Winchester Condos for Sale

Welcome to Winchester, Massachusetts – a charming town that beautifully blends rich history with modern living. Nestled in Middlesex County, Winchester is known for its picturesque landscapes, vibrant community, and top-notch schools, making it an ideal place for families and professionals alike. With its close proximity to Boston, residents enjoy the tranquility of suburban life while having easy access to the bustling city.

Winchester boasts an array of amenities, including delightful shops, cozy cafes, and lush parks. The town’s historical architecture and tree-lined streets create an inviting atmosphere, perfect for leisurely strolls or weekend outings. The local community is warm and welcoming, fostering a sense of belonging that is hard to find elsewhere.

If you’re considering making Winchester your home, you’ll be pleased to discover a variety of condos for sale that cater to diverse lifestyles. Whether you’re looking for a modern, low-maintenance space or a charming unit with character, Winchester’s condo market has something for everyone. Many of these properties feature contemporary designs, spacious layouts, and amenities that enhance your living experience. Picture yourself enjoying sunny afternoons on a private balcony or hosting friends in a stylish open-concept living area.

With its excellent schools, beautiful surroundings, and a strong sense of community, Winchester is more than just a place to live—it’s a place to thrive. Explore the available condos for sale today and take the first step towards your dream home in this delightful town!

Newest Winchester Condos for Sale

$2,100,000

4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ ['The Ledges'] BLDG.

Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home offers an elegant first-floor primary suite w/ dual walk-in closets and a stunning spa-inspired bath. Meticulously reimagined from top to bottom, every element of this extraordinary renovation was thoughtfully curated using the finest imported designer finishes and bespoke craftsmanship, creating an unparalleled level of luxury. The dramatic open-concept main level is highlighted by soaring vaulted ceilings, a fireplaced living room w/ a custom-designed mantel, & walls of glass that open to a private deck overlooking breathtaking western sunsets & tranquil natural surroundings. The designer kitchen is a true showpiece, featuring premium finishes, a sun-filled breakfast area, & seamless flow into the elegant dining room, ideal for both intimate gatherings & entertaining.The second floor offers 3 rooms including a spacious bedroom, beautifully renovated full bath, loft ideal for a home office, & an additional sitting room/TV room or guest space. The walk-out lower level it’s another suite in itself offering a spacious family room, second kitchenette, dining area, game room, additional bedroom with double closets, a luxurious spa bath, oversized laundry room, and abundant storage. Step outside to a private patio surrounded by peaceful, picturesque grounds, creating the perfect retreat for relaxing or entertaining. Ideally located w/ easy access to Winchester Center, Whole Foods, major highways, restaurants, and shops, this exceptional home offers luxury living just 7 miles from downtown Boston.

7 Wainwright Road Unit 113, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.

$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.

$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.

$1,150,000

3 Beds ⋅ 3 Baths ⋅ 73549484 MLS

Completely renovated in 2021, this stunning 3-bedroom, 2.5-bath townhouse offers the comfort and feel of a single-family home with three levels of beautifully finished living space. The open and inviting floor plan features hardwood floors throughout, modern finishes, and abundant natural light. The spacious third-floor primary suite provides a private retreat with spacious walk in closet and its own full bath. Second floor features 2 ample sized bedrooms, full bath and laundry. Step outside through the sliding glass doors to a newly installed stone patio and backyard—perfect for relaxing, entertaining, or outdoor dining. Additional highlights include two off-street parking spaces and thoughtful updates throughout. Ideally located just moments from the Winchester Center commuter rail station, vibrant downtown shops and restaurants, Winchester High School, and the brand-new Lynch Elementary School, this move-in ready home offers the perfect combination of style, space, and convenience.

52 Salem Street Unit 52, Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$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.

$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.

$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.

$1,299,000

3 Beds ⋅ 3 Baths ⋅ 73534894 MLS ⋅ ['The Ledges'] BLDG.

Waiting for you to enjoy: your carefree home with cathedral ceilings, tall sunny windows, exterior deck, living room with fireplace, formal dining room, adjacent den/3rd bedroom, and kitchen with breakfast area! This "A" style Ledges condominium on a private cul-de-sac includes a FIRST FLOOR PRIMARY SUITE with generous bedroom, large closets and primary bath with double sinks, shower and tub. Spacious single floor living! Plus an upper floor with a loft office space overlooking the living room, and an attractive 2d bedroom suite. The unfinished walk-out basement offers significant room to expand. Landscaping, exterior maintenance, snow removal all done for you while you enjoy the association clubhouse, outdoor pool, tennis court and walking trails in the adjacent Sucker Brook Conservation area. Just minutes from Boston via car or train from charming Winchester Center with its coffee shops, restaurants and outdoor summer dining, pharmacies, and Whole Foods Market all near.

7 Wainwright Road Unit 47, Winchester

Listing courtesy of Listing Agent: Felicity F. Tuttle from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$499,999

2 Beds ⋅ 1 Baths ⋅ 73524262 MLS

Enjoy living in sought-after Winchester, just minutes from Winchester Center, local shops, dining, parks, and commuter access. This beautifully updated two-bedroom condo at Parkview features a modern kitchen with stainless steel appliances, perfect for entertaining, fresh paint throughout, and a bright open-concept layout. Both generously sized bedrooms offer excellent closet space and flexibility for comfortable living. The living area opens to scenic views overlooking the duck pond and professionally maintained grounds, creating a peaceful setting to enjoy year-round. The building offers secure card-entry access, ample resident parking, and guest parking area off Swanton Street. The HOA includes heat, hot water, electricity,AC, and access to the in-ground pool, providing exceptional value and convenience. Unit comes with 1 storage unit in basement.

200 Swanton St Unit 303, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.

$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.

$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.

$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.

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