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Homes for Rent near Booth Free School

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  • /33

    $5,000 total monthly price

    • 3 Beds
    • 2 Baths
    • 1,088 Sq Ft
    • House for Rent

    13 South St, Washington, CT 06793

    This beautifully updated 3-bedroom, 2-bath ranch offers the perfect blend of comfort and convenience-ideal as a weekend retreat or a year-round home. Located just minutes from the renowned Mayflower Inn & Spa and the Frederick Gunn School, and only two hours from NYC, the location is unbeatable. Enjoy a brand-new kitchen featuring quartz countertops, custom cabinetry, and stainless steel

    Agent Photo

    Gary Crawford

    RE/MAX RISE

    (860) 909-8487

    13 South St, Washington, CT 06793
  • /14

    $2,500 total monthly price

    • 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
  • /13

    $1,450 total monthly price

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

    15 Fordyce Ct, New Milford, CT 06776

    Rare 1st floor- No stairs large 1 BR clean, open apartment, with laundry and storage across hall. View of horse farm, Housatonic River, sunsets & distant commercial lights of Rte 7. Must have good credit. Proof of income-W2. R-I ratio =$58K+. No pet, no cosigner.

    Ann Muoio William Raveis Real Estate

    15 Fordyce Ct, New Milford, CT 06776
  • /24

    $2,100 total monthly price

    • 2 Beds
    • 1 Bath
    • 2,841 Sq Ft
    • House for Rent

    141 Washington Rd Unit 2, Woodbury, CT 06798

    Beautifully Renovated 2-Bedroom Apartment in Woodbury, CT Welcome to your newly renovated 2-bedroom, 1-bath apartment located in the heart of Woodbury. This top floor, bright and inviting apartment blends modern updates with charming character details, including exposed wood beams and warm, wood-style flooring throughout. The brand-new kitchen features crisp white shaker cabinets, quartz

    Dean Giatas Fiorelli Realty, LLC

    141 Washington Rd Unit 2, Woodbury, CT 06798
  • /15

    $1,900 total monthly price

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

    199 Hoop Pole Hill Rd, Woodbury, CT 06798

    Garden apartment - complete with private firepit and picnic table. Tend to your own gardens until your hearts content! (not required - just a privilege if you choose). Freshly deep cleaned and painted and ready for new occupants. One very large bedroom with bow window and book shelves, has been used in the past as combined LR and BR space, it's that big! Eat in kitchen leaves plenty of room for a

    Mary Ann Bennett Drakeley Real Estate, Inc.

    199 Hoop Pole Hill Rd, Woodbury, CT 06798
  • /11

    $1,800 total monthly price

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

    151 Washington Ave, Woodbury, CT 06798

    Immediate occupancy available - utilities included! Super clean- super bright. Remodeled ranch unit on the lower level of residential home - above grade for natural light! Winding stone steps down from large parking area leads to a private patio to enjoy the seasons and the lush green lawn. Looking to find tenants who enjoy quiet and co exist w other residents on the same property. Laundry &

    Mary Ann Bennett Drakeley Real Estate, Inc.

    151 Washington Ave, Woodbury, CT 06798
  • /15

    $2,500 total monthly price

    • 2 Beds
    • 1.5 Baths
    • 1,058 Sq Ft
    • Townhouse for Rent

    17 Old Farms Ln Unit 17, New Milford, CT 06776

    Freshly painted and renovated unit that is bright and spacious. Three levels of living space. The main floor has a kitchen, living room, dining area and half bathroom. The upper level has 2 large bedrooms and a full bath. Downstairs is a large family room with a slider to a private patio and walkway to the car-port. The laundry room is also downstairs.

    Tama Murphy Keller Williams Realty

    17 Old Farms Ln Unit 17, New Milford, CT 06776
  • /33

    $3,500 total monthly price

    • 4 Beds
    • 3 Baths
    • 3,063 Sq Ft
    • House for Rent

    510 Good Hill Rd, Woodbury, CT 06798

    Rare opportunity to lease this c.1848 Farmhouse, set just steps from the Roxbury/Woodbury town line and overlooking the Roxbury Land Trust. Annual lease for unfurnished 10-room home offering timeless charm, sweeping views from every angle, and modern comfort. Inside, enjoy 4 bedrooms, 3 full baths, laundry on the main floor, wood burning stove and 1 fireplace. The home features a symmetrical

    Robert Pendilla W. Raveis Lifestyles Realty

    510 Good Hill Rd, Woodbury, CT 06798
  • /8

    $2,200 total monthly price

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

    10 (LOWER) Sentry Hill Rd, Roxbury, CT 06783

    Available May 2026: $2,200 plus utilities per month. 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 1 bedroom/1 bath apartment, is located beneath the main house and may be rented with the main house(Upstairs 3-bedroom) or completely

    Melinda Dubow Klemm Real Estate Inc

    10 (LOWER) Sentry Hill Rd, Roxbury, CT 06783
  • /28

    $6,000 total monthly price

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

    10 Sentry Hill Rd, Roxbury, CT 06783

    Now available from January 2026. 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 4-bedroom, 3 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

    Melinda Dubow Klemm Real Estate Inc

    10 Sentry Hill Rd, Roxbury, CT 06783
  • /39

    $25,000 total monthly price

    • 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 $15,000/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
  • /31

    $3,500 total monthly price

    • 3 Beds
    • 2 Baths
    • 2,029 Sq Ft
    • House for Rent

    359 Nettleton Hollow Rd, Washington, CT 06793

    Discover a truly special place where creativity and serenity thrive. Tucked away on 3.28 acres of private woodland, this stunning residence invites you to live immersed in nature's embrace while enjoying all the comforts of a thoughtfully designed home. The property unfolds like a sanctuary-featuring a peaceful park-like setting with a pond that welcomes migrating waterfowl and transforms into a

    Brandy Granata Coldwell Banker Realty

    359 Nettleton Hollow Rd, Washington, CT 06793
  • /23

    $7,500 total monthly price

    • 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
  • /37

    $5,500 total monthly price

    • 4 Beds
    • 4 Baths
    • 4,000 Sq Ft
    • House for Rent

    28 Old Ln, Roxbury, CT 06783

    Tucked into the hills of Roxbury, this 4,000 sq ft Mid-Century Modern home is a private architectural retreat surrounded by wildflower clearings, forest, and dramatic granite outcroppings. The property exudes rustic country charm, favoring natural beauty over manicured formality. Inside, cathedral ceilings with numerous skylights create an airy, light-filled space that blurs the line between

    Robert Barker Houlihan Lawrence WD

    28 Old Ln, Roxbury, CT 06783
  • /28

    $12,500 total monthly price

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

    247 Roxbury Rd, Washington, CT 06793

    Luxury 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
  • /28

    $20,000 total monthly price

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

    5 North St, Roxbury, CT 06783

    Summer 2026: July and/or 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

    Melinda Dubow Klemm Real Estate Inc

    5 North St, Roxbury, CT 06783
  • /25

    $7,000 total monthly price

    • 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
  • /27

    $15,000 total monthly price

    • 4 Beds
    • 6 Baths
    • 3,996 Sq Ft
    • House for Rent

    34 Old Roxbury Rd, Roxbury, CT 06783

    Available for $15,000/mo for April and May, 2026 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
  • /38

    $15,000 total monthly price

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

    24 Old Roxbury Rd, Roxbury, CT 06783

    Available school year 2025/2026 at $15,000/mo and Summer 2026 at $25,000/mo. Perched high on a scenic Roxbury hillside, this 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 meditation on

    Stacey Matthews W. Raveis Lifestyles Realty

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

    $25,000 total monthly price

    • 4 Beds
    • 6 Baths
    • 3,996 Sq Ft
    • House for Rent

    34 Old Roxbury Rd, Roxbury, CT 06783

    Available @ $25K per month for Summer 2026. $15,000/mo for April & May 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
  • /22

    $4,000 total monthly price

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

    10 Sentry Hill Rd, Roxbury, CT 06783

    Upper three-bedroom, two bath now available from January 2026. 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

    Melinda Dubow Klemm Real Estate Inc

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

    $7,500 total monthly price

    • 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
  • /13

    $10,900 total monthly price

    • 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

    $12,900 total monthly price

    • 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
  • /33

    $11,900 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
  • /25

    $11,900 total monthly price

    • 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
  • /25

    $12,900 total monthly price

    • 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
  • /22

    $13,900 total monthly price

    • 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

    $13,900 total monthly price

    • 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
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