8 Simon Road
Waldoboro, ME 04572
4 Beds
3 Baths
2,920 sqft (on 67 acres)
$755,000
Last Sold: Jul 14, 2026
1% over list $749K
$259/sqft
$755,000
Last Sold: Jul 14, 2026
1% over list $749K
$259/sqft
4 Beds
3 Baths
2,920 sqft
(on 67 acres)
Local Information
- Map ViewExplore the area around 8 Simon Road.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Last check for updates: about 11 hours ago
Listed by Camden Coast Real Estate
Bought with: Engel & Volkers Casco Bay
Source: Maine Listings, MLS#1665007
Description
Step into this truly one-of-a-kind property where historic charm, thoughtful craftsmanship, and a breathtaking pastoral setting come together on 67 picturesque acres of rolling hay fields, mature woods, and open countryside. Privately situated yet conveniently located near Union Village, Route 17, Rockland, and the Midcoast, this remarkable property combines beauty, versatility, and recreation. At the heart of the property is a beautifully preserved 1800s Cape rich with character. Original features include exposed hand-hewn beams, wide wood floors, and a restored kitchen fireplace with a traditional beehive oven. A stunning Rockport post-and-beam addition completed in 2022 enhances the home with soaring ceilings, abundant natural light, warm wood finishes, a beautiful brick chimney, and sweeping views of the surrounding landscape. The flexible layout includes four potential bedrooms, including ensuite bedrooms on both the first and second floors, three full bathrooms, expansive gathering spaces, and two full kitchens; perfect for multigenerational living, duplex, or an event space. A spacious dining area with French doors open directly to the deck, creating a seamless connection to the outdoors. Additional improvements include a detached two-car garage, a heated 24' x 25' woodworking shop, unfinished space above the garage with potential for guest quarters or a studio, and a finished heated 14' x 25' office ideal for remote work or a home-based business. Outside, approximately 1.5 miles of ITS snowmobile trails connect all the way to Fort Kent, creating an incredible recreational or equestrian opportunity, and the field has potential for a 1,500' runway. While mature maple trees, lilacs, open pastureland, and wooded acreage complete the peaceful setting, two ground-mounted solar arrays provide power to the property and keep utility expenses extremely low. A rare blend of history, craftsmanship, and recreation that must be experienced in person to be fully appreciate
8 Simon Road, Waldoboro, ME 04572 is a 4 bedroom, 3 bathroom, 2,920 sqft single-family home built in 1825. It last sold for $755,000 on Jul 14, 2026 (1% above the $749,000 asking price). It is currently off market. The Trulia Estimate is $747,300, with a rent estimate of $3,549/month.
Home Highlights
Parking
Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
$259/sqft
Listed
42 days ago
Home Details for 8 Simon Road
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MLS Status: Closed |
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Interior Details Basement: Interior Entry,Full,UnfinishedNumber of Rooms: 9Types of Rooms: Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Den, Dining Room, Great Room, Kitchen |
Beds & Baths Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 2920 Square Feet |
Heating & Cooling Heating: Direct Vent Heater,Heat Pump,Wood StoveHas CoolingAir Conditioning: Heat PumpHas HeatingHeating Fuel: Direct Vent Heater |
Fireplace & Spa Number of Fireplaces: 3Has a Fireplace |
Gas & Electric Electric: Circuit Breakers, Generator Hookup, Photovoltaics Seller Owned |
Windows, Doors, Floors & Walls Flooring: Wood |
Levels, Entrance, & Accessibility Floors: Wood |
View Has a ViewView: Fields, Scenic |
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Exterior Home Features Roof: ShinglePatio / Porch: DeckFoundation: Slab, StoneNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageParking Spaces: 2Parking: Gravel,1 - 4 Spaces,Detached,Storage |
Frontage Road Surface Type: PavedNot on Waterfront |
Water & Sewer Sewer: Private Sewer |
Finished Area Finished Area (above surface): 2920 Square Feet |
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Year Built Year Built: 1825 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod |
Building Construction Materials: Wood Frame, Shingle Siding |
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Price List Price: $749,000Price Per Sqft: $259/sqft |
Status Change & Dates Off Market Date: Sun Jun 07 2026 |
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Direction & Address City: Waldoboro |
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Building Area Building Area: 2920 Square Feet |
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Lot Area: 67 Acres |
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BasementMls Number: 1665007Attribution Contact: info@camdencoast.comAbove Grade Unfinished Area: 2920 |
Price History for 8 Simon Road
| Date | Price | Event | Source |
|---|---|---|---|
| 07/14/2026 | $755,000 | Sold | Maine Listings #1665007 |
| 06/08/2026 | $749,000 | Pending | Maine Listings #1665007 |
| 06/02/2026 | $749,000 | Listed For Sale | Maine Listings #1665007 |
| 11/15/2019 | $225,000 | Sold | N/A |
| 10/09/2019 | $225,000 | Pending | Agent Provided |
| 06/18/2019 | $225,000 | Listed For Sale | Agent Provided |
Market trends in Waldoboro
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
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Price per sq ft
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Available listings
35
12MoM
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $6,912 |
| Assessment | $409,000 |
Home facts updated by county records
Comparable Sales for 8 Simon Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.68 | Single-Family Home | $700,000 | 11/17/25 | 4 | 2 | 2,468 | |
0.96 | Single-Family Home | $585,000 | 09/05/25 | 3 | 2 | 2,660 | |
1.01 | Single-Family Home | $435,000 | 05/29/26 | 3 | 2.5 | 1,792 | |
0.86 | Single-Family Home | $218,000 | 01/20/26 | 3 | 2 | 1,296 | |
0.95 | Single-Family Home | $290,000 | 11/19/25 | 3 | 1.5 | 1,248 | |
1.13 | Single-Family Home | $377,000 | 09/08/25 | 3 | 1.5 | 1,512 | |
2.01 | Single-Family Home | $360,000 | 06/30/26 | 3 | 2 | 2,184 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
FOR SALE3.16 ACRESNewcastle Realty, Active
OFF MARKETBetter Homes & Gardens Real Estate/The Masiello Group, Closed
SOLDNOV 17, 2025Better Homes & Gardens Real Estate/The Masiello Group, Closed
FOR SALE
3D VIEW2 ACRESPooley Realty Group, Active
SOLDJAN 20, 2026NextHome Experience, Closed
FOR SALE27.4 ACRESGregory W. Peet Real Estate, Active
FOR SALE5.5 ACRESRealty of Maine, Active
FOR SALE4.13 ACRESStartPoint Realty, Active
Assigned Schools
These are the assigned schools for 8 Simon Road.
- Medomak Valley High School
- 9-12
- Public
- 561 Students
5/10GreatSchools RatingParent Rating AverageN/AOther Review18y ago - Miller School
- PK-6
- Public
- 361 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 Review16y ago - Medomak Middle School
- 7-8
- Public
- 259 Students
6/10GreatSchools RatingParent Rating AverageGreat school, very high quality teachers, and great learning experiences.Student Review3y ago 
Check out schools near 8 Simon Road.
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.
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Apartments for Rent
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Homes for sale near 8 Simon Road
- 4.13 ACRESStartPoint Realty, Active
2.5 ACRESBlue Lobster Real Estate, Active
9.62 ACRESNewcastle Realty, Active
0.68 ACRESRE/MAX JARET & COHN, Active
1.29 ACRESPooley Realty Group, Active
NEW CONSTRUCTION3.01 ACRESBetter Homes & Gardens Real Estate/The Masiello Group, Active
See more homes for sale inWaldoboro
Off Market Homes Near 8 Simon Road
SOLDJUL 8, 2026RE/MAX JARET & COHN, Closed
SOLDJUN 26, 2026RE/MAX JARET & COHN, Closed
SOLDMAY 29, 2026Better Homes & Gardens Real Estate/The Masiello Group, Closed
SOLDJAN 8, 2026- SOLDDEC 10, 2025
SOLDDEC 9, 2025Lone Pine Real Estate Company, Closed
SOLDNOV 18, 2025Lash Realty Group, Closed- SOLDNOV 17, 2025Better Homes & Gardens Real Estate/The Masiello Group, Closed
- See more homes for sale inWaldoboro
Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified.
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