Featured Properties

Some or all of the listings below are provided by the Westport office.
$20,000 / mo
Active

Saugatuck Shore Area Rental Home

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10 Surf Road Westport, CT 06880

4 Bed
5 Baths
5885 sqft
MLS# 24092268
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 cozy fireplace, or enjoy the 85-degree indoor 42ft pool, sauna, steam room, and gym-perfect for wellness and relaxation. Step outside to your private beach, where you can watch buffleheads dive, or swans and herons glide through the wetlands, a tranquil sight during snowy winter days. Fully furnished and ready for you to customize, this waterfront gem offers the ultimate balance of nature, wellness, and beauty, whether it's summer or winter in Connecticut.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Inna Agujen
$18,500 / mo
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Coleytown Area Rental Home

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28 Clinton Avenue Westport, CT 06880

5 Bed
4 Baths
2899 sqft
MLS# 24105039
Exceptional, remodeled home with a beautiful pool near downtown Westport. The "Everett Fillow House, c 1911" was completely restored & exquisitely updated by the present owner to the highest standards of excellence. The welcoming curb appeal & charming front porch create a gracious approach to this Colonial Farmhouse. Step inside and experience the bright open flow, characterized by high ceilings, large windows, & intuitive custom features for a comfortable lifestyle. The Great Room includes a fireplace in a bay of windows, & opens to a serving bar/butler's pantry space w/ice machine, 2 refrigerator drawers & excellent storage. The gourmet kitchen is a chef's delight, w/extensive cabinetry, gas cooktop & top appliances, a glorious view out to the pool & herringbone-patterned backsplash to the ceiling that adds a stunning accent. The dining area has a built-in marble-topped serving cabinet, & French doors to the deck. Main level mudroom/laundry leads to the attached 2-car garage & out to the backyard. The second level includes a flexible layout w/spacious bedrooms. The main BR suite is an exquisite retreat w/fireplace & bay window, complemented by a stunning primary bath w/marble, glass shower & custom vanity. The finished third floor is a great bonus space, lined w/windows & filled w/light - it includes a clever hidden daybed for extra guests & a refreshment center. The magnificent backyard has a stunning pool with patios, a firepit & level lawns. Full-house Generator.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Barbara Bross
$18,000 / mo
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Compo Beach Area Rental Home

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19 Bluewater Hill Westport, CT 06880

3 Bed
3 Baths
3066 sqft
MLS# 24088536
Furnished Yearly Rental with dramatic views of the Long Island Sound and pool at one of the areas premier addresses- Steps To Compo Beach and Longshore Country Club. Located on prestigious Bluewater Hill, this home is part of association with deeded Beach rights and Tennis courts. This home offers 4 bedrooms, 3 full baths, flexible floor plan with great entertaining areas, outdoor patios and property. Available 9/1/25. Shorter Term Rental option possible @15,000/mo
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Douglas "Doug" Bross
$15,000 / mo
Active

Compo Beach Area Rental Home

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19 Bluewater Hill Westport, CT 06880

3 Bed
3 Baths
3066 sqft
MLS# 24088530
Furnished Short Term Rental with dramatic views of the Long Island Sound and pool at one of the areas premier addresses- Steps To Compo Beach and Longshore Country Club. Located on prestigious Bluewater Hill, this home is part of association with deeded Beach rights and Tennis courts. This home offers 4 bedrooms, 3 full baths, flexible floor plan with great entertaining areas, outdoor patios and property. Available after 9/1/25
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Douglas "Doug" Bross
$11,900 / mo
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Lower Weston Area Rental Home

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38 Davis Hill Road Weston, CT 06883

6 Bed
5 Baths
4085 sqft
MLS# 24122336
Welcome to 38 Davis Hill Road, Weston - a beautifully appointed Colonial residence set on just over 2 private acres with meticulously landscaped gardens, mature plantings, and multiple patios. Designed for both relaxation and entertaining, the grounds feature a heated Gunite pool with attached spa, a pool house, and exceptional outdoor living spaces. Inside, enjoy more than 4,500 sq. ft. of elegantly furnished living space, including 6 bedrooms and 5 bathrooms. A chef's kitchen anchors the bright, flexible floor plan, while spacious living areas offer comfort and versatility. A secure vegetable garden provides abundant seasonal produce, enhancing the home's appeal for those who value fresh living. Located less than 10 minutes from downtown Westport, this residence combines privacy and convenience. Available furnished for short- or long-term rental-just bring your suitcases and move right in. Inquire with listing agent regarding short-term renatl pricing.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Benjamin "Ben" Howell
$10,500 / mo
Active

Compo Beach Area Rental Home

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112 Hillspoint Road Westport, CT 06880

4 Bed
4 Baths
3558 sqft
MLS# 24114052
This delightful, sun-filled home, nestled on beautiful park-like grounds, offers the perfect blend of modern amenities and timeless charm. The inviting family room, framed by multiple French doors, opens to an expansive bluestone patio overlooking the private backyard an ideal setting for effortless indoor-outdoor living. The spacious dining room, featuring its own French door to a secluded patio, flows seamlessly into the chef's kitchen, complete with a breakfast bar and high-end appliances, making entertaining both elegant and easy. A study/library, mudroom, and gracious foyer complete the first floor. Upstairs, the generous primary suite boasts a walk-in closet and full bath, while three additional bedrooms, two full baths, and a convenient laundry room provide ample space for family and guests. The finished lower level offers a versatile playroom or recreation space, complemented by a detached two-car garage. Ideally located just minutes from downtown Westport, Compo Beach, Longshore, Saugatuck Center, and the train. 112 Hillspoint Road is your chance to rent a little slice of paradise and experience all that Westport has to offer.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Barbara Sweeney
$9,500 / mo
Active

Coleytown Area Rental Home

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9 Grays Farm Road Westport, CT 06880

4 Bed
2 Baths
2284 sqft
MLS# 24126753
Flexible Long-term FURNISHED rental: $9500 yearly or $10500 short term FURNISHED. ALSO AVAILABLE UNFURNISHED SEE MLS#24126749. Fully remodeled, turn-key home on a premier estate property at the end of a cul-de-sac. Modern styling blends with a captivating private setting to create a unique oasis. Two acres of park-like property, abutting the Paul Newman-Poses Preserve, offer rare serenity in a convenient location. A respected local builder transformed this home into a Transitional-Style Farmhouse, combining high-end new-construction features with ideal scale and price point. Enter the glass front door to an airy, open main level. Living area with fireplace flows to dining and upgraded kitchen. Step onto the expansive deck with lovely views of the flat backyard and unmatched privacy. Recreation room works as family room, game space, or home office. Upstairs, bedrooms are sleek with ample closets and chic, European-style baths. Lower level offers storage or gym/bonus space. Attached two-car garage. Renovated in 2022; built in 1964.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Douglas "Doug" Bross
$8,750 / mo
Active

Coleytown Area Rental Home

Active

9 Grays Farm Road Westport, CT 06880

4 Bed
2 Baths
2284 sqft
MLS# 24126749
Flexible short-term UNFURNISHED rental: $8,750 yearly or $9,500 short-term. ALSO AVAILABLE FURNISHED SEE MLS# 24126753. Fully remodeled, turn-key home on a premier estate property at the end of a cul-de-sac. Modern styling blends with a captivating private setting to create a unique oasis. Two acres of park-like property, abutting the Paul Newman-Poses Preserve, offer rare serenity in a convenient location. A respected local builder transformed this home into a Transitional-Style Farmhouse, combining high-end new-construction features with ideal scale and price point. Enter the glass front door to an airy, open main level. Living area with fireplace flows to dining and upgraded kitchen. Step onto the expansive deck with lovely views of the flat backyard and unmatched privacy. Recreation room works as family room, game space, or home office. Upstairs, bedrooms are sleek with ample closets and chic, European-style baths. Lower level offers storage or gym/bonus space. Attached two-car garage. Renovated in 2022; built in 1964.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Douglas "Doug" Bross
$7,900 / mo
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Old Hill Area Rental Home

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259 Wilton Road Westport, CT 06880

5 Bed
5 Baths
2186 sqft
MLS# 24116277
Discover a spacious and flexible Westport ranch on nearly 2 private acres. The home features 5 bedrooms and 4 full baths. The main level includes 4 bedrooms, 3 baths, and an updated kitchen. The finished walkout lower level adds about 1,000 square feet and includes a separate apartment with a full kitchen, a bathroom, its own laundry, and a private entrance. There are three laundry areas in total. Recent improvements include updated kitchen and baths, a new HVAC system in 2023, and a whole house generator in 2022. The entire home has been freshly painted inside and out. Outdoor living shines with a large patio, oversized deck, retractable awnings, and bonus outdoor powder room perfect for entertaining, this thoughtfully placed exterior powder room sits just beneath the deck with direct access from the patio. No need for guests to walk through the house ideal for backyard gatherings, or casual evenings on the terrace. A true convenience that keeps the party flowing outside. Prime location. Walk to the Y for activities. Move right in and make it yours.
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Inna Agujen
$7,500 / mo
Active

Compo Beach Area Rental Home

Active

45 Drumlin Road Westport, CT 06880

3 Bed
2 Baths
1348 sqft
MLS# 24124785
Yearly unfurnished rental in a "walk to Compo Beach" neighborhood. This fully renovated home lives big with 3 bedrooms plus 2 full baths, a family room with fireplace, and an office/den w French doors to a private patio. The dining room, with built -in glass hutch, is large for entertaining or every day dining -right off the kitchen. The kitchen has granite surfaces and handsome stainless steel appliances with a gas range, plus a laundry room with LG washer/dryers located off the kitchen. The private backyard is fenced on three sides, has mature trees and shrubs and a large usable shed- a lovely place to soak in the sun and BBQ. Hardwood Floors through-out. A well-cared for home - The location cannot be beat-minutes to the Westport Train Station. Move right in and enjoy all that Westport has to offer. Available immediately!
Listing Courtesy of SMART MLS / Coldwell Banker Realty / Sally Bohling

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