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245 Hoop Pole Hill Rd, Woodbury
$750,000
24192209 MLS
An exceptional opportunity to own 76.9 acres in one of Woodbury's most desirable locations. This unique offering includes two contiguous parcels to be sold together, consisting of 14.9-acre parcel (MLS# 24192651) and this adjoining 62-acre parcel Featuring a charming 3-bedroom home, the property offers a rare combination of rolling meadows, mature woodlands, and open fields, creating endless possibilities for the next owner. Whether you're seeking a private country estate, equestrian property, family compound, recreational retreat, hunting property, or a prime development opportunity, this expansive acreage provides the flexibility to bring your vision to life. Surrounded by the natural beauty of Woodbury while offering convenient access to local amenities, this is a truly remarkable opportunity to invest in one of Litchfield County's most sought-after communities. A rare offering where privacy, scenic landscapes, and future potential come together.

245 Hoop Pole Hill Rd, Woodbury

16 Gate Post Ln, Woodbury
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 24192457 MLS
Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury

133 Painter Hill Rd, Woodbury
$395,000
24187054 MLS
Nestled along one of Woodbury's finest country roads, this exceptional 2.53-acre parcel offers a rare masterclass in privacy and natural beauty. Located just moments from the Roxbury town line, the gently rolling landscape is framed by mature trees and directly abuts the Arthur Miller Preserve and the Frank and Ellen McCort protected Land Trust. Positioned just two homes away from the historic Calder Estate, the setting creates an extraordinary sense of quietude and absolute seclusion. The property features a magnificent all-season running stream with its own natural waterfall, dramatically enhancing the native wildlife and scenic beauty of the area. Enveloped by the timeless allure of Litchfield County, this land offers an ideal canvas for an architectural masterpiece, a private weekend retreat, or a magnificent legacy estate. Its pristine setting, open spaces, and dramatic yet intimate feel provide the perfect balance of country elegance and everyday livability. Peerless privacy, a coveted location, protected surroundings, and an immediate neighborhood of significant homes make this a compelling opportunity in one of Connecticut's most desirable country settings-just minutes from the refined charm of Roxbury and Washington, and approximately 90 minutes from NYC.

133 Painter Hill Rd, Woodbury

40 Ruffin Rd, Woodbury
$1,590,000
4 Beds ⋅ 3 Baths ⋅ 24184948 MLS
It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.

40 Ruffin Rd, Woodbury

92 Minortown Rd, Woodbury
$775,000
3 Beds ⋅ 2 Baths ⋅ 24182784 MLS
Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or anyone seeking a peaceful rural lifestyle. The horse facilities include 4 barns with a total of 10 stalls, 2 wash stalls, and a 20 x 60-meter riding arena with premium stone dust and sand footing. The grounds offer ample space for turnout, training, recreation, and relaxation, creating the perfect balance of functionality and tranquility. At the heart of the property is a charming 3-bedroom, 2-bath ranch home featuring a windowed kitchen, spacious dining room for entertaining, vaulted ceilings, 2 fireplaces with wood stoves, a WIC, and an oversized lower-level bonus room. Step outside to a private backyard designed for gatherings and enjoyment, complete with a thriving vegetable garden. The 1 BR apartment is currently rented, but can easily serve as an in-law suite or guest quarters. There is also a 3 car garage for the car enthusiast! The possibilities are endless! The present owners, Serenity Farm Horse Rescue, have lovingly cared for this property for years. As their rescue continues to grow, they are seeking a larger facility to support their expansion. Shown by private appt.

92 Minortown Rd, Woodbury

1917 Main St N, Woodbury
$780,000
4 Beds ⋅ 2 Baths ⋅ 24183601 MLS
Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45' accessory building with heat - great guest house or in-law potential. Inspired by Tuscan villas, Italianate style homes, usually square and symmetrical, were popular in the late 19th C. in New England. Park-like grounds; large pond has goldfish (see pics). The 3532 square foot main home has potential for an in-home business, or retail shop as it once was. Other potential uses in this highly-visible location include using the barn for farm animals and/or horses. Home has 4 bedrooms, 2 full bathrooms, 3 fireplaces, and approx 435 sq foot foot, renovated, eat-in, sunny kitchen with leathered granite counters and stainless appliances. New oil furnace 2026. Septic recently maintained (new pump, piping, and floats in 2022 by Garrity, no problems since). 50 gallon water heater Oct 2022. Substantial moldings and built-ins, front and back staircases, specialty stainless skylights, and a rooftop belvedere, which looks beautiful lit up at night, atop the well maintained copper roof. Minutes to three towns centers of Woodbury, Watertown, and Bethlehem. Guesthouse has elec.

1917 Main St N, Woodbury

920 Main St S, Woodbury
$2,995,000
4 Beds ⋅ 6 Baths ⋅ 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

253 Bacon Pond Rd, Woodbury
$895,000
4 Beds ⋅ 3 Baths ⋅ 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

30 Hollow Rd, Woodbury
$1,395,000
5 Beds ⋅ 5 Baths ⋅ 24168618 MLS
Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury

439 Washington Rd, Woodbury
$289,000
2 Beds ⋅ 2 Baths ⋅ 24078648 MLS
Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many! Sold As-Is, Where-Is, Buyer to do all due diligence regarding potential uses, Cash or Hard Money Loan preferred, no Seller Financing.

439 Washington Rd, Woodbury

439 Washington Rd, Woodbury
$289,000
2 Baths ⋅ 24078389 MLS
Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many! Sold As-Is, Where-Is, Buyer to do all due diligence regarding potential uses, Cash or Hard Money Loan preferred, no Seller Financing.

439 Washington Rd, Woodbury

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