Winchester Condos for Sale

Winchester Condos for Sale

Welcome to Winchester, Massachusetts, a charming town nestled in Middlesex County that perfectly blends suburban tranquility with easy access to urban amenities. Known for its picturesque landscapes, vibrant community spirit, and top-notch educational institutions, Winchester is an ideal destination for families, professionals, and anyone looking to enjoy a high quality of life.

Rich in history, Winchester boasts a quaint downtown area filled with unique shops, delightful cafes, and a variety of dining options. The town's lush parks and scenic walking trails provide ample opportunities for outdoor enthusiasts to explore nature, while its proximity to Boston ensures that residents can enjoy the cultural and entertainment offerings of the city without sacrificing the peacefulness of suburban living.

For those considering a move to this idyllic town, there are a variety of stunning condos for sale that cater to diverse lifestyles and preferences. These modern residences offer a perfect blend of comfort and convenience, featuring spacious layouts, contemporary finishes, and amenities that enhance everyday living. Whether you’re seeking a cozy one-bedroom retreat or a luxurious multi-bedroom space, Winchester's condo market has something to suit your needs.

Imagine sipping your morning coffee on a sunlit balcony or hosting friends in a stylish open-concept living area—all while being just moments away from Winchester's vibrant community and the bustling city of Boston. Don't miss the opportunity to make this charming town your home. Explore the condos for sale in Winchester today, and discover the perfect blend of suburban charm and urban convenience!

Newest Winchester Condos for Sale

$775,000
3 Beds ⋅ 2 Baths ⋅ 73575116 MLS
Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym, or additional living space. The kitchen opens directly to the generous dining room and features granite countertops, stainless steel appliances, and access to the deck. A full bathroom completes the first level. Upstairs, you’ll find three bedrooms, another full bathroom, and convenient laundry. This spacious home also offers a shared fenced-in yard, off-street parking for two cars, and additional storage in the basement. Abundant public transportation plus the charming shops and restaurants of Winchester Center, as well as elementary, middle, and high schools all at your fingertips. Welcome home to Winchester!

189 Washington St Unit 2, Winchester
$1,300,000
4 Beds ⋅ 3 Baths ⋅ 73574929 MLS
Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street Unit 465, Winchester
$975,000
4 Beds ⋅ 3 Baths ⋅ 73573734 MLS
Enjoy being just a few blocks from Winchester Center in this spacious condo with unique separate guest suite or home office. This single family alternative features 3 bedrooms on the main level and a fourth tucked away in the back of the second floor along with a 3rd bath and kitchenette. Come in the back door from the 1-car garage, or 3 parkings spaces in the driveway, straight into the large, remodeled kitchen with dining area. Appreciate the large windows in the living room. Charming details complement modern improvements. The primary suite is large enough to have an office setup within the space. Primary and hall bath have been updated. Looking for outdoor space? Whether you love the Middlesex Fells, want to have friends over for al fresco dining or do a little gardening, this is the home for you. Condo expenses are split between the 2 units. Town Center, schools, commuter rail, restaurants, shopping and the farmers market are all just a few blocks away. Boston and Cambridge are less than 9 miles away from this spot conveniently located to 93 and 95.

199 Washington Street Unit 199, Winchester
$675,000
2 Beds ⋅ 2 Baths ⋅ 73572854 MLS
Enjoy Winchester living in this spacious 2-bed, 1.5-bath townhouse at the desirable Wedge Pond Condominium. The main level features hardwood floors, a sunny living room, dining room, half bath, and kitchen. On the second level, you have two bedrooms and a full bath. The finished lower level offers more space for a family room, home office, or guest bedroom, plus laundry and storage. To top it all off, you have a private outdoor patio with water views! One deeded parking space included with an additional second space available for $40 per month. Prime location - walk to downtown restaurants, commuter rail, schools, supermarket, beach, and much more. Updates include kitchen (2020) downstairs bathroom (2023) new windows (2026) heating (2020)

60 Lake St Unit E, Winchester
$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
$685,000
2 Beds ⋅ 2 Baths ⋅ 73553517 MLS ⋅ ['Wedgewood Place'] BLDG.
NEW PRICE! 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 Street Unit 211, Winchester
$650,000
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
$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
$789,000
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
$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
$349,900
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
$975,000
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. Some photos are virtually staged.

83 Church Street Unit 15, Winchester
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