121 Indian Trail Road
$25,000
New Milford, CT
Rental
Rooms: 11
Bedrooms: 4
Bathrooms: 6
Web ID: 24058089
Memorial Day thru Labor Day 2025 @ $75K. Sophisticated Barn-Style retreat in completely private Merryall location just 10 minutes to the chic shops of New Preston. Renovated to perfection and stylishly decorated. Open floor plan with dramatic floor to ceiling windows. Huge chef's kitchen with pantry, top of the line appliances, wine fridge, 3 ovens, 2 dishwashers, 2 sinks, large center island and breakfast nook. Luxurious master suite with his/hers baths. 5 bedrooms, 5.5 baths. Spacious office/library Media room with uber comfy lounging couches. Deck and screened porch with panoramic views over pond, stone walls and mature trees. Fully irrigated gardens. Gunite Pool is large enough to play or float in and easy to heat as a jacuzzi. Enjoy the immaculate oasis with complete privacy, you will only hear the sounds of nature.
10 Scout Trail
$25,000
Darien, CT
Rental
Rooms: 14
Bedrooms: 6
Bathrooms: 7
Web ID: 24058211
Oasis found at this stunning fully furnished Colonial home perched on top of a hill at the end of a cul-de-sac. This custom 6 bedroom home was built by one of the town's finest builders, Doherty & Deleo. The large eat in gourmet kitchen with an oversized island and butler pantry offers the finest appliances and finishes for you and your guests to enjoy. Relax by the fire in the family room. Retreat to the primary suite with vaulted ceiling, fireplace and walk-in closet. There are 4 additional bedrooms on the second level. Enjoy the professionally landscaped yard complete with a built in fire pit. There is a detached pool house for additional flex space for guests, home office or gym. This house is available from December 15th until March 31st 2025.
939 Black Rock Turnpike
$24,000
Easton, CT
Rental
Rooms: 15
Bedrooms: 5
Bathrooms: 5.5
Web ID: 24061220
This 1700's estate is a perfect summer retreat. It's situated on 3+ acres on the Connecticut Golf Club & serves as a serene and secluded escape from the city. If you are looking for some space to spread out and relax, this 6000+ sq foot home has a little something for everyone. All 5 bedrooms are located upstairs (queen or king beds) with multiple living areas downstairs for reading, working or unwinding. There is an open kitchen & breakfast area for leisurely meals, as well as a large dining room perfect for hosting both casual and formal dinners. It's a beautiful blend of historic character & modern design and there's plenty of room to spread out yet still come together in the shared spaces. Nearby you can find all your favorite New England adventures, including local farms (apple picking, blueberry picking, etc.) and small charming CT towns to...
Mary Kate Klemish-Boehm
(203-221-0666
6 Frisbie Road
$24,000
Washington, CT
Rental
Rooms: 9
Bedrooms: 3
Bathrooms: 4
Web ID: 24061985
AVAILABLE JUNE - AUG 2025 @ $24,000 PER MONTH. Quintessential CT Country Summer rental. Magnificent over-sized pool of 50' x 20' with spa, cabana with a full bathroom, changing room, kitchenette and outdoor grill. Pristine 3 bedroom 3.5 bath main house all bedrooms have king beds. The home is nestled on 21+ acres with new circular driveway, large expanses of lawn, mature trees. Gourmet kitchen, formal dining room, living room with fireplace, large sun room. Covered back porch with comfortable sitting area and outdoor dining. Conveniently located close to town, The Mayflower Inn, tennis courts, fine dining and chic shopping. Many Summer Camps in the area and 1.5 hours to NYC. Also avail $10,000 per month for March- May '25 and Sept 2025-May 2026
26 Pequot Lane
$23,500
New Canaan, CT
Rental
Rooms: 21
Bedrooms: 6
Bathrooms: 8
Web ID: 170493443
THIS MAGNIFICENT ESTATE HAS BEEN FEATURED IN THE N.Y. TIMES MAGAZINE FOR ITS EXTRAORDINARY ENTRY AND CONSTRUCTION. BE IT THE OVERSIZED POOL, ELEVATOR ON ALL 3 FLOORS, SPORTS & TENNIS COURT, MEDIA ROOM, HIS & HER BATHS WITH SEVERAL ADDITIONAL PRACTICAL AND FUN AMENITIES LIKE A CUSTOM BUILT BAR, TWO STEAM SHOWERS, UPSTAIRS AND DOWNSTAIRS LAUNDRY ROOMS, AN EXERCISE ROOM WITH EQUIPMENT, POOL TABLE, SAUNA, WINE ROOM, ETC. ETC. IT CAN BE RENTED PARTIALLY FURNISHED. TV'S, STEREO SYSTEM INSIDE AND OUTSIDE GRACE THIS ONE OF A KIND BEAUTIFUL BRICK HOME WITH PRIVACY ON ALL SIDES BUT CLOSE TO THE MAIN ROAD THIS HOME BOASTS ONE OF THE TOP SCHOOL SYSTEMS AND SPECIAL ED. PROGRAMS IN CT. STONE WALLS & SPECIMEN PLANTINGS ABOUND. NEW CANAAN IS ONE OF THE SAFEST COMMUNITIES IN THE TRI STATE AREA, A MUST CONSIDER IN THESE TIMES. IT IS A MUST SEE. YOU WILL NOT BE...
274 Riverside Avenue
$23,000
Riverside, CT
Rental
Bedrooms: 5
Bathrooms: 5
Web ID: 121568
Nestled in the heart of desirable Riverside this classic colonial has it all. The 5 bedroom, 4 1/2 bath home is set on a flat, private .48 acre lot close to shopping village, train and schools. The main floor has a formal living room with fireplace, dining room, solarium, private office and recently updated kitchen/family room. A first floor bedroom suite completes the ideal floor plan. On the second floor is the primary bedroom suite and 3 additional bedrooms. The third level offers another bedroom and bathroom with a bonus family/playroom. Move in and enjoy all that Riverside has to offer.
71 Wesskum Wood Road
$22,500
Riverside, CT
Rental
Bedrooms: 5
Bathrooms: 5.5
Web ID: 121355
Welcome to 71 Wesskum Wood - Overlooking Binney Park with all its amenities, including sports fields, tennis courts, Summer movie nights and July 4th fireworks! This is also the perfect location for easy access to Old Greenwich Village and train. Dramatic double height family room, dining room, eat in kitchen, and living room and laundry on the first floor, along with the 5th bedroom. The second floor features the primary suite with his and hers closets and 3 further family bedrooms. Large third floor perfect as a kids playroom and / or office area. Large finished lower level with further rec space / gym area / generous storage areas and mudroom connecting to the 2 car garage. Outside fireplace and grill area at the rear of the house is a fantastic entertaining area. Long term (multiple year) option available.
Rob Johnson
(203-869-8100
117 Looking Glass Hill Road
$22,500
Morris, CT
Rental
Rooms: 8
Bedrooms: 3
Bathrooms: 4
Web ID: 24051182
Chic and fabulous, converted antique barn on a quiet and coveted, country road. Light-filled kitchen, spacious and open, dining and living room with wood stove and French doors which opening to the large stone terrace. Private en-suite, primary with balcony, fireplace and dressing room. 2 additional en-suite bedrooms privately situated away from one another. Cozy den with walls of windows, a vaulted ceiling and fireplace. Gorgeous and professionally landscaped private grounds with heated, Gunite pool with wisteria and a clematis laced pergola. Beach rights on Bantam lake. Minutes to Bantam and Litchfield's unique shops and eateries. 10 minutes to the villages of Washington and New Preston & Morris. Quintessential~New England~Country~Property. Available Academic asking $5750/month.
29 Highview Avenue
$22,000
Old Greenwich, CT
Rental
Bedrooms: 5
Bathrooms: 5
Web ID: 121248
A-1 location!! Uniquely private, this South of the OG Village custom-built home is on quiet street close to schools, RR, beach & shops. Sunny 5/6 bedrm home offers multiple play & work spaces. Chef's kitchen w lg stone island, banquette seating & adj family rm w fp opening to expansive patio. Beautifully detailed formal rms plus butler's pantry for entertaining. Convenient mudrm w side entrance. Prim bedroom retreat has 2 lg walk-in closets, luxe bath, fp & balcony overlooking gardens. 3 more bedrms, one w en-suite bath, plus Laundry on 2nd level. Hi ceilings & h'wood floors thruout. Fantastic, walk-out LL w sunlit 5th bedrm, office/6th bedrm, playroom & full bath. Private back yard. Landlord looking for a lease ending no later than May 31, 2025. Also avail for sale.
18 Bear Burrow Road
$22,000
Roxbury, CT
Rental
Rooms: 7
Bedrooms: 4
Bathrooms: 3
Web ID: 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 15th to August 2nd 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.
21 Harkim Road
$21,000
Greenwich, CT
Rental
Bedrooms: 4
Bathrooms: 5
Web ID: 121513
RARE with CONCIERGE SERVICES & UTILITIES INCLUDED Breathtaking 1.5 acre country oasis with heated pool and lush lawns in the exclusive Bailiwick section of Greenwich. Renovated in 2024, this 4 Bedroom, 4.1 Bath, 5300+ square foot home offers the ultimate in privacy while being just minutes to both Greenwich and NY shopping, schools, amenities, and the Bailiwick Club which boasts 7 Har-tru tennis courts. Dramatic double height family room with stone fireplace open to the eat-in-kitchen is the perfect place for both everyday living and formal entertaining. Large windows and glass sliders throughout invite incredible vistas of the beautiful New England seasons to enjoy all year round. Main level primary suite with ample closet storage and built-ins.
37 Attawan Avenue
$20,000
East Lyme, CT
Rental
Rooms: 6
Bedrooms: 4
Bathrooms: 2
Web ID: 24030688
Available Dates are as follows: 7/11 - 7/20, 8/30 - 9/5, 9/15 - 10/18, 10/21 - On. Beautiful Attawan Beach House available for rent. Inquire for all short and long term rentals. This fully furnished home is perfect for a quiet relaxing getaway. A great spot to ride bikes, take walks, relax on the beach and enjoy the wrap around porch all day in the shade. Have a fire at night while grilling in the backyard and hearing the waves. You won't regret your stay. Through labor day - Weekly rentals at $5,950/week + $300 Cleaning fee September & October - weekly rentals @ $3,600/week + $300 cleaning fee Inquire about other dates NIGHTLY RENTALS AVAILABLE with 2 night minimum - INQUIRE Lease and Security Deposit required
3 Nassau Road
$20,000
Westport, CT
Rental
Rooms: 9
Bedrooms: 5
Bathrooms: 5
Web ID: 24060878
This stunning beach Colonial, built in 2022, masterfully blends comfort and style. Tucked away on a cul-de-sac in the picturesque Saugatuck Shores waterfront community, it provides easy access to the lively community life of Saugatuck. The home features a timeless Colonial exterior, complemented by a soothing interior palette of soft whites and sandy tones that echo its coastal setting. Inside, the open first floor features 9-foot ceilings and a bright living room that flows effortlessly into a chef's kitchen and handsome dining room. A first-floor bedroom with an adjoining full bath offers flexibility for guests or a home office. Upstairs, the primary suite is highlighted by a stunning gas-burning fireplace and luxurious spa-like bath. Three additional family bedrooms ensure comfort and privacy, complemented by two well-appointed bathrooms. The third floor provides a versatile retreat that opens to a rooftop deck with breathtaking views of Long Island Sound. Outdoors, the terrace...
29 Soundview Drive
$20,000
Westport, CT
Rental
Rooms: 8
Bedrooms: 4
Bathrooms: 3.5
Web ID: 24038645
Welcome to Compo Beach! Charming furnished rental for the SUMMER MONTHS, JUNE $20,000, JULY $25,000, AUGUST $20,000, SEPTEMBER $17,500. Month to month or short term rental. Very Flexible terms. Beautiful waterviews from almost every room, and your beach is a few steps away. A perfect location with a short walk to Longshore Club with golf and tennis. Have lunch or dinner at Longshore at La Plage Restaurant, and then see a play at the famed Westport Country Playhouse. Enjoy all that Westport has to offer! Flexible dates.
106 Patterson Avenue
$20,000
Greenwich, CT
Rental
Bedrooms: 5
Bathrooms: 4.5
Web ID: 121619
Superbly renovated & totally modernized in 2022, this classic Tudor home is sited on parklike acreage on a premier in-town street only moments to schools, train, town & hospital. Go inside to a new kitchen, restored hardwood floors, new lighting & beautiful arches that create a seamless flow throughout. Upstairs, the primary suite features a newly renovated bathroom & a spacious dressing room. Four additional bedrooms & two updated bathrooms complete the 2nd & 3d floor. The pristine lower level has exterior access, laundry, ample storage, a 1-car attached garage, & a second 2-car detached garage. Outside, the stone terrace is an entertainers delight w/ beautiful views of the lush level lawn, gardens & privacy that are not to be missed.
10 Surf Road
$20,000
Westport, CT
Rental
Rooms: 16
Bedrooms: 4
Bathrooms: 5
Web ID: 24039255
This captivating haven at Saugatuck Shores, nestled along the pristine shores of Bermuda Lagoon, 100 feet of private beach and a deepwater dock-your perfect launchpad for unforgettable summer adventures or a warm winter escape. With soaring ceilings framing breathtaking water views, this open and airy oasis is ideal for year-round relaxation. Enjoy sunsets on the expansive wrap-around deck or cozy up inside by the fire as snow falls. Indulge your inner chef in the gourmet kitchen, featuring an industrial stove, then gather around the marble table for meals with stunning views as your backdrop. The master suite is a true retreat with its own waterside deck, walk-in closets, and a luxurious bath complete with a Jacuzzi tub, shower, and double vanity. The main level includes three additional bedrooms, two with charming lofts perfect for younger guests. On chillier days, head to the lower level family room with a...
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