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$1,395,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192284 MLS
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury
$1,076,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193014 MLS
Rare Bethlehem Offering - 1740s Antique + Commercial-Ready Barn on 2 Acres Welcome to a rare offering in the heart of Bethlehem, CT, sited at the town's famous blinking light with easy proximity to Washington, Litchfield & Woodbury. Dating to the 1740s, this sensitively preserved 4-bedroom antique is rich with period charm - 5 fireplaces, including a 12' hearth housing a beehive oven, historic detailing, a walk-up attic, and a basement with soaring 9' ceilings. Thoughtful updates throughout make it a warm, move-in-ready home. The real story here is the barn: a striking 3,000 SF structure originally restored for a commercial dine in bakery, with the significant investment already behind it - new roof, doors meeting fire & code, 4-phase electrical, roughed plumbing & HVAC, and poured concrete floors. Reimagine it as an event space, artisan workshop, wellness retreat, or second residence - the foundation is already in place. A picturesque pond adds ambiance, ideal for commercial use or connecting the structures for potential multi-generational living. A charming milk house offers even more flexible space - guest quarters, studio, gym, or workshop. Grounds feature ornamental Japanese & red maples, flowering pear, cherry, birch & magnolia, plus a newly graded and re-graveled driveway (2023) and 75 feet of town-maintained sidewalk! A rare chance to own a piece of Bethlehem's history - the work is already done.

18 East St, Bethlehem
$398,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24186179 MLS
Warm and welcoming, this vintage home with a classic rocking chair front porch is ideally located within walking distance of Woodbury's town center. Beautifully maintained, it blends timeless character with thoughtful updates throughout. A gracious foyer with hardwood floors and a wall of closets provides exceptional storage. The living room features hardwood floors, built-in shelving, and an electric fireplace, while the dining room showcases a classic built-in cupboard. The updated country kitchen offers Vermont soapstone countertops and new flooring, and a convenient main-level laundry room with a half bath completes the first floor. Upstairs are three bedrooms and a full bath. Energy-efficient improvements include newer windows and doors, along with individual thermostats in every room for personalized comfort. An enclosed rear porch provides the perfect mudroom or everyday entry. Outside, the level backyard has been transformed into a park-like retreat with a new patio, attractive landscaping, and plenty of space for entertaining, gardening, or simply relaxing. A shed provides additional outdoor storage. Located in Woodbury, named Reader's Digest's "Most Charming Small Town" three times, this home offers easy access to restaurants, galleries, cultural venues, day spas, hiking trails, ski areas, wineries, and equestrian facilities. Approximately 90 minutes from Manhattan, it offers the perfect blend of small-town charm and convenience. Seller reviewing offers.

9 Spring St, Woodbury
$749,900
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190540 MLS
Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and nearby hiking trails. Inside, hardwood floors and abundant natural light create a warm and inviting atmosphere. The welcoming living room features a fireplace, while the bright south-facing sunroom provides a relaxing space to enjoy throughout the day. The dining room includes a charming corner cupboard that adds timeless New England character. The finished lower level offers flexible space for exercise, hobbies, or creative pursuits and includes a sauna, shower, and fully equipped darkroom. Additional highlights include a two-car garage and beautifully landscaped outdoor spaces. A rare opportunity to enjoy distinctive features, exceptional charm, and an ideal in-town location in one of Litchfield County's most desirable communities.

31 Mountain Rd, Woodbury
$650,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24183597 MLS
Charming in-town Gambrel Colonial with views of Orenaug Pond, located just up the road from the South Green. Surrounded by historic landmarks such as King Solomon's Lodge, the Hurd House, the Glebe House, and other notable properties, this home offers three bedrooms, three full baths, and one half bath. It also features a remodeled kitchen with stainless appliances that opens to a family room with vaulted ceilings. Additional highlights include a partially finished walk-out basement, an attached two-car garage, an oversized deck, and private yard. Close to parks, private schools, tennis and swim clubs, shopping and more. Come fall in love with Woodbury.

30 Park Rd, Woodbury
$2,995,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24163576 MLS
Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury
$649,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24177873 MLS
Fantastic Potential in this home. Three bedroom Cape Cod sitting on 5.50 acre lot with a giant barn that has great potential living space to convert into an in-laws set up, office, studio space or music studio to fit your lifestyle. Home freshly painted interior and exterior. Renovated kitchen with all new countertops and Italian farmhouse sink, floors, Pantry, refreshed cabinets. All newer energy star appliances. Updated bathrooms- new vanities, tile, floor, and walk-in shower in upstairs bath. Walk out into your large screened in porch to enjoy the beautiful quiet and nature surrounding you in your lovely home. Giving you a peaceful retreat. New roof 2022. New heat pump hot water heater 2022 . New water holding tank 2025. Mini Splits installed in 2020. Entire house water filtration system. New cast iron woodstove installed in 2021 with refaced fireplace. Lots of space to run and play. Private hiking and biking trails with a campsite at the top of the property complete with fire pit. Grow a Beautiful garden of vegetables, with pretty flowers and flowering trees surrounding you. The lot is large enough for poultry or livestock for those of you with Love of animals? The two car garage has electric car outlet. 9.8 kW Solar array installed 2020.Seller owned Solar panels on the property for those energy saving consumers. So much potential, so much to see, schedule your tour soon!

16 Cross Brook Rd, Woodbury
$1,900
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24173384 MLS
Apartment 5 is a large, bright, natural light filled apartment. Second floor with front and back private porches. Living room is very spacious with built ins. Kitchen has granite counters and two pantries. Hard wood flooring. Brand new appliances in laundry room. Freshly painted - Ready for immediate occupancy. This is a second floor unit. Rear yard is recently cleared and seeded for all tenants to enjoy. Square footage is approximate. Preference is no pets, but will discuss on case by case basis.

4-5 Weekeepeemee Rd Unit 5, Woodbury
$895,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172742 MLS
Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.

253 Bacon Pond Rd, Woodbury
$289,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24162115 MLS ⋅ Condos At Woodlake BLDG.
Welcome to this well-maintained condo offering comfortable living in a desirable Woodbury location. This inviting unit features a bright and open layout with spacious living areas, an updated kitchen, and generously sized bedrooms. Enjoy the ample storage and a private outdoor space perfect for relaxing or entertaining. Nestled in a quiet, well-kept complex close to local shops, dining, and major routes, this home offers a perfect blend of comfort, convenience, and low-maintenance living.

3 Tamarack Ln Unit 3, Woodbury
$699,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24139265 MLS
This authentic antique home is ideally located on one of Bethlehem's most desirable country roads, surrounded by other elegant historic properties. Meticulously maintained, it showcases true period charm with spacious rooms, high ceilings, original wide-board floors throughout, and a grand central chimney serving three fireplaces. The main level is perfect for both daily living and entertaining, featuring a large eat-in kitchen, a cozy wood-paneled study with built-in bookcases and fireplace, an inviting living room with fireplace, and a gracious formal dining room-all generously proportioned for comfortable gatherings. Upstairs you'll find three well-sized bedrooms, a full bathroom, a large walk-in attic over the kitchen that's already framed and ready to become a luxurious primary suite, plus a separate walk-up attic with plenty of headroom for additional finished space. The beautifully landscaped grounds include a sweeping level lawn, a fully approved extra building lot with its own private driveway, and a handsome post-and-beam barn offering ample room for vehicles, workshop space, and storage. Move right in and enjoy this classic beauty as-is, or take advantage of the rare opportunity to expand, add a guest house, or create a family compound.

114 Carmel Hill Rd N, Bethlehem

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