Winchester CT Real Estate & Homes for Sale

Rarely does such an opportunity present itself in one of the most sought-after locations in Litchfield County, bucolic Cornwall, CT's Cream Hill Lake region. This magical 1921 center stair colonial is a mere one hundred and one years old, and is just steps to Cream Hill Lake and its public / private beach club. The house is a sprawling five bedroom, three and a half bath home well loved by the same family for more than forty years. A massive field stone fireplace anchors the living room, and the rambling semi open floor plan creates innumerable moments for quiet places to sit and sip a drink or read a book. The guest wing addition doubles as a second primary suite or studio office and has views of the Cream Hill Valley facing south. Mature gardens, including a massive natural stone garden of CT granite, and dozens of mature trees and shrubs encouraged over the generations make each day a moment to observe nature in all its glory. There is an ample barn, storage for four cars, and a cottage on the upper property which if restored would create an adorable guest house, like something out of an English fairy tale. There is a certified pool site.

Amazing opportunity! Attention all builders and contractors - bring this unique classic beauty back to life. Majestically set on 1.74 acres of level park like property with potential for subdivision. The home has many special unique features like original pumpkin pine paneling in living room, original fireplaces, etc.. This home and property has really too many possibilities to list!!!. In addition, this property was also the original site for the Hollywood Classic Movie Museum which is now in Plainville Ct. The sale excludes the "playhouse/shed" Which will be removed prior to the sale.

This picturesque custom home underwent an extensive renovation and expansion. The property features a main house and custom barn/heated workshop. Upon entering, you're immediately welcomed into a grand, two-story great-room that seamlessly connects to a spacious chef's kitchen. The kitchen boasts handcrafted cabinetry, a soapstone farm sink and countertops, stunning vaulted ceilings and high-end commercial-grade appliances. The barn trusses, wide plank oak floors, and a brick fireplace enhance the rustic elegance of the home. Off the kitchen is a sliding 12 ft. glass door that opens to a covered/enclosed 3-season sunporch with an outdoor living and kitchen area. The west wing of the house accommodates two bedrooms, including a first-floor Primary suite with a wood-burning fireplace, a large walk-in closet, and a full bath. A second bedroom and a full bath/laundry room area complete this wing. Large bonus room/bedroom, currently being used as an office, is conveniently located on your second level. The lower level offers a partially finished family room and an additional bedroom space with a full bath. The property is well-equipped for every season with three fireplaces, a three-bay heated garage, a newer central air system, roof, windows, and a built-in generator. Whether you're a horse enthusiast, a hobby farmer, or a culinary connoisseur, this property invites you to embrace the joys of country living along the scenic roads of the Litchfield Hills. Agent/Owner related.

Nestled in a serene neighborhood, this foreclosed property offers a unique blend of comfort and potential. Featuring 2 cozy bedrooms & 1 bathroom, built with hardwood floors. Open floor plan connects living spaces, making it ideal for gatherings & creating a spacious feel. A breezeway leads to a detached garage, offering additional storage space. Sits on a generous lot, boasting a flat & private backyard that is huge & perfect for outdoor activities or garden enthusiasts. Despite its current state, which includes a variety of personal items, this property radiates charm & possibilities for the right buyer. Please note, this property is sold in "AS IS, WHERE IS, SIGHT UNSEEN" condition without warranties. All information provided is for reference only and not guaranteed accurate or recent. Buyers are responsible for all closing costs, including tax stamps and transfer taxes, at their sole expense. It is the buyer's responsibility to verify all property info and conduct inspections before making an offer. The title will be conveyed via Quitclaim Deed or its equivalent, with no express or implied warranties of title. The buyer may purchase title insurance at their own cost. There are no inspection or financing contingencies, and the seller reserves the right to negotiate w/ bidders under their discretion. This property presents an excellent opportunity for investors or homebuyers looking for a project that they can tailor to their preferences. Don't miss your chance to transform this house into your dream home!

This is a Diamond in the Rough. Lake cottage needing some updates, but what a spot to overlook the lake from the front this home. Light and bright dining area and living room are situated in the front with some newer windows. 2/3 bedrooms with main bedroom with views. 1 bath with shower. Lake access with dock and picnic area. Lake is approximately 195 acres with a depth in the deepest area of 14'. Great lake for fishing (and ice fishing), kayaking, canoe, swimming and whatever you love to do by the water. This can only be purchased with cash because it's on leased land. Shared well with two neighbors. Septic no information. Close to Village of Millerton and Sharon, CT. Motivated Seller.....,FOUNDATION:Concrete,Piling,AboveGrade:545,FLOORING:Wood,Laminate,Cooling:Ceiling Fan,Level 1 Desc:2/3 BEDROOMS, LIVING, DINING, KITCHEN,3/4 BATH,ROOF:Asphalt Shingles

This is the home you have been waiting for! Gorgeous views out every window, beautiful sunlit rooms and plenty of space to entertain and live comfortably. Welcome to Millerton, a rural, historic setting within a short distance of a lively main street where you will find a movie theater, stores, art studios, eateries and the Harlem Valley Rail Trail. This home offers a wonderful floorplan including a spacious living room, dining room, family room and a kitchen that opens to an expansive deck. Beautiful hardwood floors flow throughout the main floor. As you make your way upstairs you will find a large primary suite with walk-in closet and en-suite bath. An additional two large bedrooms with a full bathroom as well as an additional room for an office. The home offers a full walk up attic which is perfect for additional storage. The lower level is walk out and perfect for future finished space. This home has it all!

This property in the village of Millerton presents a unique opportunity for potential homeowners or investors. With one apartment already renovated and ready for occupancy, the first floor offers immediate living space or rental income. The second floor, while requiring further renovations such as the installation of two bathrooms and a kitchen, holds the promise of becoming a cozy 1 or 2 bedroom apartment. The charm of wood floors and the benefit of recent updates like a new septic system and furnace add to the appeal. The inclusion of a garage and dedicated parking for one apartment, along with an additional driveway for the second, provides convenience for residents. Its proximity to the village center means restaurants, shops, and entertainment, such as a movie theater, are just a short walk away. Additionally, the nearby Harlem Valley Rail Trail offers outdoor enthusiasts a scenic route for walking, biking, and exploring the natural beauty of the area.

Millerton Village Investment - This Millerton Investment property is fully occupied and offers four separate rental spaces, with mixed uses for a diversified offering. Two residential units on the upper level, each spanning the length of the building and offering ample space, with covered decks for outdoor enjoyment at the back of the building. The residential units offer a 3BR and 2 BR units. The Main level offers commercial spaces, that also stretch the left and right sides of the building, provide great window exposure along Millerton's bustling sidewalks in the heart of the village.

Village Of Millerton: Business Or Residence - This light-filled building offers unlimited versatility! Two separate rooms plus a full bathroom are currently configured as a small home with a Bedroom and Kitchenette/Dining Area. The space is flooded with sunshine and offers many updates, including windows, bathroom updates, and a heat pump for heat and air conditioning. Embrace the joy of in-town living or begin your next entrepreneurial endeavor right in the heart of Millerton's village.

Unveiling, the ultimate retreat for those seeking a legal Airbnb, vacation haven, or year-round sanctuary. Prepare to be captivated by the mesmerizing melody of the Webutuck Creek as it serenades you from your own private back pea gravel patio. Set upon an expansive 4-plus-acre parcel, encompassing two lots, this Millerton gem promises an unparalleled embrace of untouched nature on both sides of the tranquil creek. Welcome to the epitome of rustic charm, (epitomized by) this timeless barn-style abode also boasts(ing) a detached 2-car garage. Step inside and be enchanted by the inviting open floor plan, where a majestic original wood-burning fireplace commands attention, setting the stage for convivial gatherings or intimate fireside retreats. Channel your inner chef in the sumptuous kitchen adorned with marbled quartz countertops, pristine white cabinets, and luxurious brass accents, all complemented by top-of-the-line stainless steel appliances. Gaze out onto the lush surroundings through expansive windows while the warm wood floors beckon you to unwind in style. Upstairs, discover two generously proportioned guest bedrooms bathed in natural light, alongside a bright full guest bathroom. But hold onto your awe because the pi ce de r sistance awaits the master ensuite, a haven boasting unobstructed vistas of the Webutuck Creek and verdant grasslands beyond. Experience year-round comfort with dedicated Mitsubishi heat pumps keeping you cozy in winter and cool in summer, while an installed universal EV charger in the garage ensures modern convenience. Additional delights include the option for an outdoor shower hookup perfect for rinsing off after a refreshing dip in the creek. Convenience meets tranquility with a large utility/laundry room on the first-floor catering to all your country house storage needs. Revel in the abundance of closet space and (revel) in a home where every detail exudes excellence and freshness. Step outside to embark on endless strolls or epic bike rides along the coveted Bronx Rail Trail, conveniently accessible just beyond your doorstep. And when it's time for a leisurely morning coffee or a delightful lunch, Millerton's charming main street beckons with its array of restaurants, shops, and upstate events. "Just a short nature walk away." Why dream of vacations when you can call this idyllic haven home? Don't miss your chance to own a slice of paradise. This is more than a home it's an invitation to live the life you've always imagined.

Step into the timeless allure of an 1890 Eyebrow Colonial a 5-bedroom, 2-bath gem that surprises with its spaciousness and boasts remarkable wide board floors. Recently separated onto 3.53 acres, this home offers ample space for gardens, pets, and children to frolic. The Metro North Wassaic station is a mere 10 miles away, granting access to the vibrant yet serene lifestyle of Eastern Dutchess County. With its character-filled interiors, this residence captures the essence of charm. Engage in countryside delights like skiing, biking, hiking, top-notch dining, and the Millerton Movie House all just a short drive away. Discover this inviting home and its location, minutes from downtown Millerton.,AboveGrade:2328,Basement:Interior Access,Cooling:Attic Fan,Ceiling Fan,EQUIPMENT:Carbon Monoxide Detector,Smoke Detectors,FLOORING:Vinyl,Wide Board,FOUNDATION:Stone,Heating:Zoned,InteriorFeatures:Electric Dryer Connection,Electric Stove Connection,Walk-In Closets,Washer Connection,Level 1 Desc:KITCHEN, FULL BATH, DINING RM, LIVING RM, DEN/OFFICE, FOYER,Level 2 Desc:5 BEDROOMS, FULL BATH, WALK-IN-CLOSETS,Level 3 Desc:UNFINISHED ATTIC,Other School:PRIVATE,OTHERROOMS:Foyer,Library/Study,ROOF:Asphalt Shingles

Discover the charm of this delightful country home, complete with a host of desirable features. Step onto the inviting front and back porches, explore the two spacious second-level bedrooms, enjoy the convenience of 1.5 baths, relax in the den or dine in the formal dining room and eat-in kitchen. The expansive living room offers ample space for gatherings, while the full usable basement and two-car garage with additional workshop or studio space provide versatility. The lush yard is a haven for gardens and pets, enhancing the country lifestyle. While the home boasts remarkable curb appeal and a rustic charm, a few updates could elevate its allure even more, although it is currently move-in ready. Conveniently located just minutes from the Metro North's Wassaic Train Station, the picturesque Harlem Valley Rail Trail, and charming towns like Millerton, Millbrook, and Sharon, CT, as well as local farm markets and stands, this property offers the perfect blend of peaceful country living and modern amenities. Immerse yourself in the country living experience by scheduling a personal viewing of this well-constructed home.

This charming country home offers a delightful blend of rural beauty and 70's comfort. Featuring three bedrooms, it exudes a timeless appeal despite its dated interior, which is in good condition and ripe for transformation with a touch of contemporary flair in 2024. Situated on a sprawling 2.8-acre lot, this property presents boundless opportunities. Whether you envision cultivating a dream garden, basking in the serene countryside ambiance, or simply relishing the vast outdoor space, this home caters to a variety of lifestyles. Conveniently accessible from Metro North's Wassaic Station and mere minutes from the Harlem Valley Rail Trail, this residence combines peaceful rural living with easy access to transportation and recreational amenities. Explore nearby farm stands, markets, State Parks, and an array of outdoor activities such as hiking, biking, skiing, and golfing amidst the untouched countryside. Discover the allure of country living with this solid home nestled on a prime piece of land.

Perched on the crest of a plateau overlooking panoramic, protected views, West Wind Hill, a bespoke country estate on 389 acres, straddles Kent, CT and Amenia, NY. Experience this truly magnificent classic stone and shingle manor house sited perfectly to experience lush sunsets and fairytale mists with the upmost in privacy. Only eight minutes from the center of Kent and less than two hours from New York City, access is via a private gated road that winds through trees, past old stonewalls with glimpses of open meadow and a serene pond. Spacious rooms perfect for entertaining include a large great room with a soaring peaked ceiling and a 20' stone fireplace, a sun-filled formal dining room with three exposures and a huge chef's kitchen with a massive stone fireplace and adjoining catering kitchen, a marble paneled powder room and mud room. Beautiful reclaimed chestnut floors, exquisite detailing and numerous banks of windows and French doors make this an unparalleled home. The master bedroom suite--which includes paneled library, separate office workspace and large bathroom and dressing areas--is located on the first floor in a private wing of the house. Of course, there is a billiard room, complete with mini-kitchen and bar, full bath and adjoining guest bedroom/office area. A second-floor master-sized guest room has a beautiful bath with soaking tub and deck that faces the amazing mountain views. Two bedroom suites with ensuite bathrooms, a charming peaked children's bedroom and a well-appointed office area complete this floor. The extensive and recently renovated lower level contains a media room with 9' screen, half bath, wine tasting room and wine cellar with adjoining prep kitchen for large gatherings. In addition, there is a sunny laundry room, craft room and gym with ground level access. Beautiful stone steps lead down to a stunning natural stone pool and a tennis court. There is also a two-story pool house with spiral staircase, full kitchen and full bath. The expansive two building maintenance court also contains a pumping system for irrigating the lawns and gardens.

This beautiful Colonial-style home is located on a serene 3-acre lot, offering picturesque views of meadows. With 4 bedrooms and 3 bathrooms (jacuzzi in the primary suite). The open floor plan seamlessly connects the kitchen and living room, creating a warm and inviting atmosphere. The living room features a cozy fireplace, perfect for chilly evenings. One of the standout features of this home is the deck off the back, providing a peaceful retreat where you can relax and enjoy the surrounding natural beauty. Take in the awe-inspiring winter mountain views! The 2-car attached garage is oversized, with a small workshop area, making it ideal for car enthusiasts or those who enjoy DIY projects. Downstairs, you'll find stunning hardwood floors that add a touch of elegance to the living spaces. Ascend the wooden staircase to the second level where wall-to-wall carpeting provides comfort and warmth. The basement level is finished and serves as a great hangout space with a bar/entertainment area, full bath and walks out to the yard. This home was built in 2003 and has been nicely sited on a mostly wooded lot, ensuring privacy and tranquility. Conveniently located, this home is just a short distance from local shopping centers, the metro north railway, restaurants, farm-to-table establishments, coffee shops, wine trails, and the Hudson Valley Rail Trail. With its spacious layout, beautiful surroundings, and convenient location, this home offers the perfect combination of comfort, privacy, and accessibility.

Situated on a 1.02 acre semi private lot this lovely ranch is the perfect place to call home. Originally built as a modular, this house has a full basement with an iron I-beam for added support. Spacious sunlit living room and dining room, updated kitchen with quartz countertops and tile backsplash, laundry room with door to expansive backyard, 3 spacious bedrooms and two bathrooms. Full unfinished basement with bilco doors offers tons of storage. The detached 2 car garage needs some work but has lots of space and a newly paved driveway. This meticulously maintained home is a must see.

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.

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. Completing the property is a large pole barn, providing even more storage or workspace for your agricultural needs. Conveniently located just 90 miles from NYC and close to the charming towns of Kent and Sharon, CT. This idyllic farm is a serene retreat within reach of urban amenities. Commuters will appreciate being just 2.1 miles from the Tenmile River Train Station, offering easy access to Metro North Railroad's Harlem Line. Enjoy breathtaking mountain views and the tranquil sounds of the rushing waters of the Webutuk Creek, which borders the western edge of the property. Don't miss your chance to own this exceptional farm in a breathtaking natural setting. Schedule your private tour today!

Needs total renovation. Bank will make make all decisions as to sale. This is a CASH SALE.

Exciting Investment Opportunity in Aminia, New York This fantastic investment opportunity awaits you, offering the flexibility to establish either a single-family home or a business on a strategically zoned property that accommodates both residential and commercial use. Benefit from the convenience of municipal town water, sewer, and pre-installed electric and plumbing infrastructure, providing a seamless foundation for your next project. Seize the chance to craft your vision on a blank canvas with over an acre of land in the charming town of Aminia, New York. Given the current trend of increasing home sales and limited inventory, you have the potential to construct your dream home in this idyllic location. Whether you're a New Yorker seeking a retreat from the city, a local resident in search of land, or a business owner eager to explore mixed-use possibilities, this is the perfect opportunity for you. Don't miss out on this wonderful chance to turn your ideas into reality!

With breathtaking views to the East over the Smithfield Valley to the Connecticut foothills, this contemporary 4 Bedroom, 2 Bathroom house is perfectly situated on one of the more scenic and bucolic stretches of land in the Hudson Valley. The home was built in 1999 and totals 2,016SF of living space. The foot print was expanded in 2018 to include a covered porch with mud room, and access to attached two car garage. The 22 acres of land feature stunning views throughout plus an easy to access elevated field that would serve as an ideal building site. The view is framed beautifully by the pond. The home is entered through a gracious mud room with ample storage and closet space. Inside, there is a large living room with a wood stove and sliding glass doors that service the very large deck overlooking the view. On the main floor there are 3 bedrooms with one full bath, plus a laundry area with washer and dryer. The kitchen is in excellent condition. Upstairs there is an additional primary bedroom with full bathroom and office en-suite. The home has been carefully maintained. There is a whole house generator.

A well cared for and maintained, ideally located 2 bedroom home with many pluses. An airy, bright and roomy eat-in kitchen with updated, abundant cabinetry is an added plus as well as a total home Generac Generator which provides for care-free living even if and when there is a power outage. A spacious outside storage shed provides storage space for lawn mower and outside gardening tools as well other items. This home is in move-in ready condition so arrange a visit so you can start packing. You won't be disappointed.

Smithfield, the picturesque locale of this residence, is embraced by rolling hills and bathed in sunlight throughout the day. Tucked away on 5 acres of unspoiled countryside, this inviting country cottage ensures both comfort and privacy. With mature trees on the North side providing a shield and a wrap-around deck accessed through sliding glass doors, the natural surroundings enhance the charm. The main living level boasts 2 bedrooms, 2 full baths, a captivating great room with a cathedral ceiling, and a striking brick fireplace. The lower level adds versatility with a spacious family room, ideal for a bed or home office, accompanied by a convenient bathroom with a shower. A one-car garage under the house and a standalone two-car garage present additional possibilities, whether for storage or conversion into a studio or workshop. Smithfield's energy and atmosphere are invigorating, while its proximity to Millerton, Amenia, Pine Plains, the Harlem Valley Rail Trail, and the Metro North's Wassaic Train Station adds convenience. The region, with its riding stables and shooting preserves nearby, captures the essence of country living. The tranquility and invigoration contribute to the allure of retreat.

Meticulously Maintained ELEVATED Log Cabin-Style home and horse barns on 19+ acres with BREATHTAKING Mountain Views. Set off a quiet country road, this stunning setting with impeccably manicured grounds captures one's attention upon arrival. One is immediately drawn to the expansive wood deck complete with built-in grill and impressive screened-in gazebo with fire-pit. This is unquestionably the perfect entertainment perch which captures the expansive long views of the valley and hillsides. Fabulous open floor plan inside, with vaulted ceilings in living room with stone fireplace, large dining area, and light and bright gourmet eat-in kitchen with high-end appliances. Primary bedroom also has vaulted ceilings, stone fireplace, and large walk-in closet leading to primary bath. Den/study off of primary bedroom. Another great entertaining space is found downstairs including a large area perfect for games, exercise or media room with kitchenette. Also downstairs is a large second bedroom and updated bathroom. 3 car heated garage with massive storage space upstairs. 45KW generator. For the horse enthusiast, the property also includes a hay barn, paddock, 4 stall horse barn & tack room, equipment sheds and arena. Great riding trails abound. This exceptional property is move-in ready and utterly magical.