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4 Kingson Ln Unit 1, Medway
$599,900
2 Beds ⋅ 3 Baths ⋅ 73597234 MLS ⋅ ['Woodside'] BLDG.
A rare opportunity to find a spacious end unit with 2 car garage in beautifully maintained Woodside Condominiums. The minute you enter you feel a relaxed comfort w/ a refined style. The functional floor plan is enhanced with dramatic ceilings and natural light streaming through the many oversize windows. A bright cabinet packed kitchen offers granite countertops and inviting breakfast nook. There is a 1st floor primary w/ walk in closet and bath. 2nd floor offers a potential 2nd primary opportunity with full bath; and an office/guest space and a loft overlooking the fireside dining/living spaces. 2nd floor hosts laundry room w/ additional storage. The basement is full walkout w/windows and door to lush landscaped yard. 2 zone central air . Large, new composite deck. The community is inviting; offering casual get togethers and a community garden if one wishes to participate. Conveniently located just a short distance to shopping, highways and Boston commuter rail.

4 Kingson Ln Unit 1, Medway
17 Holliston St, Medway
$849,000
12 Beds ⋅ 7 Baths ⋅ 73596840 MLS
A property with possibilities, offering the space and existing infrastructure to support a new vision. Set on a 19,166-square-foot lot within Medway’s Village Multifamily Housing Overlay District, 17 Holliston Street presents an opportunity to explore renovation, continued residential or institutional use, or potential redevelopment, subject to applicable zoning, permitting, and approvals. The property invites consideration by nonprofit organizations, housing providers, investors, and developers seeking a site with flexibility for its next chapter. The over 5,800 sq ft building includes 17 rooms with 5 full and 2 half bathrooms spread over two levels. It features a ramped entrance, sprinkler fire suppression system, full deleading compliance, 200-amp electrical service, and gas heating. With this existing infrastructure, along with a central location 5 miles from 495 and 10 miles from Patriot Place, this property offers a great starting point for evaluating a range of future possibilities.

17 Holliston St, Medway
65 Holliston Street, Medway
$449,900
3 Beds ⋅ 1 Baths ⋅ 73596725 MLS
Opportunity meets affordability in Medway! Welcome to this charming New England Cape, offering the perfect combination of move-in ready comfort and the opportunity to make it your own! This 3 bedroom, 1 bath home sits on a quarter acre corner lot and has been freshly painted, providing a great starting point for its next owner. The flexible floor plan features 2 bedrooms and a full bathroom on the main level, while the spacious second floor bedroom offers endless possibilities! Create a private primary retreat, a bedroom with an oversized walk-in closet, a combination bedroom and home office and MORE! The unfinished basement provides additional potential for future living space, storage, a workshop and......MORE! With a little creativity and some personal touches, this home offers an exciting opportunity to add value and build equity over time. Enjoy the charm of Medway, with beautiful outdoor destinations like Choate Park, scenic trails, and a welcoming small town atmosphere. Why pay for someone else's upgrades when you can create your own vision? Whether you're purchasing your first home, downsizing, or looking for a property with potential, this is an opportunity you won't want to miss!

65 Holliston Street, Medway
21 High Street Unit A, Medway
$539,900
2 Beds ⋅ 2 Baths ⋅ 73596453 MLS
Fully renovated Medway condo in 2022. Enjoy all the charm of years gone by with the added security of extensive renovations for care free living. You will love the newer kitchen with stainless steel appliances, granite counter tops, and white cabinets. First floor bathroom has a new tiled shower and laundry. Spiral staircase in front entrance, additional staircase off kitchen. Two large bedrooms upstairs. Also has a second floor bonus room.. Walk up attic. Need a 1st floor bedroom and bath? This condo has it, you can easily have a 3rd bedroom! Gleaming hardwood floors. Newer on demand hot water heater. Plumbing and electrical upgrades. Exterior upgrades include roof, siding and gutters and all vinyl windows Town water, sewer and natural gas heating. Low condo fee! Quick closing possible.

21 High Street Unit A, Medway
16 Meryl St, Medway
$669,900
3 Beds ⋅ 2 Baths ⋅ 73596400 MLS
Welcome Home! This inviting 3-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and versatile living space in a desirable neighborhood just a short distance from town. Whether you're purchasing your first home, looking to simplify, or searching for a home with room to enjoy your favorite hobbies, this property has so much to offer! Step inside to discover gleaming hardwood floors and vaulted ceilings that create an open, airy feel throughout the main living area. The attached, year-round sunroom provides a wonderful space to relax with backyard views. Need additional room to spread out? The lower level offers even more flexible living space, complete with a gas stove, making it a cozy spot for entertaining, hobbies, office or workout space. Plus, laundry, half bath, cedar closet and utility room with walkout access to the yard. Car enthusiasts, hobbyists, and anyone in need of extra workspace will appreciate the heated, oversized two-car garage, offering plenty of room for vehicles, tools, and projects. Outside, enjoy the partially fenced yard, along with a deck and patio that provide great options for outdoor entertaining, summer barbecues, gardening, or simply relaxing in your own outdoor space. Enjoy added peace of mind with several important updates already completed, including a brand-new roof being installed, heating system, central air conditioning and a hot water heater all updated within the last three years. Freshly painted interior and newer windows, installed in 2019, are more valuable improvement. With its comfortable layout, additional living space, fantastic garage, outdoor amenities, and major updates already taken care of, this home is ready for its next chapter. Conveniently located near town while offering a welcoming neighborhood setting, it's an opportunity you won't want to miss. Whether you're just starting out or ready to downsize without giving up space and convenience, this home is waiting for you.

16 Meryl St, Medway
4 Lewis Drive, Medway
$839,900
4 Beds ⋅ 3 Baths ⋅ 73596227 MLS
Welcome to this beautifully maintained 9-room Colonial, lovingly cared for by its original owner and tucked away in a desirable cul-de-sac neighborhood! Offering a wonderful blend of classic charm, thoughtful updates, and inviting living spaces, this home is ready to welcome its next owners. The custom-designed kitchen is a standout, featuring gorgeous custom cabinetry, stainless steel and black appliances and attractive pendant lighting. Just off the kitchen, the sun-filled four-season room is surrounded by windows and crowned by a skylight, creating a bright and relaxing space to enjoy throughout the year. Step outside onto the private deck overlooking a spacious, wooded backyard, offering a peaceful setting for morning coffee, outdoor entertaining, or simply unwinding at the end of the day. The comfortable family room features newer hardwood flooring and a fireplace with a charming brick hearth, providing a cozy gathering place on cooler evenings. Conveniently located just off the family room, the first-floor bath and laundry area add everyday practicality. The living and dining rooms showcase refinished hardwood floors, while classic chair rail detailing adds timeless appeal. With nine rooms offering flexibility for everyday living, entertaining, working from home, or accommodating guests, there is room to suit a variety of lifestyles. Upstairs, you'll find four generously sized bedrooms and a full guest bath. The primary suite offers dual closets and a private bath featuring a newer vanity and walk-in shower. Additional highlights include a two-car attached garage and a full basement with excellent potential for future finishing, additional living space, or recreation. All windows and doors have been replaced. Comfort and efficiency are enhanced by a high-efficiency Buderus boiler, heat pump, and A/C, providing versatile heating and cooling options. Ideally situated for commuters, this home offers convenient access to major routes and is approximately 3 miles from the commuter rail. Boston and Providence are each approximately 25 miles away. A wonderful opportunity to own a lovingly maintained Colonial in a sought-after cul-de-sac setting, with inviting indoor spaces, a private wooded backyard, and the opportunity to make it your own. Come see all this special home has to offer!

4 Lewis Drive, Medway
1 Alder St, Medway
$524,900
4 Beds ⋅ 2 Baths ⋅ 73594296 MLS
Offers due Monday, October 26th at 5pm. Fall in love with this beautiful, turnkey 4-bedroom, 2-full-bath home, fully renovated and thoughtfully redesigned with extensive interior and exterior improvements.The sellers have prioritized maintaining a healthy home environment through regular upkeep, proactive maintenance, and quality upgrades. Exterior improvements completed within the past five years include a new roof (2026), an upgraded front entry, and an enhanced patio, walkway, and fire pit area. The sun-filled family room leads seamlessly into the updated eat-in kitchen, which features upgraded cabinetry, granite countertops, newer stainless steel appliances, and a dedicated coffee and beverage station. The kitchen opens to a private backyard with a patio and fire pit, ideal for outdoor dining and entertainment. The main level also includes a beautifully redesigned full bathroom with a walk-in shower. Inside, fresh paint and new hardwood flooring throughout create a bright, cohesive flow. For added convenience, the laundry room was strategically relocated to the main level. A private flex room on the first floor can easily serve as a 4th bedroom and also suitable for a buyer requiring single-level living. The basement provides over 800 sq ft of additional storage space with convenient walk-out access to the private backyard. Conveniently located close to schools, shopping, dining, and commuter routes, this move-in ready home is ready for its next chapter.

1 Alder St, Medway
14 Sanford St Unit 17, Medway
$365,000
2 Beds ⋅ 2 Baths ⋅ 73591398 MLS ⋅ ['Sanford Mill Condo'] BLDG.
Gorgeous open loft condo in historic mill building invites you to take advantage of all this home has to offer. Inviting plan with open kitchen through eating area and into the living room. The space is adorned with huge windows and a ton of natural light making the main level pop! A half bathroom completes this space and makes it perfect for relaxing - or entertaining and more. The lower level shows off more large windows in each of the two bedrooms, while also providing you with your full bathroom and laundry room - so you don't have to go up or downstairs from your bedroom to those! Closets and nooks and foyer space allow for some creative storage - two parking spots makes it easy to come and go. The mill is directly on the Charles River and has a great picnic area out back. Just beyond is the entrance to the Medway Amphitheater - a 4.5 acre open space site allowing for direct access of kayaks, fishing, walking trails and so much more. All of this, just outside your windows - it is truly a location to be!!

14 Sanford St Unit 17, Medway
21 Summer St, Medway
$200,000
73591322 MLS
Opportunity to build your own home in Medway! Lot conveniently located a few minutes from Rt 495 - perfect for commuters. Survey & Perc test responsible by buyer to determine if lot is buildable with wetlands in the back of lot.

21 Summer St, Medway
4 Hill St, Medway
$679,900
3 Beds ⋅ 2 Baths ⋅ 73591058 MLS
A Private Nature Retreat with Contemporary Flair, Distinctive style, room to breathe, and a connection to the outdoors. Set on 2.3 private acres, this one-of-a-kind contemporary home offers a refreshing blend of architectural character, inviting living spaces, and a tranquil, sylvan-framed haven—all with the convenience of nearby amenities. Inside, vaulted wood ceilings and warm wood floors create an airy, welcoming atmosphere. The spacious, open-concept kitchen is truly the heart of the home, featuring stainless steel appliances, a cozy fireplace, and an expansive dining area perfect for gathering and entertaining. An adjoining office or den provides a versatile space for working from home or simply unwinding, with both areas opening to an outdoor balcony and an expansive entertaining deck. The family room offers its own inviting space, highlighted by vaulted wood ceilings, bamboo flooring, and direct access to yet another deck—creating multiple opportunities to relax, entertain, and enjoy the surrounding natural beauty. The flexible bedroom layout includes a vaulted third bedroom and two additional bedrooms, highlighted by a spacious primary and generous walk-in closet. Sliding glass doors in both the primary and secondary bedrooms invite serene backyard views of the outdoors. Two full bathrooms provide everyday comfort and convenience. Additional features include central air conditioning, abundant recessed lighting, brand-new roof and freshly painted exterior. Private, peaceful, and full of personality, this distinctive home offers a lifestyle that feels a world away from the ordinary while keeping everyday conveniences close at hand. If you're looking for space, character, and a special connection to nature, this inviting contemporary is ready to surprise you. Showings begin immediately, Open House Saturday 10/17 from 11:00 - 1:00

4 Hill St, Medway
26 Hooksett Circle, Medway
$739,900
4 Beds ⋅ 3 Baths ⋅ 73590576 MLS
Set on an expansive 1.23-acre lot in Medway, this impressive four-bedroom Colonial offers a fantastic blend of space, style, and outdoor enjoyment! The main living room features a cozy fireplace, while the formal living room flows seamlessly into the dining room, creating an ideal setting for entertaining. At the heart of the home, the chef’s kitchen showcases modern stainless steel appliances, a center island, and a comfortable dining area with direct access to the back deck. A half bathroom with convenient first-floor laundry completes the main level. Upstairs, you’ll find four spacious bedrooms, including a primary suite with two closets and its own private full bathroom. An additional full bathroom is located just off the hallway. Outside, the back deck overlooks a patio and firepit area surrounded by a wooded yard, offering ample room to relax, gather, and enjoy the peaceful setting. Valuable updates include a roof replaced in 2022, plus custom front and rear doors installed within the last two years. With its classic Colonial layout, generous lot, and thoughtful improvements, this Medway home is ready to impress!

26 Hooksett Circle, Medway
10 Village Street, Medway
$685,000
4 Beds ⋅ 2 Baths ⋅ 73590400 MLS
Welcome home to this beautifully updated Raised Ranch with a full in-law suite!! This home was fully renovated in 2016 and offering a versatile layout with plenty of space for comfortable living. The main level features an inviting open floor plan that seamlessly connects the living room, kitchen, and dining area, creating a wonderful space for everyday living and entertaining. Three generously sized bedrooms and a full bath with a double vanity complete the main level. The bathroom offers convenient access from both the hallway and the primary bedroom. The lower level features a spacious, full in-law suite complete with a large kitchen, comfortable family room, bedroom, and full bath. With its own direct access from the driveway, this separate living space is ideal for extended family, guests, or added flexibility to suit your needs. Situated on a large, level lot with an expansive driveway offering ample off-street parking, this home combines versatility, convenience, and plenty of room to enjoy!

10 Village Street, Medway
172 Holliston St, Medway
$650,000
3 Beds ⋅ 1 Baths ⋅ 73589771 MLS
Looking for a move-in ready ranch? This might just be the one! Completely updated inside in 2024, this contemporary 3-bedroom, 1-bath home sits on a private 0.79-acre lot. The spacious living room features a vaulted ceiling, bay windows that fill the space with natural light, and a decorative fireplace, with room for a dining area if desired. The updated kitchen offers new cabinets, stainless-steel appliances, and an eat-in dining space, while an updated bathroom and new luxury vinyl flooring throughout complete the refresh. The generously sized bedrooms offer ample closet space, with one currently set up as a home office. Stay comfortable year-round with an energy-efficient heat pump for heating and cooling, plus a propane forced hot air system as backup. Outside, enjoy a fenced backyard, a patio for relaxing or entertaining, and a circular driveway with ample parking. All just minutes from downtown Medway, shopping, and a variety of restaurants. Don't wait to see this one-level gem!

172 Holliston St, Medway
48 Lovering St Unit 8, Medway
$399,000
3 Beds ⋅ 2 Baths ⋅ 73588414 MLS
This beautifully appointed two-story townhouse condo offers three bedrooms and two full baths, with a bright, welcoming layout and inviting outdoor space. Cathedral ceilings and an open-concept design enhance the main level, featuring a spacious living room, dining area, eat-in kitchen, and generously sized bedroom. The lower level adds exceptional versatility with a comfortable family room, two additional bedrooms, a laundry room, and pantry. Step outside to a private deck and expansive backyard—perfect for relaxing or entertaining. Ideally situated just minutes from the highway and Franklin commuter rail, with convenient access to shopping, dining, the town park, and elementary school.

48 Lovering St Unit 8, Medway
25 Oakview Cir, Medway
$649,900
4 Beds ⋅ 2 Baths ⋅ 73587672 MLS
Welcome to 25 Oakview Circle! This beautiful L-shaped ranch sits on a side street in Medway near a public park and Next Venture Farm. Once owned by the same family for many years, the home holds a special piece of its past, with family history inscribed on its main beam. Freshly painted and move-in ready, the main level features hardwood floors, a fireplaced living room open to an eat-in kitchen, a separate dining room, and a sunroom/family room leading to a deck and beautiful backyard. Three bedrooms and a full bath complete this level. The partially finished lower level offers a recreation room, an additional bedroom, and a full bath with shower, plus laundry, storage, and utility areas. Outside, enjoy a level lot of nearly 16,000 sq. ft., a circular driveway, a detached one-car garage with a high ceiling and extra storage, and a separate shed. Three-zone hot-water baseboard heat and an AC unit add comfort to this inviting home.

25 Oakview Cir, Medway
10 Kings Lane, Medway
$749,900
4 Beds ⋅ 3 Baths ⋅ 73587580 MLS
Welcome to 10 Kings Lane, Medway! Set in a desirable cul-de-sac neighborhood, this spacious 2,254 square foot Colonial offers a wonderful combination of comfort, functionality, and inviting living spaces. Thoughtfully updated and well cared for this move-in ready home offers charm as well as a modern appeal. The open-feeling first floor features a family room with a fireplace and a living room that flows into the dining room, perfect for holidays and entertaining. The dining room showcases hardwood flooring and a walk-out bay window, filling the space with natural light. Don't miss the spacious kitchen with updated finishes, stainless appliances, ample cabinet space and a convenient peninsula for casual dining. A door from the kitchen leads to a screened porch overlooking the fenced backyard—perfect for relaxing, entertaining, gardening, or enjoying the outdoors. The backyard also includes a garden and storage shed. Upstairs, you'll find four spacious bedrooms, including a comfortable primary suite. There are two full baths both featuring double-sink vanities and tile flooring. A first-floor half bath with laundry adds everyday convenience. Recent improvements include an updated propane heating system, updated appliances, fresh interior paint, and new carpeting in the living room and family room. Central Air, and a two-car garage add to the home's comfort and practicality. Ideally located just minutes to the Medway Middle School, Burke Elementary School, shopping & restaurants. This well-maintained Colonial offers generous room sizes, a great floor plan, and a desirable neighborhood setting. A wonderful opportunity to make this welcoming Medway home your own!

10 Kings Lane, Medway
281 Village Street, Medway
$675,000
4 Beds ⋅ 3 Baths ⋅ 73585746 MLS
**Open House Canceled - Offer Accepted** Welcoming, sunlit, and full of possibilities, this expanded ranch has been in the same family since 1973, evolving to meet their changing and aging needs and now offering your family that same flexibility. There's more to discover here than meets the eye. Entertaining flows through the home's oversized kitchen, formal dining room, and living room. Generous closets, hardwood floors, picture windows, and skylights create bright, comfortable spaces. Its 4 bedrooms and 3 full baths occupy three areas: a main-level bedroom, currently a home office, with a nearby full bath; an upstairs primary bedroom and full bath; and a private wing a few steps down with two bedrooms, a bonus room, and full bath. With its own entrance, kitchenette, and separation from the main house, this wing suits in-law or multigenerational living, yet can easily return to its original layout. Central air, natural gas, and owned solar panels provide comfort and efficiency. Outside, a patio, garden space and fenced backyard offer space for relaxing and entertaining, complemented by a one-car garage and ample parking. Modernize and personalize to suit your family's needs.

281 Village Street, Medway
26 Waterview Drive, Medway
$859,900
4 Beds ⋅ 3 Baths ⋅ 73585553 MLS
Set at the end of a cul-de-sac, this inviting colonial enjoys a beautiful private setting on 1.83 acres, surrounded by mature trees and peaceful pastoral views. Whether relaxing on the large composite deck, gathering on the adjoining patio or enjoying a quiet morning listening to the birds, the property makes it easy to spend time outdoors. While offering exceptional privacy, shopping, dining, recreation and access to Rte 495 are just minutes away. Nearby favorites, including the Milford Upper Charles Trail, Choate Park, Medway Community Farm, the seasonal Farmers Market and Medway Porchfest, add even more to enjoy close to home.Inside, the home feels warm and welcoming, with comfortable spaces to gather and unwind. Hardwood floors extend throughout the first and second levels, while the fireplaced family room features wide pine floors that add warmth and character. Upstairs, generously sized bedrooms include a spacious primary suite with two closets and a beautifully updated en-suite bath. Views toward the Charles River can be enjoyed from the second floor, with seasonal views from the deck and backyard.The finished lower level offers additional flexibility for a playroom, home office, media room or guest space, with new carpeting, recessed lighting, generous closets and ample storage. Thoughtful updates include refinished hardwood floors, ductless mini-splits, heating system, updated primary bath, granite kitchen countertops and recessed lighting. A new composite deck and patio extend the living outdoors, while a Tesla charger, oversized two-car garage with direct yard access and outdoor shed provide added convenience and storage.With its natural beauty and peaceful surroundings, this is a home where the setting is every bit as enjoyable as the space inside.

26 Waterview Drive, Medway
3 Carol Lane, Medway
$579,000
3 Beds ⋅ 2 Baths ⋅ 73585479 MLS
Move right into this bright and inviting ranch offering comfortable one-level living with the added flexibility of a finished walk-out lower level. Sun-filled living spaces flow effortlessly for everyday living and entertaining, while the lower level provides exceptional versatility with multiple finished rooms ideal for a family room, home office, playroom, gym, or guest space. Outside, enjoy a fully fenced backyard with plenty of room for pets, play, gardening, or summer gatherings on the deck. Located in an established neighborhood just minutes from Medway Center, Choate Park, Medway Community Farm, local restaurants, shopping, schools, the Charles River, and Franklin MBTA Commuter Rail. Easy access to Route 109, I-495, and surrounding communities makes commuting a breeze. Subject to sellers closing on their new home in early January.

3 Carol Lane, Medway
166 Village St Unit 202, Medway
$279,000
1 Beds ⋅ 1 Baths ⋅ 73585406 MLS ⋅ ['Clark Partridge Condominium'] BLDG.
Cheaper than rent!! Wait until you see this perfect little one bedroom condo. Centrally located in the center of Medway with easy access to everything. Known as the Clark Partridge House condominiums this converted antique is the perfect opportunity to own for less than rent. All on the second floor, above a commercial space. Eat in kitchen complete with refrigerator. No need to hit the laundromat, this unit comes with its own washer and dryer. Large walk in closet. Freshly cleaned carpets, and paint touch up. Central A/C. Two parking spaces. Condo fee covers water and sewer. Pets allowed with restrictions. Quick close possible. Be in before the holidays.

166 Village St Unit 202, Medway
12 Jasmine Rd, Medway
$879,900
4 Beds ⋅ 3 Baths ⋅ 73585137 MLS
Welcome home to this meticulously maintained Custom Colonial, lovingly cared for by its original owners. Set on a beautiful wooded 1.47 acre lot in an established neighborhood, this spacious 10 room, 4 bedroom, 2.5 bath home offers comfort, privacy and room to grow. Sun filled interiors feature oversized windows, a kitchen with granite countertops, stainless steel appliances and island, first floor laundry, and a cozy family room with wood burning fireplace. French doors connect the dining room to living room. Upstairs the primary suite offers an updated full bath and walk-in closet, plus 3 additional bedrooms and a full bath. The finished walk out lower level offers a versatile bonus room, office and utility room with full size windows. Enjoy the picturesque backyard from the deck or stone patio surrounded by mature trees and large well maintained side yard. Attached 2 car garage. High efficiency tankless gas boiler and a/c installed 2021. Roof replaced 2019. Convenient commuter location with easy access to commuter rail, Route 495 and Mass Pike. Desirable school system. Come see all this special home has to offer!

12 Jasmine Rd, Medway
31 Coffee Street, Medway
$690,000
3 Beds ⋅ 2 Baths ⋅ 73585036 MLS
Charming Raised Ranch offering an expansive, flexible layout designed for modern living! This inviting 3-bedroom, 2-full-bath home features hardwood flooring and an updated kitchen with granite countertops and custom cabinetry and an open dining room. The finished lower level provides additional living space with a bright tiled mudroom, family room, extra bedroom, a home office, full bath, and laundry—ideal for guests, potential In-Law, or extended living. Enjoy the outdoors from the composite Trex deck overlooking a spacious, private backyard bordered by a wooded area. A shed provides additional storage, while the garage offers excellent space for storage and workshop use. Numerous updates provide peace of mind, including a complete renovation in 2008 with roof, windows, siding, and stairs, plus a living room addition, composite deck and stairs, and lower-level addition in 2015. Additional features include central air and a radon remediation system. Convenient commuter location close to Medical Facility, schools, restaurants & shopping with easy access to I-495 and the Mass Pike. A wonderful opportunity to enjoy a thoughtfully updated home with plenty of space, privacy, and versatility. Simply unpack and enjoy!

31 Coffee Street, Medway
2 Elm Street Unit B, Medway
$450,000
3 Beds ⋅ 2 Baths ⋅ 73584941 MLS
Welcome to 2B Elm Street! Tucked away on a side street yet conveniently located near the center of Medway, this inviting 3-bedroom, 1.5-bath home offers 1,377 square feet of comfortable living space and plenty of outdoor room to enjoy. The expansive backyard and beautiful multi-level deck create an ideal setting for relaxing, entertaining, or enjoying summer evenings outdoors. Inside, the home offers a practical layout with three bedrooms and one and a half baths. Best of all, there are NO CONDO FEES, making this a wonderful opportunity for buyers looking for the convenience of a great location without the added expense of condo ownership. Close to Medway's town center, local shops, restaurants, schools, and community amenities. Don't miss the opportunity to make 2B Elm Street your new home!

2 Elm Street Unit B, Medway
30 Cottage St, Medway
$488,900
5 Beds ⋅ 2 Baths ⋅ 73582521 MLS
A fantastic opportunity to own a 5-bedroom home in desirable Medway just got better! Seller will be upgrading the electrical service to the house with new circuit breaker panels! Lovingly owned by the same family for over 70 years, this spacious home offers over 2000 square feet of living space, 1 & ½ baths, and plenty of room for everyone. Set on over half an acre, the property features a beautiful yard and two sheds providing plenty of storage. The family room was added in 1965, with the front room added in 1970, providing additional space and character. A four-year-young pellet stove offers an additional heat source and an opportunity to help offset oil heating costs. Many newer updates include the washer and dryer, stove, refrigerator, furnace, and water heater. The main portion of the roof is approximately 15–20 years old, and many windows have been replaced within the past 15 years. Bring your vision and ideas to make this home your own and unlock its full potential. With generous living space, a large lot, a desirable Medway location, and many newer updates, this home is ready for its next chapter!

30 Cottage St, Medway
6 Carriage House Way, Medway
$1,079,000
4 Beds ⋅ 3 Baths ⋅ 73581943 MLS
Exceptional 4+BR, 2.5BA Custom Colonial in sought-after Claybrook Farm Estates, offering refined style, everyday comfort & exceptional outdoor living. Beautifully landscaped grounds create a private summer retreat featuring a composite deck, heated inground pool, extended patio with fire-pit area and newly installed privacy fencing. A true highlight is the spacious outdoor cabana, an inviting gathering place for watching TV, relaxing poolside and hosting outdoor celebrations. A charming shabby-chic pool house completes this exceptional backyard setting. The open floor plan features 9’ ceilings, gleaming hardwoods & custom millwork.The bespoke chef’s kitchen offers custom cabinetry, an oversized island and a casual dining area, flowing seamlessly into the sun-filled family room. Elegant formal living and dining rooms, along with gracious entry spaces, provide flexibility for comfortable family living and effortless entertaining. A conveniently located first-floor laundry area adds to the home’s thoughtful design.The upper level features a spacious primary suite with a spa-like bath with quartz countertops, marble shower flooring, radiant heat and a built-in bench. An oversized walk-in closet is outfitted with extensive custom built-ins and its own private laundry area. Three additional generously sized bedrooms complete the upper level. The finished lower level features three separate rooms, offering a flexible layout that can easily adapt to suit a variety of needs, including work-from-home space, a media or game room, fitness area, playroom, hobby room or comfortable accommodations for overnight guests. Top-rated schools & convenient access to highways and commuter rail. Move-in ready and designed for making memories, this remarkable home offers a private retreat for every season.

6 Carriage House Way, Medway
5 Wildebrook Rd, Medway
$1,249,000
5 Beds ⋅ 4 Baths ⋅ 73579593 MLS
NEW PRICE - Exceptional value in one of Medway's most beautiful homes! This five-bedroom home combines more than 4,000 square feet of beautifully finished living space with an extraordinary backyard designed for everyday enjoyment and entertaining. The outdoor space is the showpiece, with a saltwater in-ground pool, raised spillover spa, expansive travertine terrace, pergola lounge area, natural-stone fire pit, open lawn, dedicated sport court, mature landscaping, privacy fencing, and large storage shed. Whether it's pool days, games on the court, dinner under the pergola, coffee on the deck, or evenings around the fire, the backyard offers a private resort-like setting that is truly unique. Inside, the layout is warm, open, and highly functional. The kitchen features a large center island with seating, generous cabinetry, and a beverage station with wine storage and a beverage/wine cooler. The dining area and sun-filled family room connect comfortably, with hardwood floors, and a gas fireplace, while the two-story foyer adds a bright and welcoming entry. Upstairs, the spacious primary suite includes a walk-in closet and spa-style bath with soaking tub, double vanity, and glass-enclosed tiled shower with dual shower-heads. A guest ensuite, three additional bedrooms, and second-floor laundry provide flexibility for family and guests.The main level includes a home office with French doors and a mudroom with built-ins. The finished basement offers additional flexible living space for a home gym, media room, playroom, guest space or second office. Recent updates include a newer roof with transferable warranty, updated HVAC, new pool liner, recently installed whole-house water filter, washer and dryer replaced in 2025, new upstairs carpeting and stair runner, newly epoxied garage floor, and freshly sealed driveway. A rare opportunity to own a home that brings together space, condition, flexibility and an exceptional indoor-outdoor lifestyle in one complete package! Buyers and Buyers agents to verify.

5 Wildebrook Rd, Medway
14 Waterside Run Unit 14, Medway
$799,000
2 Beds ⋅ 3 Baths ⋅ 73580425 MLS ⋅ ['Willowside Medway'] BLDG.
OPEN HOUSES CANCELED-OFFER ACCEPTED Welcome Home to this beautifully maintained townhouse in Medway's Premier 55+ community offering the perfect combination of modern style, spacious living, and everyday convenience. A welcoming front porch sets the tone as you enter this thoughtfully designed home featuring an open floor plan ideal for both comfortable living and entertaining. The gourmet kitchen is the heart of the home, showcasing a large center island with plenty of space for meal preparation, casual dining, and gathering with family and friends. The kitchen flows seamlessly into the dining and living areas, where a gas fireplace creates a warm and inviting atmosphere. Step directly from the living room onto the private deck, the perfect place to enjoy your morning coffee, unwind at the end of the day, or entertain outdoors. The FIRST-FLOOR PRIMARY SUITE provides the ease of main-level living and features a private ensuite bath, creating a comfortable retreat. Two dedicated office spaces offer exceptional flexibility for working from home, hobbies, a study, or additional guest space. The second level features a comfortable additional bedroom and an expansive loft, offering versatile space for a family room,, fitness space, or relaxing retreat. The walk-out basement provides even more possibilities for future finished living space, recreation, storage, or a home gym while offering convenient access to the outdoors. With its modern design, flexible floor plan, front porch, private deck, and numerous community amenities to enjoy, this exceptional townhouse offers low-maintenance living without sacrificing space, comfort, or style. Move right in and enjoy everything this beautiful home and community have to offer!

14 Waterside Run Unit 14, Medway
50 Main St., Medway
$600,000
3 Beds ⋅ 2 Baths ⋅ 73580054 MLS
Discover the charm of suburban living at this wonderful updated ranch. Offering 1712 square feet of thoughtfully designed living space, this home is ready to welcome its next chapter. The house provides three comfortable bedrooms, offering flexible arrangements for rest and personalization. An updated kitchen and two updated bathrooms ensure convenience and comfort for daily routines. An enclosed 3-season porch overlooks an outdoor patio and ample outdoor space for leisure and potential gardening projects. The property also includes a one-car garage, providing secure parking and additional storage. This address presents an opportunity to create your ideal home. Envision your future at 50 Main St. Medway, MA.

50 Main St., Medway
4 Sterling Circle Unit 4, Medway
$749,900
5 Beds ⋅ 4 Baths ⋅ 73578732 MLS
Welcome to 4 Sterling Circle, where the ease of condo living comes with the flexibility of a home built for today’s lifestyle. Built in 2021, this thoughtfully designed property features an inviting open floor plan with seamless flow between the kitchen, dining, and living areas—ideal for both everyday living and entertaining. Five bedrooms and 3 full and 1 half baths include the rare convenience of both a first-floor and second-floor primary suite, offering flexibility for guests, multigenerational living, or a private retreat. With over 3,200 sq. ft. of living space, a 2-car garage, and a private back patio, there’s plenty of room to live, work, and gather. Set in desirable Medway, known for its welcoming community, excellent schools, and charming New England setting, this home offers a wonderful place to put down roots. Come see why 4 Sterling Circle could be the perfect fit for your next chapter! **see MLS# 73574632 for official condo listing**

4 Sterling Circle Unit 4, Medway
23 Oak St, Medway
$824,900
4 Beds ⋅ 3 Baths ⋅ 73578538 MLS
Welcome to 23 Oak Street—a spacious four-bedroom Colonial where comfort meets convenience. A half-circle driveway welcomes you home, providing easy access and ample parking. Ideally located in a desirable Medway neighborhood, this property is close to Choate Park, schools, restaurants, shops, and major routes. Inside, the bright, open floor plan creates a warm and inviting atmosphere. The spacious living room features new oak flooring, a soaring cathedral ceiling, a cozy gas fireplace, and large windows that fill the space with natural light. At the heart of the home, the expansive kitchen offers abundant cabinetry and newer stainless-steel appliances—ideal for both everyday living and entertaining. The adjoining dining area opens to a fully furnished three-season porch, providing a peaceful space to enjoy the outdoors. The recently updated finished walkout basement, offers additional flexible living space suitable for a home office, playroom, gym, or media room. Upstairs, four generously sized bedrooms provide comfortable retreats. The primary suite features a walk-in closet and an en-suite bathroom with an attractive wood-burning fireplace serving as a charming focal point. An additional full bathroom and half bath offer convenience for family and guests. Many updates including Roof & A/C, plus highlights include a two-car garage, first-floor laundry, and a convenient location near shopping, dining, schools, parks, and major commuter routes. 23 Oak Street perfectly blends classic Colonial charm with modern comfort and everyday practicality.

23 Oak St, Medway

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