Portland Homes under $400,000

Welcome to the charming city of Portland, Connecticut, nestled in the picturesque Middlesex County. Known for its rich history and vibrant community, Portland offers a unique blend of small-town charm and modern conveniences. With its scenic views along the Connecticut River and a diverse array of parks and recreational activities, it’s no wonder why families and individuals are drawn to this delightful area.

Portland’s historic downtown area features quaint shops, inviting cafes, and local eateries, perfect for enjoying a leisurely afternoon. The town’s commitment to community is evident in its numerous events and festivals throughout the year, fostering a warm and welcoming atmosphere. Nature enthusiasts will appreciate the abundance of outdoor activities, from hiking the trails at Brownstone Park to exploring the serene beauty of the Connecticut River.

For those looking to plant roots in this idyllic town, Portland offers an impressive selection of homes priced under $400,000. Whether you're a first-time homebuyer, a growing family, or looking to downsize, you'll find a variety of charming properties that cater to your needs. From cozy single-family homes to well-maintained townhouses, there’s something for everyone in this price range. With its affordable housing options and a strong sense of community, Portland is an ideal place to call home.

Explore the possibilities of living in Portland, CT, where a vibrant lifestyle awaits you amidst stunning natural beauty and a friendly, close-knit community. Your dream home might just be around the corner!

Newest Portland Homes under $400,000

$319,900

4 Beds ⋅ 2 Baths ⋅ 24209538 MLS

Great opportunity to own a two-family home in the desirable town of Portland! This versatile property offers the potential for rental income, multi-generational living, or an owner-occupied investment. Each unit provides its own living space and offers flexibility for a variety of needs. Conveniently located near local amenities, shopping, dining, schools, and major commuter routes. Whether you're looking to expand your investment portfolio or have one unit help offset your living expenses, this property is worth a look. Don't miss this opportunity!

64 Summer St, Portland

$364,900

2 Beds ⋅ 2 Baths ⋅ 24208065 MLS ⋅ Grandview Farms BLDG.

Welcome to 17 Ginger Circle, a beautifully maintained 2BR/2Bath condo tucked into Portland's sought-after 55+ community. Designed for easy, low-maintenance living, this home offers one-floor convenience, immaculately maintained! Walk up attic and full walk out basement, great potential. Residents enjoy clubhouse, landscaping/snow removal included, etc., all just minutes from Portland's shops, dining, and the Connecticut River. Desirable home in desirable 55+ Community!

17 Ginger Cir Unit 17, Portland

$365,000

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

$375,000

3 Beds ⋅ 1 Baths ⋅ 24200519 MLS

3 bedroom Ranch on lovely location on a cul-de-sac road. This ranch offers 3 nice size bedrooms (note - town hall lists as a 2 bedroom). Oak floors in bedrooms and living room, the livingroom has wood burning fireplace and a dining area with corner hutch. Kitchen can be closed off by pocket door. House originally had 1 car garage, an oversize additional bay was added and plumbed to have radiant heat in floor. This home has a nice layout, is solid but needs updating to the kitchen and bathroom. All functional but really needs remodel. Breezeway between house and garage. Yard is rolling so there is level area's. Shed on rear of property. Basement unfinished.

3 Edwards 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

$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

$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 offers 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

$149,000

1 Beds ⋅ 1 Baths ⋅ 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

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.