Portland Homes for Sale

Welcome to Portland, Connecticut – a charming riverside town nestled in Middlesex County, where small-town charm meets modern convenience. Known for its picturesque landscapes and vibrant community, Portland offers a unique blend of natural beauty and rich history. With the Connecticut River winding its way through the town, residents enjoy stunning views and ample opportunities for outdoor recreation, including hiking, boating, and fishing.

Portland’s historic downtown area is a delightful mix of quaint shops, local eateries, and cultural landmarks, making it a perfect place for families and individuals alike. The town is also home to several parks and recreational facilities, ensuring that there’s always something to do, whether it’s enjoying a picnic in the park or participating in community events throughout the year.

For those considering a move to this idyllic town, there are a variety of homes for sale that cater to diverse lifestyles and budgets. From charming single-family homes with character to modern townhouses with contemporary amenities, Portland’s real estate market has something for everyone. Whether you’re a first-time homebuyer or looking to settle into a larger family home, you’ll find properties that fit your needs perfectly.

With its friendly atmosphere, excellent schools, and close-knit community, Portland is more than just a place to live – it’s a place to thrive. Explore the homes for sale in this beautiful town and discover the perfect spot to create lasting memories. Welcome to Portland, where your dream home awaits!

Newest Portland Homes for Sale

$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

$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

$500,000

2 Beds ⋅ 3 Baths ⋅ 24191576 MLS

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

$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

$499,900

4 Beds ⋅ 4 Baths ⋅ 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 ⋅ 24182570 MLS

Must see this beautiful peaceful waterfront home. 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, new water system, 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 retreated, 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

$638,000

4 Beds ⋅ 3 Baths ⋅ 24177582 MLS

Tucked at the end of a quiet cul-de-sac on nearly 3 private acres, this meticulously maintained home is truly turn-key, and it shows in every detail. A brand new roof and brand new hardwood floors throughout the entire home completed in spring of 2026 give the home a pristine, like-new feel. The main level flows beautifully from a sun-filled kitchen with stainless steel appliances, granite countertops and a center island into an inviting living room with a woodburning fireplace, formal dining room, and dedicated home office. Upstairs, four spacious bedrooms include a primary suite with two closets, featuring a walk-in. The oversized fourth bedroom offers exceptional flexibility as a playroom, media room, or additional living space with a partial walk-in closet. The outdoor living is truly exceptional with lush, lovingly maintained gardens and both front and back decks that make it easy to enjoy every season in this peaceful setting. Private, thoughtfully updated, and truly move-in ready, this is a home that feels special the moment you arrive and is made for making memories.

31 Fox Run Rd, Portland

$699,000

3 Beds ⋅ 4 Baths ⋅ 24176313 MLS

Surrounded on three sides by the 90-acre Palmer-Taylor Preserve, this one-of-a-kind home offers an extraordinary combination of history, privacy, and natural beauty. Originally built in 1979 and thoughtfully expanded over the years, the residence incorporates an early 20th-century guesthouse once associated with the Taylor family of nearby St. Clements Castle, creating a home unlike any other. The setting is truly special, with permanently protected conservation land providing exceptional privacy, direct access to walking trails, abundant wildlife, and peaceful views in every season. A nearby stream, bluestone terrace, bocce court, fire pit, and beautifully landscaped grounds create inviting outdoor spaces for relaxing and entertaining. Inside, the flexible floor plan offers multiple living areas, a spacious primary suite with loft, and a finished walkout lower level with a full bath. Recent improvements include updated windows, central air conditioning, a high-efficiency natural gas boiler installed in 2024, and rare underground natural gas service. The existing carport was designed with future expansion in mind and is engineered for conversion to an enclosed garage, with the potential to add a second-story space above. Additional features include a backup generator system, security system, and mature landscaping designed to provide year-round beauty. A remarkable opportunity to own a home where history, architecture, and nature come together.

235 Middle Haddam Rd, Portland

$499,000

4 Beds ⋅ 2 Baths ⋅ 24173238 MLS

Welcome to a beautifully updated 4-bedroom, 1.5-bath colonial in the heart of Portland, featuring a new roof and chimney, remodeled kitchen and full bath, newer vinyl replacement windows, updated electrical, new water heater, extended and replaced driveway, updated masonry, and numerous thoughtful modern upgrades throughout. This home offers is move-in ready with timeless character and charm. Inside, the recently remodeled kitchen features updated finishes, a new range hood with exterior venting, and abundant natural light throughout the main living spaces. Unique custom details crafted from reclaimed wood sourced directly from the home add warmth and character, including built-in bookshelves, radiator covers, a custom TV stand, and a built-in bench. The upstairs full bathroom has been fully remodeled, while the lower-level bath features updated flooring. Additional improvements include a new washer and dryer, smart locks, an independent Hydroviv water and ice filter for the fridge, fiber internet, and a basement dehumidifier for added comfort. Exterior updates include new front and back stairs, front walkway, patio, and retaining wall. The yard has also been professionally maintained. Ideally situated near downtown Portland, South Glastonbury, Brownstone Exploration Park, the Connecticut River, local restaurants, shopping, Middletown, and Route 9, this home offers a wonderful blend of updates, character, and convenient access to surrounding destinations!

575 Main St, Portland

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