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

$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

$389,000

3 Beds ⋅ 2 Baths ⋅ COMING SOON Status ⋅ 24194091 MLS

Welcome home to 13 Edwards! Nestled on a quiet cul-de-sac, this beautifully updated 3-bedroom, 1.5-bath home offers comfort, style, and easy living. From the moment you step inside, you'll be greeted by an open floor plan, gleaming hardwood floors, natural light, and beautiful finishes. The heart of the home is the updated kitchen, featuring quartz countertops, a spacious island with seating, and SS appliances. 3 comfortable bedrooms and a full bath are conveniently located down the hallway. The lower level offers additional living space with a welcoming family room, laundry room, and half bath. Additional highlights include a high-efficiency propane furnace, central A/C, a three-season porch, patio, oversized garage and an easy-to-maintain yard. With its thoughtful updates and inviting layout, this home is ready to welcome you!

13 Edwards Rd, Portland

$375,000

3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24193978 MLS

Beautifully Updated Home with Lake Access! Welcome to this move-in-ready 3-bedroom, 1-full-bath home in one of Portland's desirable lake communities. Thoughtfully remodeled throughout, this charming home features an updated kitchen and bath, modern finishes, and a bright, inviting floor plan designed for comfortable everyday living. A newer roof and active solar panels provide added value and energy efficiency. Outside, you'll find a spacious backyard that's perfect for entertaining or relaxing, complete with a patio and plenty of room for gardening, play, or pets. The attached garage offers convenience and additional storage. Enjoy the benefits of lake access for swimming, kayaking, fishing, or simply taking in the peaceful surroundings. Combining modern updates, outdoor living, and an exceptional location, this home is ready for its next owners. Don't miss this opportunity to enjoy all that Portland has to offer!

11 Lake Rd, Portland

$275,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193215 MLS ⋅ Summer Meadow BLDG.

Beautiful 2 Bedroom Duplex Condo, Open Floor Planwith Nice Hardwood Floors, Remodeled Kitchenwith Granite Countertops,Gorgeous Oak Cabinets with Wood Floors, 2 Upstairs Bedrooms each with their own Baths,Laundry Room is also Upstairs between the Bedrooms, Off Street Parking

152 Summer St Unit 152, Portland

$500,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192478 MLS ⋅ Bartlett Hill BLDG.

Location, Location, Location! Welcome to the sought-after 55+ community of Bartlett Hill! This move-in ready Berkshire style home offers 1,503 sq. ft. of comfortable living on a quiet cul-de-sac, backing to peaceful woods for exceptional privacy. An inviting front porch, beautifully landscaped gardens, and charming curb appeal welcome you home. Inside, the open floor plan is perfect for everyday living and entertaining. The first-floor primary suite features a walk-in closet and full bath with shower stall, providing the ease of one-level living. The kitchen flows into the dining area and cozy sunroom. The living room offers a direct-vent gas fireplace and convenient half bath. Hardwood floors enhance the entryway and kitchen.Enjoy your private rear deck overlooking the woods, perfect for relaxing and enjoying nature. Upstairs, you'll find a guest suite(perfect for live-in caregiver) with a full bath, generous closet space, and a versatile loft ideal for a home office, reading nook, or exercise area. The unfinished lower level provides abundant storage and future expansion potential, while the attached two-car garage adds convenience. Bartlett Hill offers beautifully maintained grounds, a welcoming atmosphere, clubs, social activities, pool exercise, scenic walking streets, strong association finances, and a low HOA fee. Conveniently located near golf, shopping, and dining, this home offers the perfect blend of privacy, low-maintenance living, and community. Schedule a tour

19 Plumrose Court Unit 19, Portland

$500,000

2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191576 MLS

19 Plumrose Court Unit 19, Portland

$420,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24185075 MLS

Talk about location! Tucked away in a quiet neighborhood, within walking distance to schools sits this lovely, well-maintained, one-owner ranch. Step inside and see the potential in this owner-built home offering one-level living, hardwood floors, a masonry fireplace with log bin, 2 full bathrooms, main-level laundry and 3 bedrooms with a walk-in closet in the master. You truly have all you need to make this home your own. In the clean, expansive basement you'll find plenty of space to utilize as you choose, including two finished rooms, a second fireplace, huge workbench, as well as the updated 200 AMP electrical, including a welder plug out to the garage - for those that like to tinker. Magic happens when you step out to the large, flat, private backyard where the opportunities are truly endless. Listen to the birds and enjoy the view of the abutting woods and natural ledge. Incredibly easy access to the Town Hall, Portland Library, Route 66, downtown Portland and Middletown. This home is special and ready for its next chapter!

3 Burr St, Portland

$449,000

8 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24186057 MLS

Exceptional investment opportunity in the heart of Portland! This well located two family property is generating impressive rental income that's offering immediate cash flow from day one. Conveniently situated just off Main Street and with quick access to major highways, the location is ideal for tenants and commuters alike. Close to shopping, restaurants, and local amenities, this income producing property is a fantastic addition to any investment portfolio. Whether you're expanding your holdings or purchasing your first multifamily property, this is an opportunity you won't want to miss.

12 Fairview St, Portland

$1,275,000

1 Baths ⋅ ACTIVE Status ⋅ 24185553 MLS

Three-building mixed-use income property on high-traffic Route 66 in Portland's prime B-2 commercial corridor. Currently occupied by two national tenants - Subway Restaurant (197 Marlborough) and State Farm Insurance (201 Marlborough, ground floor) - plus a residential dwelling (189 Marlborough) . All active leases are gross with tenants paying their own utilities, delivering a clean, low-expense income stream. Current NOI: $82,757 | Cap Rate: 6.9% at ask.

189-201 Marlborough St, 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

$299,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24182570 MLS

Investor's great opportunity!!!Must see this peaceful waterfront escape over looking Camp Ingersoll. This charming year-round home offers 2 bedrooms, 1 full bath, a cozy living room, and a kitchen overlooking the sparkling lake, creating the perfect setting to relax and unwind. Enjoy swimming, kayaking, and fishing right from your backyard while taking in the tranquil water views and natural surroundings. This home offer a New Roof, open floor plan, two bright bedrooms, and a yard that is ready to be turned into your Oasis. Whether you're looking for a weekend getaway or a full-time retreat, this magical property offers the perfect blend of comfort, serenity, and waterfront living. Come experience lake life at its finest and make this special retreat your home. Agents please look st agent remarks.

11 Jobs Gate, Portland

$99,900

ACTIVE Status ⋅ 24181559 MLS

One of the last lots available to build in this quaint neighborhood. Discover your perfect private escape on this nearly 2-acre approved building lot. Bordering a tranquil brook, this nature lover's paradise is just steps to the scenic Airline Trail for hiking and biking. Conveniently located just minutes from Route 66, providing easy access to local amenities, schools, and commuting routes. House and site plans available upon request. Agent is related to owner. Your peaceful sanctuary awaits!

Jobs Pond Road, Portland

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