$739,900 $256 per sq.ft. Castleton VT Home »


Price Change! Reduced by $10,000 down 1% on July 28th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2890  |  Acres: 0.9
Listed on Tuesday Nov 25, 2025
Description: Discover this charming 3-bedroom, 3-bathroom home overlooking beautiful Lake Bomoseen, complete with deeded lake access, two docks, and a deck with space for a grill perfect for waterfront dining and relaxation. Enjoy summer boating and winter recreation, including ice skating, ice fishing, cross-country skiing, and snowshoeing right on the lake. The remodeled kitchen opens to a bright dining area, which flows into a sunken living room featuring a cozy wood-burning stove for chilly evenings. The first floor also includes an office, a ¾ bath, and a convenient laundry area. Upstairs, you'll find three bedrooms, including a primary suite with stunning lake views and direct access to the full bathroom, which is shared with the additional two bedrooms. A spacious bonus room with its own full bathroom completes the second floor, ideal for a playroom, guest suite, hobby room, or flexible living space. Outside, enjoy a large deck perfect for entertaining, a relaxing hot tub, a generous yard, and a peaceful, private setting. A 3-bay garage provides ample room for parking, storage, and all your recreational toys. Since 2020, the owners have completed numerous updates, including a fully remodeled kitchen, new garage doors, a new roof with skylights, fresh exterior paint, and many additional cosmetic improvements throughout. See Listing Details & 52 images.

$795,000 $523 per sq.ft. Castleton VT Home »

104 Ft. of Waterfront on Lake Bomoseen
3 Beds | 2 Baths |   Total Sq. Ft. 1520  |  Acres: 0.89
Listed on Friday May 22, 2026
Description: Discover your ideal year-round home on Vermont's beautiful Lake Bomoseen, featuring over 100 feet of shoreline and complete with four docks and six boat slips! Originally constructed in 1850, only one beam from that era remains, as the home was meticulously rebuilt and renovated in 2009. With three spacious bedrooms and two well-appointed bathrooms, this inviting home is ready to welcome you to the lake. The first floor features a modern white kitchen that opens to the dining and living areas, all with great views of the lake. Also on the main level is the primary bedroom, complete with a generous walk-in closet and adjacent primary bath. Ascend to the second floor, where you'll find two additional bedrooms, another beautifully designed bathroom, and a laundry room. The comprehensive renovation ensures that the home is equipped with modern amenities and efficient systems, including mini-splits for summer comfort, a forced hot air propane furnace, and a heat pump hot water heater, as well as public sewer and a private well. Located just past the boat rental facility, this exceptional property includes a rare double lot totaling 0.89 acres, comprised of two separately deeded parcels. The home itself rests on 0.52 acres, while the adjoining 0.37-acre lot offers a unique opportunity to potentially build a garage or guest cottage, subject to permitting. The expansive backyard is perfect for entertaining, providing ample space for gatherings, a flourishing garden, or simply enjoying the serene surroundings. This property offers everything that is hard to find in a lake home: year-round living, easy lake access, ample dock space with income opportunities, a circular drive with plenty of parking, and a large double lot. Don't miss your chance to embrace the best of lakeside living--schedule your private tour today! See Listing Details & 40 images.

$885,000 $447 per sq.ft. Castleton VT Home »

Waterfront on Lake Bomoseen
3 Beds | 3 Baths |   Total Sq. Ft. 1980  |  Acres: 0.12
Listed on Monday Jul 20, 2026
Description: Spectacular year round contemporary log home on the eastern shores of Lake Bomoseen, offering breathtaking sunset views over the crystal-clear water. Relax and entertain on the spacious deck while taking in the beauty of one of Vermont's most desirable lakes. Designed with an open-concept floor plan, the home features a beautifully appointed granite kitchen that flows seamlessly into the dining and living areas. A striking fieldstone gas fireplace serves as the centerpiece, creating a warm and inviting gathering space, all framed by stunning lake views. The main level includes a spacious primary bedroom with dual walk-in closets, providing both comfort and convenience. Upstairs, you'll find two generously sized bedrooms, a full bath, and a loft overlooking the living area below while capturing picturesque views of the lake. The finished walk-out lower level expands the living space with a welcoming family/recreation room, perfect for entertaining, game nights, or relaxing after a day on the water. This level also includes a utility room with a laundry area and ample storage. Whether you're looking for a year-round residence or a lakeside retreat, this exceptional waterfront home offers the perfect combination of rustic elegance, modern comfort, and unforgettable Lake Bomoseen living. Just a short drive to Killington for skiing and near snowmobile trails, Castleton University and Middlebury. See Listing Details & 32 images.

$995,000 $767 per sq.ft. Castleton VT Home »

370 Ft. of Waterfront on Lake Bomoseen
3 Beds | 1 Baths |   Total Sq. Ft. 1298  |  Acres: 0.71
Listed on Friday Jun 26, 2026
Description: A once-in-a-generation opportunity to own one of the most extraordinary and iconic properties on Lake Bomoseen. Tucked away on the private point of Acorn Lodge, behind Rabbit Island, this storybook lakefront retreat occupies one of the most coveted settings on the entire lake. Surrounded by water on multiple sides, the property offers unmatched panoramic views that stretch in every direction, creating the feeling of your own private peninsula. From sunrise reflections to spectacular sunset skies, every corner of this property captures a breathtaking perspective of Lake Bomoseen. Built in 1880, this charming 3-bedroom, 1-bath home is one of the last remaining original lake homes on Lake Bomoseen. A rare piece of the lake's history that can never be replicated. Rich with character and timeless appeal, it offers the chance to own not just a home, but a legacy. The waterfront is simply unrivaled. Featuring spectacular lake frontage, two brand-new oversized docks, direct deep-water access, and a boathouse providing ample storage for all your lake toys and equipment, this property is designed to maximize every aspect of lake living. Equally rare is the expansive, flat, and highly usable land which is a true luxury on waterfront properties and provides endless opportunities for entertaining, recreation, and future enjoyment. Properties of this caliber and uniqueness seldom come to market. The combination of historic charm, unparalleled views, exceptional frontage, direct lake access, and a private point setting creates an offering unlike any other on Lake Bomoseen. Whether enjoyed as a treasured family retreat for generations to come or transformed into your ultimate waterfront escape, this is a truly once-in-a-lifetime chance to own one of the lake's most remarkable properties. Come see for yourself just how special this property is! Give us a call to schedule your own private showing today and enjoy your 2026 summer lakeside. See Listing Details & 50 images.

Under Contract Cavendish VT Home for sale $260,000 $208 per sq.ft.

$260,000 $208 per sq.ft. Cavendish VT Home »

3 Beds | 1 Baths |   Total Sq. Ft. 1248  |  Acres: 1.6
Listed on Thursday May 28, 2026
Description: Welcome to 50 Bates Rd, a charming 1920s Vermont farmhouse perched above the village of Cavendish, offering a country setting with the convenience of being in town. The standout feature is the large covered porch -- the kind of welcoming outdoor space that feels from another era and invites you to slow down and take in the setting. This home is ready for updating, but the character is already here: original hardwood floors, a country kitchen, beautiful doors, classic woodwork, period lighting, and built-ins that add both charm and practical storage. Some of the less glamorous but important improvements are already underway, including a new furnace and water heater, allowing the next owner to focus on the more enjoyable parts of renovation and design. The property also offers space for future perennial gardens and a setting with a sense of local history. Just a short drive to Okemo Mountain Resort, area restaurants, shops, and recreation, this is a wonderful opportunity to restore a home with soul in a great village location. Visit the Okemo real estate community today. Taxes are based on town assessment. See Listing Details & 52 images.

$725,000 $341 per sq.ft. Cavendish VT Home »


Price Change! Reduced by $70,000 down 10% on June 3rd 2026
3 Beds | 3 Baths |   Total Sq. Ft. 2128  |  Acres: 19.06
Listed on Monday Oct 27, 2025
Description: Living and working in the country with privacy, wildlife, snowmobiling from your front door, skiing at Okemo, and the overall beauty of Vermont would be a dream come true, right? Well, here's your opportunity with this pretty log home on 19 acres on a dead-end town-maintained road. Inside the house, you will love the open concept of the living room, and the kitchen and dining room with cathedral ceiling. Enjoy the warmth of the all-natural wood surroundings while sitting beside the cozy fire from the wood burning stove. There are 3 large bedrooms and 2 1/2 baths. The floors are nicely finished hard and soft wood, with slate tiled floors in the entryway and kitchen. SNOWMOBILE ENTHUSIASTS! The VAST trail is right here, so hop on your sled from your house and go! See Listing Details & 41 images.

$730,000 $203 per sq.ft. Village of Proctorsville in Town of Cavendish VT Home »

150 Ft. of Waterfront on River Black River
3 Beds | 5 Baths |   Total Sq. Ft. 3590  |  Acres: 7.59
Listed on Tuesday Jun 30, 2026
Description: Back on the market and drastically reduced! Situated on the bank of the Black River at the edge of the Village Of Proctorsville is this three bedroom all ensuites, 5 bath log home. The Great Room boasts a local stone floor to cathedral ceiling wood burning fireplace where you can sit and relax after a day on the slopes. Then take in river views from the formal dining room. Also on the first floor is a primary ensuite. Upstairs the huge lofted area is the perfect spot to game, watch TV or just chillax. Two ensuite bedrooms with private decks to take in the view of Hawks Mountain Range and the Black River. The attached two car oversized garage has enough room for cars and toys. A little TLC and a couple finishing touches and this house will be dynamite. See Listing Details & 36 images.

$795,000 $329 per sq.ft. Cavendish VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 2416  |  Acres: 3.29
Listed on Thursday Jun 18, 2026
Description: Enjoy the best of Vermont living in this recently built 3-bedroom, 2.5 -bathroom country home in Cavendish. Designed with comfort and functionality in mind, this home welcomes you through a convenient mudroom with storage--perfect for all your year-round gear. Step into the open-concept living area featuring vaulted ceilings, a wood-burning fireplace, and a seamless flow between the kitchen, living spaces and "pass through" dining area -- ideal for entertaining or relaxing after a day outdoors. The main level also offers views of Okemo, a laundry room and a spacious primary suite complete with a walk-in closet, full bathroom, and glass doors leading directly to the backyard--your own private retreat. Upstairs, you'll find a large family room, two additional bedrooms, a 3/4 bathroom, and a loft overlooking the living room below, adding to the home's airy feel. The backyard is fully enclosed with a new high-end fence for children or pets! Set in a peaceful country setting, yet just a short drive to Okemo Mountain Resort, this property offers easy access to skiing, hiking and biking trails, snowmobile routes, lakes, and golf. Whether you're seeking a full-time residence or a Vermont getaway, this home is ready to welcome you. Schedule your showing today! Visit the Okemo real estate community today. Taxes are based on town assessment. See Listing Details & 58 images.

$895,000 $583 per sq.ft. Village of Proctorsville in Town of Cavendish VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 3291  |  Acres: 0.44
Listed on Wednesday Jul 15, 2026
Description: Welcome to your new home and business headquarters in Cavendish, Vermont. This expansive property near Okemo Mountain Resort blends residential comfort and commercial opportunity. Imagine a chef's dream kitchen with double ovens, refrigerators, and cooktops, perfect for culinary creativity. The home features three large bedrooms, spacious living areas, and a large deck for relaxation and entertaining. It's also the base of a thriving business, offering a turnkey opportunity for entrepreneurs. With 2,000 square feet of unfinished space, your imagination can run wild, perfect for business expansion, a restaurant, ski club, or additional living space. Recent renovations ensure the property is in pristine condition, ready for you to move in. Conveniently located just minutes from Okemo Mountain, this property attracts both local and tourist traffic. Town water and sewer services add to the convenience, making it ideal for residential and commercial use. Whether expanding your home or starting a new business, this property offers endless possibilities. It combines a beautiful home and an established business location. Don't miss out on this rare opportunity in one of Vermont's most desirable locations. Contact us today to schedule a viewing and start imagining the possibilities! ? See Listing Details & 47 images.

New Listing! Chelsea VT Home for sale $365,000 $197 per sq.ft.

$365,000 $197 per sq.ft. Chelsea VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1850  |  Acres: 0.17
Listed on Friday Jul 31, 2026
Description: Chelsea is quintessential small town Vermont - Main Street is lined with century homes, a general store, a natural foods store, a dance hall, and the beautiful town green. Just up the hill on the paved road sits this immaculate country cape! Built in 2017 with great attention to detail, you won't find a home this fresh and new for miles around. The main level offers a comfortable open layout, first floor laundry, essential drop space at the door, a gleaming country kitchen with sparkling butcher block counters, tile backsplash, and an island perfect for entertaining and everyday use. A large full bathroom and a bedroom/office round out this beautiful first floor. Upstairs, you have another updated full bathroom, gigantic freshly-painted primary bedroom, and another bedroom with great built-ins and plenty of light. The full unfinished basement offers excellent storage and work space, and stays bone dry. Outside, you have a picturesque front porch to relax and entertain on, with raised garden beds on the lawn ready for next spring. The trickling stream out back is tranquil and soothing on this stunning property. Come make your home in Chelsea! See Listing Details & 54 images.

$399,000 $283 per sq.ft. Chelsea VT Home »


Price Change! Reduced by $36,000 down 9% on July 14th 2026
3 Beds | 3 Baths |   Total Sq. Ft. 1552  |  Acres: 5.04
Listed on Sunday Jun 14, 2026
Description: Somewhere between the rolling hills of Chelsea and the rest of the world, there exists a place that feels borrowed from Tolkien's imagination, a real-life Shire where the land is green, the air is clean, and time moves at the pace of a babbling brook. This five-acre oasis is the kind of property you don't find; you stumble upon it and wonder how it escaped everyone else. Mature maples stand like quiet sentinels, a working apple orchard offers its seasonal gifts, and a brook winds softly through the grounds, bucolic, unhurried, alive. The 1991-built home offers 3 bedrooms and 3 bathrooms with a vaulted, skylit living room, a main-floor primary suite, and a generous kitchen and dining area that opens to a back deck and the woods beyond. Upstairs, a large landing for reading nook/office and a bedroom. Downstairs on the lower level you'll find another bedroom, bathroom and laundry with storage. The lower level walks out to the side yard for storage and access. A large detached shed offers space for the garden implements necessary to maintain your little apple orchard and the property at large. And unlike the Shire, this Eden comes with fiber optic internet, a standing seam roof, wood/oil combo boiler, and a whole-home generator. Even hobbits need WiFi. Your home. Your escape. Your Vermont. See Listing Details & 47 images. Includes a Virtual Tour

$299,000 $167 per sq.ft. Chester VT Home »


Price Change! Reduced by $150,000 down 50% on July 29th 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.

Under Contract Chester VT Home for sale $390,000 $299 per sq.ft.

$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.

$469,000 $193 per sq.ft. Chester VT Home »


Price Change! Reduced by $10,000 down 2% on July 6th 2026
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

$489,000 $301 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1626  |  Acres: 0.33
Listed on Thursday Jun 18, 2026
Description: Located in the Historic Stone Village of Chester, this thoughtfully renovated and reimagined circa 1880 home combines modern minimalist style with artisan craftsmanship. Set on .33± acres, this light-filled property features wide-pine floors, exposed beams, and a Vermont Castings woodstove anchoring an inviting open-concept living space. The kitchen/dining area showcases country cabinets with butcher block counters, attractive center island with Vermont marble counter, stainless steel sink and dishwasher framed by a wall of windows with a picturesque valley view. A spacious first-floor bedroom, full bath and convenient laundry area provide easy one-level living. Upstairs, two additional bedrooms with generous closets share a stylish full bath finished with classic subway tile. Recent upgrades include energy efficient systems and a new four-bedroom leach field, offering peace of mind for full-time residents, second-home owners, or investors. Offered fully furnished, this turnkey Vermont property has a proven history as a successful seasonal rental. Experience the vibrant community of Chester, with its charming village shops and restaurants, town pool, recreation area, premier disc golf course, pickleball and tennis courts, snowmobile club, and thriving artisan culture. Ideally located near Okemo Mountain Resort and Magic Mountain ski areas. This quintessential Vermont home is equally suited as a primary residence, ski getaway, vacation home, or income-producing investment property. See Listing Details & 34 images. Includes a Virtual Tour

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