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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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$10,900

Washington, Connecticut

Peter Klemm
2Bedroom(s)
2Full Baths
20Picture(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.
$10,900
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$10,900

Roxbury, Connecticut

Peter Klemm
1Bedroom(s)
2Full Baths
3Acreage Acres
13Picture(s)
Large Vaulted Pool House. King BR + BA,Trundle BR/BA - King Bed or 2 Twins. Chef's Kitchen. Covered BBQ. Deck Overlooking Pool.Garage. SUMMER June - August $24,900/month Memorial - Labor Day $59,000; OFF-SEASON September - May $10,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $129,000. Possible to rent with Main House with its own plunge pool.
$10,900
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$8,000

Salisbury, Connecticut

Graham Klemm
5Bedroom(s)
2Full Baths
1Half Bathroom(s
5.89Acreage Acres
25Picture(s)
June $8k; July $8,500; August $8,500. Well Located 5 Bedroom/2.5 Bath Colonial. Fresh & Clean & Ready! Totally Private & Quiet Near Villages of Salisbury & Lakeville. Great Eat-In Kitchen Tricked Out with Appliances. Main floor Guest Bed or Den. Generous Living Room with Fireplace & TV. Multi-Zone Efficient Central AC. Main Floor Cozy Den or Office with TV.
$8,000
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$8,000

Warren, Connecticut

Joseph Lorino
5Bedroom(s)
3Full Baths
2.33Acreage Acres
26Picture(s)
Available November 1, 2023. 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.
$8,000
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$6,900

Warren, Connecticut

Peter Klemm
1Bedroom(s)
1Full Baths
1Half Bathroom(s
10Acreage Acres
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.
$6,900
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$6,000

Roxbury, Connecticut

Timothy G. Tierney
2Bedroom(s)
2Full Baths
1Half Bathroom(s
26Acreage Acres
28Picture(s)
Located on a less traveled town road, this light and airy 18th century Colonial has over 26 acres of peace and quiet. A large tranquil pond surrounded by white pine trees brings one back to nature. The home features 2 primary bedrooms, one on each level. Also, a designer kitchen with Carrara marble counters, a vaulted ceiling and custom island.
$6,000
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$5,000

Roxbury, Connecticut

Graham Klemm
3Bedroom(s)
3Full Baths
1Half Bathroom(s
3.42Acreage Acres
25Picture(s)
Available Now Until May 31, 2024 $5k/Month or Annually $6,500/month w/ Heated Pool. Utterly Charming In-Town Delight. 2 Bedroom, 2.5 Bath Main House + 1 Bedroom, 1 Bath Guest House with Separate Kitchen. Moments From Library, General Store & Town Tennis Courts. Inviting Eat-in Kitchen with Dining & Seating Area. Separate Formal Dining Room. Large Living Room with Fireplace.
$5,000
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$5,000

Washington, Connecticut

Melinda Dubow
2Bedroom(s)
2Full Baths
1Half Bathroom(s
3.97Acreage Acres
16Picture(s)
Enchanting 2-bedroom/2.5 bath cottage in pristine condition overlooking beautiful meadows on a quiet country road yet within minutes to Washington Depot. Beautiful country d?cor and high-end furnishings and linens. Lovely living room with hardwood floors, two cozy sitting areas one with T.V and the other with wood-burning fireplace.
$5,000
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$2,450

Sharon, Connecticut

Graham Klemm
1Bedroom(s)
1Full Baths
5.56Acreage Acres
11Picture(s)
$2,450/Month. Utterly Charming 1-bed/1-Bath Cottage. Large Great Room with Vaulted Ceiling & Fireplace. Good Wifi! Well Located Between Sharon & Lakeville, Near Hotchkiss, Indian Mountain & Salisbury Schools.
$2,450
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$1,900

Litchfield, Connecticut

Graham Klemm
1Bedroom(s)
1Full Baths
1Half Bathroom(s
0.01Acreage Acres
13Picture(s)
Newly Renovated Unfurnished 1 Bed, 1.5 Bath Second Floor Apartment. Super Light & Bright 2-Story Apartment in the Heart of Historic Litchfield Green - Arm's Distance to Numerous Shops & Restaurants. New Appliances in Kitchen & Newly Remodeled Baths. 1-Year Minimum Lease. Light & Bright. Tenant Pays Electric/Phone/Cable/Internet. No Pets Without Approval.
$1,900
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$1,650

Woodbury, Connecticut

Sallie Smith
1Bedroom(s)
1Full Baths
2Acreage Acres
11Picture(s)
This darling rental in the center of town has been completely refurbished. Beautiful hardwood floors. Eat in Kitchen. New entryway carpet, updated bath, new kitchen floor. This apartment is on two floors. Kitchen and large entryway foyer with W/D hook up(Dryer included in rental) is on first level. Bedroom, bath and living and office on second floor. Year lease only. No pets, non smokers only.
$1,650
23 Results returned.Per Page

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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