luxury house with pool for sale Brewster, United States

Elegance, scale, and solitude define this exceptional home. Set behind a sweeping circular drive accented with custom pavers, this sprawling 4-bedroom, 3.5-bath residence seamlessly pairs refined craftsmanship with a resort-inspired outdoor sanctuary. Step into the center-hall foyer, flanked by formal living and dining rooms that showcase beautiful wide-plank hardwood floors and picturesque seasonal views. The heart of the home is the spectacular Great Room, highlighted by vaulted ceilings, exposed beams, a majestic center fireplace, and direct deck access for effortless indoor-outdoor entertaining. The expansive kitchen offers granite countertops, generous cabinetry& tile flooring with convenient access to the laundry room and garage. Just off the kitchen, a charming breakfast room set within a sunlit turret awaits, complete with an electric fireplace, vaulted ceilings, and its own deck entrance. The luxury main-level Primary Suite serves as a private retreat, offering a walk-in closet and a spa-like en-suite bath with an oversized glass shower, Bain Ultra Spa tub. Step from the bedroom onto a private deck with immediate access down to the gardens, patio, and pool. Upstairs, the balcony leads to a quiet reading space, leading to generously sized bedrooms with ample storage and dedicated baths-including a Jack-and-Jill layout-all enjoying lovely views. Outside, the grounds offer custom Gunite pool and spa, gazebo, private decks and patio. This beloved home is exceptional

Welcome to 145 Pine Hill Rd. A renovated Organic Modern home mixing both modern amenities and rustic charm. Adorned with random plank flooring, hand-hewn beams and massive field stone fireplace. The 12ft sliders in the Living Room allow for access onto the spacious deck. The culinary space is a chef's haven, equipped with state-of-the-art appliances & premium finishes that inspire culinary creativity. With southern exposure, the house offers plenty of opportunities for sunlight, expansive views off the deck along with a great setting for gardening. Each of the 4 bedrooms provides a unique space, while the 4 baths feature refined fixtures & chic designs, ensuring every personal convenience is met. Off the primary bedroom is a retreat unto itself, featuring a circular patio where one can reflect in the joyful sounds of the water fountain or unwind in the private hot-tub. The lower level is another entertainment area with full bathroom and spacious family room with wet-bar which opens to the swimming pool and deck areas. Great for the avid outdoor enthusiast where there is plenty of hiking, mountain biking and fishing.

Welcome to 145 Pine Hill Rd! An exquisite home offering 4-bedrooms with 3.5 baths and a generous 3400+/- total sf. Home is set on a spacious 4.57 -acre lot and features an oversized 4 car-detached garage. As you approach the property, you'll be greeted by a front porch, welcoming you inside. The heart of the home is adorned w/reclaimed, hand-hewn beams accentuating the ceilings & mantle, paired harmoniously with a propane log fireplace. This central gathering space is bathed in natural light spilling in through expansive windows, complemented by a twelve-foot wide Anderson double slider leading to a meticulously crafted deck, optimizing the western exposure for all day sun. The kitchen offers a state-of-the-art appliances and extensive countertop space with over 20 feet on the perimeter and an 11 ft island. Each of the 4 bedrooms provides a unique space, while the 3.5 baths feature refined fixtures & chic designs. Off the primary bedroom is a retreat unto itself, featuring a circular patio where one can reflect in the joyful sounds of the water fountain or unwind in the private hot-tub. The lower-level family room with a built-in bar and a cozy wood-burning stove, ideal for entertaining & relaxation alike. A saltwater in-ground heated pool & beautifully crafted outdoor entertainment areas, including a whimsical chicken coop/shed, enrich the outdoor living experience. Nestled near captivating attractions such as Pootatuck State Forest & Candlewood Lake.

Ideally situated on a quiet cul-de-sac of similar fine homes, this beautifully renovated four-bedroom Colonial offers an exceptional location just minutes from the Brookfield town line and the Candlewood Lake Lattins Cove Boat Launch, providing easy access to lake activities, shopping, dining, and commuting routes. Convenient to I-84, this home combines a peaceful neighborhood setting with everyday accessibility. Inside, the home blends classic Colonial design with extensive modern updates, including a brand-new roof (June 2025). The main level features new porcelain tile flooring in the entry, an upgraded kitchen with high-end appliances, and a newly renovated powder room appointed with premium Kohler fixtures, a Milano vanity, and an electric mirror. Fresh crown molding enhances the living and dining rooms, while a striking new chandelier welcomes guests in the foyer. Recessed lighting brightens the family and living areas, and hardwood floors extend throughout all bedrooms. The walk-out finished basement provides additional living space with fresh paint and quality laminate flooring. Outdoors, the oversized saltwater pool serves as the focal point for entertaining and relaxation, complete with an automatic cover and attractive new stone wall surround. A stone walkway from the street adds to the home's curb appeal. Additional features include a spacious attic, two-car garage, wiring for an interlock generator, and numerous thoughtful upgrades throughout. Owner/Agent.

Timeless charm meets modern comfort on prestigious Deer Hill Avenue. Welcome to this beautifully updated antique home, where period character and modern elegance come together effortlessly. Meticulously maintained for the past 10 years, the home features a new roof and boiler, ensuring peace of mind for years to come. A welcoming, expansive front porch with a swing and new flooring sets an inviting tone as you step inside to a beautifully appointed interior with hardwood floors and classic architectural details. The light-filled living room boasts a gas fireplace, while an elegant formal dining room sits just across the hall—ideal for hosting memorable gatherings. At the heart of the home, the updated kitchen features quartzite countertops, new appliances, and a fabulous walk-in pantry outfitted with glass-front cabinetry. Up the grand staircase, you will find four spacious bedrooms, including three generously sized rooms and a flexible fourth room perfect for a primary closet, dressing room, or quiet study. The partially finished lower level provides versatile extra space for a home gym or office, along with convenient access to the attached one-car garage. Outside, your private backyard retreat awaits! Two-tiered decking surrounds the above-ground pool and hot tub, complemented by a lower patio for additional outdoor entertaining. Adding even more versatility, the detached two-car garage features a finished room above with a separate entrance—ideal for a private home office, creative studio, or dedicated hobby space. Come discover the unmatched appeal of 65 Deer Hill Avenue.

If a beautiful home with a backyard oasis is high on your priority list, this property delivers both. Inside, hardwood floors run throughout much of the main level, including the bright and spacious living room with a shiplap accent wall that adds just the right amount of character. The kitchen offers plenty of cabinetry and counter space, along with a casual dining area for everyday meals, while the adjoining formal dining room provides additional space for entertaining and gatherings. The home features four bedrooms and two beautifully designed full baths. The lower level adds an impressive amount of additional living space, with a large family room centered around a stone fireplace, a charming built-in seating nook, a home office, and an additional room that works perfectly as a bedroom, playroom, gym, or whatever suits your lifestyle. The expansive, level yard offers plenty of room for games, gatherings, pets, or simply enjoying the outdoors. A spacious Trex deck surrounds the above-ground pool, creating a great place to spend summer afternoons and evenings with family and friends. A separate patio and fire pit area adds yet another outdoor space to relax and entertain. Conveniently located in Brookfield with easy access to schools, shopping, restaurants, and I-84.

Nestled along the serene shores of Candlewood Lake, this exceptional waterfront property-complete with 0.74 acre of land-offers a rare opportunity for lake lovers to experience the ultimate retreat. The custom-built main home features 3 bedrooms/office and nearly 2,800 square feet of sophisticated living space, highlighting exquisite craftsmanship and attention to detail. Enjoy breathtaking western-facing lake views from the expansive cathedral-ceiling living room, enhanced by a stone fireplace. The spacious great room, also featuring another stone fireplace, along with the peaceful three-season conservatory, provide the perfect setting to relax and soak in the surrounding beauty. A spacious flagstone patio outside also offers ample room to unwind while taking in the gorgeous waterfront. With over 200 feet of coveted direct waterfront, a private dock, and a cantilever, this property delivers unrivaled access to the water. A true value-add is the 858-square-foot lakefront cottage, complete with a three-car garage, panoramic water views, a full bath, kitchen, and a large wood deck-an ideal space to gaze out on stunning lake views. This is an amazing opportunity to own a truly remarkable waterfront sanctuary.

31 Deer Run Road in Brookfield, CT is a raised ranch home set on a level acre framed by mature trees, offering year-round indoor and outdoor living space. The main level features hardwood floors, a light-filled living room, and a formal dining room detailed with decorative wainscoting. Adjacent to the dining space, the eat-in kitchen offers white cabinetry, a vaulted ceiling, and direct access to the rear deck overlooking the yard. The primary bedroom and two additional bedrooms are conveniently situated on the main level. Both the primary bath and the full hall bath feature heated floors for added comfort. The lower level expands the living space with a spacious family room anchored by a classic brick fireplace, a dedicated office area, and sliding glass doors that open to the backyard. Outside, a fully fenced in-ground pool surrounded by a paver patio serves as a primary outdoor gathering spot, complemented by a raised deck and covered patio. Additional features include a 22kW whole-house generator, along with convenient access to Candlewood Lake, local shopping, dining, and major commuter routes.

This gracious country estate's idyllic setting is the perfect backdrop for large family gatherings and joyous celebrations. For over 40 years, the Rosenthal family has cherished this sprawling sanctuary, creating a legacy of warmth and hospitality that is unmatched. Now the doors are open for a new owner to create timeless memories - whether poolside; sitting by the outdoor fireplace; cooking in the al fresco kitchen; or retreating inside this home's exquisitely refined living spaces. Designed with unwavering attention to detail, this home's sophisticated interior is a testament to timeless elegance, and features six bedrooms, six full and two half baths. Each space has been thoughtfully appointed to accommodate both large-scale events & intimate family moments. The heart of this one of a kind home is not just one, but THREE kitchens - the primary family kitchen, a full-scale catering kitchen, plus the outdoor kitchen. With elegant formal living and dining rooms, plus grand family room complete with full bar, this unique property is always ready for entertaining. Step outside to the most enchanting outdoor oasis showcasing the free form gunite pool with expansive brick terrace, plus full pool bath. The crowning jewel of the property is a magnificent 30' x 40' slate patio, complete with an event tent. Whether it's intimate soirees or grand formal events, this space is perfectly sited to capture panoramic vistas of the property's mature flowering trees, stone walls, and perennial gardens.

Set across 53 gated acres in Northern Fairfield County, this exceptional estate offers a rare combination of privacy, scale, and natural beauty, just minutes from Ridgefield, approximately ten minutes from Danbury Airport, and within practical reach of New York City. Originally conceived as a country retreat, the property blends historic character with modern comfort in a setting that feels private and serene, yet fully suited to year-round living. Beyond the gates, the grounds unfold across woodland trails, a stone bridge, pond, brook, orchards, gardens, and approximately two miles of groomed paths through the estate's own natural preserve. The landscape has been carefully maintained and offers both beauty and utility, with room for recreation, agriculture, and future enhancements. The residence is rich in character and thoughtfully updated, with six fireplaces, a double-sided chef's kitchen, wine cellar, and a 1,055 SF primary suite with dual baths, dressing room, walk-in closet, private sitting room, and sunroom. Outdoor living is centered around a heated gunite pool, outdoor kitchen, pergola, and gazebo, all positioned to take in sweeping views of the surrounding landscape. A detached barn, detached garage, and expansive acreage create unusual flexibility for equestrian pursuits, agriculture, a guest house, tennis or paddle court, and other future improvements, subject to local approvals.

Tucked away at the end of a quiet cul-de-sac, this oversized raised ranch offers privacy, space, and comfort! Lovingly maintained by the same owner for 43 years, this home features new quartz countertops, Andersen replacement windows, and updated bathrooms. The finished lower level offers a cozy wood-burning fireplace, fourth bedroom, and bathroom with a Jacuzzi tub, providing great potential for an in-law arrangement or extended guest space. A spacious mudroom off the garage adds everyday convenience. Step outside to your own private backyard retreat featuring an in-ground pool with a new liner and skimmer, along with a beautiful four-season porch overlooking the pool. With its flexible layout, thoughtful updates, and peaceful setting, this home is ready for its next chapter!

Exceptional stone and shingle country colonial set back privately on picturesque 1.24 acres with 18'x35' heated, salt water, gunite, pool with auto cover and sun deck for in-pool lounging, installed in 2022. Extensive updates and designer appointments throughout with open flow, stunning hardwood floors, 9' ceilings, plus custom millwork, moldings, and built-ins throughout. The heart of this inviting home is the expansive remodeled kitchen with gorgeous timbered ceiling, quartz counters, Stainless Steel appliances including gas range, double ovens and warming drawer, center island with bar seating, and sunny breakfast room with angled wall of windows, wide open to the dramatic family room with soaring cathedral ceiling, fireplace, and two story wall of windows overlooking the extensive blue stone patio and pool. The main level also features the formal dining room; living room/library with 2nd fireplace flanked by floor to ceiling built-in bookshelves; plus private bonus den/optional bedroom; full bath; and convenient laundry room with new washer/dryer. The second floor is equally impressive with elegant primary suite with luxe bath and huge double walk-in-closet; plus 3 more generous bedrooms, 1 ensuite and 2 with Jack and Jill bath. Total 4,295 sf with 4-5 bedrooms, 4 full/1 half baths including the sprawling finished lower level with media room, rec/play room, fitness room & half bath. Of note: heated gutters and garage; built-in audio; whole house automatic generator. Top location, minutes to downtown Ridgefield and just 60 miles to Midtown.

Beautifully sited on nearly eight private acres with spectacular views, this turn-key Sherman estate encompasses an amenity-filled main residence, renovated guest house, spring-fed pond, classic stone walls, and exquisite English gardens. Offering luxurious resort-style living in one of Sherman's most captivating settings, the home welcomes you with a marble foyer leading to a dramatic double-height living room, where a wall of glass frames the breathtaking vistas. There are two luxurious primary suites - one on each level - with the main-level BR featuring a fireplace and French doors opening to the expansive deck. The top-of-the-line eat-in kitchen features custom cherry cabinetry, a sun-filled dining area, adjoining butler's pantry, and formal dining room. Upstairs are the second ensuite primary bedroom, two additional bedrooms, a den, full bath, and flexible space/artist's studio. The walk-out lower level is an exceptional space, with custom millwork, marble floors, an antique English bar, gas fireplace, sauna, and gym. Pocket doors reveal a spectacular in-home spa featuring a 24' x 14' heated Gunite spa pool, radiant heated floors, a Desert Aire climate-control system, and walls of glass overlooking the mountains and gardens. Outside, stone pathways meander through beautifully landscaped English gardens to the spring-fed pond and guest house, while classic stone walls and a circular driveway connect the main residence, guest house, and attached and detached garages. Despite its remarkable privacy, this beautiful estate is just minutes from Metro-North rail service and less than ninety minutes from New York City. Extensive recent improvements include a new roof, a newly paved circular driveway with restored stone walls, generator, beautifully updated bathrooms, custom built-ins, a steam room, a new four-person sauna, fresh interior and exterior paint, a fully renovated guest house, and thoughtfully redesigned Zen and English gardens. See attached list of features and capital improvements.

REDUCED to SELL! Quintessential Vintage Farmhouse, circa 1784, on 2.31 glorious, manicured acs, adorned w/perennial gardens that signal the seasons. Offering the best of today's modern amenities with the charm of yesteryear, this 4 BR, 4.5 bath Colonial Farmhouse w/3 bay barn garage, is the ultimate for the antique lover. The main entry, showcases a formal living room w/fireplace, adjacent dining room with bay window plus a den with fireplace serving as an ideal TV room or reading room. The rear of the house forms the focal point with/its covered Mahogany porch, wrap deck & stone terrace w/stone fireplace viewing the pool & gardens. A vaulted primary suite hosts balcony, private bath, huge WIC w/built-ins & a TV room. New Chef's kitchen w/high end appliances, 3 working fireplaces, new wide board honed floors in great room & kitchen, granite counters, serving bar, coffee bar & more; ideal for the entertainer. The in ground gunite pool, surrounded by perennial gardens & cast aluminum fencing is set apart but easily viewed from the main house. A 3 bay barn garage is enhanced with a loft housing a gym, full bath and extra guest room, possibly an optional in-law suite. A true gem of the past, restored lovingly through generations, the provenance carefully protected from family to family.Other upgrades incl:new roof (2025), new windows , new hot water heater (2023),new well pump & tank( 2026), whole house generator, updated baths, wood stove in family room, new vinyl fencing+

Striking New England colonial farmhouse to be built by local craftsman, Chris Santini, known for decades for his commitment to quality and excellence. This exceptional new construction home will offer top attention to detail, town water and sewer, plus premier walk to town location on a quiet cul-de-sac with level one acre, sprawling backyard and future pool site. Total 5,017 square feet with 4 bedrooms, 4 full/1 half baths, plus further potential to customize in lower level and walk-up third floor. Total 4,217 square feet on the 1st and 2nd floors, plus additional 800 square feet in finished lower level game/recreation room with full bath. This casually elegant home will offer a covered front porch with standing seam metal roof and bluestone floor; wood clapboard siding with wood shutters and S hooks; CertainTeed architectural shingled asphalt roof; attached three car garage plus covered walkway entry into spacious mudroom with built-in hooks/cubbies and 2 walk-in closets. Custom millwork and moldings throughout; 3.5" oak hardwood floors; two-story foyer; powder room; double coat closets; plus optimal floor plan. The main level features both formal living and dining rooms; butler's pantry with wet bar and wine chiller; private office with French doors to a stone patio; plus chef's kitchen with high end professional stainless steel appliances, quartz counters, center island, walk-in pantry, and breakfast room, wide open to the large family room with stone fireplace plus wall of windows/French sliders to the expansive rear stone patio. The second floor offers the luxe primary suite featuring dressing area with double walk-in closets, plus an elegant private bath with Quartz topped double vanity, soaking tub, and separate frameless shower. There is a second generous ensuite bedroom with private bath; two more bedrooms with Jack & Jill bath; plus convenient upstairs laundry room with sink. So much more: high efficiency propane heat; propane fired tankless instant hot water heater; plus wired for future whole house generator with automatic transfer switch. The walk-up attic with be pre-plumbed for a future full bath. Still time to customize all appointments. Don't miss this opportunity to custom build your dream home, just a short walk to historic downtown Ridgefield for shops, restaurants, park, library, and theaters, plus just 58 miles to Midtown!

Architecturally Masterful design, inspired by famed architect HR Richardson's classic exteriors is married with a sophisticated, modern interior plan. This unique Redding estate home offers a scenic, private gated 9.54 acres and over 7200SF of modern living. The grand and gracious living room and dining rooms, formerly owned by a classical pianist, were utilized for elegant gatherings and concerts in the area & large enough for a concert grand. Warmed by a mantled fireplace with built-ins, the living area opens to a formal dining area to seat 12 special guests. The elegant foyer greets you with an expertly crafted, freestanding curved stair that leads to the upper floor. Adjacent to the dining room is a stark white kitchen with new quartz counters, an unusual contrast to the warm woods of the white oak floors and family room with stone,raised hearth fireplace. An adjacent Pecan wood study with walls of bookshelves and file drawers; an idea home office. A main level primary suite offers a series of custom closet built-ins & marble bath with shower, double sinks and even a bidet; a private owner retreat. Also, on this level is an excercise room w/whirlpool tub, sauna & full bath. Head up the back stair to the 2nd level w/2 bedroom suites, one serving as an ideal studio, with sink and an additional bedroom with large marble bath. A third bedroom & another full bath. The lower level offers a game room w/wood stove, office & den/ library wall. Inground gunite pool, 3 car garage

Nestled amid 4.39 acres of beautifully landscaped, wooded grounds, The Retreat is an exceptional Ridgefield estate where refined living, privacy, and resort-inspired amenities come together. Designed for both grand entertaining and effortless everyday living, the property unfolds through lush gardens, impressive stonework, expansive terraces and patios, and a spectacular gunite pool, creating a serene setting reminiscent of a private luxury resort. The beautifully appointed main residence features a first-floor primary suite, two private offices, three additional bedrooms, a striking brick fireplace, and an elegant kitchen with butler's pantry and laundry. An expansive wraparound deck creates a seamless connection between the interior and surrounding landscape, offering an extraordinary backdrop for entertaining or quiet relaxation. The finished walk-out lower level is an entertainer's dreamscape, complete with a sophisticated full bar, wine cellar, cigar room with dedicated smoke-extraction HVAC, spacious family room, and a luxurious spa bath with steam room and wall jets. A separate cottage adds a legal studio apartment with a private entrance and outdoor sitting area, plus an additional bonus room and half bath above-ideal for guests, extended stays, or a private retreat. A dedicated indoor wellness spa with a hot tub, sauna, and massage area further elevates the experience. Secluded and tranquil, yet moments from Ridgefield's celebrated Main Street

Half Moon Farm delivers an idyllic Hudson Valley escape just one hour from Manhattan. Set on over three serene acres, this meticulously updated 19th-century farmhouse seamlessly connects historic authenticity with modern luxury for buyers seeking a private country retreat or turnkey farm property. Originally built in the early 1800s, the historically registered three-bedroom, two-bathroom residence features restored original wood floors, light-filled interiors, and classic architectural proportions. A welcoming entry opens to a sunlit living room with a wood-burning fireplace, custom built-ins, and a quiet reading nook. Double doors lead directly to a covered patio framed by climbing grapevines and honeysuckle that invites hummingbirds into the surrounding organic herb and flower gardens. The property offers established plantings of rosemary, oregano, thyme, basil, lavender, dill, chives, sage, and lemon balm set alongside roses and butterfly bushes with rich, organically maintained soil. The kitchen pairs rustic charm with modern efficiency, featuring butcher block countertops, custom cabinetry, stainless steel appliances, and an expansive pantry with exceptional storage. A finished lower level adds flexible living space with radiant heated floors, a recreation area, and direct walkout access to the landscaped backyard. Outdoors, mature 200-to-300-year-old maple trees and historic stonework surround a secluded bluestone saltwater pool set within a former sheep paddock. The grounds double as a thriving natural sanctuary frequently visited by native wildlife, including eagles, screech owls, rabbits, indigenous tortoises, and wild turkeys. Auxiliary structures like a sizable garden shed and flexible acreage provide prime potential for future guest cottages or secondary outbuildings. Located moments from the Sedgewood Club beachfront and golf course, Half Moon Farm represents an opportunity to own an eco-conscious Hudson Valley retreat within convenient commuting distance of New York City.

Come fall in love. This picturesque 1920s sprawling cottage is on the market for the first time in 38 years. As you enter the 2.94 acre property you feel the magic of things to come. Flowers, mature trees and original rock walls abound. There are grassy areas for running, woods for exploring and a 19' by 38' Gunite pool for relaxing. A bluestone path leads to a welcoming entry located in the oldest part of the house whose size defies initial expectations. Cross the wide board floors to the dining room where large windows bring in natural light and showcase a delightful all season backyard view. The paneled living room with picture window, wood-burning fireplace, built-ins and period hardware exudes a cozy warmth. Just down the hall is one of two potential main level primary suites. This one includes a fireplace and office. Head the other direction to find the kitchen with a breakfast nook which opens to a covered balcony and that spectacular backyard view. Just beyond is the second potential primary bedroom opening to the balcony. The third bedroom and another full bath complete this level. Downstairs find a spacious family room, laundry, den/office and another covered porch as well as the two car garage. And don't miss the two outdoor shower cabanas! Located in the desirable Farmingville area, this home is highly convenient to Ridgefield's shopping, restaurants and cultural activities, schools and commute routes. The Hickories organic farm is down the road. Come see!

Welcome to one of Main Street's most recognizable homes, the iconic & brightly colored Gothic Revival Victorian, built Ca. 1826, offering an exceptionally private & expansive 1.94 acre lot plus a separate 3,684 sf Carriage/Pool House. Working with Peter Coffin, Architect, and the Historic District Commission, the home underwent a meticulous full restoration/renovation, thoughtfully balancing historic preservation with modern luxury updates. Over $10M has been spent in top of the line improvements and designer appointments inside and out. This highly refined residence offers a total of 5,778 sf including 4,546 sf on the 1st & 2nd floors, 303 sf in the finished 3rd floor, plus 929 sf in the lower level. Total 15 rooms, four bedrooms, four full and one half bath, three fireplaces, front and back stairways, plus brick driveway/courtyard leading to the three story carriage/pool house. The ultimate lifestyle "party barn," it features millwork reclaimed from PA mushroom barns; two car garage; two fireplaces; ensuite Bedroom & overflow guest "bunk room"; two full/one half baths; full gym with steam shower/changing room; game room/bar; poker/card room; arcade; 30+ seat movie theater; plus kitchen/great room open to the pool. The resort like entertaining area features a sprawling cut stone patio, custom fireplace with propane assisted starter, waterfalls, built-in outdoor kitchen with grill/sink/fridge, heated, saltwater, gunite pool and spa, custom built pergola, wired for sound/TV, plus expansive back lawn and wooded privacy.

Unprecedented opportunity to purchase two landmark, historic residences, situated side by side on Ridgefield's beloved Main St., which have been developed into an unparalleled lifestyle compound. This once in a lifetime sale includes the treasured Hawley House at 236 Main St. - Ridgefield's oldest home, on its original lot (5) which was built by the proprietors in 1713 for the Rev. Thomas Hawley, first pastor and town clerk. It also includes 250 Main St. - the iconic and brightly colored neighboring Gothic Revival Victorian, built Ca. 1826 by Hawley descendants. Working with Peter Coffin of DCA Architects and the Historic District Commission, the home underwent a meticulous full restoration and renovation, thoughtfully balancing historic preservation with modern luxury updates. Over $10M has been spent in top of the line improvements and designer appointments inside and out. Together, both homes span a pastoral 3.16 acres, juxtaposing sidewalks to vibrant downtown Ridgefield with rear privacy including two magnificent barns. 236 Main's "Red Barn," Ca. 1900 and renovated in 2012 features: 2,015 sf, indoor basketball court, home office with conference room, arts and crafts studio, 1 full and two half baths and two car garage. 250 Main's Pool with Carriage house includes: 3,684 sf, 1-2 bedrooms, two full and one half baths, two fireplaces, two car garage (two Tesla chargers), gym with sauna, game room with bar, poker room, arcade, 30+ seat movie theater, plus kitchen with great room open to the heated, gunite, saltwater pool, spa and outdoor resort oasis.

Set on 2.31 private, level, and professionally landscaped acres, this classic four-bedroom Colonial in Newtown offers exceptional space and character. The property features a beautifully maintained backyard retreat complete with an in-ground pool, a fire pit, a basketball hoop, and an expansive deck perfectly suited for grilling, dining, or lounging. Recent exterior updates ensure peace of mind, including a new roof in 2019, a pool liner replaced in 2023, a new pool pump in 2026, and a freshly painted and stained exterior and deck. Inside, the home provides an effortless flow for everyday living and entertaining. The spacious eat-in kitchen is highlighted by serpentine stone counters, a center island, generous cabinetry, and direct sliding-door access to the outdoor deck. Adjacent to the kitchen, the family room serves as a stunning focal point, anchored by a prominent brick fireplace. A formal living room, a formal dining room featuring hardwood floors, and a convenient powder room complete the expansive main level. Upstairs, the primary suite provides a relaxing retreat with a private en-suite bathroom and a walk-in closet. Three additional generously sized bedrooms offer versatile layout options, providing ample room for a home office, craft space, or guest accommodations. The full, unfinished basement adds significant value with excellent storage capacity, room to create a home gym or workshop, and interior stairs leading directly to the attached three-car garage. Situated with incredibly convenient access to major routes, this property offers excellent proximity to local restaurants, shopping centers, parks, and recreational facilities.

Beyond stone entry gates, a long driveway leads to this 1958 midcentury home, set well back from the road on 7.11 acres in Bridgewater. Six fireplaces, exposed-beam ceilings, expansive windows and open living areas connect the interiors to long western views. The open-plan kitchen features a substantial soapstone preparation island with abundant storage, a full-size Viking refrigerator/freezer and a six-burner range with grill and plancha. A fireplace and adjoining breakfast area make it the natural center of the house. A separate dining room with fireplace and a light-filled living room with a built-in bar provide space for larger occasions. The main-level primary suite includes an office and walk-in closet. Its bath pairs two vanities with a large walk-in shower and a clawfoot tub positioned to take in the view. At pool level, additional bedrooms, a kitchenette, laundry, a den and sitting rooms provide flexibility for guests and relaxation. Outside, the heated swimming pool, stone terraces, covered seating and outdoor dining areas open onto broad lawns and flowering gardens. Apple, pear, plumb and peach trees mingle with mature willows, and stone walls define the grounds. The pond freezes into a skating rink in winter; in summer, the willows along its bank are the place to sit and listen to the frogs. A horse barn with water and electricity offers stabling, loft space, storage and a workshop, with a riding ring nearby. A three-car garage completes the outbuildings. From the kitchen fireplace to the poolside terraces, the home offers places to gather and watch remarkable western sunsets. Recent updates include: New Kitchen Renovation. Whole house painted New AC compressor Viking Fridge freezer Patio Bluestone Extensive drainage system Stonewalls Pool Heater Metal Roof 2015

Rarely available. 1880 antique gem on 10 acres, with a first level primary bedroom and bath, situated on one of Bridgewater's most prestigious and quiet roads, offering a private setting. This residence masterfully blends historic character with an airy, open floor plan where the kitchen flows seamlessly into a spacious great room and a formal living room anchored by a classic fireplace. The interior living space consists of a main floor primary bedroom and bath, second level with 2 bedrooms and shared bath and a third level bedroom with it's own bath. The spaces transition beautifully to a 24 x 18 screened porch with slate flooring, opening onto a bluestone terrace. Perfect for entertaining, the terrace overlooks the pool and captures western exposures. The property is further enhanced by a two-story barn, providing ample space for storage or workshop. This is a unique opportunity to own a quintessential New England retreat in a premier location.