Under Contract Chelsea VT Home for sale $325,000 $146 per sq.ft.

$325,000 $146 per sq.ft. Chelsea VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2230  |  Acres: 1.06
Listed on Monday May 4, 2026
Description: Nestled in the heart of the historic Chelsea District, this beautifully maintained 1850 Colonial offers the perfect blend of timeless charm and modern comfort. Step onto the inviting front porch and into the foyer that welcomes you with traditional grace. On the first level, you'll find a thoughtfully laid-out kitchen with ample cabinetry, a formal dining room, a study featuring built-in storage for a library or personal decor, and a double sized living room all with large windows that bathe the spaces in natural light. Upstairs, all three bedrooms are generously sized, and the over-sized full bathroom includes a large linen closet and laundry hook-ups for convenience. The primary suite boasts an additional office or seating area, ideal for remote work or a cozy reading nook. Completing the property is additional storage or workshop space, attached to the back of the house, and lastly on the third floor is a very large walk-up attic. This classic Chelsea home is a rare opportunity to own a piece of Vermont history, just steps from local amenities and attractions. A few doors down is the Free Verse Farm Shop which is a quaint community-centered general store with alfresco seating. It's a great place to dine from their daily menu or simply enjoy a tea or coffee outside. The Free Verse Farm shop supports local farmers, artisans, and features a full selection of herbs and apothecary products. Once you step inside, you'll fall in love with the ambiance of old world America. See Listing Details & 60 images.

$225,000 $170 per sq.ft. Chester VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1327  |  Acres: 0.13
Listed on Wednesday Jun 18, 2025
Description: Don't miss this incredible opportunity to own a lovingly maintained turn-key Victorian home nestled in the heart of charming Chester, Vermont. Whether you're seeking a warm and welcoming ski retreat or a comfortable year-round residence, this timeless property offers the perfect blend of historic character and modern convenience. Step inside and you are immediately welcomed by the large foyer, which is a great space to store the skis, poles and helmets from a great day of skiing. The main level features a generous living room anchored by a classic wood-burning fireplace ideal for cozy winter evenings. The sunny eat-in kitchen provides ample space for meals and gatherings, while the full bath with laundry adds everyday practicality. All windows were replaced in 2019, offering energy efficiency and bright natural light throughout. Upstairs, you'll find three spacious bedrooms, including a stunning turret space that creates a bright and airy nook perfect for reading or relaxing under the sun-drenched windows. The original woodwork and architectural details throughout highlight the craftsmanship of a bygone era. Outside, the covered wrap-around porch invites you to unwind and enjoy the peaceful sounds of the nearby babbling brook. Take a short stroll to the local market or explore the picturesque village with its shops, restaurants, and small-town charm. This home is more than just a place to stay it's a place to create lasting memories. All only 15 miles from Okemo Mountain! See Listing Details & 26 images.

Under Contract Chester VT Home for sale $250,000 $219 per sq.ft.

$250,000 $219 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1140  |  Acres: 0.25
Listed on Wednesday May 13, 2026
Description: There's something quietly reassuring about a home that's stood the test of time--and this classic dormered Cape in Chester delivers just that, with a clean, updated feel that suits today's lifestyle. Built circa 1945, the home offers three comfortable bedrooms--including a convenient ground-floor bedroom--and 1.5 baths, giving you flexibility for guests or single-level living. The layout is practical and easy to live in, and the enclosed rear entry porch adds everyday function--perfect for muddy boots, groceries, or easing into the house after a long Vermont day. Out back, the porch doubles as a relaxed hangout space, or step out onto the sun-filled deck for a bit more light and fresh air. It's an easy, inviting setup for morning coffee or winding down at the end of the day. Downstairs, a full basement provides solid storage or workspace potential, while the detached two-car garage--with workshop space and automatic openers--offers flexibility for projects, hobbies, or extra gear. The paved driveway, standing seam metal roof, and straightforward systems like the oil-fired hot water setup all point toward low-maintenance ownership--something buyers appreciate more and more. The home is being offered with key appliances already in place, including an electric range, refrigerator, microwave, washer, dryer, and dehumidifier, making for an easy transition whether you're just starting out or simplifying your next chapter. Set in one of Southern Vermont's most loved villages, this is the kind of property that works just as well as a first home as it does for downsizing. Simple, solid, and well-located--if Chester's been on your radar, this one's worth a closer look before it slips by. See Listing Details & 20 images.

Under Contract Chester VT Home for sale $269,000 $230 per sq.ft.

$269,000 $230 per sq.ft. Chester VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1168  |  Acres: 0.5
Listed on Monday Apr 6, 2026
Description: This cozy gambrel style home tucked away on a nice level 1/2-acre lot just on the outskirts of Chester village offers lots of yard space, lots of storage space and is an easy keeper. This cute home offers hardwood floors on the first floor, has lots of natural light, an enclosed porch that could work as a home office, dining area, mud room or just a place to hang out. 2nd floor features three bedrooms with the primary leading out to a deck overlooking the yard. Nice high ceilings on the second floor make the rooms very open and bright. There's an attached storage room allowing room for freezers, storage or a second mud/entry room. Large 2 bay garage with second floor storage, a side shed that would be perfect for a garden shed and a separate space for lawn and snow blowers. The owners have done lots of upgrades, including a full house generator. So, if you are looking, be sure to add this home to your list. See Listing Details & 34 images.

$299,000 $201 per sq.ft. Chester VT Home »


Price Change! Reduced by $100,000 down 33% on June 2nd 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1488  |  Acres: 0.25
Listed on Saturday Sep 13, 2025
Description: Welcome to your dream home - This meticulously maintained and efficient New England-style gem is bursting with charm and modern convenience. Extra insulation, new windows and new hot water heater make this home as energy-efficient as it is beautiful. Picture yourself whipping up meals in a kitchen with custom Hugh Pennell solid wood cabinets, upgraded appliances and solid countertops. Be wowed by the gorgeous hardwood floors that add warmth and character to every room. Bask in the great natural light that fills every corner of this lovely abode, making every day feel bright and inviting. This home includes a main level bedroom, dining room and family room. In addition there is an attached garage and a barn for all your hobbies. This home is perfect for families and outdoor enthusiasts alike. Imagine being just a short stroll away from the village store for all your essentials and enjoying nearby skiing adventures in winter, along with shopping and restaurants year-round! Don't miss out on this incredible opportunity to own a piece of paradise in the heart of it all! Schedule your visit today and get ready to fall in love - your perfect home awaits! See Listing Details & 30 images.

Under Contract Chester VT Home for sale $340,000 $162 per sq.ft.

$340,000 $162 per sq.ft. Chester VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 2096  |  Acres: 1.69
Listed on Friday Mar 20, 2026
Description: Welcome to a charming village retreat in the heart of Chester, perfectly situated on Main Street in the historic Chester Stone Village. This inviting home blends classic Vermont character with comfortable, year-round living. Enter through a practical mudroom with ample space for all your seasonal gear--ideal for embracing Vermont's four-season lifestyle. To the right, at the front of the home, you'll find a bright and open living space featuring a spacious kitchen with a large island, seamlessly connected to the dining area and living room. A glass door leads to a covered porch, creating the perfect spot for morning coffee or relaxing evenings. The main level also offers a dedicated office, a full bathroom, and a convenient laundry room. Toward the back of the home, two bedrooms provide comfortable accommodations, and a stunning family room showcases vaulted ceilings, exposed beams, and walls of windows that fill the space with natural light. A glass slider opens to the back deck, where you'll find an above-ground pool--perfect for summer enjoyment. Experience the charm of Vermont living in this village home, just moments from local shops, dining, and all that Chester has to offer. Visit the Okemo real estate community today. Taxes are based on town assessment. See Listing Details & 55 images.

$349,000 $195 per sq.ft. Chester VT Home »


Price Change! Reduced by $100,000 down 29% on May 7th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1788  |  Acres: 3.3
Listed on Wednesday Jan 14, 2026
Description: Set on 3.30 acres in the hills of Chester, Vermont, this 1900-built home delivers the kind of setting people move here for--flowing water, open land, quiet roads, and easy access to the mountains. The property overlooks a gently moving brook and includes ownership on both sides of the water, giving you your own private stretch of stream and a natural buffer of woods and open space. A quiet paved road leads you home, winding past back woods and pastoral farmland before arriving at the property. The elevated deck becomes your front-row seat to the landscape below--perfect for morning coffee, summer dinners, or simply listening to the brook roll past. Inside, the home feels warm, functional, and comfortable. A large living room is anchored by a substantial woodstove that brings real Vermont heat and atmosphere through the colder months. The sunroom is a standout space, wrapped in windows and overlooking the brook, creating a peaceful place to read, work, or relax. From here, step directly onto the deck and into the outdoors. The layout offers three bedrooms and two bathrooms, including a ground-floor bedroom for easy everyday living. Storage is abundant throughout, making room for outdoor gear, tools, and seasonal equipment. The land itself adds real value. With acreage on both sides of the brook, there's room to garden, explore, build trails, or simply enjoy your own stretch of water and woods. The surrounding countryside delivers classic Vermont scenery--rolling fields, forested hills, and quiet country roads. Located just minutes from the village of Chester and close to Okemo, Stratton, and Magic Mountain, this is a true four-season basecamp for skiing, hiking, biking, fishing, and exploring Vermont's natural beauty. A property that offers privacy, water frontage, land, and mountain access--without giving up convenience. See Listing Details & 31 images.

$390,000 $299 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1304  |  Acres: 1
Listed on Thursday Apr 30, 2026
Description: Fully renovated from top to bottom, this Chester property offers the kind of peace of mind that's hard to find in an older Vermont home. Major systems including electrical, plumbing, heating, insulation, drywall, and windows, have all been updated, allowing the next owner to step in without a long to-do list. Inside, the home strikes a thoughtful balance between character and clean updates. Refinished wide plank floors bring warmth throughout, while the kitchen features granite countertops and a farmhouse sink. Upstairs, a vintage Martini pedestal sink adds a distinctive, curated touch to the bathroom. Outside, the level lawn provides usable space for everything from gardening to entertaining, and the substantial post-and-beam barn opens the door to a wide range of future uses, storage, workshop space, or potential expansion. Located just minutes from Chester's Stone Village, the Grist Mill, and Smitty's Market, and within easy reach of Okemo, Bromley, Killington, Stratton, and Mount Snow, this is a strong option for both full-time living and recreational use. Currently used as a long-term rental and previously operated as a successful Airbnb and personal vacation home, the property offers flexibility for a variety of ownership goals. See Listing Details & 51 images.

Under Contract Chester VT Home for sale $474,900 $360 per sq.ft.

$474,900 $360 per sq.ft. Chester VT Home »


Price Change! Reduced by $24,100 down 5% on May 19th 2026
3 Beds | 2 Baths |   Total Sq. Ft. 1320  |  Acres: 10.86
Listed on Thursday Apr 23, 2026
Description: MOTIVATED SELLERS welcome you to this meticulously maintained chalet in gorgeous Chester, Vermont! Private and secluded, direct access to VAST, located less than an hour from six renowned ski resorts and amenities. So many updates in the past two years; fully remodeled kitchen and bathrooms, fresh paint, new flooring along with numerous updates (list attached in associate documents); modern and cozy with so much charm! Nestled on over 10 acres, you will find walking trails, a fire pit and outbuildings on premises. Vaulted ceilings, open floor plan, lots of natural light and natural woodwork, this is a true move in ready beauty. The rooms are nicely sized and in close proximity to bathrooms. The wood burning fireplace brings a feeling of serenity on those chilly days. Fiber internet on site for those that work remotely. Town records state two bedrooms, however, the loft area has an en suite with a full bathroom and lots of closet space! Plenty of storage, full walkout basement gives ample space. This is one of those properties you won't want to miss on your home buying adventure! Truly a stunning property with so much to offer! See Listing Details & 60 images.

$479,000 $197 per sq.ft. Chester VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2676  |  Acres: 2
Listed on Tuesday May 5, 2026
Description: Located in the village of Chester, this 3-bedroom, 3-bath property offers a rare amount of space and flexibility for an in-town setting. You'll enter through the heated attached two-car garage into a layout that's both functional and easy to live in, with room to spread out when you need it and gather when you want to. The kitchen features warm wood cabinetry, a breakfast bar, and a flexible area that works just as well for casual dining as it does for a home office setup. The dining space flows easily into a sunken living room, where the pellet stove becomes a natural gathering spot. Two bedrooms on the main level, each with their own bath, make this a great fit for a variety of living situations. Upstairs, you'll find a spacious bedroom, a separate flex room currently used as a movie room, and an unfinished bonus area ready for whatever you have in mind. Storage is not an issue here, between the closets and full basement, there's plenty of space to keep things organized. The home is equipped with a new furnace and four heating zones, offering efficiency and control throughout. Outside, a wide back patio gives you a great place to relax, while the barn and oversized three-bay garage offer serious utility for storage, equipment, or hobbies. The detached garage is currently rented for $500 per month, and the tenant would be open to continuing that arrangement with the next owner. The property borders Lovers Lane Brook, adding to the natural setting and privacy, all just minutes to Chester's shops, dining, and village amenities. If you've been looking for an in-town property with more space and versatility than most, this one is worth a look. Furnishings are negotiable for anyone looking for a truly turn-key property! See Listing Details & 60 images. Includes a Virtual Tour

$649,000 $294 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2205  |  Acres: 1.71
Listed on Thursday Jan 15, 2026
Description: Classic New England Salt Box - This charming home is nestled in a hillside neighborhood with wonderful western views and sunsets. Indoors you'll find a tidy mudroom entry with space for all your year round gear. Tiled heated floors lead you to the kitchen featuring newer stainless steel appliances. Vaulted ceilings draw you towards the open dining/living room where you'll be bathed in end of the day sunlight. A bedroom and 3/4 bath round out the main floor. Upstairs you'll find two large bedrooms and a full bath. All good homes should have a family room and this doesn't disappoint. The lower walk out had a cozy spot with a large sectional to watch movies and is perfect for "hanging out" with friends. There is a work out area and a bonus room located on the lower level. This is definitely more than a ski home as there is plenty of outside living space. There is a shady front porch with begs for a rocking chair and a good book. Sun seekers will enjoy the rear deck which faces west and gets plenty of sunshine. Perennial gardens abound and offer color and character all summer long. There is a garage barn that can be used in a myriad of ways... park a car, use the workshop, store your toys... There is also an upstairs mostly finished room that can be your blank canvas. Visit the Okemo real estate community today. Taxes are based on current town assessment. See Listing Details & 60 images.

New Listing! Chittenden VT Home for sale $339,000 $226 per sq.ft.

$339,000 $226 per sq.ft. Chittenden VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1498  |  Acres: 0.72
Listed on Thursday Jun 11, 2026
Description: This quintessential Vermont retreat offers the perfect balance of mountain solitude and modern comfort, perfectly positioned for those who love the great outdoors. Step inside to a light-filled, inviting main level featuring stylish and durable vinyl plankboard flooring throughout--ideal for dropping your gear after a day of adventure. A private primary suite rests at the end of the home with a walk in closet and a luxurious soaking tub awaits to melt away the day's fatigue. Outside, the property boasts a spacious detached garage, offering plenty of room for vehicles, a workshop, or storing your skis, kayaks, and bikes. Speaking of gear, your backyard is a recreational paradise. You are just moments away from the pristine waters of the Chittenden Reservoir, a local treasure for kayaking, paddleboarding, and scenic hiking trails. When winter arrives, the world-class slopes of Pico and Killington Mountain Ski Resorts are just a twenty-minute drive from your front door, making it effortless to catch first tracks on a powder day. Conveniently located a short drive from the vibrant shops, dining, and amenities of Rutland, this home represents a rare opportunity to own a piece of the classic Vermont lifestyle. The unfinished upstairs has insulation, roughed in plumbing and electrical already installed, ready for you to customize this extra living space. If you are looking to customize a full-time residence this property is ready to welcome its next chapter. Open House Saturday 11am-1pm See Listing Details & 41 images.

Under Contract Village of Rutland in Town of Chittenden VT Home for sale $535,000 $265 per sq.ft.

$535,000 $265 per sq.ft. Village of Rutland in Town of Chittenden VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2016  |  Acres: 1.41
Listed on Monday Apr 20, 2026
Description: Step into your own private Vermont retreat at 16 Night Pasture Ln in South Chittenden. Perched on a hill and surrounded by natural beauty, this colonial-style home offers seasonal mountain views that truly shine, especially in the fall. A raised planter along the driveway welcomes you and is filled with a variety of perennial flowers, adding color, charm, and low-maintenance beauty that returns year after year. The spacious backyard provides a rare blend of open lawn and peaceful privacy, backing up to a beautiful tree line. Enjoy morning coffee or evening gatherings on the patio, complete with a built-in fire pit. With space to play and raised garden beds already in place and plenty of raspberry and wild blackberry bushes around the yard and strawberry plants and a blueberry bush around the patio, this outdoor space captures the essence of Vermont living. Enjoy your morning coffee on the deck while listening to the gentle flow of the stream in your backyard and birds singing. Inside, the first floor features a bright, open-concept kitchen and living area with recent updates, including new flooring and appliances such as a refrigerator and dishwasher. A large dining room offers the perfect setting for family meals and gatherings, while the first-floor den provides flexible space for a playroom, home office, or additional living area. Upstairs, the spacious master bedroom includes a full bathroom, walk-in closet, and the added bonus of waking up to beautiful mountain views. Two additional bedrooms, a full bathroom, and an office complete the second floor, along with a new washer and dryer for added convenience. The unfinished basement offers excellent potential to expand your living space and is ideal for a home gym, recreation room, or bonus area. Whether you're looking to relax, entertain, or grow into your space, this home offers comfort, flexibility, and scenic Vermont charm all in one. Seller is a Vermont Licensed Real Estate Agent. See Listing Details & 47 images.

$759,900 $362 per sq.ft. Clarendon VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 2100  |  Acres: 3.46
Listed on Tuesday May 5, 2026
Description: Step into timeless elegance with this single-level, 3-bedroom, 2-bathroom home set on 3 acres of picturesque Vermont countryside. Thoughtfully designed and built with uncompromising quality, this residence blends sophistication with everyday comfort. The interior boasts gorgeous flooring, a chef's kitchen with granite countertops, rich cherry cabinetry, detailed tile work, and high-end finishes throughout. The primary suite is a retreat of its own, featuring an en-suite bath with a beautiful tile shower and walk-in closet for both luxury and convenience. A bonus sun-filled 3 season room just off the back deck features gleaming wood floors and is the perfect spot to relax and take in Vermont's natural beauty! The spacious basement offers exceptional potential and houses a Budarus furnace with 200-amp electrical service. For horse enthusiasts or hobbyists, the property's separate barn is a rare find--equipped with electricity, a frost-free water outlet, and its own 100-amp service. No expense was spared in creating this exceptional property. This home truly lacks nothing - the only thing missing is you and your personal belongings. Don't miss your chance to own this gem-Schedule your private showing today!! See Listing Details & 54 images.

$129,000 $165 per sq.ft. Corinth VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 780  |  Acres: 8.5
Listed on Monday Apr 6, 2026
Description: If you've been looking for a rural Vermont property to make your own, 1343 Chelsea Road is worth a look. Situated on 8.5 acres along Meadow Brook, this parcel offers privacy and mature evergreens on all sides. Note that the property is located in a flood zone. The standout feature is the two-story gambrel barn with two garage bays, a concrete floor, built-in workbenches, and a large upper level with impressive timber framing and a metal roof, ready for storage, a workshop, or finishing into additional space. The existing home is a manufactured home that will need significant work or replacement. A dug well and septic system are on site. Buyer to do their own due diligence in determining the condition and functionality of current systems. At $129,000, this is priced for what it is: a project property in a quiet corner of Orange County. If you're a contractor, a homesteader, or someone looking to get into the Vermont market at a lower entry point, this one has potential. See Listing Details & 51 images.

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