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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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$14,900

Washington, Connecticut

Peter Klemm
5Bedroom(s)
5Full Baths
1Half Bathroom(s
31Picture(s)
Fabulous weekend retreat. Perfect for entertaining. 5,000+SF renovated home and guest house currently designed with 8 bedrooms and 5.5 marble baths. Original 18th century farm house was expanded with massive high-ceiling living room with fireplace, screening room, and master bedroom.
$14,900
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$13,900

Washington, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
3Half Bathroom(s
15.58Acreage Acres
29Picture(s)
Magnificent country home, pool, and spa on coveted Calhoun Street. 15 private acres of stone terraces, gardens, fruit trees, fields, extraordinary views, only 1 mile from town. Close to New Preston and Lake Waramaug. 4-6 bedroom Dutch Colonial with LR, DR, Library, Chef's Kitchen with large dining area, Large Pantry, Den and 3 full and 3 half bathrooms, 4 Fireplaces, 2-Car Garage.
$13,900
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$13,900

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
3Full Baths
1Half Bathroom(s
4.16Acreage 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.
$13,900
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$13,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
3Full Baths
2.21Acreage Acres
16Picture(s)
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.
$13,900
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$13,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
1Half Bathroom(s
8.04Acreage Acres
22Picture(s)
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.
$13,900
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$13,900

Warren, Connecticut

Peter Klemm
4Bedroom(s)
3Full Baths
1Half Bathroom(s
20.22Acreage 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.
$13,900
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$12,900

Roxbury, Connecticut

Peter Klemm
4Bedroom(s)
2Full Baths
1Half Bathroom(s
3Acreage Acres
25Picture(s)
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.
$12,900
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$12,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
8.64Acreage Acres
21Picture(s)
Pristine 3-bedroom private mint farmer's home ideal for walking, jogging and biking. Magnificent design with antiques, art and 2 fireplaces, over-sized living room, dining room for 10 and chef's kitchen. Heated pool surrounded by endless summer hydrangea and 11 acres of lawns, pond, and fields. The perfect location minutes from the centers of Roxbury and Washington.
$12,900
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$11,900

Washington, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
0.5Acreage Acres
14Picture(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.
$11,900
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$11,900

Washington, Connecticut

Peter Klemm
4Bedroom(s)
3Full Baths
1Half Bathroom(s
1.69Acreage 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.
$11,900
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$11,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
3Full Baths
1Half Bathroom(s
3Acreage 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.
$11,900
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$11,900

Roxbury, Connecticut

Peter Klemm
3Bedroom(s)
2Full Baths
1Half Bathroom(s
3.1Acreage 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.
$11,900
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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