$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: 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.

$525,000 $228 per sq.ft. Cavendish VT Home »

6 Beds | 2 Baths |   Total Sq. Ft. 2304  |  Acres: 0.37
Thursday May 1, 2025
Description: This 1850s renovated property located right in the heart of the village adapts perfectly to your lifestyle or investment goals. This home functions seamlessly as a spacious 5-bedroom, 2-bathroom home or is ready to operate as two separate income-generating rental units. The unfinished third floor can easily be converted into additional living space, a master suite, or a bonus room. The spacious attached barn offers incredible storage. This property is just steps away from the local post office and village park and is located just minutes from Okemo Mountain Resort, making it a perfect Winter getaway or a lucrative Airbnb. Quick, direct access to Interstate 91 simplifies travel. See MLS Property & Listing Details & 27 images.

Under Contract Cavendish VT Home for sale $$599,000 $193 per sq.ft.

$599,000 $193 per sq.ft. Cavendish VT Home »


Price Change! Reduced by $125,000 down 21% on July 10th 2026
4 Beds | 3 Baths |   Total Sq. Ft. 3100  |  Acres: 44.9
Thursday May 8, 2025
Description: Seller relocating....price reduced. Their loss is your find! Winter, Spring, Summer or Fall, this is a bit of heaven for the nature lover! Located on the corner of two quiet, town maintained, gravel roads, one of which is a dead end, is the handsome 1800 traditional Cape with two additions! This classic home includes 40+ acres. Only one other house can be seen from the property & you have to know where to look! The back yard has lawn area with room for games, gardens or pets. When you are peering out any of the windows toward the back of the house you overlook a giant pond and wetland, home to a terrific assortment of wildlife. Head out to paddle & bring your binoculars! The home offers so much. You will enjoy the family room with high ceilings & great shelving for your collections. There is a more formal living room & dining room along with a very nice L-shaped kitchen. There are 2 bedrooms down & 2 bedrooms up. 2 full baths & 1 three quarter. Above the garage there is a large bonus room & a huge studio...currently a music studio, but it could be a great for exercise, artwork, craft space, play space, or even your office. Just about everything you see in the pictures is included in the sale...furnished & ready for you. Super location with Okemo in one direction passing by Singleton's store, Knapp Pond State Wildlife Area or Ascutney Outdoors for hiking, biking, skiing or tubing in another. Walk, run or bike to your heart's content on the backroads. This home and property is absolutely perfect for those seeking peace and tranquility! See MLS Property & Listing Details & 51 images.

New Listing! Cavendish VT Home for sale $$600,000 $282 per sq.ft.

$600,000 $282 per sq.ft. Cavendish VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 2128  |  Acres: 1.2
Friday Aug 7, 2026
Description: Welcome to this charming, easy-care country home nestled on a private road in the heart of Cavendish, Vermont. Offering 4 bedrooms and two bathrooms, this inviting property combines comfortable living with the peaceful beauty of its natural surroundings. A covered front porch welcomes you into the foyer, where you'll immediately appreciate the open-concept floor plan designed for everyday living and effortless entertaining. The spacious living room features a cozy gas fireplace and flows seamlessly into the dining area, where a sliding glass door opens to the side deck, creating the perfect indoor-outdoor gathering space. The well-appointed updated kitchen overlooks the living and dining areas and features a center island, making meal preparation and conversation easy. The main level also includes a primary bedroom and a three-quarter bathroom, offering flexibility for office space or one-level living. Upstairs, you'll find three bedrooms and a full bathroom complete with a relaxing soaking tub. Outside, enjoy the tranquility of Vermont living with a level front yard, beautifully maintained gardens, and a spacious deck surrounded by nature. A covered front porch provides the perfect place to unwind on warm summer evenings, while the 3-sided carport offers added convenience year-round. The basement is ready to finish with egress-rated windows and bathroom drains plumbed, creating a great upside to increasing value! This home has a five-star energy rating. Located near Okemo Mountain and minutes from local schools, Singleton's General Store, the Cavendish Town Green, and several local restaurants, this home offers the perfect balance of country privacy and small-town convenience. Whether you're searching for a full-time residence or a Vermont retreat, this property is ready to welcome you home. (This house has a septic rated for 12 people!) See MLS Property & Listing Details & 42 images.

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

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.

New Listing! Cavendish VT Home for sale $$995,000 $511 per sq.ft.

$995,000 $511 per sq.ft. Cavendish VT Home »

5 Beds | 4 Baths |   Total Sq. Ft. 2893  |  Acres: 2
Wednesday Aug 19, 2026
Description: Exceptional Vermont Log Home on 2+ Acres with Mountain Living Appeal. Meticulously maintained and beautifully landscaped, this stunning five-bedroom, four-bath log home offers the perfect blend of rustic charm, modern comfort, and exceptional amenities. Set on 2+ private acres, the property features covered porches, a relaxing hot tub deck, stone patio, and expansive outdoor spaces designed for enjoying every season. Inside, the main level welcomes you with a spacious kitchen that flows seamlessly into the large dining area and cozy office nook. The impressive 29' x 16' family room showcases a dramatic floor-to-ceiling wood-burning fireplace, creating a warm and inviting gathering space. Oversized windows throughout fill the home with natural light and frame the beautiful views. The upper level features a private primary bedroom with en-suite bath, two additional guest bedrooms, and a ¾ bath. The lower level offers flexible living space with both interior stairs and walkout access, including a generous mudroom, entertainment area with built-ins, two additional bedrooms, a ¾ bath, laundry area, second oven, and mechanical room. You can navigate the developed trail system on foot or four wheeler, snow-shoe across rolling pastures; or snowmobile with direct VAST Trail access.The heated garage/workshop has a concrete floor, forced hot air furnace and plenty of storage, ideal for projects or recreational equipment. Recent updates include a new Buderus boiler, water heater, and well pump in 2023. All three buildings feature durable standing seam metal roofs. With its exceptional craftsmanship and peaceful setting, this remarkable log home is a rare opportunity to enjoy the best of Vermont living. Less than 15 minutes to Okemo!!! This turn-key property is offered "mostly" furnished. See MLS Property & Listing Details & 51 images.

Under Contract Chester VT Home for sale $$549,000 $223 per sq.ft.

$549,000 $223 per sq.ft. Chester VT Home »

Waterfront on Pond
4 Beds | 3 Baths |   Total Sq. Ft. 2464  |  Acres: 2.13
Wednesday Apr 29, 2026
Description: Set along a quiet country road, this inviting 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and Vermont charm. The open-concept layout features high ceilings and abundant natural light, creating a warm, airy feel throughout. A spacious primary suite includes a jetted tub and walk-in closet, providing a true retreat at day's end. Step outside to a sunny, open lot with a peaceful pond, expansive deck ideal for entertaining, and a handsome shed for storage or hobbies. A recent fresh coat of interior paint and a newer high-efficiency boiler add modern reliability and make this home move-in ready. The large unfinished basement offers excellent potential for additional living space, a home gym, or a workshop. Ideally located near Okemo, Magic, and Stratton Mountains, with easy access to local dining, shops, and year-round recreation. This in a truly special location that is both private and practical. See MLS Property & Listing Details & 47 images.

New Listing! Chester VT Home for sale $$610,000 $320 per sq.ft.

$610,000 $320 per sq.ft. Chester VT Home »

4 Beds | 2 Baths |   Total Sq. Ft. 1908  |  Acres: 12.86
Monday Aug 24, 2026
Description: Tucked away on a quiet country road, this well-maintained 4-bedroom Cape home offers the peaceful Vermont setting so many buyers are searching for. Set on 12.86 acres, the property has been a place where generations have gathered, and now it's ready for its next chapter. Thoughtfully updated and meticulously cared for, the home features a new roof along with numerous improvements that provide confidence and convenience for years to come. Inside, the practical floor plan includes a desirable first-floor primary bedroom and first-floor laundry, making everyday living comfortable and accessible. The remaining bedrooms offer flexibility for guests, a home office, hobbies, or creative space. Step outside to enjoy beautifully landscaped grounds, a spacious deck built around an above-ground pool, and the quiet surroundings that define rural Vermont living. Multiple barns and sheds provide exceptional versatility, whether you're looking for a workshop, tractor or recreational vehicle storage, equipment space, or even a former horse stall ready for new possibilities. Combining privacy, usable acreage, and a property that has been lovingly maintained over the years, this home offers the opportunity to enjoy country living without sacrificing comfort. Whether you're looking for room to spread out, space for projects, or simply a peaceful place to call home, this property is ready to welcome its next owners. See MLS Property & Listing Details & 47 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: 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. Come see how every corner captures your attention and inspires a sense of wonder at home. This mini-estate is 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

Under Contract Chester VT Home for sale $$789,000 $215 per sq.ft.

$789,000 $215 per sq.ft. Chester VT Home »


Price Change! Reduced by $60,000 down 8% on July 24th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 4388  |  Acres: 11.24
Wednesday Jul 1, 2026
Description: Exceptional design, enduring craftsmanship, and an unrivaled Vermont setting define this remarkable custom residence on 11± beautifully landscaped acres just a short stroll from the village of Chester. Offering more than 3,600 square feet of thoughtfully designed living space, the home was built to an exacting standard where quality materials, timeless architecture, and exceptional attention to detail create a residence as enduring as it is beautiful. A flexible floor plan offers five bedrooms and three baths, including an elegant first-floor primary suite with ensuite bath, complemented by additional main-level bedroom options ideal for guests, multi-generational living, or a dedicated home office. Upstairs, two spacious bedrooms each feature adjoining bonus rooms perfectly suited as executive offices, dressing rooms, studios, or generous walk-in closets, while additional unfinished space presents exciting opportunities for future expansion. Designed for effortless entertaining and comfortable everyday living, the heart of the home is an open-concept kitchen, dining, and living area filled with natural light. A handsome library offers a quiet retreat, while integrated whole-home audio enhances the experience throughout. An oversized laundry and mudroom connects seamlessly to the attached two-car garage, delivering exceptional convenience without compromising design. Outside, mature gardens, specimen trees, and thoughtfully curated outdoor living spaces create a setting of remarkable beauty and privacy. Relax beneath the covered porch, entertain with family and friends, or simply enjoy the peaceful surroundings. Ideally located just minutes from Okemo, Stratton, Magic, and endless four-season recreation, yet within walking distance of Chester's vibrant village, this exceptional property offers a rare combination of privacy, convenience, and refined Vermont living. A home of lasting quality, exceptional versatility, and unmistakable character! See MLS Property & Listing Details & 44 images.

$900,000 $321 per sq.ft. Chester VT Home »


Price Change! Reduced by $25,000 down 3% on August 13th 2026
5 Beds | 3 Baths |   Total Sq. Ft. 2800  |  Acres: 14.1
Tuesday Jul 14, 2026
Description: Escape to the charm of Vermont in this spacious 5-bedroom, 3-bath country home, perfectly set amidst open meadows with a picturesque swim pond and peaceful surroundings. Designed for both everyday living and entertaining, this inviting property offers the perfect balance of rustic character and modern comfort. Step inside through the practical mudroom, where you'll be welcomed by a dramatic family room featuring soaring vaulted ceilings, a cozy wood-burning stove, and a loft overlooking the space. The heart of the original 1860's home is the open-concept living area, complete with a well-appointed kitchen, dining area, and a warm, inviting living room centered around a classic wood-burning fireplace. The main level also features a convenient half bath and a private primary suite with a ¾ bath. From the primary bath, step directly onto the back deck and unwind in the sunken hot tub while taking in the tranquil country setting. Second level, you'll find four additional bedrooms, a full bath, and a comfortable den/loft overlooking the family room, offering flexible space for guests, a home office, or recreation. Outside, enjoy Vermont's beauty from the private covered porch, gather around the expansive yard, or relax by the stone firepit or scenic pond surrounded by open meadows. An attached garage provides ample storage, while the finished game room above creates the perfect space for entertaining, hobbies, or additional guest accommodations. The flat meadows were the perfect setting for the family's recent wedding... What event will you host in this incredible backyard? Ideally located just minutes from the charming village of Chester and within easy reach of Okemo Mountain Resort, this exceptional property offers year-round enjoyment, whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity. Visit the Okemo real estate community today. Taxes are based on town assessment. See MLS Property & Listing Details & 58 images.

$579,000 $229 per sq.ft. Chittenden VT Home »


Price Change! Reduced by $80,000 down 14% on August 26th 2026
Waterfront on River East Creek
4 Beds | 2 Baths |   Total Sq. Ft. 2532  |  Acres: 1.2
Thursday Jun 18, 2026
Description: Must see, new price! Welcome to 275 Chittenden Road, a classic Vermont Farmhouse fully refinished set on 1.2 level acres with frontage along East Creek. Offering 4 bedrooms, 2 full baths, and 2,532 finished square feet, this 1850 home blends historic charm with warm, updated living spaces and flexible options for today's lifestyle. This fully remodeled home from the studs must be seen in person to fully enjoy. Featuring exposed beams, refinished wide plank wood flooring, tiling in the kitchen and all baths no detail was missed. The additional rec room with vaulted ceilings offers the space for all of your entertaining needs. The kitchen is well appointed with marble countertops and attached dining. Step onto the screened in seasonal porch to enjoy the sound of the East Creek rolling by. Enjoy single level living with a bedroom, bath and laundry on the main floor. The property also includes a versatile accessory unit with one bedroom, its own kitchen, and a living room, offering excellent flexibility for guests, extended household needs, a private work-from-home setup, or other uses subject to local approvals. Outdoor living is just as inviting, with a covered porch, screened porch, open yard space, and the sights and sounds of the creek. Located in scenic Chittenden, Vermont, this Rutland County setting is known for its peaceful rural character and access to year-round recreation. Enjoy proximity to hiking, fishing, snowshoeing, within 30 minutes of skiing, Chittenden Reservoir, Chittenden Brook, and the broader Green Mountain region, while still having local conveniences and nearby Rutland-area amenities within reach. This home has it all, nice finishes, low maintenance with heating systems and electrical all updated, beautiful landscaping, porches and decks to enjoy, a beautiful flowing creek in the back yard and flexibility in living accommodations. The property is offered fully furnished less a few personal items. This is a must see to fully appreciate! See MLS Property & Listing Details & 60 images. Includes a Virtual Tour

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