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Homes for Rent near Booth Free School

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  • /32

    $29,500 per month

    • 4 Beds
    • 3.5 Baths
    • 2,360 Sq Ft
    • House for Rent

    126 River Rd, Washington Depot, CT 06794

    AVAILABLE JULY OR AUG 2025 @ $29,500. Chic Riverfront Summer rental. 4 bedroom 3 1/2 baths on a quiet street close to Steep Rock Land Trust's hiking trails and minutes from Washington Depot. Open floor plan, hardwood floors throughout, top of the line chef's kitchen w/ butler's pantry. 2 first floor bedrooms with jack-and-jill bath. 2 bedrooms upstairs, each with full baths, finished lower level.

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (860) 362-3190

    126 River Rd, Washington Depot, CT 06794
  • /14

    $2,500 per month

    • 1 Bed
    • 1 Bath
    • 875 Sq Ft
    • Apartment for Rent

    160 North St, Roxbury, CT 06783

    FURNISHED RENTAL AVAILABLE SEPT 2, 2025- MAY 2026 @ $2,500/MONTH. Spacious one bedroom apartment above garage on large, private estate. Clean, updated and comfortable. Bright living room with built ins and mini bar. Dining room and kitchen. Stackable washer/dryer in unit. Excellent credit, references and application required. Electricity included. Oil heat paid for by tenant.

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (860) 750-8200

    160 North St, Roxbury, CT 06783
  • /27

    $20,000 per month

    • 3 Beds
    • 3 Baths
    • 2,312 Sq Ft
    • House for Rent

    95 Shinar Mountain Rd, Washington Depot, CT 06794

    AVAILABLE FOR JULY 2025 @$20K/MONTH. Private country escape with dramatic sunsets. Chic mid-century modern with 3 bedrooms and 3 full baths. Floor to ceiling windows in the Large and airy living room and dining room combo. This layout is conducive to easy entertaining with direct access to side deck and darling enclosed sun porch. Convenient kitchen and bright breakfast nook lead to the backyard

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (860) 979-5591

    95 Shinar Mountain Rd, Washington Depot, CT 06794
  • /9

    $3,000 per month

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • House for Rent

    10 Old Farms Ln, New Milford, CT 06776

    Located in New Milford, this home is turnkey ready. Completely redone throughout including new vinyl flooring, updated kitchen, hardware, backsplash, new appliances. The 2 bedrooms are spacious with closet space, baseboard heating. Both bathrooms are completely new. If you are interested in a new rental, see this one in person, schedule your appointment today.

    10 Old Farms Ln, New Milford, CT 06776
  • /28

    $25,000 per month

    • 5 Beds
    • 8 Baths
    • 8,145 Sq Ft
    • House for Rent

    247 Roxbury Rd, Washington, CT 06793

    Luxury summer rental with inground Gunite pool in the beautiful Litchfield Hills of Washington. It's long gracious driveway leads you to the formal yet comfortable country house privately set on the property for peaceful enjoyment. This location is ideal, allowing easy access to Lake Waramaug, restaurants, an abundance of hiking and walking trails, wineries, breweries and New Preston Village for

    Maria Taylor Klemm Real Estate Inc

    247 Roxbury Rd, Washington, CT 06793
  • /14

    $1,750 per month

    • 1 Bed
    • 1 Bath
    • 1,500 Sq Ft
    • Apartment for Rent

    11 Partridge Ln, New Milford, CT 06776

    Enjoy peaceful country living in this spacious, unfurnished apartment located above a garage with a dedicated bay for your convenience. This unit includes a full kitchen, comfortable living area, bathroom, and a bedroom with a private deck overlooking a serene 10-acre parcel. Located just 5 minutes from New Milford Hospital and the charming downtown area, which features boutique shops and a

    Keith Evans William Raveis Real Estate

    11 Partridge Ln, New Milford, CT 06776
  • /28

    $20,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,089 Sq Ft
    • House for Rent

    5 North St, Roxbury, CT 06783

    Summer 2025: August at $20,000 per month. Inquire for alternate dates. Quintessential Litchfield County Retreat with Fabulous Gunite Pool in the Heart of the Town of Roxbury on 4 +/- pastoral acres. 4 bedroom and 2 and 1/2 bath charming Colonial with Great Room/Family Room with vaulted ceilings, Eat-in Country Kitchen, Formal Living Room with wood-burning fireplace, Formal Dining Room and a

    Melinda Dubow Klemm Real Estate Inc

    5 North St, Roxbury, CT 06783
  • /28

    $40,000 per month

    • 5 Beds
    • 8 Baths
    • 8,145 Sq Ft
    • House for Rent

    247 Roxbury Rd, Washington, CT 06793

    Luxury summer rental with inground Gunite pool in the beautiful Litchfield Hills of Washington. It's long gracious driveway leads you to the formal yet comfortable country house privately set on the property for peaceful enjoyment. This location is ideal, allowing easy access to Lake Waramaug, restaurants, an abundance of hiking and walking trails, wineries, breweries and New Preston Village for

    Maria Taylor Klemm Real Estate Inc

    247 Roxbury Rd, Washington, CT 06793
  • /17

    $4,500 per month

    • 7 Beds
    • 4 Baths
    • 2,940 Sq Ft
    • House for Rent

    8 Southbury Rd, Roxbury, CT 06783

    Wonderful opportunity to live in the heart of prestigious Roxbury in Litchfield County. Well preserved antique colonial filled with charm. Updates include kitchen, baths and open living area leading to primary bedroom. Brand new septic, 4 car garage with storage above and period outbuildings including a barn. Washer and dryer are located on the main level, upstairs bedrooms offer privacy for

    Lisa Titcomb William Pitt Sotheby's Int'l

    8 Southbury Rd, Roxbury, CT 06783
  • /27

    $2,700 per month

    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Townhouse for Rent

    10 Old Farms Ln, New Milford, CT 06776

    Located in New Milford, this home is turnkey ready. Completely redone throughout including new vinyl flooring, updated kitchen, hardware, backsplash, new appliances. The 2 bedrooms are spacious with closet space, baseboard heating. Both bathrooms are completely new. If you are interested in a new rental, see this one in person, schedule your appointment today.

    Daniel Reilly Coldwell Banker Realty

    10 Old Farms Ln, New Milford, CT 06776
  • /25

    $7,000 per month

    • 3 Beds
    • 3.5 Baths
    • 3,236 Sq Ft
    • House for Rent

    116 Wellers Bridge Rd, Roxbury, CT 06783

    Mid-Century single-level in a convenient Roxbury location. Cool mad-men vibe with floor to ceiling windows, exposed beams, vaulted ceilings, stone and wood floors, and wood paneling. Throughout the house the many windows pour natural light in and give fabulous views over the private and manicured grounds. The home has multiple versatile rooms giving a choice of layout to fit your needs. The

    Claudine McHugh Klemm Real Estate Inc

    116 Wellers Bridge Rd, Roxbury, CT 06783
  • /23

    $7,500 per month

    • 4 Beds
    • 3.5 Baths
    • 3,428 Sq Ft
    • House for Rent

    104 Lower Church Hill Rd, Washington, CT 06794

    This gorgeous light and bright Colonial has been recently renovated and is in a top-notch area of Washington. Just minutes from the town center, the beach area on Lake Waramaug and the 998-acre Steep Rock Preserve with hiking trails through the hills and along the riverbank. Additional nearby attractions include White Memorial State Park, Candlewood Lake, antique shops, restaurants, Winvian Spa,

    Maria Taylor Klemm Real Estate Inc

    104 Lower Church Hill Rd, Washington, CT 06794
  • /31

    $35,000 per month

    • 3 Beds
    • 3.5 Baths
    • 3,066 Sq Ft
    • House for Rent

    283 Woodbury Rd, Washington, CT 06793

    Single level furnished home available from July 4th through Labor Day for $35,000. 3-4 bedrooms on a well maintained property, which includes tennis court and heated gunite pool. Attached 2 car garage and outdoor play set. Conveniently located in Washington with access to restaurants and shops as well as Steep Rock.

    Pels Matthews W. Raveis Lifestyles Realty

    283 Woodbury Rd, Washington, CT 06793
  • /24

    $4,000 per month

    • 4 Beds
    • 3 Baths
    • 3,216 Sq Ft
    • House for Rent

    1497 Purchase Brook Rd, Southbury, CT 06488

    Welcome to this Spacious 3216 sq. ft. Colonial designed for comfort and enjoyment. Privately situated on 3+ acres. This home features a foyer opens to a formal living room with hardwood floors and fireplace, main level office or den that leads to an enclosed sunroom. Formal dining room with hardwood floors, bright custom kitchen, w/ss appliances and granite counters that opens to a solarium

    Delia Cianfagna William Raveis Real Estate

    1497 Purchase Brook Rd, Southbury, CT 06488
  • /27

    $15,000 per month

    • 3 Beds
    • 5 Baths
    • 3,888 Sq Ft
    • House for Rent

    34 Old Roxbury Rd, Roxbury, CT 06783

    Available for $15,000/mo for 2025/26 school year and $75,000 for Summer 2026. Enjoy Modern Luxury in Connecticut's Countryside. The meticulously renovated 4-bedroom residence seamlessly blends the original mid century architecture with contemporary sophistication. Enter on the main level with 2 bedrooms and 2 full baths, sauna, foyer, powder room and media room with large screen tv and bar.

    Stacey Matthews W. Raveis Lifestyles Realty

    34 Old Roxbury Rd, Roxbury, CT 06783
  • /32

    $10,000 per month

    • 3 Beds
    • 2.5 Baths
    • 2,762 Sq Ft
    • House for Rent

    24 Old Roxbury Rd, Roxbury, CT 06783

    Available school year 2025/2026 at $10,000/mo and Summer 2026 at $25,000/mo. Perched high on a scenic Roxbury hillside, this brand new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing

    Stacey Matthews W. Raveis Lifestyles Realty

    24 Old Roxbury Rd, Roxbury, CT 06783
  • /30

    $25,000 per month

    • 3 Beds
    • 3.5 Baths
    • 2,762 Sq Ft
    • House for Rent

    24 Old Roxbury Rd, Roxbury, CT 06783

    Available SUMMER 2026 at 75,000 total. Also, school year 2025/2026 at $10,000/mo. Perched high on a scenic Roxbury hillside, this brand new 3-bedroom home represents true luxury living. The architecture seamlessly integrates nature and light with huge walls of windows with retractable screens. The 2 embedded James Turrell light sculptures transform the living experience into an ever-changing

    Stacey Matthews W. Raveis Lifestyles Realty

    24 Old Roxbury Rd, Roxbury, CT 06783
  • /29

    $25,000 per month

    • 4 Beds
    • 6 Baths
    • 3,888 Sq Ft
    • House for Rent

    34 Old Roxbury Rd, Roxbury, CT 06783

    Available @ $25K for AUGUST 4 SEPT 3 2025. $15,000/mo for 2025/26 school year. Enjoy Modern Luxury in Connecticut's Countryside. The meticulously renovated 4-bedroom residence seamlessly blends the original mid century architecture with contemporary sophistication. Enter on the main level with 2 bedrooms and 2 full baths, sauna, foyer, powder room and media room with large screen tv and bar.

    Stacey Matthews W. Raveis Lifestyles Realty

    34 Old Roxbury Rd, Roxbury, CT 06783
  • /37

    $30,000 per month

    • 4 Beds
    • 2.5 Baths
    • 3,282 Sq Ft
    • House for Rent

    28 Leavenworth Rd, Woodbury, CT 06798

    STUNNING JUNE 1, 2025 - JULY 6, 2025 SUMMER RENTAL with POOL and TENNIS COURT (with lights). Enjoy a memorable month+ at this resort-style escape with newly renovated interior and incredible entertaining space indoors and out. Extraordinary cook's kitchen with breakfast nook opens into an expansive sun-filled room overlooking lawns, tennis court and pool. Updated bedrooms and bathrooms provide a

    Diana Bisselle William Pitt Sotheby's Int'l

    28 Leavenworth Rd, Woodbury, CT 06798
  • /37

    $25,000 per month

    • 4 Beds
    • 3.5 Baths
    • 2,200 Sq Ft
    • House for Rent

    76 North St, Roxbury, CT 06783

    Available Month of August at $25k. Spend a perfect summer month in this Gorgeous Connecticut Antique "Edson Bradley Estate," beautifully updated 3 bedroom antique home, with an additional 1 bedroom guest apartment in the nearby renovated barn, a gunite pool with views west, apple orchard and a lovely park-like setting. The 3 bedroom home main house offers open kitchen to Conservatory for great

    Kathryn Clair William Pitt Sotheby's Int'l

    76 North St, Roxbury, CT 06783
  • /30

    $4,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,632 Sq Ft
    • House for Rent

    29 Paper Mill Rd, Woodbury, CT 06798

    Completely furnished and ready for short term rentals until June 3rd and available as annual rental starting August 22nd. Historic 3 bedroom, 2.1 bath farmhouse set on a quiet country road. Exposed beams, wood floors and lots of light. Wrap around porch, stone walls, level lawn and gardens. Woodbury designated as Connecticut's "Most charming small town," by Reader's Digest offers tree-lined Main

    Claudine McHugh Klemm Real Estate Inc

    29 Paper Mill Rd, Woodbury, CT 06798
  • /40

    $10,000 per month

    • 3 Beds
    • 3.5 Baths
    • 5,154 Sq Ft
    • House for Rent

    6 Frisbie Rd, Washington, CT 06793

    AVAILABLE SEPT '25 - MAY '26 @ $10,000 PER MONTH. Quintessential CT Country Summer rental. Magnificent over-sized pool of 50' x 20' with spa, cabana with a full bathroom, changing room, kitchenette and outdoor grill. Pristine 3 bedroom 3.5 bath main house all bedrooms have king beds. The home is nestled on 21+ acres with new circular driveway, large expanses of lawn, mature trees. Gourmet

    Stacey Matthews W. Raveis Lifestyles Realty

    6 Frisbie Rd, Washington, CT 06793
  • /22

    $4,000 per month

    • 3 Beds
    • 2 Baths
    • 1,260 Sq Ft
    • House for Rent

    10 Sentry Hill Rd, Roxbury, CT 06783

    Upper three-bedroom, 2 bath now available from September 30, 2025. 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

    Melinda Dubow Klemm Real Estate Inc

    10 Sentry Hill Rd, Roxbury, CT 06783
  • /17

    $7,500 per month

    • 4 Beds
    • 2.5 Baths
    • 3,026 Sq Ft
    • House for Rent

    18 Bear Burrow Rd, Roxbury, CT 06783

    Charming barn-style home on 15.27 acres off quiet country road. Four bedrooms and two and one half baths. Open floor plan. Exposed timber. Double sided stone fireplace. French doors to rear patio. In ground pool and barrel sauna. The perfect summer retreat in the beautiful town of Roxbury. Available short term between September to May for $7,500 per month. Contact agent for availability. Just 90

    Maria Taylor Klemm Real Estate Inc

    18 Bear Burrow Rd, Roxbury, CT 06783
  • /25

    $18,900 per month

    • 4 Beds
    • 2.5 Baths
    • 1,782 Sq Ft
    • House for Rent

    23 Painter Hill Rd, Roxbury, CT 06783

    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. SUMMER June - August $18,900/month; OFF-SEASON September -

    Peter Klemm Klemm Real Estate Inc

    23 Painter Hill Rd, Roxbury, CT 06783
  • /13

    $24,900 per month

    • 1 Bed
    • 2 Baths
    • 900 Sq Ft
    • House for Rent

    253 Tophet Rd, Roxbury, CT 06783

    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. See listing for 253

    Peter Klemm Klemm Real Estate Inc

    253 Tophet Rd, Roxbury, CT 06783
  • /25

    $24,900 per month

    • 3 Beds
    • 3.5 Baths
    • 1,469 Sq Ft
    • House for Rent

    253 Tophet Rd, Roxbury, CT 06783

    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. SUMMER June -

    Peter Klemm Klemm Real Estate Inc

    253 Tophet Rd, Roxbury, CT 06783
  • /33

    $24,900 per month

    • 3 Beds
    • 2.5 Baths
    • 2,080 Sq Ft
    • House for Rent

    Unlisted Address

    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.

    Peter Klemm Klemm Real Estate Inc

    Unlisted Address
  • /22

    $30,900 per month

    • 3 Beds
    • 3.5 Baths
    • 4,251 Sq Ft
    • House for Rent

    45 Moosehorn Rd, Roxbury, CT 06783

    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. Many world class restaurants, inns

    Peter Klemm Klemm Real Estate Inc

    45 Moosehorn Rd, Roxbury, CT 06783
  • /30

    $30,900 per month

    • 6 Beds
    • 3.5 Baths
    • 2,716 Sq Ft
    • House for Rent

    33 Sentry Hill Rd, Roxbury, CT 06783

    Mint 6 bedroom colonial reproduction on scenic dirt road. Walk, jog, bike into land preserve. Heated pool, outdoor play set, bbq, 3 acre lawn, 4 wood-burning fireplaces. SUMMER:June - August $30,900/month. Memorial - Labor Day $74,900.OFF-SEASON: September - May $13,900/month If over 3 months, subtract $1,000 per month and no tax is due. ANNUAL:$169,000. Inquire about other/shorter rental terms.

    Peter Klemm Klemm Real Estate Inc

    33 Sentry Hill Rd, Roxbury, CT 06783
  • /25

    $26,900 per month

    • 4 Beds
    • 4 Baths
    • 2,396 Sq Ft
    • House for Rent

    247 Painter Hill Rd, Roxbury, CT 06783

    Mint St. Barth's-style home in perfect hilltop neighborhood with heated pool. Exceptional interior design with two wood burning fireplaces and vaulted ceilings. SUMMER June - August $26,900/month, Memorial - Labor Day $69,900. OFF-SEASON: September - May $12,900/month--If over 3 months, subtract $1,000 per month. And no tax is due. ANNUAL: $159,000. Inquire for other/shorter rental terms.

    Peter Klemm Klemm Real Estate Inc

    247 Painter Hill Rd, Roxbury, CT 06783
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