Jamaica

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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106 and 108 Fawn Ledge Lane Jamaica VT 05343

Jamaica, VT106 and 108 Fawn Ledge Lane

Price$1,199,000

Est. Mortgage: $/month

MLS Number 4860363

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 5
  • Bathroom 5

Here is your opportunity to own 2 homes on one large property! The only 2 houses on the road, tucked away between Mount Snow and Stratton, with expansive views of the Green Mountains! The main house boasts 5 spacious bedrooms (one currently used as an office) and presents an opportunity to personalize the space. This thoughtfully planned home has an open kitchen and dining area with an adjoining sunken style living room, perfect for entertaining large groups and families. Bonus family room in the basement for added space. A cathedral style timber-frame ceiling meets a massive top to bottom fireplace constructed with stones from the property. An impressive sized 4-season sun-room offers the perfect spot to appreciate the views of all seasons from the comfort of your home. Unique details throughout separate this property from traditional homes-wrought iron railings, mid-century hardware, retro lighting etc. The separate guest with 3 BR and 3.5 bathrooms is currently serving as a successful Airbnb. It has a large garage/work shop. Other notable features throughout the property include a separate 5 bay wood/equipment shed, large storage barn, attached greenhouse, garden space, stonework throughout, private pond, multiple wood stoves, and an outdoor furnace. More then enough room for storage/toys-perfect for the 50 acres and conveniently close to snowmobile trails. Dont miss out on all the opportunities this property has to offer!

Listed by Samantha Decker and Jennifer Densmore of Deerfield Valley Real Estate

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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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 TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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3849 VT Route 30 Jamaica VT 05343

Jamaica, VT3849 VT Route 30

Price$625,000

Est. Mortgage: $/month

MLS Number 4863554

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 7
  • Bathroom 8

Once a popular restaurant frequented by tourists and locals alike, the Jamaica House has been updated and has become an expansive residence. Used for a Bed and Breakfast in the early 2000's, this fully furnished 7 bedroom house has a tremendous number of possibilities. The current owners have made many capitol improvements in the past 10 plus years including renovating bathrooms, replacing the commercial kitchen, new flooring, a ADA compliant en-suite bedroom, new windows, the list goes on! The third floor was owners quarters in recent past and in the long ago past it was a ballroom! Easily converted back to an apartment or more living space. Close proximity to Stratton, Bromley, Magic and Mount Snow makes this a super location for a vacation home, income and rental property or business. Truly a gem in excellent condition. Lots going on in Jamaica right now, be a part of it by coming to see this great home!

Listed by Alison Clayton-Cummings of Cummings & Co

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%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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: 2.8% last updated on Jul 29, 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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4941 West Hill Road South Jamaica VT 05343
Active With Contract

MLS Number 4870015

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

Quintessential Vermont farmhouse on 40 beautiful acres! A short 10 minute drive to the Stratton Mtn access road. Enchanting 3 bedroom, 2.5 bath home sits perched on top of a picturesque hill overlooking a delightful meadow with a view of Ball Mtn. While the house has been updated its original 1850's characteristics have been preserved. Hard and soft wood floors throughout, large bedrooms, bright kitchen and baths, large and inviting living room with a cozy fireplace, sweet den with fireplace, heated mudroom, attached two car garage, beyond ample outdoor space with a large barn accessible down a mowed path are a few examples of what make this property so enticing. There is nothing on the market quite like it! Make an appointment to see this extraordinary property to fully appreciate all it has to offer.

Listed by Lauren Behm of Mountain Realty

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$
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$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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591 Edie Lane Jamaica VT 05343

Jamaica, VT591 Edie Lane

Price$375,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4867078

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2

If you're searching for a home in beautiful southern Vermont, come take a peek at this one. Located just 4 miles from the Stratton Resort Access road and a mile to the quaint town of Jamaica Village, you'll instantly feel the warmth and relaxing VT vibe! Built in 1988 by noted local builder, D&L Builders, the floor plan works - open kitchen, dining and living room with fireplace and cathedral ceiling, main floor master with en-suite bath and walk in closet.Upstairs bonus loft, 2 bedrooms and full bathroom. All systems have been updated - roof, boiler, hot water heater. You'll spend less time maintaining and more time enjoying! The setting is lovely, grounds are level with a fire pit with clever seats made out of timber harvested from the property. The large deck is perfect for laying out in the sun with a great book and later grilling and enjoying dinner alfresco with friends. The full basement is dry and can store all your VT toys - paddle boards, canoes, bikes, skis, snowshoes. Live your best life at "591" in the "802."

Listed by Robin Apps and Margaret McMahon of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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8026 VT Route 30 Jamaica VT 05343

Jamaica, VT8026 VT Route 30

Price$369,000

Est. Mortgage: $/month

MLS Number 4869944

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 3

A spacious 3 bedroom, 3 bath contemporary home on 5 acres with a pond is waiting for you ! The main floor is complete with a kitchen/dining area, living room, sunroom and gorgeous views of the pond. From here you have direct access to the waterfront large deck. Convenient first floor master suite with private bath. The second floor offers two additional bedrooms and an office. Utility room, storage room and 1 car attached garage are in the basement level. Close to Stratton and Bromley mountains . All measurements are approximate.

Listed by Tatsiana Clark of Four Seasons Sotheby's Int'l Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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3912 VT Route 30 Jamaica VT 05343
Active With Contract

MLS Number 4860659

  • Commercial
  • County Windham
  • Acreage 0.1

Don't miss out on this awesome investment opportunity in the heart of Southern Vermont Ski Country! Built in the 1800's this attractive building has exposed beams wideboard floors and although everything is grandfathered, systems and building have been updated! New electrical and plumbing in much of the building. Located on highly travelled Vermont Rte 30 the US Post Office enjoys this Jamaica Village Main Street location and the lease goes with the sale! There is also a 2 bedroom apartment and a studio currently rented through Airbnb. Fire Safety has been through and up to code.The 4th unit is a 560 sq. ft. space that present owner uses for his Photo Gallery. This space would be a great office or retail space.Within 15 minutes to Stratton, Bromley and Magic Mtns, 25 minutes to Manchester and 25 minutes to Mt. Snow. As is, there is a positive income. Details upon request. Ask for a video tour to be sent to you.

Listed by Elyn Bischof of Mountain Realty

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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164 Doe Run Road Jamaica VT 05343

Jamaica, VT164 Doe Run Road

Price$293,000

Est. Mortgage: $/month

MLS Number 4875212

  • Residential Single Family
  • County Windham
  • Property Type Single Family
  • Bedrooms 4
  • Bathroom 3

Enjoy the quiet wooded setting of this charming 4 bedroom A-Frame, set on over 5 acres. Located less than 8 miles from Stratton Mountain Resort, and 5 miles from Jamaica State park, this property gives you a perfect base for year round Vermont adventures. The home has two gathering spaces, on the first and second level, each with wood fireplaces, allowing families to spread out and enjoy this house in comfort. Another fire pit, just outside, invites you to enjoy the quiet of Jamaica's wooded landscape, with the company of good friends. Owners have kept up with the maintenance of this home with a new furnace in 2014, a new roof in 2016, and a new septic tank in 2019. Come and see how this home is ready for you to put your own fingerprint on this well maintained, and conveniently located property.

Listed by Trent Stephens and Kim Morgan-Wohler of Wohler Realty Group

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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5299 Vermont Route 30 Jamaica VT 05343

Jamaica, VT5299 Vermont Route 30

Price$269,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4852512

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

Cute country cabin nestled off of Route 30 just minutes to Stratton Mountain Resort! The house has 2 bedrooms plus a loft area with 1 full bath. There is also a two car garage with a spacious studio apartment. Live in one and rent out the other or rent out one and come visit when Vermont calls you! Nature awaits you with the Ball Mountain Dam across the street where you can hike and enjoy a picnic while taking in views of Stratton and Bromley. Come check it out!

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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6217 Route 30 Jamaica VT 05343

Jamaica, VT6217 Route 30

Price$229,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4866185

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

This charming home is located 8 miles from the base of Stratton Mountain and under a mile from Ball Mountain Dam. Set back off the road with a sunny yard perfect for outdoor activity and a large deck to relax on. One level living with a spacious en-suite and second bedroom with a private bath. The living room has a charming rock fireplace and vaulted ceiling. The kitchen offers lots of natural light and cozy nook for a table. A bonus room perfect for an office or separate area to read a book. A great primary, vacation home or rental!

Listed by Jessica Citera of Cummings & Co

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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3104 West Hill Road Jamaica VT 05343

Jamaica, VT3104 West Hill Road

Price$211,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4852551

  • Land
  • County Windham
  • Property Type Land
  • Acreage 14

WOW....Come see this gorgeous location with beautiful views. Nice cleared flat access, drive right in to the sound of a small brook and hardwoods surrounding you. This is the place to enjoy however you see fit. Jamaica has no zoning, so the possibilities are great in this location. Easy access from Route 30, only 6 miles to the Stratton Access Road.

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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Diers Street Jamaica VT 05343

Jamaica, VTDiers Street

Price$149,000

Est. Mortgage: $/month

MLS Number 4866707

  • Land
  • County Windham
  • Property Type Land
  • Acreage 32055

32 acres set on a private, end of road location. The site is partially cleared and ready to build the home of your dreams. The lot is just 3 minutes to the Stratton access road. Please call if you would like a tour of this desirable homesite.

Listed by TPW Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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Cole Pond Road Jamaica VT 05343

Jamaica, VTCole Pond Road

Price$95,000

Est. Mortgage: $/month

MLS Number 4866989

  • Land
  • County Windham
  • Property Type Land
  • Acreage 28

Driveway is in, 4 bedroom septic is approved by the state, located a short drive from Stratton Mountain. With clearing this lot can have some beautiful views. Land known as Lot "A" on attached survey, is located on both sides of Cole Pond Road. Larger 19.1 acre parcel is on the left side with new driveway directly across from Timber Landing, this is the building site location with approved Wastewater Permit. Additional 8.9 acre parcel is located on opposite side of Cole Pond Road where dual set of power lines intersect. Nice quiet spot to take in all the nature this area has to offer.

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

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$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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E Birch Lane Jamaica VT 05343

Jamaica, VTE Birch Lane

Price$56,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4869985

  • Land
  • County Windham
  • Property Type Land
  • Acreage 11

This pretty 11 acre wooded site is just minutes from the village of Jamaica VT with the many recreational opportunities nearby and is only 10 minutes to the areas premier Ski Resort, Stratton Mountain. Whether you want to build a home or just have a quiet slice of heaven to camp on this will be the perfect spot for whatever you choose. The lot sits highy over the road and with only a few homes on the lane privacy is key! Come take a look today!

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

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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LOT 4 VT RT 30 Jamaica VT 05343

Jamaica, VTLOT 4 VT RT 30

Price$50,000

Est. Mortgage: $/month

MLS Number 4866393

  • Land
  • County Windham
  • Property Type Land
  • Acreage 12.91

LOCATION just 7 minutes to the slopes at Stratton, midway between Brattleboro and Manchester, and about 4 miles to the quaint Vermont town of Jamaica home of Jamaica State Park. Build your dream home.... primary or vacation retreat. Shared drive to this 4 lot subdivision. Engineered lot for 4 bedroom on 12.91 wooded acres awaiting your vision. This lot is the largest and sits at end of subdivision. Perfect for the outdoor enthusiast close to the National Forest. Enjoy hiking, skiing, snowboarding, snowshoeing, mountain biking, etc. in your own custom built home.

Listed by Cynthia Mitrani of Mountain Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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$32,900

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: 2.8% last updated on Jul 29, 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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LOT 2 VT RT 30 Jamaica VT 05343

Jamaica, VTLOT 2 VT RT 30

Price$27,000

Est. Mortgage: $/month

Pending

MLS Number 4866390

  • Land
  • County Windham
  • Property Type Land
  • Acreage 2.17

LOCATION just 7 minutes to the slopes at Stratton, midway between Brattleboro and Manchester, and about 4 miles to the quaint Vermont town of Jamaica home of Jamaica State Park. Build your dream home.... primary or vacation retreat. Shared drive to this 4 lot subdivision. Engineered for a 4 bedroom this wooded lot of 2.17 acres awaiting your vision. Perfect for the outdoor enthusiast close to National Forest. Enjoy hiking, skiing, snowboarding, snowshoeing, mountain biking, etc. in your own custom built home. Adjoining Lots #3 (1.81 acres) mls# 4866392 and Lot #4 also available for sale (12.91) mls #4866393.

Listed by Cynthia Mitrani of Mountain Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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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LOT 3 VT RT 30 Jamaica VT 05343

Jamaica, VTLOT 3 VT RT 30

Price$27,000

Est. Mortgage: $/month

Pending

MLS Number 4866392

  • Land
  • County Windham
  • Property Type Land
  • Acreage 1.81

LOCATION just 7 minutes to the slopes at Stratton, midway between Brattleboro and Manchester, and about 4 miles to the quaint Vermont town of Jamaica home of Jamaica State Park. Build your dream home.... primary or vacation retreat. Shared drive to this 4 lot subdivision. Wooded engineered lot of 1.81 acres awaiting your vision. Perfect for the outdoor enthusiast close to National Forest. Enjoy hiking, skiing, snowboarding, snowshoeing, mountain biking, etc. in your own custom built home. Adjoining Lots #2 (2.17 acres) mls#4866390 and Lot #4 also available for sale (12.91acres) mls #4866393.

Listed by Cynthia Mitrani of Mountain Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 2.8% last updated on Jul 29, 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 August 2, 2021.