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17 Charles Rd Unit 17, Winchester
$645,000
2 Beds ⋅ 2 Baths ⋅ 73502587 MLS ⋅ ['Residences At Winchester'] BLDG.
Located in the highly sought-after, newly done Lynch School district, this home shines with fresh paint throughout and beautifully refinished hardwood floors. The first floor offers a functional layout with a dedicated dining area that flows seamlessly to the kitchen and spacious living room—ideal for everyday living and entertaining. The upper level features two generously sized bedrooms and two full bathrooms. Both equip with excellent closet space and ample sunlight through multiple windows. An unfinished basement of roughly 400 square feet provides excellent potential to add living space and value. Enjoy a large and leveled yard professionally maintained by management. Trash removal and exterior maintenance included in the management fee. This attached single family is complete with a private driveway in a convenient location.

17 Charles Rd Unit 17, Winchester

Listing courtesy of Listing Agent: Jessica Later from Listing Office: JL+CoRE.
14 Bradford Rd Unit 14, Winchester
$620,000
3 Beds ⋅ 2 Baths ⋅ 73538704 MLS ⋅ ['Residences At Winchester'] BLDG.
An affordable, 3 bedroom, 1.5 bath townhome at the Residences at Winchester is ready for new owners to make their mark & memories! Located in a quiet neighborhood and part of the new Lynch Elementary School district, this home is part of a duplex and offers an efficient layout and some great perks. Enter to find a large living room with plenty of natural light, which seamlessly flows to the bright kitchen with gleaming black granite counters & a dining area, great for entertaining. Step upstairs to find 3 ample sized bedrooms and a radiant, updated full bath. Hardwood flooring throughout most of the unit, along with energy efficient Harvey windows. Downstairs in the partially finished basement is a sizeable family room, along with storage, and laundry. Enjoy the outdoors in a spacious, flat and private backyard that is maintenance-free because it's covered by the low HOA fee, along with water, sewer & trash removal! Take the opportunity and make Winchester home!

14 Bradford Rd Unit 14, Winchester

Listing courtesy of Listing Agent: Cook Real Estate Partners from Listing Office: Keller Williams Elite.
583 Burt Hill, Winchester
$560,000
5 Beds ⋅ 3 Baths ⋅ 73477596 MLS
Welcome to your move-in-ready sanctuary—where modern updates meet peaceful nature, with a tranquil brook alongside the property for privacy and charm. Enjoy major peace-of-mind upgrades including a BRAND NEW ROOF, NEW 2,500-gallon SEPTIC system, fresh paint, and stylish laminate flooring throughout. The updated kitchen features NEW APPLIANCES and finishes, while the main-level bath feels like a spa with a jetted soaking tub. Versatility shines with an oversized high-ceiling garage and a fully finished walk-out basement complete with its own kitchen, living space, and private entrance—ideal for an IN-LAW SUITE or multigenerational living. Outside, a detached, fully powered and heated “hobby house” offers the perfect workshop, studio, or home office. A rare blend of space, function, and natural beauty—ready to enjoy from day one.

583 Burt Hill, Winchester

Listing courtesy of Listing Agent: Munise Ulker from Listing Office: Homesmart Success Realty.
115 Washington St Unit 3D, Winchester
$519,000
1 Beds ⋅ 2 Baths ⋅ 73424752 MLS ⋅ ['Church Place'] BLDG.
Welcome to Church Place in Winchester. This light-filled one-bedroom condo offers a unique two-level layout with beautiful windows that frame picturesque views of the town. The main level features an airy, open-concept living and dining area, highlighted by a cathedral ceiling in the living room making it perfect for entertaining or enjoying a quiet evening at home. Upstairs, you’ll find a cozy retreat with the bedroom and bath, creating a sense of privacy and comfort. Additional features include in-unit laundry and a designated parking space for everyday ease. Step outside and experience the vibrant lifestyle Winchester has to offer, just moments from the town center with its inviting shops and restaurants, the weekly farmers market, library, town common, and more! Commuters will appreciate the close proximity to the commuter rail, offering quick access to Boston and beyond. This condo blends character, light, and location, making it a perfect place to call home!

115 Washington St Unit 3D, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
22 Oak St Unit 22, Winchester
$452,500
3 Beds ⋅ 1 Baths ⋅ 73468681 MLS
Welcome to Winchester! Ideally located within walking distance of WHS and Winchester Center, this home offers exceptional value in one of the area’s most desirable communities. The main level features a newly renovated kitchen with adjacent living and dining areas, creating a functional and inviting open layout ideal for everyday living and entertaining. The second floor includes three bedrooms and a full bath, with hardwood flooring throughout. A finished basement provides flexible additional space, perfect for a home office, workout area, or bonus room. Off-street driveway parking and a storage shed add everyday convenience. With close proximity to shops, restaurants, parks, and commuter rail access, this property presents a fantastic single-family alternative and an affordable opportunity to enjoy all that Winchester has to offer. Deed-restricted affordable housing sale.

22 Oak St Unit 22, Winchester

Listing courtesy of Listing Agent: Rameel Rana from Listing Office: Advise Realty.
13 Nelson St Unit 13, Winchester
$425,000
3 Beds ⋅ 3 Baths ⋅ 73458027 MLS
This is a great opportunity for a moderate-income eligible family to purchase a home in this beautiful town of Winchester. The duplex has 3 levels of finished living space. Third level is newly finished with a main bedroom suite. Amazing stained-glass windows on the first level, also includes fireplaces in 4 rooms. Loaded with character and charm. See attached application with details regarding deed restrictions.

13 Nelson St Unit 13, Winchester

Listing courtesy of Listing Agent: Karen Morand from Listing Office: MCO Realty Service, LLC.
22 Arthur St Unit 22, Winchester
$414,500
2 Beds ⋅ 1 Baths ⋅ 73522504 MLS
This property is available to and priced for Income Eligible families in 100% of the moderate-income range. See attached application for eligibility requirements. Throughout the tenure of the current homeowner many upgrades have been made to this property. Roof, new porch, updated Electrical, kitchen cabinets, Gas furnace, DE leading, new brick chimney. The exterior of the home is being prepped at this time for brand new paint on siding and trim. Buyers must complete the application attached prior to any showings.

22 Arthur St Unit 22, Winchester

Listing courtesy of Listing Agent: Karen Morand from Listing Office: MCO Realty Service, LLC.
63 Shore Road Unit 35, Winchester
$410,000
73431319 MLS
Be PROUD to park your business in this totally renovated top-floor, corner unit in this special DOWNTOWN WINCHESTER location! The unit boasts two private, tastefully appointed offices and a modern bathroom. The kitchenette area is also sure to impress. One of the most notable features of this property is the pond and downtown views! The conference room is an ideal setting for meetings or gatherings, embodying both sophistication and comfort. Convenience is unparalleled with three parking spaces, including one covered spot, ensuring ease of access to work every day. The building offers an elevator for effortless movement throughout. Don’t miss this opportunity to enjoy going to the office every day—all while impressing your clients and co-workers at the same time!

63 Shore Road Unit 35, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
200 Swanton St Unit T11, Winchester
$397,000
1 Beds ⋅ 1 Baths ⋅ 73427774 MLS ⋅ ['Parkview Condominiums'] BLDG.
OPEN HOUSES CANCELLED !Move right into this immaculate, renovated walk-in condo with an oversized layout and a highly sought-after private terrace patio. Terrace units rarely go on the market—don’t miss this opportunity to purchase a unit in the best location in the building. The sun-filled home offers an eat-in kitchen with granite counters, modern cabinets, newer stainless-steel appliances, and a dining area overlooking the tranquil duck pond and landscaped grounds. Updates include fresh paint, new lighting, bathroom mirror, kitchen tile floor, slider blinds, and gleaming hardwood floors. The spacious living room opens directly to the private patio, perfect for relaxing or entertaining. Enjoy resort-style amenities in this gated community: sparkling pool, BBQ area, storage, laundry close to the unit, and ample parking. A low condo fee covering heat, hot water, A/C, electric, water, and sewer adds exceptional value. Conveniently located near the train, downtown, shops, and restaurants

200 Swanton St Unit T11, Winchester

Listing courtesy of Listing Agent: Shannon Jenkins from Listing Office: RE/MAX Realty Experts.
200 Swanton St Unit 432, Winchester
$382,000
1 Beds ⋅ 1 Baths ⋅ 73409690 MLS ⋅ ['Parkview'] BLDG.
This beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winchester—one of Massachusetts’ most desirable towns. Conveniently located within the building, this bright and inviting unit features a stylish kitchen with granite countertops and modern cabinetry, plus a renovated bathroom with contemporary finishes. Enjoy peaceful views from the private balcony. The well-maintained, gated community includes a pool, picnic area, cabana, on-site laundry, and ample parking. Just minutes to downtown Winchester, the commuter rail to Boston, and highly rated Winchester public schools. Also near local healthcare, dining, shops, parks, and walking trails. The monthly condo fee includes heat, AC, electricity, hot water, water, sewer, swimming pool, landscaping and more! With its unbeatable location and move-in-ready condition, this is one you won't want to miss!

200 Swanton St Unit 432, Winchester

Listing courtesy of Listing Agent: Mark Gilson from Listing Office: Keller Williams Realty.
200 Swanton St Unit T28, Winchester
$355,000
1 Beds ⋅ 1 Baths ⋅ 73450853 MLS
1 bedroom condo in Winchester. This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with access to the community pool and well-kept grounds, all within a short distance of Winchester Center, shops, and public transportation.

200 Swanton St Unit T28, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: RE/MAX Andrew Realty Services.
200 Swanton St Unit 630, Winchester
$340,000
1 Beds ⋅ 1 Baths ⋅ 73463453 MLS ⋅ ['Parkview Condominiums'] BLDG.
Welcome to easy, carefree living in this one-bedroom, one-bathroom condo located in a well-managed Winchester community offering amenities and beautifully maintained grounds. This inviting unit features a private sixth-floor porch with a lovely view of the landscaped grounds, providing a peaceful spot to relax and unwind. The condo fee includes heat, hot water, and electricity, offering value and predictable monthly expenses. The unit also includes one deeded parking space, along with guest parking for visitors. Residents enjoy access to a swimming pool and park-like grounds featuring tranquil ponds, charming bridges, and a pergola, all professionally maintained for year-round enjoyment. Convenient laundry facilities are located within the building, adding to the ease of everyday living. With a functional layout and strong bones, this home offers excellent potential for updates and equity growth, all within a desirable Winchester location!

200 Swanton St Unit 630, Winchester

Listing courtesy of Listing Agent: Angela Hirtle from Listing Office: Lyv Realty.
200 Swanton St Unit 228, Winchester
$330,000
1 Beds ⋅ 1 Baths ⋅ 73459781 MLS ⋅ ['Parkview Condos'] BLDG.
Welcome to Parkview Condos! This one bed one bath, bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with new flooring and excellent closet space, freshly painted throughout all rooms, and on-site laundry. Enjoy community amenities such as an in-ground pool, clubhouse, landscaped grounds, and on-site security. Conveniently located near shopping, schools, restaurants, and major highways. Bedroom and livingroom was virtually staged.

200 Swanton St Unit 228, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
200 Swanton St Unit 636, Winchester
$270,000
1 Beds ⋅ 1 Baths ⋅ 73439236 MLS
Immaculate, studio condominium within the desirable Parkview Condominiums in Winchester. The large private balcony overlooks a beautiful wildlife pond, and the grounds are meticulously landscaped. The kitchen features tile flooring, updated granite countertops, and a breakfast bar. The Condominium amenities include: in-ground swimming pool, barbecue area, large parking area with plenty of overnight guest parking, on-site laundry rooms, on-site management, and private storage units. The low condo fee includes: heat, hot water, trash services, electricity, and air conditioning. Winchester is a quaint and charming New England town, only 8 miles north of Boston. This amazing location is only two blocks from Winchester center, shops, restaurants, parks, and the commuter rail. Don’t miss this exceptional opportunity!

200 Swanton St Unit 636, Winchester

Listing courtesy of Listing Agent: Michael Masci from Listing Office: North Atlantic Realty Group.
200 Swanton Street Unit 234, Winchester
$258,000
1 Baths ⋅ 73455836 MLS ⋅ ['The Parkview'] BLDG.
Sunny studio unit overlooking the pond and courtyard at Parkview Condos in Winchester. Unit features include large private balcony with large sliding door that lets in lots of natural sun light. New LVP flooring in the living room/bedroom area and hallway. Freshly painted all throughout. Kitchen has granite countertops and a new refrigerator and electric range. The condominium amenities include an in-ground swimming pool, barbecue area, large parking area with additional overnight guest parking, on-site laundry, on-site management, and private storage units. Ideally located near downtown Winchester, the commuter rail, and major highways.

200 Swanton Street Unit 234, Winchester

Listing courtesy of Listing Agent: Devin Caglayan from Listing Office: All County Select Property Management.
200 Swanton St Unit 538, Winchester
$250,000
1 Baths ⋅ 73496212 MLS

200 Swanton St Unit 538, Winchester

Listing courtesy of Listing Agent: Michael Masci from Listing Office: North Atlantic Realty Group.
886 Keene Rd, Winchester
$220,000
2 Beds ⋅ 1 Baths ⋅ 73474841 MLS
Your lucky day! Buyers financing fell through so this awsome home is on the market again! Welcome to 886 Keene Rd, a lovingly maintained home where timeless 1875 charm meets thoughtful modern updates. Set on a generous 0.47-acre lot, this property offers space, privacy, and a sense of calm that’s increasingly hard to find.From the moment you arrive, the home makes a warm first impression with classic appeal. A fenced-in front yard creates a welcoming buffer from the road—perfect for pets, gardening, or simply enjoying your own outdoor space. The seller added new gutters to the home. Inside, the home feels cozy and comfortable, offering two well-proportioned bedrooms and a recently remodeled bathroom that adds modern convenience without sacrificing character. The layout is efficient and inviting, ideal for year-round living, a weekend retreat, or a low-maintenance lifestyle. A one-car garage provides both vehicle protection and valuable storag. the septic failed but is still operational

886 Keene Rd, Winchester

Listing courtesy of Listing Agent: Rosemarie Ledogar from Listing Office: R. D. Ledogar Real Estate.

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