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55 Center St, Westport
$3,150,000
5 Beds ⋅ 5 Baths ⋅ 24163297 MLS
Located in Westport's coveted Greens Farms neighborhood, this light-filled home is perfectly sited high and dry on a private park-like acre with room for a pool and pool house. A renovated kitchen with top-of-the-line appliances and sunny breakfast nook opens to a spacious great room with stone fireplace and expansive deck overlooking the property, ideal for indoor-outdoor living. The flexible floor plan includes a rare first-floor bedroom with full bath, ideal for guests, au pair, or multi-generational living, along with a finished walk-out lower level offering additional space for recreation, media, or work-from-home needs. The primary suite features two walk-in closets and a new spa-like bath. With 5 bedrooms and 5 baths, the home offers ample space for living, working, and entertaining. Modern conveniences include city water, city sewer, natural gas, and an EV charger. Exceptional location just minutes to Greens Farms Elementary, the Greens Farms train station, Burying Hill Beach, and downtown Westport shopping and dining.

55 Center St, Westport
24 Washington Ave, Westport
$3,126,000
4 Beds ⋅ 4 Baths ⋅ 24175092 MLS
There is a moment just inside the front door, when the house introduces itself. The entrance hall-original, unhurried, exactly as gracious as 1919 intended-tells you everything. This is a home that was built when details mattered and time was taken. A century later, nothing essential has been lost. The living room and formal dining room carry that same quiet elegance, their proportions generous, their light beautiful through Anderson architectural-grade windows. Then comes the turn- into the 2013 addition, where a stunning chef's kitchen anchors a family room that opens through French doors onto a covered deck. Beyond it, a private landscaped backyard unfolds like a secret: lush, park-like, deeply planted and utterly your own. An outdoor shower with hot and cold water, a detached two-car garage, gravel driveway and an automated irrigation system make it as effortless as it is beautiful. Upstairs, the primary suite earns its name- spacious bedroom, sitting room, a spa bath, place to exhale. Three additional bedrooms, each with the soul of the original house, share a handsome hall bath.A finished third-floor now features two versatile offices and a full bath, offering flexible space ready for your next chapter. New roof, siding insulation, 4-zone A/C, sewer and water mains from 2013. 4300 SF set on .39 acres of one of Westport's most sought-after residential streets -walking distance to town.This home exudes charm and is completely, confidently, move -in ready.

24 Washington Ave, Westport
36 Bauer Pl Ext, Westport
$3,025,000
6 Beds ⋅ 6 Baths ⋅ 24161889 MLS
Better than new! This beautifully appointed 4-level home blends contemporary design with warmth, comfort, and thoughtful upgrades throughout. The heart of the home is a cook's dream kitchen with gourmet appliances, a full pantry, and a massive center island showcasing stunning finishes. Designed for both beauty and function, it opens seamlessly to the bright, welcoming family room. Together, these spaces flow onto the patio for easy indoor-outdoor living. A living room and dining room complete the inviting main level. Upstairs, the fabulous primary suite features custom closets and a spa-like bath. Two bedrooms share a chic Jack & Jill bath, while a 4th bedroom is ensuite. A laundry room is conveniently located on this level. The 3rd floor offers a bedroom, full bath, and a spacious flexible living area-perfect for guests, an office, playroom, or recreation space. The lower level is a true wellness retreat with a fully customized gym, sauna, and full bath. Perfectly set in a sought-after neighborhood, it's just a short walk to Long Lots Elementary and minutes to shopping, dining, and the Greens Farms train. With more than $100K in next-level enhancements, this residence has evolved into a truly spectacular home. Beautifully decorated, warm, and welcoming, this home is ready to enjoy from day one. Modern conveniences include city water, city sewer, natural gas, and generator readiness.

36 Bauer Pl Ext, Westport
35 Woody Ln, Westport
$3,015,000
5 Beds ⋅ 4 Baths ⋅ 24158858 MLS
Enjoy the resort lifestyle in this beautiful home! Discover unparalleled luxury and privacy at 35 Woody Lane, a meticulously renovated 5-bedroom, 3.5-bath sanctuary on 2.18 acres. Nestled at the end of a serene cul-de-sac in the acclaimed Long Lots neighborhood, this turnkey residence blends timeless elegance with modern sophistication. Step into a chef's dream kitchen featuring a massive island, custom cabinetry, high-end stainless appliances, vaulted ceilings with skylights, and seamless flow to the living areas, ideal for effortless entertaining. The exquisite primary suite offers a spa-like bath, custom built-ins, and peaceful treetop views. Generous secondary bedrooms and baths provide comfort for family and guests. The crown jewel: a resort-style backyard oasis with a sparkling gunite pool, full tennis court, hot tub, fire pit, expansive deck, and lush, private landscaping, your own secluded escape for year-round enjoyment, al fresco dining, and play. Experience the perfect fusion of luxury living and Westport lifestyle, minutes to top schools, Compo Beach, and commuter rail.

35 Woody Ln, Westport
22 Sturges Commons, Westport
$3,000,000
5 Beds ⋅ 8 Baths ⋅ 24178328 MLS
22 Sturges Commons offers the rare combination of timeless elegance, true neighborhood living, and unmatched convenience in one of Westport's most sought-after locations near the Hunt Club. Just one traffic light to the Greens Farms Station train station, this home makes commuting to New York City effortless while allowing you to return home to a peaceful walking neighborhood where charming streets converge, creating the classic community feel that is increasingly rare in Westport, CT real estate. Set on beautifully landscaped property, the home is designed for both relaxed everyday living and exceptional entertaining. The fully fenced backyard features a sparkling pool and spa, expansive outdoor spaces for dining and gatherings, and plenty of room for sports and play. Inside, warmth and sophistication define every space. The gourmet chef's kitchen opens seamlessly to a spacious step-down family room with soaring ceilings and abundant natural light, creating the perfect heart of the home. Formal living and dining rooms provide elegant entertaining spaces, while multiple options for home offices and flexible living make this property ideal for today's lifestyle. Offering 5 ensuite bedrooms, 8 baths, a third-floor office or yoga retreat, and a finished lower level complete with gym, media room, and playroom, this exceptional Westport home blends luxury, comfort, and functionality in one of the best commuter locations in Fairfield County.

22 Sturges Commons, Westport
2 Mortar Rock Rd, Westport
$3,000,000
4 Beds ⋅ 6 Baths ⋅ 24173081 MLS
Better than new, this pristine 2016 custom-built residence offers a rare standard of refinement and sophisticated excellence. With 4,000+sqft and an elevator accessing all four finished levels, the home blends modern architecture with beautifully executed transitional design. The open-concept main level features a magnificent chef's kitchen, spacious dining area, and expansive living room with gas fireplace, custom built-ins, beams, and tray ceiling. Four-inch white oak flooring runs throughout. A wall of glass doors opens to a breathtaking private setting with a remote-controlled awning, ideal for effortless indoor/outdoor living. Four bedrooms include the luxurious primary suite with tray ceiling, built-ins, and serene garden views, plus a spa-like bath with heated floors, soaking tub, double vanity, and walk-in closets. Two additional en-suite BRs and an exceptional home office with dual built-in desks, double-height bookcases, library ladder, and automated shade complete the level. The third floor offers a skylit fourth bedroom with full bath and cedar closet. The finished lower level includes a playroom/gym, office, and half bath. A 2car garage, elevator to all levels, full-house generator, security and sound systems elevate the offering. Ideally set on a desirable cul-de-sac minutes to the beach, train, town, library, and farmers market, making this an incredible location from which to enjoy all of Westport's most coveted amenities. Move-in ready and truly exceptional.

2 Mortar Rock Rd, Westport
36 E Main St, Westport
$2,999,000
6 Beds ⋅ 6 Baths ⋅ 24192039 MLS
Nestled in the heart of Westport, Connecticut, this stunning new construction residence redefines elegant suburban living with unparalleled sophistication, timeless grace and is complete and ready for immediate occupancy. Boasting six generous bedrooms and six luxurious bathrooms, the home features soaring nine-foot ceilings that bathe its expansive interiors in natural light and create an atmosphere of airy grandeur. Thoughtfully designed with premium finishes, custom millwork, and state-of-the-art systems. From the chef's kitchen with Thermador Appliances and a commanding kitchen island to the serene primary suite with a warming fireplace and a walk in closet fit for royalty; every detail invites effortless entertaining and refined daily living. Spanning three floors, this home offers exceptional versatility with a peaceful third floor sanctuary housing a private office and media room for entertainment or productivity. The finished lower lever further elevates the lifestyle with a spacious additional family room and an exercise studio, creating inviting spaces for relaxation, recreation, and personal wellness. Set against Westport's coveted landscape, located across from Winslow Park and upscale shopping, this exceptional property offers a rare opportunity to embrace modern luxury within one of Fairfield County's most distinguished communities.

36 E Main St, Westport
221 Greens Farms Rd, Westport
$2,995,000
5 Beds ⋅ 6 Baths ⋅ 24171950 MLS
The Bedford House: Architecturally and historically significant estate in Greens Farms. This exceptional property offers a rare opportunity to own one of Westport's true gems with a remarkable provenance. Set on 2.33 acres with a gunite pool & spa, court and a 2400 SF barn w/ 3 car garage, loft and more, this estate blends timeless elegance with modern comfort. Originally built in 1904 and designed by noted architects Visscher and Burley, this Colonial Revival style home has undergone thoughtful renovations over the years to preserve and enhance its original character. High ceilings, oversized windows, detailed millwork and sun-filled rooms create a sense of warmth and sophistication. Recent renovations include a new cedar roof on both house and barn, a like-new pool, spa & mechanicals, refinished hardwood floors, updated HVAC and new appliances. A unique highlight of this estate is its location across from Nyala Farms, offering scenic views of 50 acres of open meadows and fields with a deed restriction preventing any further development. Enjoy the ultimate lifestyle, minutes to the train, beaches, schools, shops and fine dining.

221 Greens Farms Rd, Westport
30 Saint Johns Pl, Westport
$2,925,000
5 Beds ⋅ 4 Baths ⋅ 24182424 MLS
Saint John Place is the street people who know Westport quietly hope opens up. It almost never does. Reimagined in 2007 by Renato Gasparian Associates and refreshed in 2022, this house has all the right moves. Inside, the main level opens up the way you hope it will. The great room stretches nearly thirty-four feet and flows into the dining area and a kitchen built around a center island, with a custom walk-in pantry right behind it. A sun room pulls in the morning light. There's a separate family room, plus a real office with a door that closes. Upstairs, five bedrooms give everyone somewhere to land. The primary suite has a spa bath with a soaking tub, a separate shower, and two walk-in closets (because who likes to share?). The laundry is up here too, in its own room. The outdoor spaces close the deal. A bluestone patio wraps around a good portion of the house with a stone fireplace. The deep flat lot is screened by mature plantings and gives you the privacy people leave town to find. You're in the heart of Westport's in-town neighborhood, which means the car can stay in the driveway. Walk to a different cuisine every night, the shops, the Library, the Westport Country Playhouse, summer nights at the Levitt Pavilion. The Saugatuck River is right there, and a celebrated omakase counter is a few minutes on foot. When you do want the car, the beach is a short drive away. Beautiful house, easy life, almost everything a walk from the door. Tour online @ 30saintjohn.com

30 Saint Johns Pl, Westport
299 Saugatuck Ave, Westport
$2,900,000
4 Beds ⋅ 6 Baths ⋅ 24169465 MLS
*THANK YOU FOR YOUR INTEREST, SELLER REQUESTS HIGHEST/BEST OFFERS BY 3PM MONDAY 6/1/26*Set on over an acre of park-like, usable property, this stunning Modern home with an oversized gunite pool is a showcase of exhilarating design. In an area known for major watefront properties as well as immediate convenience to the railroad station and all commuting routes, this home blends sophisticated elegance with an easy lifestyle. A gracious, landscaped approach brings you to the grand double-door entrance lined with windows and into a vaulted ceiling foyer. The interior captures gorgeous light all day through walls of glass & numerous skylights. The floor plan is an entertainer's dream, accommodating groups large or small in refined surroundings. The living and family rooms each have floor-to-ceiling stone fireplaces and glass doors to the rear deck. The DR has a picture-perfect view across the property. Gourmet E-I-K w/Wolf gas cooktop, Sub Zero ref/frz, Viking double ovens, pantry, center island w/seating & a breakfast area enhanced by scenic views. An adjacent sunroom transitions the space out to the deck. Two half baths complete this level. The airy atmosphere continues up front & rear stairs to the 2nd level, beginning w/a grand primary suite w/priv sitting rm, king-size BR w/pool view balcony, vast dressing rm & two lux baths. Three addl' BRs have double clsts & two full baths. Fin LL w/rec rm, office, storage. Enjoy a porch that leads to the pool/spa. 3 car garage, generator.

299 Saugatuck Ave, Westport
27 Bauer Pl Ext, Westport
$2,850,000
5 Beds ⋅ 6 Baths ⋅ 24195597 MLS
Still hoping to move before school starts? This exceptional new construction home is ready for immediate occupancy! Built by SIR Development, Westport's premier luxury builder with 30+ years of experience and 300+ homes built, this hidden gem sits at the end of a cul-de-sac in a welcoming neighborhood within walking distance to Long Lots Elementary School. The open layout spans 4 beautifully finished levels and showcases SIR Signature Home craftsmanship and designer finishes throughout. The custom eat-in kitchen with butler's pantry features sleek white cabinetry with warm oak accents, quartz countertops, handmade ceramic tile backsplash and premium Thermador appliances, opening seamlessly to the inviting family room with fireplace. The main level also offers a private study with custom oak shelving, formal dining room, mudroom and powder room. The luxurious primary suite features vaulted ceilings, a spa-inspired bath and two walk-in closets. The finished 3rd floor includes a 5th bedroom and full bath. The walk-out lower level offers custom built-ins, recreation room, gym and half bath. Outside, enjoy a level backyard, spacious granite patio with room for a pool, professionally landscaped grounds and fencing for privacy. Connected to city water and sewer with propane gas, this move-in-ready home offers the perfect blend of luxury, comfort and style.

27 Bauer Pl Ext, Westport
8 Washington Ave, Westport
$2,850,000
5 Beds ⋅ 6 Baths ⋅ 24173805 MLS
Award-winning builder proudly presents a rare, beautifully restored high Victorian Gothic home chronicled for its grace and splendor. Original architectural details artfully remain, including the only known local example of clustered colonette posts adorning the veranda. The interior showcases curved archways, carved mahogany stair banister and newel post, and detailed window trim. White oak Smallbone kitchen with La CornuFe range and mosaic marble tile opens to a dining/great room. Light fixtures and appliances were individually selected with an artist's eye. Sun-filled, the home offers six-inch white oak flooring throughout, stunning renovated baths, and all-new mechanicals with an electric heat pump and Smart home technology. The flexible layout includes a first-floor guest suite with full bath, powder room, and living room with fireplace. The second level boasts three bedrooms, one en-suite, plus a hall bath. The finished third level works as a primary suite, guest suite, or office with full bath and laundry. The detached two-car barn and garage conceal a legal one-bedroom cottage with a private garden. New kitchen, appliances, flooring, heat pump, and renovated bath; ideal for extended family or income. Both structures feature Smart eco-systems controlling security, sound, light, and climate via voice or phone. While away the hours on one of the two porches overlooking the private garden and stone wall. This coveted walk-to-town gem is an investment in loving life here.

8 Washington Ave, Westport
21 Dover Rd, Westport
$2,800,000
5 Beds ⋅ 5 Baths ⋅ 24167866 MLS
Spacious and impeccably maintained Colonial tucked away on a quiet cul-de-sac in one of Westport's most desirable locations, just moments to town, schools, trains, beaches, and everyday conveniences. Offering four finished levels, this beautifully updated home features 5 bedrooms, 4 full baths, and a powder room. Designed for both comfortable daily living and effortless entertaining, the home showcases sun filled interiors, hardwood floors throughout, and timeless architectural details. The updated kitchen opens seamlessly to the inviting family room with fireplace, while formal living and dining rooms offer additional space for gathering and entertaining. A spacious mudroom with first floor laundry adds everyday convenience. Additional highlights include two fireplaces, a brand new roof, whole house generator, and irrigation system. Set on professionally landscaped grounds with inviting outdoor living spaces and a private level backyard with room for a pool. Exceptional opportunity in a sought after Westport location. Additional professional photography will be added closer to the live date.

21 Dover Rd, Westport
23 Harborview Rd, Westport
$2,750,000
4 Beds ⋅ 4 Baths ⋅ 24163587 MLS
Located on a quiet cul-de-sac in the heart of Westport, this beautiful timeless Colonial is located at the top of one of the town's most picturesque streets, directly across from the scenic Saugatuck River. The gourmet kitchen features island seating, custom cabinetry, a serving peninsula, and a breakfast room with an abundance of natural light. The front-to-back living room with fireplace and high ceilings is adjacent to the kitchen and is also the heart of the home. Two recently renovated (Trex) decks off the kitchen and living room, along with an expansive terrace, overlook the private backyard-perfect for entertaining and outdoor enjoyment. All bedrooms are located on the second level along with two fully renovated baths. The lower level includes a family room, home gym, full bathroom and a lot of storage. The lower level has potential for a fifth bedroom. Offering 3,674 sq ft of finished living space, 23 Harborview Rd provides both comfort and flexibility, with additional unfinished space to expand within the existing footprint, if desired. Additional highlights include natural gas, public water and sewer, central air, two-car garage with room for storage, and new blue stone front walk. Commuters will appreciate the south of the Post Rd location, just 1.8 miles to the Westport Station. Harborview offers a walkable lifestyle-minutes to town 'over the foot bridge' to the library, Farmer's market, Levitt Pavillion, and restaurants. Audio/Visual

23 Harborview Rd, Westport
2 Ledgemoor Ln, Westport
$2,700,000
5 Beds ⋅ 6 Baths ⋅ 24159517 MLS
Set on a quiet, private cul-de-sac very close to town and Winslow Park, this custom five-bedroom Colonial offers an exceptional opportunity for a new owner to leave their mark and add significant value. Designed with best-in-class materials and a thoughtfully planned layout, the home retains its gracious scale, natural flow, and exceptional character. Deferred maintenance has created the chance to elevate a well-loved property and return it to the signature splendor that defined it. The main level features a gourmet kitchen with Sub Zero & Viking appliances, stone counters, custom cabinetry and an adjacent breakfast room leading to a large family room, living room with fireplace, formal dining room, and two private offices with built-ins. French doors from most main floor rooms open to a balcony overlooking a heated Gunite pool and a large, level play area. The walkout lower level has a wall of French doors and is an exquisite poolside space that includes a fully-equipped wet bar, rec/game rm, gym and a full guest suite. Upstairs, the spacious bedroom layout provides comfort and flexibility for a variety of needs. Set on 1.16 +/- acres moments from shopping and recreation, the home is being offered as-is. ***Listing photos include a mix of current 2026 images and select photos from 2009 to illustrate the full potential of the property. Please note that showings are welcomed and booked by appointment, and no open houses are planned.***

2 Ledgemoor Ln, Westport
1 Angora Rd, Westport
$2,650,000
5 Beds ⋅ 5 Baths ⋅ 24164819 MLS
One of Westport's premiere CUL-DE-SACS, WALKING DISTANCE TO ALL 3 SCHOOLS (Long Lots, Bedford, Staples), and 2.3 MILES TO GREENS FARMS TRAIN STATION, this beautifully renovated (2016/2017) 5-bedroom, 4.5-bath home perfectly blends modern luxury with timeless charm. Set on a full acre of manicured grounds, this property offers a serene retreat just minutes from every essential. The open floor plan is designed for effortless entertaining, centered around a gourmet eat-in kitchen with high-end appliances. The main level hosts three bedrooms and 2.5 baths, while the upper level serves as a private sanctuary-a lavish primary suite featuring two expansive walk-in closets, a spa-inspired bath, and a cozy lounge. The light-filled, walk-out lower level is exceptionally versatile, offering a 5th bedroom/gym, full bath, rec room, mudroom, and a dedicated home office with three separate entrances-ideal for remote work. Outside, your personal oasis awaits: a sprawling deck overlooks an inviting in-ground pool/spa, surrounded by lush greenery and a yard perfect for recreation. Unbeatable location complete with natural gas, public water, and easy access to vibrant shopping and dining. This isn't just a home-it's a lifestyle.

1 Angora Rd, Westport
79 Riverside Ave, Westport
$2,650,000
3 Beds ⋅ 4 Baths ⋅ 24147214 MLS
Sparkling river views from four floors of the most modern, chic spaces. With three bedrooms, three and a half baths, gorgeous natural light and the smartest use of 1800 sqft this waterfront home by Vita Design Group has been crafted to truly enjoy its surroundings - a perfect blend of slow tides and vibrant downtown. The main level enjoys a full wall of windows spanning the kitchen, dining area and living room. Upstairs, the primary suite fills the second floor with a serene bedroom, beautiful bath, walk in wardrobe and convenient laundry. A third floor bedroom and bath also offer a bird's eye balcony to take in the sun and sounds of rowers gliding by during the day or live Levitt tunes on a summer evening. A full lower level includes both a den/office and an en-suite bedroom. Sit riverside on the patio or cruise the river straight to the Long Island Sound.

79 Riverside Ave, Westport
34 Woodside Ave, Westport
$2,620,000
4 Beds ⋅ 5 Baths ⋅ 24185246 MLS
Steeped in history yet thoughtfully reimagined for modern living, this expanded and recently updated antique home offers the rare combination of timeless character, exceptional functionality, and a coveted location just an easy stroll to downtown Westport. Designed for both everyday living and easy entertaining, the home features warm gathering spaces and private retreats. A chef's kitchen with Thermador range and walk-in pantry opens to the home's inviting living and dining areas. Over $600K of recent updates including the stunning, newly-redesigned primary suite - a true sanctuary, with a new focal wall with custom cabinetry and gas fireplace, a well-equipped bath with dual sinks, tub and shower, plus a distinctive turreted sitting room, an idyllic space to relax. Multiple home office options. A new outbuilding elevates the property to an entirely new level. Designed as a private wellness retreat, this extraordinary Onsen-inspired space features hot and cold plunge pools, a sauna, shower, gas fireplace, and loft, creating a resort-quality experience. Outside, the sunny, level property features a new, walled-garden, crushed-stone patio and a 2nd patio, allowing for entertaining, gardening, and enjoying the peaceful surroundings. Room for pool! Town water/gas/sewer. Rich in character, beautifully updated, and uniquely equipped for modern wellness and work-from-home living, this exceptional residence offers a lifestyle rarely found in this historic, near-town neighborhood.

34 Woodside Ave, Westport
7 Fermily Ln, Westport
$2,600,108
7 Beds ⋅ 6 Baths ⋅ 24158759 MLS
Tucked away at the end of a private lane, this Nantucket-style Colonial sits on 1.21 level acres with city water, offering privacy, flexibility, and space rarely found in Westport. Rebuilt in 2006 on an existing foundation, the property combines classic shingle-style architecture with thoughtful modern living. The main residence features 5 bedrooms, 4.5 baths, and a dedicated home office. The chef's kitchen with professional appliances opens to a spacious deck overlooking the expansive backyard-ideal for entertaining or everyday living. Multiple gathering spaces include a dramatic skylit den/playroom with vaulted ceilings, perfect for a gym, media room, playroom, or recreation space. A standout feature is the full accessory apartment with 2 bedrooms, kitchenette, full bath, and its own garage, offering excellent flexibility for extended family, guests, au pair, or potential rental income. Set on flat, usable land at the end of a quiet private lane, the property provides a peaceful setting while remaining convenient to Westport amenities, schools, and commuting routes. A rare opportunity to own a spacious and versatile home in a desirable private setting. No wetlands or floozone. Agents see attachments

7 Fermily Ln, Westport
123 Greens Farms Rd, Westport
$2,600,000
4 Beds ⋅ 5 Baths ⋅ 24137404 MLS
Classic Greens Farms Colonial - Timeless Elegance Meets Modern Comfort ~ Nestled in one of Westport's most desirable neighborhoods, this beautifully updated Center Hall Colonial offers the perfect blend of timeless charm and modern luxury. Ideally located just minutes from Sherwood Island State Park-with its miles of golden sand beaches, scenic picnic areas, and sweeping views-this home provides easy access to I-95, the Merritt Parkway, and downtown Westport. Set on a picturesque property with a gentle brook at the far end of the level backyard, the home invites peaceful outdoor living with a charming front porch & back porch, expansive deck, and stone patio-ideal for al fresco dining and entertaining. Inside, a gracious two-story foyer with a curved staircase opens to a formal living room with fireplace and a formal dining room complete with butler's pantry and walk-in pantry. The gourmet kitchen features top-of-the-line new Thermador appliances, stone countertops, and a spacious dining area with access to the deck. A family room w/fireplace with Fr doors to an enclosed porch, a pvt office, and a well-designed mudroom with easy access to the two-car garage complete the main level. Upstairs, the primary suite is a true retreat, offering a fireplace, balcony with beautiful property views, walk-in closet, and luxurious bath. Three additional bedrooms share access to full baths, complemented by a large recreation/media room, half bath and convenient second-floor laundry.

123 Greens Farms Rd, Westport
3 Valley Field Rd, Westport
$2,590,000
4 Beds ⋅ 3 Baths ⋅ 24167718 MLS
*Highest and Best Offers by 5p Sunday April 26* Centrally located on a cul de sac street walking distance to shops and restaurants; minutes to beaches, train and schools. This 4 bedroom Colonial faces east/west for natural light throughout the day with a spacious floor plan and chefs kitchen opening to the family room with fireplace and sliders to the deck and professionally landscaped private backyard-perfect for entertaining. The upper floor features a gracious primary suite with 2 generous walk in closets and a renovated bath. 3 spacious bedrooms and laundry complete the upper floor. See features sheet for all updates and improvements. Welcome to 3 Valley Field Rd!

3 Valley Field Rd, Westport
4 The Fenway, Westport
$2,581,433
6 Beds ⋅ 5 Baths ⋅ 24154925 MLS
Timeless elegance in Westport's renowned Old Hill. Set on 2.22 bucolic acres w/a heated Gunite pool & picturesque pond, this expansive 5-6 bedroom,4.5 bath farmhouse blends classic charm w/thoughtful recent enhancements that delivers a renewed sense of style & energy to the home. A renovated kitchen remains the heart of the home, featuring a generous center island & a stunning, glass-walled breakfast nook which allows for basking in nature's splendor while savoring a meal. Fresh interior updates incl. a newly painted family room, updated lighting w/two new chandeliers, a modern backdrop for comfortable everyday living. This precious home has been refreshed throughout to highlight its impressive scale, open flow, & architectural character. The sun drenched primary ste is a true retreat w/a fireplace, spa like bath & generous walk in closet. A flexible floor plan offers multiple living areas & a potential in law suite-ideal for multi generational living, guests, or work from home needs. Four wood burning fireplaces add to the home's timeless appeal. Outdoors, enjoy a thoughtfully landscaped property, the pool & spa, set amidst such soothing natural surroundings. Additional highlights: city water & sewer, a whole house generator, & the exceptional privacy just moments from town. Old Hill is one of Westport's most coveted neighborhoods, known for its quiet, tree lined streets & unbeatable proximity to town, schools, & commuting. A rare opportunity to own a special home.

4 The Fenway, Westport
56 Charcoal Hill Rd, Westport
$2,555,000
5 Beds ⋅ 3 Baths ⋅ 24161256 MLS
A rare opportunity to own one of Charcoal Hill's signature properties, this exceptional Frazier Peters stone home pairs historic craftsmanship with a level of care and refinement that is increasingly hard to find. Set atop 2.3 +/- gated acres and introduced through a stunning circular drive, the residence showcases Peters' hallmark use of native stone, warm wood tones, and artisan detail, creating a home that feels both enduring and deeply inviting. More recent expansion and remodeling have sensitively enhanced the home. Sunfilled rooms with vaulted ceilings and handhewn finishes offer a balance of scale, with multiple living spaces that transition seamlessly to the outdoors. The grounds unfold in a series of thoughtfully designed moments including lush perennial gardens, winding paths, quiet terraces, and vibrant seasonal color. At the center is a sparkling, oversized pool with a waterfall spa and a fully outfitted stone pool house, which is an ideal retreat for summer living. A heated 4car stone garage with a finished upper level provides flexible space for a studio, office, or possible guest space. Every corner of the property reveals another place to gather, from sunny patios to shaded areas beneath large awnings, all wrapped in exceptional privacy yet minutes to the energy and amenities of downtown Westport. A home where history, beauty, and modern comfort come together with uncommon harmony.

56 Charcoal Hill Rd, Westport
114 Cross Hwy, Westport
$2,550,000
5 Beds ⋅ 5 Baths ⋅ 24165047 MLS
Welcome to a one-of-a-kind home in the heart of Westport - where timeless Colonial charm meets the elegance of a Parisian Estate. Set on an acre+ this home offers sophistication, space, and serenity throughout. The light-filled LR stuns with vaulted ceilings, HW floors, a wood-burning fireplace, and French doors opening directly to the deck and pool - the perfect setting for everyday living or entertaining. The formal DR offers its own fireplace, blending classic character with warmth and style. The chef's kitchen features two iconic AGA stoves, a walk-in pantry, skylights and a large center island. A charming covered porch offers peaceful morning coffee or evening outdoor dining. Upstairs, the primary suite, is a private sanctuary with vaulted ceilings, sunny sitting room, HW floors, walk-in closet, and spa-like bath incl cast iron soaking tub, oversized shower and elegant finishes. Add'l bedrooms 1 en suite the other w hall bath on the 2nd floor and 2 more Bedrooms on the 3rd floor w Hall Bath are bright and spacious, each w/ HW floors and serene views of the pool and gardens. The LL offers gym area, work space, storage and access to 2 car garage. The fully fenced backyard is a private paradise. Stone walls, mature English gardens and spectacular In-ground pool with auto cover add to the magic of this private oasis. Whole House Generator. Minutes to schools, shopping and town offering the rare combination of luxury, charm, privacy and convenience.

114 Cross Hwy, Westport
140 Roseville Rd, Westport
$2,520,000
4 Beds ⋅ 3 Baths ⋅ 24132813 MLS
Perfectly sited on 1.59 acres, this 4-bedroom, 3-bath antique home invites a lifestyle defined by warmth, ease, and understated elegance. Original wideboard floors, an impressive hearth fireplace, and beautifully preserved details create a sense of history, while the open, light-filled layout supports a modern way of living-whether hosting gatherings or enjoying quiet moments at home. The main level is designed for flexibility and comfort, with a first-floor bedroom or office that easily adapts to guests or work-from-home needs. Upstairs, the primary suite offers a calming retreat with a walk-in closet and full bath. Two additional bedrooms, a hall bath and small study provide space for family, creativity or focus. Thoughtful updates, including newer mechanicals and roof ensure a turnkey experience without compromising the home's character. Outdoors, life naturally extends into a private, resort-like setting. A gunite pool and spa invites long summer afternoons, while the expansive, sun-filled lawn sets the stage for entertaining, play or simply unwinding. The detached 2-car garage with heated loft offers a versatile escape-ideal for home gym, studio or relaxed gathering. Moments from town, dining, and all transportation, this is a delightful retreat where every day living feels both effortless and elevated.

140 Roseville Rd, Westport
32 Berndale Dr, Westport
$2,450,000
5 Beds ⋅ 4 Baths ⋅ 24157886 MLS
OFFERS DUE AT NOON ON MONDAY APRIL 13TH! In the heart of Westport, where charm meets modern living, the expanded cape at 32 Berndale Drive delivers the perfect blend of space, style, and location. Nestled on a quiet, sought-after street just moments from Bedford Middle School and Staples High School, this 5-bedroom, 4-bath residence offers exceptional versatility for today's lifestyle. A welcoming foyer leads into inviting living spaces-including a sun-filled living room with a fireplace, a spacious dining room perfect for gatherings, and a cozy den anchored by a second fireplace. The updated kitchen impresses with top-of-the-line stainless steel appliances, granite countertops, plus ample workspace and storage. Upstairs, the primary suite is a serene retreat featuring a spa-inspired bath with radiant heated floors and a luxurious steam shower. Additional bedrooms, including three on the main floor, provide plenty of room for family, guests, or dedicated office space. The lower level expands your options with a recreation area, workout room, bedroom, laundry, and a full bath-ideal for guests or extended family. Additional highlights include a 2-car attached garage, whole-house generator, and mudroom entry with thoughtful built-in cabinets for easy daily living. An adjacent sunroom makes a perfect home office or studio, overlooking the private backyard. This exceptional home combines comfort, style, and one of the best locations in town.

32 Berndale Dr, Westport
52 Meadow View Dr, Westport
$2,425,000
5 Beds ⋅ 6 Baths ⋅ 24175276 MLS
Beautifully set on a side street rise, this stately center hall Colonial has a traditional 4 bedroom, 3.5 bathroom floor plan, plus a bonus wing to suit your flexible space ideas! The main floor includes a front to back stretching living room with the sweetest screened porch, a dining room, an eat-in kitchen with dining area and breakfast bar, and a spacious family room. Upstairs, the primary bedroom has a full bath, three closets and beautiful views of the private property and pool! There are three additional bedrooms, one with an adorable play nook, and a hall bath. The "wing" connects to the main floor and is made up of a living room, office, 2 bedrooms, a full bath and there is a rec room, half baths, storage and a separate entrance on the lower level. A great space for guests, flexible use, and zoned as a legal two family. The 1.35 acre property is bright and blooming already, and the pool is ready for summer fun! Located so close to schools, town and transit, 52 Meadow View Road is ready to be enjoyed!

52 Meadow View Dr, Westport
171 Compo Rd S, Westport
$2,425,000
4 Beds ⋅ 5 Baths ⋅ 24168078 MLS
Tucked away in a peaceful, private setting, Hidden Ledge offers the best of Westport living in an ideal Saugatuck/Compo location. This stunning brand-new 4-5 bedroom home combines thoughtful design, quality craftmanship, and effortless access to the area's most loved destinations. Walk along sidewalks or bike the designated bike routes to Compo Beach, Longshore, Saugatuck, downtown shops, acclaimed restaurants, the train, library and Westport's coveted Levitt pavilion. Designed and built by local HOME Design Build, this 3800 SF residence features a clean, timeless aesthetic with an abundance of light thanks to its southern and western exposures. Every detail has been carefully curated, from vertical channel accents, Visual Comfort Lighting and Thermador appliances to the wide-plank white oak floors, custom closets and over-sized Marvin windows. A must-see home in the heart of one of Westport's most desirable locations. #171 Compo Rd. S is one of two NEW Constructions currently being built on a private rear parcel set back from Compo Rd. S. offering city water, sewer and buried power lines. ** The driveway will be maintained jointly by both 171 & 169 Compo Rd. S. As permitted, the property has been organized as a land condominium to allow for the 2 New Constructions to be sold separately.

171 Compo Rd S, Westport
13 Riverfield Dr, Westport
$2,418,000
4 Beds ⋅ 4 Baths ⋅ 24159296 MLS
Nestled in a country setting with 2.04 acres of flat, private, beautiful property on one of Westport's most idyllic and picturesque walking streets is a warm and light filled Colonial, in a serene and wooded neighborhood setting. Inside and out, this home has been beautifully updated and maintained. The interior has all the right rooms in all the right places. Rooms are spacious. Main Level: Foyer, Formal Liv/Din Rms, Family Rm w/vaulted ceiling, Kitchen, Breakfast Room, Office and access to Screened-in Porch and large, outdoor Deck. The Lower Level has another Family Rm, Office/Storage Rm, Full Bath, Sauna, Mudroom and tons of storage. Outdoors, you will find a beautifully set tennis/pickleball court with basketball hoop. The peacefulness of this property makes the perfect setting for parties and everyday enjoyment. All of this only 1.3 miles to Coleytown Elem/Middle Schools, less than 3 miles to downtown, and less than 5 miles to the Westport Train station!

13 Riverfield Dr, Westport
18 Silver Brook Rd, Westport
$2,400,000
4 Beds ⋅ 5 Baths ⋅ 24191350 MLS
Welcome to 18 Silver Brook Road, a beautifully updated and meticulously maintained home set on a level, private acre in one of Westport's most beloved neighborhoods. Located in the sought-after Silver Brook/Bonnie Brook community, this move-in ready residence offers the perfect blend of timeless charm, generous living spaces, and exceptional indoor-outdoor living. The spacious eat-in kitchen flows seamlessly into the vaulted family room, creating a natural gathering place for everyday living. Formal living and dining rooms, a sun-filled office, and a spectacular great room with exposed beams, a fireplace, and French doors opening to the terrace provide exceptional spaces for entertaining and relaxing alike. Upstairs, the serene primary suite features vaulted ceilings, dual walk-in closets, and a spa-inspired bath. Three additional bedrooms, well-appointed baths, and a dedicated laundry room complete the second level. Lovingly cared for and thoughtfully enhanced, the home has seen extensive recent improvements, including pool equipment and liner replacement, smart home upgrades, energy-efficiency enhancements, chimney reconstruction, basement waterproofing, and significant landscaping improvements. Every detail has been attended to, allowing the next owner to move in and immediately enjoy everything this exceptional home has to offer.

18 Silver Brook Rd, Westport

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