A breathtaking home and garden oasis situated in the heart of the Deering Highlands. This historic 1920s hilltop home was built on what was historically part of the Longfellow family estate. The thoughtful orientation of the house maximizes privacy and southern light. A gracious formal foyer with grand stair flows smoothly between the formal living, den and dining room spaces. The superb first floor layout eliminates the need for hallways—the rooms opening to each other, allowing light and family to move throughout the spaces easily. A year round sunroom with NanaWall door that fully folds back to open to the entry patio welcomes the outdoors in in the summer and is a snow globe wonder in the winter. The kitchen is well appointed with windows overlooking the stunning garden and grounds and has a large abutting butler's pantry complete with a second dishwasher and maximized storage. The gracious stairway leads to a spacious primary suite with 5 fixture bathroom and gas fireplace. Hidden-door built-ins line the hallway as you make your way to the next two bedrooms that share access to a hall bathroom with restored jade glass vintage tiles. The final two bedrooms and abutting Jack-and-Jill bathroom enjoy custom wallpaper and window treatments. The home boasts central air with an efficient hybrid gas/heat pump system throughout. Other recent upgrades include a new roof and exterior paint. The attached garage and mudroom make coming and going easy in all seasons. The gardens, designed by a world renowned horticulturist, are the real showstopper. The greenhouse, complete with heat and electricity, will inspire. The garden produces stunning texture and color, visible from all parts of the home, from early spring through the fall. You will not see a garden in Portland that rivals it—truly transporting. The neighborhood is a hidden treasure, a short distance to amazing amenities including restaurants, bakeries and shops—you can even walk to a show at Thompson's Poin
Single-familyProperty Type
1920Year Built
0.45 acresLot Size
$445Est. Price/Sq.Ft.
2 car garageParking
Listed by Alessandra Malone• Waypoint Brokers Collective
Contact: ali@waypointbrokers.com
Bought with Sandra Shapiro-Hurt• Legacy Properties Sotheby's International Realty
Gorgeous, stately home in Portland's desirable Deering Highlands. Phenomenal layout, spacious rooms, historic details & amazing yard. Extensively renovated in 12-13, includes new heat system, gourmet kitchen. Stunning turn-key property not to be missed.
MREIS #1066984
Aug 21, 2012
Listed
$499,000
$106/sq ft
Year
Property tax
Land + Additions
Assessment*
2024
$20,202 (+4.2%)
$144,400 + $1,201,500
$1,345,900
2023
$19,394 (+5.9%)
$144,400 + $1,201,500
$1,345,900
2022
$18,318 (+4.8%)
$144,400 + $1,201,500
$1,345,900
2021
$17,483 (+23.6%)
$144,400 + $1,201,500
$1,345,900
2020
$14,149
$144,400 + $462,600
$607,000
2019
$14,149 (+29.4%)
$144,400 + $462,600
$607,000
2018
$10,932 (+3.8%)
$40,100 + $446,200
$486,300
2017
$10,528 (+2.6%)
$40,100 + $446,200
$486,300
2016
$10,266 (+2.3%)
$40,100 + $446,200
$486,300
2015
$10,032 (+3.1%)
$40,100 + $446,200
$486,300
2014
$9,726
$40,100 + $446,200
$486,300
Tax history for 20 Highland St
Year
Property tax
Land + Additions
Assessment*
2024
$20,202 (+4.2%)
$144,400 + $1,201,500
$1,345,900
2023
$19,394 (+5.9%)
$144,400 + $1,201,500
$1,345,900
2022
$18,318 (+4.8%)
$144,400 + $1,201,500
$1,345,900
2021
$17,483 (+23.6%)
$144,400 + $1,201,500
$1,345,900
2020
$14,149
$144,400 + $462,600
$607,000
2019
$14,149 (+29.4%)
$144,400 + $462,600
$607,000
2018
$10,932 (+3.8%)
$40,100 + $446,200
$486,300
2017
$10,528 (+2.6%)
$40,100 + $446,200
$486,300
2016
$10,266 (+2.3%)
$40,100 + $446,200
$486,300
2015
$10,032 (+3.1%)
$40,100 + $446,200
$486,300
2014
$9,726
$40,100 + $446,200
$486,300
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Beds
5
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.46 Acres
Year renovated
—
Sq. Ft.
4,582
Year built
1920
Style
Single Family Residential
County
Cumberland County
APN
118745
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 27, 2026.
Property details
Parking
Parking Information
Has Garage
Attached Garage: Yes
# of Garage Spaces: 2
Parking Features: Auto Door Opener, Basement, 1 - 4 Spaces, Paved, Inside Entrance, Tandem, Underground
Vehicle Storage: 2 Car, Attached, Auto Door Opener, Direct Entry to Living, Tandem, Underground, Basement