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Middleboro MA Real Estate for Sale with Virtual Tours

Explore Middleboro, Massachusetts real estate for sale with virtual tours that offer a streamlined way to review available properties. The area features a mix of single-family homes, newer developments, and properties with convenient access to major routes and commuter rail service. Virtual tours provide a detailed look at layouts, interior finishes, and key property features to help guide your search. Browse current listings and stay up to date on real estate opportunities throughout the Middleboro area.

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31 Pine Street Middleboro MA 02346

Middleboro, MA31 Pine Street

Price$750,000

Est. Mortgage: $/month

MLS Number 73556157

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,408

Welcome home to the sought-after Whispering Pines community! This beautifully maintained 3-bedroom, 2.5-bath home offers the perfect combination of comfort, privacy, and functionality. Relax on the charming farmer's porch and enjoy the peaceful wooded setting that provides exceptional privacy in both the front and back of the property. Inside, the sun-filled first floor is filled with natural light and features a spacious, open flow between the living room, kitchen, and dining area, making it ideal for everyday living and entertaining. A convenient first-floor laundry room and half bath add to the home's thoughtful layout. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite, along with two full bathrooms. Step outside to a fully fenced backyard complete with an above-ground pool, perfect for summer gatherings or quiet evenings at home. Additional highlights include a new boiler and hot water heater (both approximately one year old), attic storage above the attached garage, and a private well and water conditioning system. Conveniently located near local amenities while offering the tranquility of a desirable neighborhood, this home is ready for its next owners!

Listed by Beatrice Murphy of Lamacchia Realty,Inc.

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$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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8 Paddock Circle Middleboro MA 02346

Middleboro, MA8 Paddock Circle

Price$1,100,000

Est. Mortgage: $/month

MLS Number 73550874

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 4,290

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.

Listed by Tiffany Weigold of Keller Williams Elite

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%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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53 Wareham Street Middleboro MA 02346

Middleboro, MA53 Wareham Street

Price$569,000

Est. Mortgage: $/month

Contingent

MLS Number 73548524

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,539

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.

Listed by Blake Starratt of RE/MAX Legacy

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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49 Plain Street Middleboro MA 02346

Middleboro, MA49 Plain Street

Price$799,900

Est. Mortgage: $/month

Contingent

MLS Number 73545512

  • Residential
  • Bedrooms 3
  • Bathroom 3
  • Square Feet 2,486

Come home to a setting that feels like your own private retreat. Set on nearly 2 wooded acres, this custom Cape welcomes you with a bright, inviting foyer that opens to beautifully connected living spaces designed for both everyday comfort and effortless entertaining. The stunning living room, anchored by a striking stone fireplace, flows seamlessly into a spacious kitchen featuring granite countertops, ample cabinetry, and an open dining area where family and friends naturally gather. A sunroom invites quiet mornings with coffee, while the composite deck overlooks a backyard made for summer, complete with an above-ground pool, gardens, and room to unwind. Upstairs, the expansive primary suite is a true escape with a private balcony, walk-in closet, and spa-like bath with a whirlpool tub. Hardwood floors, generous room sizes, three full baths, a 2-car garage complete a home that offers the space, warmth, and lifestyle buyers have been searching for.

Listed by Janine Wuschke of Keller Williams Realty

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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233 Tispaquin Street Middleboro MA 02346

Middleboro, MA233 Tispaquin Street

Price$789,000

Est. Mortgage: $/month

MLS Number 73541081

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 2,184

EASY TO SHOW and will include a NEW Septic! This 7.7-acre private retreat, offers privacy, nature, and convenience in the middle of the South Shore. The flexible floor plan hosts a first floor large living room with fireplace, bonus room with patio access, laundry room, and a bright sunroom/office with garage and patio access. Upstairs offers 3 bedrooms and 2 full baths, including a primary suite, eat-in kitchen with stainless appliances and deck access, and a dining/living room option. This well-maintained home features updates, including the roof, water heater, well pump, water filtration, stone wall, granite countertops, finished walls/ceiling in garage, 3.25" hardwood floors upstairs and engineered wood & tile downstairs. Enjoy 3 mini-splits with heat pumps, propane heat and gas stove. Additional features oversized garage door with pull-down loft storage with 2 windows, added carport, shed, French drains, generator hookup, ADU potential on first floor or separately on the property and many outdoor areas. Check out the video!

Listed by Nicole DeBenedictis of Homistic Real Estate Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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81 Rocky Meadow Street Middleboro MA 02346
Open House

MLS Number 73538098

  • Residential
  • Next Open House: Thu 08/6 5:30 pm. to 7:00 pm.
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 2,007

Back on the market with a BRAND-NEW Goodman high efficiency central heat pump with central air conditioning system installed in July 2026!, This unique two-level, 4-bedroom, 2.5-bath home offers tranquility and flexible living space on both levels and sits on approximately 1.45 acres of beautiful grounds! The upper-level features three freshly painted bedrooms with brand-new flooring, a full bath, and a cozy office nook. The main level showcases soaring cathedral ceilings and a pellet stove in the living room, a spacious kitchen, an adjacent room for a walk-in pantry or storage, a separate laundry room, and a renovated primary suite with en-suite bathroom. You will love relaxing in the extra-large four-season room with vaulted ceilings! The oversized two-car garage with a full second level offers endless possibilities for hobbies or workspace. The property includes Lot 6 (see engineer's plans), which may offer future use opportunities, subject to buyer due diligence and approvals. With a new roof (2025), hot water heater (2026) and brand-new heat pump with central air, you will have peace of mind for years to come!

Listed by Julie Etter Team and Geeta McGrath of Berkshire Hathaway HomeServices Evolution Properties

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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4 Star Avenue Middleboro MA 02346

Middleboro, MA4 Star Avenue

Price$599,800

Est. Mortgage: $/month

MLS Number 73537865

  • Residential
  • Bedrooms 4
  • Bathroom 2
  • Square Feet 2,240

WOW! Incredible new low price for this cant miss property. Open House Sunday, 7/26 12-1:30. Opportunity, functionality, and charm come together in a move-in ready package. This versatile home offers flexible living spaces to fit a variety of lifestyles. A home office with its own separate entrances presents exciting possibilities for a home business, guest space, or potential ADU conversion. Inside, you'll find stunning wide-plank wood floors, a formal living room, formal dining room, family room/playroom, first-floor laundry, and a spacious kitchen with room for an eat-in nook. Upstairs are 4 bedrooms, one of which has been transformed into an impressive walk-in closet. The primary has vaulted ceilings and skylight, plus a separate stairwell from the first floor for added privacy. Comfort and efficiency are a focus with a gas stove, three-zone Energy Star Instinct heating system, and two ductless mini-splits. The oversized garage has a wood-stove and offers the perfect space for hobbies or storage. Easy access to commuter rail, shopping, dining, parks, library + more!

Listed by Andrew Romano of Bold Real Estate Inc.

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$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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5604 Oak Point Drive Middleboro MA 02346

Middleboro, MA5604 Oak Point Drive

Price$465,000

Est. Mortgage: $/month

Contingent

MLS Number 73530629

  • Residential
  • Bedrooms 3
  • Bathroom 2
  • Square Feet 1,612

Welcome to 5604 Oak Point Drive, Middleboro MA 02346 - This 55+ community has so much to offer such as multiple pools, putting green, tennis, huge club house with something for everyone. I was so very impressed by all the activities that are offered. Pool Tables, Bingo, Ballroom, Fitness center, basketball and I could go on!!! I have spoken with many owners there and they love it here. It's time to kick off your shoes and relax in a low maintenance way of living. This 3 bed, 2 bath, 2 car garage with a newer add on addition perfect for reading, relaxing, or enjoying your morning coffee or for entertaining. If you have been looking for something just like this, 5604 Oak Point Drive is the one for you...

Listed by Fern Langella of The Firm

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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287 Wareham Middleboro MA 02346

Middleboro, MA287 Wareham

Price$780,000

Est. Mortgage: $/month

Under Agreement

MLS Number 73511717

  • Residential
  • Bedrooms 4
  • Bathroom 3
  • Square Feet 1,768
  • High School Middleboro High

This 2024 NEW Build, 4 Bed, 3 Bath Colonial offers Quality construction on 1.38-acres among new homes. Bright with a modern color palette and 3.25” Oak Hardwood floors BOTH floors. The main-level features a living area Open to eat-in kitchen with granite counters, large island, white cabinets, stainless appliances and modern fixtures. Sliders lead to a composite deck, manicured lawn and wooded views. First floor hosts a 4TH Bedroom OR use as office/formal dining/playroom, laundry/pantry, garage entry and Bathroom w/shower. Upstairs find 2-Bedrooms, 2nd Bathroom and 3rd Bed/Primary Suite with 3rd Bath and 2 walk-in closets. More Highlights: shaker vanities/granite in Bathrooms, insulated basement w/2 full-sized windows and interior/exterior access stairways, pull-down attic, attached ~600SF 2-car garage with finished ceiling/walls, vinyl siding, 2-zone heat/AC, 200-AMP, 4-Bed septic, irrigation, & on-demand hot water. Minutes to downtown Middleboro, I-495, Rte.44 and New Train Station.

Listed by Nicole DeBenedictis of Homistic Real Estate Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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65 Oak Street Middleboro MA 02346

Middleboro, MA65 Oak Street

Price$639,900

Est. Mortgage: $/month

MLS Number 73514466

  • MultiFamily
  • Bedrooms 7
  • Bathroom 2
  • Square Feet 2,214
  • Parking Spaces 4

Well-maintained two-family in the heart of Middleboro offering strong rental income and major updates throughout. Second floor will be delivered vacant, first floor TAW. Each unit features 3 bedrooms, 1 full bath, an eat-in kitchen, and spacious living room. Many big-ticket improvements completed in 2022 including new electrical, all new plumbing, new roof, new siding, rebuilt exterior porches, new gutters, motion-detection lighting in common areas, new furnace for Unit 1, and new exterior doors. Full basement includes coin-op washer & dryer or separate washer/dryer hookups for each unit. Great opportunity for investors or owner-occupants seeking income potential in a convenient in-town location.

Listed by Chelsea McLaughlin and Kade Phillips of RE/MAX Legacy

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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6802 Oak Point Drive Middleboro MA 02346

Middleboro, MA6802 Oak Point Drive

Price$425,000

Est. Mortgage: $/month

Under Agreement

MLS Number 73510435

  • Residential
  • Bedrooms 2
  • Bathroom 2
  • Square Feet 1,674

Welcome to easy living at Oak Point.This bright and sunny 2-bedroom home at 6802 Oak Point Drive has been freshly painted and is ready for its next chapter. The interior offers a clean, inviting feel with natural light pouring in, creating a warm and comfortable space you'll actually want to spend time in. Located in the sought-after Oak Point 55+ community, this home is all about lifestyle. Residents enjoy a relaxed, low-maintenance way of living with access to exceptional amenities, including multiple pools, tennis courts, a clubhouse, fitness center, and a full calendar of social activities. Whether you're looking to stay active or just kick back and enjoy the surroundings, it's all right here.If you've been waiting for a simple, turnkey home in a vibrant community where everything is taken care of, this is it.

Listed by Marni Migliaccio of The Firm - Duxbury

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

357 Wareham Street Middleboro MA 02346

Middleboro, MA357 Wareham Street

Price$949,000

Est. Mortgage: $/month

Under Agreement

MLS Number 73505593

  • Residential
  • Bedrooms 4
  • Bathroom 4
  • Square Feet 2,520

The "Investor's Dream" -Rare Development Opportunity or Live/Work Estate in Middleboro! Unlock the massive potential of 357 Wareham St... Situated on a sprawling 2.62-acre level lot, this property is a goldmine for developers, entrepreneurs, or those seeking a multi-generational compound! The site features a beautifully updated 4-bedroom, 3.5-bathroom Colonial (full interior remodel by the amazing re:fab!) boasting over 2,500 sq. ft. of living space. Inside, you'll find a beautiful kitchen, both a first-floor and second-floor primary suite, both complete with a gorgeous 3/4 bath with huge walk-in showers (YES, TWO PRIMARY BEDROOM SUITES!!)! The Real Value: Development Potential: Conceptual plans are attached for THREE HOMES and THREE TWO CAR GARAGES! Seller is providing a conceptual plan for you to complete this project. See attached conceptual plan. Commercial Use: Zoning allows for unique "live-where-you-work" opportunities. Run your business right from home with so many options!

Listed by Cindy Brouwer of Cindy Brouwer Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.66% last updated on Jul 30, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. (MLSPIN) from third party sources, including sellers, lessors and public records, and were compiled by MLSPIN. 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 or leasing 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 or leasing. MLSPIN 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.

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