acres. Available for the Academic year or Winter rental, this inviting property features a heated saltwater gunite pool, a separate guest cottage, beautifully maintained grounds, and perennial gardens. The main residence boasts a sun-filled kitchen with an eat-in area, a

  Vanessa Henderson William Pitt Sotheby's Int'l

  40 Camps Flat Rd, South Kent, CT 06785

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