FOR SALE

819 Main St North
Woodbury, CT

Offer at $1,925,000.00

289 Main St South
Woodbury, CT

Offered at $ 898,000.00

105 Minortown Rd
Woodbury, CT

Offered at $ 599,000

2,992 sqft
3 Bed
3 Bath
9.88 Acres

Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in.

5,823 sqft
3 retail
3 apartments
Main St Design zoning

The iconic Lewis Building is in a prime location at the intersection of Rt 6 and Rt 317, next to the town office buildings and library. Can't beat this location! It offers a valuable opportunity for those looking to leverage the growth and vibrancy of the area. MSD zoning offers 3 commercial rentals and 3 residential rentals. Fully occupied with little turnaround. Rents generate a great income. Well maintained with recent upgrades. With excellent visibility this investment opportunity is not to be missed.dly

2,227 sqft
3 Bed
3 Bath
4.05Acres

This ranch-style home might be the perfect fit! Just minutes from town, the property offers a variety of opportunities. The main level features three bedrooms, two bathrooms, a living room with a gas log fireplace, a formal dining room, and a spacious eat-in kitchen. The partially finished lower level includes a family room, office space, and a full bath. Built in 2008, the garage barn provides ample space for four cars, a workshop, and a studio space above. You can also create a path down to the Nonnewaug River for more outdoor fun. House needs some TLC so bring your ideas! Come and enjoy all that Litchfield County has to offer, just 90 minutes from NYC.

22 Clubhouse Dr.
Woodbury, CT

SOLD - Offered at $415,000

1,888 SqFt
3Bed
2.1 Bath

Inspiration Model at Woodlake beautifully renovated from top to bottom. Three bedrooms, 2 renovated full baths, one half baths, fireplace, 5' white oak wood floors, Bosch 800 series appliances, new heat pump system, new ductwork, two bonus rooms in lower level, EV charging device, garage, pond view, two patios, Complex offers walking trails, tennis courts and playground. Community pool going under renovation. Short distance to main street Woodbury with great restaurants, coffee and retail shops.

24 Woodbury Hill
Woodbury, CT

SOLD - Offered at $460,000.00

1577 sqft
2 Bedrooms
2.1 Baths

Wonderful Woodbury Hill!

A delightful community close to the town center. This Trumbull's cape model makes you feel right at home! A spacious living room with cathedral ceiling and a fireplace opens to the dining room. The remodeled kitchen has a walk in pantry and plenty of cabinetry. Sliders open to a private deck. There is a den on the main level along with a powder room. The upper level features the two bedrooms, each with their own private bathrooms. The lower level is semi-finished with plenty of extra storage space. The garage is attached with space in the driveway for a second vehicle. Complex offers tennis courts and a swimming pool,

Woodbury, CT

COMING BACK on MARKET in the SPRING 2026

4,491 sqft + 1,290 finished lower level
4+ Bedrooms
4 Baths
2.61 acres

This elegant Colonial is located in desirable Carriage Hills. You won't lack for space and storage with approximately 5700 sqft including the full walk out lower level suitable for an in-law. Beautiful wood floors greet you as your enter into the two story foyer. Formal living and dining rooms, eat-in kitchen, bedroom, full bath and a great big family room with a fireplace, all on the main level, plus a room off the family room with doors to the oversized deck. The upper level features three spacious bedrooms, full bath and a huge primary suite with a spa like bath and loft space. The lower level has three finished rooms and a full bath. The property is surrounded by trees and dotted with perennial gardens. Come make this your forever home in one of Connecticut's best small towns.