Middleboro Homes with Off Street Parking Features

Welcome to Middleboro, Massachusetts, a charming town nestled in the heart of Plymouth County. Known for its rich history and vibrant community, Middleboro offers a unique blend of small-town charm and modern conveniences. With its picturesque landscapes, friendly neighborhoods, and a strong sense of community, it's no wonder that many are drawn to call this town home.

Middleboro boasts a variety of amenities including local parks, shops, and dining options, making it easy for residents to enjoy a fulfilling lifestyle. The town is also conveniently located near major highways, providing easy access to nearby cities like Boston and Providence, making it perfect for commuters. Nature enthusiasts will appreciate the nearby lakes and trails, perfect for hiking, fishing, or simply enjoying the great outdoors.

One of the standout features of homes in Middleboro is the availability of off-street parking. This highly sought-after amenity ensures that you’ll never have to worry about finding a parking spot after a long day. Whether you’re hosting friends for a weekend barbecue or simply coming home from work, having your own designated parking space adds a layer of convenience and comfort to your living experience.

With a range of homes available, many featuring off-street parking, Middleboro is an ideal place for families, young professionals, and retirees alike. Explore the charming streets and discover the perfect home that fits your lifestyle. In Middleboro, you’ll find not just a house, but a place to truly call home. Come and experience the warmth and community spirit that makes Middleboro a delightful place to live!

Newest Middleboro Homes with Off Street Parking Features

$440,000

2 Beds ⋅ 2 Baths ⋅ 73556144 MLS ⋅ ['Ashley Place'] BLDG.

Welcome home to one-level living! This rare 2 bedroom ranch style condo offers a truly elevated living experience with absolutely no expense spared. The main level displays hardwood floors, an elegant Italian tile foyer, Hunter Douglas window treatments & designer light fixtures. The kitchen is smartly designed with custom cabinetry, granite countertops and updated appliances. The light-filled dining area flows into a spacious living room with sky lights, a fireplace and a new Anderson slider. Step out onto your private deck outfitted with custom blinds for ultimate privacy overlooking a beautifully landscaped stone patio oasis and rock garden. Two generous bedrooms reside on the main floor with a full size en-suite bathroom. There is also a 1/2 bathroom on the main level. Downstairs, the finished basement expands your living space with 2 large, versatile rooms perfect for a home office, media room or guest quarters. This turn-key showplace won't last-schedule your showing today!

151 Ashley Lane Unit 151, Middleboro

Listing courtesy of Listing Agent: Donna Crandall from Listing Office: Busch Realty Group, LLC.

$389,000

3 Beds ⋅ 2 Baths ⋅ 73556084 MLS

Showings begin on Thursday 9/30, commuter open house, 5:00 - 7:00. Welcome to 408 Green Street in the desirable Oak Point 55+ Community! This attractive Princeton-style home is bright, open, and inviting, creating a great first impression from the moment you step inside. The thoughtfully designed split-bedroom floor plan offers both privacy and comfort. The primary suite features two closets and a private bath with a step-in shower. A nice sized living room flows seamlessly into the dining room, creating an ideal setting for everyday living and entertaining. The well-appointed kitchen offers abundant cabinetry, updated stainless steel appliances, vinyl flooring, and a morning room for casual dining (virtually staged with a table). A sliding glass door opens to the spacious screened porch with wood flooring—the perfect place to enjoy your morning coffee, unwind with a good book, or entertain family and friends. Located on the other side of the home are two additional bedrooms. These 2 rooms have been virtually staged to showcase their flexibility as a comfortable guest bedroom a craft room or home office, a full hall bath with a tub/shower combination. Built in 2003, this manufactured home on leased land offers 1,344 square feet of living space on a nicely situated lot. Additional features include attractive Pergo flooring in the main living areas and vinyl flooring in the kitchen and baths (no wall-to-wall carpeting), and a one-car garage. Updates: Refrigerator & stove April 2026, furnace and central air conditioning system replaced in 2022, Leaf Guard, gutter system and a roof replacement in 2016. Enjoy the exceptional Oak Point lifestyle with resort-style amenities, including three swimming pools (two outdoor), tennis and pickleball courts, bocce, a fitness center, gym, a 300-seat ballroom, billiards room, a library, and an extensive selection of clubs, classes, and social activities. Fee includes; lawn mowing, snow removal, trash pickup, sewer treatment and amenities.

408 Green Street, Middleboro

Listing courtesy of Listing Agent: Toni Manning from Listing Office: Conway - Hanover.

$485,000

2 Beds ⋅ 1 Baths ⋅ 73555583 MLS

If you have been searching for affordability, look no further! Offered below $500,000 and on Middleboro gas and electric, the carrying costs are sure to be the best deal on the South Shore. You can also enjoy peace of mind as a homeowner because many of the big-ticket items have been taken care of recently! The bathroom was redone in 2023, new windows in 2024, kitchen renovation in 2021, central air in 2023, switched from oil to gas in 2018 and installed a new furnace, siding and roof in 2024, replaced and upgraded electric panel in 2018 w/ 200 amp service, and septic was replaced in 2016. You can start packing, call the movers, and settle in to your new home! Enjoy one-level living with the option to expand in the large walkout basement. Set on a 1/2 acre, it is the perfect-sized yard for entertaining and enjoying a summer afternoon! Conveniently located near Rte. 44, this is an ideal location for commuters and anyone looking to enjoy all the South Shore has to offer in a short drive! The minute you enter this adorable ranch-style home, you will see the thoughtful upgrades and renovations made by the seller, as this home showcases pride of ownership throughout!

688 Plymouth St, Middleboro

Listing courtesy of Listing Agent: Moriah Wicker from Listing Office: Keller Williams Realty Colonial Partners.

$799,000

3 Beds ⋅ 2 Baths ⋅ 73555359 MLS

Welcome to 229 Tispaquin! This charming 3-bedroom, 2-bathroom home sits on a beautiful 2.8-acre lot and offers the perfect blend of comfort, space, and versatility. A true highlight of the property is the impressive 40' x 30' detached garage, complete with electricity, vehicle lift, wood stove, and a spacious loft area above, perfect for hobbies, projects, storage, or recreational use.Inside, the spacious kitchen features an oversized center island, gas range, and plenty of cabinet and counter space, making it the perfect gathering spot. Just off the kitchen, the mudroom includes a pellet stove for added warmth and convenience. Enjoy the bright sunroom overlooking the property, or relax in the inviting living room with a fireplace and pellet stove insert.The flexible first-floor bonus room is currently used as an additional bedroom but could also serve as a home office, guest room, playroom, or den. Central air keeps the home comfortable year-round. The partially finished basement offers additional living space, laundry, and plenty of storage.Outside, enjoy the brand-new deck, perfect for relaxing or entertaining, along with an oversized shed for tools, lawn equipment, and outdoor gear. With its expansive lot, incredible garage setup, and thoughtful features throughout, 229 Tispaquin offers space and versatility that are hard to find. Conveniently located near local amenities, shopping, dining, and commuter routes, this is one you won't want to miss!

229 Tispaquin St, Middleboro

Listing courtesy of Listing Agent: Elizabeth Moses from Listing Office: LPT Realty - Home & Key Group.

$399,000

3 Beds ⋅ 2 Baths ⋅ 73554455 MLS

Offer deadline 7/26, Sunday 10 AM. Make offers good until 6pm. Oak Point ~ one of the South Shore's premier 55+ communities, where resort-style amenities and an active, social lifestyle come together. This well-maintained Princeton-style home offers 3 bedrooms, 2 full baths, and 1,456 square feet of thoughtfully designed living space. Step inside to a bright, open floor plan featuring updated flooring and a seamless flow between the living, dining, and kitchen areas—perfect for everyday living and entertaining. The spacious primary suite includes a private bath, while two additional bedrooms provide flexibility for guests, a home office, or hobbies. Enjoy the outdoors from the expansive back deck overlooking a peaceful setting, plus the convenience of a one-car garage and large storage shed. Tucked away from the main road, this home offers added privacy while remaining close to Route 105 and Route 44. Recent updates include a new water heater (2025) and roof and HVAC (2018). Oak Point residents enjoy exceptional amenities including heated indoor and outdoor pools, tennis, pickleball, bocce, shuffleboard, fitness center, billiards, library, and a vibrant clubhouse with year-round social events and activities. The monthly park fee includes the land lease, real estate taxes, sewer, lawn care, shrub trimming, snow removal, and trash removal, providing truly maintenance-free living so you can spend more time enjoying everything this wonderful community has to offer.

6406 Oak Point, Middleboro

Listing courtesy of Listing Agent: Jessica Fernald from Listing Office: Coldwell Banker Realty - Plymouth.

$649,900

3 Beds ⋅ 3 Baths ⋅ 73552853 MLS

Tucked away at the end of a long private driveway and surrounded by nature, this inviting home offers the perfect blend of privacy, comfort, and thoughtful updates. Step inside to a warm and welcoming living room featuring soaring cathedral ceilings with exposed beams and a classic wood-burning fireplace, creating a cozy gathering space year-round. Enjoy the outdoors from the spacious composite deck, an ideal spot for entertaining or simply relaxing while taking in the peaceful natural surroundings. Recent improvements provide peace of mind, including a brand-new septic system, new boiler, replacement windows and doors, Roth oil tank, updated gutters, and a well pump and pressure tank that are less than five years old. A heated garage adds year-round convenience and versatility for vehicles, hobbies, or additional workspace. If you're looking for a home that offers privacy, modern mechanical updates, and a beautiful setting, this Middleboro property is one you won't want to miss.

6 Daniel Dr, Middleboro

Listing courtesy of Listing Agent: Robert Chestnut from Listing Office: Keller Williams Realty.

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 73550874 MLS

Welcome to luxury living at its finest! Nestled on a quiet cul-de-sac in one of Middleboro's most desirable neighborhoods, this thoughtfully designed 4-bed, 2 full & 2 half bath home offers an exceptional blend of elegance, comfort, & entertainment. Every detail has been carefully curated, creating a home that's as functional as it is beautiful. The backyard is your own private retreat, featuring a stunning 5-foot semi-inground saltwater pool surrounded by space to relax, entertain, & create lasting memories. Inside, the possibilities continue with 4 complete levels of living, including a finished 4th-floor media room perfect for movie nights, gaming, or a private retreat. The finished lower level is an entertainer's dream, complete with a bar, lounge area, & the perfect setup for hosting friends or cheering on your favorite sports team. This is more than a home—it's a lifestyle where every space has been designed for gathering, celebrating, & making memories that will last a lifetime.

8 Paddock Cir, Middleboro

Listing courtesy of Listing Agent: Tiffany Weigold from Listing Office: Keller Williams Elite.

$450,000

3 Beds ⋅ 2 Baths ⋅ 73550717 MLS

Welcome to Oak Point, a premier 55+ community offering resort-style living and exceptional amenities. This beautifully maintained 3-bedroom, 2-bath home features a bright, open floor plan designed for comfortable everyday living and effortless entertaining. The spacious kitchen flows seamlessly into the dining and living areas, while the private primary suite offers a relaxing retreat with an en-suite bath and ample closet space. Two additional bedrooms provide flexibility for guests, hobbies, or a home office. Enjoy your morning coffee or unwind in the peaceful outdoor space. Residents of Oak Point enjoy access to a clubhouse, fitness center, swimming pools, tennis courts, walking trails, and a full calendar of social activities. Experience low-maintenance living in one of the area's most sought-after active adult communities. Land lease fee, approx $970 mo. covers taxes, lawn care, snow and trash removal and more. First showings at Open House.

307 Blueberry Circle, Middleboro

Listing courtesy of Listing Agent: Jennifer Soderquist from Listing Office: Conway - Mansfield.

$429,000

2 Beds ⋅ 2 Baths ⋅ 73550121 MLS ⋅ ['The Groves At Middleboro Village'] BLDG.

Welcome to 21 Sycamore Dr, an immaculate end-unit condo at The Groves in Middleboro offering 1,556 sq. ft. with 2 bedrooms and 1.5 baths. The main level features hardwood floors, great natural light, and an easy flow into the dining area and kitchen. The kitchen includes brand-new appliances and direct access to deck for added outdoor space. Upstairs offers two spacious bedrooms with strong closet space, including a second bedroom with a walk-in closet. The full bath features a double vanity with laundry located within the bathroom. The full basement provides storage with the opportunity to create a space that fits your needs, while the attached garage adds convenience. Features include central air, central vacuum, 200 amp electrical service, newer high-efficiency tankless boiler, plus more. Located in a desirable area near Route 44, highways, shopping, dining, and amenities, this condo offers low-maintenance living. First showings begin July 19th from 11 AM–1 PM.

21 Sycamore Dr Unit 21, Middleboro

Listing courtesy of Listing Agent: Miguel Camara from Listing Office: RE/MAX Real Estate Center.

$529,900

3 Beds ⋅ 1 Baths ⋅ 73549154 MLS

Welcome to this well-maintained 3-bedroom, 1-bath home offering 1,701 square feet of comfortable living space. Situated on a desirable corner lot, this property features a fully fenced backyard with a rear deck, a dedicated fire pit area perfect for relaxing or entertaining, and a storage shed for added convenience. Enjoy peaceful views of nearby cranberry bogs and a picturesque pond, creating a serene setting right from your own property. Inside, you'll find a functional layout designed for everyday living. Ideally located with easy access to Routes 495, 44, 105, 58, and 24, this home offers both comfort and convenience for commuters. Whether you're a first-time homebuyer, downsizing, or simply looking for a move-in-ready home, this property is one you won't want to miss.

812 Plymouth St, Middleboro

Listing courtesy of Listing Agent: David Silva from Listing Office: RE/MAX River's Edge.

$569,000

3 Beds ⋅ 2 Baths ⋅ 73548524 MLS

Welcome to 53 Wareham Street, a beautifully updated 3-bedroom, 2-full-bath home offering water views of the Nemasket River. A stunning 12' × 56' deck overlooks the river, creating the perfect setting for outdoor dining, entertaining, or simply unwinding while taking in the scenery. The beautifully landscaped grounds form a secluded oasis retreat with ample off-street parkin and an electrified storage shed ideal for hobbies, a workshop, or additional storage. Inside, timeless character blends seamlessly with modern comfort, featuring inviting living spaces and a well-appointed kitchen designed for both everyday living and effortless entertaining. Conveniently located just minutes from the vibrant town center and the commuter rail station, this exceptional property offers the perfect balance of privacy, comfort, accessibility, and natural beauty. Title V is sellers responsibility.

53 Wareham St, Middleboro

Listing courtesy of Listing Agent: Blake Starratt from Listing Office: RE/MAX Legacy.

$519,000

4 Beds ⋅ 1 Baths ⋅ 73547468 MLS

Commuters Dream less then 1/2 mile from commuter rail.... Charming and beautifully updated New England Colonial conveniently located just a short distance to all the amenities of Middleboro Center—shops, restaurants, coffee, schools, library, and commuter rail. This home blends classic charm with modern style, featuring a gorgeous kitchen with granite countertops, tile backsplash, and stainless steel appliances. Freshly painted interior, refinished hardwood floors, tile in kitchen and bath, and carpeting in bedrooms and family room. Enjoy gas heat, central air, and an updated electrical panel. The flowing floor plan offers open, airy living spaces including a finished walk-out basement with Vermont Castings gas stove and plenty of storage. The attached two-car garage connects through a spacious mudroom, and the large deck overlooks a deep, private backyard perfect for relaxing or gardening. Vinyl siding completes this move-in ready gem!

53 West St, Middleboro

Listing courtesy of Listing Agent: Shauna Fanning from Listing Office: William Raveis R.E. & Home Services.

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.