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

$550,000

4 Beds ⋅ 3 Baths ⋅ 24194816 MLS

Welcome to this custom-built 4-bedroom, 2.5-bath Colonial, ideally situated on a beautiful corner lot! Offering timeless craftsmanship, spacious rooms, and endless potential, this well-maintained home is ready for its next chapter. Inside, you'll find hardwood floors, including all four bedrooms. The inviting front-to-back living room features a wood-burning fireplace, while the spacious family room offers a second fireplace and direct access to the rear deck-perfect for entertaining or relaxing. The eat-in kitchen includes solid wood cabinetry, a breakfast bar, and ample workspace. The primary suite features a private bath with a stall shower and dual closets. A generously sized secondary bedroom includes a dressing area and walk-up access to a large attic, providing exceptional storage or future expansion possibilities. The partially finished lower level with fireplace offers flexible space for a recreation room, home gym, or workshop. Currently used as an in-law area.The attached two-car garage is complemented by a detached two-car carriage house with electrical service and a storage loft-ideal for hobbyists, car enthusiasts, or additional storage (Built -1997). Outside, enjoy mature trees and perennial gardens creating a beautiful backyard retreat. Built by respected local builder Don Harmon, this quality home presents a rare opportunity to personalize a classic Colonial in an exceptional location! Newer heating system and well storage tank & generator hookup

39 Old Carriage Rd, Portland

$189,900

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 ⋅ 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

$499,000

3 Beds ⋅ 3 Baths ⋅ 24193593 MLS

A Stunning Colonial in an enchanting neighborhood of fine homes, tucked at the end of a quiet cul de sac. This 3 bedroom 2.5 bath home may just be the one you've been waiting to call HOME. Drive up the tree lined driveway - over the belgian blocks and crushed stone, up to the 2 car garage. Walk the front walkway to the classic New England facade and enter into the 2 story foyer. Formal living and dining rooms flank the entry; a powder room is discreetly tucked in the hall. An open eat-in kitchen / family room span the width of the home with stainless steel appliances and granite - with a slider out to the deck and very private yards. Upstairs, there is a primary suite large enough for your king bed, with a walk in closet and owner's bathroom. There are currently two spacious guest rooms and a full bath - but just down the hall is a large unfinished space waiting to be whatever your heart desires - it could be a 4th bedroom as the septic is sized for 4 bedrooms. There is plenty of storage in the garage and the basement. What's more, the ROOF is BRAND NEW! Meticulously maintained and loved - this single owner home is ready for it's new inhabitants. There is an alarm system for peace of mind; a large flat yard in front and the side; a sizable deck for entertaining AND best of all for our hot summer days - CENTRAL AIR. Come and see this bucolic residence, and fall in love.

34 Fox Run Rd, Portland

$375,000

3 Beds ⋅ 1 Baths ⋅ 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 ⋅ 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 ⋅ 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 ⋅ 24191576 MLS

19 Plumrose Court Unit 19, Portland

$499,900

9 Beds ⋅ 4 Baths ⋅ 24182877 MLS

Investor alert in the heart of Portland! Welcome to 354-356 Main Street, a rare 4-unit multifamily offering incredible upside, strong rental potential, and a layout that works beautifully for both investors and owner-occupants. Priced with condition in mind, property is being sold as-is. Two units are currently month-to-month and well below market rent, creating a major value-add opportunity from day one. Projected rents offer impressive income potential, with units estimated around $1,600/month, the spacious townhouse-style unit around $2,000/month, and the 3-bedroom unit around $1,800/month. This property also features a huge backyard, offering outdoor space rarely found with multifamily properties. Whether tenants want room to relax, garden, grill, or enjoy extra green space, this yard adds major appeal. Need storage, workspace, or a place to bring your hobbies to life? The detached garage needs work, but with the right handy buyer, it could be transformed into an amazing workshop, storage space, or dream setup for mechanics, gearheads, contractors, or anyone needing extra room. Major Bonus: The oil furnaces were replaced aproximatley 4 years ago. Perfect for investors looking to increase rents and build long-term cash flow, or an owner-occupant looking to live in one unit while the others help pay the mortgage. OPEN HOUSE SAT/SUN 1-3PM You will be able to get into ALL 4 units and basement

356 Main St, Portland

$389,000

4 Beds ⋅ 2 Baths ⋅ 24189489 MLS

*** Highest and Best Tomorrow 7.15.26 by Noon*** Welcome to 564 Main St. Portland. This is the one you%27ve been waiting for! Brimming with Charm and Character, a spacious Eat In Kitchen and an Oversized Two Car Garage with electricity for Enthusiasts. This Well Built Quintessential Cape offers 4 bedrooms with a Main floor Primary loacated off the Living room for Privacy, or an In-Law situation, while the half bath is Conveniently located off the kitchen. A Full Dining room gives extra options for space, including a three season sunroom with a heater that stays. Hardwood Flooring throughout including under the brand new carpets. Upstairs you%27ll find three bedrooms and a full bathroom. Other Features include a Newer Furnace, Newer windows, Newer roof on home, Fridge approx. 2Y old, Dishwasher 6Y old, New Shed in 2020, and a clean unfinished basement with Tall ceilings giving an abundance of storage. Natural gas and public utilities complete your worry free living. Set on almost an acre, this Lush Private flat level yard is perfect for Sports, Entertaining Huge Outdoor bashes, or just relaxing in your private Oasis among tall trees including a historic Holly bush. Portland is home to many golf courses, The Ct River for Boating enthusiasts, and Minutes away from Downtown Middletown restaurants and shopping, yet quietly tucked away for the best of both worlds. Come see What this hometown has to offer!

564 Main St, Portland

$399,000

3 Beds ⋅ 3 Baths ⋅ 24184434 MLS

Nestled along a picturesque country road, this well-maintained home offers the perfect balance of privacy, comfort, and convenience. The flexible floor plan features a first-floor office/library, ideal for remote work or a quiet reading retreat, along with a spacious second-floor loft/family room that provides additional living space for relaxing, entertaining, or hobbies. Downstairs you will find a finished lower level with a sliding door walk out to the spacious yard. Six-panel doors add timeless character throughout the home, while mini-split systems provide efficient cooling. The maintenance-free exterior allows for easy upkeep, and the location offers a peaceful setting just minutes from Route 17, shopping, dining, and commuter routes. Move-in ready and lovingly cared for, this is a wonderful opportunity to enjoy country living with modern comforts.

48 Old Marlborough Tpke, Portland

$449,000

8 Beds ⋅ 6 Baths ⋅ 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

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