Portland Homes for Sale

**Discover the Charm of Portland, Connecticut**

Nestled along the scenic banks of the Connecticut River, Portland is a hidden gem in Middlesex County that boasts a perfect blend of natural beauty, rich history, and vibrant community life. This picturesque town is renowned for its stunning landscapes, including the stunning views from the Portland Riverfront Park, which invites residents and visitors alike to explore its walking trails, picnic areas, and serene waterfront.

Portland is steeped in history, with its roots tracing back to the 17th century. The town is home to several historical landmarks, such as the iconic Brownstone Quarries, which played a significant role in the region’s development. With a strong sense of community and a commitment to preserving its heritage, Portland offers a welcoming atmosphere that makes it easy to feel at home.

For those looking to settle in this charming town, there are a variety of homes for sale that cater to diverse tastes and lifestyles. From cozy single-family homes with spacious yards to modern townhouses with contemporary amenities, Portland’s real estate market has something for everyone. The homes here are often characterized by their unique architectural styles, many featuring beautiful gardens and stunning views of the surrounding natural landscape.

With excellent schools, local parks, and a thriving arts scene, Portland is an ideal place for families, young professionals, and retirees alike. Explore the homes for sale in Portland, Connecticut, and discover the perfect place to create lasting memories in this enchanting riverside town. Embrace the lifestyle that awaits you in Portland, where community spirit and natural beauty come together seamlessly!

Newest Portland Homes for Sale

$270,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24200720 MLS

This 3 bedroom, 1.5 bathroom Colonial style property has a living room with a fireplace and a sunroom. The interior has hardwood floors. The dining area sits within the main living space, so meals and gatherings share one open area. The sunroom adds a separate room beside the main rooms. The lot measures.39 acre, which gives the property outdoor space around the building. Schedule a showing to see the layout in person and look over each room. This is a Fannie Mae HomePath property. The Seller must comply with HUD Guidelines 24 CFR 206.125.

25 Spring St, Portland

$525,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24212735 MLS

Highest & Best by 10/29 at noon! Spacious Colonial living with privacy, poolside relaxation & room to entertain! This spacious 4-bedroom, 2.5-bath Colonial offers the perfect blend of privacy, neighborhood charm and versatile living space. Step inside to a welcoming foyer and discover a thoughtfully designed first floor featuring a generous living room, formal dining room, remodeled eat-in kitchen w. Corian countertops and a comfortable family room with pellet stove. A convenient half bath and first-floor laundry add to the home's everyday functionality, while the flexible layout provides plenty of space for entertaining, gathering or simply enjoying life at home. Step out the back door and discover your own outdoor retreat! Plenty of room to relax, entertain, and enjoy the seasons, with an inviting 20 x 40 inground pool ready for summer days, multiple decks- perfect for outdoor dining and gatherings and nice level yard with fenced in back yard and large shed. Upstairs, you'll find three additional bedrooms, a full bathroom, and a spacious freshly painted primary suite featuring a walk-in closet and private updated full bath. A walk-up attic and full basement provide abundant storage and additional possibilities, while the attached two-car garage offers everyday convenience. With generous living space, a pellet insert, an inground pool, and a desirable cul-de-sac street on the Glastonbury town line, this home offers endless opportunities to make it your own. New Roof - 2025

18 Michele Dr, Portland

$580,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24210575 MLS

BREATHTAKING 30+ MILE VIEWS & VERSATILE LIVING! Perched atop a scenic hill, this distinctive property offers panoramic views and a setting that celebrates the beauty of its natural surroundings. The inviting open-concept design is filled with natural light, creating a wonderful flow for everyday living and entertaining. The main level features a spacious foyer, primary bedroom w/ remodeled bath (2020) and walk-in closet, two additional bedrooms, 1 1/2 baths, convenient laundry, and a family room ideal for a home office or flexible living space. The kitchen (2021), dining area, and living room with pellet stove provide a welcoming gathering space, while an open staircase leads to two additional rooms upstairs offering even more possibilities. A standout feature is the private-entry in-law apartment, complete with two rooms, a full bath, and kitchenette-ideal for extended family or flexible living arrangements. The lower level also offers a spacious two-car garage, workbench, and utility rooms. Outdoors, enjoy relaxing on the decks, taking in the incredible views, or unwinding to the soothing sounds of the backyard waterfall. Red quarry stone adds character to the outdoor setting, while the thoughtfully landscaped front yard features low-maintenance plantings and organic apple, pear & peach trees to enjoy seasonally. If you're looking for remarkable views, adaptable living space and a property w/ distinctive character, this unique home is an opportunity you won't want to miss!

Portland

$539,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214680 MLS

This charming Classic Raised Ranch is nestled in the heart of Portland, offering a perfect blend of comfort and convenience. The main level features an inviting eat-in kitchen that seamlessly connects to a formal dining room, perfect for family gatherings or entertaining guests. The spacious living room is highlighted by a cozy wood fireplace and a picturesque bay window, creating a warm and welcoming atmosphere. With four bedrooms on the main level and an additional fifth bedroom on the lower level, there's ample space for family and guests. The lower level also boasts a den with another fireplace, an office, and a full bath, providing versatile living options. Car enthusiasts will appreciate the four garages, offering plenty of room for vehicles and storage. Portland offers a wealth of recreational opportunities, including three nearby golf courses, a newly developed town park with sports fields and tracks, and the Oakwood Soccer Club's field. Additionally, the Brownstone Quarry Park is just a short distance away, providing even more outdoor adventures. This property truly offers a wonderful lifestyle in a vibrant community.

726 William St Ext, Portland

$460,000

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24212475 MLS

Pride of ownership shines throughout this cherished home, lovingly cared for by its original owners who built a home filled with love, laughter, family and treasured memories. Designed for both everyday living and entertaining, this home has been the backdrop for years of gatherings, celebrations and countless special moments. Hardwood floors flow throughout the main living spaces. The open kitchen and dining area are ideal for gathering, while the large living room with fireplace offers a warm and inviting place to relax. Beautiful bay windows fill the home with natural light. The main level features convenient laundry and remodeled baths, including one with a walk-in shower. A side entrance with paver walkway leads to an oversized mudroom conveniently connected to the kitchen. The finished partial basement offers additional entertaining space with a fireplace and bar area, or the opportunity to create a space of your own. Outside, enjoy a lush, private setting with mature trees behind the property. The in-ground pool became a favorite gathering place for family and friends, creating countless summer memories. For decades, this has been a place where family and friends gathered, celebrations were shared, and memories were made. Now, the opportunity is here for someone new to enjoy all this home has to offer and create their own special memories.

132 Pepperidge Rd, Portland

$450,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 24198961 MLS

For the boat lover and the visionary, this property may be that diamond in the rough you have been waiting for! Located at 164 Airline Avenue in Portland, CT, it is listed for only $250,000. The taxes are low ($3086) so this is very affordable! It offers plenty of space (1,326 square feet) so you can occupy as you renovate - slowly if you need to. It sits on 0.34 acres with a private backyard and has 3 bedrooms that includes an additional open space in the primary bedroom that could be turned into another small room/huge walk-in closet/nursery/office/small gym - the possibilities are endless! But the best part of this home is that it is walking distance to 2 boat marinas and a brand new boat landing! River Bend Landing is a brand new FREE access point to the Connecticut River. If you enjoy fishing, kayaking, canoeing or rafting, this landing is practically in your backyard (it's more like right across the street)! Birdon Marina is a 16 minute walk and the Members-Only Meriden Motor Boat Club is only 1 minute away! I have attached photos as well as the listing link for your view. Please let me know if you have any questions or if you would like to take a look! The property was bought with the intention to renovate and work was started (the half bath on the main level started to put in a shower to make another full bathroom and the furnace was completely replaced with new piping). All this home needs is your magic touch!

164 Airline Ave, 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

$149,000

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24163884 MLS

WATERFRONT ! Enjoy This Cozy WATERFRONT Home located in Portland, CT. Grab your Coffee every morning and Walk down and Jump right in the Water! Don't miss enjoying this summer 2026 & the summers to come, Family Fun in this Home on Jobs Pond ! This Home has full views overlooking THE WATER! This Home offers a Living room with views overlooking the Water, open Kitchen & Dining area, Bedroom, newer Full bath. Walkout Basement for storage to a Large open deck for entertaining. Walk down to the water for swimming and boating, Private Dock, includes Paddleboat & row Boat. This is a Full Year Round House if a well is installed, the water is pumped from the pond. IMPROVEMENTS INCLUDE:Newer roof, Windows and decking down side of house to newer back Deck. Appliances include:Refrigerator, Propane Cooktop.

52 Jobs Gate, Portland

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Portland Homes for Sale

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