Portland Homes under $600,000

Welcome to the charming city of Portland, Connecticut, a hidden gem nestled in Middlesex County. Known for its rich history, scenic landscapes, and vibrant community, Portland offers a unique blend of suburban tranquility and easy access to urban amenities. With its picturesque views of the Connecticut River and lush parks, the city is perfect for outdoor enthusiasts and families alike.

Portland boasts a welcoming atmosphere, with a strong sense of community that brings residents together through various local events and activities. The historic downtown area features quaint shops, delightful eateries, and cultural attractions, making it an ideal spot for leisurely strolls and weekend outings. Families will appreciate the top-rated schools and safe neighborhoods, ensuring a nurturing environment for children to grow and thrive.

For those looking to plant roots in this idyllic setting, Portland offers a variety of homes under $600,000. Whether you're searching for a cozy single-family residence, a charming colonial, or a modern townhouse, the real estate market here provides diverse options to suit your lifestyle and budget. With competitive pricing and a range of amenities, these homes present an excellent opportunity for first-time buyers, growing families, or anyone seeking a peaceful retreat without sacrificing convenience.

Embrace the Portland lifestyle, where community spirit meets natural beauty, and discover your dream home in this delightful Connecticut city today!

Newest Portland Homes under $600,000

$525,000

4 Beds ⋅ 3 Baths ⋅ 24212735 MLS

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

$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

$549,900

5 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

$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

$450,000

3 Beds ⋅ 4 Baths ⋅ 24206929 MLS ⋅ Grandview Farms BLDG.

Welcome to 3 Cinnamon Lane - where comfort, updates, & beautiful surroundings come together! Set in the desirable 55+ Grandview Farms community of Portland. This home offers the space & flexibility with a floor plan designed for easy everyday living & entertaining. A 1st floor primary suite with full bath, laundry & double closets provides the convenience of one-level living. There are 2 additional bedrooms & full bath upstairs offering plenty of room for guests, or a home office. The main level opens to a spacious deck overlooking woods & distant river valley views, creating a beautiful setting for morning coffee, afternoon relaxation, or entertaining friends. The finished lower level is a standout feature, offering a comfortable gathering space complete with a gas fireplace, half bath, walkout access to the patio & storage utility room. Whether used as a family room, recreation area, home office, gym, or guest space, this flexible level provides valuable additional living space and a cozy place to unwind. Recent improvements provide added peace of mind, including, newer roof, newer furnace, & central air conditioning. This unit has an attached one car garage and an amazing amount of storage! Residents also enjoy grounds maintenance, sewer, water, access to a community clubhouse, & additional guest parking.

3 Cinnamon Ln Unit 3, 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

$477,500

4 Beds ⋅ 3 Baths ⋅ 24203462 MLS

Welcome to 394 Main Street, a spacious multi-family located in the desirable Portland area. With its substantial footprint and versatile layout, this property presents an excellent opportunity for an owner occupant, extended household, or investor looking to add a valuable property to their portfolio. Whether you're looking to occupy one unit while generating rental income from another, accommodate extended family, or explore the property's investment potential, 394 Main Street offers plenty of possibilities. Located close to local shopping, dining, schools, parks, and area amenities. Portland's convenient location also provides easy access to surrounding communities and major commuter routes. With its spacious layout, multi-family versatility, and desirable Portland location, this property offers an exciting opportunity for buyers seeking both flexibility and potential. Bring your vision and make 394 Main Street your next investment or home! Schedule your private showing today! Multiple Offers Received - Highest & Best Requested By Wednesday 9/9 @10:00 AM

394 Main 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

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Portland Homes under $600,000

Newest Portland Homes under $600,000

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