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Sherman, CT Homes for Rent

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  • 95 Long River Rd, Sherman, CT 06784
    95 Long River Rd, Sherman, CT 06784
    95 Long River Rd, Sherman, CT 06784
    /25

    $7,500 Per Month

    • 4 Beds
    • 3.5 Baths
    • 4,400 Sq Ft
    • House for Rent

    95 Long River Rd, Sherman, CT 06784

    Incredible country home with heated gunite swimming pool skillfully blended into the natural stone landscape. The perfect place for relaxing and entertaining, whilst enjoying open, sunshine views over the golf course. Views from every room! Located within the River Oaks Country Club with resort quality amenities, this large and tastefully furnished 4 bedroom (each with walk-in closets), 3 & 1/2

    Tyler O'Hazo William Pitt Sotheby's Int'l

    95 Long River Rd, Sherman, CT 06784
  • 29 Route 55 W Unit B, Sherman, CT 06784
    29 Route 55 W Unit B, Sherman, CT 06784
    29 Route 55 W Unit B, Sherman, CT 06784
    /31

    $2,650 Per Month

    • 1 Bed
    • 1 Bath
    • 1,200 Sq Ft
    • House for Rent

    29 Route 55 W Unit B, Sherman, CT 06784

    Barn-Dominium! Don't miss this stunning, like-new rental in Connecticut's best little town - Sherman. This spacious, open-concept barn-style, one level home delivers over-the-top finishes throughout: rich hardwood floors, professional-grade kitchen appliances, butcher block island, quartz counters, and a high-end Samsung washer/dryer. Central air, an EV charging station, and exceptional energy

    Todd Sargent Coldwell Banker Realty

    29 Route 55 W Unit B, Sherman, CT 06784
  • 60 Leach Hollow Rd, Sherman, CT 06784
    60 Leach Hollow Rd, Sherman, CT 06784
    60 Leach Hollow Rd, Sherman, CT 06784
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    $6,000 Per Month

    • 2 Beds
    • 1 Bath
    • 2,936 Sq Ft
    • House for Rent

    60 Leach Hollow Rd, Sherman, CT 06784

    Located on a hill overlooking the main house of this 14 ACRE compound on a designated "Scenic Road," this 2BR/1B - 1929 solid stone cottage is just 60 M from NYC!Guests have access to the entire cottage full wooded property,water views of private lake are just past the driveway.Screened Porch & Extended Dining.This cottage was originally built by Helen Graham,assistant to Norman Vincent

    Kathleen Harrison Coldwell Banker Realty

    60 Leach Hollow Rd, Sherman, CT 06784
  • 32 Leach Hollow Rd, Sherman, CT 06784
    32 Leach Hollow Rd, Sherman, CT 06784
    32 Leach Hollow Rd, Sherman, CT 06784
    /40

    $20,000 Per Month

    • 4 Beds
    • 2.5 Baths
    • 2,714 Sq Ft
    • House for Rent

    32 Leach Hollow Rd, Sherman, CT 06784

    Beautifully restored and updated antique farmhouse with inground pool, cabana, guest house, tennis court and pond. Available to rent for July and August 2026. Scenic distant views frame this private 15-acre compound. Elegantly presented interiors, with extensive renovations supervised by an AIA architect specializing in historic preservation. Attention to detail and quality is evident throughout

    Irit Granger William Pitt Sotheby's Int'l

    32 Leach Hollow Rd, Sherman, CT 06784
  • 8 River Bend Ln, Sherman, CT 06784
    8 River Bend Ln, Sherman, CT 06784
    8 River Bend Ln, Sherman, CT 06784
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    $6,500 Per Month

    • 4 Beds
    • 2 Baths
    • 3,791 Sq Ft
    • House for Rent

    8 River Bend Ln, Sherman, CT 06784

    A contemporary home with heated infinity swimming pool perfect for relaxing or entertaining, whilst enjoying sunshine views over the golf course. Located within the River Oaks Country Club with resort quality amenities, this large and tastefully furnished 4 bedroom, 2 & 1/2 bath home is offered fully furnished and in mint condition. This well equipped home includes central air-conditioning and a

    Tyler O'Hazo William Pitt Sotheby's Int'l

    8 River Bend Ln, Sherman, CT 06784
  • 21 Route 39 S Unit A, Sherman, CT 06784
    21 Route 39 S Unit A, Sherman, CT 06784
    21 Route 39 S Unit A, Sherman, CT 06784
    /16

    $2,100 Per Month

    • 1 Bed
    • 1 Bath
    • 650 Sq Ft
    • House for Rent

    21 Route 39 S Unit A, Sherman, CT 06784

    One of a kind rental opportunity. Set on 10 magical acres with pond and brook. Private 1 bedroom above garage rental. Open concept with hardwood floors throughout. Center island kitchen opens to living room. Bedroom with built ins, walk in closet and small storage area. Laundry room (washer/dryer not included-front loader needed). Private entrance and mudroom/foyer. Beautiful tiles bathroom.

    Joe Chemero Coldwell Banker Realty

    21 Route 39 S Unit A, Sherman, CT 06784
  • 25 Hillside Dr, Sherman, CT 06784
    25 Hillside Dr, Sherman, CT 06784
    25 Hillside Dr, Sherman, CT 06784
    /36

    $20,000 Per Month

    • 4 Beds
    • 3.5 Baths
    • 3,303 Sq Ft
    • House for Rent

    25 Hillside Dr, Sherman, CT 06784

    Summer furnished rental opportunity! A true waterfront retreat with direct frontage on Candlewood Lake, this hidden gem is tucked away behind a perimeter of mature trees, offering a private and peaceful setting within the private Holiday Point Association. The community invites an active lifestyle with scenic opportunities for walking, hiking, and biking. Outdoor living shines here, featuring an

    Gary Crawford RE/MAX RISE

    25 Hillside Dr, Sherman, CT 06784
Connecticut Fairfield County Sherman

Homes for Rent in Sherman, CT

Why Live in Sherman

Sherman, CT, is a tranquil lakeside community located in the foothills of Connecticut wine country, offering a small-town atmosphere with proximity to Candlewood Lake. This man-made lake is a major attraction, featuring over 60 miles of shoreline where residents enjoy boating, hiking, ice skating, and skiing. Sherman is just an hour from New York City's theater district, making it a popular choice for second homes among Manhattan residents. The area boasts a variety of home styles, including Modern-influenced split levels, Modern Traditional homes, and lakeside lodges, often situated on multi-acre woodland lots. Education is a highlight, with The Sherman School serving kindergarten through eighth grade and Shepaug Valley Regional High offering a highly rated agriscience academy and a planetarium. Sherman is part of Connecticut wine country, hosting events like the rhubarb festival at White Silo Farm and community theater performances at Sherman Playhouse. For necessities, locals shop at Sherman IGA or drive 6 miles to New Milford for additional options like Big Y and Starbucks. New Milford also features Housatonic Brewing and Johana’s diner. Transportation is convenient with Route 7 leading to Danbury and I-84 connecting to Brewster's Southeast Station for trains to Grand Central Station. Sherman’s small-town charm is evident during national holiday celebrations, with fireworks on the Fourth of July and streets lined with American flags for Memorial Day.

Learn more about living in Sherman

Frequently Asked Questions

How much does it cost to rent a home in Sherman, CT?
The median rent for a home in Sherman, CT is $6,500 per month, though prices vary by neighborhood, size, and property type. As of June 2026, single-family homes tend to be the most affordable option.
How much do you need to make to afford rent in Sherman, CT?
To comfortably afford the median rent in Sherman, CT, a household needs to earn roughly $260,000 per year. This is based on the common guideline that households should spend no more than 30% of gross income on housing. Most landlords require monthly household income of at least 3x the monthly rent, and with a median rent of $6,500 per month in Sherman, CT, renters typically need to show $19,500 per month in gross income to qualify. Actual affordability will vary depending on household debts, other living expenses, and overall budget.
Is it more affordable to rent or buy in Sherman, CT?
In Sherman, CT, the price-to-rent ratio is 9.2, which generally favors renting. This ratio divides the median home price by the annual median rent: below 15 typically favors buying, 15 to 20 is balanced, and above 20 typically favors renting. Your finances, how long you plan to stay, and costs like mortgage rates, taxes, and maintenance all factor into the decision.

Rental Trends in Sherman, CT

There are currently 7 homes available for rent in Sherman, CT. The median rent is $6,500 per month, with single-family homes renting at $4,500.

Rental Home Trends

Number of Homes for Rent
7
Median Rent
$6,500
Median Single Family Home Rent
$4,500
How to Rent a Home

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