8 Simon Road

Off Market

8 Simon Road

Waldoboro ME 04572

2920 sq. ft.

2918520 sq. ft.

Single-Family

Last sold for $755,000

Avary Otis, last sold this property on 14 July 2026 after -51 days on market.

Overview

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

Features

4 bedrooms

3 bathrooms

2 carspaces

2 garage spaces

2920 sq. ft. floor area

2918520 sq. ft. lot size

Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Waldoboro over the last 12 months, the estimated median property value of 8 Simon Road is $355k.

Median value

$355k

Estimated value range

$155k - $1.18m

Median days on market

Estimated value trend

increase over the last 12 months

Average days on market is based on recent, comparable sales in Waldoboro. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 8 Simon Road

2026

Sold

$755,000

14 Jul 2026 by Avary Otis, of Camden Coast Real Estate

Happy sellers in Waldoboro

We have insufficient information to provide an overview of customer satisfaction for Waldoboro. Viewing the agent profiles, reviews and sales for Waldoboro can provide insights for this location.

Local market activity for 4 bedroom single-family properties in Waldoboro

In the last 12 months, 10 four-bedroom single-family properties similar to 8 Simon Road, have been sold.

This represents a 100% decrease in four-bedroom single-family properties sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Waldoboro for a market analysis.

Cindy Powell

at Realty One Group Compass | Maine

(113 reviews)

Get a market analysis

James Pepin

at Sprague & Curtis Real Estate

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Tim Dunham

at Tim Dunham Realty

(77 reviews)

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Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Waldoboro

Cindy Powell

Sellers who recommend Cindy Powell have praised them for being local expert, responsive, clear communication, supportive, patient, dedicated, and well-prepared