245 Southshire Drive, Bennington, VT, 05201 | $499,900

Nestled in one of Bennington’s most sought-after neighborhoods, this elegant 4-bedroom, 2. 5-bath center-hall Colonial offers space, privacy, and timeless charm—all just minutes from downtown Bennington, SVMC Hospital, walking paths, and the Bennington Area Trail System (BATS). The first floor welcomes you with gleaming hardwood floors, a spacious kitchen, a formal dining room, and a gracious living room featuring a wood-burning fireplace and French doors that open to a private deck overlooking the park-like backyard. A separate study offers space for work or reading, while a dedicated laundry room, half bath, and entry to the attached two-car garage add convenience. Upstairs, you’ll find four generously sized bedrooms, including a serene primary suite with a walk-in closet, an additional shoe closet, and a private en suite bath. A full hall bath serves the remaining bedrooms. The fully insulated basement provides excellent storage and features a new electric hot water tank with temperature controls. Outside, mature trees, lilacs, hydrangeas, berry bushes, herbs, and chestnut trees create a lush, beautifully landscaped setting. Move-in ready and meticulously maintained, this turn-key home offers classic comfort in a truly idyllic location. --

Features

  • Rooms: 9
  • Bedrooms: 4
  • Baths: 2 full / 1 half
  • Style: Colonial
  • Year Built: 1984
  • Garage: 2-car Garage
  • Heating: Oil,Hot Water
  • Cooling: Other
  • Basement: Concrete Floor,Interior Access
  • Approx Sq. Feet: 2,116
  • Acreage: 2.93
  • Est. Taxes: $9,113
  • Lot Desc: Landscaped,Level,Mountain View,Neighbor Business,Subdivision,Walking Trails,Near Hospital
  • Elem. School: Monument Elementary School
  • Middle School: Mt. Anthony Union Middle Sch
  • High School: Mt. Anthony Sr. UHSD 14
  • School District: Southwest Vermont
  • MLS#: 5045672
  • Website: https://www.raveis.com
    /prop/5045672/245southshiredrive_bennington_vt?source=qrflyer
©2025 New England Real Estate Network, Inc. All rights reserved.This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of PrimMLS. 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 12/9/2025
Listing courtesy of Alton + Westall Real Estate Agency, LLC   Phone: 413-458-8366
Listing Agent: Ann Greenwood

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Brian SkellyVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 793093

203.415.2989

Brian.Skelly@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
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Joel FanjoyRegional SVP Insurance Sales, William Raveis Insurance

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Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
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245 Southshire Drive, Bennington, VT, 05201

$499,900

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Brian Skelly

VP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 203.415.2989

Brian.Skelly@raveis.com

NMLS Mortgage Loan Originator ID 793093

5/6 (30 Yr)
Adjustable Rate Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $399,920 $399,920 $399,920
Term 360 months 360 months 180 months
Initial Interest Rate** 5.750% 6.375% 5.375%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.533% 6.533% 5.668%
Monthly Tax Payment $759 $759 $759
H/O Insurance Payment $75 $75 $75
Initial Principal & Interest Pmt $2,334 $2,495 $3,241
Total Monthly Payment $3,168 $3,329 $4,075

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.