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$495,000
3 Beds 2 Baths ACTIVE Status 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 ACTIVE Status 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

$345,000
3 Beds 2 Baths ACTIVE Status 24031325 MLS
HIGHEST AND BEST BY TUESDAY 9/15/2026 8PM! A little cottage with a lot to love! This charming Cape Cod sits on a picturesque corner lot in the heart of Portland, offering beautiful curb appeal and a welcoming setting. The main level features two separate living areas filled with natural light, including one with a cozy fireplace and built-in bookshelves that create a warm and inviting space full of character. A dining room with a built-in hutch, a kitchen with granite countertops, and half bath complete the main level. Upstairs, three bedrooms offer flexibility for family, guests, or a home office. Step outside and enjoy the home's special outdoor spaces, including a charming wooden pergola, established gardens, stone landscaping, and a spacious yard with plenty of room for gardening, entertaining, or simply enjoying the outdoors. And the location is hard to beat! The home is within walking distance of Portland's downtown village, Riverfront Park, and the local library. Enjoy spectacular fireworks views from the historic Arrigoni Bridge, and when you're ready for even more dining, entertainment, and things to do, Middletown's ever-growing culinary and entertainment scene is just a five-minute drive away! All while still coming home to the quiet residential setting of Fairview Street.

40 Fairview St, Portland

$365,000
3 Beds 2 Baths ACTIVE Status 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 oil tank, furnace, roof, and water heater. 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

$690,000
4 Beds 4 Baths ACTIVE Status 24196429 MLS
Custom-built by renowned local builder McGinley, this exceptional home is tucked away at the end of a peaceful private road, in the desirable The Highlands subdivision, privately situated on 3.34 acres. Thoughtfully designed and built as the builder's own residence, this spacious home offers quality craftsmanship, character, and incredible versatility throughout. A grand foyer welcomes you into the impressive front-to-back living room featuring an oversized fireplace with a stately mantle, ceilings with exposed beams and a sunken area with a slider that leads you out to a private deck creating warm inviting spaces perfect for gathering. The expansive kitchen offers abundant cabinetry, custom wood block island, pantry, hardwood floors, and a cozy seating nook overlooking the backyard. Formal dining room , mudroom and laundry area conveniently located off the kitchen. Elegant crown molding and hardwood throughout the home.The upper level offers 3 bedrooms and 2 full baths with a spacious primary suite with a walk-in closet and full bath.The finished walk-out lower level provides excellent in-law potential with an additional bedroom, kitchen, bathroom, and flexible living space. Enjoy the outdoors from the wraparound deck overlooking the tranquil, private backyard setting.

68 High St, 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

$299,000
2 Beds 1 Baths ACTIVE Status 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

$172,500
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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