Glory-goodness! Take a fresh look at 20 Chestnut Street in Rockland proper. This property packs a whole-lotta-punch for forward thinking investors and enterprising owner-occupied homeowners. This surveyed . 45-acre, in-town location offers the opportunity to parcel off . 21-acres as a desirable building lot. The property has three private driveways in place separately accommodating the main house, the in-law apartment, and the empty lot. You could live on site while you build a newly constructed home on the empty lot. Once the new build is completed, enjoy rental income with the two available living units. The main house has four bedrooms, 2-full bathrooms with a newly updated kitchen and downstairs bathroom with laundry. The in-law apartment is studio style one-bedroom apartment with full bathroom, private entry, loft style bedroom, and a sitting deck. Enjoy the proximity to Rockland's vibrant harbor, golf course, museums, theater, shops, coffee spots, and restaurants. Everyday conveniences are within reach, including nearby medical facilities, fitness centers, hiking trails, and recreational lakes.
Situated on a quiet street, 20 Chestnut is a handsome New England-style residence with two living units on . 23-acres. Consider upsizing this investment to include an additional, surveyed, adjacent . 21-acre building lot for an additional $100,000. This property is ideal for owners seeking extra income, or those wanting additional space for family and friends. The flexible configuration appeals to investors, thanks to a blend of large and small living areas and generous parking accommodations. The primary side of the property includes three bedrooms and two full bathrooms. Inside, you will find gracious, wide trim around interior windows and doorways, lending a classic New England charm. Recent renovations have modernized the space, with a new propane furnace installed, an updated kitchen featuring brand-new appliances, and a completely renovated full bathroom on the first floor and laundry closet. Upstairs, the second story houses three spacious bedrooms and another full bathroom, offering comfortable and functional living quarters. The property also includes a charming one-bedroom apartment. This unit features a full bathroom, private entry, a sitting deck, and its own driveway, making it perfect for guests or as a rental opportunity. All will enjoy the property's proximity to Rockland's vibrant harbor, golf course, museums, theater, shops, coffee spots, and restaurants. Everyday conveniences are within reach, including nearby medical facilities, fitness centers, hiking trails, and recreational lakes.
MREIS #1652387
Oct 2, 2026
Price Changed
$340,000
$125/sq ft
Aug 19, 2026
Price Changed
$365,000
$134/sq ft
Aug 6, 2026
Price Changed
$399,000
$146/sq ft
May 24, 2026
Price Changed
$445,000
$163/sq ft
Feb 21, 2026
Listed
$489,000
$179/sq ft
+52
Handsomely situated on a quiet tree lined street surprisingly close to Rockland's downtown, 20 Chestnut is a resilient two-family New Englander offering both grand and compact living spaces. The . 23-acres has driveways on both units with the option of including the surveyed, adjacent . 21-acre building lot for an additional $100,000. If you are seeking a multigenerational home or keen to collect additional income by renting the other side of the house - book a showing to truly see yourself here. Gracious wide trim adorns interior windows and doorways. Recent updates to the main house include a new propane furnace, updated kitchen with all new appliances and new full downstairs bathroom. The second story offers three large bedrooms and a full bathroom. The attached one bedroom with one full bathroom in-law apartment has a private entry, sitting deck and separate driveway. Find yourself thriving in this neighborhood and taking advantage of Rockland's nearby harbor, golf course, museums, theatre, shops, coffee destinations, and restaurants. With nearby medical facilities, fitness centers, hiking trails, and recreational lakes you will certainly enrich your life as resident on Chestnut Street, Rockland and Midcoast Maine.
Year
Property tax
Land + Additions
Assessment*
2025
$6,108 (+17.0%)
$100,700 + $267,700
$368,400
2024
$5,219 (+0.9%)
$53,100 + $160,100
$213,200
2023
$5,174
$53,100 + $160,100
$213,200
2022
$5,174 (+7.4%)
$53,100 + $160,100
$213,200
2021
$4,818 (+1.1%)
$53,100 + $160,100
$213,200
2020
$4,766 (−12.0%)
$53,100 + $160,600
$213,700
2019
$5,417 (+7.3%)
$33,800 + $185,000
$218,800
2018
$5,050 (+3.6%)
$33,800 + $185,000
$218,800
2017
$4,875 (+2.6%)
$33,800 + $185,000
$218,800
2016
$4,752 (+2.4%)
$33,800 + $185,000
$218,800
2015
$4,639 (+5.2%)
$33,800 + $185,000
$218,800
2014
$4,411
$33,800 + $185,000
$218,800
Public record
Beds
3
Baths
1.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.45 Acres
Year renovated
—
Finished Sq. Ft.
2,728
Unfinished Sq. Ft.
—
Total Sq. Ft.
2,728
Year built
1880
Style
Multi-Family (2-4 Unit)
County
Knox County
APN
281685
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 27, 2026.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
4/10 Heat Factor
7 days above 85° expected this year, 17 days in 30 years
6/10 Wind Factor
73% chance of strong winds in next 30 years
1/10 Air Factor
0 unhealthy days expected this year, 0 days in 30 years
Provided by First Street
Historical weather
Rockland, ME • 04841
Average low and high temperatures (°F)
29
15
32
15
42
27
50
37
61
47
72
55
78
61
75
57
69
53
59
44
48
34
35
20
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
92/ 100
Exceptional sunlight
Sunscore
This home receives average direct sun exposure in Rockland. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.1 hrs
5.5 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 20 Chestnut St
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $375,000 and $500,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $375K to $500K.