Roxbury CT Real Estate & Homes for Rent

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. Upstairs you're greeted by soaring ceilings and quality finishes that further establish the home's distinctive character. The great room features a fireplace, tv, dining for 8-10, gourmet kitchen and windows that frame pastoral views of the Litchfield Hills. The Great Room walks out to a covered porch with lounging, dining table and bbq. The primary bedroom with its luxurious 4 piece bath and an additional bedroom/bath complete this level. Brand new designer furnishings create sophisticated living spaces throughout. There is also an electric car charger. 10-12 minutes to the charming village centers of Washington and Woodbury which offer fine dining, organic markets, farmer's markets and many cultural attractions. This extraordinary rental represents Connecticut country living at its most refined.

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 reach in closet with upper storage. Sliding doors off the main living area open to a private back deck, providing a wonderful spot to unwind. Beautiful touches abound, from gleaming hardwood floors to a sparkling new bathroom. Both the bedrooms feature double closets for ample storage. Modern comforts include new mini-splits for heating and cooling, adding to the cabin's appeal. For an added fee, there is a two-car garage houses the laundry area and an additional heater. Plus, you're just a short stroll away from a lovely riverside picnic spot and the popular Roxbury Kitchen for a delicious meal. This cabin is perfect for those seeking comfort and convenience in a picturesque setting!

Summer 2025 at $16,000 per month. 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 wood-burning fireplace, Formal Dining Room and a Wonderful Terrace overlooking the verdant open lawn replete with a picturesque pond, towering pines and mature trees, plantings and perennial gardens. Play tennis at the adjacent Roxbury Town courts, meander across the street for Ferris Acres Ice Cream and other delectables at the Roxbury Market or visit near-by Maple Bank Farm, Land Trusts with trails, river access and waterfalls or drive a short distance to many world-class restaurants. Two-car attached garage and bicycles available. Barn not included in rental.1.5 hours to NYC. Special. Inquire regarding longer rental term.

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 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!

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 with Separate Pool House. Comfortably Furnished and Well Appointed.

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 deck, flooding the space with natural light and providing a wonderful spot to unwind. Elegant touches abound, from gleaming hardwood floors to a sparkling new bathroom. Both the bedroom and living area feature double closets for ample storage. Modern comforts include new mini-splits for heating and cooling, adding to the cabin's appeal. A two-car garage houses the laundry area and an additional heater. Plus, you're just a short stroll away from a lovely riverside picnic spot and the popular Roxbury Kitchen for a delicious meal. This cabin is perfect for those seeking comfort and convenience in a picturesque setting!

January 2025 - June 2025: $4,500 per month plus utilities. 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. Ideally situated for hiking and birding in the thousands of acres of Roxbury Land Trust & Steep Rock Preserves. Lake activities and nearby 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. (The listing is located above a lower level 1 bedroom apartment, which is closed off from upstairs). You have your own, private, front door entrance and deck and exclusive access to washer and dryer. Add lower-level (making it whole) house: $5,500 (4 bed/3 bath). Summer 2025: Main House, $6,000 plus utilities/month. Add Lower Level 1-Bedroom Apt. (Full House) $7,850/ month. $300 for cleaning. Inquire for shorter terms. See 10B Sentry Hill for Lower Level 1-bedroom rates

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 full kitchen and its own washer and dryer. Pool, large lawn and ponds. Total privacy.

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 in the rent, making it even more appealing. Plus, you're just a short stroll away from a lovely riverside picnic spot and the beloved Roxbury Kitchen for a bite to eat. Perfect for those seeking comfort and convenience!

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.

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 minutes from NYC. Also available June for $14,000 and July for $22,000 per month (MLS #24010919).

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 for $14,000 or July or August for $22,000 per month. Just 90 minutes from NYC. Also available from short term between Labor Day and Memorial Day for $7,500 per month. Contact agent for availability.

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.

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.

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.