N/A Homes with Woodbury Middle school

Welcome to the charming town of Woodbury, Connecticut, nestled in the picturesque Litchfield County. Known for its rich history and vibrant community, Woodbury offers a unique blend of rural charm and modern convenience. With its scenic landscapes, lush greenery, and historic architecture, this town is a hidden gem for families and individuals alike.

One of the standout features of Woodbury is its exceptional school system, particularly the highly regarded Woodbury Middle School. Families seeking a nurturing educational environment will find this institution to be a cornerstone of the community. The school boasts dedicated educators, a diverse curriculum, and a strong emphasis on student development, making it an ideal choice for your children’s formative years.

In addition to its educational offerings, Woodbury is home to a variety of beautiful homes that cater to different lifestyles and preferences. From quaint historic houses to modern family residences, the real estate market here is diverse and inviting. Many properties are surrounded by stunning natural beauty, providing residents with the perfect backdrop for relaxation and outdoor activities.

The town also features a vibrant community life, with local shops, farmers' markets, and recreational parks that encourage neighborly connections. Whether you enjoy hiking, biking, or simply taking in the serene surroundings, Woodbury has something for everyone.

If you're looking for a place that combines quality education, beautiful homes, and a warm community spirit, Woodbury, CT, is the perfect destination. Come explore the possibilities and find your dream home in this idyllic setting!

Newest N/A Homes with Woodbury Middle school

$209,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24206004 MLS ⋅ Town In Country BLDG.

Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-filled unit features an open floor plan with a completely renovated kitchen flowing into the living room with fireplace and built-ins. Updates include new windows, luxury vinyl plank flooring, interior doors, lighting, switches, outlets, and electrical finishes throughout. Ideally located toward the rear of the complex, the unit overlooks the pool and landscaped grounds, offering a peaceful setting with added privacy. One of the standout units in the complex, this turnkey property combines quality updates, an excellent location, and the convenience of being within walking distance to shops, restaurants, and everything historic Woodbury has to offer.

229 Bacon Pond Rd Unit 313, Woodbury

$420,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203216 MLS

Welcome to 34 Pilgrim Trail, a home thoughtfully cared for and enjoyed for 25.5 years. This peaceful Woodbury property features granite kitchen countertops, a tiled backsplash, stainless-steel appliances, and a ceramic kitchen floor. Solid pine doors throughout the home add warmth and character. The upstairs bathroom has been beautifully updated, including the tub and a solid-rock vanity countertop. The upper bedroom/closet offers flexible use and can easily be converted back to a bedroom. Additional improvements include updated closet systems, a refreshed closet near the upstairs bathroom, and a roof installed in 2011. The home is generator-ready, with the generator located outside. Enjoy the tranquility of the property while remaining just minutes from Main Street, shopping, and New Morning Market. Nearby schools and everyday conveniences make this a wonderful place to call home.

34 Pilgrim Trl, Woodbury

$549,900

2 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24201487 MLS ⋅ Woodbury Hill BLDG.

Beautifully renovated and move-in ready, this stand-alone unit in the charming Woodbury Hill condominium community offers a bright, open floor plan and the convenience of first-floor living. Hardwood floors run throughout, while the expanded living room features a cathedral ceiling and dramatic floor-to-ceiling brick fireplace. The completely renovated kitchen opens to the dining room, creating an easy flow for everyday living and entertaining. Sliders lead to a private deck and small patio overlooking the backyard. The first-floor primary suite includes a walk-in closet and full bath. Upstairs, the sought-after loft provides flexible space for an office, den, or TV room, along with a second spacious bedroom and full bath. A finished lower-level room offers additional living space, while the attached two-car garage and full basement provide excellent storage. A beautifully updated home in one of Woodbury's most desirable condominium communities.

25 Woodbury Hill, Unit 25, Woodbury

$620,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24198134 MLS ⋅ South Brook BLDG.

Classic New England style village with 21 free standing homes in a luxurious condominium setting on 37 acres. Lighted walkways, open spaces and hiking trails. Upscale homes with all the charm of yesteryear with todays appointments. Master bedroom on the first floor with full bath and large walk in closet, dining room, living room and huge country kitchen with sitting area and fireplace. Hardwood floors throughout plus a large basement. Private patio area is a welcome site. Rarely is a South Brook home available and its location is perfect with quick access to coffee shops, library, senior center, shopping, hiking trails to the town tower and so much more.

13 Hillview Ln, Woodbury

$600,000

9 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24195107 MLS

Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while the remaining units present an opportunity for renovation and value-add potential. The separate commercial building offers flexibility for a variety of business, office, or retail uses, creating multiple income opportunities on a single property. Properties offering this combination of residential and commercial space in such a prime Woodbury location rarely become available. Whether you're looking to expand your investment portfolio or reimagine a mixed-use property with significant upside, this is an opportunity not to be missed. Property is being sold as-is.

137 & 141 Main St S, Woodbury

$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 that homes a Viessmann Furnace and hot water heater. 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

$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

$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

$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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