Middleboro Homes under $500,000

Welcome to Middleboro, Massachusetts – a charming town nestled in the heart of Plymouth County, where history meets modern living. With its rich colonial past and vibrant community spirit, Middleboro offers a unique blend of small-town charm and convenient access to urban amenities. Located just a short drive from Boston and Cape Cod, this picturesque town is perfect for families, retirees, and anyone seeking a peaceful lifestyle without sacrificing connectivity.

One of the most appealing aspects of Middleboro is its diverse housing market, particularly for those looking for homes under $500,000. Here, you’ll find an array of options that cater to various tastes and budgets. From cozy single-family homes with spacious yards to charming historic properties that exude character, Middleboro has something for everyone. Many of these homes are situated in friendly neighborhoods, providing a sense of community and a welcoming atmosphere.

Residents enjoy an abundance of local parks, scenic walking trails, and recreational facilities, making it easy to embrace the great outdoors. The town's rich history is celebrated through its well-preserved landmarks and cultural events, offering residents a glimpse into its storied past. Additionally, Middleboro boasts excellent schools and a range of local shops and restaurants, ensuring that everything you need is just a stone's throw away.

If you’re searching for an affordable home in a friendly and vibrant community, Middleboro is the perfect place to call home. Discover the charm and opportunities that await you in this delightful Massachusetts town!

Newest Middleboro Homes under $500,000

$399,900

3 Beds ⋅ 2 Baths ⋅ 73584922 MLS

**COMING SOON** Newly updated 3BR/2BA Princeton-style home in the desirable Oak Point Community. If you are looking for a move-in ready "pottery barn styled" unit in close proximity to the club house, you won't want to miss this one! The many updates include; all new flooring, new plumbing with walk-in shower, new stainless steel appliances with gas stove for cooking, updated plumbing and vanity in master bathroom, new hot water heater (2023), new heat pump/central air system (2023), and new roof (2024). Along with a 3 season porch and a one car attached garage, you could be in for the Holidays. All appliances included. Please note: Oak Point is a 55+ Community with many amenities including heated indoor and outdoor pools, tennis courts, bocce courts, shuffleboard, billiard room, gym and library. The Oak Point 55+ park fee includes land lease, taxes, sewer, snow removal, trash removal, lawn care and shrub trimming. Professional photography to be added to listing in the coming days. Open House weekend, Oct. 10th & 11th.

701 Oak Point Drive, Middleboro

Listing courtesy of Listing Agent: Diana Saunders Martin from Listing Office: Martin Real Estate.

$499,000

3 Beds ⋅ 2 Baths ⋅ 73580094 MLS

Welcome to this charming home that blends character with everyday convenience. Offering 3 bedrooms and 1.5 baths, this inviting property features high ceilings, large windows, crown molding, and a kitchen bay window that fills the space with natural light. Major updates include a new boiler in 2025, new roof in 2026 and exterior painting. The fully fenced backyard is a standout feature, offering a private outdoor retreat with an expansive paver patio and plenty of room to relax or entertain. Enjoy outdoor dining, gardening, or a secure space for pets to play. Conveniently located near the center of town, you’ll be close to Middleboro’s restaurants, shopping, and everyday amenities, with access to major routes and commuter rail options. Enjoy historic charm, exceptional outdoor living space, and a location that makes daily life easy. A lovely place to live.

174 Center Avenue, Middleboro

Listing courtesy of Listing Agent: Tara Lynn Bazarewsky from Listing Office: Conway - Wareham.

$399,000

2 Beds ⋅ 2 Baths ⋅ 73580204 MLS

Welcome to Ashley Place! This is a move in ready townhouse style unit waiting for you to enjoy the Fall and upcoming holidays. Enter from the farmer's porch to the bright entry way with cathedral ceiling and skylight and a half bath. Step into the sunken living room with a beautiful fireplace with arched windows on either side, overlooking a tree lined outside areas. With the open floor plan you have a dining room with a view of the back deck from the slider. The kitchen was remodeled with beautiful cabinetry and tile backsplash and stone countertops and a space for a table. Upstairs you have a spacious main bedroom with a remodeled bathroom with a double sink and marble counter top. You have two large closets to finish the space. There is a second bedroom on the second floor as well. Walk downstairs to the partially finished basement perfect for parties, playroom, gym, office, etc. There is lots of storage and the washer and dryer have their own space. Water heater was replaced in December 2025. Convenient & Close to Highways(28, 105, 495 & 24), Schools, Close to the New Middleboro Commuter Rail! Middleboro has their own gas and electric municipalities for your convenience.

33 Ashley Ln Unit 33, Middleboro

Listing courtesy of Listing Agent: Cindi Ford from Listing Office: RE/MAX Platinum.

$359,000

3 Beds ⋅ 2 Baths ⋅ 73579900 MLS

Oak Point - One of the South Shore's premier 55+ communities! Designed for those that embrace an active and social lifestyle. This vibrant neighborhood offers a true sense of community and resort style amenities including three pools, tennis, pickleball, bocce, a library, billiard room, fitness center and much more. HOA fee covers sewer, trash removal, lawn care and snow removal - plus no real estate taxes! This Home offers a solid value for someone and is being sold as-is. Seller has never lived in the property. Don't miss this opportunity!

412 Green St., Middleboro

Listing courtesy of Listing Agent: Carl Djusberg from Listing Office: Djust Realty.

$425,000

3 Beds ⋅ 2 Baths ⋅ 73576033 MLS ⋅ ['Plymouth Street Condominiums'] BLDG.

SAVE $$$ with no CONDO FEES! Title V passed. Welcome to this well cared for duplex offering three levels, including walk out basement to gorgeous fenced back yard. The first floor includes updated kitchen ( granite, stainless steel appliances and beautiful cabinetry), eat-in dining area, spacious family room and 1/2 bath. Second level has three bedrooms (main bedroom with walk in closet) and full bath. Your walk out basement ( you may finish) leads to great yard for relaxation and entertainment. Off street parking and front porch. Convenient to amenities including short distance to Public T Station. Call to view this special home. OPEN HOUSE SATURDAY 10/3 2:00 - 4:00.

581 Plymouth St Unit 581, Middleboro

Listing courtesy of Listing Agent: Joanne Mecke from Listing Office: Conway - Mattapoisett.

$399,900

2 Beds ⋅ 2 Baths ⋅ 73575395 MLS

Motivated Seller!! Two bedroom Single Level Style End Unit Condo situated in a bucolic setting of over 35 acres offering a quiet country retreat yet just minutes from shopping, dining and the Middleboro Commuter rail. 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 gas 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 2nd 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.New HVAC, Harvey Windows, Deck, Patio, Kitchen, and Italian Tile Floor all completed in the past 6 years.Economical heat & a.c. through Middleboro Gas & Electric, a municipality owned public utility Co. Once you step in and see this condo, you will not want to leave!

151 Ashley Lane Unit 151, Middleboro

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

$396,900

2 Beds ⋅ 2 Baths ⋅ 73573193 MLS ⋅ ['ashley Place'] BLDG.

Newly Priced!/SUNDAY OPEN HOUSE 11-12:30pm/SOUGHT After "Ashley Place" Condominium/Stylish "Barrington" Townhouse Style w/Superb Architectural Features(Cathedral Ceiling, Moldings, Skylight, Sunken Livingroom)Situated on a Beautiful 35 Acre "Park Like" Setting/Front-Covered Farmer's Porch/Gleaming WOOD Flooring Thru Out(Downstairs(Livingroom & Dining Room)& Upstairs(Stairs, Hall & Bedroom(s)/Tiled Foyer(Skylight, Plant Shelf, 16'2" CATHEDRAL Ceiling)/BRIGHT & OPEN Floor Plan w/SUNKEN Living Room(Wood Burning Fireplace)& Dining Area Leading to 14'x12' Deck That Overlooks PRIVATE Wooded Area/Kitchen(Eat-In)w/Tiled Flooring/SPACIOUS Master w/Closeted Dressing Area/FULL Basement w/Finished Room-Separate Laundry Room/Town Water, GAS(Gas Heat) & Municipal Electric(Middleborough Gas & Electric)/CENTRAL AIR/Superb Commuting Location-Convenient & Close to Highways(28, 105, 495 & 24), Schools, Downtown Amenities(Post, Library, Cafe)& Under 4 Miles to the New Middleborough Commuter Rail!

163 Ashley Lane Unit 163, Middleboro

Listing courtesy of Listing Agent: Kyle Belken from Listing Office: Realty One Group, LLC.

$264,900

1 Beds ⋅ 1 Baths ⋅ 73573114 MLS ⋅ ['38-40 School Street Condominium'] BLDG.

Welcome to Downtown Living offering a beautiful blend of Historic Charm and Modern conveniences of nearby Restaurants, Shopping, Repair shops, Clubs, Churches, Salons etc. This 7 Unit condo complex is Owner Occupied and Renovated just 3 Years ago. Super easy to have your own entrance! The interior is Bright with Tasteful Updates to all rooms, The Extra Laundry/ Pantry Space is a real Plus to the Kitchen area. The Kitchen offers stainless appliances and Granite tops for a modern culinary Look. The Full Bath is Clean, Bright w/ a Granite top Vanity. A smaller area just off Kitchen can be used as Walk-in Closet/ or Office area w/ outside egress.. This 1st Floor- Garden Style Unit has a Beautiful Covered Welcome Porch to Enjoy Peace and Relaxation. The Condo has assigned Parking. Easy access to Rts 44 & 105,and18/28 and Near by T Station . A Great Starter Home OR Just a wonderful opportunity for the Downsizer! Don't Pay Rent, when you can Own this lovely Gem!

38-40 School St Unit 40-2, Middleboro

Listing courtesy of Listing Agent: Karen M. Pettenati from Listing Office: Fathom Realty MA.

$429,900

2 Beds ⋅ 2 Baths ⋅ 73568487 MLS ⋅ ['The Groves'] BLDG.

Welcome to easy townhouse living at The Groves in Middleboro! This inviting home offers a bright, open layout with laminate flooring and comfortable living spaces designed for everyday living and entertaining. The spacious kitchen features abundant cabinetry, stainless steel appliances, gas cooking, and a breakfast bar overlooking the living area. Upstairs, generously sized bedrooms offer plenty of flexibility, including a spacious primary bedroom. Enjoy the convenience of gas heat, central air, an attached garage, and a full basement providing excellent storage and additional possibilities. Step outside to a private deck overlooking a nicely maintained green space—perfect for relaxing or dining outdoors. With a welcoming front porch, attractive landscaping, and a convenient location close to shopping, dining, commuter routes, and area amenities, this well-kept townhouse is ready to welcome you home.

7 Sycamore Dr Unit 7, Middleboro

Listing courtesy of Listing Agent: James OBrien from Listing Office: Keller Williams Realty.

$489,900

3 Beds ⋅ 2 Baths ⋅ 73562674 MLS

Welcome to 10 Sumner Avenue, a classic Colonial-style home ideally situated on a quarter-acre lot in one of Middleborough's established neighborhoods. Built in 1900, this 3-bedroom, 1.5-bath residence offers approximately 1,294 square feet of living space, blending timeless character with everyday convenience. Located on a dead end St. this property features a spacious eat in Kitchen, Living room with pellet stove. There is a dog kennel and shed on property. The home is conveniently located just minutes from downtown Middleborough, where you'll find local restaurants, coffee shops, shopping, medical facilities, commuter rail and everyday services. Outdoor enthusiasts will appreciate nearby town parks, playgrounds, athletic fields, walking trails, and recreational facilities, providing year-round opportunities for sports, fitness, and family activities. This home is ready for its next owner to make it their own. Located close to rt. 495.

10 Sumner Ave, Middleboro

Listing courtesy of Listing Agent: Richard Wertz from Listing Office: Keller Williams Realty.

$399,900

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

MOTIVATED SELLER!! Two bedroom single level style end unit condo situated in a bucolic setting of over 35 acres offering a quiet country retreat yet just minutes from shopping, dining & the Middleboro Commuter rail.The main level displays hardwood floors, an elegant Italian tile foyer, Hunter Douglas window treatments & designer light fixtures. The kitchen is smartly designed with new custom cabinetry, granite countertops and new appliances. The light-filled dining area flows into a spacious living room with sky lights, a gas 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 2nd 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. New HVAC, Harvey Windows, Deck, Patio, Kitchen and Italian Tile Floor all completed in the past 6 years.Economical heat & a.c. through Middleboro Gas & Electric, a municipally owned public utility Co. Once you step in and see this home, you will not want to leave!

151 Ashley Lane Unit 151, Middleboro

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

$379,000

3 Beds ⋅ 2 Baths ⋅ 73556084 MLS

OPEN HOUSE CANCELED - ACCEPTED OFFER! Desirable Oak Point 55+ Community! Immediate Occupancy available! Move right into this bright and inviting Princeton-style home featuring a popular split-bedroom floor plan for added privacy. The spacious primary suite offers two closets and a private bath with a step-in shower. The open living and dining rooms provide an ideal space for everyday living and entertaining, while the kitchen features abundant cabinetry, updated stainless steel appliances, and a sunny morning room. Relax in the screened porch with wood flooring, perfect for morning coffee or evening gatherings. Two additional bedrooms and a full bath offer flexibility for guests, a home office, or hobby space (virtually staged). Built in 2003 and nicely situated on the lot, this home has been thoughtfully updated with a new refrigerator and stove (2026), furnace and central air (2022), roof (2016), and LeafGuard gutters. Additional features include Pergo flooring in the main living areas, vinyl flooring in the kitchen and baths, no wall-to-wall carpeting, and a one-car garage. Enjoy Oak Point’s exceptional resort-style amenities, including three swimming pools, tennis, pickleball, bocce, fitness center, ballroom, library, clubs, and countless social activities. The monthly fee includes lawn care, snow removal, trash pickup, sewer treatment, and access to all community amenities.

408 Green Street, Middleboro

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

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