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


Price Change! Reduced by $125,000 down 21% on July 10th 2026
Waterfront on Pond _Unnamed
4 Beds | 3 Baths |   Total Sq. Ft. 3100  |  Acres: 44.9
Listed on 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 Listing Details & 51 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.

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

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

4 Beds | 3 Baths |   Total Sq. Ft. 2464  |  Acres: 2.13
Listed on 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 Listing Details & 47 images.

$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.

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

3 Beds | 2 Baths |   Total Sq. Ft. 2204  |  Acres: 1
Listed on 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 Listing Details & 60 images. Includes a Virtual Tour

Under Contract Chester VT Home for sale $750,000 $442 per sq.ft.

$750,000 $442 per sq.ft. Chester VT Home »

Waterfront on River Williams River
3 Beds | 2 Baths |   Total Sq. Ft. 1695  |  Acres: 6.03
Listed on Wednesday Jul 1, 2026
Description: Tucked away on a quiet country road in one of Chester's most coveted areas, this striking contemporary home offers the ultimate Vermont lifestyle, just miles from the Okemo Mountain base lodge. Embraced by nature and thoughtful landscape, the property seamlessly connects refined indoor living with the natural beauty of its private riverfront, complete with your own summer swimming hole. Inside, the main level centers around a commanding, floor-to-ceiling fieldstone wood-burning fireplace, beautifully complemented by rich hardwood floors and a bespoke custom kitchen. Designed for privacy, the primary suite features a spa-like ensuite bath, while two additional guest bedrooms and a 3/4 bath provide plenty of space for family or weekend visitors. Intelligently designed for flexible living, the upper-level loft serves as an inspiring home office or studio, while the bright, walk-out lower level offers incredible potential for a game room, home gym, or ski lounge. Transition effortlessly outdoors to the oversized front deck for morning coffee, or unwind in the expansive screened porch out back listening to the sound of the river. The detached, insulated, oversized, 2-bay, 2-level barn has full electrical service, electric garage doors, and a workshop with extra storage space. There is a greenhouse perfect for gardening. With direct access to nearby VAST trails for winter recreation, this is a true four-season retreat. Visit the Okemo real estate today. Taxes are based on the current town assessment. See Listing Details & 59 images.

$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
Listed on 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 Listing Details & 44 images.

$925,000 $325 per sq.ft. Chester VT Home »

5 Beds | 3 Baths |   Total Sq. Ft. 2850  |  Acres: 14.1
Listed on 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 Listing Details & 58 images.

$625,000 $247 per sq.ft. Chittenden VT Home »


Price Change! Reduced by $34,000 down 5% on July 23rd 2026
4 Beds | 2 Baths |   Total Sq. Ft. 2532  |  Acres: 1.2
Listed on 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 Listing Details & 60 images. Includes a Virtual Tour

$599,000 $358 per sq.ft. Clarendon VT Home »

3 Beds | 3 Baths |   Total Sq. Ft. 1672  |  Acres: 17
Listed on Friday Jul 3, 2026
Description: Some properties simply have to be experienced in person to be fully appreciated, and this is one of them. This charming 3-bedroom, 2.5-bath Cape sits on 17 breathtaking acres where sweeping views, a spring fed pond, mature fruit trees, blueberry bushes, and beautifully maintained grounds create an exceptional setting. The property also includes two outbuildings, including a classic barn with hayloft and stalls. A second outbuilding features upper- and lower-level garage bays, ideal for equipment, ATVs, tractors, workshop space, or additional storage. Inside, the eat-in kitchen features a large picture window overlooking western views and stunning sunsets. It flows into the living room with a cozy wood-burning fireplace and sliding glass doors leading to the back porch, the perfect spot to enjoy the sunrise. A half bath with laundry is located just off the kitchen, while the first-floor primary suite offers a walk-in closet and private en suite bath. Upstairs are two generously sized bedrooms, each with a closet, and an additional full bath. The walk-out basement offers excellent potential for future expansion and already includes a roughed-in bathroom. A two-car attached garage completes the home. Enjoy the tranquility of country living without sacrificing convenience. Located just outside of Rutland, the property is close to shopping, dining, and healthcare, and only 30 minutes from Okemo and Killington/Pico for year-round recreation. See Listing Details & 42 images.

Under Contract Clarendon VT Home for sale $600,000 $238 per sq.ft.

$600,000 $238 per sq.ft. Clarendon VT Home »

2 Beds | 3 Baths |   Total Sq. Ft. 2520  |  Acres: 9
Listed on Friday Feb 27, 2026
Description: Welcome Home to Vermont Living at Its Finest. Perched in the rolling hills of North Clarendon, this charming 2-bedroom, 2.5 bathroom home delivers a unique blend of rich character and modern comfort that's hard to find. Step inside to discover radiant flooring that keeps your toes warm while the snow piles up outside. The first floor features unique office spaces or could be converted as two additional bedrooms. The well-appointed kitchen serves as the heart of the home with top of the line cupboards and stainless steel appliances. An open floor plan to the main living room, dining area and a flex room enhanced by a wood burning fireplace overlooking long-range views from either inside or step out on the huge deck to bask in the sun. The primary bedroom has its own bath, second bedroom and full bath right next door. A full basement houses the utilities with some framing already started to add more rooms below grade. Outside, the generous lot provides room to breathe, garden, or simply watch the seasons paint the landscape in every color imaginable. A spacious three-car garage accommodates vehicles, toys, and all the gear that Vermont living demands with 17' ceilings with steal beam construction. The neighborhood places you minutes from MRUHS, convenient shopping at Green Mountain Shopping Plaza, and easy access via Route 4 Bypass. Adventure seekers will love the proximity to both Killington Ski Area and Okemo Mountain Resort. See Listing Details & 51 images.

$659,000 $232 per sq.ft. Clarendon VT Home »

4 Beds | 4 Baths |   Total Sq. Ft. 2840  |  Acres: 7.01
Listed on Monday Jun 1, 2026
Description: This lovely Craftsman-designed one-level, 2,800 square foot home feels as though it belongs in La Cottage magazine. Built in 1982 and lovingly maintained by the same family for 32 years, this special property has been the backdrop for a lifetime of memories. Set on seven beautiful acres in Clarendon, Vermont, the property offers privacy, perennial gardens, a large spring-fed pond, and a three-car garage. The pond has been the centerpiece of countless summers, with children spending endless hours swimming, fishing, and playing from the floating dock that has provided years of fun and laughter. Inside, the home features four bedrooms and four baths, including a primary suite with a private bath, a guest bedroom, and two bedrooms connected by a charming Jack-and-Jill bath. A dedicated home office provides the perfect space for today's lifestyle. The heart of the home is the expansive great room, where oversized windows bring the outdoors in and create a screened-porch feel during the warmer months. Oak hand-pegged flooring, a pellet stove, and a mini split system provide warmth, character, and comfort throughout the seasons. Thoughtful details and quality craftsmanship throughout reflect the timeless appeal of the Craftsman style. Step outside and you'll discover a setting that is truly one of a kind. A gazebo overlooking the pond offers the perfect place to relax, entertain, and create your own lasting family traditions. The perennial gardens are simply stunning, reminiscent of a Martha Stewart magazine, with colorful blooms and thoughtful landscaping at every turn. The full basement features high ceilings and offers tremendous potential for additional living space, recreation areas, or storage. Rarely does a property combine such charm, character, acreage, and recreational enjoyment in one beautiful package. Centrally located between Manchester and Rutland for shopping, dining, and minutes to both Killington and Okemo ski areas. LIVE VT. See Listing Details & 37 images. Includes a Virtual Tour

© 2000-2026 Clerkin Agency Real Estate
NEREN Logo
565 Maple Street, White River Junction, Vermont. 05001 802-295-1355
Copyright © 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated August 1st, 2026

PLEASE NOTE: Both New Hampshire and Vermont law require brokers and agents to disclose at the “time of first business meeting, prior to any discussion of confidential information”, in New Hampshire’s case, and “first reasonable opportunity”, in Vermont’s case, the nature of the relationships brokers have or may have with customers and clients. Each state requires that a disclosure form be presented to consumers for their review and acknowledgment at the appropriate time. These forms can be accessed here:
VT: VERMONT REAL ESTATE COMMISSION MANDATORY CONSUMER DISCLOSURE FORM
NH: NEW HAMPSHIRE REAL ESTATE COMMISSION BROKERAGE RELATIONSHIP DISCLOSURE FORM