Refine Search
Map
Sort by
103 Orchard Ct, Middleboro
$465,000
3 Beds ⋅ 2 Baths ⋅ 73493333 MLS
Welcome home! This beautifully maintained, single level ranch is turnkey and ready for you to move in, no updates needed. Bright, comfortable, and thoughtfully updated, it blends classic charm with modern conveniences. Primary en-suite w/double sink and walk-in shower tiled floors, stylish updated finishes. 2nd full bath with tub/shower and tile floor. Newer HVAC, 30 year roof, updated kitchen appliances, including washer & dryer, worry-free systems you can trust. Hardwood floors add warmth and timeless appeal. Add to this a glass surround four season room perfect for morning coffee, reading or relaxing year round. Pride of ownership shows in every room; move in and enjoy today.. A two-car garage provides ample storage and workspace. Enjoy resort-style living with Oak Point’s exceptional amenities—two pools, bocce court, fitness center, clubhouse, and a wide variety of social programs and activities. Seller looking for May 18th closing. Oak Point Over 55

103 Orchard Ct, Middleboro

Listing courtesy of Listing Agent: Stephen Damon from Listing Office: Conway - Bridgewater.
806 Waverly Street, Middleboro
$461,000
3 Beds ⋅ 2 Baths ⋅ 73449512 MLS
Welcome to this beautifully maintained single-level Carlisle Ranch, tucked in the sought-after Oak Point 55+ community of Middleborough—one of Massachusetts’ largest and most vibrant active-adult neighborhoods. This open-concept modular home is filled with natural light and offers three bedrooms, two full baths, and easy one-floor living. Interior features Cherry cabinets, stone countertops & SS appliances. Master En Suite, bonus sunroom and convenient private lot. Enjoy beautifully landscaped gardens and resort-style amenities: an expansive clubhouse with ballroom, fitness center, basketball court, multiple pools, and tennis/pickleball courts. Join neighbors for regular activities planned by the on-site director. Oak Point brings everything to you, and when you’re ready to explore, Boston, Cape Cod, and Providence are just a short drive away. Closer to home, stroll the Cranberry Harvest Trail or picnic by the Nemasket River.

806 Waverly Street, Middleboro

Listing courtesy of Listing Agent: Marilyn & Company from Listing Office: Keller Williams Realty Boston South West.
4402 Pheasant Ln, Middleboro
$445,000
2 Beds ⋅ 2 Baths ⋅ 73534416 MLS
Welcome to the highly desirable Oak Point Community. This beautifully maintained home features an open concept floor plan that is ideal for entertaining, with gorgeous hardwood floors and a gas fireplace. The spacious kitchen has all new appliances and has plenty of storage with a cozy dining area complete with a built in bench seat. The dining room opens to a front sitting area and larger family room which provides access to a 3 season room with a pellet stove. The primary bedroom features a large private bathroom with all new fixtures and a walk in closet. The other bedroom is bright and spacious with a full bathroom nearby. The home offers a 1 car garage with a large storage area attached. It has a newer heating system, newer roof and a new hot water heater, and. a NEW whole house GENERATOR. The front entrance is new with vinyl and Trex decking. There are many amenities, such as bocce, pickleball, tennis, billiards, workout gym, an indoor pool and 2 outdoor pools, and much more.

4402 Pheasant Ln, Middleboro

Listing courtesy of Listing Agent: Robert Murphy from Listing Office: Realty Choice, Inc..
2602 Pheasant, Middleboro
$440,000
3 Beds ⋅ 2 Baths ⋅ 73451128 MLS
A fresh opportunity to enjoy low-maintenance living in one of the areas most active 55+ communities. This Princeton Grand model offers a flexible and spacious layout with 3 bedrooms, 2 full baths, a family room with gas fireplace, and a bright 4-season sunroom that provides valuable extra living space year-round. Hardwood floors enhance the main living areas and primary bedroom, while new carpet in the living room, guest bedrooms and family room (2025) gives the home a refreshed feel. The kitchen features a pantry and easy flow for everyday living or entertaining. The primary suite includes an oversized bath and a recently upgraded walk-in shower. Additional highlights include a 2-car garage, new composite front and back decks (2025), roof (2015), and HVAC system and water heater (2016). Residents enjoy access to pools, tennis courts, a fitness center, and a clubhouse with a full calendar of social activities — offering an easy, connected lifestyle in a welcoming neighborhood

2602 Pheasant, Middleboro

Listing courtesy of Listing Agent: Sandy Andersen from Listing Office: The Real Estate Collaborative.
6802 Oak Point Drive, Middleboro
$425,000
2 Beds ⋅ 2 Baths ⋅ 73510435 MLS
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.

6802 Oak Point Drive, Middleboro

Listing courtesy of Listing Agent: Marni Migliaccio from Listing Office: The Firm - Duxbury.
2006 Green St., Middleboro
$425,000
3 Beds ⋅ 2 Baths ⋅ 73508231 MLS
Welcome to Oak Point in Middleboro, one of the area's premier 55+ lifestyle communities where resort-style living meets everyday comfort. This vibrant, pet-friendly community offers a full social calendar & exceptional amenities including multiple pools/fitness center/tennis & pickleball courts & a lively clubhouse filled w/ events & activities. Enjoy true maintenance-free living w/ landscaping, snow/trash removal included, plus no property taxes! This freshly painted home offers over 1,400 sf of single-level living w/ gleaming hardwood floors throughout & abundant natural light. The thoughtful layout features a spacious primary suite w/ walk-in closet, en suite bath w/ whirlpool tub & step-in shower. The fully applianced kitchen includes an island & pantry & flows seamlessly into the main living areas. Additional highlights include a 2-car garage w/ loft storage, laundry room w/ washer/dryer/utility sink & a relaxing 3-season screened porch. A home & lifestyle not to be missed.

2006 Green St., Middleboro

Listing courtesy of Listing Agent: David Michael from Listing Office: Conway - Lakeville.
6406 Oak Point, Middleboro
$420,000
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.
1606 Fox Run, Middleboro
$420,000
2 Beds ⋅ 2 Baths ⋅ 73423256 MLS
Welcome to Oak Point, a premier 55+ community for active adults. This well-maintained, one-owner Buckingham-style home is full of light and brightness, move-in ready, full of character, and just 1/4 mile from the clubhouse on a quiet street. Featuring 7 spacious rooms, 2 bedrooms, 2 full baths, and a 1-car garage with extra storage space. The open layout includes a traditional mantled gas fireplace in the formal living room, flowing into the dining area with sliders to a serene screened-in deck perfect for enjoying morning coffee or evening breezes. Enjoy a cozy den, country kitchen, and birdwatching from the den’s picture window overlooking an evergreen-lined rear border. Upgrades include extended home length, front portico, and den. Recent updates (2023–2025) include new roof w/ 5 new skylights, modern heating & AC system, integrated Ring security system, and microwave. Resort-style living awaits … don’t miss this opportunity to join the vibrant Oak Point community.

1606 Fox Run, Middleboro

Listing courtesy of Listing Agent: Penny Quackenbush from Listing Office: Keller Williams Elite.
5604 Oak Point Drive, Middleboro
$415,000
3 Beds ⋅ 2 Baths ⋅ 73530629 MLS
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...

5604 Oak Point Drive, Middleboro

Listing courtesy of Listing Agent: Fern Langella from Listing Office: The Firm.
3905 Pheasant Lane, Middleboro
$415,000
2 Beds ⋅ 2 Baths ⋅ 73455279 MLS
A setback lot and extended driveway offer privacy with a tranquil setting for outdoor living, abutting the natural wood line, plenty of off-street parking for guests. Many closets throughout, A sprawling ranch layout with many rooms and options, open sitting room and dining room as you come in, leading to an open spacious kitchen and second sitting room or optional additional dining area with gas fireplace and beautiful built-ins on either side and the side entrance out to the 2 car-garage. Beyond the kitchen is a cozy family room with a second gas fireplace, leading to attached screen porch and exterior deck and patio. Down the hallway you'll find the separate laundry room, first full bathroom and two spacious bedrooms including the main bedroom at the end of the house with 2 walk-in closets and ensuite bathroom with double vanity, soaking tub and stand up shower. Oak Point has a full-time social director, library, billiards, fitness ctr, bocce, cornhole, ballroom, gym, live music.

3905 Pheasant Lane, Middleboro

Listing courtesy of Listing Agent: Colleen Fiumara from Listing Office: Owlhouse Realty Co..
503 Hastings Road, Middleboro
$380,000
2 Beds ⋅ 2 Baths ⋅ 73459746 MLS
Nestled at 503 Hastings Road, Middleboro, MA, this single-family residence offers an inviting home, ready to move in and start creating memories. Featuring multiple upgrades, this home has appliances that are 2 years old including the refrigerator, dishwasher, washer & dryer. The roof and (outdoor) HVAC are 3 years old. The HVAC system is exceptionally quiet, a desired feature highly desired in Oak Point. Wood floors are spread throughout the home providing a warm and attractive feeling. The formal living room is spacious with formal dining at one end and the kitchen/family room features a stone, ceiling height gas fireplace for the most comfortable winter evenings. The floating kitchen island is the perfect spot for casual meals and warm breakfast coffee. This home has 2 large bedrooms with the Master featuring 2 walk-in closets and a large private bath. The screened porch nestles up to the woods providing a unique opportunity to commiserate with nature. All-in-all, a very nice home.

503 Hastings Road, Middleboro

Listing courtesy of Listing Agent: Keith Bettencourt from Listing Office: Keller Williams Realty Colonial Partners.
2602 Green St, Middleboro
$359,000
2 Beds ⋅ 2 Baths ⋅ 73545248 MLS
Beautiful Sudbury-style home in the desirable 55+ Oak Point community. The open floor plan is perfect for entertaining, featuring bright sunlit rooms and a spacious family room with a gas fireplace open to the living and dining areas. Sliders lead to a private deck for relaxing or gatherings. The cheerful kitchen includes a windowed breakfast nook. The large main bedroom offers a walk-in closet, ceiling fan, and private bath with a walk-in shower. The second bedroom also has a walk-in closet and ceiling fan. 2nd bath with tub/shower. NEW FLOORS, newer heating/AC and hot water heater. A two-car garage provides ample storage and workspace. Enjoy resort-style living with Oak Point’s exceptional amenities; Two pools, bocce court, fitness center, clubhouse, and a wide variety of social programs and activities.

2602 Green St, Middleboro

Listing courtesy of Listing Agent: Stephen Damon from Listing Office: Conway - Bridgewater.
406 Simmons Rd, Middleboro
$355,000
3 Beds ⋅ 2 Baths ⋅ 73565367 MLS
Affordable & Adorable in popular Oak Point! 55+ Community, this Chatham style manufactured home is value-priced with so many amenities, including clubhouse/,pools/, (indoor and outdoor), tennis/billiards/bocce/basketball/pickleball, and so much more! Furnace and central air 2022, newer roof, Main Bedroom with big walk-in closet and private bath, 2 additional bedrooms and another full bath, a comfy family room, sitting room, and sliders to screened-in porch. Laundry is located off the eat-in kitchen. This home works if you desire prIvacy or a stroll to the clubhouse and enjoy all the activities every season. Proximity is 8 miles to a grocery store or have them delivered, 44 miles to Boston, and 42 miles to Providence. Missing the historic Plymouth Beach? No worry- 16 miles and only 13 miles to medical facilities. This truly is a fabulous lifestyle! HOA is.($976.19) covers trash removal, snow, irrigation, real estate taxes, landscaping, septic and more. Seller has never lived in the property and it is being sold "as is". 56x27 ANY AND ALL OFFERS DUE 8PM ON 8/20 Seller will need at least 6-8 hours to reply as traveling out of country. DO NOT USE DEADBOLT

406 Simmons Rd, Middleboro

Listing courtesy of Listing Agent: Pamela Vigneau from Listing Office: The Firm.
3305 Island Drive, Middleboro
$325,000
3 Beds ⋅ 2 Baths ⋅ 73507407 MLS
OPEN HOUSE CANCELLED! Offer accepted. Oak Point - One of the South Shore’s premier 55+ communities! Designed for those who embrace an active & social lifestyle. This vibrant neighborhood offers resort-style amenities and a true sense of community. This well-maintained Princeton style 3-bedroom, 2-bath home boasts 1,344 sq. ft. of thoughtfully designed living space, ideal for both everyday comfort & entertaining. Step inside to find a bright, open layout with updated flooring and a seamless flow between the living, dining & kitchen areas. The enclosed porch provides a perfect seasonal retreat. The spacious primary suite features a private bath, while additional living space offers flexibility for guests or hobbies. Residents enjoy access to multiple pools, tennis, pickleball, bocce, fitness center, and a lively clubhouse filled with social events and activities. Maintenance-free living including landscaping, snow/trash removal & more - have more time to do what you love!

3305 Island Drive, Middleboro

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

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.

board logoCopyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!