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Set on 5.63 beautiful acres in one of Bennington's most desirable locations, this exceptional 1880 historic home has been thoughtfully renovated inside and out, blending timeless character with sophisticated modern amenities. The property includes approximately 3,200 square feet in the main residence, an attached two-car garage with a second kitchen, and a separate 1,000-square-foot one-bedroom guest cottage. The stunning chef's kitchen is truly the centerpiece of the home, featuring high-end appliances, a dramatic quartz waterfall countertop, and a generous 10-foot island designed for both everyday living and entertaining. Just off the kitchen is a gorgeous screened-in porch, creating a wonderful extension of the living space and the perfect place to enjoy the tranquil setting. Throughout the main level, beautiful white oak floors add warmth and elegance. The home retains the charm and character expected of a historic property while offering the comfort and efficiency of today's modern systems. The thoughtful renovation continues throughout the home, with details such as automated shades in the primary bedroom and library and a convenient second-floor laundry closet. A fireplace adds warmth and character, while expansive views bring the beauty of the surrounding landscape indoors. The separate one-bedroom guest cottage provides even more versatility for guests, extended family, a private office, or potential rental use. Outside, the property is equally impressive, with gorgeous front and side patios designed for outdoor dining and entertaining, a screened-in porch, beautiful grounds, and a storage shed. A rare combination of historic architecture, exceptional renovation, modern technology, expansive acreage, and flexible living spaces, this property offers a level of quality and versatility rarely found in the Bennington market.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1880
  • 5.63 Acre Lot
  • 2 Car Garage
  • 89 days on Market

  • Bedrooms
    4
  • Bathrooms
    3 full · 1 half
  • Year Built
    1880
  • Stories
    2.0
  • Architectural Style
    Farmhouse, Colonial, New Englander
  • Construction Materials
    Wood Siding
  • Foundation
    Stone
  • Garage Spaces
    2.0
  • Parking Features
    Driveway, Paved, Heated Garage
  • Living Area
    4120.0
  • Interior Features
    Kitchen Island, Soaking Tub
  • Appliances
    Dryer, Dishwasher, Microwave, Refrigerator, Washer, Gas Range, Wine Cooler, Range Hood, Exhaust Fan
  • Flooring
    Tile, Carpet, Ceramic Tile
  • Exterior Features
    Balcony
  • Patio And Porch
    Patio, Porch
  • Heating
    Baseboard, Hot Water, Radiant, Pellet Stove
  • Basement
    Full, Concrete

  • Acres
    5.63
  • Lot Features
    Wooded, Level, Corner Lot, Landscaped
  • View
    Mountain(s)
  • Utilities
    Cable Available
  • Water
    Well

  • County
    Bennington
  • City
    Bennington
  • Zip Code
    05201
  • High School
    Mt. Anthony Sr. UHSD 14
  • Middle School
    Mt. Anthony Union Middle Sch
  • Elementary School
    Monument Elementary School

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Frequently Asked Questions

How do I schedule a tour of 1944 Monument Ave?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 1944 Monument Ave.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 1944 Monument Ave?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 3 bath, listed for $1,695,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Bennington, and can even get you in to see the property quickly.

How do I get a virtual tour of 1944 Monument Ave?

Yes! A virtual tour is available for 1944 Monument Ave. Click here to view the full walkthrough and explore every room at your own pace. If you would like a guided virtual showing or have questions along the way, we can connect you with our local expert to walk you through it live.

How much is the monthly mortgage payment for 1944 Monument Ave?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 1944 Monument Ave at around $10,556. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 1944 Monument Ave?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Bennington County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 1944 Monument Ave?

In most cases, yes. Whether 1944 Monument Ave is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Bennington's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 1944 Monument Ave?

We can handle that for you. Our preferred local agent specializes in residentials in Bennington and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $1,695,000 with 4,120 sqft of space—that comes out to approximately $411 per square foot.

How long has this property been on the market?

1944 Monument Ave was listed on August 15, 2026, which means it's been on the market for 89 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1880, making it approximately 146 years old.

What is the lot size of this property?

1944 Monument Ave sits on a 5.63-acre lot, which is 245,243 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Monument Elementary School
  • Middle: Mt. Anthony Union Middle Sch
  • High: Mt. Anthony Sr. UHSD 14

Want to see how these schools compare? Check out our Bennington County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 1944 Monument Ave?

The most recent public record shows annual property taxes for 1944 Monument Ave were approximately $10,917. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 1944 Monument Ave still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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This information is deemed reliable, but not guaranteed.

The data relating to real estate displayed on this web site comes in part from the IDX Program of PrimeMLS. 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 November 12, 2026 at 05:33AM