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)
Local Information
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Description
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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
No Info
Outdoor
Porch, Deck
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info
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 History for 249 Simon Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 06/08/2016 | $200,000 | Sold | N/A |
| 08/19/2014 | $250,000 | ListingRemoved | Agent Provided |
| 05/08/2014 | $250,000 | Listed For Sale | Agent Provided |
| 11/14/2010 | $275,000 | ListingRemoved | Agent Provided |
| 05/22/2010 | $275,000 | Listed For Sale | Agent Provided |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $5,391 |
| Assessment | $319,000 |
Home facts updated by county records
Comparable Sales for 249 Simon Rd
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 | |
0.58 | 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 | |
1.08 | Single-Family Home | $290,000 | 11/19/25 | 3 | 1.5 | 1,248 | |
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 | |
1.82 | Single-Family Home | $377,000 | 09/08/25 | 3 | 1.5 | 1,512 | |
1.71 | Single-Family Home | $283,000 | 08/13/25 | 3 | 1 | 1,160 | |
2.00 | Single-Family Home | $595,000 | 10/01/25 | 3 | 2 | 2,966 |
Assigned Schools
These are the assigned schools for 249 Simon Rd.
- Medomak Valley High School
- 9-12
- Public
- 563 Students
5/10GreatSchools RatingParent Rating AverageN/AOther Review18y ago - Miller School
- PK-6
- Public
- 336 Students
3/10GreatSchools RatingParent Rating AverageMy son just completed the 1st grade here, and we had a very positive experience. He was not in the public school system prior to this, and I was worried. He has a anxiety diagnosis, as well as some oppositional behavior, along with fine motor skill delays. Just before the school year started, I had several meetings with staff at the school: principal and counselor, primarily. I was greatly reassured. The counselor helped me work out a plan to get him riding the school bus (something he learned to love quickly, rather than fear). They placed him with a terrific teacher who provided kind, but firm, guidance for him. I was also able to get him into OT without too much trouble (1 phone call) to help with fine motor skills and sensory integration issues he has. I feel pretty good about Miller. (Also-peanut ban was lifted this past year.)Parent Review15y ago - Medomak Middle School
- 7-8
- Public
- 293 Students
6/10GreatSchools RatingParent Rating AverageGreat school, very high quality teachers, and great learning experiences.Student Review3y ago 
Check out schools near 249 Simon Rd.
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
2.56 ACRESThe MidcoastHome Real Estate Co., Active
2.6 ACRESWaterfront Properties of Maine, Active
See more homes for sale inWaldoboro
Off Market Homes Near 249 Simon Rd
SOLDMAY 1, 2026Pooley Realty Group, Closed
SOLDMAR 18, 2026Portside Real Estate Group, Closed
SOLDMAR 9, 2026Orff Realty Corp, Closed
SOLDFEB 17, 2026The New England Real Estate Company, LLC, Closed
SOLDFEB 10, 2026Lone Pine Real Estate Company, Closed
SOLDFEB 2, 2026Pooley Realty Group, Closed
SOLDJAN 15, 2026Peninsula Properties, Closed
SOLDJAN 8, 2026
SOLDDEC 11, 2025RE/MAX JARET & COHN, Closed- SOLDDEC 10, 2025
- See more homes for sale inWaldoboro
Homes for rent near 249 Simon Rd
249 Simon Rd, Waldoboro, ME 04572 is a 3 bedroom, 2 bathroom, 2,300 sqft single-family home built in 1900. This property is not currently available for sale. 249 Simon Rd was last sold on Jun 8, 2016 for $200,000. The current Trulia Estimate for 249 Simon Rd is $476,600.