249 Simon Rd
Waldoboro, ME 04572
3 Beds
2 Baths
2,300 sqft (on 70 acres)
3 Beds
2 Baths
2,300 sqft
(on 70 acres)
Home Value
Trulia Estimate
$466KSince last month
Decreased$4K (-0.9%)Since last year
Decreased$18K (-3.7%)Since last sale
Increased$261K (+130.7%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +128% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $461K |
| July 2026 | $466K |
| June 2026 | $470K |
| May 2026 | $471K |
| April 2026 | $455K |
| March 2026 | $456K |
| February 2026 | $442K |
| January 2026 | $456K |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.53 | Single-Family Home | $700,000 | 11/17/25 | 4 | 2 | 2,468 | |
0.30 | Single-Family Home | $585,000 | 09/05/25 | 3 | 2 | 2,660 | |
0.78 | Single-Family Home | $755,000 | 07/14/26 | 4 | 3 | 2,920 | |
0.58 | Single-Family Home | $293,000 | 09/19/25 | 3 | 1 | 1,288 | |
1.05 | Single-Family Home | $218,000 | 01/20/26 | 3 | 2 | 1,296 | |
1.30 | Single-Family Home | $360,000 | 06/30/26 | 3 | 2 | 2,184 | |
1.08 | Single-Family Home | $290,000 | 11/19/25 | 3 | 1.5 | 1,248 | |
1.11 | Single-Family Home | $435,000 | 05/29/26 | 3 | 2.5 | 1,792 | |
1.66 | Single-Family Home | $295,000 | 11/12/25 | 3 | 2 | 1,512 | |
1.64 | Single-Family Home | $345,000 | 05/01/26 | 3 | 1 | 1,310 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.30 | $602,600 | 3 | 2 | 2,660 | Off Market | |
0.48 | - | - | - | - | Off Market | |
0.50 | $236,400 | 3 | 2 | - | Off Market | |
0.53 | $700,000 | 4 | 2 | 2,468 | Recently Sold | |
0.60 | $219,000 | 3 | 2 | 1,064 | For Sale | |
0.68 | - | - | - | - | Off Market | |
0.78 | - | - | - | - | Off Market | |
0.78 | $755,000 | 4 | 3 | 2,920 | Recently Sold | |
0.78 | $267,800 | 3 | 2 | 1,280 | Off Market | |
0.81 | $399,200 | 2 | 1 | 1,196 | Off Market | |
0.85 | - | - | - | - | Off Market | |
0.88 | - | - | - | - | Off Market |
Local Information
- Map ViewExplore the area around 249 Simon Rd.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1900
Lot Size
70 acres
Living Area
2,300 sqft
Price/Sqft
$202
About this House
Lovely restored Farmhouse in beautiful country setting of 70 acres includes horse paddock and barn, potting shed, pretty gardens, and Farmer's porch. Three bedrooms, 2 baths plus a den and office. Close to Moody's Diner and down east area.
249 Simon Rd, Waldoboro, ME 04572 is a 3 bedroom, 2 bathroom, 2,300 sqft single-family home built in 1900. It last sold for $200,000 on Jun 8, 2016. It is currently off market. The Trulia Estimate is $465,700, with a rent estimate of $2,925/month.
Home Details for 249 Simon Rd
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Heating & Cooling Heating: Forced Air, OtherHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Hardwood, Linoleum Vinyl |
Interior Details Number of Rooms: 9 |
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Exterior Home Features Roof: OtherDeckExterior: WoodPorch |
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Year Built Year Built: 1900Year Updated: 1990 |
Property Type / Style Property Type: Single Family HomeArchitecture: Other |
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Units in Building: 1 |
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Lot Area: 70.00 acres |
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Greenhouse |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Jun 8, 2016 Source: N/A | Sold | $200,000 |
Aug 19, 2014 Source: Agent Provided | ListingRemoved | $250,000 |
May 8, 2014 Source: Agent Provided | Listed For Sale | $250,000 |
Nov 14, 2010 Source: Agent Provided | ListingRemoved | $275,000 |
May 22, 2010 Source: Agent Provided | Listed For Sale | $275,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $5,391 | $319,000 |
Home facts updated by county records
Market trends in Waldoboro
Last updated July 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
30
5MoM
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Around this home
What Locals Say about Waldoboro
At least 4 Trulia users voted on each feature.
100 % Say car is needed
100 % Say people would walk alone at night
100 % Say there's holiday spirit
100 % Say yards are well-kept
83 % Say parking is easy
83 % Say there's wildlife
80 % Say it's quiet
57 % Say kids play outside
50 % Say neighbors are friendly
50 % Say it's dog friendly
43 % Say they plan to stay for at least 5 years
40 % Say there are community events
33 % Say streets are well-lit
25 % Say there are sidewalks
20 % Say it's walkable to restaurants
17 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
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Apartments for Rent
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Homes for sale near 249 Simon Rd
2.5 ACRESBlue Lobster Real Estate, Active
1.29 ACRESPooley Realty Group, Active
1.8 ACRESRE/MAX JARET & COHN, Active
See more homes for sale inWaldoboro
Off Market Homes Near 249 Simon Rd
SOLDJUL 24, 2026Pooley Realty Group, Closed
SOLDJUL 22, 2026Midcoast Home/Sea Glass, Closed
SOLDJUL 8, 2026RE/MAX JARET & COHN, Closed
SOLDJUN 30, 2026Portside Real Estate Group, Closed
SOLDJUN 29, 2026Better Homes & Gardens Real Estate/The Masiello Group, Closed
SOLDJUN 15, 2026Epique Realty, Closed
SOLDJUN 1, 2026Lone Pine Real Estate Company, Closed
SOLDMAY 29, 2026Better Homes & Gardens Real Estate/The Masiello Group, Closed
SOLDMAY 22, 2026Pooley Realty Group, Closed- See more homes for sale inWaldoboro
Frequently asked questions about 249 Simon Rd
- What is 249 Simon Rd estimated to be worth?Trulia's estimated value for 249 Simon Rd in Waldoboro, ME is $465,700.
- What is the price history for 249 Simon Rd?249 Simon Rd in Waldoboro, ME last sold for $200,000 in June 2016.
- Is Waldoboro a buyer's or seller's market?Waldoboro is currently a balanced market, based on recent for-sale activity.
- What are the closest schools to 249 Simon Rd?The closest schools to 249 Simon Rd in Waldoboro, ME are Medomak Middle School (rated 6/10), Medomak Valley High School (rated 5/10), Miller School (Pre-K/Elementary, rated 3/10).
- How big is the lot at 249 Simon Rd?The lot at 249 Simon Rd in Waldoboro, ME is about 70 acres.