Luxury houses with pool for sale Hillsdale, United States

Welcome to an exceptional Hudson Valley retreat, offering unparalleled space, comfort, and recreational amenities across 56+ private acres. This stunning 6 bedroom, 6.5 bath estate is the ultimate compound or a lucrative opportunity for investors seeking a proven Airbnb performer. Nestled in a secluded setting, the property features a swimmable pond with its own docks and bridge, plus scenic trails perfect for snowmobiling, hiking, and cross-country skiing--all from your own backyard. Designed for gatherings and entertaining, the grand open-concept living, dining, and kitchen area is anchored by a dramatic stone fireplace with a propane stove insert. The chef's kitchen is outfitted with two refrigerators, two ovens, a five-burner stove, and a wine fridge--ideal for preparing feasts for a crowd. An expansive laundry room boasts three washers and six dryers to handle large groups with ease. The indoor heated pool, personal gym, and game room, complemented by a second cozy fireplace with propane stove insert, ensures endless indoor fun, while two private cabins offer exciting renovation potential. Updated mechanicals, on-demand propane hot water, a whole house generator, and a detached two-car garage with its own well provide peace of mind and convenience. Property outfitted with 8 kayaks and a paddle boat. Sub-dividable acreage allows for future expansion or investment flexibility. Whether seeking a weekend sanctuary, a multifaceted compound, or a high-performing rental, this extraordinary property offers boundless possibilities for relaxation, recreation, and return.

Experience the luxury of gracious proportions, impeccable details, and stunning design in this exquisite classical villa that would be as at home in Italy as it is in the Berkshire landscape. Protected views of mountains, rolling hills, and meadows surround the 6.9-acre estate. The atmosphere of sophisticated luxury begins with the approach through an allee of willow trees and in the front courtyard, edged with stately Bradford pear trees and arbor vitae and anchored by the 2716sf, single-level residence and a matched pair of outbuildings--a two-car garage and a garden house. The front entry of architect-designed residence leads to a luminous interior with tall ceilings, reflective white walls, generous windows and 19 screened French doors that welcome sunlight and breezes and provide for ideal interior-exterior living. To the left of the entry are a living room with a wood-burning Rumford fireplace and hallway to the primary suite with an airy, comfortable bedroom, refined, restorative bath, and walk-in closet/dressing room. To the right, a spacious dining room, well-appointed kitchen, screened porch, and hallway to two bedrooms and full bath. The U-shaped floor plan embraces a secluded formal garden, reflecting pool with fountain, patio with pergola, and 40' lap pool. Completed in 1998, every element of the residence attests to architectural intelligence, superior craftsmanship, and love for the bucolic landscape. The high level of quality is evident in the visually commanding millwork, true stucco exterior, lath-and plaster walls in the principal rooms, east and south pergolas, west-facing screened porch, and sensitive choreography of space. With roots in the classical architecture of ancient Rome, this is a thoroughly modern dwelling replete with whole-house fan, air conditioning, generator, security system, 630-foot drilled well, and chef-ready appliances. The result is a home that feels both sculptural and deeply connected to its setting. With protected views, total privacy, and proximity to South County amenities (7 minutes to Guido's), this is a rare Berkshire offering -- serene, architecturally stunning, and eminently livable.

Fantastic opportunity to own a home in a peaceful cul-de-sac within the desirable Cornwall Estates. This lovely home sits on a level lot with almost 2.5 bucolic acres. Spanning just over 2,000 square feet, the home features a convenient first-floor primary bedroom and bathroom, vaulted ceiling in the living room and a screened in porch that leads to a large, partially fenced in backyard. Many recent updates and upgrades including kitchen and bathrooms, as well as the furnace and central AC system replacement. All of this and a heated community pool nearby and Great Barrington just minutes away, make this home ready for its next owners to create their own Berkshire journey and memories. Replaced/Updated Within the Last 3 Years: furnace, central AC, kitchen, bathrooms, all exterior doors, basement improvements Community Details: -8 homes in the community -$1,500 transfer fee due at closing from buyers to the Association -HOA dues will decrease to $900 per quarter ($300 per month) after two loans are paid off in July and October 2027 Rental Policy: -First rental term has a 28-day minimum -Second rental term has a 7-day minimum -Maximum rental term is 1 year -Lease extensions must be approved by the Association

Welcome to Serenity Hill. This 1994 Cape style home captures the timeless charm of the Berkshires from the moment you arrive. At the entrance, stately stone pillars and a classic stone wall offer a graceful welcome, setting the tone for the calm, natural beauty that defines life in the Berkshires. Located on the border of Great Barrington, this Sheffield home is on a peaceful, quiet country road. Less than a mile from Wyantenuck Country Club and just five minutes from downtown Great Barrington. This home offers a peaceful sense of seclusion without ever feeling far from the heart of the Berkshires. Inside, you'll find an airy, open layout with natural flow from room to room, designed with both comfort and connection in mind. The vaulted ceiling in the kitchen adds a sense of light and openness, while seamless transitions between the kitchen, dining area, and living room create a space that feels both cohesive and welcoming. A cozy wood-burning fireplace anchors the living room, adding warmth and charm to the heart of the home. With 3 bedrooms and 2.5 baths, every space feels intentional, comfortable yet refined rendering this home ideal for both everyday living and effortless entertaining. Thoughtful design choices enhance the home's warmth and inviting atmosphere. From the living room, multiple doors open onto a private back deck, creating a natural extension of the home's inviting flow. Beyond the deck, you'll find your own private sanctuary: a peaceful koi pond, an inviting in-ground pool, and a hot tub perfect for unwinding under the stars. Whether you're savoring quiet mornings in nature or hosting lively summer gatherings, this property offers the perfect balance of serenity and connection. This is more than just a home, it's a true Berkshire retreat, where timeless style shines in one of the area's most desirable settings.

A Classic Modern Farmhouse with Incredible Views - This home has been thoughtfully updated to provide a seamless blend of style and comfort. The property features a resplendent in-ground pool, a spacious swim pond, and a three-car garage with an inviting guest suite above.The main residence welcomes you with a charming wrap-around porch and an enchanting screened porch, both perfect for enjoying the dynamic and ever-changing views. The interior is bright and lively, with each space thoughtfully designed to capture the natural beauty of the surroundings.The gourmet kitchen, a convivial hub with a grand stone fireplace, offers direct access to the screened porch and serves as the perfect backdrop for culinary exploration and social gatherings. The first floor also includes a welcoming foyer, a serene bedroom suite, and an elegant formal living room.Upstairs, the master suite is a haven of sophistication, complete with a stone fireplace and ample space for relaxation. Two additional guest bedrooms share a Jack and Jill bathroom, providing comfort and privacy for friends.The finished lower level is dedicated to leisure and repose, crafted with the ultimate goal of relaxation in mind. Here, in this tranquil setting, you'll find the peace and privacy you desire, all within a home that exudes charm and character.

Greendale is more than a home—it is a legacy property, offering a rare opportunity to possess a piece of Hudson River history, distinguished by its panoramic vistas and enduring character. An embodiment of timeless refinement, Greendale is a distinguished historic residence set along the storied banks of the Hudson River. This exceptional estate offers commanding views of the water from an expansive, verandah - an ideal vantage point for serene mornings and resplendent sunsets. The main residence features six elegant bedrooms and four bathrooms. At its heart lies a luminous, double-height living room—an exquisite space equally suited to intimate repose or sophisticated entertaining. Beyond the home, a gracefully landscaped setting unveils a handsome stone pool, framed by mature gardens that provide a tranquil, secluded retreat. Two supplementary dwellings present opportunities for guest accommodations or an income-generating residence, adding both versatility and value.

This 70s Modern home has been revamped to a 21st century Contemporary. Perfectly situated between the spectacular east and west lakes in the Twin Lakes region of Salisbury, it's an easy walk to the lake to enjoy part ownership of the beach/lake access point, or relax in the back yard by the pool, relishing in the privacy and beauty of your surroundings. The upper level features an open floor plan with vaulted ceilings, lots of light, and wood beams. Walk out right onto the expansive deck, or enjoy the private balcony off the Master bedroom suite. The lower level has two additional bedrooms, an office, a full bath, a laundry area, and a central family room. Other features include a whole house generator, an owned solar electric system, mini-splits for climate control (heat & AC), and professionally maintained grounds. This is a clean, well kept home and property in the middle of a lake community in one of the most desirable areas in the Berkshires. Close to Salisbury, Hotchkiss, Berkshire, and Indian Mountain schools, and less than 30 minutes to the Wassaic train station.

This beautifully maintained 2-bedroom, 2.5-bath Lion's Head condominium offers comfort, style, and convenience. The inviting living room features custom shelving, a propane fireplace, and sliders opening to a private deck overlooking a peaceful wooded setting with southern exposure. The updated kitchen is equipped with stone countertops, a prep island, and high-end Bosch appliances, including a range and microwave/convection oven. A dining area with vaulted ceiling and skylight adds to the bright, airy feel. Upstairs, both bedrooms feature vaulted ceilings, including a spacious primary bedroom with ensuite bath and generous closet space. Laundry area is conveniently located on the upper level. Additional highlights include central air, engineered wood flooring, and attached one-car garage. Community amenities elevate the lifestyle with a pool and tennis court, and the central location allows for easy access to town. Recently paved roads and driveways throughout the complex reflect pride of ownership in this well-maintained and highly desirable association. Located near private schools, lakes, the Scoville Library, skiing, hiking, shops, restaurants, and Metro-North service at Wassaic.

Exquisite Shekomeko Estate with Panoramic Catskill Mountain views. Nestled on 50 private acres in the heart of the Hudson Valley, this country estate offers timeless sophistication, refined comfort, and breathtaking views of the Catskills. Designed by architect Jimmy Crisp and completed in 2004, the residence spans over 9,684 finished square feet of thoughtfully curated living space. A tree-lined driveway framed by mature red maples leads to the home’s elegant formal entry, setting the tone for what lies beyond. Inside, a chef’s kitchen anchors the main living area—perfect for both everyday living and exceptional entertaining. Upstairs offers a primary suite complete with fireplace, balcony, sitting room, double walk-in closets and a spacious primary bath. There are four additional bedrooms plus an office. The lower level includes a full gym, Pilates studio, play area, expansive wine cellar for the wine connoisseur, and a large laundry room. The home’s stone wing is a standout feature designed around a dismantled barn, showcasing a dramatic great room with vaulted, beamed ceilings, custom copper rails, a floor-to-ceiling stone fireplace, and accesses the pool. Outdoor living is equally luxurious. A beautifully landscaped 75’ x 25’ pool and spa overlook open fields and distant mountains, while a stone terrace with outdoor fireplace, dining loggia and fire pit offer ideal settings for starlit evenings. A vegetable garden adds charm and function, encouraging a farm-to-table lifestyle. Adding to the amenities is a two-car garage with a studio and bathroom above, a pole barn and a pond. Whether you're seeking a serene full-time residence or a weekend retreat, this exceptional property is a rare Hudson Valley offering that combines architectural pedigree, expansive land, and elevated country living.

Discover the perfect blend of comfort, character, and investment potential in this expansive four-bedroom, three-bath home nestled on 2 scenic acres with truly breathtaking Catskill and Berkshire mountain views. Whether you're an investor searching for a proven Airbnb success, a large family needing abundant space, or a weekender seeking the ultimate Hudson Valley getaway, this property is your opportunity. Entertain with ease in the unique four-car garage that doubles as a party pavilion, or unwind in the spectacular in-ground heated pool, surrounded by the beauty of nature. The enclosed wraparound porch, featuring walls of windows and wood floors, invites you to soak up year-round sunlight and panoramic vistas. Inside, find three finished floors of living space, with charming beamed ceilings in the kitchen and a stunning brick fireplace in the spacious first-floor primary suite. The kitchen features stainless steel appliances and 2 large windows letting in the natural sunlight while you cook. The third-floor yoga room offers an inspiring retreat space along with 2 more rooms for a den, family room, or art room. The home's thoughtful layout ensures privacy and comfort for all. Radiator heat keeps the first floor cozy, and large windows throughout maximize natural light and showcase those unforgettable mountain views. With eight parking spaces, hosting friends, family, or guests is always convenient. Once home to a beloved French restaurant, this property is rich with possibilities--ready to continue as a lucrative rental, accommodate multi-generational living, or become your personal sanctuary in the Hudson Valley. Don't miss this rare offering where history, beauty, and opportunity converge.

Experience 225 years of preserved grandeur on Nodin Farm. Nestled on 130 sprawling acres of rolling countryside, this Greek Revival has been lovingly stewarded by only four owners across more than two centuries, ensuring its soul remains as original as its architecture. The Manor House: The interior seamlessly blends the romance of the 19th century with the sophisticated comforts of the 21st. Rich wide-plank wood flooring, bespoke built-ins, hand-carved woodwork, seven fireplaces, these are just some of the original details. The gourmet kitchen has premium, professional-grade appliances, the home's bathrooms are renovated, and the estate is equipped with state-of-the-art climate control systems. The Grounds and Out Buildings: The Farm moniker only hints at the magnitude of this estate's amenities. You'll find a brick patio and a shimmering inground pool, perfect for summer afternoons. The Main Barns- A majestic gambrel-roof brick barn and a classic wooden barn, both fully restored. The Bull Barn- A charming, standalone brick structure with existing architectural plans for a luxury guest house. Auto Gallery- A massive, 7-bay brick garage complete with a professional-grade gym and a private executive office. This entire barn complex was meticulously repaired and outfitted with premium roofing in 2024. Nodin Farm is a rare convergence of history, scale, and meticulous preservation. It is an invitation to own a piece of the American story. Schedule your private tour of this 130-acre legacy estate today.

Set atop 74 acres of extraordinary privacy in the historic hamlet of New Concord, this refined center hall colonial commands sweeping views of rolling meadows, wooded trails, hay fields, and distant Catskill horizons. Bathed in sunlight throughout the day, the property offers a rare sense of peace and expansiveness, where nature, light, and craftsmanship exist in harmony. Custom-built to evoke the grace and authenticity of a 200-year-old estate, the home blends timeless architectural detail with thoughtful modern luxury. The interior unfolds with a balance of openness and intimacy, offering spaces that feel both grand and warmly livable. At the heart of the home is an expansive chef's kitchen featuring honed Vermont Danby marble countertops, Kennebec cabinetry, a spacious pantry, and top-tier appliances, including a grand-scale luxury Thermador refrigerator and plumbed Wolf steam convection oven. The kitchen flows seamlessly into an oversized casual dining area and family room, ideal for relaxed daily living and entertaining. More formal rooms include a gracious dining room, refined reception or music room, and a light-filled sunroom with fireplace. Radiant in-floor heat warms the office, kitchen and mudroom, living room and entry, and dining and music rooms, while the sunroom is served by baseboard hot water and the upper level is divided into two zones for comfort and efficiency. Nordic matte white-washed reclaimed Southern pine floors, artisan-crafted twelve-over-twelve windows, and hand-forged wrought-iron hardware lend warmth and authenticity. Five wood-burning fireplaces, including two moss-lined stone fireplaces, add character and comfort, while limestone bath tiles and a spa-like primary bath elevate everyday living. The home is fully networked with Ethernet and Wi-Fi throughout and includes multiple office spaces, abundant storage, a private guest suite, and additional guest accommodations. The estate is exceptionally well equipped for both daily living and entertaining, with a professional six-burner Garland range with salamander, griddle, grill, and dual ovens, two Bosch dishwashers, Viking bar and wine refrigerators, and twin Sub-Zero refrigerators in the basement providing generous additional cold storage. A drop freezer, water softener, bar sink filtration, high-capacity range hood, Vermont Castings wood stove, and split system in the office enhance comfort and functionality. Outdoors, a newly constructed gunite pool by Scott Pools is surrounded by an expansive granite patio with upgraded coping that remains cool underfoot. The pool features dual heaters, swim shelf, swim-out step, discreet lap lane, and premium cover. In spring, the lawn will be refreshed and the pool area styled with elegant furnishings, oversized planters, and Tucci umbrellas. The land itself offers rolling fields, woodland trails, fruit trees, and a fenced apiary with mature beehives. With generous road frontage and multiple driveway access points, the property provides enhanced privacy and flexibility. Raised-bed vegetable and herb gardens near the kitchen reinforce a lifestyle rooted in beauty, sustainability, and abundance. Additional amenities include a twenty-four by twelve garden shed, Level Two EV charger, Goshen-stone patios and walkways, a CeDur roof, and buried 400-amp electrical service. Security and Nest systems with cameras are in place for peace of mind. Despite its serene setting, the property is conveniently located to Albany, Troy, Saratoga Springs, Hudson, Chatham, Rhinebeck, Lenox, and Stockbridge, offering access to dining, culture, boutiques, and year-round recreation. Whether hosting gatherings or savoring solitude amid open land and endless views, this exceptional estate offers a rare and deeply satisfying way of living.

DEEP ACRES - The embodiment of timeless elegance and refined country living in an unparalleled setting. Nestled in the rolling farmland of Columbia County, in New York's Hudson Valley, Deep Acres is a singular estate blending the grace of an English country manor with the tranquility of pastoral landscapes. Spanning 293-acres across six meticulously maintained parcels, the property blends rolling hayfields with formal gardens, offering unobstructed vistas to the Catskill Mountains, dramatic sunsets and a lifestyle rooted in beauty, craftmanship and serenity. A tree lined drive leads to the stately 4,900 SF Greek Revival manor home where classic architecture meets stately elegance. Adjacent sits a heated three-car garage complete with a 1.200 SF second floor office apartment and a spacious parking court. Entering the home, you will experience some of the finest craftmanship, curated lighting and architectural detailing. The entrance foyer, with a grand staircase to the second floor, is flanked by a Mahogany paneled library and a sunlit breakfast room. Further, is the formal salon and dining room which extend onto a deep southern-style covered sitting porch with views of the far-reaching meadows and Catskill range beyond. The chef's kitchen is designed for effortless entertaining while remaining intimate enough for everyday living. Just beyond the kitchen is a service entrance with access to a private one-bedroom apartment above. Upstairs, the primary en-suite is joined by two additional en-suite bedrooms and a richly paneled home office which connects to a third-floor studio with panoramic views. The finished lower level includes a gym, a fully appointed laundry, a second pantry, a cedar lined walk-in closet and the home's mechanical systems. Every floor is serviced by an in-home elevator. Formal gardens and secret gardens are a masterclass in landscape design and laid out to elicit curiosity and showcase the season's full vibrancy of color, while the surrounding hayfields offer a timeless rural counterpoint. Cool off in the pool or dine al fresco at the pool pavilion - an historic barn transformed into an inviting retreat complete with changing room, full bath, kitchenette and garden room. The second floor of this original timber framed structure offers space for one's future vision. Nearby, is the head house garden complex with gardener's office, workroom, garage and glass conservatory, imported from England - all supporting the estate's fenced in perennial/vegetable garden. Further down a gravel lane is a private two-story 2,900 SF guest house/caretaker's cottage renovated into a 3-bedroom, 2-1/2 bath home, perfect for family or on-site management. A few of the property highlights include a 35-zone irrigation system, landscape lighting showcasing the arboretum quality plantings, multiple back-up generators, high speed internet and connectivity and a property security system. Deep Acres is a rare and complete estate, timeless in its design and masterful in its execution. A Hudson Valley treasure, ready to be experienced.