13

Jamaica, VT Homes for Sale under $500,000

Section Image Section Image
  • /38

    $495,000

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,115 Sq Ft

    367 Stratton Gate Rd, Jamaica, VT 05343

    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

    Agent Photo

    Alison Cummings

    Cummings & Co

    367 Stratton Gate Rd, Jamaica, VT 05343
  • /19

    $425,000

    Open House 10/10
    • 2 Beds
    • 2.5 Baths
    • 1,257 Sq Ft

    190 Depot St, Jamaica, VT 05343

    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

    Carrie Mathews Winhall Real Estate

    190 Depot St, Jamaica, VT 05343
  • /51

    $420,000

    $105K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,888 Sq Ft

    57 Oak Ln, Jamaica, VT 05343

    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

    Mike England Michael England Real Estate

    57 Oak Ln, Jamaica, VT 05343
  • /3

    $250,000

    • Land
    • 4 Acres
    • $62,500 per Acre

    0 Forrester Rd Unit 5110757, Jamaica, VT 05360

    Lot 4 IS 4 acres! This private setting is less than 3 miles to Stratton Mountain Resort with easy access in the no zoning town of Jamaica. Five Bedroom Existing State Issued Wastewater Permit WW-2-2200 along with survey already in place for this lot. Being subdivided off a larger 200+ acre parcel. Power existing on current right of way and is also access to this wooded lot. Residential and

    Chris Lowe Lowe's Real Estate, LLC

    0 Forrester Rd Unit 5110757, Jamaica, VT 05360
  • /15

    $450,000

    $80K PRICE DROP
    • Land
    • 30 Acres
    • $15,000 per Acre

    00 W Hill Rd S, Jamaica, VT 05343

    Discover 30+ acres of coveted Vermont land, offering breathtaking views, open fields, stonewalls, large pond & established driveway. This unique property features an expansive, man-made pond that’s clean, deep, and perfect for paddling, swimming, or even stocking with fish. Excellent southern exposure for solar energy possibilities ,power line access adjacent to the property, this land offers

    Jacki Murano Southern Vermont Realty Group

    00 W Hill Rd S, Jamaica, VT 05343
  • /4

    $299,000

    • Land
    • 57.76 Acres
    • $5,177 per Acre

    0 Vt Route 100 S Unit 5103450, Jamaica, VT 05343

    Discover the possibilities with this exceptional 57+ acre parcel in the Town of Jamaica, Vermont, where no local zoning provides incredible flexibility for your vision. Ideally located just minutes from Stratton Mountain, Mount Snow, and within easy reach of Bromley, Magic Mountain, Manchester, and Brattleboro, this property offers the perfect balance of privacy, recreation, and convenience.

    Julie Lowe Lowe's Real Estate, LLC

    0 Vt Route 100 S Unit 5103450, Jamaica, VT 05343
  • /49

    $500,000

    • Land
    • 71 Acres
    • $7,042 per Acre

    00 Turkey Mountain Rd, Jamaica, VT 05343

    Escape to your own private 71-acre Vermont retreat, offering exceptional privacy and possibility plus access to nearby ski mountain villages. Tucked at the end of a town-maintained dead-end road and bordered on two sides by over 1,000 acres of conservation land, this property promises unmatched peace and lasting protection. Only 20 minutes to either Mt. Snow or Stratton, with over 3,300 feet of

    Jessica Landers Barrett and Valley Associates Inc.

    00 Turkey Mountain Rd, Jamaica, VT 05343
  • /14

    $210,000

    • Land
    • 35 Acres
    • $6,000 per Acre

    00 Vermont Route 100, Jamaica, VT 05343

    Discover the beauty and tranquility of this picturesque wooded parcel—approximately 35 acres—nestled along the serene Deerfield River and spanning the border of Jamaica and Wardsboro. Perfectly situated within easy reach of Mount Snow, Stratton, and Bromley, the property offers convenient access to year-round recreation while preserving the sense of peace and privacy that only a large forested

    Patrice Schneider Southern Vermont Realty Group

    00 Vermont Route 100, Jamaica, VT 05343
  • /9

    $500,000

    • Land
    • 20.2 Acres
    • $24,752 per Acre

    0 W Hill Rd, Jamaica, VT 05343

    West Hill Road is situated prominently on a mountainside, offering breathtaking views that stretch across the valley to the north, with clearing there will be scenic beauty of the area. This property presents an exceptional opportunity for individuals looking to construct their dream home or a private compound, with an abundance of possibilities limited only by one's imagination. Located just

    Mike England Michael England Real Estate

    0 W Hill Rd, Jamaica, VT 05343
  • /25

    $219,000

    • Land
    • 16.9 Acres
    • $12,959 per Acre

    00 Howe Farm Rd, Jamaica, VT 05343

    Discover the possibilities on this exceptional 16.9-acre Vermont property, where privacy, natural beauty, and year-round recreation come together. With nearly 300 feet of town-maintained road frontage and accessible utilities, this parcel is ready for your vision. Thoughtfully shaped by nature, the land offers three potential building sites, making it ideal for a family compound,

    Patrice Schneider Southern Vermont Realty Group

    00 Howe Farm Rd, Jamaica, VT 05343
  • /28

    $480,000

    • 5 Beds
    • 2 Baths
    • 2,194 Sq Ft

    3327 Route 30, Jamaica, VT 05343

    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

    Carrie Mathews Winhall Real Estate

    3327 Route 30, Jamaica, VT 05343
  • /5

    $375,000

    $90K PRICE DROP
    • Land
    • 5.54 Acres
    • $67,690 per Acre

    Lot #4 Margeaux Ln, Stratton, VT 05155

    Nestled along a peaceful babbling brook, this 5.54-acre parcel offers an idyllic setting for building the home of your dreams. Surrounded by a serene wooded landscape, the property provides both privacy and tranquility, while still being just moments from the Sun Bowl at Stratton. With a septic permit already approved for a 4-bedroom home, this lot is ready for construction, allowing you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    Lot #4 Margeaux Ln, Stratton, VT 05155
  • /6

    $395,000

    $100K PRICE DROP
    • Land
    • 6.93 Acres
    • $56,999 per Acre

    lot#2 Margeaux Ln, Stratton, VT 05155

    This stunning 6.93-acre parcel offers the perfect setting to build the home of your dreams, just moments from the Sun Bowl at Stratton. Nestled in a serene wooded landscape, the property provides both privacy and tranquility while being ideally located for easy access to all that Stratton has to offer. With a septic permit already approved for a 4-bedroom home, this lot is ready for you to begin

    Margaret Mcmahon Four Seasons Sotheby's Int'l Realty

    lot#2 Margeaux Ln, Stratton, VT 05155

Home Price Trends

Median Sale Price
$400,000
Median Single Family Sale Price
$549,000
Median 2 Bedroom Sale Price
$275,000
Average Price Per Sq Ft
$329
Number of Homes for Sale
13
Last 12 months Home Sales
35
Months of Supply
6.50
Median List Price
$532,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
-22%
How to Buy a Home How to Finance a Home How to Sell a Home