$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
Friday Jun 26, 2026
Description: OPEN HOUSE JUNE 30TH 11 AM - 3PM! 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 MLS Property & Listing Details & 50 images.

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

3 Beds | 1 Baths |   Total Sq. Ft. 1248  |  Acres: 1.6
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 MLS Property & 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
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 MLS Property & 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
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 MLS Property & Listing Details & 36 images.

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

3 Beds | 3 Baths |   Total Sq. Ft. 2416  |  Acres: 3.29
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 MLS Property & 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
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 MLS Property & Listing Details & 47 images.

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

3 Beds | 2 Baths |   Total Sq. Ft. 2230  |  Acres: 1.06
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 MLS Property & Listing Details & 60 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
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 MLS Property & Listing Details & 47 images. Includes a Virtual Tour

$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
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 MLS Property & Listing Details & 30 images.

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

3 Beds | 2 Baths |   Total Sq. Ft. 1788  |  Acres: 3.3
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 MLS Property & Listing Details & 31 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
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 MLS Property & 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
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 MLS Property & Listing Details & 34 images. Includes a Virtual Tour

$495,000 $275 per sq.ft. Chester VT Home »

3 Beds | 2 Baths |   Total Sq. Ft. 1800  |  Acres: 2
Wednesday Jun 17, 2026
Description: This well-maintained property in Chester is in close proximity to many of Vermont's best ski mountains. It is not likely that you would drive by this property without it catching your eye. From the meticulous grounds with beautiful trees to the Vermont native stone wall lining the road, to the established perennial beds to the paved driveway leading back to this pleasing home with an attached garage. This light-filled home with two floors of living (plus a multi-room lower-level walkout ready to finish) has great open space on the main level. The kitchen with updated granite counters is open to the dining area which has a sliding door to the large back deck. This is the perfect space to have dinner overlooking the landscaped back yard. Try your green thumb in the vegetable garden that is ready for planting. The living room is also connected to the dining area making this space perfect for friends and family to gather. A convenient bedroom and bathroom complete this level. Upstairs are two generous bedrooms, a bonus room for a home office or more plus space above the garage that is currently being used as an amazing walk-in closet. Come and take a look at this low-maintenance home in a park-like setting with berry bushes, fruit trees, a gazebo, and a combination garden and wood shed. The stone firepit could be a favorite spot for relaxing by the fire after a day on the slopes. There is a third bay workshop next to the attached garage and an additional detached garage that has a vent pipe for a wood stove and can be of multiple uses. This property will check boxes that you didn't even know you had! See MLS Property & Listing Details & 60 images.

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

3 Beds | 2 Baths |   Total Sq. Ft. 2205  |  Acres: 1.71
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 MLS Property & Listing Details & 60 images.

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

3 Beds | 2 Baths |   Total Sq. Ft. 2204  |  Acres: 1
Wednesday Jul 1, 2026
Description: Joins us for a gallant OPEN HOUSE Friday, July 17th from 3-6PM...serving cold drinks and shrimp cocktails! Welcome to your private gated mini-estate...an enchanting sanctuary where every detail delights the eye. Nestled adjacent to meticulously manicured woods, this one-of-a-kind residence blends storybook charm with thoughtful, high-end finishes. A sweeping entry leads past intimate outdoor living spaces centered around a dramatic floor-to-ceiling exterior fireplace, perfect for cool evenings and quiet reflection. Step inside to discover warm, curated interiors where a matching floor-to-ceiling indoor fireplace anchors a cozy great room...an ideal focal point for gatherings and quiet nights in. The custom kitchen is a chef's and designer's showcase making meal prep effortless and stylish. Cute, artful decor and exceptional millwork accentuate every room..every little detail has been considered and executed with eye-popping precision. Natural light pours through thoughtfully placed windows, highlighting textures, finishes, and curated vignettes around nearly every corner. In addition to the four private bedrooms, the special loft above the second-floor den offers a "fun" sleeping area and great retreat for the "kids". Unique sightlines and charming nooks reveal something special at every turn.unexpected architectural details, refined accents, and cozy gathering spots create a home rich in personality and comfort. The floorplan flows intuitively while offering distinct spaces for entertaining and everyday living. Practicality meets luxury with a spacious second garage providing room for toys, workshop space, or secure storage perfect for multi-vehicle households or hobbyists. The gated setting ensures peace of mind and exclusivity, while the manicured wooded grounds offer a serene backdrop and a strong connection to nature. Only 10 miles from world-class skiing at Okemo and golf at Fox Run...then enjoy the 5 lakes of Okemo Valley and the nearby VAST trails! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour