30

Homes for Rent near The Frederick Gunn School

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  • /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
  • /33

    $4,200 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
  • /22

    $3,300 total monthly price

    • 4 Beds
    • 2.5 Baths
    • 1,936 Sq Ft
    • House for Rent

    256 Baldwin Hill Rd, New Preston Marble Dale, CT 06777

    Embrace the quintessential New England lifestyle in this classic and elegantly presented one-level home, nestled in the vibrant village of New Preston. The heart of the home is a spacious kitchen and Dining Room that effortlessly opens into a welcoming living room. It features a cozy stone fireplace and has ample space to accommodate a baby grand piano. Direct access to a private patio provides a

    Samantha Behm William Pitt Sotheby's Int'l

    256 Baldwin Hill Rd, New Preston Marble Dale, CT 06777
  • /24

    $3,950 total monthly price

    • 3 Beds
    • 2.5 Baths
    • 3,000 Sq Ft
    • House for Rent

    64 Big Bear Hill Rd, New Milford, CT 06776

    Lake front guest house on exquisite estate in New Milford. Nestled on a 100 acre parcel and overlooking a 15 acre lake with stunning views. Updated throughout including hardwood oak floors , stainless-steel appliances, resurfaced wood kitchen cabinets ,and partially finished lower level with double doors leading to natural wonderland. The eat in kitchen has two sky lights and opens to an

    Larry Corrow Coldwell Banker Realty

    64 Big Bear Hill Rd, New Milford, CT 06776
  • /12

    $1,300 total monthly price

    • 1 Bath
    • 800 Sq Ft
    • House for Rent

    175 Arch Bridge Rd Unit D, Bethlehem, CT 06751

    Chic and spacious 2 room studio in a newer contemporary farmhouse building. A stones throw to Washington, Woodbury for private schools events or an abundance of fabulous retusraunts and shops. Nice outdoor space on your expansive private deck. Assigned parking and a space out of the weather. The perfect space on an expansive parcel of land. $250 flat fee per month for Utilities.

    Jeff Boucher Drakeley Real Estate, Inc.

    175 Arch Bridge Rd Unit D, Bethlehem, CT 06751
  • /6

    $2,150 total monthly price

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

    231 Romford Rd, Washington Depot, CT 06794

    Super charming single-level cottage in Washington available January 1. Unfurnished, minimum 12 month lease, pets case by case. This welcoming cottage is the guest house of a beautiful estate on Romford Road, very near Rumsey Hall. Washer/Dryer, private driveway and parking, standby generator. Minutes from Washington Depot, New Preston, and Bantam; access to Lake Waramaug at the Washington Town

    William Bolls Compass Connecticut, LLC

    231 Romford Rd, Washington Depot, CT 06794
  • /29

    $13,900 total monthly price

    • 3 Beds
    • 6 Baths
    • 4,166 Sq Ft
    • House for Rent

    45 Calhoun St, Washington Depot, CT 06794

    Magnificent country home, pool, and spa on coveted Calhoun Street. 15 private acres of stone terraces, gardens, fruit trees, fields, extraordinary views, only 1 mile from town. Close to New Preston and Lake Waramaug. 4-6 bedroom Dutch Colonial with LR, DR, Library, Chef's Kitchen with large dining area, Large Pantry, Den and 3 full and 3 half bathrooms, 4 Fireplaces, 2-Car Garage. SUMMER June -

    Peter Klemm Klemm Real Estate Inc

    45 Calhoun St, Washington Depot, CT 06794
  • /18

    $3,800 total monthly price

    • 4 Beds
    • 3 Baths
    • 1,821 Sq Ft
    • House for Rent

    41 Hipp Rd, New Milford, CT 06776

    Welcome to Hipp Road! This antique farmhouse is perfectly positioned between the charm of Washington Depot and New Milford Green-offering the best of both worlds in coveted Litchfield County. The property seamlessly blends wonderful original character and period details with thoughtfully updated modern comforts throughout. The flexible floor plan features your choice of a primary en suite on the

    Christian Jensen William Pitt Sotheby's Int'l

    41 Hipp Rd, New Milford, CT 06776
  • /11

    $1,500 total monthly price

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

    74 Belair Dr, New Milford, CT 06776

    Spacious 1 bedroom Belair rental on the first floor! Some work in progress to make this in move in condition. Large living room, eat-in kitchen & 2 entry doors in the unit, along with a convenient reserved parking space. Common laundry is right across the hall and a good location along the HART bus line!

    Lori Campbell Coldwell Banker Realty

    74 Belair Dr, New Milford, CT 06776
  • /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

    Whole House Now available from May 2026 at $6,000. 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

    Melinda Dubow Klemm Real Estate Inc

    10 Sentry Hill 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
  • /34

    $6,900 total monthly price

    • 3 Beds
    • 3.5 Baths
    • 3,795 Sq Ft
    • House for Rent

    61 Old Litchfield Rd, Washington, CT 06793

    Fantastic Washington winter rental. Available 11/15/2025 thru 4/30/2026. Close to town, schools and SteepRock. 3 Bedrooms, 3.5 bathroom Dutch colonial style home. Eat in kitchen, dining room, living room, office and primary bedroom on main floor. 2 Beds and 2 baths with second work area upstairs. Finished basement areas. Great yard and western sunsets. Perfect for ski season at Mohawk Mountain.

    Pels Matthews W. Raveis Lifestyles Realty

    61 Old Litchfield 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
  • /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
  • /39

    $7,000 total monthly price

    • 3 Beds
    • 3 Baths
    • 1,602 Sq Ft
    • House for Rent

    23 Cook St, Washington Depot, CT 06794

    This charming country Cape in the heart of Washington Depot is now available for rent after a considerable remodel. The home sits on just under 2 acres in a quiet setting, yet is walking distance from the center of town. Each of the main level's rooms are bright and well sized. The eat-in kitchen features marble counters, stainless steel appliances, a breakfast nook, and is adjacent to the dining

    Matt McElhone William Pitt Sotheby's Int'l

    23 Cook St, Washington Depot, CT 06794
  • /30

    $6,000 total monthly price

    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft
    • House for Rent

    25 Sandstrom Rd, New Preston Marble Dale, CT 06777

    Have yourself an easy breezy summer with this charming 3 bedroom/2 full bath Cottage within walking distance of Lake Waramaug! The house is perched on a knoll on a quiet country road with a beautiful patio for entertaining. An open floor plan on the main floor has a dining room and living room with a fireplace. Main floor also consists of the primary bedroom, renovated full bath, chef's kitchen

    Judith Auchincloss Klemm Real Estate Inc

    25 Sandstrom Rd, New Preston Marble Dale, CT 06777
  • /22

    $3,500 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 February 2026 @ $3500. 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

    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
  • /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
  • /36

    $14,900 total monthly price

    • 7 Beds
    • 9 Baths
    • 15,000 Sq Ft
    • House for Rent

    10 Sunny Ridge Rd, Washington, CT 06793

    Major estate with the highest standards of construction located within the Sunny Ridge historic district. Situated on 10 private, park-like acres with an over-sized heated pool, fabulous stonewalls, giant dining terraces, pond and orchard. 7+ bedrooms, Billiard room, screening room, paneled library, sunroom, new country kitchen, 100-person party room boasts a restaurant size bar, sound system and

    Peter Klemm Klemm Real Estate Inc

    10 Sunny Ridge Rd, Washington, CT 06793
  • /12

    $12,900 total monthly price

    • 4 Beds
    • 2 Baths
    • 1,720 Sq Ft
    • House for Rent

    47 Calhoun St, Washington Depot, CT 06794

    Charming mint renovated Nantucket-style cottage set on 25 acres of meadows with apple trees and 200-year old maples. Breathtaking hilltop views overlook farms, the Town of Washington and church steeples. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.SUMMER June - August $26,900/month; Memorial - Labor Day $69,900; OFF-SEASON

    Peter Klemm Klemm Real Estate Inc

    47 Calhoun St, Washington Depot, CT 06794
  • /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
  • /20

    $10,900 total monthly price

    • 2 Beds
    • 2 Baths
    • 2,153 Sq Ft
    • House for Rent

    17 Kirby Rd, Washington, CT 06793

    Pristine Arts & Crafts Carriage House. Perfect setting on Washington's Historic Green surrounded by the Frederick Gunn School and historic shingle-style Rossiter mansions. Ground floor ensuite primary bedroom, office with sleeper sofa and cozy den with wood-burning fireplace. Upstairs, king bedroom with ensuite bath, large living room, dining room and eat-in kitchen. Fabulous mahogany deck for

    Peter Klemm Klemm Real Estate Inc

    17 Kirby Rd, Washington, CT 06793
  • /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
  • /14

    $11,900 total monthly price

    • 3 Beds
    • 3 Baths
    • 1,933 Sq Ft
    • House for Rent

    110 Shearer Rd, Washington, CT 06793

    Restored country cottage furnished with antiques, fine furnishings & oriental rugs. New gunite in-ground pool and terrace. Wonderful scenic dirt road walking or bike riding through historic estate neighborhood. Relax or dine with a bbq on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea.SUMMER June - August $24,900/month; Memorial - Labor Day

    Peter Klemm Klemm Real Estate Inc

    110 Shearer Rd, Washington, CT 06793
  • /16

    $13,900 total monthly price

    • 4 Beds
    • 3 Baths
    • 3,530 Sq Ft
    • House for Rent

    51 Senff Rd, Washington, CT 06793

    Pristine 5-bedroom private home on scenic dirt road ideal for walking, jogging and biking. Magnificent design with 2 gas fireplaces and filled with the art of Thomas McKnight. 2 over-sized wood decks overlooking the heated pool surrounded by endless summer hydrangea and 3 acres of lawns. The perfect location minutes from the center of Washington, the Mayflower and Winrian Inns & Spas.SUMMER:June

    Peter Klemm Klemm Real Estate Inc

    51 Senff Rd, Washington, CT 06793
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