Middleboro MA 55+ Communities & Downsizing Guide
Helping adults 55+ explore 55+ communities, one-level homes, and downsizing options in Middleboro MA and surrounding South Shore towns.
Middleboro (often spelled Middleborough) is located approximately 40 miles south of Boston and offers a scenic setting with abundant open space, ponds, and conservation land. Known for its quieter pace and outdoor recreation, the town appeals to homeowners who want room to breathe while maintaining convenient access to Routes 24, 28, 44, and 495.
With commuter rail access and the Old Colony Rail Trail nearby, Middleboro combines accessibility with natural surroundings.
Looking for 55+ Communities in Middleboro MA?
Middleboro is home to four established 55+ communities offering a mix of ownership structures and housing styles. Options range from resident-owned manufactured housing communities to condominium-style townhomes and a large amenity-focused land-lease development.
Because ownership models vary significantly, understanding land-lease versus resident-owned cooperative structures is especially important when comparing options in Middleboro.
🏡 55+ Community Options in Middleboro
Middleboro’s established 55+ communities include:
• Edgeway – Resident-owned cooperative manufactured housing
• Hillcrest – Resident-owned cooperative manufactured housing
• Holly Ridge Condos – Attached townhome-style condominiums
• Oak Point – Large land-lease community with extensive amenities
These communities allow buyers to compare affordability, ownership structure, and lifestyle preferences within one town.
Community Features and Amenities
Middleboro offers one of the more diverse ownership mixes among South Shore towns.
Depending on the community, buyers may find:
Resident-owned cooperative communities
Land-lease manufactured housing
Attached townhome condominiums
One-level modular homes
Clubhouse and pool amenities (Oak Point)
Smaller-scale residential settings without clubhouse amenities (Edgeway, Hillcrest, Holly Ridge)
Oak Point is the largest 55+ community in town and offers a more amenity-rich lifestyle, including multiple pools, clubhouse facilities, and organized social activities.
Edgeway and Hillcrest provide more affordability-focused, resident-owned cooperative living.
Holly Ridge offers traditional attached condominium townhomes with full basements and exterior maintenance included.
This range gives Middleboro buyers flexibility in both budget and lifestyle.
📊Is Middleboro a Good Place To Downsize?
Middleboro may appeal to homeowners who:
Prefer a quieter, scenic setting
Want access to commuter rail
Value outdoor recreation and conservation land
Are comparing different ownership structures
Seek more affordability than some coastal South Shore towns
Because the town includes both cooperative and land-lease communities, buyers should understand how HOA structures and tax treatment differ before making a decision.
📍Compare Middleboro to Nearby Towns
Homeowners often compare Middleboro to:
Plymouth – Larger 55+ selection with more luxury and golf-oriented communities.
Wareham – Coastal-adjacent 55+ living with beach proximity.
Lakeville – Smaller inventory but rural setting.
Bridgewater – More traditional condo-style 55+ communities.
Middleboro often appeals to buyers seeking a balance of affordability, outdoor access, and ownership flexibility.
What Other Downsizing Options Exist in Middleboro?
Not every homeowner chooses age-restricted living.
Additional downsizing options in Middleboro may include:
Ranch-style single-family homes
Smaller traditional homes with first-floor bedrooms
Non-age-restricted condominiums
Homes near commuter rail access
Because Middleboro has a mix of rural and residential neighborhoods, some homeowners choose to downsize within a traditional property rather than move into an HOA-based community.
Frequently Asked Questions About 55+ Living in Middleboro
How many 55+ communities are in Middleboro MA?
Middleboro has four established 55+ communities offering cooperative, land-lease, and condominium ownership options.
Are there resident-owned communities in Middleboro?
Yes. Edgeway and Hillcrest operate as resident-owned cooperative communities.
Is Oak Point a land-lease community?
Yes. Oak Point operates as a land-lease community with amenity-focused living.
Is Middleboro a good town for retirement?
Middleboro may appeal to homeowners seeking a quieter setting with access to commuter rail, outdoor recreation, and more varied ownership models.
Important Note
Community details, pricing ranges, HOA structures, and availability may change over time. This page is intended for general informational purposes. Buyers should verify community rules, fees, and ownership details directly and conduct appropriate due diligence before making any purchase decisions.
Local Resources in Middleboro
Middleboro provides helpful local resources for 55 and older adults through the Middleborough Council on Aging and the Town of Middleborough, which many residents rely on for programs, services, and community information that support active, independent living.
What Clients Say
★ ★ ★ ★ ★
“Pam was very informative, helpful, and patient when I was frustrated. She takes the time to go over everything and makes sure you understand what will be going on.”
Jean Snow
Bought a Home in a 55+ Community, Plymouth County
★ ★ ★ ★ ★
“Pam made buying our new home and selling our current one feel smooth and manageable. She was always communicative, organized, and available, and helped keep what could have been a stressful process surprisingly painless. We highly recommend working with Pam.”
Sandy & Don
Home Seller & 55+ Buyer, Plymouth County
★ ★ ★ ★ ★
“Pam Corning is your "Go-to" realtor .She is hard-working, knowledgeable, and committed. When " bumps in the road " come up, she is there, knowing what to do . We got lucky when we hired Pam Corning. We fully recommend her to any real estate service that you need, buying and selling!”
John & Karen Boyle
Home Seller & 55+ Buyer, Plymouth County
Want to See More Options?
Sometimes the best opportunities aren’t easy to find online. My FREE printed guide provides complete, side-by-side details on every 55+ community across Plymouth County and the South Shore, including:
HOA fees and what they cover
Typical price ranges
Home styles and layouts
Age requirements
Pet rules and restrictions
Community amenities
If you’d like a copy, reach out anytime and I’ll be happy to get one to you.
📞 Call, text Pam at 508-287-8319 or fill out the contact form.
Explore All Available Homes
If you’d like to browse current homes or upcoming open houses anywhere in Massachusetts, you can explore available listings here:
👉 View Active Homes & Open Houses
Prefer a customized list based on your price range, layout, and timing? I’m happy to set that up for you so you receive new listings as they hit the market.
Local 55+ Real Estate Expertise You Can Trust
Hi, I’m Pam Corning, a REALTOR® and Seniors Real Estate Specialist (SRES®) serving Plymouth County, the South Shore, and surrounding Massachusetts communities. I help adults 55+ explore 55+ communities, single-level homes, and downsizing options that fit their next chapter.
Whether you're considering a move in Whitman, Bridgewater, Wareham, Plymouth, or nearby towns, I guide you through age-restricted neighborhoods, HOA structures, land-lease properties, and the logistics of selling before buying.
From active adult communities to probate or inherited home sales, I provide clear guidance and local expertise so your move feels informed — not overwhelming.
Let’s make your next move simple, confident, and right-sized for the life you want next.