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Annual Property Rentals in Connecticut and New York

Yearlong Rentals Available

KLEMM Real Estate can offer a range of properties for an extended stay in western Connecticut or southern New York? Our dedicated team of experienced agents can help you choose the perfect annual rental property in Litchfield, Fairfield, & New Haven Counties in Connecticut, or Dutchess and Columbia Counties in New York. As a multi-generational, family-owned firm, we are deeply familiar with the areas we represent and the rental search process.

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$24,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
4Bathroom(s)
3 Acres
25Picture(s)
Restored 3-BR Victorian Cottage with pool/spa/hot tub with wonderful gas barbeque stone terraces. Best scenic road for walking or bike riding by historic farms and homes owned by numerous artists, authors, actors and Wall Street executives. Relax or dine poolside surrounded by hedges and blue hydrangea. Specimen trees, enough flowers to keep vases full. Large wood burning fireplace.
$24,900
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$24,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Bathroom(s)
3.1 Acres
34Picture(s)
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.
$24,900
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$24,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
2Bathroom(s)
0 Acres
15Picture(s)
Pristine 4 Bedroom cottage on a wonderful yard near the Mayflower Inn and historic center of Washington. New chef's Kitchen and stainless steel appliances. Luxurious baths and bedrooms. Heated in ground gunite pool. 1 acre of flat lawn surrounded by endless summer Hydrangea. SUMMER June - August $24,900/month; Memorial - Labor Day $59,900; OFF-SEASON September - May $11,900/month.
$24,900
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$24,900

Washington, Connecticut

Peter Klemm
3Bedroom(s)
3Bathroom(s)
0.5 Acres
15Picture(s)
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.
$24,900
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$15,900

Washington, Connecticut

Peter Klemm
2Bedroom(s)
2Bathroom(s)
12Picture(s)
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.
$15,900
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$13,900

Warren, Connecticut

Peter Klemm
1Bedroom(s)
2Bathroom(s)
8Picture(s)
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.
$13,900
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$12,500

Pawling, New York

Joseph Lorino
4Bedroom(s)
4Bathroom(s)
70.4 Acres
32Picture(s)
4 bedroom 3.5 designer inspired home intended to complement the splendor of its natural surroundings. Fully furnished for comfortable luxury. 3 fireplaces and awe inspiring panoramic views. Soak in a breathtaking scene spanning the great meadow, rolling hills and mountains beyond.
$12,500
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$6,500

Washington, Connecticut

Sally Cornell
4Bedroom(s)
3Bathroom(s)
25Picture(s)
Escape from it all to this majestic location with a private pond, flowering trees and gardens. Completely renovated on almost 4 acres, this light filled home boasts four bedrooms, three full baths and two decks overlooking the pond. The Main Bedroom has a vaulted ceiling, private deck and attached bath with a Jacuzzi Tub.
$6,500
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$6,200

Cornwall, Connecticut

Joseph Lorino
4Bedroom(s)
2Bathroom(s)
8.94 Acres
27Picture(s)
Quintessential, country property up a long driveway to complete bliss and privacy. The Great Hill Cape is ideally located on the Litchfield/Cornwall boarder offering a serene and bucolic atmosphere. Open meadows on nearly 9 acres. 4 bedrooms and 2 baths. 2 fireplaces with one in the kitchen. Chef's kitchen with eat-in. Screened porch. 1 bedroom on the main floor and 3 upstairs.
$6,200
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$5,500

Woodbury, Connecticut

Maria Taylor
3Bedroom(s)
3Bathroom(s)
0.81 Acres
27Picture(s)
Gorgeous luxury townhouse in an important landmark building on Main Street. Also available FULLY furnished for $7,500 per month. Fabulous new renovation of 1753 building with original features that blend beautifully with modern touches. Offering spacious rooms and a total of 3,134 sq. ft of living space.
$5,500
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$2,200

Bethlehem, Connecticut

Timothy G Tierney
2Bedroom(s)
1Bathroom(s)
8Picture(s)
Two bedroom cottage with direct water frontage on Long Meadow Pond. Freshly painted and redone with energy efficient propane heat and central air. Hardwood floors throughout with a wood burning fireplace and French doors to a mahogany deck. The master bedroom also has French doors facing the lake.The home also features a one car attached garage and level yard.
$2,200
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$1,600

Waterbury, Connecticut

Sindy Butkus
2Bedroom(s)
2Bathroom(s)
11Picture(s)
Unit freshly painted, new flooring and new appliances. Convenient location near Waterbury Hospital. Tenant must have credit score of 700 and above. NO Smokers and No pets of any kind.
$1,600
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As you browse through our offerings of year-long rental properties in Connecticut and New York, imagine spending a year in your beautiful home surrounded by the scenic expanses of the region. From rolling hills to mountain views, lakefront escapes to secluded wooded homes, southern New York and western Connecticut offer serene properties for all tastes. Just a short trip away from New York City, the area provides a rustic escape from the city with all the amenities you and your family need. Whether you’re looking for an annual escape from the hustle and bustle of city life or a year-long taste of the rural countryside, our portfolio of annual rental properties can help you find what your family is looking for!

The process of finding a long term rental property can be confusing. That’s why KLEMM Real Estate leans on our decades of experience to help your family navigate this process as easily as possible. Our agents know the area inside and out. We know that you’ll fall in love with the quaint small towns and rolling hills of western Connecticut and southern New York. Let us help you find the perfect home to enjoy all that our area has to offer. Interested in learning more? Reach out to one of our experienced agents to get started.

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