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Browse the latest real estate for sale in Jamaica, Vermont. If you have any questions or if you'd like to see any of these properties in person, call 802-760-3100 or contact us online.

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1108 West Hill North Road Jamaica VT 05343

Jamaica, VT1108 West Hill North Road

Price$2,450,000

Est. Mortgage: $/month

MLS Number 4821154

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 8
  • Bathroom 8

BETWEEN HEAVEN AND EARTH A NURTURING HAVEN FROM THE WORLD YET 3 MINUTES TO STRATTON MOUNTAIN ACCESS ROAD: Spectacular panoramic vistas of mountain ranges and country valleys under a sweeping sky from this magnificent ski country estate on 99 private acres. A scenic driveway wends its way past a lighted skating pond with warming hut and heated paddle tennis court to the timeless 8 bedroom, 8 bath main residence on a sublime serene hillside setting. A captivating 3 bedroom, 2 bath guest apartment is secluded above the detached 3-bay garage. Spaciousness, comfort , convenience define the open living areas with access onto expansive viewing porches, patios and winterized sun porch. Designed for ease of entertaining and a restorative retreat for the few or many, the main level master suite and en suite guest bedrooms provide restful privacy. Steps from the house, under the stars, is a glass enclosed gazebo with hot tub. Stone walls with perennial gardens enhance the harmonious natural landscape. A world unto itself and still close to Stratton Resort.

Listed by Diana Stugger and Bob Maisey of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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536 Craven Road Jamaica VT 05343

Jamaica, VT536 Craven Road

Price$765,000

Est. Mortgage: $/month

MLS Number 4756775

  • Land
  • County Windham
  • Property Type Land
  • Acreage 408

Unbelievable opportunity to own one of the last large tracts of land in Vermont. To locals, this is known as the Craven Plot. A 400+ acre plot of land made up of wooded, open, stonewalled, harvestable, country land in Jamaica. Ready to be conserved, developed, hunted, forested, cleared, and/or made into a large estate or hunting property or preserve. You name it - you can do it! Jamaica, Vermont does not have any zoning restrictions - come see for yourself and fall in love with this awesome parcel with river frontage, access to Routes 100 and 30 and close to Brattleboro, Manchester, Stratton Mountain, Mount Snow, etc!

Listed by Paul W. Carrocio and Marek Kovac of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Pratt Bridge Road Jamaica VT 05143

Jamaica, VTPratt Bridge Road

Price$575,000

Est. Mortgage: $/month

MLS Number 4842907

  • Land
  • County Windham
  • Property Type Land
  • Acreage 265.8

This fabulous 265.8 +/- acre property includes a 4 lot subdivision and state approved septic designs for you to implement. See MLS #4831490. The remaining land has multiple pond sites, timber that can be harvested now, brook, sugar lot, views, an extensive trail network and with public and private road frontage. All of which is at the end of a quiet and well maintained dead end road less than 15 minutes from southern Vermont premier Ski Resort, Stratton Mountain. Approximately 235 acres of this amazing parcel is enrolled in the Vermont current use program and there is a management plan on file. There is currently timber to be cut based upon the plan. The potential stumpage value for this cut should be of considerable value and the net income could provide opportunity to develop this wonderful site further, or to just maintain this pristine forest landscape and start your dream home on a private reserve. This site offers so much opportunity!! Come see!

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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585 Pleasant Valley Road Jamaica VT 05343

Jamaica, VT585 Pleasant Valley Road

Price$445,000

Est. Mortgage: $/month

MLS Number 4740976

  • Land
  • County Windham
  • Property Type Land
  • Acreage 108

Rare opportunity to own approximately 108 acres of pristine, raw land with Trout stocked ponds and incredible mountain vista's. Just a short drive to the Sun Bowl and 15 minutes to Mount Snow yet totally private and remote. Rich topography with rolling hills and forested stands this property is the natural canvas for to imagine and execute the vision of your dream home. Experience the unencumbered freedom to snowmobile or ATV throughout your own land. Vermont State Wastewater Permits are in place for a 6 bedroom home and a 5 acre development lot for a 4 bedroom home. Underground power installed and established driveway. Please call for more details.

Listed by Ellen Mallia and Andy Reed of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Bobcat Run Jamaica VT 05155

Jamaica, VTBobcat Run

Price$295,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4839013

  • Land
  • County Windham
  • Property Type Land
  • Acreage 88

Oak Hill is an attractive, undeveloped, 88±-acre parcel of land situated in an elevated position overlooking the southern Green Mountains, three area ski resorts, and the picturesque Rawsonville section of Jamaica, Vermont. Historically, this property served as a well-managed woodlot associated with the nearby Loren Coleman Farm. It also offers a choice southern Vermont parcel with attractive rural residential development potential. The land itself is predominately well-drained upland featuring mature hardwood timber with gentle to moderately sloping topography. A small trout stream known as Mill Brook creates the southeasterly boundary line at the toe of the hill. Access originates from Route 100, approximately one mile north of the Route 30 intersection, at which point Bobcat Run leads west. A short private right-of-way provides access from Bobcat Run to the property and crosses the Londonderry/Jamaica town line, terminating near the height of land. Bobcat run is a well-maintained gravel road with power and utilities available. This region of southern Vermont is extraordinarily picturesque, featuring the rolling Green Mountains, interspersed with fertile valleys and farm fields. Oak Hill sits within 15 minutes each of Stratton Mountain Ski Resort, Bromley Mountain Ski Resort, and Magic Mountain Ski Area. Manchester, Vermont is a 25-minute drive. The property is currently enrolled in Vermont's use tax program (UVA).

Listed by David Speirs of LandVest, Inc-Burlington

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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886 Dalewood Road Jamaica VT 05155

Jamaica, VT886 Dalewood Road

Price$269,000

Est. Mortgage: $/month

Pending

MLS Number 4846393

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3

Located in Jamaica VT, this classic ski chalet sits just 4.5 miles to Stratton's lifts, village, restaurants, and shops! Soak in the sun through the many walls of glass in this chalet. Enjoy a spacious open main floor with cathedral ceilings, a cozy fireplace, and sliders out to the deck for even more room to entertain. Conveniently located near the Village of Jamaica, the Jamaica State Park, Pikes Falls and just minutes to Stratton Mountain!

Listed by Carrie Mathews of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1302 VT Route 100 S Jamaica VT 05343

Jamaica, VT1302 VT Route 100 S

Price$259,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4845251

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 1

ALL BEST AND FINAL OFFERS NEED TO BE SUBMITTED BY 3PM SATURDAY JANUARY 30TH 2021. Cool A-Frame on 8.62 acres of land. This two bedroom, one bath home sits back and above Route 100 in East Jamaica, just minutes to Mount Snow or Stratton! Come play and keep your toys in the detached 20x24 garage. Many updates in 2016 to include hot air furnace, flooring, appliances, basement access, metal roof, concrete basement floor, exterior drainage around the house and the list goes on! Great open concept kitchen, living, dining area with wood burning stove. Don't miss this opportunity!! Being sold furnished! ALL BEST AND FINAL OFFERS NEED TO BE SUBMITTED BY 3PM SATURDAY JANUARY 30TH 2021.

Listed by Julie Lowe and Abigail Lowe of Lowe's Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Pratt Bridge Road Jamaica VT 05143

Jamaica, VTPratt Bridge Road

Price$239,000

Est. Mortgage: $/month

MLS Number 4831490

  • Land
  • County Windham
  • Property Type Land
  • Acreage 12.97

This wonderful 4 lot subdivision is close to Stratton and located on a well maintained road is ideal to build your dream home. Options are to develop all four sites and sell them or keep this as is for recreation and fun on 12.97+/- acres. Great investment opportunity as new homes are fast becoming a demand in the area. Waster water permit and a great driveway are already in place and power is right at the road. Don't pass this fabulous opportunity.

Listed by Daire Gibney of Barrett and Valley Associates, Inc/Chest

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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14 Pleasent valley Road Jamaica VT 05343

Jamaica, VT14 Pleasent valley Road

Price$229,000

Est. Mortgage: $/month

MLS Number 4838566

  • Land
  • County Windham
  • Property Type Land
  • Acreage 36.6

3 minute drive to sun bowl at stratton. terraced woodland, possible pond site septic design for a 4 bedroom home owner is offering an Additional 2% commission bonus to selling agent

Listed by Rick Savage of Tamarack Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1386 VT Route 30 Highway Jamaica VT 05343

Jamaica, VT1386 VT Route 30 Highway

Price$199,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4821502

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 2

Great location just 7 miles to Stratton Access Road,

Listed by Julie Lowe of Lowe's Real Estate, LLC

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 100 N Route Jamaica VT 05155

Jamaica, VT33 100 N Route

Price$155,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4680489

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1

Charming historical farmhouse with barn located within minutes of the mountains! On the first floor you will find a full kitchen with walk-in pantry and soapstone sink next to separate dining and living rooms. A bathroom, master bedroom and full washer/dryer set can also be found on the main level. The second story has 2 bedrooms, one enjoys a spacious sitting room or office space. Upstairs has 2 large closets with plenty of storage space for all of your gear. Potential for Residential or Commercial use - check with Town of Jamaica. Change of Use would require Act 250 Approval. The Winhall River borders the lot and it is located in a Flood Zone.

Listed by Annie Bessette and Peggy O'Neill of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 VT 100 Route Jamaica VT 05155

Jamaica, VT33 VT 100 Route

Price$155,000

Active With Contract

MLS Number 4681009

  • Commercial
  • County Windham
  • Acreage 2.33

Opportunity awaits! Three bedroom farmhouse has an adjacent 24' x 24' sturdy barn at the bustling intersection of Routes 30 and 100. The barn is currently divided into a workspace and storage with loft. The home can be accessed through the a breezeway leading to the barn. The storage space features a large sliding door. Potential for residential or commercial use - check with Town of Jamaica - property is in the Flood zone. Commercial Change of Use will require Act 250 modification. Use your imagination - close to other businesses. Is your imagination at work? View this property today!

Listed by Annie Bessette and Peggy O'Neill of TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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#12 Sugar Lot Lane Jamaica VT 05343

Jamaica, VT#12 Sugar Lot Lane

Price$120,000

Est. Mortgage: $/month

MLS Number 4842493

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Acreage 3.6

Sugar Lot Lane , private road, Sunny 3.6 acre lot at end of road with valley views, stone outdoor fireplace , lot is cleared to the boundaries and stone walls has an EC permit and on site well. The Cottage is a LIKENESS of the one being offered. Cottage is not on site, to be delivered after closing.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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35 Mill Brook Road Jamaica VT 05343

Jamaica, VT35 Mill Brook Road

Price$99,000

Est. Mortgage: $/month

Pending

MLS Number 4844888

  • Land
  • County Windham
  • Property Type Land
  • Acreage 17

Awesome 17+/- acre wooded parcel close to skiing. Long brook frontage and a dramatic, natural swimming hole and waterfall on the site of an old Mill. The clearing of the former house and barn site overlooks the brook. Property on both sides of the brook. The land touches Route 100 just above Old Mill Road. Interesting parcel with a lot of potential!

Listed by Geralyn Donohue of Engel & Volkers Okemo-Woodstock

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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154 Depot Street Jamaica VT 05343

Jamaica, VT154 Depot Street

Price$84,800

Est. Mortgage: $/month

Pending

MLS Number 4845203

  • Multifamily Multi-Family
  • County Windham
  • Property Type Multi-Family
  • Bathroom 3
  • Square Feet 2,480

Located in a good, rural village setting, this Cape Cod style multi family residence features three units. Full, unfinished basement. Property consists of approximately 2,480 square footage of living space with a lot size of approximately 23,087sqft. REO property. Buyer to verify all information/condition of property.

Listed by Tiffany Turner of Real Home Services and Solutions, Inc/VT

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Forrester Road Jamaica VT 05343

Jamaica, VTForrester Road

Price$80,000

Est. Mortgage: $/month

MLS Number 4848016

  • Land
  • County Windham
  • Property Type Land
  • Acreage 10.7

Location just 2.5 miles to the SunBowl at Stratton Mountain. Mostly wooded lot in ski country close to all amenities at Stratton. Opportunity to build that dream home in Vermont.

Listed by Cynthia Mitrani of Mountain Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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VT RT 30 Road Jamaica VT 05343

Jamaica, VTVT RT 30 Road

Price$69,000

Est. Mortgage: $/month

MLS Number 4811083

  • Land
  • County Windham
  • Property Type Land
  • Acreage 20.14

LOCATION for this engineered 20.14 wooded land parcel just 7 minutes to the slopes at Stratton, midway between Brattleboro and Manchester, about 4 miles North of the quaint New England town of Jamaica, VT. Close to the Green Mountain National Forest, Jamaica State Park, theWest and Battenkill Rivers this land is located in the perfect spot for the outdoor enthusiast to enjoy hiking, skiing, kayaking, snowshoeing. Engineered for 4 lots. Lot available 7.4 acres for 27,000.

Listed by Cynthia Mitrani of Mountain Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Sugar Lot Lane Jamaica VT 05343

Jamaica, VTSugar Lot Lane

Price$50,000

Est. Mortgage: $/month

MLS Number 4800312

  • Land
  • County Windham
  • Property Type Land
  • Acreage 5

Wooded south facing lot in a lovely country setting. Near the town of Jamaica. Enjoy the Jamaica State Park close by. Stratton Mt. and Mt. Snow Ski areas just a short drive away. Great for vacation or primary home living. EC permit allows for a 3 bedroom home. Access must be off of Sugar Lot Lane. Property line abutts Turkey Mountain Road.

Listed by Carol Cantwell of William Raveis Winhall

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Mountain Acres Road Jamaica VT 05343-0173

Jamaica, VTMountain Acres Road

Price$49,900

Est. Mortgage: $/month

Pending

MLS Number 4840962

  • Land
  • County Windham
  • Property Type Land
  • Acreage 1.9

This is a beautiful gently upsloping 1.9 acre lot completely surrounded by large stone walls and in an established rural neighborhood in the heart of ski country - a perfect spot for your second home or permanent residence. A 30 minute drive to Stratton and Mount Snow, this property is ideally situated and close to Jamaica State Park as well. This is a perfect opportunity for you to realize your dream of a Vermont getaway - a blank canvas awaiting your vision and creative energy. Come up here and scope it out if you are ready to do something amazing!

Listed by Duncan Honig of Maple Leaf Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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oos-65-13 Partridge Lane Jamaica VT 05343

Jamaica, VToos-65-13 Partridge Lane

Price$39,900

Est. Mortgage: $/month

Pending

MLS Number 4830478

  • Land
  • County Windham
  • Property Type Land
  • Acreage 10.4

Wooded 10 acre lot #17 end of road, past camp. Part of the Gleason Farm Deed of Conservation Easement for Wildlife and Forest Land Protection, granted by Patten Corp.

Listed by Michael England of Michael England Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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PINEAPPLE HILL Lane Jamaica VT 05343

Jamaica, VTPINEAPPLE HILL Lane

Price$38,500

Est. Mortgage: $/month

MLS Number 4829584

  • Land
  • County Windham
  • Property Type Land
  • Acreage 1.05

Level building lot ,previously soil tested for inground system, will need to be upgraded, easy drive to both stratton and mt. Snow.

Listed by John Morrison of Barrett and Valley Associates, Inc

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Vermont Route 30 Jamaica VT 05343

Jamaica, VTVermont Route 30

Price$27,000

Est. Mortgage: $/month

MLS Number 4783159

  • Land
  • County Windham
  • Property Type Land
  • Acreage 7.4

This lot is 7 minutes to the slopes at Stratton Resort and about 4 miles North of the quaint village of Jamaica. Engineered 7.4 acres is part of a 4 parcel subdivision. This land is perfect for the outdoor enthusiast close to Jamaica State Park, hiking, skiing, kayaking, snowshoeing. Engineered for a 4 bedroom house. Entire lot of 20.14 acres available for 69,000.

Listed by Cynthia Mitrani of Mountain Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.97% last updated on Feb 25, 2021
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Copyright 2021 New England Real Estate Network, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate for sale on this web site comes in part from the IDX Program of NEREN. 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 March 1, 2021.