Deering Highlands, ME homes for sale & real estate

Deering Highlands, ME Homes for Sale

Nestled in the vibrant Woodfords/Deering Center neighborhood of Portland, where tree-lined streets meet the pulse of local cafés and boutiques, this home's iconic turquoise shingle siding gleams under the Maine sky, crowned by a steep gabled roof and accented with crisp white trim that pops like sea foam against the blue. A grand wraparound front porch beckons with its classic columns, perfect for morning coffee or evening unwinding with neighborhood views. With 5-bedrooms and 2-baths, this Victorian home blends timeless character with vibrant charm. Owned and lovingly maintained for 25 years, the home reflects a unique artistic spirit while offering comfort, efficiency, and space fo

Deering Highlands, ME Homes for Sale

At the base of Deering Highlands, blocks from Back Cove, and firmly in Portland's Oakdale neighborhood, this updated Victorian offers convenience, charm, and value. Many updates and upgrades—including extensive siding work, fresh exterior paint, and a newer roof—make it move-in ready. The remarkably affordable price also reflects the home's upside potential, as similar properties in the area have sold for 1M or more. Although just over 2,000 square feet, the layout lives large with plenty of space for friends, family, and work-from-home flexibility. Inside you'll find a south-facing mudroom/sunroom, eat-in kitchen, formal dining, side sunroom, and spacious living room. Upstairs

Deering Highlands, ME Homes for Sale

Welcome to 296 Brighton Ave. .. .. as you enter the front door you will appreciate the timeless beauty of the staircase to the second floor. Many period details throughout. The first floor offers hardwood flooring throughout the large living room with fireplace and dining room with lovely built-ins. The kitchen has ample cabinets and a large deep ceramic sink. Up to the second floor with hardwood flooring throughout offering 4 bedrooms. Plenty of room and added storage area in the attic. There is also a full basement with plenty of added storage which you can access the garage. All situated on a corner lot with a nice side yard. Minutes to shopping, Rock Row down the street and intown Portl

Deering Highlands, ME Homes for Sale

Outstanding turnkey property! This exceptional investment features three units with three bedrooms and two full bathrooms, complemented by two additional bonus units. The property is in impeccable condition, having undergone extensive renovations. This property represents great income potential with separate heating and electricity for each unit and a convenient shared laundry facility. Don't miss out on this incredible opportunity!

Deering Highlands, ME Homes for Sale

Large, classic 3-decker with over 3,800 SF of living area, a driveway and garage. All of the units are similar but with interesting differences: an updated kitchen on the 1st floor creates an open living space and a unique 3bd/2bath setup. The 2nd floor is spacious with an enclosed porch for additional storage. The 3rd floor includes a bonus bedroom in the front (making it a 3 bd) plus a quasi-finished room on the rear porch. Located conveniently between the Rosemont and Oakdale neighborhoods with quick and easy access to shopping, restaurants, entertainment and the interstate. An investment-minded owner-occupant will have a great long-term asset and significant income potential. Possible s

Deering Highlands, ME Homes for Sale

Welcome to 160 Craigie Street—where history, style, and location converge in one unforgettable home. Designed by architect John Calvin Stevens, this residence showcases timeless craftsmanship alongside thoughtful, contemporary updates. Situated on a rare double lot, it stands out as a true gem in one of Portland's most desirable neighborhoods. A gracious exterior, framed by mature landscaping and a fully fenced yard, offers both exceptional curb appeal and privacy. Inside, original architectural details—trim, built-ins, and a wood-burning fireplace—pay homage to the home's storied past, while recent enhancements ensure modern comfort and convenience. The flow of the home i