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122 Beachside Ave, Westport
$24,210,000
5 Beds ⋅ 6 Baths ⋅ 24066972 MLS
A GOLD COAST opportunity: 6.6 acres of pristine estate living culminating at 400 ft of direct Long Island Sound waterfront.A winding drive from the famed Beachside Ave enclave leads past the tennis pavilion, through the shaded trees and into a cobblestone courtyard with fountain and perfectly manicured garden entry.Stepping through the front door, the striking view of blue water tops the lush green lawns like a painting. The main fl of this Roger Ferris shingle style colonial was designed for luxury coastal living, the main living room, sun room, and kitchen all pour out onto the gorgeous south facing patio through endless walls of windows & French doors.Each space meticulously finished to be comfortable for everyday living while also ready for seamless indoor/outdoor entertaining at a moment's notice with smart & almost sneaky placement of pocket doors, cocktail room & butler's pantry. The main house boasts spacious 5 bdrms. The primary suite, consisting of a spectacular bedroom with rustic barn wood ceilings & water views in every direction is balanced by the clean lines of a recently redesigned sleek sitting room & the modern bath + dressing room done in crisp whites. There are 2 multi room bedroom suites finished in New England resort style & a guest wing w/ 2 additional bedrooms, bath & separate entrance hall. The home has 4 garages + a covered bay, a full basement w hotel level laundry room, storage, catering prep room & immaculate utility rooms geothermal home heating.

122 Beachside Ave, Westport
128 Beachside Ave, Westport
$20,790,000
1 Beds ⋅ 1 Baths ⋅ 24129357 MLS
6.62 acres of Long Island Sound waterfront property. A stunning modern architectural masterpiece. The structure is anchored by a 75 ft indoor pool and wall of seamless glass windows that feel connected to the water beyond , the single story structure also holds a kitchen, lounge and bath. The Red Barn is a secondary structure in the orchard section of the property - designed as an artist's studio on the main floor, there is also a bedroom, bathroom and living area on the second floor.

128 Beachside Ave, Westport
92 Beachside Ave, Westport
$15,500,000
8 Beds ⋅ 9 Baths ⋅ 24130997 MLS
Once-in-a-Generation Historic Estate set on a most coveted stretch of Fairfield County's Gold Coast, with a remarkable provenance as a former Bedford family estate. This extraordinary property is a rare offering that blends timeless architecture with iconic waterfront living. With sweeping views of Long Island Sound, the home's stately presence is matched only by its stunning 3.55 acres of parklike grounds and over 200 feet of waterfront, including a waterfront pool, well-equipped pool house, and 3-bedroom guest cottage. Approach through the gated stone walls and travel the tree-lined drive, enjoying the unfolding Sound views. Rich with original character, the main residence evokes the grace of a bygone era with leaded glass windows, impressive millwork, and grand gathering spaces featuring soaring ceilings designed to showcase the breathtaking views. Included in the home's magic is this wonder: a sailing ship imported from England, reconstructed on site to create a one-of-a-kind study. Generations have hosted parties on these magnificent grounds, enjoyed quiet mornings by the seawall or spent a day boating from the mooring off its private beach. This former longtime home of Lucie Bedford and her husband, Briggs Cunningham - race car driver and America's Cup winner - is a landmark opportunity to own a storied piece of Westport's history along prestigious Beachside Avenue. A one-of-one opportunity to carry on this legacy of luxury and history at this iconic waterfront estate.

92 Beachside Ave, Westport
26 Beachside Ave, Westport
$9,000,000
24035347 MLS
NEWLY PRICED! Oversized 3.30 Private Waterfront Acres with 254 feet of Long Island Sound frontage located on the Premier Gold Coast of Connecticut is ready to be molded into your PERFECT Home... 26 Beachside Avenue is both a most sought after Westport address and NOW has over 254 feet of Direct Long Island Sound frontage. This southern facing, cleared, and elevated land is direct water front with private beach access as well as an expansive seawall. The possibilities are endless for this oversized lot. Transform these panoramic views into your perfect vision and start enjoying spectacular sunrises everyday. Located in the heart of Green Farms, Westport, walking distance to train station, close to schools and shopping. This lot is Builder Ready. Create Your Dream Today.

26 Beachside Ave, Westport
19 Beachside Cmn, Westport
$8,986,000
7 Beds ⋅ 9 Baths ⋅ 24158698 MLS
Like-new custom modern home with open-concept living designed for comfort and entertaining. The main level connects the family room, dining room, office, and chef's kitchen featuring Sub-Zero and Wolf appliances, invisible speakers, quartzite countertops, custom cabinetry, two large islands and multiple sliding glass doors leading to an outdoor oasis. The spacious pantry includes custom shelving, an ice maker, and built-in water dispenser. The primary suite features cathedral ceilings, gas fireplace, a private balcony, expansive walk-in closet, and a spa-inspired bath with radiant heated floors, steam shower, soaking tub, and wet bar with refrigerator. The second level also includes four additional en-suite bedrooms and a spacious laundry room with double washer and dryer and custom cabinetry. The third-floor lounge with wet bar and roof deck provides additional entertaining space along with another bedroom and full bath. The finished lower level offers a great room with wet bar, temperature-controlled wine room, gym, media/playroom, and en-suite guest bedroom. Outdoor spaces feature bluestone patios, a heated covered porch with fireplace, built-in grill, heated Gunite pool and spa and heated walkways. Additional highlights include Savant smart home system, Lutron lighting, whole-home audio, radiant heat, multi-zone HVAC, generator, and three-car garage with electric vehicle charger. Walk to Burying Hill Beach, Greens Farms Academy, and Greens Farms train station.

19 Beachside Cmn, Westport
109 Morningside Dr S, Westport
$7,000,000
24137565 MLS
109 Morningside Drive South is an exceptional and rare offering in the highly sought- after Greens Farms neighborhood in Westport CT. Spanning 12.3 acres, this expansive property presents a unique opportunity to create a one-of-a-kind estate in one of Fairfield county's most desirable locations. Nestled amongst prestigious homes, this property offers endless potential for those seeking to build something special. Whether you envision a grand single-family residence or a private compound, the parcel provides an extraordinary canvas for your vision.

109 Morningside Dr S, Westport
7 Roshab Ln, Westport
$6,649,000
6 Beds ⋅ 8 Baths ⋅ 24102877 MLS
Now complete! Set on over 2 acres in one of Westports's most desired neighborhoods, this stunning new construction by HOBI award winner, Rick Benson, blends modern luxury with timeless design. Surrounded by mature trees, this home offers privacy & serenity minutes from trains, town, shopping & beaches. Discover luxurious living spaces, 6 ensuite bedrooms, 7 full/1 half baths, seamless flow between open-concept living & refined formal spaces. The gourmet kitchen is a chef's dream, featuring 60" Wolf range, Sub-Zero appliances, galley sink, fridge drawers, hidden shelves next to range, & a working pantry. Elevator-ready for 5 stops, the home is built for long term comfort. Entertain effortlessly in the family room containing a full wet bar with wine column & beverage center; the room opens to the covered porch & outdoor kitchen & dining area. The resort-style backyard is anchored by a 20'x40' foot pool with internal spa & sunning platform, looking over the extensive graceful lawn. The sumptuous primary suite is marked by vaulted ceiling, spacious deck with glass railings & wellness room. Additional highlights include 10" ft ceilings on the 1st floor, 9" on other floors, Lutron lighting, 2 instant hot water heaters, 4 gas fireplaces, fabulous walk-out lower level with full bar, gym, large gathering space & wine tasting area. Space exists for a 1000 sq ft ADU or 300 sq ft pool house, huge unfinished 3rd floor awaiting your ideas. Schedule your private tour today.

7 Roshab Ln, Westport
6 Gray Ln, Westport
$6,550,000
5 Beds ⋅ 5 Baths ⋅ 24184591 MLS
Appraisers please take note: closing price does not fully represent offer price. **Sellers request all offers to be submitted by Sunday 6/28 at noon.** A WATERFRONT offering in one of Westport's most coveted enclaves. This beautifully composed estate is gracefully sited on more than two private, tree-lined acres, encompassing sweeping views of Sasco Creek, Southport Beach, and Long Island Sound while preserving an exceptional sense of seclusion. Designed to maximize its remarkable setting, the home captures water views from nearly every room and showcases timeless architectural details including custom millwork, random-width hardwood flooring, three fireplaces, cathedral ceilings, and formal and informal living spaces rarely seen in today's homes. Set amid beautifully landscaped grounds with perennial gardens and expansive entertaining terraces, this private oasis invites alfresco dining beneath breathtaking sunsets and sunrises. The home features five bedrooms including two primary suites, a guest suite, chef's kitchen, great room, sunroom, and more. Located between prestigious Beachside Avenue and historic Southport Village, you are moments from beaches, boutique shopping, acclaimed restaurants, and the enduring charm of Connecticut's Gold Coast. Framed by mature evergreens, flowering dogwoods, mountain laurel, and rhododendron, the property delivers an exceptional combination of privacy, scale, and proximity - just 55 miles from NY

6 Gray Ln, Westport
36 Maple Ave S, Westport
$5,199,000
6 Beds ⋅ 7 Baths ⋅ 24165045 MLS
Beautiful Georgian Colonial style home in desired Greens Farms neighborhood design by renowned architect Judith Larson. A fabulous Redcoat design team make this home a must, perfect for todays's lifestyle with a classic feel. This 6 bedroom residence is set on a flat, level.70 acre property embodying a perfect synergy of architectural excellence and an enviable location. Crafted for modern living with a Westport nostalgic feel. This 7,000+ square-foot home showcases unparalleled design and meticulous construction across two main levels that optimize light and space. Redcoat homes construction is several grades above spec builders, attention to detail , light, and space that work for today's living are imperative in his homes. The main level features a designer kitchen, formal dining room, family room, office, and living room. An additional laundry and changing room are on the first floor. Enhanced by Redcoat's signature oversized windows, doors, and 10-foot ceilings. The second level boasts 4 bedrooms, including a luxurious primary suite, along with the main laundry area. The third floor includes an additional family space and an office. The lower level includes a sixth bedroom, gym, and playroom. Additional amenities comprise: a three-car garage, an approved pool site.

36 Maple Ave S, Westport
11 Beachside Cmn, Westport
$5,000,000
5 Beds ⋅ 8 Baths ⋅ 24113390 MLS
A true Westport icon, 11 Beachside Common is one of the most architecturally distinctive homes on the Connecticut coast-known to anyone who's ever strolled Burying Hill Beach. Set on 2.6 waterfront acres, the property offers sweeping southern views over Sherwood Island and Long Island Sound, with sunsets that rival the Low Country and birdlife that fills the surrounding marsh with movement and sound. With water access for kayaking and paddle boarding, it's a nature lover's paradise wrapped in high design.Originally built in 1971, the home underwent a $13M transformation under acclaimed architect James Biber of Pentagram. The goal: not to create rooms, but to dissolve them. Nearly 9,000 sq ft of open, gallery-like living space is unified by a 150-ft handmade tile path that runs the length of the main level. A soaring central room with exposed aluminum column is flanked by playful architectural elements -domes, portholes, skylight tubes, and a floating staircase.A 3-story "tower," designed as the intellectual center of the home, offers 360-degree panoramic views and quiet workspace. This is a home where design, art, and imagination intersect-and where brilliant minds have found inspiration. From Academy Award winners to world-renowned scientists and adventurers, this home has drawn extraordinary lives. If genius gravitates toward whimsy, perhaps it's because whimsy makes room for wonder-and for those bold enough to see differently.

11 Beachside Cmn, Westport
10 Tierney Ln, Westport
$4,625,000
5 Beds ⋅ 8 Baths ⋅ 24103087 MLS
This is the second of 2 custom homes, beautifully sited at the end of a private lane in the heart of Greens Farms. Combining classic design with modern detailing by an established local builder of premier residences, this masterfully crafted home is sure to delight even the most discerning buyer. The main level showcases expert millwork and warm white oak accents throughout, flowing from the Living and Dining Rooms with paneled walls into the Study with built-in cabinetry. The Chef's Kitchen with Wolf and Cove appliances adjoins the sunny Family Room which opens to a picturesque 1.4 acres with salt water Swimming Pool and Spa, surrounded by a handsome granite patio. An elegant Primary Suite with fireplace, luxurious Bathroom, dressing area and 2 walk-in closets with custom cabinetry, plus 4 additional Bedrooms with 3 additional Baths, a Family Room/Lounge and Laundry Room grace the second level. The third floor has a Playroom and an additional Flex Space/Office. The lower level features a Gym with mirrored walls and rubber floor, a Sauna, a handsome Bar and gathering area with a glass garage door that opens to a patio, a full bath plus an additional room with a private entrance for Media, Office or use as a Bedroom. Available for immediate occupancy.

10 Tierney Ln, Westport
11 Wake Robin Rd, Westport
$4,560,000
5 Beds ⋅ 6 Baths ⋅ 24167814 MLS
Just completed and ready for immediate occupancy, this beautifully crafted new construction home is set on a quiet cul-de-sac in the desirable Greens Farms area. Situated on a level one-acre property with a pool, the home is filled with abundant natural light and offers a thoughtful, well-balanced layout designed for both everyday living and entertaining. The stunning kitchen opens to a dramatic double-height family room, creating an inviting central gathering space. With five-plus bedrooms, including a first-floor primary suite featuring a spacious walk-in closet and a well-appointed bath, the home provides flexibility to suit a variety of living arrangements. Two laundry rooms add convenience, while high-end finishes and attention to detail are evident throughout. A fully finished lower level offers additional living space with a gym, recreation area, and more. Ideally located for commuting, with easy access to town, beaches, shopping, and transportation.

11 Wake Robin Rd, Westport
6 Clapboard Hill Rd, Westport
$4,500,000
6 Beds ⋅ 6 Baths ⋅ 24193530 MLS
At the top of Clapboard Hill, through the gate and over the brick drive, an iconic Westport Colonial welcomes with an immediate feeling of privacy and classic beauty. The main entrance reveals a double height foyer, sweeping staircase and historic charm. The formal living room spans front to back with multiple seating areas flanking the original fireplace. A smart, chic library lands just off the center hall, followed by the gorgeous dining room ready for family dinners and holiday entertaining. The white and bright kitchen is anchored by an island and includes a full butler's pantry, a prohibition era wine closet, and the sunniest breakfast room overlooking the patio. The family room is so spacious with room for lounging by the fire and piling in for movie nights. Upstairs holds a total of six bedrooms. The primary suite includes a beautiful bath, multiple walk-in closets and sweeping views. A sweet set of bedrooms share a Jack and Jill bath. There are three additional bedrooms, a full bath, and a laundry room. The third level is fully finished as a recration room. The two acre property is fully irrigated, professionally landscaped, and sectioned for pool, play, patio spaces and privacy. The stunning pool includes a lap lane and the pool house is cabana perfection with a main room, poolside necessities (including a secondary bbq!) and full bath. There is a three car garage and automatic gate to split driveway. So close to beaches, GF train stations, schools and town!

6 Clapboard Hill Rd, Westport
26 Morningside Dr S, Westport
$4,350,000
7 Beds ⋅ 8 Baths ⋅ 24147443 MLS
Now fully complete, this newly built residence in Greens Farms offers a rare blend of architectural presence, modern comfort, and understated luxury. Crafted by a seasoned Westport builder with a fresh perspective, the home delivers a level of finish and warmth that distinguishes it from typical new construction. The outdoor experience is now fully realized with a custom gunite pool and over $150,000 of additional landscaping, creating a private, resort-style setting designed for everyday enjoyment and entertaining. Inside, a chef's kitchen anchors the main level with bespoke cabinetry, professional appliances, and a generous island that naturally brings people together. Open dining and family spaces flow seamlessly, complemented by a private library and an oversized three-car garage designed for the car enthusiast. The primary suite is a serene retreat with sitting area, spa-inspired bath, and custom dressing room, joined by four additional en-suite bedrooms and second-floor laundry. The third floor offers a full movie theater, office, and game area, while the finished lower level features a climate-controlled wine room, sauna, gym, and secondary prep kitchen with full-size refrigerator and freezer ideal for hosting or extended stays. Bluetooth audio, designer lighting, integrated TVs, and three fireplaces enhance the home throughout. Minutes to train to NYC, Compo Beach, Westport's best amenities, this move-in-ready home represents exceptional value at this price.

26 Morningside Dr S, Westport
49 Hillspoint Rd, Westport
$4,225,000
5 Beds ⋅ 7 Baths ⋅ 24119112 MLS
Set discreetly at the end of a long drive and screened by mature landscaping, this exceptional Hillspoint residence offers a surprising sense of privacy in one of Westport's most convenient coastal settings. Just moments from Longshore Club Park, Compo Beach, town and train, it perfectly blends luxury, lifestyle and accessibility. Inside, soaring ceilings and sun-filled spaces create a light, airy flow enhanced by high-end finishes throughout. Designed for everyday living and effortless entertaining, the expansive chef's kitchen with double refrigerators, dishwashers and ovens anchors the home, opening to inviting dining and gathering spaces. Upstairs, a private family wing with its own library and a finished third-floor retreat provides flexible space for study, play or creative pursuits. The walk-out lower level elevates the experience with a laser home theater, media lounge, gym and game room for year-round enjoyment. Outdoors, a heated saltwater pool and spa, pergola and sweeping lawn framed by roses and grasses create a private resort setting. Savant smart home technology offers integrated music inside and out, lighting controls, automated shades, full irrigation, landscape lighting and comprehensive security, all managed from your phone. Peaceful, refined and unexpectedly serene, this home lives like a retreat while placing you at the center of everything Westport has to offer.

49 Hillspoint Rd, Westport
365 Greens Farms Rd, Westport
$3,850,000
6 Beds ⋅ 5 Baths ⋅ 24124482 MLS
Generously sited on 2.15 stunning acres in Greens Farms, the Joseph H. Wakeman House is a perfect example of New England ingenuity and warmth. Built in 1840, this distinguished Federal-style residence was thoughtfully reimagined in the 1930s by an owner intent on showcasing its craftsmanship and enduring quality. The current residents were similarly captivated by its character and history. Located in the heart of one of Westport's most coveted and convenient neighborhoods, the park-like grounds, with sweeping lawns and meandering stone walls, are enchanting in every season. Inside, the home is warm and inviting-walls painted in pristine white provide a clean backdrop that highlights architectural details and period millwork. Wideboard flooring and 9-foot ceilings extend throughout, underscoring the timeless proportions and charm. Welcomed through double front doors, guests are immediately drawn to the gracious front hall or library, lined with bookshelves and anchored by the home's original staircase - a space so inviting, it is hard to leave. The elegant LR, with its rare double fireplaces, easily accommodates a grand piano, while the intimate formal DR-also with a fireplace, encourages evenings when friends linger. A butler's pantry connects seamlessly to the gourmet kitchen, which opens to the terrace and is bathed in natural light.The spacious FR features wide French doors to the yard, while a charming mudroom offers a practical yet welcoming entry.

365 Greens Farms Rd, Westport
18 Woodhill Rd, Westport
$3,800,000
6 Beds ⋅ 7 Baths ⋅ 24144655 MLS
Nestled near the end of an upscale cul-de-sac in prime Greens Farms, the newest SIR SIGNATURE Home blends timeless design with modern luxury on beautifully flat, private grounds. A heated gunite pool with auto cover anchors the expansive backyard w/ two connecting raised patios creates a true indooroutdoor retreat. Inside, sunfilled spaces showcase the craftsmanship SIR is known for. High ceilings, custom millwork, wide-plank oak floors, and a stunning chef's kitchen opens to a spacious family room w/ a distinctive beamed ceiling & walls of glass overlooking the property are just some of the highlights which place this fine home in a class of its own. The purposeful layout offer effortless flow for everyday living and entertaining. Six bedrooms include a serene primary suite w/ spa inspired bath incl floating white oak vanity and generous dressing room. The finished third floor provides flexible bonus space w/ bath for work or play, while the fully finished walk-out lower level offers recreation, fitness, and media options. The private office with custom cabinetry provides an ideal place to work in serene surroundings. Thoughtful amenities like designer lighting, a terrific mudroom, pantry, and attached garage complete this exceptional home. Close to Greens Farms school, beaches, walk to Westport Tennis Club and only 1.6 mi to train. A rare opportunity to buy from Westport's most trusted builder with over 300+ completed homes in one of the town's most coveted neighborhoods.

18 Woodhill Rd, Westport
249 Greens Farms Rd, Westport
$3,480,000
7 Beds ⋅ 9 Baths ⋅ 24132302 MLS
Storied and superbly restored, 'The Lookout' at 249 Greens Farms Rd blends the grandeur of a 1907 Victorian with todays modern luxury. Privately set among perennial gardens and antique copper beeches, this iconic 16-room residence offers a gracious floor plan with elegant formal spaces, a chefs eat-in kitchen, media room, wine cellar, and inviting family areas. Original architectural details shine alongside impeccable updates. The primary suite features a spa bath and custom closets; three additional bedrooms offer flexible space. Outside, relax by a sparkling pool or host gatherings on the lush, landscaped lawn. An adjacent lot for added privacy or future expansion is also available. A true Westport landmark, steps from town, schools, and rail, this is a rare opportunity to own an estate rich in character and comfort. Shown by appointment

249 Greens Farms Rd, Westport
1 Flower Farm Ln, Westport
$3,450,000
5 Beds ⋅ 8 Baths ⋅ 24148553 MLS
Absolutely exquisite colonial is located on one of the most sought after neighborhoods. This home will greet you w/a mahogany front porch that leads inside to a grand foyer. This timeless residence boasts a custom kitchen w/high-end appliances, a Butler's pantry, large island & the convenience of a desk station. The elegant formal living room features a cozy fireplace, while the family room offers a stone fireplace, coffered ceilings with French doors leading to a bluestone terrace, overlooking the gorgeous landscaped property. Gather in the sophisticated formal dining room w/yet another fireplace. The main level graciously accommodates a guest bedroom suite with a full bath, walk-in closet, as well as a study adorned w/Cherrywood & built-ins, leading to a serene blue stone screened-in porch. The main level also has the convenience of 2 powder rooms & a mudroom, as you enter from the 3 car garage. Upstairs, discover the luxurious primary bedroom w/a sitting room, 2 walk-in closets, changing room, & spa-like bathroom w/a claw hydro tub, shower & private balcony access. Additionally, there are 3 more bedrooms each w/a custom full bathroom, along w/a generous bonus room. The fully finished 3rd floor offers versatility with a half bath. Entertain on the lower level, featuring a theater room, gym w/sauna, family room, wine room & powder room. Outside, the meticulously landscaped grounds showcase an inground gunite pool, hot tub, pool house w/a full bathroom overlooking 2 acres.

1 Flower Farm Ln, Westport
91 Turkey Hill Rd S, Westport
$3,200,000
5 Beds ⋅ 6 Baths ⋅ 24166415 MLS
Beautifully sited in prestigious Greens Farms this timeless 5 BR, 6BA clapboard-and-stone Colonial offers stunning architecture & resort like privacy just moments from train, town & beaches. A gracious front porch & exquisite landscaping create an immediate sense of presence; classic, composed & quietly impressive. Inside, a soaring entry filled w/natural light introduces interiors defined by beautiful scale, 9-ft ceilings & gracious flow. Formal living room w/gas fireplace & dining room w/wet bar lend elegance to entertaining while a handsome office/den w/custom built-ins offers warmth & intimacy. The kitchen is refined & inviting w/quartz countertops, Sub-Zero appliances, walk-in pantry & breakfast/dining area opening to bluestone terrace. The expansive family room anchored by a substantial stone fireplace creates a natural gathering place & French doors open seamlessly to the outdoor living space. The main level also includes a secondary entry w/back staircase, laundry room, additional office & 2nd powder room. Upstairs the primary suite is a true retreat w/oversized walk-in closets, dressing area & spa-like marble bath. 4 additional generously proportioned bedrooms including two en-suite offer flexibility for family & guests. Finished 3rd fl ideal for playroom, gym, media room, 6th BR. Outside sprawling grounds, expansive bluestone terraces, exceptional masonry & stunning saltwater gunite pool & spa create a private oasis w/serene resort-like feel. Impeccably presented.

91 Turkey Hill Rd S, Westport
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
34 Sasco Creek Rd, Westport
$3,135,000
3 Beds ⋅ 5 Baths ⋅ 24133270 MLS
Walk to the beach! Rare opportunity to own 2 flat acres encompassing a renovated beach house and a remarkable modern barn designed with walls of glass. All uniquely located in the Greens Farm community of Westport, boasting LI Sound beach access and abutting the Connecticut Audubon trails. An updated 3-bedroom Cape offers one level living with a primary suite on the main floor and two bedrooms on the upper level. A glass enclosed sunroom with French doors opens to a private patio overlooking the expansive fenced yard. The beautifully renovated two story barn with skylights and oversized windows capture an abundance of the surrounding light from the rear Western exposure. Two half baths and an upper-level space for work or relaxation complete the barn. This seaside beach residence with glorious grounds features specimen trees, wildflowers and more. The main home offers 1882 square feet. The barn provides an additional 2,098 square feet. This seaside beach residence uses solar panels and has a generator. Vacation living can be embraced everyday!

34 Sasco Creek Rd, 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
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
86 Maple Ave S, Westport
$2,345,000
4 Beds ⋅ 4 Baths ⋅ 24148769 MLS
Renovated, refreshed, and move-in ready, this sunfilled Greens Farms gem offers the perfect blend of charm, style, and modern comfort. Set on a beautifully landscaped, level acre with gunite pool and expansive patio, the outdoor living experience is exceptional. Fresh paint inside and out, a new pergola, and thoughtful landscaping create irresistible curb appeal. Step inside and feel instantly at home. The inviting Dining Room and elegant Living Room with fireplace flow seamlessly toward a private office. The updated eat-in kitchen features gleaming new countertops and opens directly to the dramatic Great Room, where soaring ceilings and French doors frame views of the tiered patio, lush grounds, and pool. Upstairs, you'll find four bright bedrooms and two full baths. The spacious Primary Suite is a true retreat, complete with a sitting room, two walk-in closets, a well appointed bath, and striking vaulted ceilings. The heated lower level offers flexible bonus space, ideal for a playroom, gym, or creative studio. Two car garage with new mudroom. A home that feels as good as it looks. You're going to love it.

86 Maple Ave S, Westport
11 Dogwood Ln, Westport
$2,337,500
4 Beds ⋅ 3 Baths ⋅ 24098937 MLS
Experience the best of Westport living in this stunning Mid Century Modern residence set on 1.87 prime acres in the heart of town. This is all about the property! Tucked away on a beautifully landscaped property, this 4-bedroom home offers the perfect blend of privacy, modern design, and everyday convenience. Inside, expansive windows bathe the open living spaces in natural light, with soaring ceilings and a seamless indoor-outdoor flow. The spacious kitchen, elegant dining area, and inviting living room create an ideal setting for entertaining. Retreat to a serene primary suite with views of the picturesque grounds. Step outside to your own private oasis featuring a sparkling in-ground pool, lush lawns, and mature plantings- fully fenced and perfect for relaxation or play. Enjoy the combination of public water, and town sewer. Located minutes from downtown shopping, restaurants, beaches, top-rated schools, and the train. A truly exceptional offering in one of Westport's most sought-after locations.

11 Dogwood Ln, Westport
342 Greens Farms Rd, Westport
$2,100,000
4 Beds ⋅ 5 Baths ⋅ 24122231 MLS
From city politics to select suburb - this home offers you the desired change with NYC still within reach. Nestled in Westport's prestigious Greens Farms enclave, this Victorian estate blends timeless character with modern sophistication. Originally built in 1861 and expanded in 2008, it offers over 6,600 sq ft of refined living space on 2.02 serene acres. Enjoy lush lawns, a private pool, outdoor kitchen, and hot tub-perfect for relaxing, entertaining, or quiet reflection. Inside, historic charm meets modern comfort with original fireplaces, soaring ceilings, and exquisite millwork. The gourmet kitchen, anchored by a large island, opens to an expansive great room and includes a butler's pantry with a walk-in commercial refrigerator. The lower level features arched doorways, natural light, and flexible space for a gym, playroom, office, or guest suite. A luxurious bar and theater-style entertainment area with mahogany tray ceilings adds sophistication, while a rooftop balcony makes every evening special. A six-car garage plus rear access for two more vehicles ensures convenience. Just minutes to Metro-North, I-95, beaches, and Westport's amazing restaurants and shops, this home offers the perfect blend of New England charm and modern luxury-all with NYC within easy reach.

342 Greens Farms Rd, Westport
4 Wake Robin Rd, Westport
$2,048,000
5 Beds ⋅ 4 Baths ⋅ 24172491 MLS
Peacefully placed overlooking Signal Lake on a Greens Farms cul-de-sac is 4 Wake Robin Road, a classic Colonial with so much to offer! With over an acre of flat, private and blooming property, the home sits far back from the road with wooded and water views. Filled with historic charm, the main floor is bright and sunny - there are formal living and dining rooms with built-ins and cozy decorative fireplaces. The large family room has plenty of space for gathering and lounging, and connects to the beautiful screened in porch, perfect for 3 season enjoyment. The kitchen is anchored by a large island with cooktop, there are double wall ovens and a dining area. An office and powder room complete the main floor. Upstairs holds the primary suite, another ensuite bedroom, two bedrooms and a flexible bedroom/office space that share a hall bath as well as the laundry room. There is also a walk up attic space for plenty of storage. A pretty brick patio spans the front of the home with views of the rolling lawn, while there is a lush green backyard with access to the lake for a canoe rise or paddle board! There is a two car garage, and double driveway areas for sports and guest parking. Conveniently located to town, schools, the Greens Farms train station, and of course, Westport beaches!

4 Wake Robin Rd, Westport
7 Morningside Ln, Westport
$1,751,000
4 Beds ⋅ 2 Baths ⋅ 24103327 MLS
A Westport treasure, this c.1900 beauty enchants with timeless charm and a magical warmth. Once the homestead of one of Westport's largest onion farms, you may still find one growing wild on the lawn. The wrap-around screened porch is perfect for summer mornings or unwinding at sunset. Inside, sunlit living spaces are filled with original character, and the chef's kitchen offers high-end appliances, wine fridge, and a breakfast nook set in a bank of windows. Listed on Westport's historic inventory (but not registry-restricted), the home offers flexibility for expansion or renovation. Outside, enjoy a large, level double lot on a peaceful cul-de-sac-ideal for lawn games, gardening, or a pool. The detached garage does not currently have living space above, but there's ample room to expand or add a guest cottage, office, or gym. Bordered by stone walls, and just minutes from the beach, train, and town-this is a rare chance to own a piece of Westport history.

7 Morningside Ln, Westport
8 Iris Ln, Westport
$1,630,000
4 Beds ⋅ 3 Baths ⋅ 24154436 MLS
HIGHEST & BEST BID DEADLINE: 6:00 pm Sunday, March 1st. Sun-drenched, stylish and inviting 4 Bed, 3 Full Bath home on .7 acres on a quiet cul-de-sac located in the coveted Greens Farms neighborhood, walkable to grocery, restaurants, shops, schools. Gleaming hardwood floors throughout add warmth and character. Spacious front living room with a show-stopping fireplace connects to cheery dining room. Great entertaining flow with an open concept kitchen and adjoining family room - both with French doors onto a large stone patio overlooking the lush, pretty backyard. New kitchen cabinets plus island, double ovens, two sinks, bar stool counter. Over $216K in recent upgrades: New Roof, Hardie Board siding, Central AC, Whole House Generator, Oil Tank, Cedar Fencing, Tree Landscaping. Flexible floor plan: two Primary options: First-Floor Primary with new en-suite bath or Upper-level with wrap-around balcony and two closets, one walk-in. Luxurious second floor full hallway bath with radiant heat floors, double sink quartz vanity, plenty of storage. Oversized two-car garage, fully-finished walk-out basement with mudroom/laundry, gym, rec room. Fully-fenced backyard with flat areas for playsets/sports. Stellar curb appeal w/stone retaining walls, steps, Belgian Block lined driveway and commanding presence on its elevated "Builder's Prime Lot" at the end of the cul-de-sac - no thru traffic. Peaceful, private property near Metro North, schools, shops - all in fabulous Westport,

8 Iris Ln, Westport

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