luxury houses with pool for sale Middlebury, United States

Just minutes from Main Street, shopping, restaurants, state parks, I-84, and everyday conveniences, this 5BR home is tucked away at the end of a private road on 2.9 beautiful wooded acres. Located approximately 85 miles from New York City, the property offers privacy, and plenty of room to explore, garden, entertain, or simply enjoy the peaceful natural setting. A covered front porch welcomes you into a spacious foyer where hardwood flooring extends throughout much of the home. The sun-filled living room features oversized windows, built-in bookshelves, and a wood stove, creating a warm and comfortable gathering space. A highlight of the floor plan is the three bedrooms on the main level, including the primary bedroom, offering flexibility for single-level living, guests, a home office, or multigenerational needs. The main level also includes an eat-in kitchen with a large pantry, a dining room, a full bath, and a bright four-season room with large sliders overlooking the wooded landscape. Upstairs are two additional bedrooms and a half bath with potential for future expansion. The unfinished lower level offers workshop space, laundry and mechanical areas, a storage room suitable for a wine or root cellar, and access to the two-car tandem garage. Outside, enjoy the inground pool, garden paths, open grassy areas for recreation or play, scenic stone walls, multiple outbuildings and woodsheds (conveyed as is), and ample parking. Significant improvements have already been completed, including a new roof (2023), furnace (2023), well pump, tank, and cap (2024), pool liner, pump, and filter (2024), and a new septic tank with two distribution boxes (2026). A whole-house Generac generator and newer gutters provide additional peace of mind. The property may offer subdivision potential, subject to municipal approvals. Buyers should perform their own due diligence regarding any development possibilities. Surrounded by nature, this home is ready for its next owner to make it their own.

* A beautiful 3-bedroom historic farmhouse * A separate 2-bedroom guest house * A pristine 6.71-acre building lot Move in and enjoy lush, pastoral Roxbury right away in the charming and immaculate 3-bedroom, c. 1817 main house, and host family and guests in the separate 2-bedroom guest house. The adjacent 6.71-acre parcel at the rear lets you protect your views and privacy forever. You can also build the 4-bedroom estate of your dreams on this approved building lot, with its own driveway and road access. Or use the mostly flat lot as an orchard or garden, or hold the separate parcel as an investment to sell in the future. The lot abuts preserved land. Located in southern Roxbury, just 90 minutes from New York City, the main residence exudes rustic character, with original hand-hewn beams, wide-plank oak floors, a wood-burning fireplace, and classic plaster walls. A brand-new standing-seam metal roof carries a lifetime guarantee. At the heart of the house is a spacious eat-in kitchen. On one side are a formal dining room and a library, and on the other is a sunlit double living room wrapped in windows. The 658-square-foot guest house overlooks a spring-fed pond and Little Jacks Brook. It has a generous living room, two bedrooms, and a full bath, and it runs on its own well and septic system. The grounds are serene and beautifully landscaped, with a cantilevered "waterfront" sun deck, mature trees, lush gardens, and a gently rolling lawn. This wonderful home has been frequently published and blends history, potential, and natural beauty in one of Litchfield County's most coveted locations. The possibilities of this Roxbury compound are many and endless. Additional purchase options: Main House and Guest House on 2 acre deeded lot $695,000 or building lot 6.71 acres $395,000. House buyer has right of first refusal, lot cannot be sold until home is sold.

Perched atop a serene landscape, this custom-built estate seamlessly marries architectural sophistication with absolute tranquility. Wrapped in a timeless blend of custom stucco and brick, this property is enveloped by professionally designed landscaping. The residence offers a private and secluded sanctuary complete with a sparkling built-in pool and spa. In the crisp autumn and winter months, enjoy breathtaking seasonal views of the glittering Southington city lights below, all while remaining just moments from the region's finest shopping, dining, and social amenities. Upon entering, the majestic main foyer welcomes you with a graceful curved staircase, setting an elegant tone that flows effortlessly throughout the open-concept layout. The main level is designed for both entertaining and comfortable daily living, featuring a light-filled living room anchored by a cozy fireplace, an adjacent formal dining room, a private den, and a conveniently located powder room. At the heart of the home lies a magnificent family room, where natural light pours in to highlight rich hardwood floors, a dramatic floor-to-ceiling fireplace, and extraordinary crown molding. Culinary enthusiasts will fall in love with the chef's kitchen, expertly appointed with sleek granite countertops, a massive center island, a professional-grade Viking stove, and a Sub-Zero refrigerator, all complemented by a sunlit casual dining area. The primary suite is a true private haven. French doors open directly

Tucked away at the terminus of a quiet dirt road, this 13-plus-acre sanctuary delivers absolute privacy alongside uncompromising mid century modern luxury. Approached via a winding scenic driveway, the property opens to reveal sweeping, recently opened panoramic vistas of Nettleton Hollow, complete with a tranquil brook and quintessential Litchfield County countryside. At the heart of the estate is a masterfully updated 1950s residence. Inside, striking vaulted ceilings elevate the freshly painted public spaces, and renovated hardwood floors, all anchored by a dramatic central fireplace with venetian plaster finish. Oversized plate-glass windows pull double duty, bathing the interiors in natural light while perfectly framing the idyllic valley views. The main and upper level feature a remarkably spacious primary suite, alongside two additional bedrooms and three-and-a-half baths. Designed with seamless hosting in mind, the lower level offers a private, full walk-out fourth bedroom suite equipped with radiant heated floors. Outside, southern exposure warms a series of expansive entertaining terraces leading to a 40-foot gunite pool with an automatic cover. Practical luxuries include a dedicated pet-fenced yard, comprehensive mechanical upgrades, generator, and abundant parking for entertaining. This property offers immediate access to nature, sitting just a short stroll from Steep Rock Land Trust's hidden gem, the Johnson Farm Preserve. Yet, this total woodland immersion doesn't sacrifice convenience: under five minutes from the world-class Mayflower Inn & Spa, and less than a 15-minute drive to the acclaimed dining, boutiques, and everyday services of New Preston, Washington Depot, and Woodbury. Peace and Serenity Await.

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.

Spacious and Welcoming Cape on a Cul-de-Sac! Nestled perfectly in a private cul-de-sac and located in close proximity to the scenic Ledges Nature Preserve, this well maintained sprawling 4-bedroom Cape offers a wonderful blend of timeless charm, modern updates, and fantastic spaces for everyday living. The layout features a sought-after first-level primary bedroom. You will find beautiful hardwood floors spanning the living areas and tile in the foyer, mudroom kitchen and bathrooms. The kitchen space allow for hosting, featuring classic Corian countertops, and island, plenty of cabinet storage, and direct access from the garage for easy grocery unloading. Transition seamlessly from indoor to outdoor living with a heated sunroom for year-round enjoyment and a lovely screened-in porch perfect for bug-free relaxation. Major peace-of-mind upgrades are already done, featuring updated bathrooms and a new roof. The layout includes four bedrooms two and half bathrooms and a finished walk-out basement. This lower level provides plenty of storage space alongside a large, workroom for projects and hobbies. Outside, enjoy your private backyard retreat centered around a sparkling pool, complete with a solar cover to keep the water warm. Practical features round out this property, including tilt windows for easy cleaning, a dedicated generator plug for power backup and a large storage shed fully equipped with electricity. Bring your personal touches to make this house yours!

Stone Bridge: The Ultimate Classic Country Estate - PERFECTION AND READY TO MOVE IN! Embodying the pinnacle of refined country living, "Stone Bridge" is a magnificent stone and shingle estate with Elevator to all floors and Geothermal Heating, that seamlessly marries timeless architectural grandeur with state-of-the-art modern amenities. Situated on over 24.9 private, bucolic acres in Washington, Connecticut's highly desirable Nettleton Hollow area, this masterfully crafted property offers an unparalleled sanctuary of elegance and privacy. Constructed by the HOBI Award-winning Corbo Associates, the residence spans more than 7,000 square feet of sophisticated living space, complemented by an additionally finished 3,100 square feet on the lower level. A seamless indoor-outdoor flow defines the main living areas, which open gracefully onto sprawling terraces and a covered patio complete with an outdoor fireplace. The manicured grounds serve as a private resort, featuring mature plantings, artisanal stonework, a full irrigation system, and a pristine, heated gunite pool. Inside, soaring ceilings and expansive walls of glass flood every room with natural light while bringing the breathtaking countryside views indoors. The estate features five luxurious bedroom suites, including the rare flexibility of both first- and second-floor primary retreats. An elevator effortlessly ensures absolute accessibility throughout the home. An entertainer's paradise, the estate boasts seven fireplaces, an elegant library, home theater, a game room, gym and a spectacular 1,500-bottle wine cellar with a dedicated tasting room. Culinary enthusiasts will appreciate the top-of-the-line main kitchen, which serves as the heart of the home, alongside a full butler's kitchen designed for seamless event hosting. Built to the highest standards of construction and energy efficiency, the home features sound-dampened walls, a comprehensive security system, an integrated generator, and central vacuum. Future-proof technology is woven throughout the property, utilizing a cutting-edge geothermal heating and cooling system and Cat 6 audio wiring for premium sound, data, and internet connectivity. The estate is approached via a long, meandering driveway that overlooks a nearby pond, leading to a three-car garage connected via a stately porte-cochere to a second garage. Stone Bridge is more than a residence; it is an extraordinary country lifestyle.

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+

Set back on a private 4.48-acre interior lot in a magnificent subdivision in New Milford, this updated Farmhouse Colonial features 6 bedrooms, 3 full baths, and 2 half baths across multiple expansive levels with an in-law apartment. The front porch opens into a bright entrance foyer with tile floors that extend into the elegant formal living and dining spaces, highlighted by classic crown molding and chair rail accents. The open-concept eat-in kitchen features custom maple cabinetry, granite countertops, tiled flooring, stainless steel appliances, and a dedicated pantry. The adjacent dining area leads directly into an expanded, stunning, sun-drenched sunroom featuring Bruce hardwood floors, double lighted ceiling fans, and a corner wall of windows with sliding glass doors leading to the deck, pool, and backyard area. Nearby, the family room offers wide-plank hardwood flooring, a ceiling fan, and a functional wood-burning stove. The main level is completed by a half bath and a decorated laundry room with built-in cabinets. A white spindle staircase leads to the upper level, which hosts five bedrooms and two full bathrooms, linked by a hardwood hallway. The primary bedroom suite includes lush carpet flooring, a separate dressing room with double closets, and an oversized primary bath featuring a jetted tub set beneath a palladium window and tray ceiling, a custom tiled walk-in shower, and custom cherry cabinetry. A secondary bedroom suite features a walk-in closet, stunning pool views, and a private half bath. Three additional bedrooms feature laminate flooring and are served by a central full bathroom on the upper level. The walk-out lower level boasts a private in-law apartment complete with its own dedicated exterior entrance, a private lower deck, and an interior staircase connecting to the main home. This separate living unit includes a kitchenette, dining and living area, full bathroom, double closets, and a legal bedroom with dual entry points. Outdoor living features a double-level deck overlooking a sprawling backyard with a fenced-in, newly surfaced Gunite in-ground pool equipped with a pool house, covered pool bar surrounded by stone patio pavers. Additional features include a built-in stone fire pit, a storage shed, and stone retaining walls bordering established gardens. 2-car attached garage on the main residence, alongside a 2-car detached workshop garage equipped with an air compressor, built-in workbenches, and overhead storage. The home includes a brand-new roof on both the main house and garage, a new central air conditioning system, generator-ready, and a full attic for extra storage.

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.

A rare offering that exudes sophistication and sanctuary, this striking contemporary estate-originally built in 1984 and thoughtfully reimagined for modern living-spans over 5,526 square feet of refined yet inviting space. Privately nestled within a tranquil suburban setting, this property delivers a true escape while remaining moments from premier shopping, dining, and everyday conveniences, an ideal retreat for those craving a seamless blend of country calm and cosmopolitan accessibility. Designed with both scale and comfort in mind, this home features an abundance of expansive living spaces, where architectural intrigue meets livable luxury. Each room unfolds with intention - grand in proportion yet intimate in feel, creating a series of elegant retreats throughout the home. Recent upgrades elevate both form and function, including newly installed flooring, a high-efficiency HVAC system, and whole-house generator system ensuring comfort and peace of mind year-round. Storage is exceptional, with generous closet space rarely found in homes of this era. The outdoor experience is equally compelling. Set against a serene backdrop, the property boasts a private, resort-style in-ground pool and whirlpool spa along with a full-size tennis court-perfect for both entertaining and quiet relaxation. A unique indoor hot tub adds an additional layer of year-round indulgence. This is more than a home - it's a destination.

Escape to an award-winning estate nestled in the heart of Washington, CT-just 90 miles from New York City. Situated on over 80 acres of pristine, level land, this exceptional modern farmhouse offers a rare combination of architectural excellence, luxurious amenities, and unparalleled natural beauty. Featured in New England Home and honored with CTC&G's prestigious Innovation in Design award, this residence is a masterclass in sophisticated country living. A tree-lined driveway bordered by 1,000+ feet of classic stone walls welcomes you to the property, setting the tone for the elegance and privacy that await. The 5-bedroom, 4 full and 2 half-bath main house is thoughtfully designed for both grand entertaining and intimate daily living, with a guest house, heated pool and spa, orchard, and serene pond completing the estate. Inside, open-concept living spaces are defined by warm wood beams and a stunning double-sided fireplace. The living room flows seamlessly to a covered porch with peaceful pond views-ideal for year-round enjoyment. The lower level includes a gym, game room, and spacious lounge, while dedicated office space accommodates work-from-home flexibility. Outdoors, a pool, spa and stone terrace offers panoramic views of the surrounding forest, alive with native wildlife. Minutes from Lake Waramaug, Steep Rock Preserve, and the boutiques eateries of Washington Depot and New Preston, this home is perfectly positioned for both adventure and relaxation. The acreage allows for subdivision potential, adding long-term value to this already remarkable retreat. A rare offering that combines timeless design, top-tier amenities, and the best of Litchfield County-this estate is the definition of refined country living.

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.

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 6 acres on a cul-de-sac, offering a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

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.

Opportunity knocks! Available for the first time since it was built on .93 acre on the cul-de-sac, this stately Colonial offers turn-key living. Open the front door to the welcoming foyer and your eye is drawn to the detail work that surrounds you. A formal living room is to the right and the dining room to the left opens to the family room with gas fireplace and then to the kitchen which will thrill the most discerning cook. The island provides plenty of workspace as well as abundant seating for family and friends. Entertaining for holidays or watching a game is fun and easy with this floor plan design. The covered porch provides additional entertaining space. Outside is a spectacular private outdoor oasis designed for ultimate relaxation and entertaining. The centerpiece of the backyard is a stunning in-ground pool, surrounded by a concrete patio and an expansive composite deck. There is endless space for unwinding at home or hosting large gatherings. Seamlessly connecting the indoor and outdoor living areas, this backyard is built for creating memories. Upstairs features a magnificent primary suite, a second family room, and three additional spacious bedrooms. Second floor laundry room features another half bath. Enjoy phenomenal storage, an attached, oversized 3-car garage, plus a vast walk-out basement perfect for a gym or playroom. In addition to the main house, a versatile one bedroom in-law suite is accessed via deck, driveway and garage.

Set in a peaceful Redding setting, 87 Giles Hill Road is a charming Cape with an inviting floor plan and an exceptional outdoor space designed for both relaxation and entertaining. The home has a warm and welcoming feel, with hardwood floors throughout the main living areas and a comfortable flow from room to room. Generous windows bring in natural light, while two bedrooms located upstairs offer private retreats separate from the main living spaces. Outside, the property truly shines. A custom heated pool with spa and waterfall creates a private backyard retreat, providing a wonderful setting for summer days, outdoor entertaining, or simply relaxing and enjoying the surrounding landscape. With its classic Cape design, thoughtful floor plan, and resort-like pool setting, 87 Giles Hill Road offers a wonderful opportunity to enjoy the privacy, natural beauty, and relaxed lifestyle that make Redding such a special place to call home.