Medway MA Historical Real Estate, Homes for Sale

2 Beds ⋅ 2 Baths ⋅ 73572052 MLS

Beautifully renovated from top to bottom. Have you been looking for one level living? Well look no longer. You will fall in love with this Ranch style home offering a newly added family room with an abundance of windows viewing the large deck and yard ,an open floor plan with access to the spacious kitchen, plenty of cabinets including a center island and pantry, all appliances purchased in 2026,open to the kitchen is the dining room boasting a beautiful electric fireplace, 2 rooms were converted to one big master bedroom, tiled full bath,2nd bedroom on main level. lower level is finished family room with full bath w/walk in shower. Renovations include heating, central air, electrical, kitchen ,baths, flooring, additions and so much more all located in a desirable neighborhood with easy access to major routes.

13 Delmar Rd., Medway

$499,000

2 Beds ⋅ 1 Baths ⋅ 73568149 MLS

**Offers due Monday Aug 31 by 1pm**Tucked away at the end of a quiet cul-de-sac, this charming home offers a bright and welcoming feel with tons of natural light. Gleaming hardwood floors flow throughout leading into the updated kitchen featuring granite countertops and stainless steel appliances. The sun-drenched dining room is the perfect spot to gather and entertain. Upstairs, you’ll find two bedrooms and a bathroom. The finished basement offers even more living space and opens out to a private yard. A newer roof and heating system adds peace of mind, and the location is hard to beat—just a short walk to beautiful Choate Park. Move right in and enjoy all this home has to offer. Open House Saturday Aug 29 from 11-1 and Sunday Aug 30 from 11-1.

17 Cutler St, Medway

$675,000

3 Beds ⋅ 3 Baths ⋅ 73563357 MLS

Spectacularly remodeled, from stem to stern, in 2018 with addition of first floor primary suite, 2 car garage and finished second floor. Turn-key 2108 sq ft Cape style home with 3 bedrooms, 2.5 baths and first floor primary suite. Hardwood flooring and ceramic tile flooring throughout first and second floors. Vinyl planking in lower level. Oversized 2 car attached garage with multiple closets and storage offering access to first floor and lower level. Beautiful cabinetry and granite countertops throughout. Bring your most discriminating buyer. First floor primary suite with upscale full bath, walk-in closet and french doors to patio area. Attractive Kitchen with stainless appliances and peninsula countertop for additional dining area. Huge Living Room with wood burning fireplace. Front porch to admire the beautiful landscaping in front yard. Large, level lot with professional landscaping throughout including firepit and beautiful night lighting. Fabulous workshop and utility area in lower level along with Playroom and Exercise Room. Two spacious bedrooms on second floor with Full Bath. Nothing to do but move right in. Generator and 3 mounted wall tv's included. Showings begin at Open House on Saturday, August, 15th from 12-2pm. A second Open House with be hosted on Sunday, August 16th from 12-2 pm. Don't miss out... this is an exceptional property!!!

52 Lovering Street, Medway

$549,900

3 Beds ⋅ 1 Baths ⋅ 73562925 MLS

Welcome to this beautifully refreshed 3-bedroom, 1-bath home nestled on just under a half-acre in a peaceful Medway neighborhood. Thoughtfully refinished throughout, the home showcases beautifully restored hardwood floors, brand-new countertops, and stylish light fixtures that create a warm, inviting feel. The spacious layout offers comfortable everyday living, while the full basement with both interior and exterior access provides abundant storage and flexible space to suit your needs. Off-street parking adds everyday convenience, and the generous yard offers plenty of room to relax, entertain, or enjoy the outdoors. Combining tasteful updates with a quiet setting, this move-in-ready home is a wonderful opportunity to enjoy all that Medway has to offer.

13 Center St, Medway

$599,000

4 Beds ⋅ 1 Baths ⋅ 73562230 MLS

Welcome to 14 Richard Rd in Medway! Use your own inspiration to bring this immaculate raised ranch to life. This home is set on a desirable corner lot in the sought-after Brentwood neighborhood. Featuring a spacious and versatile floor plan, this 4-bedroom home has been thoughtfully updated with newer windows, hardwood flooring, a heating system, central air, a water heater, and more. The sunny, bright cathedral-ceilinged living room flows into the open-concept eat-in kitchen, with direct access to an expansive deck and flat backyard, perfect for entertaining or everyday living. The walkout lower level includes a large family room, a bedroom and a small office, a laundry area, and ample storage. Enjoy the convenience of this prime location, close to the new urgent care facility, shops, Daycare, and restaurants. Great location ready for a new buyer; you don't want to miss it.

14 Richard Rd, Medway

$629,900

4 Beds ⋅ 2 Baths ⋅ 73553381 MLS

Bring your vision to this well-loved Medway Cape. Four bedrooms, two full baths, and a first-floor office create a flexible layout with two bedrooms on each level. Hardwood floors, stained wood trim, and built-ins give the home real character, while the family room and breezeway with wood stove add living space most Capes don’t offer. An attached garage and a large, level 0.82-acre yard with mature plantings are ready for gardening, play, and outdoor living. A framed, sided, and roofed expansion off the primary bedroom is already in place for extra living space when you choose to open the wall. Title V is in hand, and a one-year AHS home warranty (renewable) is offered to the buyer. Close to downtown Medway, schools, shopping, and restaurants—livable today, with room to update on your timeline and add real value.

141 Holliston St, Medway

$529,900

3 Beds ⋅ 1 Baths ⋅ 73555696 MLS

SPACIOUS 3 BEDROOM RANCH LOCATED IN A VERY DESIRABLE NEIGHBORHOOD OFFERS A LOT OF POTENTIAL FOR A NEW HOME OWNER. UPDATED ROOF - Vinyl windows , Hardwood in the main house- Dining Room, Living Room, Hall and Bedrooms - Attached family room/sun room off the rear of the house extends the living area. Some cosmetic updates will be needed but a great solid home! TOWN WATER - TOWN SEWER - SHOWINGS WILL BEGIN IMMEDIATELY - EASY TO SHOW - QUICK CLOSING POSSIBLE

7 Hemlock Dr, Medway

$799,000

4 Beds ⋅ 3 Baths ⋅ 73543934 MLS

Nestled on one of Medway's picturesque New England roads, this beautifully maintained property combines warmth, space, and versatility. Framed by a classic stone wall, the main home offers approx 2,200 square feet of living space, including four bedrooms and one full bathroom upstairs; and an eat-in kitchen, living room, family room, laundry room, and 3/4 bathroom on the first floor. A standout feature is the additional 676-square-foot bonus space above the garage with a separate entrance, kitchenette, and 3/4 bathroom - ideal for a guest room, home office, recreation room, craft room, or potential future in-law apartment/ADU. Outside, enjoy your private oasis featuring an in-ground swimming pool, hot tub, and plenty of space for entertaining and outdoor activities. Additional highlights include a two-car garage and a convenient location close to shopping, Route 109, Interstate 495, Medway's Choate Park, and Holliston's Stoddard Park on beautiful Lake Winthrop. Some photos are digitally staged.

10 Ellis St, Medway

$679,000

4 Beds ⋅ 1 Baths ⋅ 73549353 MLS

**Motivated Seller will provide $10,000 towards the buyer's closing costs OR towards adding an additional bathroom on the second floor.** Enjoy your morning coffee with breathtaking panoramic views of the Charles River from your deck and backyard in this beautifully updated 1870 Colonial, where historic charm meets modern comfort. Perfectly positioned along the waterfront, the property wraps around the Charles River, offering exceptional river frontage, tremendous water views, and a front-row seat to abundant wildlife. Offering over 2,200 sq ft, this home features a bright, open layout designed for comfortable living and effortless entertaining. The impressive kitchen showcases vaulted beamed ceilings, granite countertops, stainless steel appliances, and a large center island overlooking the main living area. Step outside and unwind as the river becomes your backyard. A flexible floor plan offers 4 bedrooms and a walk-up attic ready to be finished for additional living space. Set on a private ¾-acre lot with mature landscaping and convenient access to top-rated Medway schools, shopping, dining, and major routes to Boston, Worcester, and Providence.

4 Shaw St, Medway

$599,000

3 Beds ⋅ 2 Baths ⋅ 73546967 MLS

Tucked away on a country road just one mile from I-495, this inviting raised ranch offers the perfect blend of privacy and convenience. Sunlight fills the welcoming living room through an oversized bay window, creating a bright and comfortable space that flows into the dining area and kitchen. The main level features a spacious primary bedroom with direct access to the full bath, plus a second bedroom. The finished lower level offers exceptional flexibility with a fireplaced family room, third bedroom, half bath, and laundry room as well as a garage-converted bonus room with exterior access perfect for home office, gym or game room. Recessed lighting adds a modern touch throughout. Outside, enjoy a fully fenced backyard with mature fruit trees, a spacious composite deck, and an impressive outdoor kitchen—perfect for entertaining, relaxing, or making memories with family and friends. Welcome home!

94 West Street, Medway

$725,000

3 Beds ⋅ 2 Baths ⋅ 73544720 MLS

Welcome to this beautifully updated Colonial offering over 1,750 sq. ft. of turnkey living on more than half an acre of tree-lined land, providing exceptional privacy and a peaceful setting. This move-in ready home features 3 spacious bedrooms, including a large primary with a walk-in closet. The beautifully renovated bathrooms, refinished hardwood floors, fresh interior paint, quartz countertops, oversized center island, and new stainless steel appliances create a stylish, modern feel throughout. The heating system was updated in 2015, adding peace of mind. Blending classic charm with thoughtful updates, this home offers the perfect combination of comfort, space, and serenity—ready for you to move in and enjoy.

17 Farm St, Medway

$739,000

4 Beds ⋅ 4 Baths ⋅ 73542151 MLS

OPEN HOUSE IS CANCELLED!! Centrally located in the heart of Medway, the historic Old Parish House offers convenient access to schools, parks, trails, dining and everyday amenities, yet feels remarkably private and surprisingly quiet inside. Built using timbers from Medway’s original 1749 meetinghouse, this exceptional home has been masterfully restored to honor its remarkable history while providing the comfort, space and functionality of modern living. Magnificent exposed stone walls, original architectural details and timeless character are complemented by spacious rooms, thoughtful updates and a versatile layout across four finished levels. The welcoming foyer opens to formal living and dining rooms, while the family room features a wood-burning fireplace and flows into the chef’s kitchen with custom European cabinetry, slate countertops, stainless steel appliances, a new 60-inch Thor professional-style gas range, two Fisher & Paykel dishwashers and a pantry. A convenient half bath with laundry completes the main level. The second floor features a spacious primary suite with a walk-in closet and private bath with an oversized double shower, along with two additional generously sized bedrooms and a full bath. The top floor offers another large bedroom and a separate office, providing flexible space for working from home, hobbies or additional living space. The finished lower level adds exceptional versatility with a large open area, separate flex room, 3/4 bath, second laundry area and abundant storage, making it ideal for extended-stay guests, multigenerational living or recreation. Outside, the fully fenced backyard offers a peaceful, low-maintenance retreat with a custom stone patio, gazebo, decorative lighting, shed, designated dog run and convenient dog door, creating an ideal setting for relaxing, entertaining and pets. With parking for five vehicles, extensive finished space and a rare combination of privacy, convenience, history and modern comfort, the Old Parish House is truly one of Medway’s most distinctive homes.

199 Main St, Medway

$349,000

3 Beds ⋅ 1 Baths ⋅ 73532423 MLS

Contractor Special! Fantastic opportunity for investors, contractors, flippers, or buyers looking to build equity. This well-located single-family home offers 3 bedrooms and sits on a large lot with tremendous potential for renovation, expansion, or redevelopment possibilities (buyer to perform all due diligence). The property requires significant repairs and updates and will not qualify for FHA, VA, or conventional financing. Cash, hard money, or renovation loan buyers are encouraged. Conveniently located near major routes, shopping, restaurants, schools, and local amenities. Bring your vision and unlock the full potential of this property. Sold strictly AS-IS. Seller has never occupied the property and makes no representations or warranties.

252 Main St, Medway

$445,000

3 Beds ⋅ 1 Baths ⋅ 73501497 MLS

Motivated Seller Alert! Take advantage of a remarkable $10,000 seller credit to significantly lower your upfront closing costs or secure an interest rate buydown. Nestled in a peaceful, private cul-de-sac within Medway’s coveted historic village, this 3-bedroom home perfectly blends classic character with functional modern living. Step inside to a bright, efficient floor plan featuring a spacious main level that flows effortlessly out to a brand-new custom deck—your private oasis for outdoor dining and weekend entertaining. Upstairs, the second floor hosts three bedrooms, including a primary retreat complete with a sought-after walk-in closet. The third bedroom offers ultimate flexibility, serving as the perfect high-speed home office, nursery, or creative studio. Enjoy the ultimate balance of privacy and convenience with quick access to local boutiques, dining, top-rated schools, and major commuter routes. Bonus: hassle-free New England winters thanks to an established neighborhood arrangement for cul-de-sac snow plowing. Don't miss this high-value opportunity to keep more cash in your pocket at closing!

37 North, Medway

$875,000

73493305 MLS

Exceptional opportunity to acquire a fully operational, turnkey auto body repair facility including the real estate, established business, equipment, and client base. Located at 298 Village Street in Medway, this well-positioned property has been home to a long-standing collision repair operation serving the local community for years.Key highlights include:Sale includes business, real estate, equipment, and client listApproximately 2,600 SF building on 0.297 acresEstablished auto body and collision repair operationExisting customer base and insurance relationshipsFully equipped shop for immediate continued operationExcellent opportunity for owner-operator or expansion of existing business

298 Village Street, Medway

$600,000

2 Beds ⋅ 1 Baths ⋅ 73487960 MLS

This property is a must for horse lovers or builders looking for land. This 2 bedroom house with an attached 1 car garage sits on 4.28 Acres and has a large detached barn with 3 horse stalls and a second floor for hay or other storage. This quiet serine property abuts 11 acres of beautiful woods behind it which will be listed separately. Located close to Rt. 495 and just off of Rt. 109 makes this the perfect house to start a new adventure. Property is being sold as is. First showing Open House 3/21 Saturday 11 am-2 pm . All offers are due by Tuesday March 24, 2026 at 5 pm. Use showtime after 3 pm Sunday March 22, 2026.Seller reserves the right to accept offer when presented.

42 Fisher St, Medway

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Medway Historical Real Estate