Pleasant Valley NY Real Estate & Homes for Sale

Stunning Colonial nestled on a beautiful 7.88 acres on a quiet country road, make this your year round home or weekend retreat. As you enter the home from the rocking chair front porch you enter the tiled foyer, then walk into family rm w/Cathedral ceiling, a wood burning stove and access to the oversized deck. Kitchen has granite counter tops, Sub-zero Refrigerator/Freezer, Thermidor double oven, 6 burner gas cook top w/vented hood. 1st floor primary bedroom w/primary bath & walk in closet. Formal dining and living rm, Powder rm and laundry rm & door to salt water heated pool, Hot tub great for entertainment. Second floor has 3 bedrooms w/one ensuite and 1 additional full bathroom. Office with walk up access to the full attic. In the basement you will find the Family rm with surround sound / a Jotul gas stove & additional full bath. Interior access to the large 2 car heated garage w/pellet stove along with a ceiling mounted Modine Heater that runs off the furnace. Mature plantings, large garden and shed. 14 Little Pond is a Town of Pawling maintained road. This home has a generator hook up, You are close to Metro North, Golf courses, Rail trails, Appalachian Trail, restaurants, shopping. There is plenty to enjoy in Hudson Valley. Your private oasis awaits you.

Welcome to your dream farm retreat nestled in the picturesque foothills of the Berkshire mountains! This sprawling property spans just under 175-acres with a rich history, once serving as a prominent dairy farm and now flourishing as a horse farm. Here, you will find a stunning array of farm buildings, lush pastures, paddocks, a sprawling pond and acres of wooded mountainside. The main residence, a classic center hall colonial, offers grandness and comfort with its 5-bedrooms and 4.5-bathrooms. The charming interior is adorned with 4 fireplaces, wide plank pine flooring and a spacious layout perfect for entertaining. Admire the beauty of the landscape from the inviting wrap-around porch or take a dip in the refreshing in-ground pool. Adjacent to the main house, a large carriage house provides additional living space for possible tenants with a first floor 4-bedroom apartment and a second floor 1-bedroom apartment, accompanied by an attached 2-car garage. A quaint one-bedroom cottage tucked away on the property offers even more accommodation options. The farm itself features a vast array of well maintained barns adorned with multiple cupolas. The main barn includes ten 12'x14' horse stalls, private office space and an extensive second floor area with multiple options for its use. Outside, you'll find three paddocks, a round pen, four silos and several large and small storage sheds ensuring ample space for all your farming needs.

West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open meadow, and serene pond. Spacious rooms perfect for entertaining include a great room with a soaring peaked ceiling and a 20' stone fireplace, sun-filled formal dining room with three exposures, huge Chef's kitchen with a massive stone fireplace and adjoining catering kitchen. Beautiful reclaimed chestnut floors, exquisite detailing and banks of windows and French doors. The paneled library, office and master bedroom suite are located on the first floor in a private wing of the house. Billiard room, complete with mini-kitchen, full bath and adjoining guest bedroom. Second-floor master guest room with soaking tub and deck with views. Two bedroom suites with ensuite bathrooms, charming children's bedroom and an office complete this floor. Lower level with a media room, half-bath, wine tasting room and wine cellar with adjoining prep kitchen. Laundry room, craft room and gym. Beautiful stone steps lead to a stunning pool & pool house with full kitchen & tennis court. Two building maintenance court contains a pumping system for irrigating the lawns and gardens.

A truly rare opportunity to own "Dragonfly Farm", one of the most unique estates in New England which has been featured in House & Garden and many architectural books. The estate compound began in the 1700s with the construction of the mill and the millkeeper's house (which now serves as the guest house). The Federal style stone house was added to the property in the early 19th century. In the 20th century, this main house was expanded by owner and architect Heathcote Woolsey. It was then owned by the Hammerstein family (of Rogers & Hammerstein fame). The current compound includes the 5 bedroom residence, 2 bedroom guest house, antique barn, office/gym/game room complex above the 4+ car garage, caretaker's house and a stone cabana. Unique features of the main house include a gracious foyer w/ curving staircase, dining room w/ opposing fireplaces, vaulted kitchen w/ stone walls/opposing fireplaces/hand hewn beams & a stunning solarium/family room. Leisure time will find you enjoying tennis, soccer, basketball, golf chipping, archery & the gunite heated pool.

Welcome to 333 Kent Rd. This is a beautiful opportunity to own a mixed-use property in Kent featuring two fully rented units and a 120-seat restaurant with an updated kitchen and full bar on the main level. The possibilities are endless. Bring your imagination. This property has been wonderfully maintained by the current owner. Located across the street from Bulls Bridge, a well-known covered bridge, as well the Appalachian Trail. Hiking, biking, and nature are just across the street! Located in the picturesque town of Kent Ct, just south of the center of town, boasting high-end stores, restaurants, and boutiques. Let your imagination run wild with all the possibilities!

Two lots being sold together- included in the sale of 59 Fuller Mt. is 61 Fuller Mt with an additional .92 acres and additional taxes of $1489.00. Build your dream house, just 5 minutes from Macedonia State Park for hiking, biking , fishing ,etc. Minutes from Kent town center.

Privately set, on a near 2 acre lot, with inground pool, spa & cabana, in Sherman's premier golf community, this grand 6500+ SF plan showcases 9 ft & vaulted ceilings, Mahogany floors throughout, 4 fireplaces & more! A grand foyer with circular stair, herringbone mahogany floors & dramatic lighting creates an impressive entry. Framed by a classic formal dining room & living room with mantled fireplaces, built ins & quality trim exudes elegance. Gather in the Chef's kitchen with marble counters, center island plus a breakfast bar & a spacious dining area leading to the Trex deck & an enticing IG Pool with slide and cabana! The kitchen is open to the vaulted family room, with floor to ceiling stone fireplace, the same gorgeous hardwood floors & French doors to the Trex deck and lushly landscaped yard. Views of the pool & private yard are also seen from the main level owner's suite, with spa bath, double sinks, jetted tub & marble tile. An exciting upper level with wrap balcony showcases 3 spacious bedrooms with full baths, ceiling fans & lots of closet space plus a cozy loft for reading or relaxation & an adjacent private office. A spacious bonus room over the 3 car garage is ideal for game room, bunk room or extended guest stays. Manicured grounds, gunite pool, stone patio, cabana w/full bath & outdoor shower, 3 car gar & more The Club at River Oaks offers golf & social memberships (optional),clubhouse, pool, gym, restaurant, bar & pro shop! Not to be missed!

Privately tucked away on 5+ Acres - an exceptional opportunity awaits the savvy buyer to create their own personal retreat in the small town of Sherman. Sophisticated New Construction, open-concept design and incomparable craftsmanship to be built by SHERMAN BUILDING DESIGN, hands on Architecture/Builder. This Modern Barn floor plan caters to the active and evolving needs of today's busy life styles and diverse contemporary life stages. You will love the elements that are available that compromise the clean lines, modern features and warm essence of your new home. Tailor plans with unlimited aesthetic & material options available based on your needs. $ TBD with budget of $400 per sq ft. Ease & proximity 5M-Metro North Train Station/5M-quaint small Town Center, Community Park w/Basketball, Tennis & Pickle Ball Courts, jogging path/Town Boat Slips/Kayak-Canoe Racks & Sandy Beach on CANDLEWOOD LAKE/2M to private golf club (The Club @ River Oaks) / 3.5M to Quaker Hill Country Club. 6M to 835 Acres Deer Pond Farm Sanctuary-Audubon Center w/its 20M of trails. 60M to NYC-makes for a perfect weekend retreat or year round living. Welcome to Small Town USA! Builder available to meet and walk land.

Craft your dream home from the ground up with this rare built-to-suit offering set on a sprawling 5.46 acre lot on Long River Road in River Oaks Country Club, a private gated golf course community in Sherman, CT. This 4 bd / 4.5 bath / 3,759 sq.ft. open-concept residence with main level master seamlessly connects a chef's kitchen (w/ pantry) to an elegant dining area and a living room w/ cozy fireplace. Elevate outdoor gatherings on the sun-drenched patio with sweeping long views (optional POOL can be added). Club River Oaks features an 18-hole, par-70 golf course that blends with the natural terrain of the Berkshire foothills. Enjoy amenities like tennis courts, heated swimming pool, fitness facilities, fine or casual dining, Golf Pro for private lessons and summer golf camp for kids. Various membership options are available. Situated just 60 miles from NYC, 45 miles from WHITE PLAINS, this prime location allows easy commuting. The charming town center, 5 min away, offers community amenities: a library, parks, pavilion, sandy beach, and town boat slips on Candlewood Lake. Nearby catch & release trout fishing, acres of hiking & biking trails + skiing at Mohawk Mountain. Sherman is known for low taxes and excellent PK-8 school, making this location a rare gem. Pictures are for reference, home is TO BE BUILT and FULLY CUSTOMIZABLE. Don't miss the chance to customize an exceptional property where every detail mirrors your unique taste and individuality. Land only MLS 170615535

New Home proposed to be custom built to the wants and needs of the contract purchaser on this beautiful lot in St. John's Peak. Pricing is based on a 2 story 3300 square foot house size. Final price, house plan and specifications to be agreed upon between buyer and builder. Home to be built by Multi Award Winning Litchfield county builders Ground Breakers. Builder has built several homes in the subdivision as well as many other homes in CT. Lot has been cleared and all engineering data has been updated to move forward as soon as plans and specs are finalized. Financing if necessary to be a construction to perm mortgage. Photos are an example of homes built by Ground Breakers and are not necessarily what is proposed in this home listing. Taxes based on land only.

Surrounded by breathtaking panoramic views, this newley home offers the ultimate retreat for golf enthusiasts. This single-level residence in the prestigious community of Club River Oaks boasts a variety of amenities tailored to enhance your experience. The generous gourmet kitchen provides the perfect setting for post-game gatherings. Unwind in the open-concept, spacious living areas, where a cozy fireplace and gorgeous views offer the ideal backdrop for relaxation and camaraderie. The main level primary bedroom is designed for comfort with two walk-in closets and a generous bathroom, complete with standing soaking tub. The sprawling deck enhances the allure of this home with lush views of the gently rolling fairway. With direct access to the golf course, every day is an opportunity to hone your skills and indulge in the sport you love. Club River Oaks features an 18-hole, par-70 golf course and amenities include tennis courts, a heated swimming pool, fitness facilities, and dining options ranging from fine to casual. The club also provides access to a Golf Pro for private lessons and hosts a summer golf camp for kids. With various membership options available, there's something for everyone. This is an unparalleled location. Enjoy boating on nearby Candlewood Lake, fly fishing on the Housatonic, and hiking on the Appalachian Trail, all just minutes away from your piece of paradise. This residence offers the perfect blend of tranquility and convenience at your doorstep

READY FOR IMMEDIATE OCCUPANCY!! Look forward to spring in Connecticut with views of the Litchfield Hills. Contemporary farm house on beautiful lot located in the Club at River Oaks in Sherman, Connecticut. Located in the rolling hills of Litchfield County, the Club at River Oaks has a signature 18 hole golf course, beautiful club house with a full service bar, gourmet restaurant. tennis courts and a pool. A socail membership entitles you to all the amenities you could hope for, an additional fee allows golf course membership as well. The contemporary farm house has an open floor plan, 9+ ceilings on the first floor, hardwood floors throughout and a gourmet kitchen. Gated community call for access.

Welcome to The Club at River Oaks in beautiful Sherman Connecticut. Wonderful golf course lot. Beautiful 5 bedroom custom home. Hardwood floors through out. Gourmet kitchen with granite counter tops. Deck overlooking the golf course. Social membership entitles you to all the amenities you could hope for. Nestled in the picturesque Litchfield Hills. Spend your days playing tennis and then take a dip in the pool Beautiful club house with full service bar and gourmet restaurant. Outdoor dining on the patio overlooking the signature 18 hole golf course. Use of golf course to additional membership fee. World class fly fishing in the Housatonic River just steps away. Enjoy boating water-skiing and swimming on nearby Lake Candlewood. Live in a vacation area year round, easy commute to NYC. Agent related to builder.

Step into tranquility with this fully renovated Mid-Century gem tucked away on a private drive. Nestled on 5 acres of wooded bliss, this home offers the perfect blend of privacy and nature. Enjoy the serene surroundings from your brand new deck and porch, where every sunset feels like a moment of pure magic. With a finished basement offering additional space for entertainment or relaxation, this home is a true sanctuary for those seeking tranquility and style. Welcome home to your peaceful retreat.

Country Compound With Commanding Views - Landmark Property, impeccably maintained and renovated with stunning mountain views over farmland. Drive into this gated estate to find the view and setting nothing short of magical. Stone walls, terraces, and perennial gardens make this the quintessential New England country estate. The main house has nearly 10-foot ceilings on both floors, beautiful antique hardwood floors, a chef's kitchen, 5 wood-burning fireplaces, and a 1000+ bottle wine cellar. A sophisticated renovation to please the most discriminating buyer. As if that isn't enough, there is a 3,500 sq ft Carriage house with guest quarters/office, a caretaker's or rental apartment, and a cabana for the heated gunite pool with gym, kitchenette, full bath, and changing room. Just over an hour from Manhattan makes this the perfect getaway or full-time residence.

Built in 1846, this meticulously renovated four-bedroom Colonial seamlessly blends modern amenities with historic charm. The kitchen offers a gorgeous center island with seating, elegant black granite countertops, a farmhouse kitchen sink, and white custom cabinetry. Attached to the kitchen is a covered, screened porch that offers a retreat-like feel with picturesque views of the landscaped grounds and gardens. Adjacent to the kitchen is a versatile office/craft space as well as a formal dining area with fireplace. The main level also features a sunlit living room with built-in shelves, and a library with cozy fireplace. Upstairs, a spacious primary bedroom is accompanied by two additional bedrooms, sharing a luxurious white marble bathroom with soaking tub. The property includes a detached two-car garage, backup generator, and a beautifully designed bluestone sitting area with a large fire pit, perfect for hosting gatherings with friends.

Outstanding Colonial Farmhouse on a peaceful secluded lot-enjoy your summer relaxing on your front porch overlooking the manicured grounds, dining on the multi-level decking or taking a dip in your private pool. This special home was built in 2002 and features newer hardwood flooring throughout the main level, an open eat-in kitchen with breakfast nook, bright and cozy dining and living room with wood burning fireplace, plus a convenient powder room and easy access to the roomy two car garage. The upper level has a stunning primary suite with cathedral ceiling and large windows, plus dual closets and a full bathroom. There are two additional spacious bedrooms and another full bath on this level as well. Downstairs offers tremendous space and potential with a huge partially finished bonus room that walks out to the back yard, plus loads of storage space. Updated mechanicals, including a new water heater and water filtration system. The yard is an outdoor-lovers dream, privately set back from the road with mature flowering trees and perennial gardens. So many places to relax or entertain. All situated just minutes to shopping, restaurants, New Milford's charming downtown, Route 7 and Route 55 for an easy NY commute. A truly special home, just move in and enjoy the summer in your own little oasis.

Totally Private Top of the World Setting with Monster Catskill Views. 10-Min to the Center of Millerton NY/Sharon CT & 15-Min to Metro North Train. Graciously Scaled Rooms Throughout. 4 Fireplaces. The Ultimate Swimming Pool & Pool Area Complete with: Hot Tub; Outdoor Kitchen; Fireplace & Large Stone Terrace. Tennis Court. 3-Car+ Attached Garaging. 6 Paddocks with Run-In Sheds + Riding Ring & Barn. BIG Value for the Dollar!

Great curb appeal! 3 bedroom raised ranch on beautiful 1 acre lot in quiet Gaylordsville. Vaulted, granite center island kitchen with maple cabinets. Dinig area with clider to private deck. Vaulted living room with bow window. Newer engineered laminate/hardwood floors throughout. Lower level level family room with fireplace/wood stove. Oversized garage. Central air. Large shed. Priced to sell!!

Very Special & Architecturally Significant Home just off Cobble Road in Kent and featured in the NY Times: 4 bedrooms, 4.5 baths, room to spread out, and full of natural light. With just over 2 acres and open views, this wonderfully maintained Frank Lloyd Wright-inspired home sits on Cobble Heights Road about 5 minutes from downtown Kent. Built for entertaining and a floor plan that creates privacy and separation within the home. Terrific location, with convenience to NYC via Metro North (20 minutes to Harlem Valley Wingdale). If hiking is your thing, trails abound including Kent Falls State Park, and the town of Kent is one of the more sought-after in Litchfield County, with many highly rated restaurants and shopping options. Less than two hours to NYC but a world away in bucolic Litchfield County.

Originally constructed in 1739, this delightful Antique is nestled in Kent's picturesque Flanders Historic District, right along scenic Cobble Road. Steeped in history, the home boasts many original features, from its wide board floors to the central chimney that serves two fireplaces in the living and dining rooms, not to mention the charming hand-hewn beams overhead. Meticulously maintained, the original house has undergone a thoughtful expansion, creating a generous open-concept space that seamlessly blends a modern kitchen with high-end stainless steel appliances and butcher block counters, flowing into a sun-drenched dining area and seating area adorned with custom built-in bookcases. Venture upstairs to discover the primary bedroom with its luxurious en suite bathroom, flanked by two additional bedrooms sharing a bath. The walk-out lower level offers a versatile large room that could easily serve as an overflow bedroom, accompanied by a full bath. The property also features a grand party barn and a separate studio, adding an extra living space ideal for a home office or a future guest home. Outside, the 2.4-acre property borders Cobble Brook and showcases a serene pond, enchanting vegetable and flower gardens, a charming grape arbor, and a fruitful orchard, creating an absolutely idyllic setting.

Private waterfront pied a terre with direct water access on Spring Lake just outside of Rhinebeck, NY, this is a rare find. Hot tub. Grandfathered deck allows for basking right on the water. Large screened in porch. Open plan, good natural light, ideal weekender within the private East Lake community. Available immediately to start enjoying the approach of spring and summer.

Uninterrupted VIEWS and privacy, protected by land trusts / conservancy on 50+ acres in South Kent! Superbly located on a town maintained, scenic road surrounded by established country estates. Incredible opportunity to expand the existing 3 bed cottage or use it as a guest house and build your dream home on a higher elevation to capture further views and magnificent sunsets! The property abuts Long Mountain-Mud Pond Preserve which is a 400 acre network of conservancy lands. The unique features of this land include level areas for a lawn and swimming pool, multiple sites for a new / additional house, trails through the trees, stone walls, gently sloping hills, a Large Barn and direct waterfront access to Mud Pond. Opportunity to sub-divide or enjoy tax advantages by donating part of the acreage to a Land Trust, thus ensuring unspoiled views for generations. Located only a few minutes drive south of the picturesque village of Kent for galleries, restaurants, shops, etc. This property presents opportunities to subdivide & consists of two lots: 39.36 acres in Kent; 12.5 acres in New Milford. Easy access to NYC via rte 22 and Wingdale train station. The land is steeped in history, having previously been owned by one family for several generations. In the past, part of the land was used for night pastures and the property has been discussed in detail by Adam Halasi Kun in his book entitled "The Unknown Right."

A remarkable opportunity to own and renovate a home across from Sharon Hospital in the Village of Sharon, Ct. This home is in the center of Sharon and all that offers, such as the restaurants, library, hospital and all the associated doctor's offices. This home is served with both Town water and sewer and is minutes away from the train station to NYC.

Charming Cape in Ideal Location - This lovely Cape Cod home located on an amazing lot in idyllic Sharon CT is now available for sale. Cross the threshold of the extra deep wrap-around porch and enter the home with hardwood floors and generous proportions. The light-filled kitchen has a dining area with a large bay of bowed windows overlooking the side yard. A laundry room/mudroom is adjacent. The living room features an extra large double-height stone fireplace that has doors to a heated sunroom with wrap-around windows and access to the back patio with gorgeous views. The main floor primary bedroom has its own stone fireplace, a private sunroom, an en-suite bath, and ample closet space. Ascend to the second floor to discover two guest bedrooms and a full bath, providing comfortable accommodations for family or visitors. A detached two-car garage with loft storage space accompanies the property, featuring an attached room housing an exercise pool, perfect for relaxation and fitness. Enjoy the peaceful ambiance of country living, with convenient proximity to local amenities including in-town shopping, the Sharon Playhouse, Indian Mountain School, Hotchkiss School, and easy access to NYC train transportation. Don't miss the opportunity to make this tranquil retreat your own.