Chesterfield MA FSBO Homes (32)

Sort By

List
Map

We have 32 homes for sale by owner in Chesterfield, MA. The median list price in Chesterfield, MA is $1,599,781 and the average price per square foot is $58.

Vacant Land For Sale

$150,000

39 Acres(Lot)

Skyline Trail, Chesterfield, MA

Embrace the beauty of nature with this incredible opportunity to own several acres of serene, wooded land!... Read More

Homes For Sale

$899,000

3 Bed
2 Bath
2,922 Sqft
71.71 Acres(Lot)

330 East St, Chesterfield, MA

Welcome to your sanctuary of privacy, natural beauty and well-being! this exquisitely designed home, set on 70... Read More

Vacant Land For Sale

$299,800

70 Acres(Lot)

31 Skyline Trail, Chesterfield, MA

This 70-acre parcel in chester & huntington, ma offers a rare opportunity for privacy and natural beauty. there... Read More

Pending

Homes For Sale

$450,000

4 Bed
2 Bath
2,593 Sqft
1.7 Acres(Lot)

419 Main Road, Chesterfield, MA

A quintessential 1870 new england farmhouse, and former parsonage, built with quality and benefitting from many... Read More

Pending

Vacant Land For Sale

$70,000

4.93 Acres(Lot)

Lot A Pynchon, Chesterfield, MA

An outstanding forest sanctuary. five acres with some scenic, level areas to build your new home. this land is... Read More

Vacant Land For Sale

$49,000

6.75 Acres(Lot)

Lot 13 Skyline, Chesterfield, MA

Wonderful level lot with perk test in hand. this flat lot has a survey and has been flagged. a wooded property... Read More

Pending

Vacant Land For Sale

$60,000

4.47 Acres(Lot)

40 East St, Chesterfield, MA

Lovely building lot on east st in chesterfield. partially cleared, with stream access. as a bonus there is a... Read More

Pending

Homes For Sale

$425,000

4 Bed
3 Bath
2,165 Sqft
0.71 Acre(Lot)

424 Route 20, Chesterfield, MA

Step inside this inspiring contemporary home filled w/ warm wood tones, elevated ceilings & artistic angles... Read More

Pending

Homes For Sale

$300,000

3 Bed
1 Bath
1,094 Sqft
1 Acre(Lot)

11 Damon Pond Rd, Chesterfield, MA

In the rolling hills of western new england is a peaceful setting, nestled in nature, offering a sense of... Read More

Homes For Sale

$425,000

4 Bed
3 Bath
2,165 Sqft
0.71 Acre(Lot)

424 Route 20, Chesterfield, MA

Discover the perfect blend of modern upgrades and timeless charm in this captivating chester home! vaulted wood... Read More

Pending

Homes For Sale

$399,900

3 Bed
2 Bath
2,043 Sqft
2.5 Acres(Lot)

11 Bryant St, Chesterfield, MA

Amazing split level home with privacy, land and small town vibes! chesterfield is a picturesque town on the... Read More

Vacant Land For Sale

$850,000

191 Acres(Lot)

Lot 61 Skyline, Chesterfield, MA

Subdivision available. a 191-acre property with open land, forest and potential views. we have a plan dividing... Read More

Vacant Land For Sale

$50,000

3 Acres(Lot)

Lot 3 Skyline, Chesterfield, MA

A great 3-acre parcel on a paved road with stone walls. lightly forested and flat. this is a relatively easy... Read More

Vacant Land For Sale

$89,000

2.06 Acres(Lot)

63 Sugar Hill Road, Chesterfield, MA

A building lot that is ready to go! level, mostly open, with a well and two bedroom septic system already in... Read More

Homes For Sale

$450,000

3 Bed
3 Bath
2,100 Sqft
0.46 Acre(Lot)

11 Farmhouse Road, Chesterfield, MA

The owner built this for their retirement home, but their plans changed. be the first to occupy this bright &... Read More

Pending

Homes For Sale

$255,000

2 Bed
1 Bath
1,156 Sqft
0.49 Acre(Lot)

396 Route 20, Chesterfield, MA

Single story 2 bedroom ranch located in the gateway of the berkshire range. hardwood floors through most of the... Read More

Pending

Homes For Sale

$220,000

2 Bed
1 Bath
1,116 Sqft
6.17 Acres(Lot)

134 Indian Hollow Rd, Chesterfield, MA

Escape to tranquility at this charming 2 br, 1-bath cottage nestled in nature. spanning 6.17 acres of lush... Read More

Pending

Homes For Sale

$110,000

4 Bed
2 Bath
2,394 Sqft
24.8 Acres(Lot)

10 William St, Chesterfield, MA

Come see this charming colonial-style home featuring four bedrooms and two full bathrooms, encompassing nearly... Read More

Pending

Homes For Sale

$242,500

3 Bed
2 Bath
1,411 Sqft
0.9 Acre(Lot)

54 Route 20 Rd, Chesterfield, MA

Located in chester, the gem of the valley, is this quaint home with character and charm. this 19th century home... Read More

Pending

Homes For Sale

$475,000

5 Bed
3 Bath
2,094 Sqft
4.3 Acres(Lot)

166 Bromley Rd, Chesterfield, MA

Seller is still allowing showings and back up offers. welcome to this expansive ranch set on 4.3 acres of serene... Read More

Chesterfield - Statistics and Home Trends

Actives Activity Chart

Homes For Sale By Owner in Chesterfield 19

	Average Price
2 Bed Homes For Sale in Chesterfield (6)	$ 224,817
3 Bed Homes For Sale in Chesterfield (7)	$ 481,471
4 Bed Homes For Sale in Chesterfield (5)	$ 402,000
5+ Bed Homes For Sale in Chesterfield (1)	$ 475,000

AVERAGE PRICE

$ 395,822

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ 218

Land For Sale By Owner in Chesterfield 12

	Average Price
Land For Sale in Chesterfield (12)	$ 346,288

AVERAGE PRICE

$ 346,288

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

$ N/A

Statistics Bottom Ads 1

Learn More About Chesterfield, Massachusetts

Currently there are 19 homes for sale and 12 vacant land for sale in Chesterfield

Currently Chesterfield has 31 properties on the market for sale. The inventory was last updated 04/15/2025. Of these properties, 19 single family homes are for sale by their owners in Chesterfield, and 0 condos are for sale by their owners in Chesterfield. The average price of the single family homes for sale in Chesterfield, is $395,822, the average condo price in Chesterfield, is $346,288. The average price per square foot of the active inventory is $109. This is based the living area square footage.

Over the last year, there have been 8 of properties sold in Chesterfield. Of these properties, 7 single family homes have sold by their owners in Chesterfield, and 0 condos have sold by their owners in Chesterfield. The average sales price of the single family homes sold in Chesterfield, is $372,420. Single family homes have been selling for 219 per square foot of living area. The average sales price of the condos for sale in Chesterfield, is $331,815. Condos have been selling for 107 per square foot of living area.

The most active subdivisions with listings for sale in Chesterfield, are:

If you are thinking of selling your Chesterfield home, try our flat fee listing service, Our list fees start at $449, and may save you $15,000 in real estate commissions. Click here to start saving.

Disclaimer: Listing broker has attempted to offer accurate data, but buyers/lessees are advised to confirm all information IDX information is provided exclusively for consumers' personal, non-commercial use that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by the MLS. The MLS may, at its discretion, require use of other disclaimers as necessary to protect Participants and/or the MLS from liability.
This data up-to-date as of 04/15/2025

Chesterfield MA FSBO Homes (32)

Skyline Trail, Chesterfield, MA

330 East St, Chesterfield, MA

31 Skyline Trail, Chesterfield, MA

419 Main Road, Chesterfield, MA

Lot A Pynchon, Chesterfield, MA

Lot 13 Skyline, Chesterfield, MA

40 East St, Chesterfield, MA

424 Route 20, Chesterfield, MA

11 Damon Pond Rd, Chesterfield, MA

424 Route 20, Chesterfield, MA

11 Bryant St, Chesterfield, MA

Lot 61 Skyline, Chesterfield, MA

Lot 3 Skyline, Chesterfield, MA

63 Sugar Hill Road, Chesterfield, MA

11 Farmhouse Road, Chesterfield, MA

396 Route 20, Chesterfield, MA

134 Indian Hollow Rd, Chesterfield, MA

10 William St, Chesterfield, MA

54 Route 20 Rd, Chesterfield, MA

166 Bromley Rd, Chesterfield, MA

Nearby Cities

Popular Cities

Nearby Counties

Property Types

Chesterfield - Statistics and Home Trends

Actives Activity Chart

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

AVERAGE PRICE

NEW LISTINGS THIS WEEK

PRICE PER SQUARE FOOT

Statistics Bottom Ads 1

Learn More About Chesterfield, Massachusetts

For Sale By Owner California

Statistics Bottom Ads 2

For Sale By Owner Illinois

Statistics Bottom Ads 3

For Sale By Owner Florida

For Sale By Owner Alaska

Statistics Bottom Ads 4

YouTube Video