My Office's Listings

Some or all of the listings below are provided by the The Masiello Group office.
$699,000 (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
$649,500 (USD)
Active

Halifax Area Single Family Home

Active

800 Hubbard Hill Halifax, VT 05358

3 Bed
3 Baths
2520 sqft
MLS# 5092490
This stately Colonial Revival style home is situated privately on nearly 10 acres with its awesome 3 story 30' X 40' barn accessed by a long winding driveway.  The main level features include large spacious rooms with wainscoting and natural woodwork, an open kitchen/dining/living floor plan, half bath/laundry and a pantry off kitchen, proper foyer, living room with a grand fireplace, wide staircase and hallway from formal entry, office/den and maple and cherry flooring throughout.  On the second level you'll find the primary bedroom suite which occupies half of the floor, 2 additional large bedrooms, red oak and wide pine flooring and access to the sizable attic space which could be finished into additional living space.  The entire house is filled with natural light from its numerous 12 over 12 windows and has a wonderful flow and overall feel.  It's one of those homes that feels like an older traditional home but is a modern dwelling with high quality construction and materials with outstanding systems.  The full basement is walkout at grade with a roughed in section that could easily be finished if more space is needed.  The house is cooled by two central AC units and heated by redundant oil systems. It has radiant hot water heat throughout the first floor, and HW baseboard up but also has forced air units.  Then there's the barn! It's an impressive structure and can fill a variety of needs such as a wood shop or limitless storage for all the toys needed to enjoy the year-round recreational fun of the lakes and mountains of the Green Mountain National Forest just a short drive north. The land is sloping with level areas including a small field with gardening opportunities. The back deck overlooks a small lawn area and beautiful stone steps and gardens leading down to it. If you are looking for a spacious home with plenty of room for expansion, move in condition and a large outbuilding all in close proximity to lakes and skiing in southern VT, this is ideal.
Listing Courtesy of PrimeMLS / Listed By: Christopher Long, Better Homes And Gardens Real Estate The Masiello Group
$585,000 (USD)
Active

Westminster Area Land

Active

0 Pine Banks Road Westminster, VT 05346

Bed
0 Baths
sqft
MLS# 5096685
Exceptional opportunity to own 36.69 acres of scenic Vermont countryside on desirable Pine Banks Road on the Westminster/Putney border. This beautiful parcel offers a rare combination of expansive open meadows, wooded privacy, and breathtaking long-range views across the Connecticut River Valley and surrounding Green Mountain foothills.

The property's rolling landscape provides multiple potential building sites, each positioned to capture stunning vistas, spectacular sunsets, and the peaceful beauty of the surrounding countryside. Open fields create endless possibilities for a private estate, hobby farm, equestrian property, agricultural use, or recreational retreat, while mature trees along the perimeter provide natural privacy.

Conveniently located just minutes from Interstate 91, this property offers the perfect balance of seclusion and accessibility. Enjoy the tranquility of rural Vermont living while remaining within easy reach of Brattleboror, Bellows Falls, Putney, local amenities, and year-round outdoor recreation.

Whether you're dreaming of building your forever home, establishing a country getaway, or investing in a remarkable piece of Southern Vermont land, this exceptional 36.69 acre parcel provides the setting to bring your vision to life. A rare opportunity to own a property where expansive views, open space, and Vermont's natural beauty come together.
Listing Courtesy of PrimeMLS / Listed By: Michelle "Mickey" Hipp, Better Homes And Gardens Real Estate The Masiello Group
$545,000 (USD)
Pending

Brattleboro Area Single Family Home

Pending

211 Pleasant Valley Road Brattleboro, VT 05301

2 Bed
1 Baths
1576 sqft
MLS# 5094642
Perched atop this scenic hillside on 6 acres, this distinctive contemporary home and classic gambrel two-story barn once enjoyed sweeping easterly views to Mount Wantastiquet and distant Mount Monadnock. Glimpses of the long-range views exist but will need to be reclaimed. Located on highly desirable Pleasant Valley Road in West Brattleboro, the property offers an exceptional combination of rural Vermont charm, privacy and convenience, with easy access to town. The beautiful Pleasant Valley Reservoir and the recreational opportunities provided by its protected land, trail system and class 4 road network are an underutilized outdoor paradise just down the road. The home's striking flat roof design, redwood siding, and clean mid-century modern influences create a timeless architectural aesthetic. Inside, the open concept living/dining and kitchen area is filled with natural light from the expansive windows that frame the surrounding landscape. An East/SE facing corner deck provides the perfect setting for morning coffee and sunrise views. The main level features two bedrooms and a full bath updated in 2026. The finished walkout lower level offers a spacious additional living space. The impressive gambrel barn once housed horses in its 3-5 stall lower level and has water and power. The top level of the barn is open clear span with a drive-in door ideal for vehicles and equipment storage, a wood shop, workshop, studio space or a variety of other uses including a possible second dwelling unit with applicable permits. The open land in front of the barn was once a dressage arena and provides an excellent level outdoor space for recreation, animals or agriculture. The remainder of the property includes a mix of open field, young growth forest and established yard areas surrounding the home with abundant room for large gardens and outdoor fun. Despite its peaceful country setting skiing, golf, hiking and biking are only minutes away. A rare one-of-a-kind Vermont property.
Listing Courtesy of PrimeMLS / Listed By: Christopher Long, Better Homes And Gardens Real Estate The Masiello Group
$499,000 (USD)
Active

Marlboro Area Single Family Home

Active

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
$475,000 (USD)
Active

Bennington Area Single Family Home

Active

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
$475,000 (USD)
Active

Springfield Area Single Family Home

Active

175 Pleasant Valley Road Springfield, VT 05156

3 Bed
3 Baths
2680 sqft
MLS# 5084156
MOTIVATED SELLERS just adjusted the price significantly!!! Sweet property with 7.5 acres, great pond, quiet setting and private. This could be your escape to your own peaceful, 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
$475,000 (USD)
Pending

Springfield Area Single Family Home

Pending

185 Crown Point Road Springfield, VT 05156

4 Bed
2 Baths
2655 sqft
MLS# 5098017
This classic New England Colonial has an abundance of history and charm Built in 1870, on the historic Crown Point Road, the property features established gardens, fruit trees, blueberry bushes and more for the gardener or gentleman farmer. With a barn, for equipment or toys, as well as a picture-book sugarhouse, ready for when the warming days of winter nudge the sap to run and it's time to tap a few trees and enjoy making that sweet syrup. Surrounded by beautiful stone walls and established flower gardens it is a joy to behold. As you enter the home through the mudroom, you will find generous storage for all your gear and then on to the spacious open kitchen, featuring a dining space as well as an island and additionally, a built-in desk and shelves. Plenty of cabinets and a wood stove for chilly nights. The adjoining family room offers a quick step out to the deck for relaxing or grilling. The dining room is roomy enough for the largest of gatherings. The spacious living room is bright and has built-in bookcases. A bedroom and bathroom with laundry complete the first floor. As you go up the beautiful staircase, you will find a landing built for viewing or perhaps curling up with a book. The primary bedroom is spacious and bright. A second bedroom again has built-ins and is charming. A third bedroom has a wall of built-ins and is ready to do some finishing touches. A full bathroom serves the second floor. There is a full attic for storage or possible expansion, if desired. This home has so many lovely features, wide board floors throughout, panel doors, the numerous built-ins, a complete kitchen with upgraded appliances and more. A one car garage, the barn, a woodshed and a sugarhouse, this home has it all. It's a must see and ready to embrace a new family.
Listing Courtesy of PrimeMLS / Listed By: Carol Cole, Better Homes And Gardens Real Estate The Masiello Group
$465,000 (USD)
Active

Springfield Area Single Family Home

Active

105 Craigue Hill Springfield, VT 05156

3 Bed
2 Baths
1939 sqft
MLS# 5085886
Motivated Seller has reduced the price dramatically, on this 17 acre, property with a pond and 2 houses, just waiting for you to put your special touches on it. the private setting offers plenty of room for trails, gardens and more. 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