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Custom-built, Salt Box Colonial 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 2.34 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.

4 Beds ⋅ 4 Baths ⋅ 24196429 MLS

Custom-built, Salt Box Colonial 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 2.34 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

$550,000

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.

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

$525,000

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

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

$495,000

Opportunity to acquire a tenant-occupied in the transitioning and upcoming Portland, Connecticut submarket. Situated along the Route 66 commercial corridor, this single-tenant building offers an income-producing investment opportunity in Middlesex County. This YOUNG office building built in 2008 offers modern features, irrigation, and lovely positioning with Rt 66 visibility. Conveniently located near downtown Portland, Middletown, and the Arrigoni Bridge, with access to Route 9 and surrounding Central Connecticut communities. The existing tenancy offers investors an opportunity to acquire an occupied commercial asset with a simplified management structure. Ideal for investors seeking to expand their commercial real estate portfolio in the Greater Middletown market or owner user willing to wait for occupancy for a short period. Property is offered subject to existing tenancy. Lease terms and financial information available upon request.

2 Baths ⋅ 24211950 MLS

Opportunity to acquire a tenant-occupied in the transitioning and upcoming Portland, Connecticut submarket. Situated along the Route 66 commercial corridor, this single-tenant building offers an income-producing investment opportunity in Middlesex County. This YOUNG office building built in 2008 offers modern features, irrigation, and lovely positioning with Rt 66 visibility. Conveniently located near downtown Portland, Middletown, and the Arrigoni Bridge, with access to Route 9 and surrounding Central Connecticut communities. The existing tenancy offers investors an opportunity to acquire an occupied commercial asset with a simplified management structure. Ideal for investors seeking to expand their commercial real estate portfolio in the Greater Middletown market or owner user willing to wait for occupancy for a short period. Property is offered subject to existing tenancy. Lease terms and financial information available upon request.

150 Marlborough St, Portland

$495,000

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

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

$477,500

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

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

$429,000

*Offer deadline 10/17 8pm* over the South Glastonbury line, a timeless New England classic awaits. Nestled within a lovely neighborhood, this charming 3-bedroom, 2.5-bath Dutch Colonial is rich with character, from hardwood floors and exposed beams to classic wainscoting and thoughtfully placed built-ins. A gracious front-to-back living room welcomes you with a wood-burning fireplace and beautiful bay window, creating an inviting space to gather, unwind, and enjoy the changing seasons. The spacious eat-in kitchen pairs warm wood cabinetry with granite countertops and stainless steel appliances, while sliding glass doors open to the deck, making entertaining feel effortless. Outside, a beautifully level, fenced backyard offers room to roam, play, and gather around the firepit on crisp evenings. Upstairs, find the en suite primary bedroom and two additional bedrooms serviced by a hallway full bath. In the basement, approximately 276 square feet of finished space provides flexibility for a home office, recreation, or hobbies. Attached two-car garage accessed from the kitchen adds everyday convenience. Beyond its undeniable charm, the home has benefited from years of attentive ownership, with significant improvements including the roof, windows, well pump, &front walkway. Well cared for &ideally situated with easy access to all that Portland & neighboring Glastonbury have to offer, 25 Karen Drive is the kind of place that makes coming home the best part of the day

3 Beds ⋅ 3 Baths ⋅ 24212132 MLS

*Offer deadline 10/17 8pm* over the South Glastonbury line, a timeless New England classic awaits. Nestled within a lovely neighborhood, this charming 3-bedroom, 2.5-bath Dutch Colonial is rich with character, from hardwood floors and exposed beams to classic wainscoting and thoughtfully placed built-ins. A gracious front-to-back living room welcomes you with a wood-burning fireplace and beautiful bay window, creating an inviting space to gather, unwind, and enjoy the changing seasons. The spacious eat-in kitchen pairs warm wood cabinetry with granite countertops and stainless steel appliances, while sliding glass doors open to the deck, making entertaining feel effortless. Outside, a beautifully level, fenced backyard offers room to roam, play, and gather around the firepit on crisp evenings. Upstairs, find the en suite primary bedroom and two additional bedrooms serviced by a hallway full bath. In the basement, approximately 276 square feet of finished space provides flexibility for a home office, recreation, or hobbies. Attached two-car garage accessed from the kitchen adds everyday convenience. Beyond its undeniable charm, the home has benefited from years of attentive ownership, with significant improvements including the roof, windows, well pump, &front walkway. Well cared for &ideally situated with easy access to all that Portland & neighboring Glastonbury have to offer, 25 Karen Drive is the kind of place that makes coming home the best part of the day

25 Karen Dr, Portland

$425,000

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.

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

$415,000

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.

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

$364,900

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!

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

$350,000

Welcome to the beauty and convenience of one-floor living! This inviting ranch offers an open-concept layout with the living room, dining room, and kitchen flowing seamlessly together, all accented by hardwood floors and vaulted ceilings. Double sliders fill the space with natural light and create an effortless indoor/outdoor feel, opening to a spacious wraparound Trex deck with vinyl railings-perfect for relaxing or entertaining. The kitchen features granite countertops and stainless steel appliances, while convenient walk-in showers add to the ease of everyday living. Step outside and enjoy a truly unique piece of Portland history, with a distinctive brownstone silo located at the rear of the property. Ideally situated within walking distance to a nearby park and summer music, and just minutes from Route 9 for an easy commute. Enjoy the restaurants, shops, and amenities of Main Street Middletown, all conveniently close by. A wonderful combination of comfort, character, and location! Best and final due Tuesday 9/22 at noon.

3 Beds ⋅ 2 Baths ⋅ 24207354 MLS

Welcome to the beauty and convenience of one-floor living! This inviting ranch offers an open-concept layout with the living room, dining room, and kitchen flowing seamlessly together, all accented by hardwood floors and vaulted ceilings. Double sliders fill the space with natural light and create an effortless indoor/outdoor feel, opening to a spacious wraparound Trex deck with vinyl railings-perfect for relaxing or entertaining. The kitchen features granite countertops and stainless steel appliances, while convenient walk-in showers add to the ease of everyday living. Step outside and enjoy a truly unique piece of Portland history, with a distinctive brownstone silo located at the rear of the property. Ideally situated within walking distance to a nearby park and summer music, and just minutes from Route 9 for an easy commute. Enjoy the restaurants, shops, and amenities of Main Street Middletown, all conveniently close by. A wonderful combination of comfort, character, and location! Best and final due Tuesday 9/22 at noon.

34 Middlesex Ave Extension, Portland

$299,000

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.

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

$284,900

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 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

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