Flexible Term Rental: Experience the charm of a beautifully maintained Colonial reproduction set on 4.5 acres. This 2,700 sq ft gem features four spacious bedrooms, including a master suite with a sweetheart balcony and en suite bathroom, and a fireplace-adorned secondary bedroom. Enjoy the warmth of wood-burning fireplaces in the formal dining room, living room, and den. The kitchen shines with granite countertops, stainless appliances, and skylights. The property boasts pinewood flooring, elegant paneling, a full basement with extensive storage, and a two-bay garage with unique tractor storage. Relish the outdoor beauty from an elevated deck overlooking a level lawn and mature landscaping. Prime location near Roxbury Land Trust, Maple Bank Farm, Mayflower Inn, and Woodbury's dining.

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 June 15th to August 2nd for $22,000 per month. Just 90 minutes from NYC. Also available from Labor Day to Memorial Day for $7,500 per month.

Set in one of the most beautiful areas of Roxbury and short walk to acres of land trust, this light, bright and airy open floor plan 18th century Colonial has over 26 acres of peace and quiet. There is a large tranquil pond which is surrounded by white pine trees. A place to one with nature! The home features 2 primary bedrooms, one on each level and an additional bedroom on the second level. The designer kitchen with Carrara marble counters, a vaulted ceiling and custom island opens to a stone patio and screened porch. The huge living room is light filled with wide board floors, French doors and a wood burning fireplace. This home also features central air conditioning, a security system, first floor laundry. Enjoy the sites and sounds of nature in this very special retreat property and relax in this paradise, under 2 hours from New York City.

Enjoy Summer in Roxbury at this delightful 3BDR, 2 Bath cottage with pool. Light and bright interior with easy-living, one-level floor plan. Enjoy the morning sunrise and beautiful light throughout the day, and soak in the captivating sunsets from the trellised deck or poolside. In the words of Debussy..."there is nothing more musical than a sunset" and the long western views will not disappoint. Let your eyes wander across the beautifully manicured verdant lawns, providing a sense of both peace and privacy. This property is the perfect escape from city life but also allows one to venture out to local attractions: Refresh at the Roxbury Falls, enjoy local fairs and art galleries, hike at Roxbury land trust, or try tennis, horseback riding and golf nearby. Shop at local Farmers markets and farm stands or go antiquing in neighboring Woodbury. Choose from a broad spectrum of dining options from farm to table to Michelin star restaurants. Just 1.5 hours from NYC. AVAILABLE: JUNE, JULY and/or AUGUST 2024. Tenant is responsible for cost of pool heat.

Impeccably renovated and beautifully furnished turnkey rental. This super stylish two bedroom home is hidden down a long driveway, yet located in the heart of Roxbury, just minutes to the conveniences of Washington Depot. The sophisticated renovation and design is complimented by big picture windows, high ceilings, and a wood burning fireplace. Luxuriously furnished with a collection of iconic modernist designs, this is country living at its finest. Enjoy the peaceful and private 9.5 acre grounds, complete with hiking trails and a private lookout with sweeping views of Painter Ridge. Owner/Broker.

Located on a quiet private road in Roxbury, this open concept, four bedroom home is awaiting its new tenants. Previous long term tenants absolutely loved the home. Get in before the summer and 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 must, no smoking, and pets ok with owner approval. Enjoy all that this quaint town has to offer!

AVAILABLE July 1st - July 31st, 2024 @ $22,500 plus expenses. 1840 Greek Revival farmhouse decorated with fantastic antiques and artwork selected by leading New York City interior designer. Chef's kitchen with breakfast room and French doors that walk out to back lawn. Great room with dining table that seats 10 and 2 sitting areas. Spacious office. Heated in-ground pool sits within beautiful grounds connected to hiking trails in the Roxbury Land Trust's Lilly Preserve. Renovated pool house with gym equipment. Tenant responsible for utilities, weekly pool maintenance, lawn care and house keeping. Landlord responsible for additional gardening and alarm service.

Terrific Roxbury Summer Rental: Modern, renovated 3 bedroom, 2.5 bath located on a quiet road and almost 5 peaceful acres. Inground heated pool, mature landscaping and perennial gardens. Soak up the sun poolside or on the deck, and enjoy streaming on Sonos inside and out. Light shines into the living room with wood-burning fireplace, vaulted ceiling, wall of windows and sliders to a wooden deck overlooking the pool. Dining room with floor-to-ceiling windows and skylights. Two bedrooms and two full baths on the main level; a third bedroom with vaulted ceiling, balcony, and a half bath upstairs. Two-car detached garage with electric charging station; generator. May 15-June 14 @ $15,000, July @ $16,000, August @ $17,000. Less than two hours to NYC but a world away in bucolic Litchfield County.

Sensational country oasis just 90 minutes from NYC is sited on 8.7 picture perfect acres. Boasting a large spring-fed pond with beach (Marilyn Monroe enjoyed many swims in the pond during her residency in Roxbury), expansive patios for entertaining, lush verdant lawns and mature plantings offering complete privacy. This stunning 3 bedroom contemporary was just completely refreshed and is being offered fully furnished as a short term rental. Inside, there is over 4,000 Sq Ft of meticulously maintained living space, an expansive custom kitchen, living room with walls of glass and phenomenal views of the property. Vaulted ceilings throughout and sky lights provide exceptional natural light. The sumptuous primary suite offers ample closet space, and a luxurious bathroom with jetted tub, oversized shower and complete with radiant heat flooring. Two more generously sized bedrooms and bathroom complete the main level. The finished lower level has an office, family room, spa & shower. There is a 2-3 car attached garage parking and an additional detached 3 bay garage barn is an ideal workshop or artist studio. An incredible opportunity for the most discerning seeking privacy and tranquility.

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 or completely closed off on its own with own laundry room. Ideally situated for hiking and birding in the thousands of acres of Roxbury Land Trust & Steep Rock Preserves. Lake activities and near by the Shepaug River, local farmstands, local fairs, antiquing, cultural venues as well as wonderful restaurants and shops. Golf and tennis nearby. This home is close to the charming Town of Roxbury, minutes to Washington Depot and 90 minutes from NYC. RATES FOR LABOR DAY TO MEMORIAL DAY, 2024/25 as follows: 1 BR apt- $2,000/month or whole house-$5,250. SUMMER MONTHS, 2024:1 BR Apt- $2,700 or whole house-$7,850. Plus, utilities & $300 cleaning fee. Inquire for shorter or longer stays. Must See! Main House listed separately as MLS #170623403.

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 new appliances including a wine cooler. Great Room with beams, soaring ceilings, hardwood floors and wood-burning fireplace. Outdoor deck for relaxing and listening to the quiet rush of the stream. Fully-fenced backyard, BBQ Grill, Fire Pit. Central Air. Ideally situated for hiking and birding in the thousands of acres of Roxbury Land Trust & Steep Rock Preserves. Lake activities and near by the Shepaug River, local farmstands, local fairs, antiquing, cultural venues as well as wonderful restaurants and shops. Golf and tennis nearby. This home is close to the charming Town of Roxbury, minutes to Washington Depot and 90 minutes from NYC. NB: This listing is located above a 1 BR apartment, which is currently closed off from the Main House. You have your own private front door entrance, deck and washer and dryer. RATES FOR LABOR DAY-MEMORIAL DAY as follows: Main House- $4,000/mth ADD 1 BR apt- $5,250. SUMMER MONTHS, 2024: MAIN HOUSE -$6,000 ADD 1 BR Apt- $7,850. Plus, utilities & $300 cleaning fee. Inquire for shorter or longer stays. Must See! One bedroom apartment listed separately as MLS #170623688

Available August 1 through Labor Day $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 light and family along with living room and library. Just a short drive to Roxbury Center, and privately sited with a grove of pine trees. Close to Roxbury Land Trust's gorgeous hiking trails, the Shepaug River and Maple Bank Farm, and just minutes away from Washington Depot, New Milford and Woodbury for great shopping and restaurants!

Deluxe SUMMER 2024 furnished rental. AVAILABLE JULY 1-LABOR DAY @70,000 OR MEMORIAL DAY -LABOR DAY @$100,000. 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 full kitchen and its own washer and dryer. Pool, large lawn and ponds. Total privacy.

Enjoy the Academic Year in this delightful 3BDR, 2 Bath Roxbury cottage with pool. Light and bright interior with easy-living, one-level floor plan. Enjoy the morning sunrise and beautiful light throughout the day, and soak in the captivating sunsets from the trellised deck or poolside. In the words of Debussy..."there is nothing more musical than a sunset" and the long western views will not disappoint. Let your eyes wander across the beautifully manicured verdant lawns, providing a sense of both peace and privacy. This property is the perfect escape from city life but also allows one to venture out to local attractions: Refresh at the Roxbury Falls, enjoy local fairs and art shows, hike at Roxbury land trust, or try tennis, horseback riding and golf nearby. Shop at local Farmers markets and farm stands or go antiquing in neighboring Woodbury. Choose from a broad spectrum of dining options from farm to table to Michelin star restaurants. Just 1.5 hours from NYC.

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 House $69,900 OFF-SEASON September - May $12,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $159,000. Please inquire for other/shorter rental terms.

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 Tophet. Inquire for other/shorter rental terms.

Pristine barn-style home on scenic dirt road with barn, stream and small pond. Walk or bike ride along the Shepaug River into a land preserve and historic farms. Magnificent granite fireplace, vaulted beam living room. Dine or relax on the flagstone terrace poolside surrounded by new dawn climbing roses, hedges and blue hydrangea. SUMMER: June - August $30,900/month. Memorial - Labor Day $74,900. OFF-SEASON:September - May $11,900/month If over 3 months, subtract $1,000 per month ANNUAL:$169,000. Ask about other terms.

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 - August $24,900/month; Memorial - Labor Day $59,900 OFF-SEASON September - May $11,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL: $129,000. Ask about other terms. INQUIRE to include Pool House- see separate listing for 253B Tophet.

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. SUMMER June - August $24,900/month; Memorial - Labor Day $59,900; OFF-SEASON September - May $11,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $139,000. Ask about other terms.

Pristine 3-bedroom private mint farmer's home ideal for walking, jogging and biking. Magnificent design with antiques, art and 2 fireplaces, over-sized living room, dining room for 10 and chef's kitchen. Heated pool surrounded by endless summer hydrangea and 11 acres of lawns, pond, and fields. The perfect location minutes from the centers of Roxbury and Washington. SUMMER June - August $26,900/month; Memorial - Labor Day $69,900; OFF-SEASON September - May $12,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $159,000. Inquire about other/shorter rental terms.

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 and spas. Skiing, Lake Waramaug Beaches, BBQ, farm stands and fairs, antiquing, and numerous recreational activities.SUMMER June - August $30,900/month; Memorial - Labor Day $74,900; OFF-SEASON September - May $13,900/month. If over 3 months, deduct $1,000 per month and no tax is due. ANNUAL $169,000. Inquire about other/shorter rental terms.

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.

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.