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William Pitt Sotheby's International Realty

696 Boston Post Road, 06443 Madison (United States)

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Listings for sale: 1 to 20 / 36

  • 33

    Property Madison (United States)

    If you've ever strolled down East Wharf, you've likely noticed this charming home. Just a few houses from the beach, this thoughtfully renovated 3 bedroom, 2.5 bath gem blends timeless coastal Connecticut style with custom craftsmanship and modern convenience. The curb appeal is undeniable, with a pristinely manicured yard, paver driveway and Belgian block apron. Inside, the living room features a teak ceiling, stone fireplace and designer lighting, flowing seamlessly into the dining area with custom built-in cabinetry. The reimagined kitchen showcases fluted mahogany cabinetry, high-end appliances, box beam ceilings, designer lighting and expansive new windows. Sliding doors open to a beautifully landscaped backyard with an oversized cedar outdoor shower, large patio and private seating area. A heated detached garage with electricity offers flexible space for a studio, office, gym, entertaining area, guest overflow or storage. Upstairs are three bedrooms and two full baths, including the Primary with custom built-ins, double closets and a renovated bath. The 2nd bedroom features a custom built-in bed with integrated storage, while the 3rd bedroom is currently used as an office. There is also an attractive full guest bath. Extensively updated and professionally designed throughout, this turnkey home is within walking distance to the beach, shops, restaurants, and everything this beloved shoreline town has to offer. See attached list of improvements. They are impressive!

    … 
    $1,325,000
    3bedrooms
    3bathrooms
    land 486

    By William Pitt Sotheby's International Realty

  • 37
    Video

    House Madison (United States)

    Set back from Middle Beach Rd and sited 25' above sea level (so no flood insurance needed!) with deeded beach rights and views of Long Island Sound is a like-new (completed in 2023) charming 4 bedroom, Cape Cod style home on an unusually large 1.12 acre lot. The open plan's first floor has a cathedral ceiling in the living room with a gas-lit stone fireplace, a dining area, and a fully equipped eat-in kitchen adjacent to a mud room leading to the attached garage. The first floor primary bedroom has a large bathroom and an enormous walk-in closet, the object of many dreams. A den/office and a powder room complete the first floor. The second floor has three spacious bedrooms, a family bathroom and a large room currently used as an art studio but could be a large bright bedroom. There are two porches - one overlooks the water and the other, the back yard. A full, unfinished basement and unfinished space above the garage also offer endless possibilities. Access this special property via Pheasant Drive.

    … 
    $2,495,000
    4bedrooms
    3bathrooms
    land 4,532

    By William Pitt Sotheby's International Realty

  • 37
    Video

    Property with pool Essex (United States)

    Two hours from New York City. Two hours from Boston. A world away from both. Privacy is the ultimate luxury. This masterfully re-imagined 5,234 sq. ft. compound located in historic Ivoryton, a village within the town of Essex, sits behind newly established hedges on nearly two flat, manicured acres - completely turn-key, completely private. The grounds are designed for outdoor living. A 20 X 40 gunite pool flows into a hydrangea-framed landscape. Three bluestone patios for entertaining, dining, and quiet retreat. A newly built two-car garage, wired with new electrical and EV charger-ready. Inside, the transformation is total. A chef's kitchen built around a custom black cherry island with Sub-Zero refrigerator, new double wall oven, and cooktop. A butler's pantry adds a second refrigerator and dedicated wine fridge. Four bedrooms with private en suite bathrooms, including a reimagined primary suite with spa-level finishes. Two home offices. And the sunroom - a fully restored 1920s porch with original terra cotta floors and sweeping estate views. Every room is professionally curated with bespoke wallcoverings and custom light fixtures. Steps from the Ivoryton Playhouse, The Copper Beech, and Prive Swiss. Minutes to Connecticut River marinas. Long Island Sound 15 minutes beyond. A truly unique property located in what Yankee Magazine ranks as the #1 small town in New England.

    … 
    $2,600,000
    5bedrooms
    6bathrooms
    land 7,527

    By William Pitt Sotheby's International Realty

  • 39

    Property Madison (United States)

    The historic c. 1904 Scranton Homestead, described as a Colonial Revival gem, has come to the market! This much admired 3700 sf in town landmark offers an estate feel on a large, beautifully landscaped lot providing both privacy and convenience, moments from the village center and East Wharf Beach. With four bedrooms, this residence borrows from classic forms, with window styles, columns and porches found only in the most important homes of the era. Hand-worked trim, coffered ceilings, and detailed fireplaces speak to the craftsmanship available at the turn of the last century. Assets include a fully private primary suite with fireplace and custom dressing room, a third floor multi use space ready for special guests or activities. A well balanced blend of preserved history and modern comfort, the centerpiece of the home is an expansive fully updated chef's kitchen open to a great room with a cathedral, beamed ceiling and a wall of oversized glass bringing in light and showcasing the gardens, stone walls and patio features.

    … 
    $2,295,000
    4bedrooms
    4bathrooms
    land 2,630

    By William Pitt Sotheby's International Realty

  • 19

    Property with garden Madison (United States)

    32 North Street is calling you home! Set on one of the largest lots in Dud's Village, this lovely cottage is the idyllic seasonal abode. Equipped with 2 bedrooms, 1 full bath, and an outdoor shower, you will surely enjoy your summers along the Madison shoreline here. The recently refreshed kitchen and fresh coat of paint throughout will undoubtedly delight. And let's not forget the new floors in the kitchen and living room. The enclosed front porch is simply charming offering additional living space and featuring daybeds for cool summer sleepovers. Outside is an entertainer's paradise - a desirable corner lot with the oversized deck and enough yard space to host all your family and friends. Just a short distance to Salt Meadow Park, Hammonasset Beach State Park and downtown Madison, you'll always have something to do! And with summer right around the corner, you'll want to move quickly! Schedule your tour today and fully embrace coastal living at its finest! The village is seasonal - April 1st through October 31st. Land is leased by cottage owners, and the land lease is currently $5,400 per year.

    … 
    $164,900
    2bedrooms
    1bathroom
    land 202

    By William Pitt Sotheby's International Realty

  • 34

    Property with pool and garden Madison (United States)

    Welcome to 238 Scotland Road, a rare 5-bedroom home with private in-law accommodations, pool, situated on nearly an acre of privacy. A lovingly cared-for home offering exceptional space, comfort, and versatility. Features include hardwood floors throughout, central air conditioning, and a beautiful new primary suite designed for relaxation and convenience. The heart of the home is the updated kitchen, thoughtfully renovated and perfect for everyday living or entertaining. Just beyond, a bright and inviting sunroom provides the ideal place to unwind year-round and opens onto a Trex deck to the backyard and pool. Cozy up on cooler evenings beside the charming wood-burning stove, creating the perfect setting for relaxing nights at home. Step outside to enjoy the private inground vinyl-lined pool with a newer liner, offering endless opportunities for summer fun, entertaining, and making lasting memories with family and friends. Adding incredible flexibility, the property includes an attached in-law apartment with its own separate entrance and full bath, making it ideal for extended family, guests, or multi-generational living. Additional highlights include a newer roof, public water, generous living spaces, and a peaceful setting that feels secluded while remaining just minutes from town, beaches, shopping and dining. This well-loved home offers the perfect combination of privacy, thoughtful updates, and room to grow-ready for its next chapter.

    … 
    $775,000
    5bedrooms
    4bathrooms
    land 3,925

    By William Pitt Sotheby's International Realty

  • Contract pending
    40

    House with pool Madison (United States)

    Rare opportunity to own in one of Madison's most coveted shoreline locations. Just steps from East Wharf Beach and a short stroll to downtown Madison's shops, acclaimed restaurants, and vibrant village center, this 3-bedroom, 2-full-bath residence captures the essence of Connecticut coastal living. Privately sited on a beautifully maintained lot with an in-ground pool, the property offers a rare combination of beachside convenience and backyard seclusion. The outdoor spaces invite relaxation and entertaining, while a detached 2-car garage provides additional flexibility for storage and more. Inside, the home is filled with warmth and character. The main level features a lovely sun/sitting room, a dining room designed for gathering, and a cozy living room anchored by a fireplace. The bespoke kitchen showcases charming built-in pine features that reflect the home's timeless appeal. A tucked-away doorway off the living room reveals a finished lower level currently enjoyed as a den and media room-an unexpected and inviting extension of the living space. Can be enjoyed as a year-round residence, seasonal escape, or thoughtfully reimagined coastal retreat with exceptional location, timeless character, and tremendous potential! Wake to the scent of salt air, spend your days at the beach, stroll into town for dinner, and return to the privacy of your own backyard oasis. A truly special offering in one of Madison's most sought-after coastal settings!

    … 
    $1,300,000
    3bedrooms
    2bathrooms
    land 2,145

    By William Pitt Sotheby's International Realty

  • 29

    House Clinton (United States)

    Coastal living meets worry-free luxury in this completely remodeled, turn-key masterpiece! Absolutely everything is brand new, offering the peace of mind you deserve with a new roof, energy-efficient windows, and a top-tier heating and cooling system. The heart of the home features a stunning, fully redesigned gourmet kitchen and flawlessly updated bathrooms with modern finishes. Nestled in a highly desirable location, this property grants exclusive access to a coveted private beach-perfect for sun-soaked days and evening strolls. Boat enthusiasts and foodies alike will love the close proximity to local marinas and the vibrant town center. Do not miss this rare opportunity to own a brand-new home in an unbeatable location!

    … 
    $950,000
    3bedrooms
    2bathrooms
    land 1,659

    By William Pitt Sotheby's International Realty

  • 31

    Property Haddam (United States)

    Amazing colonial on over 2 acres in the lovely country setting of Haddam. The 2-stall stable (interior walls are down) with water and electric on a level large lot, offers the opportunity for horses or other livestock. Some of the wonderful features of this home include~ First floor primary bedroom suite, large eat in country kitchen with stainless steel appliances, fireplace with insert in family room. Beautiful hardwood through-out on first floor, central vac, and generator with hook-up. The bedrooms are wonderfully large and most have walk in closets. The room over the garage (unfinished) can add so much space if desired. Enjoy the huge walk out basement perfect for storage or finishing. Great back deck overlooking level private back yard. Cool exterior lighting and large fire pit adds so much! This house is a feel good house that you must see.

    … 
    $689,000
    4bedrooms
    3bathrooms
    land 8,417

    By William Pitt Sotheby's International Realty

  • 35

    Property Deep River (United States)

    Quintessential New England living in the heart of Deep River. This exceptional Antique home was masterfully expanded in 1987, seamlessly doubling its size while capturing the essence of a classic Colonial-offering the space, flow, and functionality for today's living. The home's design celebrates period-inspired architecture including custom-milled woodwork, wide-plank pumpkin pine floors, and carefully selected reproduction details creating warmth and authenticity. Multiple living and dining spaces unfold effortlessly, anchored by six fireplaces, including an impressive 12' natural stone Rumford. With seven spacious bedrooms-each with its own private bath-the home is uniquely suited for multi-generational living, hosting, or continued hospitality use. The third-floor suite offers a private retreat with a wood-burning fireplace, perfect for extended family or guests. A new kitchen addition further enhances flexibility, easily accommodating in-law living or private guest quarters. Curated perennial gardens, a white oak pergola, and a beautifully crafted stone terrace create a setting designed for gathering and relaxation. Enjoy evenings by the fire pit, surrounded by timeless landscape design. This property offers style, comfort and charm all amidst the local shops, restaurants, marinas, and nearby shoreline destinations-all within two hours of both NY and Boston. Previously, an Award-Winning Bed & Breakfast, and currently featuring two Airbnb guest suites with private access.

    … 
    $1,199,999
    9bedrooms
    9bathrooms
    land 1,821

    By William Pitt Sotheby's International Realty

  • Contract pending
    30

    House Madison (United States)

    A rare offering in one of Madison's coveted shoreline neighborhoods, this custom-built Cape has been impeccably preserved since 1972, presenting a remarkable opportunity to own a home of enduring quality, character, and potential. Set on a private 1.02 acre lot with an Island address and easy access off Cambridge, the location offers exceptional privacy while remaining a quick walk to town, the Green or the beach. This charming 4 bed, 3 full bath home features 3,046 square feet of living space. Gracious formal rooms include an elegant living room with original hardwood floors (ready for refinishing as the shag rugs were just removed!) and sliders to a terrace. You'll also enjoy a bespoke dining room with a custom-painted island inspired wall, and a handsome wood-paneled family room with a fireplace and access to the 2 car garage. The large sunroom overlooks the beautiful grounds, while the charming, functional kitchen includes a casual eating area. A thoughtful floor plan offers two bedrooms and two full baths on the main level that could easily be combined to create an impressive 1st floor primary suite. Upstairs, a spacious landing leads to a large bath with double sinks, a generous guest bedroom, and an enormous fourth bedroom ideal as another bedroom suite, office, studio, recreation space or combination depending on your needs. Dated yet in exceptional condition, this rare gem offers location, privacy, scale, and endless possibilities. Request for All Offers 6/7 at 6pm.

    … 
    $1,400,000
    4bedrooms
    3bathrooms
    land 4,128

    By William Pitt Sotheby's International Realty

  • 36

    Farmhouse Guilford (United States)

    Welcome to Waystone Farm, an award-winning, energy-efficient gentleman's farm and potential horse property. Proud winner of the 2016 Highly Insulated Passive House Standard Award, this estate masterfully blends sustainability with luxury living.The main residence features newly refinished hardwood floors and a bright, open floor plan. A sun-filled great room flows into the chef's kitchen, complete with quartz counters, a large island, Thermador appliances, and induction cooktop. Designed for one-level living, the spacious primary suite is located on the first floor. In total, the home offers four bedrooms, three full, and one half bath. Amenities include a dedicated mudroom and laundry room equipped with an advanced ozone laundry system. Built to the highest green standards, the home utilizes geothermal heating and cooling, active solar, and energy efficient triple-pane windows. A full unfinished basement holds a large root cellar, while the three-car garage boasts an EV charging station and a walk-up attic storage area. A Generac generator ensures total peace of mind. Relax on one of the two Ipe covered front porches and take in the stunning grounds. This unique property features a passive solar greenhouse with cold frames, extensive garden bedding, a newly planted fruiting tree orchard, and sugar maples. Animal lovers will find a three-stall barn, two chicken coops, a duck coop, an enclosed dog park, and two large fenced pastures with hay fields.

    … 
    $1,825,000
    4bedrooms
    4bathrooms
    land 3.3ha

    By William Pitt Sotheby's International Realty

  • Contract pending
    21

    House Hamden (United States)

    Welcome to this charming 3-bedroom, 1.5-bath ranch-a cherished family home lovingly maintained for more than 50 years. The beautifully remodeled eat-in kitchen features abundant cabinetry, granite countertops, and tranquil views of the serene backyard. Step outside to a spacious, low-maintenance composite deck overlooking a picturesque yard, where a gentle brook winds through the property. The woods beyond the brook offer peaceful areas to explore, all watched over by a stately 275-year-old white oak-honored as Hamden's 2006 Tree of the Year! Inside, the cozy living room offers a woodburning fireplace and hardwood floors that extend throughout the main level. Three comfortable bedrooms, 1.5 baths, and a convenient hallway laundry area complete the first floor. The bright, finished lower level provides generous additional living space with ample natural light-perfect for a family room, home office, or recreation area. Additional highlights include a detached 2-car garage, central air, a whole-house generator, and a new boiler. Warm, welcoming, and truly move-in ready, this home is waiting for a new family to enjoy it for more years to come!

    … 
    $369,000
    3bedrooms
    2bathrooms
    land 3,318

    By William Pitt Sotheby's International Realty

  • 27

    House East Haven (United States)

    Welcome to 3 Carmen Street, a beautifully remodeled two-family home offering a total of 5 bedrooms and 3 baths-an ideal opportunity for investors or extended families seeking flexible living space. Both units have been thoughtfully updated with new kitchen cabinets, granite countertops, and modern appliances. All former tile flooring has been removed and replaced with gleaming hardwood floors, and two of the three bathrooms have been tastefully renovated. The home also features two new oil tanks and updated electrical panels for added peace of mind. A two-car attached garage, plus space for four additional cars in the driveway and off-street parking, ensures plenty of room for residents and guests. A convenient door near the driveway leads into a breezeway connecting both floors, as well as an enclosed porch that opens to the beautiful fenced-in backyard with a patio overlooking a serene brook-often visited by a family of mallards. Located in a prime, convenient area close to beaches, parks, shopping, restaurants, highways, and transportation, this property blends comfort, practicality, and charm in one inviting package.

    … 
    $499,000
    5bedrooms
    3bathrooms
    land 890

    By William Pitt Sotheby's International Realty

  • Contract pending
    22

    Farmhouse Guilford (United States)

    Welcome to 31 River Colony, a cozy and inviting first-floor ranch-style condo with one bedroom, one bath, and beautiful natural surroundings. The open layout includes an updated galley kitchen with granite counters, plenty of storage, and a pantry/utility closet-plus the added convenience of in-unit laundry, a rare feature in the complex. The dining and living room flow together seamlessly, anchored by a woodburning fireplace perfect for chilly evenings. Step through the large sliders to your private deck, where you can unwind while taking in tranquil views of the West River and its surrounding wildlife. The spacious bedroom connects to a fully updated bath featuring a stylishly designed walk-in shower. Quiet, private, and well cared for, this condo offers low HOA and an unbeatable location close to shopping, dining, and major highways.

    … 
    $259,000
    1bedroom
    1bathroom

    By William Pitt Sotheby's International Realty

  • Contract pending
    28

    House Guilford (United States)

    Welcome to this beautifully maintained 3-bedroom, 2-bath home designed for easy one-level living. Perfectly situated across from a scenic open field once used as a farm, this property offers a peaceful setting while still being within walking distance to town. A recently completed addition expands the home by nearly 500 square feet, creating a stunning living space with cathedral ceilings, a gorgeous gas log fireplace, and walls of windows that flood the room with natural light. It's the perfect spot to relax and enjoy cozy evenings by the fire while taking in views of the expansive, nearly 1-acre fenced yard filled with mature trees and vibrant flowers. Inside, the home features an open floor plan with built-in storage throughout, offering both functionality and charm. The layout creates a warm, inviting atmosphere that feels cozy without ever feeling cramped. . The modern kitchen is both stylish and functional, featuring a large island with granite and quartz countertops-perfect for meal prep, casual dining, or entertaining. A chef-inspired dual fuel 5-burner stove anchors the space, offering the performance and versatility today's home cooks appreciate. The home features a new roof, a new AC system and a motor-driven wood fireplace which is excellent on utilities and definitely move-in ready. Whether you're an empty nester looking to simplify or a small family just starting out, this home offers the perfect balance of comfort, space, and location.

    … 
    $779,000
    3bedrooms
    2bathrooms
    land 3,683

    By William Pitt Sotheby's International Realty

  • 25

    House Madison (United States)

    LOCATION ~ LOCATION ~ It matters !! Situated in the Coastal Charm of Madison, this Seasonal Cottage is your Escape you can plan on Every Summer !! Enjoy all that Madison has to offer w/ Concert's on the Green, Farmers Markets, Restaurants and Beaches. It's a Long Summer too ~ Residence can stay from April 1st all the way through October 31st., a Full 7-Months. Home is perfectly set at the End of East Street (minimal traffic) on an Oversized, Level Lot.

    … 
    $200,000
    2bedrooms
    1bathroom
    land 405

    By William Pitt Sotheby's International Realty

  • Contract pending
    33

    Property Madison (United States)

    NEW PRICE BELOW RECENT APPRAISAL. One house from L.I. Sound on a quiet Webster Point Road cul-de-sac, this 4000+ sf house delivers the ideal shoreline life: deeded beach access, multi-level panoramic water views, walkable distance to the Hammonasset Trail, and a spacious interior perfect for both large gatherings & cozy family life. A double-height foyer opens the house and leads into light-filled rooms with 10' ceilings & hardwood floors throughout the 1st level. The expansive LR is anchored by a handsome wood-burning FP and flows to a formal DR featuring intricate millwork from a historic mansion. The same heirloom millwork frames the dining area of the kitchen, which is fully-equipped to inspire the modern gourmet. The kitchen has access to a large porch perfect for summer entertaining & connects to a heated 2-car garage. Upstairs, the home offers a rare configuration: 2 primary suites - one on the 2nd floor, one on the 3rd - each with private decks to enjoy the water views that are unparalleled for area houses not directly waterfront. Two additional bedrooms on the 2nd floor share a hall bath & laundry room. The 3rd floor includes a finished den/office & storage. Deeded access to a low-tide beach and the sandy Pent Road beach offer endless opportunities to watch the sun rise or set, relax in the salty breeze, sea-fish, or take the canoe out. The bike-and-walking trail to Hammonasset State Park is at road's end.

    … 
    $2,195,000
    4bedrooms
    4bathrooms
    land 1,376

    By William Pitt Sotheby's International Realty

  • 43
    Video

    House Madison (United States)

    Own an architectural masterpiece with waterviews! Rarely is a Robert Page (AIA) designed coastal home available and this is one of his most compelling. A collaboration with master builders Baldwin and Baldwin and executed with precision, this 3300 sf home with three exterior decks, (including a Skydeck), unfolds over four levels. Finished in 2010, this 3(+) bedroom, 3.1 bath gem offers 3300 lifestyle driven sf unlike any other beach area home you have ever seen. A true study in material, light and craftsmanship and just three homes from the Sound, w/rights to coveted Hartford Avenue Beach. Landscape designer Gordon Hayward shaped the exterior as an extension of the architecture with a rectilinear goldfish pond and a circular fountain for counterpoint. The open design allows the light to play all day on the rich Douglas fir vertical grain paneling throughout. The house tells the story of how much effort this took- everywhere you look, extensive custom hand-built cabinetry, bookshelves and cubbies. Anne Sacks provided the tile, granite, marble and soapstone countertops. Everything is premium and a very thoughtful choice-Noguchi Acari pendant lighting, McIntosh whole house sound system, Bosch, Dacor, Asko and Subzero appliances. 24 owned solar panels for energy, two custom lifts- one in the stairwell serves as dumbwaiter for all four levels and the exterior lift brings firewood to the second floor veranda.This property must be experienced in person to be fully appreciated

    … 
    $2,295,000
    3bedrooms
    4bathrooms
    land 526

    By William Pitt Sotheby's International Realty

  • Contract pending
    35

    House Madison (United States)

    Discover a hidden treasure in one of Madison's finest neighborhoods, featuring vintage bungalow charm. A bright and welcoming sun room, enhanced with baseboard heating, offers a serene space to relax in every season. The main floor includes a large combined living and dining room with stunning wood floors and a wood burning fireplace. Off of the bright and functional kitchen you will find a full bath, while the second floor houses a half bath alongside the bedrooms. The large unfinished basement is a real bonus and remarkably dry. An adorable seasonal guest cottage offers garage and storage options, complemented by lovely views of the salt meadow. This is the perfect spot to build lifelong memories. With two outdoor showers to rinse the sand off, great off street parking, sweet backyard between dwellings, and just 550 steps to the most beautiful beach in town, you can expect visitors. This property holds great promise for its next owner-explore the possibilities!

    … 
    $775,000
    2bedrooms
    2bathrooms
    land 688

    By William Pitt Sotheby's International Realty

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