Westport CT Real Estate & Homes for Rent

Beautiful home in lovely New England town at Coveted Stony Point location. Walk to beach, train, shops, restaurants, Longshore, pool, tennis, golf. Beautifully maintained home inside and outside. Open Floor plan with gorgeous hardwood floors. Kitchen has Viking appliances, wine chiller, and subzero refrigerator, laundry room. Six bedrooms and four baths. Two primary bedrooms one on Main Level and one on upper level. Second Floor has open office, playroom, in addition to three Bedrooms and two baths. Partially fenced in yard, beautifully manicured gardens, eye catching backyard bordered by stonewall and large green giants along with stunning wood patio and Neapolitan outdoor pizza oven. Green Giants line the front yard with a long winding driveway with large metal gate. New beautifully designed large storage building. New Roof. Sprinkler system keeps greenery in top condition. Don't lose out on the opportunity to have Westport home.

TOO GOOD TO BE TRUE! Once you turn the bend on Harbor Road it is like a retreat in the fabulous town of Westport! This gorgeous 3 bedroom, 2.1 bath with a sleeping loft is relaxing in a gorgeous beach community. If you always wanted to try beach living this is the place for you. The entire house is sun-drenched and has water views from almost every room! This home also boasts a stone patio and outdoor fireplace for family and friends to gather. Saugatuck Shores beach community is a fun and friendly neighborhood. -- The property is close to Saugatuck Rowing Club which has a beautiful fitness facility and restaurant. It is super easy to commute from the train station away from the traffic. Close proximity to other fabulous restaurants like Tarantino's, Gabriele's and The Whelk to name a few. Best of all is this home has front row seating on an amazing deck overlooking the water to the 4th of July fireworks celebration. - Imagine waking up to a full view of the sunrise every morning! Come and take a walk along the sound with a beautiful view of the lighthouse and relax and the beach. A moment of zen in the heart of Westport Connecticut!

A rare rental opportunity in one of Westport's most sought-after neighborhoods-this exceptional stone & shingle home is set on a manicured, level acre on a premier cul-de-sac. Offering nearly 9,000 square feet of refined living, this residence combines classic architectural detail with contemporary comfort, showcasing 9'-10' ceilings, custom millwork, and five fireplaces. The gourmet kitchen opens to an inviting great room with stone fireplace and French doors to the patio. Formal living and dining rooms, plus a handsome wood-paneled library, create a gracious main level. Upstairs, five well-proportioned bedrooms include a stunning primary suite with 12' ceilings, fireplace, and spa bath with double steam shower. A spacious bonus room offers flexible living space and includes a potential in-law or au pair suite with its own bedroom and full bath. The walk-out lower level includes a media room, gym, rec/play room, second family room, and full bath. Outside, enjoy a secluded retreat with 20x50 heated Gunite pool/spa, stone patio with fireplace, and lush landscaping. Walk to Long Lots Elementary, Bedford Middle & Staples HS. Truly an exceptional offering!

Great opportunity to call Westport home. 4 Bedrooms and three and a half bathrooms colonial. Walking distance to Compo Beach, Longshore, golf, tennis & Sailing, great restaurants, downtown Westport and the train. Access to mid-town Manhattan in just over an hour. 4500 s/f feet that with large kitchen that opens to family room. Spacious Bedrooms and Baths. Wonderfully finished basement for office, gym and/or playroom. Convenient Laundry room. A 2 car garage surrounded by eye catching backyard, landscaping & patio. Live in one of the most beautiful New England towns with top schools.

Compo Beach living! 2 short blocks from beach on private road! Brand new home! 5 bed, 4.5 bath modern home w/ all of the lush amenities seen in the finest resorts both inside & out. Custom Italian cabinetry in kitchen, butler's pantry, bathrooms, and mudroom. 9ft.+ ceilings, open stairs w/ glass railings & oak floors. Entry hall w/ crystal chandelier spiraling down from open ceiling. Formal dining room w/ custom millwork, butler's pantry w/ 2nd dishwasher, sink, beverage cooler & spacious pantry closet. Custom-designed gourmet kitchen w/ 6 burner gas range, wall oven, drawer microwave, sink disposal & quartz countertops. Sunny rear dining area w/delicate decorative painted millwork. French doors to spacious covered main level deck overlooking in-ground pool & flat landscaped yard. Open family room w/ 75" TV & linear gas FP. Guest suite w/ WIC. Spacious home office. 2nd fl. w/ vaulted ceilings, loft, laundry room, 1 bedroom suite, 2 bedrooms share J&J bath, all w/ walk-in closets. Primary bedroom suite w/ gas FP & private rear balcony w/ water views. 2 walk-in closets furnished w/custom Italian cabinetry. Spa bathroom w/ heated floor, 2 sinks vanities, oversized walk-in shower, deep soak tub, towel warmer, linen & water closets. Roof deck w/ gas FP and views of LI Sound. Spacious landscaped yard & gardens,ground-level covered patio perfect for entertaining w/ gas FP, ceiling fans & lighting. Exterior storage room. inground pool with autocover. Min 6 month rental

HIGH END LIVING~ This home is located in the "Golden Triangle" of downtown Westport. Bedford Square is a unique multi-purpose destination that includes premier residences, beautiful public areas, high-end retail and dining. Bedford Square is the culmination of the renovation and restoration of the stately 1923 Bedford Mansion and historic Firehouse. Bedford Square is ideally situated in the heart of this vibrant and prosperous community at the foot of Main Street and Church Lane. This luxury two-bedroom apartment is in the main building/pavilion. All feature upscale amenities and amazing views. Whether you are looking for an alternative to New York City living or want to downsize, Bedford Square offers a lifestyle of convenience to its residents. We can arrange rental lengths of yearly, two years or more.

A CERTIFIED PASSIVE HOME. This modernist concrete home, designed by Francis Barry Byrne, a protege of Frank Lloyd Wright, offers a unique blend of luxury and sustainability. Perched atop a hill, it provides breathtaking views of century-old Rhododendrons and oak trees. The property includes a pool, spa, casita, and cottage, surrounded by indigenous plants. Conveniently located between I-95 and the Merritt Parkway, the home features high-performance German windows and doors and energy-efficient systems for a healthy living environment. Eco-friendly elements include electric car chargers and a virtually chemical-free pool. The primary suite offers a private patio, enhancing the serene and luxurious experience. This home seamlessly integrates modern design with environmental consciousness for an exquisite retreat.

Updated 2 bedroom in the heart of Saugatuck! - Updated kitchen, quartz counters, and stainless steel appliances - Updated bathroom - Lots of natural light in this second floor unit! - French doors in kitchen and living room with private balcony off of living room! - Patio area in back for seating and a grill - Amazing location... Walk to multiple restaurants in Saugatuck, shopping, Metro North train, and more! - Washer / dryer in unit - Off/street parking - Landlord to consider one cat or small dog (20 lbs. or less) on a case-by-case basis with $50 / month pet fee

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.

Pristine 1918 Cottage in the Old Hill area of Westport. Recently restored with thoughtfulness and care, keeping the integrity and character alive! Beautiful hardwood floors, cozy renovated kitchen with eating nook, living room and dining areas, family room with sliders to patio and backyard , 3 bedrooms , 2 full baths. Set back off Woodside w/ private yard. Just minutes to town, train and beach!

Welcome to 108 Harbor Road, a beautifully updated 4-bedroom, 2.5-bath home on desirable Saugatuck Island in Westport. Enjoy an open floor plan, recently renovated, and stylish finishes in every room. Just a short stroll to the water, this inviting home offers the best of coastal living and easy access to all that Westport has to offer. Available for up to 9 months starting September 15.

Charming 3-4 Bedroom Colonial in Prime Westport Location - Available August 1 Bright and updated Colonial in a quiet, walkable neighborhood close to shops, restaurants, schools, and commuting options. This 3-4 bedroom, 2.5 bath home features a welcoming front porch, spacious living and dining areas, and an eat-in kitchen with new appliances-brand new range and dishwasher on order. The flexible floor plan includes two bonus rooms on the main level, ideal for a home office, den, or guest space. Upstairs offers three generously sized bedrooms and two full baths, including a primary suite with a large walk-in closet. Upstairs laundry with brand new washer/dryer. Enjoy a private yard and deck, perfect for outdoor living.

Nestled in the serene and picturesque area of Westport, Connecticut, 34 Sasco Creek Road offers a perfect blend of elegance and comfort. This charming residence is set on a generous 2.02-acre lot, embodying the essence of tranquil living, with the added convenience of being just a short stroll from Southport Beach and the Audubon Sanctuary. The home boasts three bedrooms and two and a half beautifully updated bathrooms. Enjoy the glass-enclosed sunroom, complete with French doors leading to a delightful patio overlooking a meticulously manicured, expansive fenced yard. This property provides an ideal retreat for year-round enjoyment with family and friends.

Stunning 4-Bedroom Historic Gem in the Heart of Downtown Westport Step into a rare piece of Westport history with this beautifully restored and fully renovated apartment, perched on the 3rd floor of a charming 1892 walk-up commercial building. This expansive 4-bedroom, 2-bath residence seamlessly blends timeless character with modern updates, offering a truly unique and inviting layout. With generous proportions throughout, this home features plush carpeting in the living areas and bedrooms, and sleek finishes in the kitchen and bathrooms. The open floor plan provides excellent flow for entertaining or simply enjoying the spaciousness of this one-of-a-kind property. You'll love the unbeatable location - just steps from vibrant downtown Westport and moments from the Levitt Pavilion, where music and community events are always on the calendar. This is a rare opportunity to live in a distinctive, historic space that's move-in ready and available for immediate occupancy. Don't miss your chance to experience this special property - schedule your showing today!

BRAND NEW ROOF. BRAND NEW BOILER. NEW CENTRAL AC (coming soon). Even though the house is not new, it sure will seem like it is! But that isn't the best part about this house...this lovely home is in a catbird seat location! Walking distance to the best Westport has to offer...Main Street shops & restaurants, the library, the Levitt Pavilion, the farmers' market or the Playhouse. A quick bike ride to Longshore Park or Compo beach, this home sits in the heart of Westport. Newly painted and refreshed, this home is so easy to enjoy. A lovely, sunlit living room with a wood-burning fireplace is wonderful for entertaining. A roomy, eat-in kitchen is adjacent to the dining room with sliding doors that leads out to a deck. Having dinner on the deck is like dining among the treetops! Two ample-sized bedrooms and a hall bath, along with the Primary bedroom with ensuite bath, complete the upper floor of this home. The downstairs has an office or workout space (you decide how to use it!) and a large family room with a fireplace and sliders that lead out to the newly landscaped backyard. To complete the package, this house has a very convenient attached two-car garage. The only thing better than the location, is the wonderful home itself!

This light filled home is set on 2 acres finished on both levels with over 2300 sq ft of living space. Beautiful flat back yard for fun summer games. Just 3 minutes from the Metro North, and convenient to all the Westport amenities.

Just a 3-minute walk to Compo Beach waterfront! Short-term unfurnished rental (6 month min term), in the center of Compo Beach. Ideal location! 4 bedroom with office, 3 full, 1 half bath. Eat-in kitchen, family room with large deck, finished basement with door to back yard, private laundry room. Lots of space in this 3,129sf home. All bedrooms with new window AC units. BBQ on the deck, play in the yard, walk to the beach. Enjoy the summer and fall at Compo Beach! Pet friendly. Avail starting 7/8

This beautifully maintained Westport 1-bedroom apartment provides the perfect blend of convenience and charm. Ideally situated within walking distance of trains, buses, restaurants, bars, and coffee shops, it's also just a short drive to Compo Beach, Longshore, and Main Street. Flooded with natural light, this bright and airy second-floor unit features gleaming hardwood floors and an updated kitchen equipped with a refrigerator, electric range, dishwasher, microwave, and sink. River views and landscaped grounds make this location perfect. The landlord provides heat, hot water, snow removal, and trash collection. Tenants are responsible for electricity and cable/internet. Additional perks include one assigned parking space and access to a coin-operated laundry in the basement. Must have excellent credit, strong references, and proof of income. No pets, smoking, or vaping allowed. Don't miss this fantastic opportunity to live in the heart of Westport!

Charming Summer Retreat in the Heart of Westport! Blend timeless New England charm with today's modern comforts in this beautifully appointed 5-bedroom, 4.5-bath home, perfectly located on a quiet cul-de-sac just steps from Winslow Park, The Westport Country Playhouse, and downtown. This spacious home sleeps 10 comfortably and is finished on three levels, offering plenty of room for family and guests. The main level features elegant living spaces filled with natural light, while the lower level includes a casual hangout area, a second kitchen, a bedroom, and a full bath - ideal for entertaining or providing extra privacy for guests. Outside, enjoy a beautiful back deck and a lush yard perfect for summer barbecues or relaxing with a book. Bike to Compo Beach, stroll into town for evening dinners, or spend the day at nearby Longshore - all just minutes away, including the train for easy NYC access. Rental dates are flexible during the summer months. This is your perfect summer escape in Westport - luxurious, private and convenient!

Lovely sunny cottage with recent updates--separate and private, attached to main house, on a beautiful cul de sac in the heart of Westport. Private entry and large entry foyer suitable for study/office, large eat-in kitchen with stone countertops, stainless steel appliances, stairs to living room and separate bedroom with ample closet space, new bath and washer/dryer. Private garage, 1 spot only, guest parking is on street. Tenant pays credit check. Utilities are paid as additional flat fee of $150/month. Please note: This is a single occupancy unit.

Available for the academic season, this spacious and elegant home in the desirable Saugatuck school system offers the perfect combination of comfort and convenience for your stay. Step into a stunning high ceiling foyer that sets the tone for this beautifully maintained home, featuring hard wood floors and natural light. With 4 spacious bedrooms, and 3.5 bathrooms, there is plenty of room for family and guests. The heart of the home is a gourmet eat-in kitchen, thoughtfully designed for both cooking and entertaining, with premium appliances and ample space. The finished walk out lower level adds even more living and recreational space, ideal for a playroom, a gym or home office. With approximately 3,900 square feet of living space, this home offers a prime Westport lifestyle for the academic year.

Back on the Market - Freshly Updated and Ready for You! Available August 1st, this beautifully maintained 4-bedroom, 2-bathroom ranch offers flexible one-level living in a prime Westport location. With brand new carpeting in the bedrooms, a brand new washer and dryer, and a newly finished sunroom perfect for a home office, gym, or playroom, this rental checks every box. Located on a private street in a quiet neighborhood, this home also offers ample off-street parking and outdoor space ideal for entertaining-just in time for summer! The versatile layout provides options for a fourth bedroom, guest suite, or work-from-home setup. Enjoy the convenience of being within walking distance to Compo Beach and just minutes from downtown Westport and the train. A large attic and shed provide excellent storage, and all appliances have been updated. Don't miss this fantastic opportunity to rent a move-in ready home in one of Westport's most desirable areas. Available August 1st. Security deposit and credit check required.

Nestled on the coveted Turkey Hill Road S. in the heart of Greens Farms, this impeccably maintained 5BR Colonial offers the perfect blend of classic elegance and modern comfort. Set on professionally landscaped grounds, this home is a true retreat, complete with a Glengate-designed Gunite saltwater pool, spa, and stunning stonework. Inside, the thoughtfully designed layout creates an inviting and sophisticated atmosphere. The gourmet kitchen is a chef's dream, featuring high-end appliances, quartz countertops, a spacious island, a butler's pantry, and ample storage. The sun-drenched living spaces offer seamless flow for both relaxing and entertaining, with refined architectural details throughout. The private primary suite is a sanctuary, boasting two walk-in closets, a dressing area, and a spa-like bath with a soaking tub. Two additional BRs are en-suite, while the other two share a Jack-and-Jill bath, ensuring comfort and privacy for all. The third floor bonus room is a versatile space-ideal for a playroom, media room, or home office. Enjoy summer days by the resort-style pool and outdoor entertaining area, featuring a built-in BBQ, fire pit, and lush surroundings. Located within walking distance of the Greens Farms train station and just minutes from beaches, shopping, and dining, this home offers the best of both privacy and convenience. This exceptional property is available for annual rentals and will also consider summer and short-term options.

Live in style in the Heart of Saugatuck - A Gem of a Westport neighborhood. This may be the perfect blend of comfort and convenience. Meticulously maintained unit, nestled mere minutes from Westport train, shops and restaurants. The freshly painted and deep-cleaned interior space is bathed in natural light, and boasts ample room to entertain or just chill. Also well-positioned to access Westport's vibrant Downtown, famous beaches/tranquil Long Island Sound, Y, public golf course, 95 and the Merritt-this residence is a commuter's dream. The Kitchen is well-appointed; LR, BR and Bath are all spacious. And complemented by energy-efficient HVAC systems, including a programmable thermostat, quality dishwasher and conveniently located washer and dryer. All poised to ensure your comfort year-round. Easy to clean and healthy elegance of hardwood and tile flooring creates a timeless appeal. As a resident, you'll benefit from included trash removal and snowplowing, as well as one space in the off-street parking lot, steps from the building front door. Embrace the wonderful cultural amenities the Fairfield County lifestyle has to offer!! Don't miss this exceptional opportunity to make this coastal gem in Mid Fairfield County your new home. The previous tenant stayed for 9 years! Please Note: There is ONE off street parking space with this rental. And the landlord seeks a 2 year lease. Landlord requires applications using RentSpree. Link available in Listing or ask agent.

~HIGH END LIVING~ This home is located in the "Golden Triangle" of downtown Westport. Bedford Square is a unique multi-purpose destination that includes premier residences, beautiful public areas, high-end retail and dining. It is the culmination of the renovation and restoration of the stately 1923 Bedford Mansion and historic Firehouse. Bedford Square is ideally situated in the heart of this vibrant and prosperous community at the foot of Main Street and Church Lane. This luxury rental consists of a one bedroom floor plan and all feature upscale amenities and amazing views. Whether you are looking for an alternative to New York City living or want to downsize, Bedford Square offers a lifestyle of convenience to its residents.