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Brattleboro Houses for Sale

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1468 Upper Dummerston Rd, Brattleboro, VT05301

 House For Sale:
$760,000
Zestimate®: --
Est. Mortgage: $3,442/mo
Beds:
14
Baths:
8.0
Sqft:
10,605
Lot:
968,774
Days on Zillow:
2
Built:
1918
Property type:
Single Family
Brokerage Name:
Palmiter Realty Group
Property Description:
What an opportunity! This farm has amazing history and character, abuts Hillwinds, and has plenty of space for anything you could imagine. The property consists of a main home which sits on 22+ acres with barn and two guest houses. The property originally

95 Chestnut Hl, Brattleboro, VT05301

 House For Sale:
$449,000
Zestimate®: $417,458
Est. Mortgage: $2,033/mo
Beds:
4
Baths:
3.0
Sqft:
3,000
Lot:
25,700
Days on Zillow:
10
Built:
1901
Property type:
Single Family
Brokerage Name:
Berkley & Veller Gr...
Property Description:
This striking circa 1901 wood and stone sided home was built during an era of craftsmanship with an eye towards elegant living. Comprised of 0.59 acres, the land affords stunning views of Brattleboro, Wantastiquet Mountain and the Connecticut River. The cu

305 S Main St, Brattleboro, VT05301

 House For Sale:
$225,000
Zestimate®: $201,964
Est. Mortgage: $1,019/mo
Beds:
4
Baths:
2.0
Sqft:
2,072
Lot:
9,148
Days on Zillow:
10
Built:
1920
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
Surprise! If you're looking for in-town living with a great yard, this is it! Access is on a dead end street, with 2 car garage and plenty of open yard. Four good sized bedrooms, lovely unpainted staircase, huge living room with windows on three sides, two

22 Moreland Ave, Brattleboro, VT05301

 House For Sale:
$220,000
Zestimate®: $211,694
Est. Mortgage: $996/mo
Beds:
4
Baths:
3.0
Sqft:
2,496
Lot:
8,276
Days on Zillow:
19
Built:
1980
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
Lovely cape maintained with immaculate care. this is a great opportunity to live on one level with bedroom and bath on the first floor with tons of extra space in the basement for family room, crafts or your own office. Bedrooms on the second floor are hug

81 Laurel St, Brattleboro, VT05301

 House For Sale:
$425,000
Zestimate®: $298,656
Est. Mortgage: $1,925/mo
Beds:
4
Baths:
3.0
Sqft:
4,000
Lot:
818,928
Days on Zillow:
38
Built:
1990
Property type:
Single Family
Brokerage Name:
Berkley & Veller Gr...
Property Description:
This handsome post & beam home is sited on over 18 in-town acres with access to Windham Foundation Trails and just a short walk to all that downtown Brattleboro offers. Perched on a hill with a real sense of privacy, the residence provides almost 4000 squa

40 Belmont Ave, Brattleboro, VT05301

 House For Sale:
$249,500
Zestimate®: $203,314
Est. Mortgage: $1,130/mo
Beds:
4
Baths:
2.0
Sqft:
1,975
Lot:
9,583
Days on Zillow:
38
Built:
1905
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
Great location! Walk to all the amenities and leave the car at home! Much loved, this period home has been the pride of the current owner who has raised a family here, created tasteful additional living space, back deck and a wonderful back screened porch.

105 Chestnut Hl, Brattleboro, VT05301

 For Sale by Owner:
$500,000
Zestimate®: $424,999
Est. Mortgage: $2,264/mo
Beds:
5
Baths:
3.0
Sqft:
3,000
Lot:
83,199
Days on Zillow:
38
Built:
1912
Property type:
Single Family
Brokerage Name:
Property Description:
Large home on hilltop overlooking Connecticut River with five-mile views north central oil heat + pellet stove. Wood deck on one side Additional property info: http://www.forsalebyowner.com/listing/5-bed-Single-Family-home-for-sale-by-owner-105-Chestnut-Hi

82 High St, Brattleboro, VT05301

 House For Sale:
$279,900
Zestimate®: $239,926
Est. Mortgage: $1,268/mo
Beds:
4
Baths:
3.0
Sqft:
2,370
Lot:
10,890
Days on Zillow:
60
Built:
1914
Property type:
Single Family
Brokerage Name:
Berkley & Veller Gr...
Property Description:
Why drive when you can leave your car in the 2-car garage and walk from this period, single family house to all that downtown Brattleboro has to offer - restaurants, music, movies, gallery walk and more! This is an ideal opportunity for you to work from ho

301 Maple St, Brattleboro, VT05301

 House For Sale:
$349,000
Price Cut: $16,000(May 6)
Zestimate®: $290,732
Est. Mortgage: $1,580/mo
Beds:
4
Baths:
2.0
Sqft:
3,090
Lot:
39,640
Days on Zillow:
83
Built:
1819
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
MOTIVATED SELLERS! 1819 historical four square with surprising upgrades for modern living! Start with the newer addition with vaulted ceilings and french doors leading to the deck, back yard and in-ground pool. Step back in time for the lovely butler's pan

103 Moreland Ave, Brattleboro, VT05301

 House For Sale:
$139,900
Zestimate®: $151,588
Est. Mortgage: $634/mo
Beds:
4
Baths:
1.0
Sqft:
1,044
Lot:
7,841
Days on Zillow:
136
Built:
1945
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
I am looking for my new owner who can appreciate my good bones, lovely yard and great location. I needs some TLC, but if you look closely, I have a little water feature in the garden, a garden shed, fenced yard, and lots of perennials. Nice sized eat in ki

195 Elliot St, Brattleboro, VT05301

 House For Sale:
$135,000
Zestimate®: $139,140
Est. Mortgage: $611/mo
Beds:
4
Baths:
2.0
Sqft:
1,560
Lot:
5,227
Days on Zillow:
194
Built:
1870
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
Did you say that you need a place with lots of room, work needed no problem, being close to Main Street is desirable? All that and priced below town tax assessment! Many years ago it was a two-family but will need to be brought up to code if rented again.

58 Grove St, Brattleboro, VT05301

 House For Sale:
$229,000
Zestimate®: $207,542
Est. Mortgage: $1,037/mo
Beds:
4
Baths:
2.0
Sqft:
2,264
Lot:
4,791
Days on Zillow:
203
Built:
1925
Property type:
Single Family
Brokerage Name:
Berkley & Veller Gr...
Property Description:
BEAUTIFUL DUTCH COLONIAL HOME This beautiful, well-cared-for Dutch Colonial within a short walk of downtown Brattleboro offers craftsmanship and details not found in many contemporary homes. Hardwood floors, original molding, and French doors highlight the

52 Forest Heights Ext, Stratton, VT05360

 House For Sale:
$380,000
Price Cut: $19,000(Mar 6)
Zestimate®: $327,897
Est. Mortgage: $1,721/mo
Beds:
4
Baths:
4.0
Sqft:
3,200
Lot:
435,600
Days on Zillow:
240
Built:
--
Property type:
Single Family
Brokerage Name:
Palmiter Realty Group
Property Description:
Residential Property, Multi Level,Walkout Lower Level - Stratton, VT Wake up everyday and eat breakfast and dinner with the view of North Face trails of Mount Snow. This home features radiant heat on the main floor and walkout basement which has complete k

F2 Cobble Ridge Rd (piper Ridge), Winhall, VT05340

 House For Sale:
$370,000
Zestimate®: $314,499
Est. Mortgage: $1,676/mo
Beds:
4
Baths:
4.0
Sqft:
2,673
Lot:
--
Days on Zillow:
240
Built:
1988
Property type:
Single Family
Brokerage Name:
Winhall Real Estate...
Property Description:
This unique Piper Ridge condo at Stratton Mt is a standout. As you look out the windows of this end unit you see trees, the mountain and lots of privacy. You can easily walk to the Sport Center and tennis courts or go sledding from the back door! Three of

1131 Daubney Rd, Readsboro, VT05350

 House For Sale:
$239,900
Zestimate®: $205,281
Est. Mortgage: $1,086/mo
Beds:
4
Baths:
1.0
Sqft:
1,280
Lot:
2,831,400
Days on Zillow:
254
Built:
1999
Property type:
Single Family
Brokerage Name:
Palmiter Realty Group
Property Description:
Rare opportunity on top of the mountain! Sited perfectly on 65 well kept acres, this modern hunting lodge, sleeps 16, has water and septic, is at the end of the road, private westerly views with great sunsets. Apple and beech trees are plentiful. Stone wal

8487 Zelka Way Rte # 30, Jamaica, VT05343

 House For Sale:
$375,000
Zestimate®: $318,749
Est. Mortgage: $1,698/mo
Beds:
5
Baths:
2.0
Sqft:
2,304
Lot:
301,000
Days on Zillow:
262
Built:
1976
Property type:
Single Family
Brokerage Name:
Lang McLaughry Sper...
Property Description:
In the heart of ski country! Just 2 miles to the access road at Stratton this property is the perfect ski house! Live upstairs and rent down or use the whole place! 5 bedrooms and 2 baths with a pond, decks and patio for outdoor entertainment. Post and bea

85 Grafton Road On The Grn # 234, Townshend, VT05353

 House For Sale:
$495,000
Zestimate®: $420,749
Est. Mortgage: $2,242/mo
Beds:
5
Baths:
6.0
Sqft:
4,700
Lot:
8,712
Days on Zillow:
263
Built:
1790
Property type:
Single Family
Brokerage Name:
The Entry Only List...
Property Description:
Originally a stagecoach inn, rich in history and restored with many custom features. First floor: Gourmet kitchen w/hand-hewn wainscoting cabinets, commercial range and brick hearth w/wood stove. Pantry and unique bar room. Unusual bathroom. Dining Room bo

304 S Main St, Brattleboro, VT05301

 House For Sale:
$160,000
Price Cut: $11,900(May 8)
Zestimate®: $166,507
Est. Mortgage: $725/mo
Beds:
4
Baths:
2.0
Sqft:
1,405
Lot:
6,098
Days on Zillow:
310
Built:
1880
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
A modern home in great location; close to downtown and nearby walking trails. Offered at a reasonable price with several upgrades included, such as; easy care vinyl siding, tilt-in to clean windows, and a newer oversized one car garage. Enjoy the rear east

18 Highlawn Rd, Brattleboro, VT05301

 House For Sale:
$289,900
Zestimate®: $238,336
Est. Mortgage: $1,313/mo
Beds:
4
Baths:
3.0
Sqft:
2,396
Lot:
12,197
Days on Zillow:
382
Built:
1911
Property type:
Single Family
Brokerage Name:
Brattleboro Area Re...
Property Description:
Amazing 1911 character Bungalow with original beamed ceilings, built ins, pocket doors, and lovely woodwork. Special features are a 23' sun porch street side and more private deck south side. Two free standing propane fireplaces and propane log insert in t

176 Canal St, Brattleboro, VT05301

 Foreclosed
Foreclosure Est.: $133,572
Zestimate®: $175,753
Beds:
4
Baths:
2.0
Sqft:
2,300
Lot:
3,920
Days on Zillow:
655
Built:
1920
Property type:
Single Family
Property Description:
HANDY-MAN's SPECIAL!! Whole lot of character here! This Victorian still has a lot of the charm that once made it great. Custom radiators, fireplace, beautiful woodwork, hardwood floors, custom built-ins and transom windows are marks of the original craftma
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