Windsor Vermont Real Estate

Are you thinking of buying a home in Windsor Vermont?  Scroll down to view listings that are currently on the market and contact me if you would like more details on specific properties.  You can also create an account with my site to save your favorite Vermont real estate listings.

1672 Hunt Road Windsor VT 05089

Windsor, VT1672 Hunt Road

Price$905,000

Est. Mortgage: $/month

MLS Number 4791655

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 8
  • Square Feet 5,265

Kimball Brook Farm, C. 1789, has a storied history. It was once the residence of author and music critic Marcia Davenport, and is featured in her 1967 autobiography, “Too Strong for Fantasy”. Residents of Windsor report that Katherine Hepburn, a long-time friend of Ms. Davenport's was a visitor to the farm. This spectacular home embodies rambling country elegance and provides generous amounts of room for entertaining, family gatherings and/or events. Kimball Brook is comprised of 8 bedrooms and 5 baths - a total of 5,300 sq feet. There are both large formal areas and cozy spaces, which along with its 5 working fireplaces, highlight the farm's classic Vermont country character. The systems and structure, including heat, water, roofing, siding, foundation, and security have all been intelligently updated with state-of-the-art systems and materials. The large antique barn is a remarkable entity, providing space for projects, animals, vehicles, or celebrations. The property is nestled in a quiet valley amidst the rolling hills of historic Windsor on 32 ac of mixed open and wooded land, overlooking a pond with views into New Hampshire. It is a very short walk (or snowshoe, or bike ride) to an 900+ acre State Wildlife Management Area that provides the many year-round, outdoor activities enjoyed by all Vermonters. Despite its privacy and tranquility, the farm remains easily accessible to local attractions, including Hanover, NH and Woodstock, VT, both within 20 minutes.

Listed by Seth Warren of Seth Warren Real Estate

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$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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

Windsor, VT165 State Street

Price$410,000

Est. Mortgage: $/month

MLS Number 4760823

  • Residential Single Family
  • Construction Existing
  • Bathroom 5
  • Bedrooms 6
  • Square Feet 4,182

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: 3.15% last updated on May 28, 2020
* 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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2151 Hunt Road Windsor VT 05089

Windsor, VT2151 Hunt Road

Price$396,000

Est. Mortgage: $/month

MLS Number 4765375

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,456

It doesn't get much better than this view! Privately situated on 4.5 level acres with multiple outbuildings and a beautiful pond. This well cared for home has had the same owners for 35 years who have taken meticulous care of the property. Stand out features include a large kitchen, open concept floor plan, spacious master suite, wrap around deck, attached 2 car garage and a full walkout basement. If this wasn't enough you'll also find a 1 bedroom apartment space above the attached garage that could be converted into more living space if desired. This truly is Vermont living at its best.

Listed by Wendie Wright of Coldwell Banker LIFESTYLES - Hanover

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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

Windsor, VT418 Moonrise Hill

Price$279,000

Est. Mortgage: $/month

MLS Number 4791528

  • Residential Single Family
  • Construction Existing
  • Bathroom 3
  • Bedrooms 3
  • Square Feet 2,400

This single family home is a rare find with a commanding view of Mt. Ascutney, but with only a short, flat driveway to plow. The 5.8 acres consists of both fields and woods. 3 large bedrooms and 3 full baths home with an enclosed porch. There is lots of storage and a full basement. A new roof was put on about 10 years ago. New boiler last winter and an owned solar system. There is a Vermont castings wood stove inside and an outdoor boiler ( that is not currently being used). This is a potential horse property with fields and gravel roads. While the property is located at the end of a road, it is less than 2 miles from Windsor Village, school and the hospital. Easy commute to upper valley. Why pay their prices? Priced below assessment.

Listed by Jason Saphire of www.EntryOnly.com

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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285 Jewett Road Windsor VT 05089

Windsor, VT285 Jewett Road

Price$255,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4805805

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,452

Beautiful Cape Cod cottage home located in a great family-friendly neighborhood in the birthplace of Vermont. Situated minutes from Interstate-91 and Artisans Park, this private home boasts an open-concept kitchen/dining room, a Great Room with an 11” vaulted ceiling, a 2-car garage, and a full covered front porch. You will love the 3 large bedrooms, granite counter tops in the kitchen, and the sunny office that overlooks the backyard. The sloped front yard is landscaped with perennials, wildflowers, and garden beds, which creates an oasis from the road. The Great Room showcases a Woodstock Soapstone woodstove, slate hearth with an oak mantle, and provides lots of space for entertaining with access to the outdoors and the back deck. The garage stays warm during the Vermont winters and has direct entry into a full, partially finished basement which is perfect for the kid's rec room as well as storage. If you can tear yourself away from your new home, you can enjoy shopping and playing at Artisans Park which is home to Simon Pearce, the Path of Life Garden, Great River Outfitters, and Harpoon Brewery who hosts a spectacular Regional BBQ Competition and Octoberfest. Schedule your showing now before you miss it.

Listed by Amy Hill of Bean Group / Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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
  • Construction Existing
  • Bathroom 4
  • Bedrooms 3
  • 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: 3.15% last updated on May 28, 2020
* 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
  • New Contruction Existing
  • Complex Old Mill Pond
  • Year Built 1989
  • 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: 3.15% last updated on May 28, 2020
* 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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10 Meadow Lane Windsor VT 05089

Windsor, VT10 Meadow Lane

Price$219,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4806057

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,376

Lovely updated one level living home in wonderful neighborhood of similar homes. Freshly painted rooms, new kitchen counters and flooring. Spacious living room with wood fireplace, hardwood floors throughout. Lovely back yard with patio area and a fenced in dog kennel. Full basement offers tons of storage space or future family room space. Large attached two car garage, paved driveway walk to main street and an easy commute to the Upper Valley.

Listed by Gerry Stark of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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25 Sherwin Avenue Windsor VT 05089

Windsor, VT25 Sherwin Avenue

Price$209,000

Est. Mortgage: $/month

Active With Contract

MLS Number 4802882

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 2,100

Located on the corner lot of a dead end street sits this charming home.Tons of potential with spacious rooms and an apartment above the heated two car garage. Newer windows, standing seam roof, and Thermopride furnace. Natural wood throughout and the three season porch add to the home's charm. With both privacy and ideal proximity to village and recreation amenities, this home is sure to please. Bring your own ideas, and make this home your own.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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9 Dorrance Street Windsor VT 05089

Windsor, VT9 Dorrance Street

Price$199,000

Est. Mortgage: $/month

Pending

MLS Number 4806608

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 2,248

Lovely, well-maintained 4 bedroom, 1.5 bath, home situated on a beautifully landscaped half acre lot. Multiple special features include an eat-in kitchen, gleaming hardwood floors, propane stove in the den, fireplace in the living room and a spacious play room in the basement. You'll love the detached garage that includes a work-shop room in the back. This classic two story home is solidly built, well maintained and in move-in condition, not to mention part of a great neighborhood that is walking distance to Kennedy Pond. BONUS: Seller has a transferable share of a sun common solar array at $76 per month that off sets 100% of electric usage.

Listed by Cheryl Herrmann of RE/MAX Group One Realtors

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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221 US 5 North Route Windsor VT 05089

Windsor, VT221 US 5 North Route

Price$189,900

Est. Mortgage: $/month

Active With Contract

MLS Number 4770133

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,152

This house has all you need to settle in and enjoy everything the area has to offer. With I-91 just seconds away, you have access to the Upper Valley in minutes, yet set off enough to listen to the quiet. This home has hardwood floors throughout, a large foyer, and a fireplace in the living room. The potential for income from an unfinished apartment space above the garage make this home a contender, and a great opportunity.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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10 Clough Avenue Windsor VT 05089

Windsor, VT10 Clough Avenue

Price$189,000

Est. Mortgage: $/month

MLS Number 4799715

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 4
  • Square Feet 1,744

This spacious, low maintenance home in the Village of Windsor offers comfort and convenience. It has an updated kitchen, baths, appliances, hot water heater, oil tank and a new pellet stove and deck. Its' floor plan offers a space for everyone. All this is walking distance to schools and many town amenities. Ready to be shown when the stay home stay safe order allows. Just $189,000 Showings will be starting on 4/20/2020 as the state restrictions now permit it.

Listed by Diana Cushing of Montshire Properties

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$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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55 Main Windsor VT 05089

MLS Number 4782518

  • Commercial
  • Year Built 1999
  • Acreage 0.68

Downtown commercial / retail building on large level lot with plenty of onsite parking. Main building is 30X60, large windows, heated and cooled by heat pump, open span, on slab, 1/2 bath, presently utilized as a bicycle / ski retail / repair shop. An unfinished building behind the main building was formerly a car wash, has two tall drive-through doors, high ceiling, on slab, 18X36.

Listed by Seth Warren of Seth Warren Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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18 Pine Street Windsor VT 05089

Windsor, VT18 Pine Street

Price$189,000

Est. Mortgage: $/month

MLS Number 4808564

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 3
  • Square Feet 1,721

Located high on a rim of Lake Runnemede, this 1800's home sits in a quiet neighborhood in the heart of Historic Windsor. You are just minutes away from walking right into the protected land of Paradise Park, where you can safely adventure miles of trails year-round. Among many reasons to love it here is that it is one of the most active and desirable places to bird watch so you are always in for a treat when you roam Paradise. This home has plenty of originality to offer while also having some spectacular upgrades. Come see and feel the charm of this attractive and inviting home. Grand wrap around porch, high ceilings, built-ins, fireplaces, and living space in the attic. So much to fall in love with.

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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 Clough Avenue Windsor VT 05089

Windsor, VT23 Clough Avenue

Price$189,000

Est. Mortgage: $/month

MLS Number 4807884

  • Residential Single Family
  • Construction Existing
  • Bathroom 1
  • Bedrooms 3
  • Square Feet 1,280

Move in ready! This Three Bedroom sturdy home is located in a quiet neighborhood, close to schools and shopping! Many upgrades including New Kitchen, New Bathroom, NEW FURNACE!! and New Oil tank. This charming home has Hardwood floors, tile floor in bathroom and new Laminate Kitchen floors. There is a big deck off the eat-in Kitchen to enjoy some peace and quiet in the big Fenced in backyard. Lake Runnemede close by. Many built-ins and Closets for storage. This property offers a Garage with extra room for storage and a paved driveway.

Listed by Tricia Husain of Bassette Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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51 State Windsor VT 05089

Windsor, VT51 State Street

Price$169,900

Est. Mortgage: $/month

MLS Number 4785589

  • Multifamily Multi-Family
  • Square Feet 3,097
  • Units 3
  • Acreage 0.63

Great location - ideal for owner occupied w/a 3 br apt on 2nd floor. Harvey replacement windows and buderus boiler. Great upside for additional income for investor.

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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
  • Year Built 1897
  • Acreage 0.2
  • Area Business District

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: 3.15% last updated on May 28, 2020
* 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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11 Maple Street Windsor VT 05089

Windsor, VT11 Maple Street

Price$95,000

Est. Mortgage: $/month

MLS Number 4788840

  • Residential Single Family
  • Construction Existing
  • Bathroom 2
  • Bedrooms 2
  • Square Feet 1,210

Affordable village home with 2 br's, 1.5 baths, applianced, eat-in kitchen and a walk to school and shopping location. Maintenance free vinyl siding and standing seam roof. Owner says sell!!!! Price reduced

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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2045 Route 5 South Windsor VT 05089

MLS Number 4786552

  • Multifamily Multi-Family
  • Square Feet 3,488
  • Units 2
  • Acreage 2.46

Excellent potential for redevelopment, 2.46 acres , major road frontage, public water and sewer at site. Presently assessed as a 2 family, easily room for 2 more unis in the existing bldg. Past uses were a in home business, county stop restaurant, cattlemans' restaurant and the top hat. The lower rear section of the property could be used for huge garden space. Building needs total rehab but the future uses make the potential unlimited. Town assessment is $187,260. Now available for $75,000, opportunity is awaiting. Owner may consider short term financing

Listed by Don Chabot of Town and Country Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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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132 Strawberry Windsor VT 05089

Windsor, VT132 Strawberry Hill

Price$40,000

Est. Mortgage: $/month

MLS Number 4808562

  • Land
  • Acreage 1.07
  • Zoning Residential

On the corner of a private little neighbor, this lot is in a great spot. Set off County Road, this lot is ready for your visions to come to life. Minutes from I91 yet set just outside of town. Great hiking/walking trails are within walking distance. This could be the beginning of a very adventurous and exciting time for the new owners!

Listed by Katie Ladue Gilbert of RE/MAX Upper Valley

$
$
%
$/month over payments
Federal 30-year interest rate: 3.15% last updated on May 28, 2020
* 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 2020 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 June 4, 2020.