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$1,099,000
3 Beds ⋅ 2 Baths ⋅ 73530959 MLS
Charming colonial with lots of character! Step into a welcoming foyer that leads into an open concept kitchen and dining room area. Kitchen is fully equipped along with gas cooking and breakfast bar,front to back living room with a cozy fireplace surrounded by built-ins and slider out to a big sunny deck and crown moldings, french doors from living room lead out to a 4 season sun room perfect for den, home office or playroom area. First floor half bath. Upstairs features 3 well proportioned bedrooms and a full bath, hardwood floors throughout, partially finished basement with bonus room, 2 car garage and ample driveway parking, sunny back yard. Freshly painted exterior,Showings delayed until Tenant moves out. Please schedule starting July 2nd.

150 Cambridge Street, Winchester

Listing courtesy of Listing Agent: Diane Plunkett from Listing Office: Plunkett Properties.
$1,099,000
3 Beds ⋅ 4 Baths ⋅ 73513572 MLS ⋅ ['The Washington Street Condominium'] BLDG.
Experience the best of Winchester with a home that pairs exceptional value with an unbeatable location. Just moments from Winchester Center, enjoy a low-maintenance lifestyle within walking distance of downtown, the commuter rail, and all three school levels. This townhouse-style condo lives like a single-family home, offering space, flow, and flexibility across four finished levels. The open main level seamlessly connects the kitchen, dining, and living areas, highlighted by coffered ceilings, wainscoting, and a beautifully renovated kitchen with stainless steel appliances and modern finishes. Upstairs, the front-to-back primary suite features custom closets and a spa-inspired bath with a soaking tub and glass shower. The finished lower level provides the perfect flex space for a home office, media room, fitness area, or playroom. Complete with two deeded parking spaces, this is effortless living in one of Winchester's most desirable locations.

129 Washington St Unit 129, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.
$1,064,000
4 Beds ⋅ 2 Baths ⋅ 73547513 MLS
Welcome to this meticulously renovated four-bedroom Colonial, ideally situated on a quiet dead-end street just steps from downtown Winchester, the commuter rail, and the newly built Lynch Elementary School. The sun-filled first floor features gorgeous floors, a charming living room, a dining room that opens to a spacious deck, a stunning updated kitchen with new countertops and appliances, as well as a mudroom and a full bath. The fenced backyard is perfect for entertaining. Upstairs, four bedrooms each offer generous closet space. The lower level--with new half bath, new carpet, laundry and storage--is ideal for a media space or playroom. Newer roof, tankless water heater, and a new 200-amp electrical panel provide peace of mind. Close proximity to Horn Pond Reservation, trails, and parks, and easy access to Boston via rail and bus. A rare chance to own a fully updated home in a truly special neighborhood.

46 Clark St, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$999,900
4 Beds ⋅ 2 Baths ⋅ 73541288 MLS
A rare Winchester opportunity under $1M, 258 Cross Street blends timeless character, meaningful updates, everyday function, and exciting long-term upside. Set on a level, fenced corner lot, this 4 bed, 2 bath Colonial offers the space buyers need today with the flexibility to evolve over time. Inside - hardwood floors, crown molding, arched openings, bay windows, and detailed trim add warmth, while the updated kitchen features stone counters, upgraded cabinetry, stainless appliances, gas cooking, and great natural light. Both full baths have been tastefully updated, including a larger bath with double vanity, tiled shower, and soaking tub. Four bedrooms on the upper levels create options for guests, office, fitness, hobbies, or future needs. Brand new AC, central heat, full basement with laundry/storage, patio, fenced yard, shed, and 4-car parking add real utility. Previously prepared conceptual expansion plans are available for review. Minutes from the iconic, and picturesque downtown

258 Cross Street, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.
$999,000
2 Beds ⋅ 2 Baths ⋅ 73497739 MLS ⋅ ['83 Church St Condominiums'] BLDG.
Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal chandeliers & wall sconces. The thoughtfully renovated kitchen features granite countertops, custom cabinetry, stainless steel appliances, & opens to a stylish butler’s pantry complete w/wine fridge, sink, & in-unit washer/dryer. Upstairs, both bedrooms offer HW flooring, updated lighting, & skylight w/shade. Bathrooms have been tastefully updated. Additional highlights include updated electrical, gas line connection, & integrated sound wiring.Includes one car garage, an additional outdoor parking space & basement storage w/bonus cedar closet.Turnkey home near town center, shops & commuter rail.

83 Church Street Unit 15, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$950,000
3 Beds ⋅ 1 Baths ⋅ 73549935 MLS
Warmth, charm, and an exceptional location come together in this inviting 3-bedroom home. Beautiful wood floors, natural woodwork, French doors, and custom built-ins add character throughout. Generous living spaces provide room to gather, relax, and entertain, while the home's classic appeal offers the perfect opportunity to enjoy today or personalize over time. A detached 2-car garage adds convenience and additional storage, and a half bath is located in the unfinished basement. Just 1 mile from Winchester Center, enjoy easy access to restaurants, coffee shops, boutiques, the public library, and commuter options with close proximity to Boston. The recently built elementary school and renovated high school feature state-of-the-art facilities. Nearby Horn Pond offers scenic walking trails, kayaking, birdwatching, and waterfront views.

47 Water Street, Winchester

Listing courtesy of Listing Agent: The Mary Scimemi Team from Listing Office: Leading Edge Real Estate.
$929,900
4 Beds ⋅ 2 Baths ⋅ 73498603 MLS
This Expanded Cape features a fireplace living room, built in bookcases, and glistening hardwood floors throughout. The spacious kitchen has a dining area which opens to the living room for an entertaining atmosphere. The 2nd floor Master bedroom suite has a balcony to enjoy your morning coffee. The inviting 3 season porch with flagstone floor is a nice place for family to congregate and get to gather. The living room, graced with crown molding, offers a welcoming space for relaxation and entertainment. The home features four bedrooms and two full bathrooms, providing ample space for a comfortable lifestyle. The inclusion of a walk-in closet adds a practical and desirable element, offering generous storage and organization. Please come and visit this fine home close to shops, highways and schools!

380 Cross Street, Winchester

Listing courtesy of Listing Agent: Rajive Dogra from Listing Office: Coldwell Banker Realty - Lexington.
$888,000
4 Beds ⋅ 2 Baths ⋅ 73542597 MLS
Charming and Spacious Custom Built Mid-Century Bungalow offers a wonderful opportunity to live in Winchester ! Do you want to send your children to the award-winning public schools? Need an in-law? Generously sized, sun-drenched, freshly painted rooms with hardwood floors and beautiful architectural details, and two fireplaces. A terrific, flat backyard perfect for growing gardens and outdoor fun. A fully finished lower-level creates excellent 2nd living space for your needs. In-town location convenient to the Commuter Rail and all picturesque downtown Winchester offers. Come see all this sweet, unspoiled Mid-Century home on a dead-end street!

84 Oak Street, Winchester

Listing courtesy of Listing Agent: John E. Magazzu from Listing Office: Charlesgate Realty Group LLC.
$849,000
3 Beds ⋅ 2 Baths ⋅ 73555218 MLS
Walkable to nearly everything, 15 Clark St presents and exceptional opportunity to enjoy refined living in one of Winchester's sought-after neighborhoods. This sun-drenched duplex offers 3 bedrooms, 1.5 bathrooms, and approx 1,336 sq ft of thoughtfully curated living space. Rich hardwood and pine floors, soaring natural light, and an effortless flow in layout create a warm and sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester commuter rail, and major routes, this home embodies the very best of Winchester living.

15 Clark St, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.
$849,000
3 Beds ⋅ 2 Baths ⋅ 73553626 MLS
Walkable to nearly everything, 15 Clark St presents an exceptional opportunity to enjoy refined living in one of Winchester's most sought-after neighborhoods. This sun-drenched townhome offers 3 bedrooms, 1.5 bathrooms, and approximately 1,336 sq ft of thoughtfully curated living space. Rich hardwood floors, soaring natural light, and an effortless open layout create a warm yet sophisticated atmosphere. The beautifully appointed kitchen features modern appliances and generous space for everyday living and effortless entertaining. Upstairs, the spacious primary bedroom is complemented by two additional bedrooms ideal for family, guests, or a dedicated home office. Central A/C, second-floor laundry, and off-street parking enhance everyday convenience. Moments from Elliot Park, Middlesex Fells Reservation, top-rated schools, acclaimed restaurants, boutique shopping, Winchester Center commuter rail, and major routes, this home embodies the very best of Winchester living. No HOA fee.

15 Clark St Unit 15, Winchester

Listing courtesy of Listing Agent: Jeffrey Hsu from Listing Office: Coldwell Banker Realty - Milton.
$799,000
2 Beds ⋅ 2 Baths ⋅ 73546074 MLS ⋅ ['50-52 Middlesex St Townhomes'] BLDG.
Completely renovated from top to bottom, this brand-new 2-bedroom, 2-bath condo offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy white oak hardwood floors, a stunning chef's kitchen with quartz countertops and full-height backsplash, Bosch stainless steel appliances, and beautifully designed baths with custom tile and premium Kohler fixtures. Additional upgrades include a new roof, central A/C and heat, recessed lighting, and all-new systems throughout. Winchester is renowned for its award-winning schools, charming New England downtown filled with shops, restaurants, and cafés, easy commuter rail access to Boston, and convenient proximity to major highways—offering the perfect blend of suburban tranquility and city convenience.

50 Middlesex Street Unit 50, Winchester

Listing courtesy of Listing Agent: The North Star Group from Listing Office: Keller Williams Realty Evolution.
$729,000
3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ['Winchester Green'] BLDG.
Ideally located just minutes from vibrant downtown Winchester, this spacious condominium offers easy access to shopping, restaurants, the Farmer's Market, library, award-winning schools, parks, and the commuter rail. The renovated kitchen features custom maple cabinetry, granite countertops, a breakfast bar, and an open-concept layout that flows seamlessly into the living area—perfect for everyday living and entertaining. The second floor includes a full bath, a bedroom, and a versatile bonus room ideal for a home office, playroom, or guest space. The private third-floor primary suite features skylights, a custom-designed bath with a built-in makeup vanity, and generous storage. The finished lower level offers a family room, half bath, oversized closets, and an in-unit laundry area with additional storage. Enjoy easy access to the 2,600-acre Middlesex Fells Reservation, offering miles of scenic walking, running, and biking trails.

247 Washington St Unit 11, Winchester

Listing courtesy of Listing Agent: Heejeong Joo from Listing Office: Coldwell Banker Realty - Lexington.
$700,000
2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.
Great layout and numerous recent improvements make this a wonderful opportunity! Inviting open layout with abundant natural light coming through NEW TRIPLE-PANE WINDOWS and NEW SLIDER for improved energy efficiency and beauty. Kitchen features updated appliances, granite counters with an eating bar and pantry closet; open to living room with fireplace and dining room with new chandelier. Spacious primary bedroom has LARGE WALK-IN CLOSET plus a sink and linen closet before the entry to the water closet where you'll find a large tub. Second bedroom/office has double closet and is across hall from IN-UNIT LAUNDRY and SECOND BATH with shower. Throughout, enjoy CENTRAL AIR and find NEW LIGHT FIXTURES, FRESH PAINT THROUGHOUT, NEW VINYL "WOOD" FLOORING (all recently done in 2026), NEW WASHER AND DRYER 2025 and NEW HOT WATER HEATER (2024). Love the COVERED PARKING in the garage below the building, association POOL, two ELEVATORS plus the convenience of being only one flight of stairs up from the street level. Location near town center, TRAIN, shopping, restaurants, schools and library is superb.

666 Main Unit 211, Winchester

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$649,900
2 Beds ⋅ 2 Baths ⋅ 73543744 MLS ⋅ ['Wedgewood Place'] BLDG.
Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features a walk-in closet, private bath, and separate vanity area, while the second bedroom and updated guest bath provide flexibility for guests or a home office. New hardwood floors & new carpet in bedrooms, in unit laundry, central air, parking, extra storage, and access to the community pool. The professionally managed elevator building. Located near Winchester Center’s restaurants, shops, commuter rail, parks, and everyday conveniences! move right in and enjoy!

666 Main Street Unit 315, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$400,000
2 Beds ⋅ 1 Baths ⋅ 73496844 MLS
SPRING TIME IS COMING! Welcome to this Stunning 2 BR unit on Terrace level with amazing view of duck pond and flowering garden area from private outdoor patio at Parkview Condominiums. Spacious open LR/DR with updated kitchen and bath. Kitchen to include stainless steel appliances, glass tile backsplash, very nice countertops and huge peninsula great for parties. 2 huge bedrooms with lots of closet spaces. Private storage space and laundry in the building. In ground pool and beautiful out door spaces. One off street parking space and huge guest parking lot. Easy access to Rte. I95, Rte. I93, "T" and Boston. Walking distance to shopping, Winchester town center and many more. HEAT , HOT WATER AND ELECTRICITY ARE INCLUDED IN THE CONDOMINIUM FEE. EASY TO SHOW! OPEN HOUSE ON SATURDAY 11: 00 -- 1:00 PM AND SUNDAY 12:00--1:30 PM OFFERS DEADLINE : MONDAY APRIL 20, 2026

200 Swanton Street Unit T35, Winchester

Listing courtesy of Listing Agent: Nuri Tirana from Listing Office: Tirana Real Estate Group.
$364,900
1 Beds ⋅ 1 Baths ⋅ 73500952 MLS ⋅ ['The Parkview Condominium'] BLDG.
Rarely available top-floor (7th floor) condo at the Parkview Condominium Complex! Enjoy easy living in highly desirable Winchester. Well-maintained 1-bedroom condo offers a bright, open-layout, spacious bedroom with an oversized closet. Full bathroom with tiled shower/tub. The Kitchen offers ample cabinet and counter-top space, breakfast bar style which opens to the living area- perfect for dining and entertaining. Large living room with a glass slider leading to a private balcony overlooking a view of beautifully landscaped grounds. Unit also includes 1 parking space, storage space in the basement, and on-site laundry room. Condo fee includes; heat. hot water, electric, A/C, water/sewer, landscape, & snow removal. Other amenities include gated entry, on-site management, plus the swimming pool with picnic/BBQ area. minutes away from town center, shops, restaurants, bus stop, & the commuter rail t-stop. Close to outdoor trails, major highways, and easy access to the city of Boston

200 Swanton St Unit 717, Winchester

Listing courtesy of Listing Agent: Cameron Moniz from Listing Office: Coldwell Banker Realty - Lexington.
$288,750
1 Beds ⋅ 1 Baths ⋅ 73548413 MLS ⋅ ['The Parkview'] BLDG.
Welcome to effortless living in the most desirable community of Winchester. This beautifully updated studio condominium at The Parkview Condominiums offers an exceptional opportunity to own the most affordable home in Winchester. Rarely offered sunny side lobby level. You'll find a thoughtfully renovated interior featuring a stunning new kitchen with white shaker cabinetry, gleaming quartz countertops, stainless steel appliances, and a peninsula that's perfect for casual dining or entertaining. Enjoy your private balcony overlooking peaceful water gardens—the perfect spot to enjoy your morning coffee, unwind with a glass of wine, or dine al fresco. Residents enjoy beautifully landscaped grounds, a sparkling swimming pool, picnic area, two convenient laundries and private parking. Just minutes away is Winchester Center, with its cozy shops, pubs and train to Boston. So many activities so close to home Most exceptional value around. Ideal for a first-time buyer, downsizer or investor.

200 Swanton Unit L8, Winchester

Listing courtesy of Listing Agent: Stephen DeConto from Listing Office: Cameron Real Estate Group.

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