Windsor VT Homes for Sale

3652 Route 44 Windsor VT 05089

Price$425,000

Est. Mortgage: $/month

MLS Number 4740732

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2
  • Acreage 10.2

Well maintained Dutch Colonial sited on 10.2 beautifully landscaped acres with mountain views. Step inside and enjoy the hardwood floors, exposed wood beams and open concept kitchen/dining room that allows guests to step outside onto the deck that overlooks the open fields below. A large living room with cathedral ceiling and a gas burning stove is the perfect place to gather with friends and family. First floor master bedroom with walk-in closet, full bath, laundry and two bedrooms complete the first floor. Upstairs, two additional rooms, 3/4 bath and a loft will be the perfect spot for your out-of-town guests. The lower walkout level provides a large, dry heated space for storage and a two car garage. Outside, walkout onto the plush green lawn with mature perennial gardens, hand picked stone walls, a small apple orchard, and a private little sitting spot overlooking the babbling brook. The private back yard hides the full length multi-level decks that drop down to the above ground pool and allows plenty of space for entertaining and outdoor grilling. Walk down to the lower back yard and you will find a 24x30 Post and Beam barn with electricity and hay storage above. Just a few steps away from the blueberry and raspberry patch sits a 35 year old sugar shack and small maple orchard. It is here where maple syrup and memories were made by a family who has loved and cared for this home. Less than one mile to Mt. Ascutney, 30 minutes to DHMC, and 20 minutes to GMHA.

Listed by Annette Hartley-White and Jon Merrill of Four Seasons Sotheby's Int'l Realty

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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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165 State Street Windsor VT 05089

Price$410,000

Est. Mortgage: $/month

MLS Number 4760823

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 5
  • Acreage 4.65

They don't build houses like this anymore. This amazing colonial revival house has been updated to like-new condition while maintaining the period charm. High ceilings, wood floors, custom built-ins, chandeliers, this house has it all. The recently remodeled kitchen features custom cabinetry reproduced in the style of existing woodwork in the house. Completely private location just minutes from the town center, and within 30 minutes of Dartmouth College and downtown Woodstock. Fabulous mountain views!

Listed by Kyle Arnold of BHG Masiello Brattleboro

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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26 Depot Windsor VT 05089

MLS Number 4744741

  • Commercial
  • Acreage 0.31

"Once in a lifetime," beautiful historical restaurant property "Windsor Station" for sale! Housed in classical Train Station at an active Amtrak stop in the beautiful town of Windsor VT! Ambiance of a Victorian era Depot and decorated with period railroad paraphernalia, this restaurant has a seating capacity for 84. Popular local area restaurant and bar just a short drive from Interstate 91 exits 8 or 9. Popular restaurant that attracts sight and fall foliage seekers, skiers as well as locals from the Upper Valley, Claremont and Woodstock VT areas! Unparalleled reputation for great food, craft beers and entertainment! Owners currently operate dinner only but potential for increased revenue if opened for lunch and breakfast! So much more potential with expansion to covered portion of the Depot structure or outdoor seating!

Listed by Roz Caplan of Century 21 Highview Realty

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$
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$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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2 Pine Street Windsor VT 05089

Price$349,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4702200

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 4
  • Acreage 0.48

MAJESTIC, LAKEFRONT VICTORIAN. This lovingly renovated in town home is a true Gem! Nicely located....so convenient yet so private. Tucked away on a beautiful site with protected views, overlooking Lake Runnemede and abutting a trail system that provides easy access to downtown or a scenic stroll around the lake! This is a "one of a kind' home, featuring ample rooms for family and guests, a spacious country kitchen, stunning wood floors, high ceilings and fireplaced living rooms with lake views! You will be transported the minute you enter....and you will not want to leave!

Listed by Paula Small of Coldwell Banker LIFESTYLES - Hanover

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%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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418 Moonrise Hill Windsor VT 05089

Price$295,000

Est. Mortgage: $/month

MLS Number 4733786

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 5.8

Rare to find a home with great views AND a flat driveway! Near end of road setting with commanding views over your own fields of Ascutney Mountain. 3 bedroom 3 bath home with enclosed porch. 2 car under. Lots of storage. New roof about 10 yrs ago. New boiler. Owned solar system. There is a Vermont Castings wood stove, and a outdoor wood boiler not currently being used. Potential horse property. Fields and gravel roads. Great location close to Windsor Village and the Hospital. Easily commutable to the Upper Valley. Priced below assessment.

Listed by Dana Waters of Dark Horse Realty

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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108 Main Windsor VT 05089

Price$259,000

Est. Mortgage: $/month

MLS Number 4749008

  • Multifamily Multi-Family
  • Property Type Multi-Family
  • Bathroom 4
  • Acreage 0.11
  • Square Feet 4,096

Own a piece of Vermont history! Thomas Jefferson was entering his second term in office when this lovely, Colonial brick masterpiece was built as an Apothecary by physician, Isaac Green, in 1804. Green's home, built in 1796, still rests on the hill behind the Old Apothecary. Now a 4-unit multi-family building, with 3-1 BR units and 1-2 BR unit, this building is fully rented and includes four parking spaces for your tenants. The small lot requires no lawn care and very little maintenance. Monthly rental income is currently $3,375 with plenty of room for growth! Unit #4 has been used for both residential and commercial use over the years. Currently a one-bedroom apartment, this first floor, Main Street-facing unit is perfect for your business as well. Boasting original interior shutters, wide plank, wood flooring and 12-foot ceilings, this space is ready for instant residential or commercial use.

Listed by Susan Wylie of Vermont Realty Group

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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1801 Hunt Road Windsor VT 05089

Price$249,000

Est. Mortgage: $/month

MLS Number 4736398

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2
  • Acreage 5.01

Lovely setting abutting Cider Hill Gardens on desirable Hunt Road. Comfortable single level living, master suite with attached bath, spacious and sunny kitchen and living room with vaulted ceilings. Attached two car garage, basement, and 5 acres of gently rolling land, easily accessible to the Upper Valley.

Listed by Seth Warren of Seth Warren Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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3 Old Mill Pond Road Windsor VT 05089

MLS Number 4759426

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,581

This condo unit is located in one of the most private and scenic settings in our area. Located in the birthplace of Vermont, a charming, historic town, yet set far away from it all. This condo has new flooring, ample storage, 2 fireplaces, a skylight and pond in your backyard for non-motorized boats. Its spacious rooms are full of natural light and the back deck is overlooking the pond, and it has enough room to gather with a crowd. There are essentially 3 master suites, all with full bathrooms, and another office space on the basement level that has a shower, perfect for after using the pool. This is a special unit with an attached garage on the ground floor level, the only one of all 12 units. With so many added benefits, including the entire full basement with bar and gas fireplace and full laundry room with wash basin, this unit is sure to impress. Close proximity to Dartmouth College, Dartmouth Hitchcock and all Upper Valley Amenities. Windsor is home to a grocery store, drugstore, a bit of shopping, eateries, and a 9-hole golf course, but if you seek more, several options are but 20 minutes away. And, if skiing strikes your fancy, there are endless options all within 45 minutes away, for all levels of enthusiasts. Let this be your home away from home.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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3 Old Mill Pond Windsor VT 05089

MLS Number 4759424

  • Condo
  • Bedrooms 3
  • Bathroom 4
  • Square Feet 2,581

This condo unit is located in one of the most private and scenic settings in our area. Located in the birthplace of Vermont, a charming, historic town, yet set far away from it all. This condo has new flooring, ample storage, 2 fireplaces, a skylight and pond in your backyard for non-motorized boats. Its spacious rooms are full of natural light and the back deck is overlooking the pond, and it has enough room to gather with a crowd. There are essentially 3 master suites, all with full bathrooms, and another office space on the basement level that has a shower, perfect for after using the pool. This is a special unit with an attached garage on the ground floor level, the only one of all 12 units. With so many added benefits, including the entire full basement with bar and gas fireplace and full laundry room with wash basin, this unit is sure to impress. Close proximity to Dartmouth College, Dartmouth Hitchcock and all Upper Valley Amenities. Windsor is home to a grocery store, drugstore, a bit of shopping, eateries, and a 9-hole golf course, but if you seek more, several options are but 20 minutes away. And, if skiing strikes your fancy, there are endless options all within 45 minutes away, for all levels of enthusiasts. Let this be your home away from home.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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1A Clough Avenue Windsor VT 05089

Price$249,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4761050

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 4
  • Acreage 0.8

Offered for the first time in 20 years, this is the home everyone will want to take a tour of. It's tucked up on the hill overlooking the town, hidden by gorgeous maple trees, but it opens up to reveal a picturesque setting to come home to. Walking into the kitchen, you will suddenly feel an urge to entertain, utilizing your formal dining room with room for the whole family. Travel on to the cozy living room with fireplace then into the library area that opens onto a beautiful porch you will be sure to have your morning coffee on, rain or shine. With 6 bedroom options, including 2 on the 3rd level, with a renovated 3/4 bathroom, everyone can enjoy their own space. The second level is home to 4 bedrooms, a full bath with claw foot soaking tub, and a 1/2 bath in the master. It also has 2 sleeping porches for warm summer nights. Owners are continuously working on upgrades.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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 Main Street Windsor VT 05089

Price$199,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4733147

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 3
  • Acreage 0.26

This stunning Gothic Revival home in the heart of downtown Windsor is seeking new owners to enjoy it just as much as these owners have. It's been lovingly cared for, with new heating systems, extensive plumbing and electrical work, replacement windows and roof updates as well. 35 Main Street welcomes you with a charm and elegance of the period; tin ceilings, built ins, and exquisite exterior architecture, but will leave you feeling comfortable knowing that it does not need complete updating. Explore the facets of this home, enjoy the beautiful kitchen, take in the landscaping this Spring, and relish in the fact that you can walk to the park, the downtown, and are still only minutes to I-91.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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87 Kennedy Windsor VT 05089

Price$174,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4712652

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2
  • Acreage 1.5

Cute Cape in pleasant neighborhood. Oversized lot is flat, open, and fenced for pets. End of road privacy. Overlooking fields to the CT River. Paved roads to Route 5 with easy access to the interstate at exits 8 or 9 on 91. Convenient to Upper Valley. Low maintenance with roof done 12 years ago. Vinyl siding. 1 bedroom down, 2 up. Attached 1 car garage. Woodstove. Fresh interior paint. Large storage area. Basement could be finished or used as a workshop.

Listed by Dana Waters of Dark Horse Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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6-8 Elm Street Windsor VT 05089

Price$169,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4745144

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 6
  • Bathroom 2
  • Acreage 0.21

What a great way to get your feet wet with home owning. Haven't your parents been telling you to look for a duplex? Well, here it is! The owners unit is freshly painted, carpeted, has newer heating system and central air, has replacement windows, and a beautiful kitchen with double sink. The rental unit is ready for some TLC and elbow grease, but will be ready in no time for your first tenant. Make money, pay your mortgage and start your investment portfolio in a great neighborhood, just steps to the walk-able community of Windsor.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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1200 Juniper Hill Windsor VT 05089

Price$165,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4469339

  • Land
  • Property Type Land
  • Acreage 112.1

Great opportunity for home site with privacy, long range views with clearing, southern exposure, convenient location with easy acces to I-91; interior woods roads; town sewer line at Juniper Hill Road; for the more ambitious, this parcel offers opportunity for potential subdivision; Great New Price! Property taxes are estimated.

Listed by Tom Campbell of Country Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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101 Main Windsor VT 05089

MLS Number 4510101

  • Commercial
  • Acreage 0.2

Diverse commercial space ready to have new owners move in and add to the long list of successful businesses that have graced these buildings. From Blacksmithing to a Point Shop and on to Plumbing, Guns, Woodworking, and so much more. If you've been thinking about having a great store front, and plenty of storage, now is the time to JUMP. Come join Windsor's growing economy, all while being 4 miles to I-91. Owner will consider seller financing.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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82 Main Street Windsor VT 05089
Pending

MLS Number 4693645

  • Commercial
  • Acreage 0.07

Highly visible, extensively renovated retail / office building in the heart of downtown Windsor. Oil baseboard and heat pump heating and cooling, new in 2010. Wiring, shingle roof, flooring, baths, paint, foam attic insulation among recent improvements. 3/4 ba and kitchenette up, 1/2 ba down. Owner occupies office space, retail space leased.

Listed by Seth Warren of Seth Warren Real Estate

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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23 US Route 5 Windsor VT 05089

MLS Number 4715921

  • Commercial
  • Acreage 1.07

Don't miss this HUGE Price drop: Main Street Location, high visibility and tons of parking for your new business. This well maintained two story building has 2760 sq.ft. of space on each floor for a total of 5520 sq.ft. plus a separate 960 sq. ft. storage building. There is excellent office space, and 3 - 14ft. garage bay openings. This property was previously known as Fergusons Automotive. Is this your new business venture?

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

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$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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369 Juniper Hill Road Windsor VT 05089

Price$149,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4744324

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 2
  • Acreage 2.9

3 bedroom Cape, 2 car garage, and a barn sited on just shy of 3 beautiful acres abutting the Windsor Town Forest. Well preserved period detail: wood floors, soapstone sink in kitchen, living room w/ fireplace, numerous built-ins, and the exterior features a standing seam roof and recent paint job. Town water and sewer. The lot includes a large level yard, mature apple trees of numerous varieties, rhubarb,asparagus, and perennials.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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437 Brook Road Windsor VT 05089

Price$149,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4760720

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 3
  • Bathroom 1
  • Acreage 0.8

This unassumming country cape has way more than meets the eye. This property features lots of wonderful and inviting space and is situated on a nice level lot with plenty of yard space for the kids and animals to play. Several garage bays for the cars and toys and two extra quality built sheds for an ample amount of storage or workshop space. Inside the home features many quality built cabinets in the kitchen and beautiful custom woodworking in the dining area, living room and stairway . Updates also include newer laminate floors in the kitchen and dining space as well as updated plush carpet in the living room. Just a Great place to call home as the current owners have for 60 years.

Listed by Alex DeFelice of The Clerkin Agency, P.C.

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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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22 Day Street Windsor VT 05089

Price$148,500

Est. Mortgage: $/month

MLS Number 4762826

  • Residential Single Family
  • Property Type Single Family
  • Bedrooms 2
  • Bathroom 2
  • Acreage 0.44

This 2 BR/2BA Cape style well-maintained home with a wonderful cottage feeling is ready for new homeowners. Flower gardens surround the house as well as the many plantings within the fenced in yard. Living room with fireplace. Enclosed back porch off of the living room. Separate dining room. Well-appointed kitchen includes a separate breakfast nook with built in cabinet and plenty of cabinets and counter space. Double kitchen sink with cabinets. Bedroom and full bath on the first floor. Second floor master bedroom suite includes full bath, walk-in close, sitting area and skylight. Beautiful wood floors throughout the house.

Listed by Amy Messina of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.75% last updated on Jul 11, 2019
* 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 2019 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 July 16, 2019.