Medway MA Single Family Real Estate, Homes for Sale

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

$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

$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

$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

$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

$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

$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

$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

$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, a new heating system, refreshed baths, 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

$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

$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

$489,900

5 Beds ⋅ 2 Baths ⋅ 73582521 MLS

Fantastic opportunity to own a 5-bedroom home in desirable Medway at an incredible price! 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 most windows have been replaced within the past 15 years, with the exception of windows in the additions. 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

$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

$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

$615,000

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

$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

$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

$1,185,000

4 Beds ⋅ 3 Baths ⋅ 73577693 MLS

Welcome to your own castle at 14 Iarussi Way, located in prestigious Evergreen Meadows on a private wooded cul-de-sac abutting conservation land. This exceptional, stunning partial-stone-front Colonial blends luxury, craftsmanship, and livability. A dramatic 2-story foyer, soaring ceilings, French doors, gleaming hardwoods, custom blinds, and exquisite custom millwork makes an impressive first impression, setting the tone for quality workmanship throughout.The gourmet chef’s kitchen features custom cabinetry, granite countertops, premium appliances, oversized island, walk-in pantry, and beverage fridge. An adjoining mudroom with separate entrance and direct access to the 3-car garage adds convenience, along with a first-floor laundry and half bath, flowing seamlessly into a spectacular stone fireplaced 2-story family room, ideal for everyday living and entertaining. Elegant Formal living and Dining rooms and a private French-door study offer comfort, flexibility, and versatility. The luxurious primary suite is a private sanctuary complemented by a spa-inspired bath, inviting sitting area and expansive walk-in closet. Three additional carpeted bedrooms and a beautifully updated guest bath provide comfortable accommodations. The lower level provides flexible space for media, a gym, or recreation space. Outdoors, beautifully landscaped grounds unfold to a generously proportioned composite deck, custom fire pit —ideal for effortless entertaining and enjoying the peaceful setting w/a spacious storage shed. Energy-efficient geothermal heating and cooling provides year-round comfort and exceptional energy performance. Convenient to top-rate schools, minutes to highways, and the commuter rail — a truly special home with room for everyone.

14 Iarussi Way, Medway

$1,199,000

4 Beds ⋅ 4 Baths ⋅ 73577435 MLS

Just reduced! Exceptional Outdoor Living in Medway! Discover this impressive custom-built, approximately 4,430-square-foot residence featuring 4 bedrooms, 3.5 bathrooms, and outstanding indoor and outdoor living spaces. The inviting kitchen offers stainless steel appliances, stone countertops, and a center island, flowing into a welcoming family room with a fireplace. Architectural details and soaring ceilings enhance the home's spacious feel. The outdoor entertaining areas are a standout, featuring an outdoor kitchen, deck and patio, fireplace, multiple fire tables, and a fire pit—perfect for gatherings throughout the seasons. Outdoor furniture is included. The finished lower level with a full bathroom offers additional flexible living space for recreation, a home office, or guests. A three-car garage, central air conditioning, and location within the Medway public school district add to the appeal. Convenient access to major highways and commuter rail options completes this opportunity to enjoy spacious living, exceptional entertaining, and a desirable suburban setting. This distinguished property offers an unparalleled living experience, inviting discerning buyers to discover its refined elegance. Conveniently located close to top rated public schools.

4 Iarussi Way, Medway

$739,500

3 Beds ⋅ 2 Baths ⋅ 73572052 MLS

REDUCED SELLERS SAY SELL You can be in by Thanksgiving 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 3 bedroom ,2full baths 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 bedroom, tiled full bath,2nd bedroom on main level. lower level was recently finished offer a master bedroom suite bed with full bath w/walk in shower and large lounging area .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

$1,174,000

4 Beds ⋅ 4 Baths ⋅ 73571139 MLS

Discover a distinguished single-family residence at 14 Cider Mill Road. This stunning home is located in a beautiful neighborhood, at the end of a Cul-de-sac, which backs up to the Hoag Woods conservation area! 3,387 square feet of refined living space which presents an exceptional opportunity for those seeking an established home designed for both comfort and sophisticated living. The residence features an expansive custom kitchen with large island, new stainless-steel appliances, Quartz counter tops, designer back splash and a bright and sunny dining area that opens up to a huge private backyard. Both heating & HVAC systems are new! The fireplaced Livingroom with custom bookshelves and cabinets is oversized and a great space for entertaining. Second floor offers four well-proportioned bedrooms including the primary ensuite with double walk-in closets and a luxurious bath with beautiful tiled shower and soaking tub. There are also two additional full bathrooms and a half bathroom. Further enhancing the property's appeal is an integrated two-car garage with exterior access providing secure parking and additional storage solutions. The finished basement offers a great office space and large family room with full bath. The expansive 44,606 square foot lot offers a substantial outdoor environment which is professionally landscaped allowing opportunities for personal enjoyment and family gatherings! Great commuter location, top rated schools, dining and more! Solar panels to convey with property.

14 Cider Mill Rd, Medway

$945,000

4 Beds ⋅ 3 Baths ⋅ 73568257 MLS

***Seller will provide a closing cost credit toward buyer’s 3-2-1 temporary mortgage interest-rate buydown, subject to lender approval***Meticulously maintained Colonial on just over an acre at the end of a peaceful cul-de-sac. Nearly 3,000 sq ft with 4 beds/2.5 baths and an open layout connecting the renovated kitchen to a fireplaced living room and an expansive step-up great room. Kitchen updates include painted cabinetry, modern backsplash, smart appliances, and updated smart lighting. Sliders leads to a screened-in porch with an exterior hot tub underneath; the step-up great room features vaulted ceilings and opens to a large deck overlooking the inground pool. First floor offers a private office, formal living room, formal dining room, and half bath. Upstairs: 4 bedrooms including a generous primary suite with walk-in closet, upgraded flooring, solar-powered blinds, and a European toilet. Finished basement with poolside walkout. Smart home features include EV charger, smart locks, and 4 Nest thermostats. Leased solar panels, plus solar-powered exterior security cameras. Recently replaced boiler, heat pump & water tank. Brand new septic Aug 2024. Irrigation, central A/C & 2 car garage. Welcome Home!

16 Jasmine 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

$524,900

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

$899,400

3 Beds ⋅ 3 Baths ⋅ 73562881 MLS

Almost an acre — fenced, gated, and wrapped in trees. Built in 2021. You don't find this in a subdivision. Fruit trees, a storage shed, and room for a garden, a workshop, or whatever you've been waiting for space to do. Inside it's barely broken in: 9' ceilings, hardwood throughout, and an open kitchen with quartz counters, a center island and stainless appliances. The living room has a gas fireplace, custom built-ins and a slider to the deck. Upstairs, the primary suite offers a walk-in closet and double-vanity bath, plus two more bedrooms and second-floor laundry. The finished lower level adds 849 sq ft and a wood stove. What you can't see matters most: spray foam insulation, Pella windows, natural gas heat, central air, 200-amp service, two-car garage — and a whole-house generator transfer switch already wired in. Plug in a generator and the house takes care of itself. Five years old, and you could not rebuild it today for this number.

35 Milford St, Medway

$579,000

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

$619,900

4 Beds ⋅ 2 Baths ⋅ 73553381 MLS

Price reduced 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

$690,000

3 Beds ⋅ 3 Baths ⋅ 73544926 MLS

This first floor primary bedroom contemporary cape is nestled on a wooded lot on a rural street. This home was built and completed in 2022 which Includes 3 large bedrooms and 2.5 baths. This home offers a very versatile floor plan. Enjoy cooking in your gorgeous eat in kitchen with custom cabinetry, granite counters, & stainless appliances. Dining area with bay window and slider to deck overlooking your serene wooded lot. Loft area - perfect for an at home office - overlooks the warm fireside living room with vaulted ceiling. Two bedrooms and full bath on the second floor. Connects to town trails. A minute away from the high school and ball fields. Oversize one car garage under.

58 Adams 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

$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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