Portland Real Estate

Welcome to Portland, Connecticut—an enchanting riverside town nestled in the heart of Middlesex County. With its picturesque landscapes and rich historical charm, Portland offers a unique blend of small-town warmth and modern convenience, making it an ideal place to call home.

Situated along the banks of the Connecticut River, Portland boasts stunning views and abundant outdoor recreational opportunities. Residents enjoy access to beautiful parks, hiking trails, and the scenic beauty of the riverfront. Whether it’s a leisurely stroll through the lush greenery of Brownstone Park or a thrilling day of kayaking on the river, Portland is a haven for nature lovers and outdoor enthusiasts alike.

The town is steeped in history, with charming architecture and a vibrant downtown area that showcases local boutiques, cafes, and restaurants. Portland’s commitment to community is evident in its numerous events and festivals throughout the year, fostering a strong sense of belonging among residents. The Portland Fair, held annually, is a beloved tradition that brings together families and friends for fun, food, and entertainment.

Education is a priority in Portland, with top-rated schools that provide a nurturing environment for children. The town's close-knit community ensures that families have access to the resources and support they need to thrive.

With its perfect blend of natural beauty, rich history, and a welcoming community, Portland, CT is more than just a place to live—it's a place to flourish. Discover your dream home in this charming town, where every day feels like a delightful escape.

Newest Listings in Portland

$495,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24200193 MLS

This gracious Portland home offers nearly 2000 square feet of character, comfort, and wonderfully livable space in a desirable neighborhood. With three bedrooms and two and a half baths, the home retains the warmth and craftsmanship of an earlier era while offering the conveniences expected for modern living, including central air, public utilities, and an attached two car garage.Hardwood floors run throughout the home, complemented by exposed wood beams, handsome millwork, and inviting rooms with a sense of history and permanence. The generously sized kitchen offers abundant cabinetry, substantial counter space, stainless steel appliances, and expansive windows overlooking the property. Adjoining living spaces are equally welcoming, with warm architectural details and a fireplace that gives the home an unmistakable sense of character.The sunroom is a particularly appealing retreat, surrounded by windows and overlooking the yard. It is an ideal setting for morning coffee, a quiet afternoon with a book, or relaxed evenings enjoying the changing seasons. Upstairs, three comfortable bedrooms provide private quarters, while a walk up attic offers excellent additional storage and the practicality so often missing from homes of this vintage.Outside, the well maintained yard is framed by mature plantings and generous lawn, offering plenty of space for gardening, entertaining, recreation, or simply enjoying the outdoors. The two car garage and additional storage make everyday living

8 Robert St, Portland

$550,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24205785 MLS

Set on a beautifully landscaped .57-acre lot, 15 Payne Boulevard is a distinctive 3-bedroom Colonial offering possible 4th-bedroom flexibility and finished space across four levels. Hardwood floors lead through the main level, where a wood-burning fireplace anchors the living room and the formal dining room, eat-in kitchen, renovated half bath, first-floor laundry, and private office create a layout that works as beautifully as it lives. Upstairs, three spacious bedrooms and two full baths provide comfortable separation, while the finished walk-up third floor offers an exceptional setting for a potential fourth bedroom, studio, playroom, or second office. The finished walkout lower level adds another dimension with a generous recreation room, gym, and space for guests or hobbies. Outside, the deck overlooks a private backyard with established gardens, a basketball court, greenhouse, and versatile three-part shed. The rare heated three-car garage features tall ceilings, exceptional workspace, and additional storage beneath the third bay. A new central-air system and air handler serving the upper level add modern comfort. Near local farm stands, Arrigoni Winery, the Connecticut River, Brownstone Adventure Park, Portland's town center, and Middletown-this is where space, character, and possibility come together.

15 Payne Blvd, Portland

$345,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24031325 MLS

HIGHEST AND BEST BY TUESDAY 9/15/2026 8PM! A little cottage with a lot to love! This charming Cape Cod sits on a picturesque corner lot in the heart of Portland, offering beautiful curb appeal and a welcoming setting. The main level features two separate living areas filled with natural light, including one with a cozy fireplace and built-in bookshelves that create a warm and inviting space full of character. A dining room with a built-in hutch, a kitchen with granite countertops, and half bath complete the main level. Upstairs, three bedrooms offer flexibility for family, guests, or a home office. Step outside and enjoy the home's special outdoor spaces, including a charming wooden pergola, established gardens, stone landscaping, and a spacious yard with plenty of room for gardening, entertaining, or simply enjoying the outdoors. And the location is hard to beat! The home is within walking distance of Portland's downtown village, Riverfront Park, and the local library. Enjoy spectacular fireworks views from the historic Arrigoni Bridge, and when you're ready for even more dining, entertainment, and things to do, Middletown's ever-growing culinary and entertainment scene is just a five-minute drive away! All while still coming home to the quiet residential setting of Fairview Street.

40 Fairview St, Portland

$365,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201424 MLS

Welcome to this well-cared-for Cape-style home in a convenient Portland location! This inviting 3-bedroom, 1.5-bath home offers charm, comfort, and many updates. The main level features a spacious living room with fireplace, a first-floor bedroom currently being used as an office, a beautifully remodeled eat-in kitchen with plenty of cabinetry, and a formal dining room perfect for family meals or entertaining. Upstairs are two additional bedrooms. The finished lower level provides additional living space for a family room, recreation area, or hobbies. Outside, enjoy a nice lot with a private pool, offering a wonderful space to relax and entertain. Meticulously maintained and exceptionally clean, this home has been well cared for, with several important major components updated, including a newer oil tank, furnace, roof, and water heater. These improvements provide valuable peace of mind for the next owner. A wonderful opportunity to own a home with many of the big-ticket items already addressed, while still offering the opportunity to make it your own. Conveniently located near schools, shopping, restaurants, recreation, and major routes.

43 High St, Portland

$339,900

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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

$999,900

2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$690,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24196429 MLS

Custom-built by renowned local builder McGinley, this exceptional home is tucked away at the end of a peaceful private road, in the desirable The Highlands subdivision, privately situated on 3.34 acres. Thoughtfully designed and built as the builder's own residence, this spacious home offers quality craftsmanship, character, and incredible versatility throughout. A grand foyer welcomes you into the impressive front-to-back living room featuring an oversized fireplace with a stately mantle, ceilings with exposed beams and a sunken area with a slider that leads you out to a private deck creating warm inviting spaces perfect for gathering. The expansive kitchen offers abundant cabinetry, custom wood block island, pantry, hardwood floors, and a cozy seating nook overlooking the backyard. Formal dining room , mudroom and laundry area conveniently located off the kitchen. Elegant crown molding and hardwood throughout the home.The upper level offers 3 bedrooms and 2 full baths with a spacious primary suite with a walk-in closet and full bath.The finished walk-out lower level provides excellent in-law potential with an additional bedroom, kitchen, bathroom, and flexible living space. Enjoy the outdoors from the wraparound deck overlooking the tranquil, private backyard setting.

68 High St, Portland

$189,900

ACTIVE Status ⋅ 24194308 MLS

Absolutely top-tier parcel of Land offering over 12 acres of exceptional privacy, natural beauty, and serene surroundings. Accessed at the top of your very own private road (Molly Lane), this remarkable lot sits high with lots of potential with many level areas to build- ideal for creating a truly special custom estate. This is not an ordinary piece of land; it represents a rare opportunity to build in a peaceful, nature filled setting while still enjoying the convenience of a suburban location. A one-of-a-kind offering for those seeking true privacy and absolutely beautiful surroundings.

184 Cox Rd, Portland

$499,900

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24183461 MLS

Set on a generous 1.2-acre lot in Portland, this expansive ranch offers an incredible amount of space and potential for someone ready to bring their vision to life. With over 4,300 square feet of living space, the home features 10 rooms including 4 bedrooms and 3 full baths plus a half bath, providing plenty of room for extended living, hobbies, or multi-generational needs. The layout offers the convenience of single-level living with large rooms and a full basement below for additional storage or future finishing. Built in 1995, the home includes an attached garage, deck and open porch areas, and sits well back from the road with a wide driveway and spacious yard. While the property does need updating and repairs, the size, layout, and setting create a rare opportunity to transform a large ranch into something truly special. With some work and imagination, this could become an exceptional long-term home in a quiet Portland setting.

57 Summer St, Portland

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