Portland Real Estate

Welcome to the charming city of Portland, Connecticut, a hidden gem nestled in Middlesex County. Known for its picturesque landscapes and rich history, Portland offers a delightful blend of small-town charm and modern conveniences. Situated along the scenic Connecticut River, this vibrant community is perfect for those who appreciate natural beauty and a relaxed lifestyle.

Portland is steeped in history, with its roots dating back to the 17th century. The town features beautifully preserved historic architecture, including the iconic Brownstone Quarries, which contributed to the city’s development and offers a glimpse into its industrious past. Outdoor enthusiasts will find plenty to love here, with numerous parks, hiking trails, and access to the river for kayaking and fishing.

The downtown area is bustling with local shops, cozy cafes, and artisanal eateries, making it a perfect spot for a leisurely afternoon. Residents enjoy a strong sense of community, with numerous events and festivals held throughout the year, fostering connections among neighbors and celebrating the town’s unique culture.

Families will appreciate the highly-rated schools and the safe, welcoming environment that Portland provides. With easy access to major highways and nearby cities like Middletown and Hartford, commuting is a breeze, allowing residents to enjoy the tranquility of suburban life while still being close to urban amenities.

Whether you’re looking to settle down, raise a family, or simply enjoy a peaceful retreat, Portland, CT, has something for everyone. Discover the charm of this lovely town and make it your new home today!

Newest Listings in Portland

$495,000

3 Beds ⋅ 2 Baths ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 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

$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! Multiple Offers Received - Highest & Best Requested By Wednesday 9/9 @10:00 AM

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

$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

$425,000

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.Property back on the market due to seller not receiving the EMD.No inspections performed.

64 Jobs Gate, Portland

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