Woodbury Homes with Historic Antique Style

Welcome to Woodbury, Connecticut – a hidden gem nestled in the heart of Litchfield County. Known for its rich history and picturesque landscapes, Woodbury is a charming town that seamlessly blends the old with the new. With its quaint main street lined with boutique shops, delightful eateries, and a vibrant arts scene, it’s no wonder that this community is a favorite among those seeking a serene yet engaging lifestyle.

One of the most captivating aspects of Woodbury is its collection of historic homes, many of which boast exquisite antique styles that tell the stories of generations past. These homes, often adorned with original woodwork, classic moldings, and period-appropriate details, offer a unique glimpse into the architectural heritage of New England. Imagine living in a beautifully restored colonial or a stately Victorian, where every corner whispers tales of yesteryear.

The charm of Woodbury extends beyond its homes; the town is surrounded by lush greenery, scenic parks, and an array of outdoor activities. Whether you enjoy hiking, biking, or simply taking leisurely strolls through the historic districts, there’s something for everyone to enjoy.

Families are drawn to Woodbury not only for its stunning properties but also for its top-rated schools and a strong sense of community. With a welcoming atmosphere and an abundance of local events throughout the year, residents find a true sense of belonging here.

If you’re in the market for a home that combines historic elegance with modern comforts, Woodbury is the perfect place to call home. Discover the beauty and charm of this enchanting town, where history and community thrive in perfect harmony.

Newest Woodbury Homes with Historic Antique Style

$959,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188039 MLS

Timeless Elegance & Immaculate Detail. Welcome to The Naramore House, a piece of living history. Lovingly preserved since 1898, this pristine colonial home seamlessly blends grand historic character with immaculate, turnkey maintenance. A classic wraparound front porch invites you through a charming dutch door into a formal, stately foyer featuring high ceilings and original pocket doors. The massive living room serves as the heart of the home, offering incredible square footage for multiple seating arrangements, media setups, and a cozy fireplace. Host effortlessly in the grand formal dining room and eat-in kitchen, complete with a generous pantry, a charming secondary rear staircase, and screened in sun porch. A luxurious primary retreat featuring a fireplace, private en-suite bath and massive 10x7 foot closet/dressing room. Three additional bright and spacious bedrooms include a versatile room-ideal for a dedicated home office, nursery, or library. The home has a huge attic with potential for expansion. A private patio, stunning formal garden with pagoda and mature trees offer the perfect setting for outdoor enjoyment. A recently renovated barn includes new structural beans and flooring. This lovely home offers in town conveniences like walking to restaurants, shops and local parades while set off of Main Street. Enjoy the beautiful historic architecture with the peace of mind that comes from a property that has been meticulously cared for inside and out.

11 Pleasant St, Woodbury

$850,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$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

$775,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24138386 MLS

The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

28 School St, 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

$1,790,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24136657 MLS

Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury

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