Portland Homes for Sale

Welcome to the charming city of Portland, Connecticut, a hidden gem nestled in the picturesque Middlesex County. Known for its rich history and stunning natural landscapes, Portland offers a unique blend of small-town charm and modern convenience. With the Connecticut River gracefully winding through the area, residents enjoy breathtaking views and a plethora of outdoor activities, from hiking and biking to boating and fishing.

Portland is not just about natural beauty; it boasts a vibrant community spirit, with local shops, cozy cafes, and delightful eateries that make every day feel special. The town hosts various events throughout the year, fostering a strong sense of belonging among its residents. Families are drawn to Portland for its excellent schools, safe neighborhoods, and a welcoming atmosphere that makes it easy to connect with neighbors and friends.

For those considering a move to this idyllic location, there are a variety of homes for sale that cater to diverse lifestyles and preferences. Whether you’re looking for a charming historic home with character, a modern townhouse with contemporary amenities, or a sprawling property with room to grow, Portland has something for everyone. With competitive pricing and a range of options, now is the perfect time to explore the real estate market and find your dream home in this enchanting city.

Discover the magic of Portland, CT, where community, nature, and opportunity come together to create a truly special place to call home. Start your journey today and see why so many are choosing to make Portland their forever home!

Newest Portland Homes for Sale

$374,900

4 Beds ⋅ 3 Baths ⋅ 24219364 MLS

Welcome home to Portland! OH Sunday Nov 8 from 12:00 to 1:30PM. This mechanically updated 4-bed, 2.5-bath one-level Ranch balances modern ease with convenience. Major updates like roof, furnace, water, and AC have all been updated in recent years providing a foundation for your cosmetic touches. The living room opens to a 3 season porch and over half an acre to entertain and enjoy the outdoors. Minutes from Middletown's dining easy access to highways, enjoy effortless single-story living. The outdoor oasis features a lighted firepit and wiring for a future pool, while the massive full basement offers endless possibilities. Enjoy a premier riverfront lifestyle with 8 marinas, 3 golf courses, and top schools nearby. This community-centered home is the ultimate CT retreat!

25 Brooks Ln, Portland

$499,900

4 Beds ⋅ 3 Baths ⋅ 24218403 MLS

Welcome to 36 Michele Drive, where classic Colonial charm, thoughtful updates, and room to spread out come together! Tucked into an established Portland neighborhood, this well-maintained 4-bedroom, 2.5-bath home offers 1,989 square feet of living space on a beautiful, level one-acre lot. Step inside to discover an open floor plan with multiple gathering spaces, including a spacious living room, dining room, and comfortable family room with a fireplace. The updated eat-in kitchen features granite countertops, stainless steel appliances, ample cabinetry, and room for casual dining. Hardwood flooring throughout much of the home, including new floors installed in 2023, adds warmth and character. Updated lighting and ceiling fans (2023), new first-floor baseboards (2025), and convenient main-level laundry are additional highlights. Upstairs, you'll find four generously sized bedrooms, including a primary suite with its own private full bath, plus a second full bathroom. Outside, enjoy a spacious deck overlooking the level backyard, offering plenty of room for outdoor entertaining, gardening, or simply relaxing. With a new roof in 2018, solar panels installed in 2024 (financed), generator hook-up and numerous additional improvements, this home offers the space, flexibility, and updates today's buyers appreciate!

36 Michele Dr, Portland

$270,000

3 Beds ⋅ 2 Baths ⋅ 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 ⋅ 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

$415,000

3 Beds ⋅ 3 Baths ⋅ 24215838 MLS

Tucked away at the end of a quiet cul-de-sac, 11 Hale Road offers the perfect combination of privacy and a neighborhood feel. This 3-bedroom, 1,812 sqft home (with an additional 576 sqft finished and heated on the lower level) features original hardwood floors, newer windows throughout, custom shades, and central air. The inviting kitchen offers generous cabinetry and tinted windows, bringing both charm and comfort to the heart of the home. A large deck overlooks the private backyard, while the lower-level family room with fireplace provides the perfect space to relax and entertain. The attached two-car garage adds everyday convenience. With room to roam both indoors and out - and a cul-de-sac that's long been a favorite spot for kids to play - this is a wonderful place to call home.

11 Hale Rd, Portland

$565,000

3 Beds ⋅ 4 Baths ⋅ 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

$519,900

4 Beds ⋅ 2 Baths ⋅ 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

$284,900

3 Beds ⋅ 1 Baths ⋅ 24213369 MLS

Welcome to this lovingly maintained 3-bedroom Ranch in Portland! This home has been well cared for over the years and offers a wonderful opportunity for its next owner to make it their own. Featuring central air conditioning and hardwood flooring, some of which is waiting to be uncovered, this home has great potential to truly shine with just a few cosmetic updates! The convenient single-level layout makes it an ideal option for first-time buyers, those looking to downsize, or anyone seeking easy one-floor living. The walk-out basement offers additional space and exciting possibilities for future use. Outside, enjoy the fenced-in yard, perfect for pets, gardening, entertaining, or simply relaxing. With years of thoughtful care and plenty of potential to add your personal style, this is a fantastic opportunity to create something special while building equity. Bring your vision and make this well-loved home your own!

3 Thomas St, Portland

$450,000

4 Beds ⋅ 2 Baths ⋅ 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

$495,000

3 Beds ⋅ 2 Baths ⋅ 24200193 MLS

This gracious Portland home offers nearly 2000 square feet of character, comfort, and wonderfully livable space in a desirable neighborhood. With three bedrooms and two and a half baths, the home retains the warmth and craftsmanship of an earlier era while offering the conveniences expected for modern living, including central air, public utilities, and an attached two car garage.Hardwood floors run throughout the home, complemented by exposed wood beams, handsome millwork, and inviting rooms with a sense of history and permanence. The generously sized kitchen offers abundant cabinetry, substantial counter space, stainless steel appliances, and expansive windows overlooking the property. Adjoining living spaces are equally welcoming, with warm architectural details and a fireplace that gives the home an unmistakable sense of character.The sunroom is a particularly appealing retreat, surrounded by windows and overlooking the yard. It is an ideal setting for morning coffee, a quiet afternoon with a book, or relaxed evenings enjoying the changing seasons. Upstairs, three comfortable bedrooms provide private quarters, while a walk up attic offers excellent additional storage and the practicality so often missing from homes of this vintage.Outside, the well maintained yard is framed by mature plantings and generous lawn, offering plenty of space for gardening, entertaining, recreation, or simply enjoying the outdoors. The two car garage and additional storage make everyday living

8 Robert St, Portland

$450,000

4 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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

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Portland Homes for Sale

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