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Roxbury, CT Homes for Rent

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  • /30

    $2,500 per month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • House for Rent

    152 Baker Rd Unit Cabin, Roxbury, CT 06783

    This charming country log cabin, beautifully renovated in 2024, offers a serene escape perfect for years of enjoyment. The kitchen boasts new cabinetry, stainless steel appliances, and a pantry, ideal for culinary enthusiasts. A cathedral ceiling in the main living area is enhanced by a cozy gas fireplace, creating a warm ambiance. Off the primary bedroom you will fine a large bay window and

    Pam Famiglietti William Raveis Real Estate

    152 Baker Rd Unit Cabin, Roxbury, CT 06783
  • /30

    $2,950 per month

    • 2 Beds
    • 1 Bath
    • 768 Sq Ft
    • House for Rent

    152 Baker Rd Unit Cabin, Roxbury, CT 06783

    This charming country log cabin, beautifully renovated in 2024, offers a serene escape perfect for years of enjoyment. The kitchen boasts new cabinetry, stainless steel appliances, and a pantry, ideal for culinary enthusiasts. A cathedral ceiling in the main living area is enhanced by a cozy gas fireplace, creating a warm ambiance. The large bay window and sliding doors open to a private back

    Pam Famiglietti William Raveis Real Estate

    152 Baker Rd Unit Cabin, Roxbury, CT 06783
  • /16

    $1,750 per month

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

    154 Baker Rd Unit 2nd fl, Roxbury, CT 06783

    This beautifully renovated studio apartment, set in a tranquil environment, promises years of enjoyment. Recently updated in 2024, it features new stainless-steel appliances and a convenient combo washer/dryer. The gleaming hardwood floors and sparkling new bathroom add a touch of elegance. The bedroom area includes a double closet and access to a walk-up attic for extra storage. Heat is included

    Pam Famiglietti William Raveis Real Estate

    154 Baker Rd Unit 2nd fl, Roxbury, CT 06783
  • /19

    $12,000 per month

    • 3 Beds
    • 2.5 Baths
    • 1,571 Sq Ft
    • House for Rent

    19 Spargo Rd, Roxbury, CT 06783

    Mid Century Modern Retreat Available for May and June, 90 Minutes from NYC in beautiful Roxbury, CT. Renovated 3 bedroom, 2.5 bath tucked away on almost 5 acres and a quiet road. With heated gunite pool, mature landscaping and gardens. Soak up the sun poolside or on the deck, complemented by Sonos streaming inside and out. Light shines into the living room with wood-burning fireplace, vaulted

    William Bolls Compass Connecticut, LLC

    19 Spargo Rd, Roxbury, CT 06783
  • /15

    $4,800 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
  • /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
  • /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 2025. 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 2025 at $75,000 and 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 inbedded screens. The two embedded James Turrell light sculptures transform the living experience into an ever-changing meditation

    Stacey Matthews W. Raveis Lifestyles Realty

    24 Old Roxbury Rd, Roxbury, CT 06783
  • /28

    $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 2025 at $75,000 and 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 inbedded screens. The two 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 per month

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

    34 Old Roxbury Rd, Roxbury, CT 06783

    Available for $75,000 for Summer 2025 and $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
  • /27

    $10,000 per month

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

    5 North St, Roxbury, CT 06783

    Summer 2025: June @ $10,000 per month. July and/or August at $13,000 per month. Inquire for alternate dates. Quintessential Litchfield County Retreat with Fabulous Heated 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

    Melinda Dubow Klemm Real Estate Inc

    5 North St, Roxbury, CT 06783
  • /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
  • /20

    $10,000 per month

    • 2 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • House for Rent

    37 South St, Roxbury, CT 06783

    Summer 2025: June $1ok; July $12k; August $12k. Utterly Charming In-Town Delight with New Heated Pool. 2 Bedroom, 2.5 Bath Main House + 1 Bedroom, 1 Bath Guest House with Separate Kitchen. Moments From Library, General Store & Town Tennis Courts. Inviting Eat-in Kitchen with Dining & Seating Area. Separate Formal Dining Room. Large Living Room with Fireplace. 2 En-Suite Bedrooms. Brand New Pool

    Graham Klemm Klemm Real Estate Inc

    37 South St, Roxbury, CT 06783
  • /22

    $4,000 per month

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

    10 Sentry Hill Rd, Roxbury, CT 06783

    Huge Price Adjustment for Summer 2025: $4,450 per month plus utilities. INQUIRE for off-season or longer terms. 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

    Melinda Dubow Klemm Real Estate Inc

    10 Sentry Hill Rd, Roxbury, CT 06783
  • /40

    $32,500 per month

    • 4 Beds
    • 4.5 Baths
    • 3,680 Sq Ft
    • House for Rent

    35 Schoolhouse Rd, Roxbury, CT 06783

    Deluxe SUMMER 2025 furnished rental. AVAILABLE $32,500/MONTH or JUNE 28- AUG 14 @ $45,000. Fabulous location in estate area of Roxbury on a quiet single lane road yet minutes to town or Mayflower Inn, shopping etc. 4 bedrooms all en suite in main house as well as 2 washers and 2 dryers, a steam shower, an electric oven and gas range, 3 refrigerators and a wine cooler. The 1 bed guest house has a

    Rebecca Doh W. Raveis Lifestyles Realty

    35 Schoolhouse Rd, Roxbury, CT 06783
  • /14

    $2,500 per month

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

    160 North St, Roxbury, CT 06783

    SHORT TERM RENTAL AVAILABLE @ $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.

    Rebecca Doh W. Raveis Lifestyles Realty

    160 North St, 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

    $26,900 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 $26,900/month; Memorial - Labor Day Main

    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
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    $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

About Roxbury

Just a few miles east of Bridgeport, in western Connecticut's Litchfield Hills, sits the town of Roxbury, a rural area spread over 27 square miles with a population just over 2,000. That low population density means that residents here can appear somewhat isolated from the creature comforts associated with urban living, but that’s exactly how they like it. “People move to Roxbury because it’s quiet,” says local Realtor Stephanie Blake of Realty ONE Group Connect. “The rural nature of the town is its real appeal. At the same time, though, it’s c ...

Frequently Asked Questions

What are the most popular neighborhoods in Roxbury, CT for renters?
The most popular neighborhoods in Roxbury, CT for renters are Oxford and Downtown Waterbury.
What are the most popular zip codes in Roxbury, CT for renters?
The most popular zip codes in Roxbury, CT for renters include 06511, 06010, 06810, 06776 and 06790.
How to Rent a Home