10 Lone Pine Lane
$24,000
Westport, CT
Rental
Rooms: 10
Bedrooms: 4
Bathrooms: 3.5
Web ID: 24077811
SUMMER RENTAL: AVAILABLE JULY ONLY. Enjoy all that Westport provides this summer in this perfect FURNISHED 4-5BR home in one of Westport's most sought-after neighborhoods. This beautiful home is set back on the property with a babbling brook. An inviting front porch will have you sipping iced tea all summer long, watching the idyllic and vibrant neighborhood life go by. A short walk to downtown, with wonderful shops, restaurants, parks and amenities. And bike or a short drive to the beach! The sun-filled first floor has an open layout w/ an impeccably furnished living room w/fireplace, frame tv, large dining area. The chef kitchen with Wolfe, Bosche & Sub-zero appliances has a large island, butler pantry w/wine cooler making this home perfect for entertaining! A bright sunroom w/ entertainment center leads to a secluded fully fenced backyard complete with hot tub, fire-pit, grill, outdoor dining area, and outdoor shower. The...
Kathleen Lawton Gibbon
(203-221-0666
Mark Gilrain
(203-221-0666
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.
11 Roosevelt Avenue
$23,000
Old Greenwich, CT
Rental
Bedrooms: 5
Bathrooms: 2.5
Web ID: 122135
Enjoy a long summer holiday in the perfect rental south of the village in Old Greenwich. It is available for 4 months. Spend time with coffee (or cocktails) on the front porch or private back patio overlooking the back garden. The gourmet kitchen with island, sitting area with stone fireplace and eating area make up the heart of the home. Primary bedroom and luxurious bath as well as 4 bedrooms are on the second fl. Separate studio/office offers a peaceful area to work or relax. All this plus a private outdoor shower to wash away all of your summer activities! Short distance to OG village, beach and train.
Joann P. Erb
(203-869-8100
Railtree Hill Road
$22,500
Woodbury, CT
Rental
Rooms: 11
Bedrooms: 5
Bathrooms: 4
Web ID: 24071315
AVAILABLE AUG - LABOR DAY 2025 @$22,500. Chic, well appointed Colonial with heated Gunite pool on a quiet road close to Woodbury's shopping and dining. Perfect for entertaining, this gracious home is set up with 5 bedrooms. The main floor has a large living room with fireplace, formal dining room and a bright, modern kitchen. The sunroom is a favorite spot to chill, with direct access to the spacious back deck and hot tub. There is a first flr bedroom and bonus room that will be a gym space. The second flr has the primary bedroom with en suite bathroom, walk in closet and private office. There is another large guest room with en suite bath on second floor with 2 queen sized beds and a couch that pulls out into a full sized bed. The 3rd flr has two more bedrooms, one with 2 queen sized beds and the...
Old Norwalk Road
$22,500
New Canaan, CT
Rental
Rooms: 11
Bedrooms: 5
Bathrooms: 4
Web ID: 24065193
Welcome home! This impeccably renovated New Canaan estate embellishes the modern luxury of today's standards while grasping the classic elegance and architecture of the period in which this home was built. The gorgeous grounds features professionally manicured landscaped with an abundance of stonework and gracious iron fencing. Luxury amenities include a custom heated pool , built in outdoor kitchen, bluestone terrace, two porches one covered the other one is screened in to complete the multitude outdoor living spaces. Enter into the home through this inviting foyer that will certainly make an impression to your most discerning guests. Impressive design and architectural details are embellished through out this home. This 5 bedroom home offers over 4100 square feet of living space on the first and second floor. The primary suite boasts an expansive foot print which includes vaulted ceilings, walls of windows, floor to ceiling paneling and a large sitting room...
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.
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
W Shore Avenue
$22,000
Groton, CT
Rental
Rooms: 5
Bedrooms: 3
Bathrooms: 3
Web ID: 24077648
Waterfront Furnished Rental - 3BR/2.5BA - Steps to Beach! Escape to this stunning 3-bedroom, 2.5-bathroom furnished waterfront home with breathtaking views! This beautifully appointed rental features central air, an open-concept living space, and large windows that flood the home with natural light. Enjoy direct access to the beach, boating, and tennis courts just steps from your door. Whether you're relaxing on the deck, taking in the serene waterfront scenery, or entertaining this home offers the perfect Groton Long Point coastal retreat. Available for the month of July or 7/1-15, 7/16-31. Don't miss out on this prime location-schedule a showing today!
Kelsey Place
$22,000
Madison, CT
Rental
Rooms: 9
Bedrooms: 5
Bathrooms: 3
Web ID: 24070967
A TRUE MADISON WATERFRONT (No street or HOA in front) FOR MONTH OF AUGUST With incredible views out over Long Island Sound & beyond this light & bright Beach Colonial was newly built in 2006 plus has a recent 3 BR room addition & renovated Baths! Featuring an open floor plan, all in excellent condition with lots of glass & a wrap around deck to take full advantage of it's setting. Located at the very end of a private street this special home is in a nice quiet setting. Hardwood floors both up & down, central vac, a first floor den with sleeper couch that is perfect for those unexpected guests with a full bath right around the corner, newer propane heat and fully air conditioned. Set up high on piers, you'll feel like you are on a boat! Enjoy awesome sunrises AND sunsets from a single location! Labor Day...
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.
Water Street
$20,000
Stonington, CT
Rental
Rooms: 7
Bedrooms: 3
Bathrooms: 4
Web ID: 24069040
AVAILABLE August, 2025. Stunning 3BR/ 3.5 bath remodeled home with water views and just steps from the beach, boasts a newer kitchen with huge center island and high end appliances. Open kitchen/dining allows everyone to congregate without getting in the way. The living room has a wood burning fireplace and water views through the covered front porch. In the back is an off-street parking spot and a private patio for al fresco dining. Workmanship and finishes make you think you are staying in a 5 star hotel. The third floor has office space and an open area and a full bath. Located just 1 block from the beach and Stonington Point, you are never far from the fine shops and restaurants in the Borough. August 2025 @ $20,000/mo. Tenant responsible for $3,000 security deposit & $350 non-refundable cleaning.
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...
Strawberry Ridge
$20,000
Warren, CT
Rental
Rooms: 8
Bedrooms: 5
Bathrooms: 3
Web ID: 24077037
Academic or winter rental. Strawberry Ridge Chalet is nestled between pristine vineyards overlooking Lake Waramaug. Complete privacy down a long driveway past the pond is a 5 bedroom home. Top of the line eat-in kitchen with seating area and stone fireplace. Flooded with light the living room/dining has vaulted beamed ceilings, sliders out to the orchard, vineyard and stream. Office/5th bedroom and full bath on the 1st floor. The upstairs features the primary suite and 3 additional bedrooms and 2 bathrooms. Two rooms double as an in-law/guest apartment with a kitchenette and separate entrance. Pool, new hot tub and sauna room. Abundant patio and outdoor space are perfect for entertaining overlooking the vineyard. A perfect rental year-round or summer. Lake Waramaug with beach pass is just at the bottom of the hill and a quick trip to the villages of New Preston, Washington and Litchfield.
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, AUGUST $20,000, SEPTEMBER $17,500. AND WINTER MONTHS 2025: FEBRUARY $15,000, MARCH $15,000, APRIL $15,000. 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 and 3 pools (with Parks and Rec permit). 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. JULY 2025 HAS BEEN RENTED.
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