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Chesterfield Homes for Sale

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  • 3 Stage Rd, Williamsburg, MA 01096
    3 Stage Rd, Williamsburg, MA 01096
    3 Stage Rd, Williamsburg, MA 01096
    /40

    $529,000

    Open Sun 11AM - 1PM
    • 3 Beds
    • 1.5 Baths
    • 1,781 Sq Ft

    3 Stage Rd, Williamsburg, MA 01096

    Antique Cape that has maintained its wonderful original features along with sensible enhancements for modern living. The large living room with the central chimney fireplace complex that once served as the kitchen and main heating source is the central feature of the main floor. The formal dining area and the living room and bed room share the central space. The first floor is completed by the

    James Molyneux Molyneux Realty

    3 Stage Rd, Williamsburg, MA 01096
  • off Bryant St, Chesterfield, MA 01012
    off Bryant St, Chesterfield, MA 01012
    off Bryant St, Chesterfield, MA 01012
    /9

    $321,600

    • Land
    • 201 Acres
    • $1,600 per Acre

    off Bryant St, Chesterfield, MA 01012

    The Kingsley Lot is 201.3 acres of forest land with 6,760 feet of frontage along the federally designated Wild and Scenic Westfield River in Chesterfield , MA. There is an island in the river that is a part of this property. The property is subject to a permanent Conservation Restriction held by the Mass Div Conservation and Recreation, formerly DEM, that prohibits development and has harvesting

    Keith Ross LandVest, Inc.

    off Bryant St, Chesterfield, MA 01012
  • 254 Bryant St, Chesterfield, MA 01012
    254 Bryant St, Chesterfield, MA 01012
    254 Bryant St, Chesterfield, MA 01012
    /36

    $685,000

    $10K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 2,368 Sq Ft

    254 Bryant St, Chesterfield, MA 01012

    Escape the ordinary and discover a home designed to adapt to your lifestyle. Nestled on 2.73 private acres this spacious Cape blends comfortable everyday living with endless possibilities. The inviting layout features a first-floor primary suite, granite kitchen, dedicated home office, and generous gathering spaces. Upstairs, four additional bedrooms and a separate bonus area with its own garage

    Aimee Tompkins Park Square Realty

    254 Bryant St, Chesterfield, MA 01012
  • 54 Bray Rd, Pelham, MA 01002
    54 Bray Rd, Pelham, MA 01002
    54 Bray Rd, Pelham, MA 01002
    /36

    $249,500

    • 4 Beds
    • 1 Bath
    • 945 Sq Ft

    54 Bray Rd, Pelham, MA 01002

    Seller to contribute escrow up to $22,000 toward a new septic/tight tank (buyers choice). Loved by the same family for generations, this year-round Lake Damond waterfront property is ready for its next chapter. Offering 125 feet of lake frontage, this 4 bedroom, one bath home is tucked into a wooded setting for privacy while still providing plenty of open, sunny space to enjoy the water. The main

    Shelly Hardy Brick & Mortar Northhampton

    54 Bray Rd, Pelham, MA 01002
  • 82 Willcutt Rd, Chesterfield, MA 01012
    82 Willcutt Rd, Chesterfield, MA 01012
    82 Willcutt Rd, Chesterfield, MA 01012
    /42

    $849,000

    Open Fri 4:30PM - 6PM $49K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,968 Sq Ft

    82 Willcutt Rd, Chesterfield, MA 01012

    Nestled into 3.2 acres of serene woodland, this breathtaking custom contemporary Cape — crafted in 2018 by Sovereign Builders — is nothing short of a dream realized. Soaring ceilings and large windows pour golden light across rich hardwood floors, while dreamy western sunsets paint the sky behind multiple mountain vistas. Every room frames woodland views, and resident hummingbirds set a pace that

    Jeanne Troxell Munson The Murphys REALTORS®, Inc.

    82 Willcutt Rd, Chesterfield, MA 01012
  • 31 North Rd, Chesterfield, MA 01012
    31 North Rd, Chesterfield, MA 01012
    31 North Rd, Chesterfield, MA 01012
    /50

    $1,850,000

    $100K PRICE DROP
    • 5 Beds
    • 2.5 Baths
    • 3,464 Sq Ft

    31 North Rd, Chesterfield, MA 01012

    The equestrian elegance of this 55 acre property starts at the gated driveway. Perched on the hilltop is a fully equipped custom build multi use barn entirely heated by radiant floor heat and includes 8 14x14 stalls w/ autowaterers perfect for the breeder or veterinarian. Includes kitchenette, office, laundry and bathroom. Also included is a heated equipment shed and workshop, a heated drive

    Grace Golden EQUINE HOMES REAL ESTATE, LLC

    31 North Rd, Chesterfield, MA 01012
  • 0 Bray Rd, Chesterfield, MA 01012
    0 Bray Rd, Chesterfield, MA 01012
    0 Bray Rd, Chesterfield, MA 01012
    /8

    $69,900

    $10K PRICE DROP
    • Land
    • 12,196 Sq Ft
    • $249,643 per Acre

    0 Bray Rd, Chesterfield, MA 01012

    Peaceful waterfront getaway on beautiful Damon Pond! Rare opportunity to own a private recreational retreat with approx. 130’ of frontage on this scenic 82-acre pond known for its quiet coves, islands, inlets, and natural beauty. Camp, fish, kayak, canoe, swim, or simply unplug and relax by the water. Dock already in place for easy access. Property was previously used as a seasonal camping

    Melissa Stevens Coldwell Banker Community REALTORS®

    0 Bray Rd, Chesterfield, MA 01012
  • 0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
    /5

    $169,000

    • Land
    • 4 Acres
    • $42,250 per Acre

    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012

    Rare water front lot on Damon Pond. Clearing needed to obtain a year round view of the pond. Lot is perc tested, surveyed with electric service being installed.. Join the association and have access to the recreation and beach area. NO power boating but kayaking, canoeing, fishing is available to all members. 25 minutes to Northampton. Year round recreational living in a quiet private setting.

    James Molyneux Molyneux Realty

    0 Pynchon Rd Unit 73512590, Chesterfield, MA 01012
Massachusetts Hampshire County Chesterfield

Real Estate & Homes for Sale in Chesterfield, Chesterfield

Chesterfield Home Prices vs. Nearby MA, MA Neighborhoods

Chesterfield Goshen Cummington Plainfield
Median Home Price
$529,000
$457,450
$387,000
$460,000
Median Sale Price
$430,000
+6% YoY
$420,000
+38% YoY
$365,000
-12% YoY
$435,000
+9% YoY
Median Single Family Price
$482,000
$415,500
$365,000
$460,000
Total Active Listings
6 listings
3 listings
0 listings
3 listings
Market Conditions
5 Months of Supply
Balanced Market
4 Months of Supply
Balanced Market
0 Months of Supply
Seller's Market
4 Months of Supply
Seller's Market

Frequently Asked Questions Why Live in Chesterfield

Is Chesterfield a good place to live?
Chesterfield is a good place to live. Chesterfield is considered very car-dependent and somewhat bikeable. Chesterfield is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. It has a median age of 51. The average household income is $104,159 which is below the national average. College graduates make up 27.1% of residents. A majority of residents in Chesterfield are home owners, with 10% of residents renting and 90% of residents owning their home. A local real estate agent serving Chesterfield can help you decide if this neighborhood is the right one for you. Learn more on our Chesterfield neighborhood guide.
Is Chesterfield, MA a safe neighborhood?
Chesterfield, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Chesterfield?
The median home price in Chesterfield is $529,000. If you put a 20% down payment of $105,800 and had a 30-year fixed mortgage with an interest rate of 6.69%, your estimated principal and interest payment would be $2,730 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $117K a year to afford the median home price in Chesterfield. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Chesterfield is $104K.
What are the best public schools in Chesterfield?
The best public schools that serve Chesterfield are:
What are the most popular zip codes in Chesterfield, Chesterfield, MA?
The most popular zip codes in Chesterfield, Chesterfield, MA include 01012, 01096, 01002, 01027 and 01098.
What are the most popular neighborhoods near Chesterfield, Chesterfield, MA?
The most popular neighborhoods near Chesterfield, Chesterfield, MA are Ashfield and Florence.
Learn more about living in Chesterfield
How to Buy a Home How to Finance a Home How to Sell a Home

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