Area Homes $350-$500k

MLS Number 5026224

• Residential Single Family
• Full Bath 2
• Address 5534 Route 100
• Construction Existing
• Bedrooms 3

Attention Skiers and Snowmobilers! This newly updated, open concept 3 bedroom plus den, 2 full bathroom vacation retreat is minutes to Killington, Okemo or Woodstock. Conveniently located off of scenic Vermont Route 100 on 7.9 +/- acres with direct access to VAST Snowmobile Trails from the property. The property is situated across the street from Chloe's Market/ Plymouth Country Store to walk and enjoy gourmet coffee, treats, deli sandwiches, pre-made meals, and more. Wonderful open concept floor plan ideal for entertaining with loads of light and wood floors throughout. New front entry mudroom flows into a new renovated kitchen and brand-new pantry with stainless appliances and counters. After a day of outdoor play, kick back in the open great room and dining area. Cozy up next to the double-sided floor to ceiling fieldstone fireplace hearth with woodstove insert. Family and friends will love the recreation den room with a wall of sliding glass doors that lead you out to a cool deck to enjoy a drink on a summer evening. Close to world class skiing and golf, endless hiking/mountain biking trails, and pristine lakes. The property has an outdoor toy/snowmobile shed plus a one car detached garage. Strong rental potential here! Excellent short term investment opportunity in the heart of ski and snowmobile country. Zoned Residential and Commercial. Come check this one out!

Listed by Marni Rieger of KW Vermont-Killington

MLS Number 5026063

• Condo
• Square Feet 640
• Bedrooms 1
• New Contruction Existing
• Complex Okemo Mountain Lodge

Okemo Mountain Lodge! This charming condo with amazing mountain views is located at 109 Okemo Ridge Rd, C Bldg, 3rd floor, Unit 301 at Okemo, VT. It was built in 1984 and is one of only four units with an extra room which is currently furnished as a 2nd bedroom. Highlighted features include a breakfast bar, ski locker, and outside deck with a great view up the slopes. It includes a large living room with a new electric FP, dining area and breakfast bar. The property boasts a convenient location as an end-unit overlooking the double quad chair at Okemo Mountain, making it an ideal spot for avid skiers or outdoor enthusiasts. This unit is located next door to the Clock Tower Base Lodge, near the cafeteria, ski shop, day care, magic carpet, The Bull Lounge and close to the famous Loft bar. Parking is in a lot adjacent to the condo bldg. In the summer you can enjoy mountain biking, the lakes region (5 min. away), summer concerts & festivals just to name a few. HOA fees include heat, parking, Wi-Fi, cable, trash, and snow removal. Taxes are based on current town assessment.

Listed by Derek Greene of Derek Greene

MLS Number 5025998

• Residential Single Family
• Full Bath 1
• Address 191 Melody Lane
• Construction Existing
• Bedrooms 2

First time on the market and ready for new owners. Sitting on a quiet country road just 5 miles from Rt 91, is a lovely 2+ bedroom, 2 bath home on 3.13 acres with a 2 story 2-car garage. Enter the home through the mudroom into the kitchen with granite countertops and lots of storage. A large living/dining room with a pellet stove is open to the kitchen. A three season porch/sunroom looks over the peaceful backyard. A formal living room with wood fireplace, a full bathroom off the hall with stackable laundry and a clawfoot tub, a primary bedroom suite with a 3/4 bath, and a second bedroom finishes off the first floor. There are an additional 2 rooms in the finished second floor/attic space. A partially finished basement with a rec room, laundry room, and workshop spaces provide ample additional space for storage and hobbies. The home sits on a total of 3.13 acres which is made up of two lots. The home is on the 2 acre lot and there is an additional 1.13 acre lot that could be kept for a buffer or could be built on. There is a 2-story 2 car garage, a chicken coop and two additional sheds in the backyard. Conveniently located 40 minutes south of DHMC and the Upper Valley, 20 minutes from Harpoon and Simon Pearce Glass in Windsor, less than 40 minutes to Okemo Mountain or Mt. Sunapee, 15 minutes to Mt. Ascutney mountain biking trails and state park area. Delayed showings begin Friday, Jan 10, 2025. Make an appointment Fri, Jan 10 from 1-3pm or Sat, Jan 11 from 10am-1pm.

Listed by Amy Hill of EXP Realty

MLS Number 5024984

• Condo
• Square Feet 1,228
• Bedrooms 2
• New Contruction Existing
• Complex Okemo Trailside

Privately located two bedroom, two bath Okemo Trailside condominium just steps from the Sachem ski trail. Wonderful year round retreat. Enjoy long distance mountain views and ski slope access in the winter, private wooded setting with path leading to the swimming pool and tennis courts in the summer. Nicely updated. Kitchen with painted cabinets, stone countertop, wood floors, and tiled backsplash with breakfast bar. Separate dining area. Living room with skylit cathedral ceiling leading to a new deck with easterly exposure. Main level bedroom with open beamed high ceilings. Loft bedroom suite includes full bath, walk in closet, and laundry. Entry mudroom with rough sawn pine paneling and numerous built ins.

Listed by Andre Menard of Mary W. Davis Realtor & Assoc.,Inc.

MLS Number 5024631

• Residential Single Family
• Full Bath 1
• Address 96 S. Main Street
• Construction Existing
• Bedrooms 4

This spacious 1800's home is filled with Vermont charm and located in the heart of Chester. Filled with natural light from newly installed windows, the home boasts beautiful wood floors throughout and antique door handles that capture the essence of the era. Spacious bedrooms provide ample comfort, while smart thermostats ensure modern convenience. A newly built, covered front porch welcomes you into the home, and a deck off the kitchen leads to an open, level backyard-perfect for gardening or outdoor activities. One of the standout features of this property is the versatile studio space. Accessible via its own entrance from Main Street, this expansive area features vaulted ceilings and two half baths, offering endless possibilities. Whether you're looking to create a storefront, set up an at-home business, or convert the space into a private apartment, the potential is limitless. This property offers a unique opportunity to live in a quintessential Vermont town while having the flexibility to tailor the space to your needs. It's a must-see for anyone seeking a charming, functional home with potential for growth!

Listed by Jessica Citera of Cummings & Co

MLS Number 5024148

• Residential Single Family
• Full Bath 1
• Address 102 Church Street
• Construction Existing
• Bedrooms 4

A classic, easy maintenance four bedroom, two bath home in Chester village on .12 acres +/-, within walking distance to the Village Green for summer concerts, restaurants and shopping. The front porch is a focal point and a great way to meet your neighbors and passersby on the walking loop. The first floor features a large foyer, spacious living room, large dining room with corner built-in and elegant lighting, a country kitchen with marble tile flooring, first floor bath with tiled shower and an adjoining bedroom with a lovely reading/entertainment nook that connects with the dining room. The second floor has a large landing with two adjoining bedrooms, a full bath with radiant heat in the floor and a cool, private back bedroom. The basement has foam insulation and the windows, water heater and oil tank have been replaced. Ready for your enjoyment as primary, secondary or investment property. Close to Magic, Okemo, Bromley and Stratton Resorts, and year year-round recreational activities.

Listed by Geralyn Donohue of Engel & Volkers Okemo

MLS Number 5023780

• Residential Single Family
• Full Bath 3
• Address 196 North Street
• Construction Existing
• Bedrooms 3

The Simeon Sherwin House, built in 1844, is one of three look-alike houses known as "Three Sisters". The house was owned by Olivia Goldsmith in the 1990's who wrote The First Wives Club. Her worldly, vibrant imprint is still evident in many of the home's unique features. Architecturally, the stone exterior is unique with large blocks (quoins) of schist and mica at the corners. Inside, there is a delightful three season sunroom and formal dining room with woodstove insert, chandelier and an array of full light doors which open to the large, bright kitchen and first floor full bath. A sitting room with a double-sided fireplace connects to the spacious living room. The inviting foyer leads to the second floor which features 3 bedrooms, 2 baths and a sitting room. An addition added by the author and named the Queen's Room during the current owners bnb tenure features built-ins, a partition wall with transom window and a wood stove insert flanked by cozy built-in seats. The primary bath features gold-plated fixtures, a skylight and soaking tub. The first floor also has a heated, retail space for a home business with a separate entrance and office above that has served as an antique shop. The two-car attached, garage has unfinished, overhead space. The exterior needs some sprucing up and a new owner will want to add cosmetic upgrades. The property on .70 acres has a lovely yard with a hydrangea bush, charming bridge, small pond and stone bench overlooking the picturesque village.

Listed by Geralyn Donohue of Engel & Volkers Okemo

MLS Number 5023047

• Residential Single Family
• Full Bath 2
• Address 37 Cootey Lane
• Construction Existing
• Bedrooms 3

Delightful well maintained home tucked away on 1.17+/- acre lot. 3 bedroom, 2.5 bath and a full basement. The fully applianced kitchen with a center island offers extra space for cooking, dining area with sliders leading out to the back yard makes it convenient for backyard bbq's. Off from the kitchen is the living room with built-ins enhanced by a propane fireplace. A formal dining room borders the kitchen with a passthrough for food. Upstairs offers three bedrooms including a large primary bedroom and bath. Spacious backyard with an above ground swimming pool for summer fun and a shed. Just minutes to Killington Ski area or Okemo Mountain for some of the best skiing in New England.

Listed by Nancy Greenwood of Watson Realty & Associates

MLS Number 5021332

• Condo
• Square Feet 884
• Bedrooms 1
• New Contruction Existing
• Complex Okemo Trailside

Spacious one bedroom plus oversized bunkroom Okemo Trailside unit steps to trail and community amenities. Redesigned kitchen with breakfast bar includes stainless steel appliances, updated countertops, cabinetry, fixtures, and flooring. Separate dining area with updated lighting. Sunken living room with fireplace and laminated flooring leading to outdoor patio space through an updated slider with long distance winter views. Bath offers many updates including radiant heat, oversized shower with rainspout shower head, tile floor, and updated cabinetry and fixtures. Mudroom includes built-ins and offers easy access to private exterior ski closet. Exterior siding and roofing have been recently completed.

Listed by Andre Menard of Mary W. Davis Realtor & Assoc.,Inc.

MLS Number 5020855

• Residential Single Family
• Full Bath 1
• Construction Existing
• Bedrooms 4
• Bathroom 4

Nestled in the scenic town of Bridgewater, Vermont, just 9 minutes from Killington Ski Resort and 25 minutes from Okemo, this charming 2-unit single-family home on 1 acre is a unique mountain retreat and a proven rental success. One of the standout features is the thoroughly renovated first-floor kitchen, which boasts elegant marble countertops and ample counter space, perfect for cooking family dinners and creating a relaxing Family or Airbnb experience. The large front porch invites you to savor morning coffee while enjoying breathtaking views and watching the sunrise. The updated wood paneled bathroom brings the area excitement inside with a claw tub and walking shower. The home continues to impress with a cozy loft on the second floor and a captivating tower room on the third floor that offers stunning 360-degree views of the surrounding landscape. Permitted for 4 bedrooms, this generator-ready home is configured as a 2-unit residence, providing flexibility for family living or guest accommodations. Its successful Airbnb history highlights its appeal to visitors seeking comfort and convenience in a beautiful setting. Additionally, there's potential for expansion with an accessory dwelling unit (ADU) at a clearing atop the hill. Set on a spacious lot amidst Vermont's natural beauty, this property combines mountain-town charm with immediate access to recreation, making it an inviting retreat and a solid investment opportunity.

Listed by Jeremy Collins of Ridgeline Real Estate

MLS Number 5018404

• Residential Single Family
• Full Bath 2
• Address 410 Route 100 S
• Construction Existing
• Bedrooms 4

Located in the heart of Ludlow, this home is a four-season retreat, with Okemo Mountain Resort offering world-class skiing in the winter and mountain biking, hiking, and golfing in the summer. This home is less than 2 miles from Okemo and right on the VAST trail. The vibrant village of Ludlow offers quaint shops, excellent dining, and a welcoming community atmosphere, all just a short drive away. While this home is move-in ready, it could benefit from some minor updates, allowing you to truly make it your own. Whether it's refreshing the paint or some new fixtures, adding your personal design touches, a few updates will enhance its charm and value, giving you the chance to put your own stamp on it. Don't miss out on this rare opportunity to own a piece of paradise in one of Vermont's most sought-after ski towns! Welcome Home

Listed by Noel Weeks of Welcome Home Real Estate

MLS Number 5017155

• Residential Single Family
• Full Bath 1
• Address 69 Pleasant Street
• Construction Existing
• Bedrooms 3

Discover the charm and convenience of village living with this delightful 3-bedroom, 2-bathroom fully furnished home, offering views of Okemo Mountain. The main level contains a kitchen, 3/4 bathroom, a dining room, a bedroom, and a living room with mountain views. Upstairs you'll find a full bathroom with two more bedrooms. The home boasts a welcoming covered front porch, perfect for relaxing and soaking in the mountain views. The spacious fenced-in yard provides a private oasis for outdoor gatherings, pets, or gardening, while the proximity to local shops, restaurants, and amenities makes daily errands and dining out a breeze. This Ludlow Village home offers comfort and ease for vacationers and year-round residents. Ideally situated on the Okemo shuttle route, your winter adventures are just moments away. This property combines the best of mountain living with village convenience. Don't miss the opportunity to make this your base for all-season enjoyment. Visit the Okemo real estate community today. Taxes are based on current town assessment.

Listed by Katherine Burns of William Raveis Vermont Properties

MLS Number 5016501

• Residential Single Family
• Full Bath 1
• Address 948 High Street
• Construction Existing
• Bedrooms 3

If you're looking for one level floor living, on a beautiful, serene country lot, well, here you go! This fabulous, updated 7 room ranch with a 2 car attached garage welcomes you to Cavendish! This home features 3 great sized bedrooms, 2 baths with one bath in the master bedroom. The Kitchen has a new gas inset for the fireplace, all ready to help to take the chill out of the early mornings. The kitchen also has seen additional renovations that include cabinets, and new stainless-steel appliances. The roof is new, windows new, mostly all new interior doors, pellet stove, hot water heater, generator with hookups throughout the home and the list goes on. Exterior includes a new 16x28 trex deck and a hot tub. The 24x24 barn has running water and power, and could be used as a barn, garage, man cave, she shed, workshop, studio? Ideas are endless. This is a very well maintain property, showing lots of ownership pride. All the new items are too numerous to mention. This 1-acre lot is level with landscaping including a rhubarb patch and blueberry trees. A Great yard for pets, children or gardens. Located just off of Route 131, with about 20 minutes to I91, 16 minutes to Okemo Mountain Resort and about 7 minutes to Ludlow. This property is a GEM, come take a peek!

Listed by Ann Jacques of Century 21 Highview Realty

MLS Number 5016226

• Residential Single Family
• Address 29 Markham Lane
• Construction Existing
• Bedrooms 2
• Bathroom 1

Charming 1940s Cottage in the Heart of Weston, Vermont Step into a slice of New England history with this quaint 1940s cottage, perfectly situated in the picturesque village of Weston. This home invites you to immerse yourself in the local culture, being just a short stroll from the renowned Weston Playhouse and the iconic Vermont Country Store. Enjoy lazy afternoons at the village green, surrounded by the charm of a historic grist mill and vibrant community life. While the cottage is in need of some tender loving care, this presents an incredible opportunity for you to transform it into your dream retreat. Imagine the possibilities as you design each room to reflect your personal style, all while preserving the unique character that only a vintage property can offer. Nestled in a community rich with tradition and natural beauty, you'll find yourself just minutes away from some of southern Vermont's premier ski areas, including Okemo and Stratton. Whether you're an outdoor enthusiast or a culture seeker, this location caters to all. This is more than just a property; it's a canvas awaiting your touch. With a little creativity and vision, this cottage could become a cozy year-round home or an enchanting getaway. Seize the chance to craft your own haven in this charming village, where history and community spirit thrive. Don't miss out on the opportunity to own a piece of Weston-schedule your viewing today and start imagining the possibilities!

Listed by Daire Gibney of Barrett and Valley Associates Inc.

MLS Number 5013943

• Condo
• Square Feet 1,428
• Bedrooms 3
• New Contruction Existing
• Year Built 1980

Ready to move in, all elegant furnished, everything included(furniture + all housing equipment), private cull-de-sac on top of Hawk Mountain Resort In between Okemo and Killington, with amaizing views of the sunset through the woods and mountain from all rooms. No special assessments, bottom of Hawk Mountain resort will have soon open a 5 star resort with facilities to benefit of(restaurant, pool, gym, entertainment rooms . Pristine maintained, never used for rental. o Enjoy views of the surrounding mountains and forest from your private balcony and expansive living area as well from main suite bedroom. Perfect for sunrise coffee or sunset cocktails. o Bonus, additional room on the second floor for possible extra storage or 4th bedroom easy to finish with local contractor. o Storage: Additional storage for outdoor gear and seasonal items. o Spacious Living: The open-concept living and dining area features large windows that frame the incredible views, while a cozy stone fireplace adds a touch of warmth and charm. o Modern updated appliances Kitchen: The fully-equipped kitchen boasts high-end appliances, amazing quality cabinets, making it a dream for both everyday meals and entertaining guests. o Master Suite: The luxurious master royal bedroom, all furnished includes a private balcony, an en-suite bathroom with a soaking tub, and a spacious closet. o Additional Bedrooms: Two additional bedrooms provide ample space for all, all furnished, each with its own unique view a

Listed by Ralph Harvey of Listwithfreedom.com

MLS Number 5010903

• Residential Single Family
• Full Bath 1
• Address 1739 Vt Route 140
• Construction Existing
• Bedrooms 3

This MOVE-IN Ready 3 Bedroom, 3 Bathroom Cape nestled in the mountains just outside of Wallingford Village and within walking distance to White Rocks National Park and the Long Trail. 15 minutes to Jackson Gore! Mixed hardwood floors and natural light throughout the first floor. New Quartz countertops in the kitchen and charming light fixtures sets this cape apart! High Ceilings in the upstairs bedrooms make this home feel cozy and spacious at the same time. A fenced in yard sits just off of the 3 season porch. Enjoy morning coffee in the Ladybug Lounge with electricity overlooking the brook into the neighboring meadow. A spacious detached 2 car garage with storage overhead. Heat Pump, Pellet stove, generator ready. Make this Cape your new home or Vermont getaway. 15 minutes to Okemo!

Listed by Mark Noble of Welcome Home Real Estate

MLS Number 5007992

• Residential Single Family
• Full Bath 1
• Address 15 Gill Terrace
• Construction Existing
• Bedrooms 4

Who doesn't love a stately home in Ludlow? This one is a classic with many craftsman details throughout. The fireplace is stunning and the summer sleeping porch on the second floor is something from years gone by. There are hardwood floors in almost every room and decorative panels on many walls. With 4 bedrooms, 2 baths, and some bonus rooms, there is plenty of room for family and friends. This home will need a renovation but the bones are good and can easily be brought back to its former glory. The home provides nice views of the village as well as the Green Mountain Range. It's just a short walk to many restaurants, shops, parks, and the Okemo free shuttle stop. The lot next door is for sale as well if you wish to enlarge your lawns. Visit the Okemo real estate community today. Taxes are based on current town assessments.

Listed by Kevin Barnes of William Raveis Vermont Properties

MLS Number 5006884

• Condo
• Square Feet 1,445
• Bedrooms 2
• New Contruction Existing
• Complex Castle Hill

Welcome to Castle Hill E-3, a charming and meticulously maintained two-bedroom plus den condo that perfectly balances comfort and style. This inviting end unit features a cozy den complete with a wet bar, ideal for relaxation and entertaining. Step inside to discover stunning wood flooring that enhances the warm atmosphere, complemented by elegant granite countertops, modern appliances, and a breakfast counter in the kitchen. Enjoy the convenience of ample outdoor space right at your doorstep, along with hassle-free parking. Nestled in a picturesque condominium community surrounded by the majestic mountains near the historic Castle Inn, listed on the National Register of Historic Places, Castle Hill offers an exceptional living experience. Take advantage of luxury resort amenities including two tennis courts, a year-round heated outdoor saltwater swimming pool and hot tub, and a full-service Aveda Health Spa and Fitness Center. Plus, indulge your taste buds at the award-winning Castle Inn Restaurant, located within the resort complex. Experience the perfect blend of luxury and tranquility at Castle Hill E-3, your ideal mountain getaway awaits!

Listed by Matthew Bellantoni of Mary W. Davis Realtor & Assoc.,Inc.

MLS Number 5005884

• Residential Single Family
• Full Bath 1
• Construction Existing
• Bedrooms 3
• Bathroom 2

Unique Chester property on 10.08+/- acres with home business potential! This 3 bedroom, 1.5 bath Contemporary has lovely grounds that feature a pond, landscaped rock gardens, a vegetable garden and ample open space for more gardening endeavors. The detached 3-bay garage offers multiple large spaces and oversized doors. Whether you are an artist, contractor, carpenter or mechanic, the high ceilings and huge amount of work space will be appreciated. Set back from the road with plenty of parking area, there is room to add more outbuildings for business needs. The efficient house features a cozy living room, first floor bedroom, full bath and kitchen/dining that opens to the back deck overlooking the private pond. The second floor has a large common area adjoined by two bedrooms and a half bath with laundry. The whole house generator and Fiber Optic internet service will keep your systems and business running during power outages. Commutable to the Upper Valley, convenient to Springfield, skiing, shopping, Chester Village and all the area has to offer.

Listed by Geralyn Donohue of Engel & Volkers Okemo

MLS Number 5000203

• Residential Single Family
• Full Bath 2
• Address 491 Farrar Road
• Construction Existing
• Bedrooms 4

Nestled on a serene, quiet town maintained dirt road, this spacious home offers the perfect blend of tranquility and comfort. As you approach, you'll be captivated by the stunning long-range views that greet you from the expansive deck, a haven for relaxation and outdoor enjoyment. The deck overlooks a picturesque pond, not on the property but offering a beautiful, calming view that enhances the natural charm of the setting all the same. Step inside to discover a thoughtfully designed interior where ample space meets cozy. The large, finished basement is a true bonus, featuring a cozy and convientent propane stove and serving as an ideal games room or entertainment space for family and friends. Featureing 4 large bedrooms, 3.5 bathrooms, with large primary ensuite, large living room with views and that all enticing party or craft space in the below. This is equally a perfect vacation retreat or spacious family home. Conveniently located close to the popular ski areas of Okemo, Stratton, and Magic this home is perfect for winter sports enthusiasts. Whether you're seeking a peaceful year-round residence or a seasonal getaway, this property promises a lifestyle of serene beauty and endless recreational opportunities. Welcome home to your personal oasis.

Listed by Daire Gibney of Barrett and Valley Associates Inc.