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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

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.
$24,900

$24,900

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.
$24,900

$24,900

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.
$24,900

$24,900

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.
$24,900

$20,000

Warren, Connecticut

Joseph Lorino
5Bedroom(s)
3Full Baths
2.33Acreage Acres
37Picture(s)
Summer rental asking $20,000/month. Strawberry Ridge Chalet is nestled between pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is a 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 stream.
$20,000

$15,900

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.
$15,900

$13,900

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.
$13,900

$7,500

Washington, Connecticut

Maria Taylor
2Bedroom(s)
2Full Baths
8.58Acreage Acres
15Picture(s)
Tuck cottage. All New construction. Triple-mint, move-in ready. Perfect stone home with 11 foot ceilings, all new marble baths, all new kitchen with high end appliances. Perfectly reintegrated adjacent to the Tatetuck Farm, it has been redesigned and reimagined by a professional interior designer. Private, views, bucolic, 8.5+ acres surrounded by Land Trust and mature meadows.
$7,500

$5,900

Salisbury, Connecticut

Graham Klemm
5Bedroom(s)
2Full Baths
1Half Bathroom(s
5.89Acreage Acres
25Picture(s)
Annual Furnished Rental: $5,900/month. Well Located 5 Bedroom/2.5 Bath Colonial. Fresh & Clean & Ready! Totally Private & Quiet Near Villages of Salisbury & Lakeville. Proximate to Hotchkiss; Salisbury, Indian Mountain & other Area Schools. Great Eat-In Kitchen Tricked Out with Appliances. Main floor Guest Bed or Den. Generous Living Room with Fireplace & TV.
$5,900

$5,500

Litchfield, Connecticut

Jamie Marcoux
3Bedroom(s)
3Full Baths
1.2Acreage Acres
37Picture(s)
Meticulously Updated Antique Colonial. 3 Bedrooms. 3 Baths. 2 Fireplaces. Many Original Details. Terrace. Parklike Grounds. Views. 2-car Attached Garage with Electric Car Charger. Convenient Location. Close to Town Center & Green. 1.2? Acres. Must See! Offered Partially Furnished.
$5,500

$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

$4,000

Roxbury, Connecticut

Melinda Dubow
3Bedroom(s)
2Full Baths
5.15Acreage Acres
26Picture(s)
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 all new appliances including a wine cooler.
$4,000
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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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