OFF MARKET

Off Market Nov 2022 for $950K

$1,098,418

•

2,240

sq ft

208 Winston Rd, Waldoboro, ME 04572

About this home

Welcome to 208 Winston Rd, Waldoboro. This exceptionally and lovingly renovated and restored 1860 Colonial Farmstead consists of 4-5 bedrooms and 2.5 bathrooms, includes 200 acres spanning Waldoboro and Union, with 10 acres for homestead use, 190 acres in conservation with a forestry plan and harvesting rights, and three 2 acre lots that can be developed further - with the option of siting them on Jackson Rd with views of the Little Medomak Pond. Mature fruit trees, a meandering stream, quintessential barn and even a tennis court, provide all of the extra amenities elevating this beautiful property into the realm of extraordinary. Home is offered fully furnished, if desired.

Single-familyProperty Type

1860Year Built

200.5 acresLot Size

$490Est. Price/Sq.Ft.

5 spacesParking

Listed by Tiffany Look • William Raveis Real Estate

Listed by Jessica Pooley • William Raveis Real Estate

Contact: jessica.pooley@raveis.com

Bought with Seth Cohn • RE/MAX JARET & COHN

Redfin checked: a few seconds ago

•Source:MREIS #1538526

Redfin Estimate

$1,098,418

$148K since sold in November 2022$33K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 74.1% higher than the average sale price ($631K) of 6 comparable homes.

SOLD JUN 30, 2026
$360,000
A
3 beds2 baths2,184 sq ft
215 Robinson Rd, Waldoboro, ME 04572
SOLD JUL 14, 2026
$755,000
B
4 beds3 baths2,920 sq ft
8 Simon Rd, Waldoboro, ME 04572
SOLD JUN 1, 2026
$315,000
C
3 beds2 baths2,340 sq ft
96 Washington Rd, Waldoboro, ME 04572
SOLD JAN 6, 2026
$555,000
D
3 beds2 baths2,345 sq ft
37 Shepard Hill Rd, Union, ME 04862
SOLD NOV 17, 2025
$700,000
E
4 beds2 baths2,468 sq ft
1801 Washington Rd, Waldoboro, ME 04572
SOLD MAY 22, 2026
$1,100,000
F
4 beds3 baths2,105 sq ft
902 Dutch Neck Rd, Waldoboro, ME 04572

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Earn from this home

Rent

$2,223/mo

Redfin rental estimate

List your home for rent

Market trends in 04572, ME

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

97.3%

+1.0% MoM

Median sale price

$440K

$88K MoM

Avg. days on market

31d

40 days MoM

Recently sold homes

4 MoM

New listings for sale

NEW 7 HRS AGO
$375,000
3 beds2 baths1,870 sq ft
180 Bremen Rd, Waldoboro, ME 04572
NEW 24 HRS AGO
$299,900
2 beds1 bath1,025 sq ft
24 Glidden St, Waldoboro, ME 04572
$270,000
3 beds1.5 baths1,900 sq ft
975 Main St, Waldoboro, ME 04572
3D WALKTHROUGH
$765,000
3 beds2 baths1,880 sq ft
763 Dutch Neck Rd, Waldoboro, ME 04572
See all

Provided by Redfin

Sale history for 208 Winston Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,931 (−34.6%)

$259,000 + $412,000

$671,000

2024

$15,176 (+125.2%)

$170,000 + $728,000

$898,000

2023

$6,739 (+15.7%)

$146,000 + $286,000

$432,000

2022

$5,824 (+10.8%)

$130,000 + $286,000

$416,000

2021

$5,256 (−1.1%)

$130,000 + $162,000

$292,000

2020

$5,314 (−0.7%)

$130,000 + $162,000

$292,000

2019

$5,351 (+12.4%)

$130,000 + $164,000

$294,000

2018

$4,761 (+6.1%)

$105,000 + $164,000

$269,000

2017

$4,486 (+3.7%)

$105,000 + $162,000

$267,000

2016

$4,325 (+5.9%)

$105,000 + $162,000

$267,000

2015

$4,085 (+8.0%)

$105,000 + $162,000

$267,000

2014

$3,781

$113,000 + $163,000

$276,000

Tax history for 208 Winston Rd

Year

Property tax

Land + Additions

Assessment*

2025

$9,931 (−34.6%)

$259,000 + $412,000

$671,000

2024

$15,176 (+125.2%)

$170,000 + $728,000

$898,000

2023

$6,739 (+15.7%)

$146,000 + $286,000

$432,000

2022

$5,824 (+10.8%)

$130,000 + $286,000

$416,000

2021

$5,256 (−1.1%)

$130,000 + $162,000

$292,000

2020

$5,314 (−0.7%)

$130,000 + $162,000

$292,000

2019

$5,351 (+12.4%)

$130,000 + $164,000

$294,000

2018

$4,761 (+6.1%)

$105,000 + $164,000

$269,000

2017

$4,486 (+3.7%)

$105,000 + $162,000

$267,000

2016

$4,325 (+5.9%)

$105,000 + $162,000

$267,000

2015

$4,085 (+8.0%)

$105,000 + $162,000

$267,000

2014

$3,781

$113,000 + $163,000

$276,000

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Permits

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

184 Acres

Year renovated

—

Sq. Ft.

480

Year built

1860

Style

Single Family Residential

County

Lincoln County

APN

343250

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 27, 2026.

Property details

Parking

Parking Information
Parking Features: 5 - 10 Spaces, Gravel, On Site, Off Street

Interior

Virtual Tour

Bathroom Information
# of Baths (1/2): 1
# of Baths (Full): 2

Room 1 Information
Type: Kitchen
Level: First

Room 2 Information
Type: Bedroom 4
Level: Second

Room 3 Information
Type: Bonus Room
Level: Second

Room 4 Information
Type: Bedroom 3
Level: Second

Room 5 Information
Type: Bedroom 2
Level: Second

Room 6 Information
Type: Living Room
Level: First

Room 7 Information
Type: Bedroom 1
Level: First

Basement Information
Basement Entry: Interior, Walk-Out Access, Daylight, Full, Unfinished

Interior Features
# of Rooms: 7
Interior Features: 1st Floor Bedroom, 1st Floor Primary Bedroom w/Bath, Attic, Bathtub, One-Floor Living, Other, Shower, Storage, Primary Bedroom w/Bath
Furnished: Furnished
Washer, Refrigerator, Microwave, Electric Range, Dryer
Flooring: Wood, Tile, Carpet
Other Equipment: Satellite Dish, Internet Access Available

Laundry Information
Laundry Features: Washer Hookup

Fireplace Information
# of Fireplaces: 2
Has Fireplace

Exterior

Building Information
Construction Materials: Vinyl Siding, Wood Frame
Foundation Details: Block, Concrete Perimeter, Brick/Mortar
Roof: Metal
Total Building Area (Sq. Ft.): 2,240
Building Area Source: Public Records

Exterior Features
Patio & Porch Features: Deck, Porch
Tennis Court(s)
Other Structures: Outbuilding, Shed(s), Barn(s)

Property Information
Property Sub Type: Single Family Residence
Year Built: 1860
Above-Grade Finished Area (Sq. Ft.): 2,240

Lot Information
Lot Size (Sq. Ft.): $8,733,780
Lot Size (Acres): 200.5
Lot Size Source: Public Records
Lot Features: Well Landscaped, Pasture/Field, Open, Agricultural, Harvestable Crops, Farm, Level, Wooded, Abuts Conservation, Rural
Road Surface Type: Gravel, Dirt
Zoning: Rural

Waterfront Information
Water Body Name: Little Medomak Pond
Water Body Type: Pond
Water View: Yes

Financial

Tax Information
Annual Tax Amount: $5,256
Tax Year: 2021

Utilities

Utility Information
Has Heating
Heating: Stove, Hot Water, Forced Air, Baseboard
Electric: Circuit Breakers
Sewer: Septic Tank, Private Sewer
Water Source: Well, Private
Water Heater: Off Heating System, Oil

Location

Location Information
Unparsed Address: 208 Winston Road, Waldoboro, ME 04572
Directions: From end of Feyler's Corner Rd, cross Old Augusta Rd to Jackson Rd. Winston Rd splits right off Jackson Rd. Property is on the left. GPS Friendly.

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 480
Stories: 2.0
Lot Size: 184 acres
Style: Single Family Residential
Year Built: 1860
Year Renovated: —
County: Lincoln County
APN: 343250

Home facts updated by county records on Jul 27, 2026

Around this home

Schools

Miller School

Public PreK-6 • Assigned • 6.5mi

3/10

Medomak Middle School

Public 7-8 • Assigned • 4.3mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

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

3/10 Heat Factor

7 days above 88° expected this year, 15 days in 30 years

6/10 Wind Factor

27% 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

Waldoboro, ME • 04572

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 7.7 hours in June and 3.3 hours in December, placing it below the U.S. average for solar exposure.

7.7 hrs

3.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.04M – $1.26M

Sell confidently with a local market expert in Waldoboro. 3 minutes to get started.

Nearby similar homes

$995,000

3 beds1 bath863 sq ft

660 Sprague Rd, Waldoboro, ME 04572

$54,500

Land— sq ft

365 Cushing Rd, Cushing, ME 04563

$759,999

3 beds3 baths2,850 sq ft

998 Overlock Hill Rd, Union, ME 04862

3D WALKTHROUGH

$449,900

4 beds1 bath1,753 sq ft

95 Pleasant Point Rd, Cushing, ME 04563

$491,194

3 beds2.5 baths2,172 sq ft

1471 Heald Hwy, Union, ME 04862

NEW 7 HRS AGO

$375,000

3 beds2 baths1,870 sq ft

180 Bremen Rd, Waldoboro, ME 04572

New listings for sale in 04572

NEW 7 HRS AGO

$375,000

3 beds2 baths1,870 sq ft

180 Bremen Rd, Waldoboro, ME 04572

NEW 24 HRS AGO3D WALKTHROUGH

$299,900

2 beds1 bath1,025 sq ft

24 Glidden St, Waldoboro, ME 04572

$270,000

3 beds1.5 baths1,900 sq ft

975 Main St, Waldoboro, ME 04572

3D WALKTHROUGH

$765,000

3 beds2 baths1,880 sq ft

763 Dutch Neck Rd, Waldoboro, ME 04572

Home values near 208 Winston Rd

Data from public records.

Address	Redfin Estimate
64 Winston Rd, Waldoboro, ME 3 Beds \| 1.5 Baths \| 876 Sq. Ft.	$424,565
390 Clarry Hill Ln, Union, ME 3 Beds \| 2 Baths \| 1008 Sq. Ft.	$410,765

Address	Redfin Estimate
153 Winston Rd, Waldoboro, ME 2 Beds \| 1 Baths \| 1560 Sq. Ft.	$341,938
276 Clarry Hill Ln, Union, ME 3 Beds \| 2.5 Baths \| 1475 Sq. Ft.	$546,117

Address	Redfin Estimate
256 Jackson Rd, Waldoboro, ME 3 Beds \| 1 Baths \| 1544 Sq. Ft.	$354,958
156 Clary Hill Rd, Waldoboro, ME 3 Beds \| 1 Baths \| 936 Sq. Ft.	$429,723

Property information provided by MREIS when last listed in 2022. This data may not match . Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 04572, ME

Sale history for 208 Winston Rd

Tax history for 208 Winston Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 04572

Home values near 208 Winston Rd

More real estate resources