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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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$8,000

Warren, Connecticut

Joseph Lorino
5Bedroom(s)
3Bathroom(s)
2.33 Acres
23Picture(s)
Strawberry Ridge Chalet is nestled between pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is the 4 to 5 bedroom home. Top of the line eat-in kitchen with seating area and stone fireplace. Flooded with light the living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and walking bridge over the stream.
$8,000
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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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$6,200

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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$24,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
1.69 Acres
18Picture(s)
Hilltop private 4-bedroom home with heated 16’ x 32’ inground pool, basketball, croquet, badminton, ping pong, bikes, and board games. A short drive to the Washington Green, Mayflower Inn, great restaurants, land preserves, shops and Lake Waramaug State Beach. Dine or relax on the poolside terrace, porch or covered wood deck. Bedroom 1: King. Bedroom 2: King. Bedroom 3: 2 Queens.
$24,900
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$30,900

Warren, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
20.22 Acres
36Picture(s)
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.
$30,900
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$30,900

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
4.16 Acres
23Picture(s)
Pristine barn-style home on scenic dirt road with barn, stream and small pond. Walk or bike ride along the Shepaug River into a land preserve and historic farms. Magnificent granite fireplace, vaulted beam living room. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea. SUMMER: June - August $30,900/month. Memorial - Labor Day $74,900.
$30,900
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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
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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$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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$1,750

Washington, Connecticut

Joseph Lorino
2Bedroom(s)
1Bathroom(s)
0.2 Acres
7Picture(s)
Newly renovated, in-town apartment. Listen to the rushing river out the back yard. 2 bedrooms, office/dining room. Washer/dryer. Dishwasher. Living room facing the rushing river. All the shops and dining of New Preston just out your door. Lake Waramaug is 1/2 mile away. Rare, in-town gem in the both chic & charming village of New Preston with quaint shops and dining.
$1,750
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$30,000

Morris, Connecticut

Peter Klemm
4Bedroom(s)
4Bathroom(s)
2.1 Acres
37Picture(s)
FULLY RENOVATED HOME NESTLED IN THE LITCHFIELD HILLS WITH 270 FEET OF SERENE WATER FRONTAGE AND TONS OF AMENITIESrn4BR/3.5BA waterfront home custom built in 2004 and fully modernized in 2022 to include professionally designed furniture, décor, and amenities.
$30,000
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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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