32

Homes for Rent near The Gunnery

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  • /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
  • /31

    $3,950 per month

    • 2 Beds
    • 2 Baths
    • 1,968 Sq Ft
    • House for Rent

    33 Washington Ave, Woodbury, CT 06798

    AVAILABLE FOR $3,950/MONTH. Stunning over-sized Cape on serene, park-like grounds adjacent to a nature preserve. Fully furnished, this inviting 2 bedroom home has been lovingly renovated with a great eye for detail. Quiet street centrally located in historic Woodbury. Newly finished hardwood oak flooring throughout. Two full bathrooms. The large living room with fireplace also includes a bright

    Agent Photo

    Rebecca Doh

    W. Raveis Lifestyles Realty

    (203) 872-6274

    33 Washington Ave, Woodbury, CT 06798
  • /51

    $2,100 per month

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft
    • Condo for Rent

    969 Purchase Brook Rd Unit 969 2nd floor, Southbury, CT 06488

    Immaculate first floor of a traditional two family New England colonial set on three private wooded acres and bordering State forest. This two family home is bright and cheerful, freshly painted and professionally cleaned top to bottom. Freshly finished hardwood floors throughout. Covered porch for sitting and barbequing. Beautifully landscaped grounds, plenty of parking and huge new country

    969 Purchase Brook Rd Unit 969 2nd floor, Southbury, CT 06488
  • /25

    $2,300 per month

    • 2 Beds
    • 2 Baths
    • 1,044 Sq Ft
    • House for Rent

    114 Heritage Village Unit E, Southbury, CT 06488

    Indulge in the epitome of pride of ownership within the highly coveted active adult 55+ community of Heritage Village. Nestled serenely, this meticulously maintained 2-bedroom, 2-bathroom unit offers a retreat from the bustle, with a picturesque view of the golf course gracing your private deck adjacent to the living room. Inside, hardwood floors exude timeless elegance while built-in shelving

    Camilo Ramirez Higgins Group Real Estate

    114 Heritage Village Unit E, Southbury, CT 06488
  • /20

    $4,950 per month

    • 4 Beds
    • 4.5 Baths
    • 7,112 Sq Ft
    • House for Rent

    259 Main St S, Woodbury, CT 06798

    Property Id: 1500786Located on Main Street South in the heart of Woodbury, in the Litchfield Hills this main house offers 4 BR, 4.5 baths and features original architectural elements, ample living space and beautiful outdoor space. The main living area has a half bath, EIK with island, SS appliances and door to side deck for outdoor eating and grilling + private courtyard, professionally

    259 Main St S, Woodbury, CT 06798
  • /9

    $1,500 per month

    • 1 Bath
    • 400 Sq Ft
    • House for Rent

    404 Nettleton Hollow Rd Unit A, Washington, CT 06793

    $1500 PER MONTH.. Amazing location, just across from Land Trust. Annual Unfurnished Studio Apartment above the garage at "Red Studio Farm." Located in the scenic and historic Nettleton Hollow area of Washington and just 90 minutes from NYC! Wonderful western exposure for sunsets and views over nearby meadows and pond. The apartment has great room with cathedral ceiling, sleeping loft, full bath

    John Sniffen William Pitt Sotheby's Int'l

    404 Nettleton Hollow Rd Unit A, Washington, CT 06793
  • /15

    $2,800 per month

    • 2 Beds
    • 2 Baths
    • 1,398 Sq Ft
    • House for Rent

    1023 Heritage Village Unit B, Southbury, CT 06488

    This is a Country House rental with two bedrooms and an oversized deck. It has some steps and a walk but if you are looking for privacy this is for you. Located in the fifty five plus community of Heritage Village in Southbury. Get up close and comfortable with great shopping and dining right in town.

    Bonnie Wilson Berkshire Hathaway NE Prop.

    1023 Heritage Village Unit B, Southbury, CT 06488
  • /40

    $6,500 per month

    • 4 Beds
    • 4.5 Baths
    • 4,278 Sq Ft
    • House for Rent

    2 Landmark Dr, Bridgewater, CT 06752

    2 Landmark Drive, and its 2 picturesque acres, offers a perfect blend of luxury and comfort. Set in Landmark Estates, a premiere lakefront community in Bridgewater known for its beautiful scenery and access to Lake Lillinonah, is a small, serene community located near the Brookfield border. This furnished 4,278 sq ft home has gleaming hardwood floors throughout. Through the lg entrance w/dbl coat

    William Piccirillo BHGRE Gaetano Marra Homes

    2 Landmark Dr, Bridgewater, CT 06752
  • /28

    $7,000 per month

    • 5 Beds
    • 2.5 Baths
    • 3,873 Sq Ft
    • House for Rent

    64 Riverford Rd, Brookfield, CT 06804

    Welcome to 64 Riverford Rd, a fully furnished 5-bedroom, 3-bathroom rental home in Brookfield, CT, perfect for short-term or mid-term rental stays. This spacious property combines modern comfort with resort-style amenities, making it ideal for families, executive relocations, or anyone seeking turnkey housing in Fairfield County. The home features multiple living areas, a well-equipped kitchen,

    Chelsea Stinson Coldwell Banker Realty

    64 Riverford Rd, Brookfield, CT 06804
  • /8

    $2,200 per month

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

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

    Available January, 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

    Melinda Dubow Klemm Real Estate Inc

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

    $6,000 per month

    • 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
  • /16

    $3,300 per month

    • 2 Beds
    • 2 Baths
    • 1,290 Sq Ft
    • House for Rent

    36 Washington Ave, Woodbury, CT 06798

    Charming 2-Bed 2 Bath single family home rental in the heart of Woodbury, and only 90 minutes from NYC! Over 1290 sf and has LR with fireplace, updated kitchen with large dining area, two large bedrooms, 2 full baths and there is also a bonus family room area and laundry area in the lower level. CentralAir throughout. Outdoor living includes an in-ground pool, deck and covered porch. Walking

    Sharon Rinaldi Showcase Realty, Inc.

    36 Washington Ave, Woodbury, CT 06798
  • /29

    $4,000 per month

    • 3 Beds
    • 2 Baths
    • 2,064 Sq Ft
    • House for Rent

    12 Spring St, Woodbury, CT 06798

    Welcome to this beautifully maintained 3-bedroom, 2-bath Victorian offering just over 2,000 sq. ft. of elegant living space. This home perfectly blends original architectural details with modern conveniences and boasts abundant natural light. Inside, the spacious living room and formal dining room create a warm and inviting atmosphere. The main level also features a large, versatile office-ideal

    Rhya Szymansky Drakeley Real Estate, Inc.

    12 Spring St, Woodbury, CT 06798
  • /21

    $4,400 per month

    • 4 Beds
    • 2.5 Baths
    • 2,336 Sq Ft
    • House for Rent

    38 W Mountain Ln, Roxbury, CT 06783

    Located on a quiet private road in Roxbury, this open concept, four bedroom home is awaiting its new tenants. Get in before the end of the summer and beginning of the school year, nothing to do but move in! With recently refinished floors and new appliances, this neat and clean home offers three bathrooms, plenty of privacy, large basement for storage and detached two car garage. Good credit a

    Katherine Parlato Drakeley Real Estate, Inc.

    38 W Mountain Ln, Roxbury, CT 06783
  • /33

    $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 $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
  • /26

    $4,600 per month

    • 4 Beds
    • 2.5 Baths
    • 2,165 Sq Ft
    • House for Rent

    408 Hut Hill Rd, Bridgewater, CT 06752

    Welcome to 408 Hut Hill Road, where timeless charm meets modern convenience in this beautifully reimagined 4-bedroom, 2.5-bath home. Set on a peaceful country road in desirable Bridgewater, this home has been completely renovated from top to bottom. Enjoy cooking and entertaining in the brand-new custom kitchen, featuring stylish cabinetry, stainless steel appliances, and quartz countertops.

    Katharine Kubisek Coldwell Banker Realty

    408 Hut Hill Rd, Bridgewater, CT 06752
  • /37

    $6,500 per month

    • 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

    $15,000 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
  • /28

    $20,000 per month

    • 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 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

    • 4 Beds
    • 6 Baths
    • 3,996 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
  • /36

    $15,000 per month

    • 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 per month

    • 4 Beds
    • 6 Baths
    • 3,996 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
  • /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, 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 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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