Properties Near 472 Main Street Chester, VT

The Laurin Whiting House, circa 1850, is a Greek Revival style home with 5 bedrooms and 7 baths on 1 +/- acre. The curved, multi-bay veranda wraps around the front of the house with neo-classical columns and an oculus that punctuates the front gable end. A light-filled living room has French doors that open to the lovely porch and adjoin a large bedroom and full bath. The formal dining room connects with the eat-in kitchen with side entrance. An elegant foyer staircase leads to the large landing area on the second floor and a large, ensuite primary bedroom. A third bedroom adjoins a full bath and connects to a back stairway and two additional bedrooms and a bath. The convenient mudroom with adjoining half bath and laundry room connects the house to the barn/event space. The original barn is redesigned to function as a conference center. The meeting space has a separate bar area, two half baths, a tv/game room with exposed beams and a second floor billiard room. The potential uses for this multi-faceted property are many- a spacious full-time home with a business, a duplex, vacation home, ski club or an investment property with rental potential. A large, level yard offers space for gardening, badminton or croquet and a back deck for enjoying summer evenings. Walk to the Town Green for Summer Concerts, shopping and festivals and to the Town Rec area around the corner for year-round exercise and fun!

Experience the warmth of history with the ease of modern living at 663 Depot Street. This fully renovated 3-bedroom, 2-bath home offers historic charm with today’s updates. Since 2022, insulation, drywall, electrical, plumbing, HVAC, furnace, water heater, fixtures, countertops, cabinets, and appliances have all been replaced. The home's original wood flooring has been carefully refinished to honor its roots. Period-appropriate paint colors and thoughtful details like exposed beams and original woodwork add to the timeless feel. The attached 2-story post-and-beam barn—larger than the house—offers incredible potential to expand your living space or create a dream workshop. Set on 1 acre with a sprawling lawn, fire pit, and a prime location near Chester’s Stone Village, Grist Mill, Smitty’s Market, and more. Just 15 min to Okemo and the lakes, 30 min to Bromley, and under an hour to Killington, Stratton, and Mount Snow, it’s ideal for year-round fun. Currently enjoyed as both a family getaway and a successful Airbnb, it offers strong income potential. Whether you’re looking for a primary home or investment, this timeless property is not to be missed.

This charming multi-level home provides 4 bedrooms and a variety of places to find private space for quiet. Also a large open recreation room which includes a full size pool table/table tennis table and dry bar. Located just 3 miles from the charming Town of Chester. An easy drive to Bromley Mt, Magic Mt and Okemo, this makes a great home for an active family. Beautiful views from the deck provide a great place for morning coffee and an evening watching the stars. There is plenty of space for gardens and outdoor activities as well as wooded land to spend relaxing time in. House has automatic whole house propane generator. There are two firemen that live on the road, so it is always well plowed and maintained.

Nestled in one of Vermont’s historic locations, Chester’s Stone Village offers timeless charm and rich character. This classic Federal-style home—featuring brick ends and a clapboard front—could be your next residence or vacation retreat. While this brick sided inviting 4-bedroom, 2-bath home isn’t built of stone, it belongs to a rare collection of nine homes and a church constructed in the 1830s and 1840s by local masons using stone from nearby Mount Flamstead. The home maintains many of its original features while offering thoughtful updates including new roofing, upgraded electrical systems, and improved plumbing. The updated kitchen provides ample counter space and includes a charming breakfast nook or office area. You'll also find a formal dining room, a living room, and two additional spacious rooms. Upstairs, a beautifully crafted staircase leads to three bedrooms, a full bath, and a half bath. Highlights include wide board flooring, built-ins, and custom woodwork. Step outside to enjoy established gardens, blooming perennials, a hidden stone garden, a patio, and a fire pit—perfect for relaxing or entertaining. Located 12 miles from Okemo Resort, you’ll have easy access to year-round activities including skiing, golfing, hiking, and snowmobiling. This unique Stone Village home is a 5 minute walk to a great local store known as Smitty's. Don’t miss it—come explore Chester and the Okemo Valley community today. Taxes are based on town assessment.

Tucked away on a quiet dirt road, this spacious sunny south-facing home offers a peaceful retreat with sweeping views of the surrounding countryside. Step onto the expansive front deck and take in the stunning long-range scenery, including a picturesque pond just beyond the property—yours to enjoy without the upkeep. Inside, the home is open and inviting, with plenty of room to relax or entertain. The large finished basement provides valuable living space, ideal for a game room, media area, or accommodating guests. Recent improvements include a brand-new roof and a high-efficiency propane furnace, both installed just last year, offering modern comfort and peace of mind. Ideally located close to Okemo, plus Stratton, and Magic Mountain are just a short hop away; this property offers the perfect balance of privacy and accessibility. With Vast trails, dirt roads to roam on this is a heavenly location. Whether you're seeking a full-time residence or a weekend escape, this home welcomes you to experience the best of Vermont living.