Jamaica Homes under $500,000

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Newest Jamaica Homes under $500,000

$249,000

3 Beds ⋅ 2 Baths ⋅ 5114286 MLS

Step into a piece of Jamaica Village history. Once home to the F.E. Smith Dry Goods, Ready-Made Clothing, and Grocery Store, this distinctive red-and-white building blends Greek Revival presence with Vermont farmhouse character and now serves as a year-round residence filled with history and personality. The classic façade features full-width double-decker porches, white picket railing, and bold corner pilasters. Inside, this C. 1860 building’s commercial past lives on in a dramatic great room with original built-in storefront shelving and drawer banks once used to display dry goods. Now a unique library, studio and sitting area, the space features wide-plank wood floors, exposed beams, and natural light from the original storefront windows and door. A vintage interior sash window adds another unexpected architectural detail. The kitchen features sage cabinetry, granite tile counters, a pot rack, sunny breakfast area, and walk-in pantry. A cozy living and dining room offers a comfortable gathering space, while upstairs bedrooms retain original wide pine floors and vintage details. Both bathrooms have been updated, and the oil tank, on-demand hot water heater, pressure tank, and well pump have all been recently replaced. Garden beds and a painted harlequin porch floor add personality outside, while the covered porch invite you to enjoy morning coffee and the rhythm of village life. A rare opportunity to own a property with a story to tell and the potential to make it your own. Buyers who appreciate historic homes and are comfortable with a project will find opportunities to build on its existing character.

39 Pikes Falls Rd, Jamaica

$489,000

6 Beds ⋅ 5 Baths ⋅ 5113514 MLS

Village living with room for possibilities! Just steps from Jamaica State Park and downtown Jamaica, this versatile home offers a wonderful opportunity to enjoy Vermont living with the added benefit of separate living spaces and potential rental income. Abutting the river, the property is currently configured as three spacious two-bedroom apartments—two with one bath and a third with two baths. Make one apartment your full-time residence or Vermont getaway while renting the others, or explore options for bringing extended family together while maintaining privacy and independence. Two apartments are currently vacant and ready for immediate occupancy. The third is home to long-term tenants who hope to stay, offering potential ongoing income. Recent improvements include a new furnace, new well pump, freshly painted exterior, and replacement windows where needed. The hot water heaters are approximately five years old. One apartment features a new refrigerator and stove, while another includes a three-year-old washer and dryer along with a new dishwasher. Enjoy a location that puts outdoor adventure and village charm right outside your door. Walk to Jamaica State Park for hiking, biking, swimming, and exploring, or stroll downtown to enjoy this welcoming Vermont community. Stratton Mountain and other Southern Vermont attractions are within easy reach, making this an appealing home base in every season. Whether you envision a primary home with supplemental income, a vacation retreat with space for guests, or a future reconfiguration to suit your needs, this property offers exceptional flexibility. Any conversion or changes in use would be subject to applicable approvals. A special opportunity to make yourself at home in the heart of Jamaica!

154 Depot St, Jamaica

$489,000

5113501 MLS

An exceptional investment opportunity in the heart of Jamaica! Just steps from Jamaica State Park and the charm of downtown Jamaica, this three-unit multifamily property offers an ideal combination of location, flexibility, and income potential. Whether you’re looking to live in one unit while generating income from the others, create a Vermont getaway with rental income, or add a versatile property to your investment portfolio, the possibilities are plentiful. The property abuts the river and features three spacious two-bedroom units: two with one bath and a third with two baths. Two units are currently vacant and ready for immediate occupancy, while the third is occupied by long term tenants—offering the potential for income from day one. Consider long-term rentals, seasonal leases, or short-term rentals such as Airbnb, subject to applicable local and state requirements. Recent improvements make this an especially attractive opportunity. Updates include a new furnace, new well pump, freshly painted exterior, and replacement windows where needed. The hot water heaters are approximately five years old. One apartment features a new refrigerator and stove, while another offers a three-year-old washer and dryer along with a new dishwasher. And then there’s the location! Walk to Jamaica State Park for hiking, biking, swimming, and outdoor recreation, or stroll into the village to enjoy everything this quintessential Vermont community has to offer. With Stratton Mountain and other Southern Vermont attractions within easy reach, the property is well positioned to appeal to year-round, seasonal, and vacation renters alike. Three units, multiple income possibilities, recent improvements, and an outstanding village location make this a rare opportunity to invest in one of Southern Vermont’s most desirable four-season communities.

154 Depot St, Jamaica

$425,000

2 Beds ⋅ 3 Baths ⋅ 5110722 MLS

Tucked into a quiet, sunny setting just steps from Jamaica State Park and the heart of Jamaica Village, this charming two-bedroom plus loft Cape offers the perfect blend of Vermont character, comfort, and convenience. Filled with natural light and warm wood accents, the home has an inviting feel from the moment you step inside. A spacious mudroom provides a practical entry for every season and opens into the kitchen, where a center island and gas cooktop make it easy to gather, cook, and entertain. The open floor plan flows naturally into the main living area, where a cathedral ceiling adds a wonderful sense of space and a wood-burning stove creates a cozy focal point for winter evenings. The home offers two bedrooms plus a versatile loft, ideal for additional sleeping space, a home office, or a quiet retreat. The primary bedroom features its own ensuite bath, and with two full baths and one half bath, there is plenty of room for family and guests. Adding to the property's future potential, the existing septic permit is approved for three bedrooms, offering flexibility should a future owner wish to expand. Outside, enjoy a peaceful setting with space for gardening and relaxing in the Vermont sunshine. An oversized two-car garage provides exceptional room for vehicles, outdoor gear, bikes, skis, kayaks, and all the equipment that comes with four-season living. The location is hard to beat. Walk to Jamaica State Park for hiking, swimming, and access to the West River, or head into Jamaica Village just moments away. When the snow flies, Stratton Mountain is approximately 15 minutes away and Mount Snow about 25 minutes, while the shops, restaurants, and amenities of Manchester are approximately 30 minutes from your door. Whether you're looking for a full-time Vermont home or a comfortable mountain getaway, this sunny Jamaica Cape puts village life, outdoor recreation, and some of Southern Vermont's best destinations within easy reach—all while offering a quiet place

190 Depot St, Jamaica

$63,000

2 Beds ⋅ 1 Baths ⋅ 5097748 MLS

Looking for an easy escape to the mountains? This furnished 2-bedroom mobile home sits right on the banks of the West River in West River Park—an ideal spot for seasonal living in Southern Vermont. The park has 23 sites and allows homeowners to stay up to 6 months each year, making it a great option for summer adventures or a winter ski base or, a little bit of both! Stratton is just 20 minutes away, and Mount Snow about 30, so you're never far from the slopes. In warmer months, enjoy fishing, swimming, or hiking nearby. The home has seen several recent updates, including new windows, a new chimney, oil tank, outdoor storage shed, and a propane stove for that cozy cabin feel. Park rent is $435/month and covers water, septic, snow removal, and lawn care—making for simple, low-maintenance living. If you’ve been looking for a quiet spot with river views and easy access to all the region has to offer, this might be the one.

2022 Rte 30, Jamaica

$439,000

5 Beds ⋅ 2 Baths ⋅ 5097573 MLS

Nestled on 1.25 flat and beautifully maintained acres and just 1/2 mile from the village, this spacious 5-bedroom home offers the perfect blend of charm, convenience, and Vermont lifestyle. The lovely yard features a mature raspberry patch, ample space for gardens, outdoor entertaining, or simply enjoying the peaceful setting. Ideally located just 1/2 mile from the heart of Jamaica Village and only 3/4 mile to Jamaica State Park, outdoor recreation, dining, and local shops are all close by. Stratton Mountain and Mount Snow are both just 20–25 minutes away, making this an excellent four-season retreat or full-time residence. Inside, the home offers hardwood floors throughout, generous living space, and a wonderful sunroom with a woodstove hookup perfect for cozy evenings year-round. Additional highlights include a paved driveway, easy access to Route 30, an attached garage and workshop space.. For added transparency and peace of mind, the seller has completed a pre-listing property inspection, which is attached in the MLS. Lovingly owned by the same family since it was built, this home is filled with warmth, history, and opportunity for its next chapter. This property has full time tenants and need a minimum of 24 hours notice, longer preferred, on showings. Closing can happen October 1 or after.

3327 Rte 30, Jamaica

$140,000

1 Beds ⋅ 1 Baths ⋅ 5097088 MLS

Some places stop time. River's Edge is one of them. Step off the front door and onto a 10×12 covered porch shaded by old hemlocks, facing directly over the West River away from the road, away from everything. The sound of moving water. The smell of the trees after rain. This porch is not an afterthought Brand new Lancaster Log Cabins "Sierra" Park Model. This 100% turn-key real log cabin features a rustic aesthetic with modern durability. Includes a 10' covered front porch, a cozy loft for extra space, and cathedral ceilings with exposed log beams. Situated on a newly poured concrete slab in the beautiful French Bridge Chateau community. Perfect for those seeking a high-end, low-maintenance retreat. Park approval is required. This unit can only be occupied 180 days a year per State Permit. The Sierra arrives fully turn-key: kitchen with full appliances including an over-the-range microwave, full bath, living area, two bedrooms, and a sleeping loft that gives you the flex for extra guests. At 320 sq ft of interior space plus 120 sq ft of covered porch, it lives larger than it measures — the layout wastes nothing. Never used and installed in 2026. Will make a great comfortable vacation getaway in any season. The park also maintains the landscaping.

2074 Vt Rt 30, Jamaica

$495,000

4 Beds ⋅ 3 Baths ⋅ 5097042 MLS

Nestled on 2.4 private acres along desirable Stratton Gate Road, this well-maintained four-bedroom, three-bath home offers the perfect balance of comfort, space, and year-round recreation. Just minutes from Stratton Mountain, you’ll enjoy easy access to skiing, golf, hiking, mountain biking, and all that Southern Vermont has to offer. Designed for gathering and relaxing, the home features two spacious living areas, providing plenty of room for family and guests. A cozy wood stove creates the perfect après-ski atmosphere, while the inviting three-season porch offers a peaceful place to enjoy the natural surroundings from spring through fall. The level, secluded lot provides privacy and outdoor enjoyment, with ample space for entertaining, gardening, or simply unwinding. Conveniently located near Stratton, Bromley, Manchester, and local dining and shopping, this property is equally suited as a full-time residence, vacation retreat, or investment opportunity. Experience the best of Vermont living in a location that puts adventure and relaxation right at your doorstep.

367 Stratton Gate Rd, Jamaica

$420,000

3 Beds ⋅ 2 Baths ⋅ 5081124 MLS

This charming saltbox home, built in 1980, features three bedrooms and two bathrooms, complemented by a dining room that invites abundant sunlight. The spacious living room and family room, equipped with a wood stove, create a warm and inviting atmosphere. The large kitchen offers ample space for culinary endeavors, while the full unfinished basement presents opportunities for customization. Set on 5.65 acres of bright, sunny land, the property includes a greenhouse and is bordered by a picturesque stone wall along a private road. Nestled in the country village of Jamaica, it is surrounded by wooded areas teeming with wildlife, yet conveniently located just 20 minutes from four major ski resorts and close to Jamaica State Park, which offers excellent hiking and camping options. While the home requires some updating, it provides a perfect blend of rural tranquility and accessibility to Vermont's attractions.

57 Oak Ln, Jamaica

$57,000

2 Beds ⋅ 1 Baths ⋅ 5072288 MLS

A cozy base for days spent enjoying Vermont country life warmed by a cozy wood stove and enjoying countless meals prepared together in the upgraded cherry and tile kitchen. Property has direct access to the West River. a nice deck to sit on in the back and a nice sitting platform overlooking river. Two bedroom one bath mobile home. Six months occupancy per year. New tenants must be approved by the park.

2036 Vt Rt 30, Jamaica

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Jamaica Homes under $500,000

Newest Jamaica Homes under $500,000

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