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25 Prospect St, Portland
$381,000
3 Beds ⋅ 2 Baths ⋅ 24201699 MLS
Highest and Best deadline is 12:00 on Tuesday, September 1. Home sweet home! This charming 3-bedroom Cape is nestled on a pretty, tree-lined lot and welcomes you from the moment you step inside. Warm and inviting, the home features beautiful hardwood floors and graceful rounded archways that add character throughout. Picture cozy evenings by the fireplace or relaxing on the patio in the warmer months. The sun-drenched sunroom, with its first-floor laundry, offers a versatile space that could also make a wonderful home office, reading nook, or sitting area. Upstairs, all three bedrooms are generously sized, and even the hallway offers more space than you typically find in a Cape, complete with a cedar closet. A one-car garage and full basement provide excellent storage, with the basement fireplace offering exciting potential for future finished living space. The current owner has made numerous improvements, including new windows and a new roof in 2025, along with a new dishwasher, washer and dryer, basement hatchway door, sunroom flooring, landscaping, and more! A true gem, this home has been lovingly maintained and thoughtfully improved, with an opportunity for its next owner to continue making it their own.

25 Prospect St, Portland

24 William St, Portland
$375,000
3 Beds ⋅ 2 Baths ⋅ 24143715 MLS
Fantastic Location! Whether you're just starting out or looking to downsize, this home is perfect for you! This charming 3-bedroom, 2-bath ranch is just minutes away from downtown. It features a recently remodeled kitchen with butcher block countertops, white cabinetry, and stainless steel appliances. The dining area includes a built-in corner cabinet and sliders that lead out to the deck. The formal living room boasts a stunning floor-to-ceiling fieldstone gas fireplace and beautiful hardwood flooring. Spacious Family Room with built-in features and a cozy gas fireplace, complemented by vaulted ceilings and wood laminate flooring. The lower level offers a finished space perfect for a workout room, multiple built-ins for extra storage, a laundry area, full bathroom and utility area. There's also a one-car garage which enters into the lower level making unloading your vehicle in inclement weather a breeze. See floor plan for additional storage area. Local highlights, Portland boasts several boat yards, golf course and driving ranges. Many restaurants and eateries offering delicious options. RT's 9,91 and Rt 2 are minutes away. Subject to seller finding acceptable housing.

24 William St, Portland

129 Summer St, Portland
$373,000
3 Beds ⋅ 2 Baths ⋅ 24165914 MLS
Inside this classic cape you'll find a cozy yet functional layout with sun-filled living spaces, hardwood floors, and a welcoming fireplace that serves as the heart of the home. The kitchen offers a perfect balance of vintage charm and modern convenience, with ample cabinetry. A convenient first-floor bedroom and full bath provide versatile options for guests, home office, or single-level living. Upstairs, you'll find additional bedrooms with additional storage and angled ceilings that add to the home's distinctive Cape appeal.The finished lower level expands your living space significantly, offering the perfect setup for a family room, media area, home gym, or playroom, along with additional half bathroom and storage. The breezeway should not be overlooked, as it provides a tranquil spot to soak in the sun and enjoy the seasons.

129 Summer St, Portland

2 Earle St, Portland
$370,000
3 Beds ⋅ 2 Baths ⋅ 24174874 MLS
Brand new to the Portland, CT market! Welcome home to 2 Earle Street, the charming ranch you have been waiting for! This home first and foremost is in the most idyllic location, tucked back on a quiet cul-de-sac, within walking distance of parks, plenty of businesses and restaurants. There is also very easy access to highways and obviously it is very centrally located. The home itself offers plenty of value with 3 bedrooms, 1.5 baths and over 1600 sqft of heated/cooled living space. There are hardwood floors, updated windows, mechanicals and 200 Amp electrical service. The basement offers a finished entertaining space along with storage/work spaces. The attic is a simple walkup and also can be utilized as storage, or potential for finishing it to add more sqft. Outside, the yard is very much flat and expansive with lovely trees and potential for a garden/patio space. Rounding it all out, the driveway is in great shape and there is a detached garage/shed building. 2 Earle is ready for new owners and a new story. All of this value is offered for $344,900! See it quickly!

2 Earle St, Portland

31 Grandview Ter, Portland
$370,000
2 Beds ⋅ 3 Baths ⋅ 24169264 MLS
Welcome home to this well-built brick ranch offering exceptional space, comfort, and flexibility, set on over an acre in the heart of Portland. With 1272 sq ft on the main level and an additional 897 sq ft of finished walkout lower-level space, this home is ideal for today's lifestyle and multi-generational living. Step inside to a spacious, light-filled living rm centered around a cozy fireplace, seamlessly connecting to the open dining area-perfect for both everyday living and entertaining. Large windows flood the home with natural light and nice hardwood floors. Freshly painted main level, adds warmth and character. The eat-in kitchen offers ample space and potential for updates, creating an opportunity to add your personal touch. The main floor features two generously sized bedrooms, including a primary suite with a full bath, along with a second bathroom with tub. The heated, finished walkout lower level expands your living space with a second fireplace, half bath and endless possibilities-ideal for a family room, home office, gym, or guest suite. Additional storage space adds to the home's functionality. Attached two-car garage offers convenience and ample storage. Recent updates include a brand new roof & gutters and repointed & rebuilt chimneys. Ideally located just minutes from Middletown and only 20 minutes to the CT shoreline. Don't miss this opportunity to create your dream home-schedule your showing today!

31 Grandview Ter, Portland

49 Copper Beech Ln Unit 49, Portland
$365,000
2 Beds ⋅ 2 Baths ⋅ 24173121 MLS ⋅ Copper Beech Village BLDG.
HIGHEST & BEST OFFERS BY 5/20/26 BY 6PM Beautifully maintained condo offering 2 bedrooms, 2 full baths, and 1,608 square feet of comfortable living space in a desirable Portland community. Surrounded by scenic views and professionally maintained grounds, this home combines low-maintenance living with a peaceful setting. The bright interior features hardwood flooring, an open-concept main living area, and abundant natural light throughout. The updated kitchen showcases stainless steel appliances, ample cabinetry, and clean modern finishes with an easy flow into the dining and living spaces. A main-level laundry area adds everyday convenience, while spacious bedrooms and well-appointed baths provide flexibility and comfort. The upper-level loft offers additional living space ideal for a home office, reading area, or guest retreat. Outdoor spaces include a welcoming front porch and private rear deck overlooking mature landscaping and wooded surroundings. Additional highlights include an attached garage, full basement, vinyl siding, and central air. Conveniently located near local shops, dining, commuter routes, and scenic river views, this condo offers a comfortable blend of space, functionality, and easy living.

49 Copper Beech Ln Unit 49, Portland

14 Church St, Portland
$365,000
2 Beds ⋅ 2 Baths ⋅ 24158206 MLS
Welcome to 14 Church Street - a picture-perfect bungalow that blends timeless charm with thoughtful modern updates. This move-in-ready home is filled with character, natural light, and beautiful custom details throughout. Hardwood floors lead you into a bright living space featuring a custom NORKO-built entry bench and cubbies, setting the tone for the craftsmanship found throughout the home. The dining area flows seamlessly into a beautifully renovated kitchen with granite countertops, white cabinetry, stainless steel appliances, a farmhouse sink, and tiled backsplash. The first floor offers flexible living with a guest bedroom, full bath, and a cozy sitting room or office complete with custom built-ins. Upstairs, the private primary suite feels like a retreat, featuring vaulted ceilings, built-in wardrobe storage, a convenient laundry area, and a spa-inspired bathroom with double vanity, soaking tub, and glass-tiled shower. Outside, enjoy a level backyard offering space to relax, garden, or entertain. A charming covered front porch provides the perfect place to start your morning or unwind at the end of the day. With an efficient heat pump system providing both heating and air conditioning, comfort comes year-round. Warm, inviting, and full of personality - 14 Church Street is the kind of home buyers fall in love with the moment they arrive.

14 Church St, Portland

5 Wellwyn Dr, Portland
$365,000
3 Beds ⋅ 1 Baths ⋅ 24145958 MLS
**Highest and Best Offers Due by End of Day Friday January 2nd** Set directly on the banks of the Connecticut River, 5 Wellwyn Drive in Portland offers a rare opportunity to own a truly special piece of waterfront land with breathtaking, unobstructed views up and down the river. From sunrise to sunset, the ever-changing scenery provides a front-row seat to one of Connecticut's most iconic waterways. Situated on 3.57 acres with direct river frontage, the property offers a setting that is both private and picturesque, making it an ideal canvas for those with vision. The existing home is in need of substantial renovation or replacement, presenting an exceptional opportunity for investors, builders, or buyers looking to create a custom riverfront retreat tailored to their tastes. This is an estate sale and is subject to probate approval. With its expansive acreage, unparalleled river views to the east and west, and irreplaceable waterfront location, this property represents a rare opportunity for something truly remarkable along the Connecticut River!

5 Wellwyn Dr, Portland

11 Lake Rd, Portland
$364,000
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

43 High St, Portland
$362,500
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 (2026) oil tank, (2025) furnace, (2025) water heater, roof. 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

5 Buttonhook Dr, Portland
$358,000
3 Beds ⋅ 1 Baths ⋅ 24145715 MLS
One floor living at its best especially in this price range and condition. This 3 Bedroom 1,440 sq ft ranch set in a desirable, scenic neighborhood offering flexible living. The spacious living room features a fireplace and bay window, creating a bright and welcoming space. A large eat-in kitchen offers ample room for everyday dining and entertaining. Three comfortable bedrooms feature hardwood floors and generous natural light. A finished, heated bonus room provides exceptional versatility and may serve as a family room, dining area, or study with hardwood floors, a bay window, and sliders opening to a spacious raised deck-ideal for relaxing or hosting guests. Enjoy a peaceful residential setting with easy access to shopping, dining, schools, parks, and major commuter routes. A walk-out basement and expanded driveway add everyday convenience, while the outdoor space offers both privacy and usability. A well-balanced home combining space, flexibility, and a location that makes daily living easy.

5 Buttonhook Dr, Portland

72 South Rd, Portland
$354,000
2 Beds ⋅ 3 Baths ⋅ 24110260 MLS
This isn't your cookie-cutter property-it's a one-of-a-kind opportunity offering space, flexibility, and a connection to nature. With 4 bedrooms, 2.5 bathrooms, and a layout designed for flexible living, this home is perfect for multigenerational households, in-law accommodations, or a home office setup. Two possible primary bedroom suites-one on each floor-provide versatility, while a separate studio space offers endless options for remote work, creative pursuits, or private retreat. Enjoy the peaceful setting with views of a nearby nature preserve and direct access to walking trails and state forest land. A walkout basement and abundant storage options-including a spacious basement, garage attic, three sheds, and a chicken coop-mean there's a place for everything. The heated 2-car garage adds comfort and functionality for parking, projects, or hobbies year-round. Set on open land with established gardens and a horse stable, this property invites a rural lifestyle with room to grow and explore.

72 South Rd, Portland

1 Foley Rd, Portland
$340,000
2 Beds ⋅ 1 Baths ⋅ 24167047 MLS
Charming one-floor living awaits in this cozy 2-bedroom, 1-bath ranch, perfectly situated in a quiet, friendly neighborhood. This well-maintained home offers a comfortable layout with thoughtful updates, including a brand-new roof, gutters & siding, a newer hot water heater(2020) and freshly painted bedrooms. Step inside to a spacious living room filled with natural light and beautiful hardwood floors. The eat-in kitchen exudes vintage charm, featuring a built-in hutch and views of the level backyard-perfect for everyday living and entertaining. A rear window awning helps keep the kitchen cool and comfortable during warmer months. Enjoy additional living space in the inviting three-season breezeway, an ideal spot to relax and take in the changing seasons. The home also includes a convenient one-car attached garage for parking and extra storage. The walk-up attic provides excellent storage with strong potential for second level expansion, while the unfinished lower level presents even more opportunity to create additional living space. Outside, the spacious yard is perfect for gatherings, gardening, play, or pets, with beautiful dogwoods and tulip trees adding seasonal color and charm. Ideally located on a corner beside the Town Hall field, this property offers both privacy and convenience, minutes from schools, the library, shopping, restaurants and golf courses.Whether you're a first-time buyer or looking to downsize this is the one! HIGHEST & BEST DUE BY 5/4 6:00p.m.

1 Foley Rd, Portland

40 Coe Ave, Portland
$330,000
2 Beds ⋅ 2 Baths ⋅ 24139162 MLS
Tucked away at the end of a cul-de-sac, this inviting home offers the perfect blend of comfort, charm, and potential. Enjoy true one-floor living with the flexibility to expand into the unfinished attic. Step inside through the enclosed porch, a versatile space that's perfect for storing coats and winter gear or transforming into a cozy indoor retreat filled with plants and natural light. The main level features an eat-in kitchen, a formal dining room, a spacious living room, two comfortable bedrooms, and a full bath - all exuding warmth and character. The lower level adds even more usable space, complete with two finished rooms (one featuring a bar for entertaining), a half bath, and a convenient walk-out to the backyard. Outside, you'll find a large, cleared yard - perfect for gatherings, gardening, or play - along with a handy storage shed. With its quiet location, generous yard, and future expansion potential, this home offers both charm and opportunity. Don't miss your chance to make it your own! Subject to probate court approval

40 Coe Ave, Portland

7 Sherwood Ct Unit 7, Portland
$324,000
2 Beds ⋅ 2 Baths ⋅ 24147583 MLS ⋅ Grandview Farms BLDG.
Welcome to this beautifully designed 2-bedroom, 2-bath home offering 1,097 square feet of comfortable, open-concept living in the desirable Grandview Farms 55+ community. The bright main level features a seamless flow between the living, dining, and kitchen areas with newer Pergo floors, along with convenient main-floor laundry. Relax in the sun-filled sunroom with lovely views, or step outside to enjoy the back deck-perfect for morning coffee or evening unwinding. This home also includes central air, solar panels for energy efficiency, a crawl space for additional storage, and a one-car garage with plenty of guest parking available. The unfinished second floor offers exciting potential for an additional bedroom, bathroom, or flexible living space. Enjoy a maintenance-free yard and the benefits of community living, including access to a clubhouse and nearby shopping, grocery stores, and easy access to Route 9. A wonderful opportunity to enjoy comfort, convenience, and low-maintenance living in a welcoming neighborhood.

7 Sherwood Ct Unit 7, Portland

1062 Portland Cobalt Rd, Portland
$309,900
2 Baths ⋅ 24116716 MLS
Discover a meticulously maintained and highly adaptable commercial property at 1062 Portland Cobalt Rd, offering 3,556 SF of flexible space ideal for a variety of professional uses. This building, constructed in 1949 and thoughtfully improved by the current owners, has seen numerous recent updates and is in excellent condition throughout. The property is currently configured as two distinct units, each with separate utilities, including central A/C. The right-hand unit is occupied by a skincare/wellness studio tenant who will be vacating prior to closing. The left-hand unit, with 5 separate working spaces, has been used as an office & workshop by the current owner. Whether you're a business owner looking to occupy one or both spaces, or an investor seeking to lease both units, this property offers outstanding flexibility to meet your goals. Set on 0.85 acres with 14 on-site surface parking spaces, the building is well-suited for a wide variety of uses, including professional offices, medical or wellness practices, creative or studio space, light retail, educational or training facilities, other commercial or service-oriented operations, & more. Its location on Route 66 ensures high visibility and convenient access for you & your clients. A truly versatile asset, this well-cared-for property offers endless potential & is ready for a new owner!

1062 Portland Cobalt Rd, Portland

242 Summer St Unit 242, Portland
$291,000
2 Beds ⋅ 3 Baths ⋅ 24157069 MLS ⋅ Summer Meadow BLDG.
Welcome to easy living in this beautifully updated condo perfectly situated near Portland Golf Course and the heart of downtown, where charming shops and inviting restaurants create a vibrant community atmosphere. With quick access to Route 9, commuting to work or heading to the beaches is effortless. Inside, the thoughtfully designed layout offers comfort and functionality. Both spacious bedrooms feature ample closet space and their own full en suite bathrooms - providing privacy and flexibility for owners and guests alike. The upper-level laundry adds everyday convenience and keeps living spaces organized and tidy. The main level has been tastefully refreshed with new luxury vinyl plank flooring, fresh paint, and an updated half bath. Sliding doors lead to a private balcony overlooking tranquil meadows - the perfect setting for morning coffee or unwinding at the end of the day. A one-car attached garage with an adjacent storage room completes the package, offering practicality without sacrificing style. This is low-maintenance living in a location that truly has it all.

242 Summer St Unit 242, Portland

45 Prospect St, Portland
$261,000
3 Beds ⋅ 2 Baths ⋅ 24125855 MLS
***H&B deadline for Tuesday 9/16 @ 5:00p.m*** Charming Historic Gem with Endless Potential - Nearly 200 Years Old! Step back in time with this captivating historic home, full of character and waiting for its next chapter. Nearly two centuries old, this property offers timeless charm alongside unique features like beautiful stained glass windows and a welcoming covered porch. Nestled in a quiet neighborhood, you'll enjoy peace and privacy with the convenience of being just minutes from downtown Middletown and the heart of Portland. The spacious yard is perfect for gardening, entertaining, or simply relaxing outdoors. This home is bursting with potential and ready for someone with vision-whether you're looking to restore its historic beauty or add your own modern touches. The previous owner had grand plans for this special place, and now it's your turn to bring them to life. A fantastic opportunity for renovators or old-home lovers Additional highlights include: Solar panels for energy efficiency Plenty of space both inside and out Prime location close to shops, restaurants, and more With a little TLC, this could be your dream home. Don't miss the chance to own a piece of history!

45 Prospect St, Portland

156 Summer St Unit 156, Portland
$240,000
2 Beds ⋅ 3 Baths ⋅ 24132479 MLS ⋅ Summer Meadow BLDG.
Welcome to Summer Meadow Condos! This half-duplex offers the perfect combination of comfort, convenience, and low-maintenance living. Step inside to an inviting open floor plan featuring a spacious living/dining area that flows seamlessly into a galley-style kitchen-perfect for both everyday living and entertaining. French doors off the living room fill the space with natural light and open to a private deck overlooking a serene, level backyard. Upstairs, you'll find two generously sized bedrooms, each with its own full bathroom, freshly painted walls, new carpeting, and the convenience of second-floor laundry. Additional highlights include a main-level half bath, propane heating, central air conditioning (new condenser in 2025 and heating system in 2022), and extremely low HOA fees of just $221/month. Enjoy the stress-free lifestyle of condo living with private parking and sidewalk-lined streets. Ideally located close to three golf courses, marinas, Brownstone Adventure Park, Portland Sports Complex, and the Airline Trail with easy access to Routes 2 & 9. Don't miss this town-house style home in Portland-schedule your showing today! Parking is on the right side of the driveway for this home.

156 Summer St Unit 156, Portland

3 Indian Hill Ave, Portland
$215,000
3 Beds ⋅ 2 Baths ⋅ 24133040 MLS
*A moment in time*. This is a very rare opportunity to own a piece of Portland History. The Job Bates Home was crafted in or around the year of 1747 and is available for the first time in 53 years. Located near the CT River this home is unique in so many ways. With original features such as wide plank flooring, not one but 2 beautiful original brownstone and fieldstone fireplaces, built in nooks and shelving, hand crafted doors and windows and original foundation that is still very much in tact. There have been some modern updates as well. Like the oiled fired furnace, updated electrical, generator panel and a partially finished addition that adds a bunch of first floor space. With 4 bedrooms and 2 full baths and over 1500 square feet, this property is looking for some renovations to bring it back to its glory. The opportunity to create something special is right here at 3 Indian Hill.

3 Indian Hill Ave, Portland

1 Brush Pasture Ln Unit 103, Portland
$195,000
2 Beds ⋅ 1 Baths ⋅ 24201610 MLS ⋅ Atrium Of Portland BLDG.
Welcome to The Atrium, a desirable 55+ community tucked into a lightly wooded, peaceful setting in historic Portland,former Brownstone capital of Connecticut. If you're looking to downsize without giving up comfort, convenience, or location, this affordably priced first-floor 2 bedroom condo is an opportunity worth seeing. Rarely available, this spacious two-bedroom unit offers easy single-level living with the added convenience of in-unit laundry and a secure building. Enjoy the tranquility of a country setting while being just minutes from the Connecticut River and the charming center of Portland, where quaint shops, local restaurants, and community charm await. Just across the river, neighboring Middletown expands your options with vibrant riverfront activities, festivals, shopping, entertainment, and a diverse selection of dining. The Atrium's central Connecticut location makes it easy to enjoy everything the area has to offer while providing a convenient commute to Hartford and surrounding communities. Whether you're ready to simplify, looking for a more manageable home, or simply want to enjoy the benefits of 55+ living, this rarely offered two-bedroom condo combines affordability, convenience, and a wonderful setting. Come discover why The Atrium could be the perfect place to call home!

1 Brush Pasture Ln Unit 103, Portland

1 Brush Pasture Ln Unit 205, Portland
$170,000
1 Beds ⋅ 1 Baths ⋅ 24171148 MLS
Welcome to The Atrium, Portland's sought-after 55+ active adult community offering comfort, convenience, and lifestyle all in one place. This affordable 1 bedroom, 1 bathroom Unit 205 features an efficient open layout with granite countertops, kitchen appliances included, spacious bedroom with large walk-in closet, and an updated accessible shower with grab bars. There is also space for a stackable washer and dryer in the unit. Enjoy secure fob entry, elevator access, private theater room, fitness center, library, and a spacious clubhouse with pool table and gathering space. Low-maintenance living with fantastic amenities at an attractive price point. A wonderful opportunity to enjoy easy living in the heart of Portland. Subject to probate approval.

1 Brush Pasture Ln Unit 205, Portland

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