Properties Near 115 Orcutt Drive 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.

23 Boedtker Road is nestled on a beautiful, open lot with perennials and mature blueberry trees. Surrounded by woods, you'll enjoy nothing but the sounds of nature and complete privacy. If you're in need of one-story living, this is the home for you, as it has two bedrooms, a full bath, and laundry located on the first floor. Just ten minutes to Chester or Springfield will bring you to shopping and restaurants, as well as to a hospital. There are several major ski areas within a 40-minute drive, and access to I91 is in close proximity. If the power goes out, not to worry, because there is a whole-house Generac generator waiting to go! The home is meticulous, clean, and clearly well cared for. There is a full basement with a workshop area and plenty of storage throughout the home. Showing to pre-approved buyers only.

This charming village home in Chester, located on a peaceful dead-end street, offers a fantastic blend of comfort and convenience. The house has been meticulously maintained both inside and out. It boasts a spacious double lot with beautiful gardens and fruit trees. Inside, you'll find two bedrooms plus a versatile den, providing ample living space. The kitchen has been doubled in size with walls of windows bringing both sunshine and views of the backyard. The oversized living room with built-in shelving is highlighted by a cozy brick fireplace. Plus, with town water and sewer, you'll enjoy hassle-free living and can take advantage of the enormous unfinished attic space. This home also features a full basement, offering plenty of storage or potential for future expansion. This is one of Chester's most coveted neighborhoods offering proximity to the town green, tennis courts, pool, frisbee golf and so much more. Visit the Okemo real estate community today. Taxes are based on current town assessment.

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.

Nestled on a peaceful hillside in the town of Andover, this well-maintained home offers the soothing sounds of the Andover Branch River as your daily backdrop. Enjoy the ease of one-level living with three bedrooms, a full bathroom, and a comfortable main living space perfect for relaxing or entertaining. The walkout basement adds even more potential. Already underway is a second full bathroom and a bonus room, complete with closet. Electrical and plumbing are in place, and hardwood flooring, a vanity, and a toilet are ready for installation by the new owner. Whether you choose to finish it as an in-law suite, rental unit, or additional living space, the possibilities are plentiful. Step outside onto the brand-new 582-square-foot deck and take in the tranquil sights and sounds of nature—birdsong, breezes, and the gentle river flow. An open level yard is perfect for outdoor games or fire pit. For those seeking extra functionality, a poured concrete slab is ready for a future barn or garage, complete with electric and water hookups. This unique property combines comfort, nature, and future potential in one beautiful setting. For all the mountain enthusiasts the property is located 11 miles from Okemo Resort and 8 Miles form Magic Mtn.

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.

Welcome to this updated and easy-to-maintain Cape, perfectly located just outside of town with quick access to shopping, skiing, hiking, biking, golf, and great local restaurants. The ideal mix of privacy and convenience, close to everything, yet peacefully set away from the noise. This three-bedroom home features a spacious family room with a marble-faced fireplace, a great space to relax or entertain. Recent upgrades make this home move-in ready, with low maintenance so you can spend less time on chores and more time exploring. Key improvements include a new roof, hot water heater, septic riser, upgraded electrical, mini-split system, and a wall battery. Enjoy two water sources: a newly drilled well with a new pump and adjustable water pressure control and the original dug well as a backup. A fenced-in yard, freshly painted deck, and strategic tree work bring in just the right amount of natural light. Additional features include a large two-car garage, a detached barn with power, a paved driveway, a large family room with natural hardwood floors in a parquet style, and hot tub electrical hook up in covered lean-to behind the garage. Whether you're working from home, hosting friends, or heading out for weekend adventures, this home offers comfort, flexibility, and the upgrades that matter.