My Office's Listings

Some or all of the listings below are provided by the The Masiello Group office.
$799,000 (USD)
Active

Guilford Area Single Family Home

Active

2416 Stage Road Guilford, VT 05301

4 Bed
3 Baths
2353 sqft
MLS# 5088798
A truly magical setting! If you've never experienced the blissfulness of the Green River Village and its historic covered bridge and crib dam/waterfall and one of the most spectacular swimming holes imaginable, it's a must visit southern Vermont destination. Nestled in this picturesque valley village is this charming old home privately situated on 53.5 acres only a short stroll up the driveway from this beautiful waterfall scene. With its open fields, outstanding sun exposure, pond, stonework, established gardens, berry bushes and apple, pear and peach trees this setting will transport you back in time. The towering old growth sugar maples around the house are true giants and are one of the first things that will make your jaw drop as you enter the peaceful homestead. The house needs work but with this stunning location and unique property attributes it's deserving and worthy of the investment. The 4-bedroom, 2.5 bath home features original fir flooring throughout the old portion and oak flooring in the addition, a huge 18' X 34' living/dining room a fireplace and massive hearth, a country kitchen with antique wood cookstove, an office/study (or 1st floor bedroom) and a small bath and laundry on the main level and 3 bedrooms, bath and the primary bedroom suite upstairs. The central heating system was propane hot water baseboard but is not functional at present. The owner currently heats with wood only. Freshly painted in 2025. Roof replaced with standing seam metal in 2005. Property is enrolled in the Use Value Appraisal (current use) with 8 acres excluded encompassing the open land, gardens and pond area around the home site. The true southern exposure, local views of the hills surrounding the river valley, access to the river and the privacy this property provides is special and very difficult to find.
Listing Courtesy of PrimeMLS / Listed By: Christopher Long, Better Homes And Gardens Real Estate The Masiello Group
$525,000 (USD)
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Marlboro Area Single Family Home

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147 Gilbert Road Marlboro, VT 05344

3 Bed
1 Baths
1508 sqft
MLS# 5089735
Virtual Tour
This sweet home is nestled in the serene, and quiet location of Gilbert Rd, a dead end, located on the edge of Newfane but in the quaint town of Marlboro, VT. It has been completely renovated within the past few years by a local high-end builder with an eye for energy efficiency. His workmanship is evident in the renovation. The result: this pristine home gleams with its fresh and inviting design. New heat pumps, insulation and septic provide a clean slate for any homebuyer. All brand-new furnishings for an easy transition. An attractive retaining wall was recently built with field stones and steps for easy access. Many plantings have been added for a colorful summer ahead. A wood stove was installed in the sunroom for year-round comfort. A babbling brook runs along one side of the property, leading to the nearby West River. The home is also an easy commute to Brattleboro for unique eateries, farmers markets, gallery walks and so much more. If you are a skier, Mount Snow is nearby! Hikers will have the opportunity to explore the almost 50 acres this property has to offer. Plenty of open space is available for vegetable gardening, as well. This truly is a lovely home waiting for its next chapter to unfold. (Deed says 52.5 plus or minus and tax bill says 49 acres.) This home is coming mostly furnished making it completely move in ready.
Listing Courtesy of PrimeMLS / Listed By: Monica Sumner, Better Homes And Gardens Real Estate The Masiello Group
$499,500 (USD)
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Springfield Area Single Family Home

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175 Pleasant Valley Road Springfield, VT 05156

3 Bed
3 Baths
2680 sqft
MLS# 5084156
MOTIVATED SELLERS!!! This could be your escape to your own peaceful, private homestead. Set on 7.5 acres of wooded and open land this property is truly a respite from the stresses of the world. This multi-level 3-bedroom, 3 bath home offers convenience and options. The spacious living room with hardwood floors leads to a large eat-in kitchen with ample storage and room for an island if desired. Step into the Family room or a large dining room with access to one of the decks overlooking the pond. The primary bedroom on the third level has a convenient 3/4 bathroom as well as a deck to again enjoy the views of wildlife and the pond. An additional second floor bedroom also enjoys a deck to enjoy the view and wildlife. A full bathroom is convenient on level 3. On the lower level a large family/game room awaits with a wood stove to keep you warm on those chilly nights and offers full access to the back acreage. In addition, a 3rd bedroom and full bath/laundry room make this a true family home.
Wait, there is more, an oversize 2 car garage, heated, for those cool nights, and also an attached work shed, for all the woodworking or hobbies one might enjoy, as well as 1/4 bath for convenience.
Over the garage an open concept apartment features living room, kitchen, 1 bedroom and bath. It has been used as a rental, which one could continue or perhaps use as a guesthouse or Air B&B. The pond is a bonus and ready for enjoyment during the summer months. The property is located with easy access to Springfield and Chester for all your shopping, medical and recreation needs. Hiking, golfing, skiing, entertainment, movie theatre, arts and more.
Listing Courtesy of PrimeMLS / Listed By: Carol Cole, Better Homes And Gardens Real Estate The Masiello Group
$499,000 (USD)
Active

Bennington Area Single Family Home

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425 Main Street Bennington, VT 05201

6 Bed
6 Baths
9000 sqft
MLS# 5087015
15,000 plus sq. ft. commercial/office/retail/residential building on Main St in Downtown Bennington VT. On the ground level there are two prime street front retail spaces on Main Street one the long-term home of the Bennington Banner plus a 4,000 plus sq ft flex space in the rear of the building with great access consisting of open warehouse space ideal for light manufacturing (3 Phase Power), R & D, climate controlled storage, or if you are a service provider company (electrical, plumbing and heating, etc.) in need of more space for at grade storage of inventory, vehicles and offices with easy access it is ideal space to run a service business from. Significant renovations have been completed to the interior 2nd floor of the building. This space is roughly 6,000 sq ft and is a blank slate at present but has been prepped for a residential buildout including plumbing for bathrooms, fire alarm and full sprinkler system, electrical service and other new systems in place. Informal plans have configured 2 to 7 possible apartments in this space depending on size and cost vs. income analysis OR possibly a large in-town owners' residence with skiing, hiking and other year-round outdoor recreational opportunities in the Green Mountain National Forest and Lakes and Rivers within it just a short drive away. Final state and local permits required for finalized development plan. This space combined with the flex space and retail storefronts along main street would be an ideal mixed-use income property. If creating value and optimizing income with creative development of a fantastic building is intriguing, this is an unbelievable and very unique opportunity. At this price point it would be challenging to find another commercial/residential building of this size and condition with this much potential to be solid income property with tremendous equity gain in a very quick timeframe.
Listing Courtesy of PrimeMLS / Listed By: Christopher Long, Better Homes And Gardens Real Estate The Masiello Group
$490,000 (USD)
Active

Springfield Area Single Family Home

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105 Craigue Hill Springfield, VT 05156

3 Bed
2 Baths
1939 sqft
MLS# 5085886
Motivated Seller! Price Adjustment on this17 acre, property with a pond and 2 houses. Close to schools, shopping, medical services and recreation, this property offers privacy, views and a pond. This property also enjoys a beautiful guest house for visitors or a long-term rental. The main house is a traditional cape style with an abundance of porches for viewing wildlife. The entrance foyer and sitting area leads to the living room and the large dining room featuring built-ins. The oversized kitchen provides space for dining or perhaps an island, as well as family room space in front of the wood stove. The primary bedroom enjoys a private sitting area, office or perhaps your yoga space. With 2 more bedroom and 2 baths it is truly a delight. The detached garage hosts a studio/office space overhead. The second living space is located over the 2-car garage and is stunning with the interior done in wood, stonework, tile and more. The open concept living, dining and kitchen features plenty of cabinets and storage. The generous bedroom and bathroom are roomy and comfortable. The sunporch has room for the hot tub and offers views of the pond and mountains. The property has fruit trees, stone walls and some trails with land to develop more for walking or snowshoeing.
Listing Courtesy of PrimeMLS / Listed By: Carol Cole, Better Homes And Gardens Real Estate The Masiello Group
$409,000 (USD)
Pending

Readsboro Area Single Family Home

Pending

104 Johnny Cake Hill Lane Readsboro, VT 05350

3 Bed
3 Baths
1696 sqft
MLS# 5088576
Virtual Tour
If you've been dreaming of peaceful country living with stunning views, this one-of-a-kind home on approximately 21 private acres in the hills of Southern Vermont is calling your name. Greet each morning with an awe-inspiring easterly panorama that, on clear days, stretches all the way to Mount Monadnock.
This serene retreat offers the best of nature — birdsong in the morning, occasional wildlife sightings, and total tranquility. It’s a true country oasis, built with love and vision by the current owner using timber milled from the very land it sits on. The hand-hewn beams give the home a warm, rustic character, seamlessly paired with modern conveniences for comfort and efficiency.
Inside, the home features three bedrooms — two conveniently located on the main floor — and three bathrooms. The spacious living room invites relaxation with its charming soapstone wood stove, while the open dining area boasts panoramic views that will never grow old. The recently completed kitchen features quartz countertops and modern appliances.
The home is well-equipped for sustainable living, with a Tesla battery backup system, energy-efficient mini-splits for heating and cooling, a new propane furnace, and a 2022 state-of-the-art septic system.
Step outside to the expansive deck, where you can sip your morning coffee or unwind at sunset, soaking in the beauty and peacefulness of your surroundings. This property offers everything to embrace the best of country living. This home is on a quiet class 4 road. The town does not plow in the winter; therefore the owner would need to have it plowed themselves.
Listing Courtesy of PrimeMLS / Listed By: Monica Sumner, Better Homes And Gardens Real Estate The Masiello Group
$399,500 (USD)
Active

Springfield Area Single Family Home

Active

264 Elm Hill Springfield, VT 05156

4 Bed
2 Baths
2264 sqft
MLS# 5053763
No words describe this property better than peaceful, rural, convenient and historic. Throughout its long life, the top of Elm Hill exudes country. The rugged stone walls, lower barn, tool shed and upper barn reveal an agricultural past. The upper barn has been converted to a 2-car garage and workshop, complete with a half-ton hoist. The upstairs hayloft (attic type storage) is easily accessible by stairs in the back and double doors on the front. The carriage port has been enclosed to store wood for the Defiant woodstove in the sitting room, adjoining the kitchen. On the south side are a five-tree apple orchard and a garden plot each producing for residents and neighbors alike. Sunshine and natural light define the yard, the views and interior, Foundation plantings thrive in the morning sun. The back hills and fields light up in midday and evening sun. During foliage, the hills across the valley blaze in the sunset. Multiple windows flood the house interior with natural light. Convenience doesn't negate peace. A mere mile from the town central square, where one will find a variety of unique shops, restaurants and even a movie theatre. The house is but a 1.1 mile from the shopping plaza and 1.5 miles from the hospital and with a golf course, ski areas and multiple hiking venues nearby, one can easily get back to nature. In the early morning and evening turkey and deer come from the back hill to feed in the adjoining meadows as well as a variety of colorful songbirds to enjoy. A classic post and beam 4 bedroom, 2 bath home on 1.2 acres was built by James Litchfield when he settled the top of Elm Hill. The original axe-cut post and sturdy beams exposed on the main floor living room, dining room and office attest to its structure and history. Since the first family made this their home in the early 1790s, it has sheltered and nurtured eight families of several generations each. Yours can be the next family to make history here. Come experience the peaceful setting.
Listing Courtesy of PrimeMLS / Listed By: Carol Cole, Better Homes And Gardens Real Estate The Masiello Group