Portland Real Estate

Welcome to Portland, Connecticut – a hidden gem nestled in Middlesex County, where picturesque landscapes and a vibrant community come together to create a truly charming place to call home. Situated along the banks of the Connecticut River, Portland boasts stunning natural beauty, offering residents and visitors alike a serene escape from the hustle and bustle of city life.

Known for its rich history, Portland is home to a variety of historic sites, including the iconic Portland Brownstone Quarries, which played a significant role in the town's development in the 19th century. Today, you can explore these fascinating remnants while enjoying scenic views of the river and surrounding hills.

The town's vibrant community spirit is evident in its numerous local events and festivals throughout the year, including the popular Portland Fair and summer concert series. Families will appreciate the excellent school system and the abundance of recreational opportunities, from hiking and biking trails to parks and playgrounds that cater to all ages.

For those who enjoy the outdoors, the nearby Wadsworth Falls State Park offers a perfect backdrop for hiking and picnicking, while the Connecticut River provides opportunities for kayaking and fishing. With its convenient location just a short drive from Hartford and Middletown, Portland offers a perfect blend of small-town charm and easy access to urban amenities.

Whether you're looking to settle down in a welcoming community or seeking a peaceful retreat, Portland, CT, offers a delightful lifestyle that truly embodies the best of Connecticut living. Come discover the warmth and charm of this beautiful town – your new home awaits!

Newest Listings in Portland

$477,500

4 Beds ⋅ 3 Baths ⋅ 24203462 MLS

Welcome to 394 Main Street, a spacious multi-family located in the desirable Portland area. With its substantial footprint and versatile layout, this property presents an excellent opportunity for an owner occupant, extended household, or investor looking to add a valuable property to their portfolio. Whether you're looking to occupy one unit while generating rental income from another, accommodate extended family, or explore the property's investment potential, 394 Main Street offers plenty of possibilities. Located close to local shopping, dining, schools, parks, and area amenities. Portland's convenient location also provides easy access to surrounding communities and major commuter routes. With its spacious layout, multi-family versatility, and desirable Portland location, this property offers an exciting opportunity for buyers seeking both flexibility and potential. Bring your vision and make 394 Main Street your next investment or home! Schedule your private showing today!

394 Main St, Portland

$849,900

3 Beds ⋅ 4 Baths ⋅ 24200612 MLS

Rarely available, this exceptional custom built home sits on 2.03 acres bordering the Portland Golf Course. Welcome to 41 Gildersleeve Road an oversized Cape, offering approximately 3,355 square feet of thoughtfully designed living space. The open-concept floor plan features spacious rooms, quality finishes, and an inviting layout designed for both everyday living and entertaining. Beautiful hardwood floors flow throughout the home, complemented by a gas fireplace framed by custom built-ins. On chilly evenings, gather around the fire and enjoy the warmth and comfort of this welcoming space. The thoughtfully designed floor plan creates an easy flow between the living, dining, and entertaining areas. Large windows fill the home with abundant natural light, enhancing the open and airy feel throughout. The home currently offers three bedrooms and three-and-a-half baths, with the flexibility of two potential primary bedroom suites-one on the first floor and another on the second floor. This versatile layout provides options to suit a variety of living arrangements. Convenience continues with laundry hookups on the first floor, as well as a dedicated laundry room in the basement. A spacious first-floor office provides an ideal work-from-home space and could also be used as a fourth bedroom.

41 Gildersleeve Rd, Portland

$339,900

2 Beds ⋅ 1 Baths ⋅ 24202613 MLS

This is the perfect starter home or a great option for downsizing. Enjoy hardwood floors throughout the main floor, a beautiful kitchen, and an updated bathroom. This home is protected by a 50-year architectural roof, and the vinyl siding is less than 5 years old. The full basement with walkout provides exceptional flexibility. This inviting home backs onto peaceful woods, offering privacy and a serene natural setting. Schedule your tour before it's gone. The sale is subject to the seller securing a house. They are actively looking.

148 Old Marlborough Tpke, Portland

$195,000

2 Beds ⋅ 1 Baths ⋅ 24201610 MLS ⋅ Atrium Of Portland BLDG.

Welcome to The Atrium, a desirable 55+ community tucked into a lightly wooded, peaceful setting in historic Portland,former Brownstone capital of Connecticut. If you're looking to downsize without giving up comfort, convenience, or location, this affordably priced first-floor 2 bedroom condo is an opportunity worth seeing. Rarely available, this spacious two-bedroom unit offers easy single-level living with the added convenience of in-unit laundry and a secure building. Enjoy the tranquility of a country setting while being just minutes from the Connecticut River and the charming center of Portland, where quaint shops, local restaurants, and community charm await. Just across the river, neighboring Middletown expands your options with vibrant riverfront activities, festivals, shopping, entertainment, and a diverse selection of dining. The Atrium's central Connecticut location makes it easy to enjoy everything the area has to offer while providing a convenient commute to Hartford and surrounding communities. Whether you're ready to simplify, looking for a more manageable home, or simply want to enjoy the benefits of 55+ living, this rarely offered two-bedroom condo combines affordability, convenience, and a wonderful setting. Come discover why The Atrium could be the perfect place to call home!

1 Brush Pasture Ln Unit 103, Portland

$999,900

2 Baths ⋅ 24202393 MLS

This exceptional industrial property offers 1.54 acres of prime real estate in a central location right outside of Middletown. Featuring new roof and over 13,000 sqft with three spacious bays, each equipped with a 14 foot high automatic overhead door and its own crane for handling heavy materials and equipment. Additionally, one bay includes an in-ground hydraulic lift. 18-foot ceilings offer ample vertical space, making it ideal for a wide range of industrial operations. With over an acre and a half there is lots of outdoor space for maneuvering and storing equipment. The owner has completed all necessary environmental remediation. We have a Phase 1 report available for review. Strategically located right outside of Middletown, this location offers convenient access to major highways and transportation routes. Whether you're handling large shipments, manufacturing complex products, or need an environment for equipment storage, 251 Freestone is a fantastic investment and opportunity!

251 Freestone Ave, Portland

$375,000

3 Beds ⋅ 1 Baths ⋅ 24200519 MLS

3 bedroom Ranch on lovely location on a cul-de-sac road. This ranch offers 3 nice size bedrooms (note - town hall lists as a 2 bedroom). Oak floors in bedrooms and living room, the livingroom has wood burning fireplace and a dining area with corner hutch. Kitchen can be closed off by pocket door. House originally had 1 car garage, an oversize additional bay was added and plumbed to have radiant heat in floor. This home has a nice layout, is solid but needs updating to the kitchen and bathroom. All functional but really needs remodel. Breezeway between house and garage. Yard is rolling so there is level area's. Shed on rear of property. Basement unfinished.

3 Edwards Rd, Portland

$450,000

4 Beds ⋅ 3 Baths ⋅ 24200187 MLS

Timeless and charming colonial offers stunning details around every corner. First floor boasts a formal dining room with built-ins, full living room and den (each with a fireplace), kitchen and keeping room, foyer, and half bath. French doors lead from the dining room to a screened porch perfect for outdoor lounging and taking in the idyllic 1.5 acre property complete with 2 car garage as well as a barn. Upper level boasts a hallway lined with built-ins, 4 bedrooms, 2 full baths, and a walk-up attic offering plenty of storage in addition to full, unfinished basement.

98 Maple Rd, Portland

$250,000

3 Beds ⋅ 2 Baths ⋅ 24198961 MLS

Calling all INVESTORS and BOATERS, as well as anyone else willing to give this cozy nest some TLC! Situated walking distance to the NEW River Bend Landing, a short distance to Birdon Marina and a hop, skip and a jump to the Members-Only Meriden Motor Boat Club, all this home needs, is a vision to bring this Cape to life! Brand new furnace and all new pipes; half bathroom has started a transformation to a full 2nd bathroom; the primary bedroom has potential for a walk-in closet/office/additional space and the full bathroom, on the upper level by the main bedrooms, has been updated!

164 Airline Ave, Portland

$459,900

2 Beds ⋅ 2 Baths ⋅ 24190743 MLS

Welcome to 64 Jobs Gate 2, a custom-built Contemporary Colonial offering waterfront living at its finest on crystal-clear Jobs Pond. Enjoy water views from every room, a private beach, and your own floating dock-perfect for swimming, kayaking, fishing, or simply relaxing by the water. The home features three fireplaces, recessed lighting throughout, solid oak finishes, custom kitchen cabinetry, central vacuum (system installed but no unit), and rain-sensor skylights in the primary bedroom. Recent updates include a newer roof, remodeled bathrooms, newer bedroom flooring, and a recently painted exterior. The home is also hardwired for a generator. Ideal as a year-round residence or seasonal retreat, this peaceful property is across from Arrigoni Winery & Cider Co. and River Ridge Farm, 15 minutes from the Air Line State Park Trail, 12 minutes from Stop & Shop in East Hampton, and 20 minutes from Glastonbury.

64 Jobs Gate, Portland

$499,900

3 Beds ⋅ 2 Baths ⋅ 24198960 MLS

This classic 1955 country Cape is set on 2.05 acres in a peaceful wooded setting in Portland, yet just minutes from Glastonbury and Route 2. The first floor offers a spacious family room with wood stove, kitchen, dining room, laundry room, formal living room, full bath, and a versatile additional room currently being used as a bedroom. This flexible space could also serve as a home office, den, guest room, or study, depending on your needs. With multiple adaptable spaces, this home offers the flexibility to fit your lifestyle now and as your needs change. Upstairs, you'll find three comfortable bedrooms plus a fourth room that can easily adapt to your needs as well as another full bath. This house is surprisingly spacious! The full walkout basement includes a home gym and under-house garage. Two driveways provide abundant parking and convenient space for vehicles, trailers, or equipment. A true highlight is the extraordinary 14' x 24' handcrafted timber-frame barn - an inspiring space with remarkable craftsmanship, ideal for a workshop, studio, or creative retreat. This is a property that truly must be seen to be appreciated.

251 Thompson Hill Rd, Portland

$275,000

3 Beds ⋅ 2 Baths ⋅ 24198665 MLS

Tucked away on a private rear lot off Main Street, this charming 3-bedroom, 2-bath Cape offers a great opportunity to make it your own! The .41-acre property features a spacious side yard with plenty of room for outdoor enjoyment, gardening, or entertaining. The first floor offers an open-concept living room, dining area, and kitchen with high ceilings, plus a full bathroom. Upstairs, you'll find three bedrooms and a second full bathroom. A full basement provides excellent storage space and utility area. The home is connected to public utilities and offers convenient access to local amenities. While the home could use some fresh paint and new flooring, it provides a solid opportunity to add your personal style and build equity. Conveniently located approximately 30 minutes from the Connecticut shoreline and Hartford, making this a great location for commuters and those looking to enjoy all that Connecticut has to offer. Sold AS-IS

436 Main St, Portland

$549,900

4 Beds ⋅ 3 Baths ⋅ 24197375 MLS

ATTRACTIVE NEW PRICE! Bursting with style and character, this beautifully updated home seamlessly blends modern finishes with thoughtful design! Gather in the dramatic family room that is sure to wow you with its wood paneled soaring ceilings, oversized barn door and fireplace. Sliders let in the natural light and lead out to the charming covered porch. Anchored by a second, brick fireplace and built-in bar, the living room creates a second option for family time or socializing. Step out from the living room onto the luxurious, fully-covered deck. This inviting space expands the living room and is ideal for indoor-outdoor entertaining. Custom plantation-style shutters keep the space cool and offer weather protection. Large dining room features a chic light fixture and can seat a large number. A convenient sitting room creates a nice flow from dining to the family room and kitchen. Speaking of the kitchen, enjoy a beautifully remodeled space in sleek grays, complete with stainless steel appliances, venting chimney and granite countertops. Adjacent breakfast nook is great for a quick bite and also leads to the updated half bath. Upstairs, enjoy hardwood throughout! Primary bedroom has 3 closets and a fully remodeled bath boasting a tiled shower and modern fixtures. Three additional, well-sized bedrooms share a second, remodeled bath in trendy black and white. Laundry is currently housed in one of the upper walk-in closets for convenience.

15 Michele Dr, Portland

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