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One-of-a-Kind Custom-Built Home in a Desirable Middletown Location! Beautifully custom-built with exceptional space, craftsmanship, and versatility, this stunning property is perfect for multigenerational living, entertaining, or simply enjoying all the comforts of a truly special home. Featuring 5-6 bedrooms, 4 full 2 half bathrooms, this home offers room for everyone! The chef-inspired kitchen features a spacious eat-in area, making it the perfect gathering place for family and friends. Large windows throughout fill the home with natural light, while gorgeous cherry hardwood floors add warmth and elegance. The first-floor primary suite offers convenience and privacy. Upstairs, you'll find an additional 4-5 bedrooms, 3 full and 1 half bath, providing plenty of space for all, or work-from-home needs. A generously sized bonus room offers endless possibilities. Create your dream playroom, home office, studio, additional bedroom, or whatever suits your lifestyle! Love entertaining? Step outside and enjoy the beautiful patio, inground pool, and expansive yard perfect for summer gatherings, backyard fun, and unforgettable parties. A spacious 3-car garage adds even more convenience. The possibilities continue with the lower level, which could be finished to create an expansive in-law suite with its own driveway, offering incredible multigenerational potential. Or transform the space into the ultimate entertainment retreat for movie nights, game days, and gatherings with friends.

6 Beds ⋅ 4 Baths ⋅ 24217881 MLS

One-of-a-Kind Custom-Built Home in a Desirable Middletown Location! Beautifully custom-built with exceptional space, craftsmanship, and versatility, this stunning property is perfect for multigenerational living, entertaining, or simply enjoying all the comforts of a truly special home. Featuring 5-6 bedrooms, 4 full 2 half bathrooms, this home offers room for everyone! The chef-inspired kitchen features a spacious eat-in area, making it the perfect gathering place for family and friends. Large windows throughout fill the home with natural light, while gorgeous cherry hardwood floors add warmth and elegance. The first-floor primary suite offers convenience and privacy. Upstairs, you'll find an additional 4-5 bedrooms, 3 full and 1 half bath, providing plenty of space for all, or work-from-home needs. A generously sized bonus room offers endless possibilities. Create your dream playroom, home office, studio, additional bedroom, or whatever suits your lifestyle! Love entertaining? Step outside and enjoy the beautiful patio, inground pool, and expansive yard perfect for summer gatherings, backyard fun, and unforgettable parties. A spacious 3-car garage adds even more convenience. The possibilities continue with the lower level, which could be finished to create an expansive in-law suite with its own driveway, offering incredible multigenerational potential. Or transform the space into the ultimate entertainment retreat for movie nights, game days, and gatherings with friends.

40 Pinehurst Pl, Middletown

$600,000

Exceptional Mixed Use 3-Unit Investment Opportunity in Middletown! Well-maintained three-unit property offering the feel of townhouse-style living with the income potential of a multifamily investment. Each spacious unit features 3 bedrooms, 1 full bath, 1 half bath, an eat-in kitchen, abundant natural light, basement storage, and washer/dryer hookups. A standout feature is the private under-building garage for each unit with direct access, plus ample off-street parking and a rear driveway. Separate utilities provide added convenience for ownership and management. Ideally located near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. An excellent opportunity for an investor or owner-occupant looking to generate rental income while building equity. Property being Sold As Is. Agent/Owner related.

9 Beds ⋅ 6 Baths ⋅ 24209312 MLS

Exceptional Mixed Use 3-Unit Investment Opportunity in Middletown! Well-maintained three-unit property offering the feel of townhouse-style living with the income potential of a multifamily investment. Each spacious unit features 3 bedrooms, 1 full bath, 1 half bath, an eat-in kitchen, abundant natural light, basement storage, and washer/dryer hookups. A standout feature is the private under-building garage for each unit with direct access, plus ample off-street parking and a rear driveway. Separate utilities provide added convenience for ownership and management. Ideally located near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. An excellent opportunity for an investor or owner-occupant looking to generate rental income while building equity. Property being Sold As Is. Agent/Owner related.

227 E Main St, Middletown

$579,900

Group showing Sunday, 10/18, 12 noon! Fantastic investment opportunity just minutes from Downtown Middletown! This beautifully maintained three-family property offers a great combination of location, condition, and long-term investment potential. All three units offer two large bedrooms. Each unit also enjoys its own private porch or balcony, giving tenants valuable outdoor space. This property has been well cared for with significant updates throughout, including impeccably updated mechanicals, helping take some of the worry out of owning a multifamily property. A three-car detached garage in the rear adds even more value, along with additional off-street parking. Located on a quiet, desirable street close to Downtown Middletown, the property offers easy access to restaurants, shopping, Wesleyan University, major routes, and everything the downtown area has to offer. Whether you're looking to add a solid three-family to your investment portfolio or live in one unit while collecting rent from the other two, this is the type of multifamily property that is getting harder to find. Great location, private outdoor spaces, garage, strong updates, and three income-producing units all in one property. Don't wait on this one-schedule a showing and see the opportunity for yourself!

6 Beds ⋅ 3 Baths ⋅ 24208519 MLS

Group showing Sunday, 10/18, 12 noon! Fantastic investment opportunity just minutes from Downtown Middletown! This beautifully maintained three-family property offers a great combination of location, condition, and long-term investment potential. All three units offer two large bedrooms. Each unit also enjoys its own private porch or balcony, giving tenants valuable outdoor space. This property has been well cared for with significant updates throughout, including impeccably updated mechanicals, helping take some of the worry out of owning a multifamily property. A three-car detached garage in the rear adds even more value, along with additional off-street parking. Located on a quiet, desirable street close to Downtown Middletown, the property offers easy access to restaurants, shopping, Wesleyan University, major routes, and everything the downtown area has to offer. Whether you're looking to add a solid three-family to your investment portfolio or live in one unit while collecting rent from the other two, this is the type of multifamily property that is getting harder to find. Great location, private outdoor spaces, garage, strong updates, and three income-producing units all in one property. Don't wait on this one-schedule a showing and see the opportunity for yourself!

225 Pearl St, Middletown

$369,900

Ideal for an investor or owner occupant this 2 family home offers 2 units 5 rooms with 3 bedrooms each. The first floor unit with hardwood floors 3 spacious bedrooms, refreshed bath, and a kitchen with a walk in pantry. The second floor has been remodeled with 3 bedrooms and the primary bedroom with a large walk in closet or storage room. Updated kitchen, laminate floor, white cabinets and walk in pantry and refreshed full bath with tile tub surround and floor. This property has a front porch and a rear porches. A walk up attic offers additional space with an option for future expansion. A full basement with a full bath and a finished room. Furnaces and Hot water heaters replaced in 2021. Driveway which will allow for 2 cars of off street parking. Great opportunity to add to a portfolio.

6 Beds ⋅ 2 Baths ⋅ 24208513 MLS

Ideal for an investor or owner occupant this 2 family home offers 2 units 5 rooms with 3 bedrooms each. The first floor unit with hardwood floors 3 spacious bedrooms, refreshed bath, and a kitchen with a walk in pantry. The second floor has been remodeled with 3 bedrooms and the primary bedroom with a large walk in closet or storage room. Updated kitchen, laminate floor, white cabinets and walk in pantry and refreshed full bath with tile tub surround and floor. This property has a front porch and a rear porches. A walk up attic offers additional space with an option for future expansion. A full basement with a full bath and a finished room. Furnaces and Hot water heaters replaced in 2021. Driveway which will allow for 2 cars of off street parking. Great opportunity to add to a portfolio.

42 Grand St, Middletown

$1,395,000

Two-building mixed-use investment opportunity in Middletown. The offering includes 61 East Main Street with four apartments and two storefronts, plus a separate three-apartment building at 2-6 Flower Street, offering a more private off Main street setting. Six apartments are occupied, while the seventh is being updated with a new kitchen and bathroom. Upon completion and lease-up at the projected rent, the property is expected to offer an approximately 9% cap rate, that's before any income from the two vacant storefronts. Zoned MXI, the storefronts have previously operated as a clothing store, salon and convenience store in past years, offering flexible possibilities subject to zoning guidelines. Additional features include private off-street parking space, wood flooring, same ownership since 2014, units updated/repaired over ownership for housing voucher compliance/inspections, separate utilities, a yard area and visible East Main Street frontage. With a Walk Score of 74, the property is close to Downtown Middletown, restaurants, shops, services, Wesleyan University, the riverfront, public transportation and Route 9. Two buildings, one investment and multiple opportunities to increase income!!! Interior pics will be added prior to active date.

21 Beds ⋅ 9 Baths ⋅ 24206879 MLS

Two-building mixed-use investment opportunity in Middletown. The offering includes 61 East Main Street with four apartments and two storefronts, plus a separate three-apartment building at 2-6 Flower Street, offering a more private off Main street setting. Six apartments are occupied, while the seventh is being updated with a new kitchen and bathroom. Upon completion and lease-up at the projected rent, the property is expected to offer an approximately 9% cap rate, that's before any income from the two vacant storefronts. Zoned MXI, the storefronts have previously operated as a clothing store, salon and convenience store in past years, offering flexible possibilities subject to zoning guidelines. Additional features include private off-street parking space, wood flooring, same ownership since 2014, units updated/repaired over ownership for housing voucher compliance/inspections, separate utilities, a yard area and visible East Main Street frontage. With a Walk Score of 74, the property is close to Downtown Middletown, restaurants, shops, services, Wesleyan University, the riverfront, public transportation and Route 9. Two buildings, one investment and multiple opportunities to increase income!!! Interior pics will be added prior to active date.

61 E Main St, Middletown

$779,000

A truly extraordinary residence where distinctive architecture, exceptional privacy and sophisticated design come together to create a home unlike any other. Privately set on 3.5 acres, this beautifully renovated contemporary offers more than 5,500 square feet of impressive living space, with soaring interiors, walls of windows and an abundance of natural light creating a seamless connection to the surrounding landscape. The beautifully designed kitchen features quartz countertops, stainless steel appliances, double ovens, and generous space for gathering and entertaining. Two striking stone fireplaces serve as dramatic focal points, adding warmth, texture and character to the home's expansive living spaces. Offering six bedrooms and three-and-a-half beautifully renovated baths, the versatile floor plan provides exceptional flexibility for today's lifestyle. With its generous proportions and abundance of private and flexible spaces, the home is ideally suited for multigenerational living, extended family, guests, or those seeking dedicated space for a home office or home-based business. A fabulous loft provides yet another versatile area for a family room, office or game room. The spacious primary suite offers a walk-in closet, beautifully updated bath and private patio overlooking the peaceful surroundings. Throughout the home, meticulous details, interesting architectural elements and thoughtfully designed spaces create a sense of character rarely found in

6 Beds ⋅ 4 Baths ⋅ 24199581 MLS

A truly extraordinary residence where distinctive architecture, exceptional privacy and sophisticated design come together to create a home unlike any other. Privately set on 3.5 acres, this beautifully renovated contemporary offers more than 5,500 square feet of impressive living space, with soaring interiors, walls of windows and an abundance of natural light creating a seamless connection to the surrounding landscape. The beautifully designed kitchen features quartz countertops, stainless steel appliances, double ovens, and generous space for gathering and entertaining. Two striking stone fireplaces serve as dramatic focal points, adding warmth, texture and character to the home's expansive living spaces. Offering six bedrooms and three-and-a-half beautifully renovated baths, the versatile floor plan provides exceptional flexibility for today's lifestyle. With its generous proportions and abundance of private and flexible spaces, the home is ideally suited for multigenerational living, extended family, guests, or those seeking dedicated space for a home office or home-based business. A fabulous loft provides yet another versatile area for a family room, office or game room. The spacious primary suite offers a walk-in closet, beautifully updated bath and private patio overlooking the peaceful surroundings. Throughout the home, meticulous details, interesting architectural elements and thoughtfully designed spaces create a sense of character rarely found in

44 Chamberlain Hill Rd, Middletown

$419,000

Exceptional mixed-use investment opportunity convenient to downtown Middletown! This property features 2 commercial units and 3 residential units, offering a balanced blend of commercial and residential income that makes it an ideal addition to any investor's portfolio. Both commercial spaces are currently vacant, making this an excellent opportunity for someone who wants to open their own business on the ground floor while collecting steady rental income from the apartments upstairs. The commercial spaces enjoy excellent street frontage and high visibility along busy East Main Street, providing strong exposure for retail, office, or service-oriented businesses-with one of the commercial units already featuring a dedicated kitchen. The 3 residential units offer versatile 1, 2, and 3 bedroom layouts, each featuring 1 full bathroom. These units offer strong rental appeal in a highly desirable location. Situated within walking distance to restaurants, shopping, entertainment, public transportation, and local amenities, this property benefits from Middletown's vibrant atmosphere. Whether you're looking to expand your investment portfolio, generate multiple income streams, or establish your business while collecting residential rental income, this versatile property offers outstanding potential. Convenient access to Route 9, I-91, Wesleyan University, and surrounding communities. Make an appointment today to view this property!

8 Beds ⋅ 4 Baths ⋅ 24190092 MLS

Exceptional mixed-use investment opportunity convenient to downtown Middletown! This property features 2 commercial units and 3 residential units, offering a balanced blend of commercial and residential income that makes it an ideal addition to any investor's portfolio. Both commercial spaces are currently vacant, making this an excellent opportunity for someone who wants to open their own business on the ground floor while collecting steady rental income from the apartments upstairs. The commercial spaces enjoy excellent street frontage and high visibility along busy East Main Street, providing strong exposure for retail, office, or service-oriented businesses-with one of the commercial units already featuring a dedicated kitchen. The 3 residential units offer versatile 1, 2, and 3 bedroom layouts, each featuring 1 full bathroom. These units offer strong rental appeal in a highly desirable location. Situated within walking distance to restaurants, shopping, entertainment, public transportation, and local amenities, this property benefits from Middletown's vibrant atmosphere. Whether you're looking to expand your investment portfolio, generate multiple income streams, or establish your business while collecting residential rental income, this versatile property offers outstanding potential. Convenient access to Route 9, I-91, Wesleyan University, and surrounding communities. Make an appointment today to view this property!

71 E Main St, Middletown

$410,000

Turnkey multifamily for owner occupied or investment opportunity in a desirable Middletown location! This fully remodeled property offers strong income potential with updated units featuring modern kitchens, renovated bathrooms, new flooring, and contemporary finishes throughout. The building has been well maintained and provides an excellent opportunity for investors seeking a low-maintenance asset with immediate cash flow. Conveniently located near downtown Middletown, shopping, restaurants, schools, parks, and major highways, making it attractive to tenants and ensuring long-term rental demand. Whether you're expanding your portfolio or acquiring your first investment property, this move-in-ready multifamily is an opportunity you won't want to miss. Being SOLD AS-IS.

6 Beds ⋅ 2 Baths ⋅ 24188066 MLS

Turnkey multifamily for owner occupied or investment opportunity in a desirable Middletown location! This fully remodeled property offers strong income potential with updated units featuring modern kitchens, renovated bathrooms, new flooring, and contemporary finishes throughout. The building has been well maintained and provides an excellent opportunity for investors seeking a low-maintenance asset with immediate cash flow. Conveniently located near downtown Middletown, shopping, restaurants, schools, parks, and major highways, making it attractive to tenants and ensuring long-term rental demand. Whether you're expanding your portfolio or acquiring your first investment property, this move-in-ready multifamily is an opportunity you won't want to miss. Being SOLD AS-IS.

163 Pearl St, Middletown

$390,000

Owner occupied or investors! Fully renovated investment opportunity in the heart of Middletown! This well-maintained 7 bedrooms 2 bath, multifamily property has been completely remodeled and offers immediate cash flow with tenants already in place. Each unit is currently rented, providing strong and stable rental income from day one. Updates include modern kitchens, renovated bathrooms, updated flooring, fixtures, and mechanical improvements throughout. The property has been thoughtfully upgraded while maintaining its charm and functionality. Ideal for investors seeking a turnkey asset with reliable tenants and minimal deferred maintenance. Conveniently located near shopping, restaurants, schools, public transportation, and major highways. Don't miss this opportunity to add a fully occupied, income-producing property to your portfolio. Being SOLD AS-IS. OWNER/AGENT.

7 Beds ⋅ 2 Baths ⋅ 24188106 MLS

Owner occupied or investors! Fully renovated investment opportunity in the heart of Middletown! This well-maintained 7 bedrooms 2 bath, multifamily property has been completely remodeled and offers immediate cash flow with tenants already in place. Each unit is currently rented, providing strong and stable rental income from day one. Updates include modern kitchens, renovated bathrooms, updated flooring, fixtures, and mechanical improvements throughout. The property has been thoughtfully upgraded while maintaining its charm and functionality. Ideal for investors seeking a turnkey asset with reliable tenants and minimal deferred maintenance. Conveniently located near shopping, restaurants, schools, public transportation, and major highways. Don't miss this opportunity to add a fully occupied, income-producing property to your portfolio. Being SOLD AS-IS. OWNER/AGENT.

194 Liberty St, Middletown

$1,300,000

Welcome to 480 Main Street, Middletown - a rare investment opportunity in the heart of Downtown Middletown! This stunning brick mixed-use building blends timeless character with strong income-producing potential. Featuring 8 spacious residential units, each offering 900+ square feet, soaring ceilings, beautiful hardwood flooring, functional built-ins, and oversized layouts that tenants love. Seven of the Eight residential units have been updated, and many feature newer hot water heaters, helping minimize future capital expenses. The property is anchored by two commercial storefronts, including a 3,100 SF space and a 1,100 SF (long-term tenant). Commercial tenants contribute approximately 40% of CAM expenses, creating additional value for ownership. Featuring classic brick construction, a well-maintained roof, and a prime downtown location, 480 Main Street offers a rare blend of character, stability, and investment potential. Located just steps from restaurants, shopping, and entertainment, this is an excellent opportunity to own a standout mixed-use asset in the heart of Middletown

8 Beds ⋅ 10 Baths ⋅ 24182655 MLS

Welcome to 480 Main Street, Middletown - a rare investment opportunity in the heart of Downtown Middletown! This stunning brick mixed-use building blends timeless character with strong income-producing potential. Featuring 8 spacious residential units, each offering 900+ square feet, soaring ceilings, beautiful hardwood flooring, functional built-ins, and oversized layouts that tenants love. Seven of the Eight residential units have been updated, and many feature newer hot water heaters, helping minimize future capital expenses. The property is anchored by two commercial storefronts, including a 3,100 SF space and a 1,100 SF (long-term tenant). Commercial tenants contribute approximately 40% of CAM expenses, creating additional value for ownership. Featuring classic brick construction, a well-maintained roof, and a prime downtown location, 480 Main Street offers a rare blend of character, stability, and investment potential. Located just steps from restaurants, shopping, and entertainment, this is an excellent opportunity to own a standout mixed-use asset in the heart of Middletown

480 Main St, Middletown

$1,300,000

Unique mixed-use opportunity in Middletown offering strong cash flow and flexible ownership potential. Property consists of a fully occupied 4-family, a fully occupied 2-family, and two 1,600 SF commercial garage/workshop spaces all situated on one lot with views of the Connecticut River and Arrigoni Bridge. One commercial space is leased, while the second vacant garage offers ideal owner-user potential for contractors, storage, workshop space, or additional rental income. Projected 8.2% cap at current occupancy, with stabilization potential of approximately 9.4-9.8% upon lease of the 2nd garage. Residential units feature a desirable mix of 1-, 2-, and 3-bedroom layouts with updates completed over time, including newer boilers and water heaters. Off-street parking, minutes to Route 9, downtown Middletown, and walking distance to Wesleyan University. Property conveyed as-is.

12 Beds ⋅ 8 Baths ⋅ 24178851 MLS

Unique mixed-use opportunity in Middletown offering strong cash flow and flexible ownership potential. Property consists of a fully occupied 4-family, a fully occupied 2-family, and two 1,600 SF commercial garage/workshop spaces all situated on one lot with views of the Connecticut River and Arrigoni Bridge. One commercial space is leased, while the second vacant garage offers ideal owner-user potential for contractors, storage, workshop space, or additional rental income. Projected 8.2% cap at current occupancy, with stabilization potential of approximately 9.4-9.8% upon lease of the 2nd garage. Residential units feature a desirable mix of 1-, 2-, and 3-bedroom layouts with updates completed over time, including newer boilers and water heaters. Off-street parking, minutes to Route 9, downtown Middletown, and walking distance to Wesleyan University. Property conveyed as-is.

13-15 Portland St, Middletown

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