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$769,000
2 Beds ⋅ 2 Baths ⋅ 73575558 MLS ⋅ ['Wedgewood Place Condominiums'] BLDG.
Don't miss this beautifully appointed 2-bedroom, 2 bath unit at Wedgewood Place, a waterfront condominium community that is centrally located in downtown Winchester. Magnificent new kitchen with custom cabinets, quartz counter tops and stainless-steel appliances that looks out at a bright and sunny, spacious open living and dining room and small home office area. Featuring a wood burning fireplace and a private balcony with exceptional views of the pool and garden, perfect for your morning coffee. Beautiful wide plank hardwood floors throughout. Custom vanities and quartz counter tops in both bathrooms. The generous Primary bedroom features custom walk-in closet and large en-suite with separate vanity area. Fresh paint and new light fixtures are among the many upgrades. New elevators and upgraded pool. One level living at its best. Enjoy the serene setting of Wedge Pond and park area right next door or take a short stroll to Winchester's amazing shops and restaurants. Public transportation outside your front door, short walk to train, 2 stops, 20 min and you are in Boston. Covered parking! Additional storage in garage.

666 Main St Unit 310, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.
$3,450
2 Beds ⋅ 3 Baths ⋅ 73575497 MLS
Welcome to this spacious 2-bedroom, 2.5-bath townhome in a highly desirable Winchester location with beautiful views of Wedge Pond. Offering multiple levels of living space, this home provides plenty of room to spread out, work from home, and relax.The main level features an open kitchen and dining area, creating a comfortable and functional space for everyday living and entertaining. Step outside to the beautiful private patio, perfect for enjoying your morning coffee, dining outdoors, or simply unwinding.Upstairs, you'll find two generously sized bedrooms, while the home also includes a dedicated office and a fully finished basement, providing flexible additional space for a home office, family room, gym, playroom, or recreation area.Enjoy an excellent location close to Winchester High School, public transportation, and the commuter rail, making travel into Boston convenient. Outdoor enthusiasts will love being near Wedge Pond, with opportunities for fishing, canoeing, and enjoying the waterfront surroundings.With 2 bedrooms, 2.5 baths, an office, finished basement, pond views, outdoor space, and convenient access to transportation, this spacious Winchester rental offers a wonderful combination of location, flexibility, and comfort.

60 Lake Street Unit J, Winchester

Listing courtesy of Listing Agent: Shannon Jenkins from Listing Office: RE/MAX Realty Experts.
$3,000
2 Beds ⋅ 1 Baths ⋅ 73573205 MLS
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. 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 RENT. EASY TO SHOW!

200 Swanton Street Unit T35, Winchester

Listing courtesy of Listing Agent: Nuri Tirana from Listing Office: Tirana Real Estate Group.
$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

Listing courtesy of Listing Agent: Shaundize Moosavizadeh from Listing Office: Coldwell Banker Realty - Boston.
$3,200
2 Beds ⋅ 2 Baths ⋅ 73572062 MLS
Freshly painted and move in ready, 2 bed, 2 bath unit is located in the highly desirable Wedgewood Place. This unit boasts an open concept kitchen, dining and living room complete with a fireplace and alcove perfect for a home office. . The primary suite offers walk in closet closet space and private bath with tub and shower. Second bedroom, additional full bath and washer and dryer complete this unit. Enjoy the convenient location, minutes to public transportation, Winchester Center, schools, library, restaurants and shops while relaxing in the quiet serenity of your covered balcony overlooking the beautiful downtown Winchester. Excellent credit required, first, last, and security, no pets. One covered parking spot included #8.

666 Main St Unit 208, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
$3,895
2 Beds ⋅ 1 Baths ⋅ 73570662 MLS
Beautiful condo style apartment for rent on picturesque Church Street. A lovely 2nd floor unit, generously sized with hardwood floors throughout. Walk upstairs to an open vestibule perfect for reading a good book with direct access to the covered front porch. Living room with faux fireplace opens to a bright and airy home office or a classic dining room with period built-in cabinet. Oversized gas-cooking kitchen, 2bedrooms and full tiled bath finish this welcoming apartment. All new windows and brand new 2nd floor laundry room off the kitchen. Available for occupancy Oct 1st.

77 Church Street Unit A, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$2,500
2 Beds ⋅ 1 Baths ⋅ 73561836 MLS
This great first floor 2 bedroom home is bright and spacious. The entry hall leads to living room, dining room, and kitchen The full bath is flanked by 2 bedrooms. Eat in kitchen with pantry is spacious enough to have a dining table. Tenant pays for gas heat, electricity, hot water, snow removal & refuse removal. Landlord pays for landscaping (grounds maintenance), water, sewer & provides laundry in the basement. 2 car tandem assign parking. Available 9/1/26. Showings are:Wed, 8/12 5-6pmThurs., 8/13 3:30-4:15Fri., 8/14 11am-12 noonPhotos are from 2nd floor unit and represent similar condition and layout.

24 Lebanon Unit 1, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$3,200
2 Beds ⋅ 2 Baths ⋅ 73560790 MLS
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 315-3, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,100
2 Beds ⋅ 2 Baths ⋅ 73560458 MLS
Welcome to this charming 2-bedroom, 1.5-bath rental located on the desirable west side of Winchester. Offering three levels of living space, this home provides plenty of room to spread out and enjoy a comfortable, flexible layout. Beautiful hardwood floors add warmth and character throughout, while the level, partially fenced backyard provides a wonderful private outdoor space for relaxing, entertaining, or enjoying the warmer months. Situated in a welcoming Winchester neighborhood with convenient access to local amenities, schools, shopping, dining, commuter routes, and all that this sought-after community has to offer. Enjoy the space and privacy of a home combined with an excellent Winchester, MA location. Schedule your showing today!

7 Ridge Street, Winchester

Listing courtesy of Listing Agent: Shannon Jenkins from Listing Office: RE/MAX Realty Experts.
$2,800
2 Beds ⋅ 1 Baths ⋅ 73557966 MLS
All utilities included (heat, hot water, and electricity) in this top-floor 2-bedroom, 1-bath condo with stunning views over the treetops and duck pond. Its 7th-floor perch offers exceptional privacy, quiet, and floor-to-ceiling, south-facing windows that fill the home with natural light. One cat allowed. The kitchen and bath were fully renovated several years ago, and the entire unit has been freshly painted. This elevator building features a swimming pool, newly renovated laundry rooms with convenient app-operated machines, and one parking space (additional parking available for a fee). Less than a mile to Winchester Center's cafés, restaurants, shops, and the MBTA commuter rail into Boston. The newly built Lynch Elementary School and grocery store are both approximately ½ mile away. Enjoy quick access to I-93, as well as the scenic trails and natural beauty of Middlesex Fells Reservation and Horn Pond. Available for immediate occupancy. No dogs permitted.

200 Swanton St Unit 705, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.
$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

Listing courtesy of Listing Agent: Elizabeth Darby from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$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

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.
$3,200
2 Beds ⋅ 2 Baths ⋅ 73525728 MLS
LOCATION! LOCATION! LOCATION! Here is your opportunity to live in a quiet and beautifully renovated townhouse in the heart of Winchester, MA. Walking distance to all local schools, parks, downtown shops and restaurants, the commuter rail, tennis courts, and right next to Wedge Pond; where you can enjoy year round fun whether it’s swimming in the summer, or ice skating in the winter. The first floor features granite countertops, stainless steel appliances, hardwood floors, & natural sunlight throughout. With an open concept kitchen and dining room, living room w/ built in shelving and closet, and complete with a half bath. Upstairs you will find 2 spacious bedrooms, one with dual closets and the other w/ walk-in closet and built in shelving. The carpeted lower level is complete w/ a family room, and large laundry room w/ extra storage space. Easy access to Rte 93, 128, and Boston, communal picnic area on site.

60 Lake St Unit D, Winchester

Listing courtesy of Listing Agent: Clara Wu from Listing Office: United Real Estate, LLC.
$3,500
2 Beds ⋅ 1 Baths ⋅ 73516177 MLS
Welcome to 63 Holland St in Winchester! This beautifully renovated 2-bedroom, 1-bath townhome offers the perfect blend of classic charm and modern updates, featuring hardwood floors throughout, recessed lighting, freshly painted interiors, and a stunning new kitchen with quartz countertops and stainless steel appliances. The updated bathroom showcases a walk-in tiled shower with a custom glass door for a sleek, contemporary feel. Additional highlights include an in-unit washer and dryer, private driveway parking, extra basement storage, professional management, and access to a shared backyard space. Water and sewer are included. Conveniently located near shops, restaurants, and public transportation, this home provides comfortable living in one of Winchester's most desirable neighborhoods.

63 Holland St Unit 63, Winchester

Listing courtesy of Listing Agent: Issam Dib from Listing Office: Skyline Realty.
$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

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$450,000
2 Beds ⋅ 1 Baths ⋅ 73496844 MLS
BACK ON MARKET DUE TO FINANCING ! PARKVIEW WINCHESTER CONDOMINIUMS! 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. 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--2:00 PM

200 Swanton Street Unit T35, Winchester

Listing courtesy of Listing Agent: Nuri Tirana from Listing Office: Tirana Real Estate Group.

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