Investment Properties

MLS Number 5076203

• Residential Single Family
• Full Bath 1
• Address 563 Rim Road
• Bedrooms 4
• Bathroom 5

The Queen's Croft-A Luxurious 4-Bedroom, 5-Bath Custom Vacation Home less than 2 miles to Bear Mountain. Built in 2007 and spanning three beautifully finished levels, this fully furnished and equipped 4,000 sq ft custom home offers the ideal blend of luxury, comfort, and convenience. The property features many thoughtfully designed rooms, and high quality details like heavily-insulated 2x6 construction, 12-inch on center deck framing, and 200 amp electrical service. Private Setting & Exceptional Outdoor Living located on peaceful, wooded, 1.1 acre lot, the home features a large deck for outdoor dining and relaxation, plus a private hot tub for unwinding after a day on the mountain. Ample parking ensures easy access for owners and guests alike. Designed for Mountain Living. Both the upper and lower entryways offer exceptional storage solutions, with the lower foyer offering storage for skis and boards, as well as a custom drying rack for wet boots and gear-keeping everything organized and ready for your next adventure. A striking stone, wood-burning fireplace anchors the main living area, creating a warm and inviting gathering space. Spacious & Fully Appointed. With four bedrooms and five bathrooms across three levels, the layout provides comfort and privacy for groups of all sizes, and the spacious chef's kitchen is perfectly appointed for feeding a hungry crowd. The home comes fully furnished and turnkey, allowing you to step right into the mountain lifestyle without lifting a finger. Strong Rental History. This property has an established rental track record, making it an excellent option for buyers seeking both personal enjoyment and investment potential. Don't miss this rare opportunity to own a luxurious, well maintained mountain retreat in one of Killington's most desirable locations. Ready for immediate enjoyment and income generation, call today to schedule a private showing.

Listed by Bret Williamson of Killington Valley Real Estate

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5073006

• Residential Single Family
• Full Bath 4
• Address 286 Coldbrook Road
• Bedrooms 4
• Bathroom 5

This new construction home is in one of Southern Vermont's top four season destinations. Three homes are being built, with two still available, offering a great opportunity to secure a brand new home! The multi gabled modern farmhouse design blends clean architectural lines and warm natural materials. Ideally located just minutes from Mount Snow, the Hermitage Club, Harriman Reservoir, golf courses, and local amenities, this home suits a luxury second home, a strong investment property, or a comfortable year-round residence. The floor plan features a main level primary bedroom with an en suite bath and walk-in closet, plus what could be a second primary bedroom on the lower level with a full bath and direct walkout access to the covered patio. There are two more spacious bedrooms on the top level, each with its own full bathroom, and a bonus room for an office or extra sleeping space. Highlights include a two-story great room with a wood burning fireplace, a large covered porch, and an oversized attached two car garage. Buyers who commit early could personalize finishes within the builder's allowances or choose upgrades at their expense.

Listed by Melissa Nebelski of Real Broker LLC

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 286 Coldbrook Road Wilmington VT 05363 (#5073006).

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MLS Number 5079104

• Residential Single Family
• Full Bath 1
• Address 1559 Swamp Road
• Bedrooms 4
• Bathroom 1

Discover an extraordinary opportunity to own 284.9 acres of Vermont countryside in the scenic town of Fairfield. This remarkable property offers a beautiful mix of open agricultural fields, mature woodland, and abundant wildlife, providing exceptional privacy and endless possibilities for recreation, farming, or a peaceful rural retreat. At the center of the property sits a historic farmhouse built in 1800, offering approximately 1,984 square feet with 4 bedrooms and 1 bathroom. The home is rich with character and presents a wonderful opportunity to personalize a classic Vermont farmhouse while enjoying the surrounding landscape. The expansive acreage provides excellent potential for agriculture, forestry, hunting, trail systems, and outdoor recreation. Protected through a Vermont Land Trust conservation easement, the land has been preserved to maintain its agricultural productivity, natural resources, and scenic beauty for generations while still allowing continued farming, forestry, recreation, and residential use in accordance with the easement. Despite its peaceful rural setting, the property is within driving distance of Jay Peak Resort and Smugglers' Notch, offering easy access to some of Vermont's best skiing, hiking, and four-season outdoor recreation. Large conserved tracts of land of this size are increasingly rare. Whether you're seeking a working agricultural property, recreational escape, or long-term land investment, this unique Fairfield property offers incredible potential and Vermont country charm.

Listed by Michael Preseau of CENTURY 21 North East

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 1559 Swamp Road Fairfield VT 05455 (#5079104).

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MLS Number 5085625

• Residential Single Family
• Full Bath 2
• Address 14 School Street
• Bathroom 5
• Square Feet 18,780

Positioned in the vibrant heart of Bristol Vermont, this iconic former high school presents an exceptionally rare opportunity to acquire a fully leased, income-producing asset with both commercial use and residential zoning, offering multiple avenues for future value and flexibility. Assets of this scale, history, and versatility especially at an approachable price point are rarely brought to market. Steeped in heritage, the property has served the community since the early 1800s, evolving from its origins as a schoolhouse to Bristol High School and now the well-known Bristol Suites. Today, it is meticulously maintained and fully occupied, delivering immediate and stable income from day one. More than just a building, this is a true community hub. A diverse tenant mix including a chiropractor, skin care boutique, forest conservation office, yoga studio, fitness facility, and more drives consistent daily activity and creates a resilient, multi-industry income stream that supports long-term stability. The upper levels are currently configured as professional office suites and open studio spaces, while the lower level is anchored by a popular local gym, reinforcing visibility and steady use. Beyond its current income-producing profile, the property offers meaningful long-term optionality. With residential zoning in place, a future owner may explore conversion to apartments, a mixed-use redevelopment, or even repositioning the property as a distinctive single-family residence, subject to applicable permits and approvals. Its historic character, generous scale, central village location, and flexible interior layout create a compelling foundation for a one-of-a-kind private home or legacy estate. This is not just an investment, it is a scarce legacy asset with built-in income, community integration, residential potential, and meaningful upside in the Bristol, Vermont real estate market.

Listed by Kate Earley and Flex Realty Group of Flex Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5074283

• Residential Single Family
• Full Bath 1
• Address 775 Goose Pond Road
• Bedrooms 4
• Bathroom 2

First time on the market in 54 years! By far the finest parcels on the pond with 500'+/- of shore line with a beautiful beach! Enjoy the late afternoon sunsets, 180 degree mountain views, an old stone fireplace on the point for campfires, 2 separate parcels of land, the waterfront lot has 340' paved road frontage and there is a separate 3.88 ac+/- parcel across the road with 340' frontage as an investment for further development. Enjoy the water & mountain view from the screen porch at the water's edge or head inside to the 1927 cottage with beautiful wood floors, 19x30 living/dining/family room with fireplace, 4 bedrooms, and 2 baths. Goose Pond is 625 acres+/- , 2.9 miles long and .6 miles wide and is located in the towns of Canaan and Hanover with a boat launch.

Listed by Doreen Wyman of Granite Northland Associates

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 775 Goose Pond Road Canaan NH 03741 (#5074283).

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MLS Number 5091163

• Residential Single Family
• Full Bath 2
• Bedrooms 6
• Bathroom 6
• Square Feet 5,616

Set on approximately 49 acres of picturesque Vermont countryside, this extraordinary property offers exceptional privacy, natural beauty, and the rare advantage of two separate homes-perfectly suited for a primary residence with an entertaining guest house, multi-generational living, or short-term rental opportunity. This one-of-a-kind offering provides space, comfort, and endless four-season recreational potential. The main home is filled with natural light, highlighted by expansive windows that frame the surrounding landscape. Thoughtfully designed for both everyday living and hosting, it features two bedrooms, two and a half baths, and a dedicated office space ideal for remote work. Two inviting living rooms create flexible gathering spaces, while the fully equipped kitchen serves as the heart of the home. Rooftop access offers a unique vantage point to take in sweeping countryside views, and central air ensures year-round comfort. The second home functions beautifully as an entertaining guest house, offering four bedrooms, two and a half baths, an additional kitchen and living room designed for hosting family and friends. A bonus room provides even more versatility for recreation, a game room, gym, or studio. Below the homes, a substantial four-bay garage offers abundant storage for vehicles, outdoor equipment, and seasonal gear. The land itself is a private playground, complete with a pond and expansive acreage to create trails for hiking, snowshoeing, or ATV riding. Enjoy sledding in winter, wildlife watching, and peaceful seclusion in every season. Ideally located near Pico Mountain, Killington Resort, and Okemo Mountain Resort, as well as the charming town of Manchester, the property is approximately three hours to Boston and four and a half hours to New York City. A rare opportunity to own a truly special Vermont retreat offering both lifestyle and investment appeal.

Listed by Hughes Group Team of Casella Real Estate

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 1450 Clarendon Avenue West Rutland VT 05777 (#5091163).

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MLS Number 5091891

• Residential Single Family
• Full Bath 2
• Address 8 Twin Rocks Road
• Bedrooms 5
• Bathroom 5

Extraordinary VT Mountain Property w/ Stunning Barn Minutes to Mt Snow & convenient access to VT's renowned VAST snowmobile Trails System. Mountain Retreat w/amazing Income & Expansion Potential. Tucked away at end of a quiet country road in desirable West Dover, this remarkable 5-bdrm, 5-bath contemporary offers the perfect blend of privacy, recreation & opportunity. This property is ideally positioned for year-round enjoyment & investment potential. Built in 2000 & thoughtfully designed for the gathering of family & friends. The home features generous living spaces throughout. The inviting living room centers around a wood-burning fireplace, creating the perfect setting after a day on the slopes or trails. A spacious family and recreation room in the finished walk out basement offers additional entertaining space. On yet another level is a gathering place complete w/ a propane stove that provides warmth & ambiance during Vermont's winter months & here to be enjoyed. The flexible floor plan includes two main-level bedrooms & three baths, while the second floor offers three additional bedrooms & two baths, providing comfortable accommodations for large groups. With the addition of kitchens, this home could easily be configured into separate living spaces, creating outstanding rental or multi-generational living opportunities. Outside, the setting is equally impressive. Multiple outdoor sitting areas allow you to enjoy the peaceful surroundings, while the standing seam roof, classic clapboard siding, and quality construction reflect enduring Vermont craftsmanship. Adding to the property's uniqueness is the stunning barn perched on the hillside above the home. With outstanding character & views of the surrounding landscape, the barn presents exciting possibilities as a future luxury guest house, studio, workshop, event space, or recreational retreat. Perfect whether seeking a primary residence, four-season getaway, investment property, or a combination of all three.

Listed by Jennifer Baker of Connecticut River Valley Realty

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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MLS Number 5082344

• Residential Single Family
• Full Bath 2
• Bedrooms 3
• Bathroom 3
• Square Feet 2,520

Where Mountain Living Meets Modern Design. Set on 7.3± private acres in the heart of Vermont's premier ski country, this extraordinary retreat offers a rare blend of refined luxury and natural beauty. Thoughtfully renovated and expanded, the home showcases over 2,500 finished square feet of curated living space with sweeping views of Killington and Pico, and seasonal glimpses of Camel's Hump and Mount Mansfield. Designed for both comfort and sophistication, the heart of the home is a stunning chef's kitchen featuring marble countertops, a custom oversized island, handcrafted DeVol tile, Rejuvenation hardware, brass accents, a pot filler, and high-end appliances including an Ilve Majestic induction range, Fisher & Paykel, and JennAir. The open living area is anchored by a striking stone fireplace and walls of glass that invite the outdoors in. The private primary suite addition is a true sanctuary, complete with a spacious walk-in closet, spa-inspired steam shower, and a Japanese copper air-jetted soaking tub perfectly positioned to take in the views. Extensive upgrades include new windows throughout, updated electrical and plumbing systems, foam insulation, new HVAC with four heat pumps, and Mysa smart thermostats for enhanced efficiency and comfort. Outdoor living is just as impressive, with multiple decks on all three levels-including a covered cooking deck-ideal for entertaining or quiet relaxation. A second entrance, detached one-car garage, standby whole house generator, updated landscaping with lighting, fire pit, and thoughtful design throughout complete this exceptional offering. This property offers flexibility as a luxury getaway, investment opportunity (off to a strong start with AirBnB rentals), or year-round residence. Ideally located near some of Vermont's most celebrated destinations including Sugarbush and Killington, it also offers convenient access to the charming towns of Warren and Waitsfield. This home embodies the very best of Vermont living!

Listed by The Hammond Team of KW Vermont

Union Street Media
444 South Union Street
Burlington VT, 05401
Office: 802.865.3332

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Your Questions & Comments I have a question about the property at 764 Upper Sparrow Hawk Road Rochester VT 05767 (#5082344).

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