Portland Homes for Sale

**Discover the Charm of Portland, Connecticut: Your Next Home Awaits**

Nestled in the heart of Middlesex County, Portland, Connecticut, is a picturesque town that beautifully combines small-town charm with modern conveniences. Known for its stunning views of the Connecticut River and a rich tapestry of history, Portland offers a unique blend of outdoor adventure, cultural experiences, and a warm community spirit. The town is dotted with lush parks, scenic trails, and vibrant local shops, making it a perfect destination for families, young professionals, and retirees alike.

Portland’s location is another one of its many advantages. With easy access to major highways, commuting to nearby cities such as Hartford and New Haven is a breeze, allowing residents to enjoy the tranquility of suburban living while still being close to urban amenities. The town is also home to several highly-rated schools, making it an ideal place for families looking to settle down.

For those in search of their dream home, Portland boasts a diverse array of properties for sale. From charming historic homes with character to modern new builds featuring the latest amenities, there is something to suit every taste and budget. Whether you’re looking for a cozy cottage or a spacious family home, the real estate market in Portland has plenty to offer.

Explore the inviting neighborhoods, friendly community, and beautiful homes that make Portland, CT, a wonderful place to call home. With its perfect blend of natural beauty and suburban comfort, your new life in Portland is just a property search away!

Newest Portland Homes for Sale

$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

$580,000

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

$539,900

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

$460,000

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

$550,000

3 Beds ⋅ 3 Baths ⋅ 24205785 MLS

Set on a beautifully landscaped .57-acre lot, 15 Payne Boulevard is a distinctive 3-bedroom Colonial offering possible 4th-bedroom flexibility and finished space across four levels. Hardwood floors lead through the main level, where a wood-burning fireplace anchors the living room and the formal dining room, eat-in kitchen, renovated half bath, first-floor laundry, and private office create a layout that works as beautifully as it lives. Upstairs, three spacious bedrooms and two full baths provide comfortable separation, while the finished walk-up third floor offers an exceptional setting for a potential fourth bedroom, studio, playroom, or second office. The finished walkout lower level adds another dimension with a generous recreation room, gym, and space for guests or hobbies. Outside, the deck overlooks a private backyard with established gardens, a basketball court, greenhouse, and versatile three-part shed. The rare heated three-car garage features tall ceilings, exceptional workspace, and additional storage beneath the third bay. A new central-air system and air handler serving the upper level add modern comfort. Near local farm stands, Arrigoni Winery, the Connecticut River, Brownstone Adventure Park, Portland's town center, and Middletown-this is where space, character, and possibility come together.

15 Payne Blvd, 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

$425,000

2 Beds ⋅ 2 Baths ⋅ 24190743 MLS

Welcome to 64 Jobs Gate 2, a custom-built Contemporary Colonial offering waterfront living at its finest on crystal-clear Jobs Pond. Enjoy water views from every room, a private beach, and your own floating dock-perfect for swimming, kayaking, fishing, or simply relaxing by the water. The home features three fireplaces, recessed lighting throughout, solid oak finishes, custom kitchen cabinetry, central vacuum (system installed but no unit), and rain-sensor skylights in the primary bedroom. Recent updates include a newer roof, remodeled bathrooms, newer bedroom flooring, and a recently painted exterior. The home is also hardwired for a generator. Ideal as a year-round residence or seasonal retreat, this peaceful property is across from Arrigoni Winery & Cider Co. and River Ridge Farm, 15 minutes from the Air Line State Park Trail, 12 minutes from Stop & Shop in East Hampton, and 20 minutes from Glastonbury.Property back on the market due to seller not receiving the EMD.No inspections were performed. Motivated sellers. All reasonable offers considered.

64 Jobs Gate, Portland

$255,000

3 Beds ⋅ 2 Baths ⋅ 24198665 MLS

Tucked away on a private rear lot off Main Street, this charming 3-bedroom, 2-bath Cape offers a great opportunity to make it your own! The .41-acre property features a spacious side yard with plenty of room for outdoor enjoyment, gardening, or entertaining. The first floor offers an open-concept living room, dining area, and kitchen with high ceilings, plus a full bathroom. Upstairs, you'll find three bedrooms and a second full bathroom. A full basement provides excellent storage space and utility area. The home is connected to public utilities and offers convenient access to local amenities. While the home could use some fresh paint and new flooring, it provides a solid opportunity to add your personal style and build equity. Conveniently located approximately 30 minutes from the Connecticut shoreline and Hartford, making this a great location for commuters and those looking to enjoy all that Connecticut has to offer. Sold AS-IS

436 Main St, Portland

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Portland Homes for Sale

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