Refine Search
Sort by
$849,900
3 Beds 4 Baths 24200612 MLS
Rarely available, this exceptional custom built home sits on 2.03 acres bordering the Portland Golf Course. Welcome to 41 Gildersleeve Road an oversized Cape, offering approximately 3,355 square feet of thoughtfully designed living space. The open-concept floor plan features spacious rooms, quality finishes, and an inviting layout designed for both everyday living and entertaining. Beautiful hardwood floors flow throughout the home, complemented by a gas fireplace framed by custom built-ins. On chilly evenings, gather around the fire and enjoy the warmth and comfort of this welcoming space. The thoughtfully designed floor plan creates an easy flow between the living, dining, and entertaining areas. Large windows fill the home with abundant natural light, enhancing the open and airy feel throughout. The home currently offers three bedrooms and three-and-a-half baths, with the flexibility of two potential primary bedroom suites-one on the first floor and another on the second floor. This versatile layout provides options to suit a variety of living arrangements. Convenience continues with laundry hookups on the first floor, as well as a dedicated laundry room in the basement. A spacious first-floor office provides an ideal work-from-home space and could also be used as a fourth bedroom.

41 Gildersleeve Rd, Portland

$459,900
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.

64 Jobs Gate, Portland

$499,900
3 Beds 2 Baths 24198960 MLS
This classic 1955 country Cape is set on 2.05 acres in a peaceful wooded setting in Portland, yet just minutes from Glastonbury and Route 2. The first floor offers a spacious family room with wood stove, kitchen, dining room, laundry room, formal living room, full bath, and a versatile additional room currently being used as a bedroom. This flexible space could also serve as a home office, den, guest room, or study, depending on your needs. With multiple adaptable spaces, this home offers the flexibility to fit your lifestyle now and as your needs change. Upstairs, you'll find three comfortable bedrooms plus a fourth room that can easily adapt to your needs as well as another full bath. This house is surprisingly spacious! The full walkout basement includes a home gym and under-house garage. Two driveways provide abundant parking and convenient space for vehicles, trailers, or equipment. A true highlight is the extraordinary 14' x 24' handcrafted timber-frame barn - an inspiring space with remarkable craftsmanship, ideal for a workshop, studio, or creative retreat. This is a property that truly must be seen to be appreciated.

251 Thompson Hill Rd, Portland

$275,000
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

$549,900
4 Beds 3 Baths 24197375 MLS
ATTRACTIVE NEW PRICE! Bursting with style and character, this beautifully updated home seamlessly blends modern finishes with thoughtful design! Gather in the dramatic family room that is sure to wow you with its wood paneled soaring ceilings, oversized barn door and fireplace. Sliders let in the natural light and lead out to the charming covered porch. Anchored by a second, brick fireplace and built-in bar, the living room creates a second option for family time or socializing. Step out from the living room onto the luxurious, fully-covered deck. This inviting space expands the living room and is ideal for indoor-outdoor entertaining. Custom plantation-style shutters keep the space cool and offer weather protection. Large dining room features a chic light fixture and can seat a large number. A convenient sitting room creates a nice flow from dining to the family room and kitchen. Speaking of the kitchen, enjoy a beautifully remodeled space in sleek grays, complete with stainless steel appliances, venting chimney and granite countertops. Adjacent breakfast nook is great for a quick bite and also leads to the updated half bath. Upstairs, enjoy hardwood throughout! Primary bedroom has 3 closets and a fully remodeled bath boasting a tiled shower and modern fixtures. Three additional, well-sized bedrooms share a second, remodeled bath in trendy black and white. Laundry is currently housed in one of the upper walk-in closets for convenience.

15 Michele Dr, Portland

$690,000
4 Beds 4 Baths 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

$525,000
4 Beds 3 Baths 24194816 MLS
Welcome to this custom-built 4-bedroom, 2.5-bath Colonial, ideally situated on a beautiful corner lot! Offering timeless craftsmanship, spacious rooms, and endless potential, this well-maintained home is ready for its next chapter. Inside, you'll find hardwood floors, including all four bedrooms. The inviting front-to-back living room features a wood-burning fireplace, while the spacious family room offers a second fireplace and direct access to the rear deck-perfect for entertaining or relaxing. The eat-in kitchen includes solid wood cabinetry, a breakfast bar, and ample workspace. The primary suite features a private bath with a stall shower and dual closets. A generously sized secondary bedroom includes a dressing area and walk-up access to a large attic, providing exceptional storage or future expansion possibilities. The partially finished lower level with fireplace offers flexible space for a recreation room, home gym, or workshop. Currently used as an in-law area.The attached two-car garage is complemented by a detached two-car carriage house with electrical service and a storage loft-ideal for hobbyists, car enthusiasts, or additional storage (Built -1997). Outside, enjoy mature trees and perennial gardens creating a beautiful backyard retreat. Built by respected local builder Don Harmon, this quality home presents a rare opportunity to personalize a classic Colonial in an exceptional location! Newer heating system and well storage tank & generator hookup

39 Old Carriage Rd, Portland

$359,000
3 Beds 1 Baths 24193978 MLS
Beautifully Updated Home with Lake Access! Welcome to this move-in-ready 3-bedroom, 1-full-bath home in one of Portland's desirable lake communities. Thoughtfully remodeled throughout, this charming home features an updated kitchen and bath, modern finishes, and a bright, inviting floor plan designed for comfortable everyday living. A newer roof and active solar panels provide added value and energy efficiency. Outside, you'll find a spacious backyard that's perfect for entertaining or relaxing, complete with a patio and plenty of room for gardening, play, or pets. The attached garage offers convenience and additional storage. Enjoy the benefits of lake access for swimming, kayaking, fishing, or simply taking in the peaceful surroundings. Combining modern updates, outdoor living, and an exceptional location, this home is ready for its next owners. Don't miss this opportunity to enjoy all that Portland has to offer!

11 Lake Rd, Portland

$499,900
4 Beds 4 Baths 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 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 offer 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 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

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.