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28 Olive St, Winchester
$1,049,900
3 Beds ⋅ 2 Baths ⋅ 73595417 MLS ⋅ NEW Status
Welcome to 28 Olive Street, a renovated 3-bedroom, 2-bath ranch in Winchester with 1,783 square feet of finished living space and a top-to-bottom update that lets you move right in. The main level centers on an all-new, slightly expanded eat-in kitchen that opens to an adjacent living room. A wood-burning fireplace and shiplap accent wall anchor the living room. The main living level features refinished hardwood floors, all-new doors, trim, ceilings, and lighting, plus new central AC. Three bedrooms share a completely updated full bath. Downstairs, the finished lower level adds valuable flexible space. The spacious recreation room offers plenty of space for a media area, gym, or home office, plus a second full bathroom, recessed lighting, vinyl flooring, and its own mini-split for heating and cooling. A separate utility room keeps storage, laundry, and mechanicals out of sight. The big-ticket items are done: new roof, windows, siding, electrical service, and exterior doors. The 6,527-square-foot corner lot has a private driveway, new entry stairs, and a crisp new white vinyl fence surrounding the entire property. With the heavy lifting already complete, 28 Olive Street is a rare chance to own in Winchester without the projects. Staging and photos are being done Thursday. First showings are Thursday at the open house. Offers, if any, will be reviewed Monday at Noon.

28 Olive St, Winchester

Listing courtesy of Listing Agent: Ethan Forrest from Listing Office: The Aland Realty Group LLC.
6 Aricia Ln, Winchester
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 73590311 MLS ⋅ ACTIVE Status
Situated on a quiet cul-de-sac in a desirable Winchester neighborhood surrounded by substantial homes, this well-maintained 3-bedroom, 2.5-bath Split-Level offers comfortable living and plenty of potential on a generous 19,998 sq. ft. lot. Built in 1976, the home features hardwood floors throughout and central air conditioning. The main level includes a spacious living room, formal dining room, and eat-in kitchen with access to a screened porch overlooking the backyard. Three bedrooms, including a primary suite with private bath and a renovated family bathroom, complete this floor. The lower level provides additional living space with a family room featuring a fireplace, laundry area, half bath, and direct access to the attached two-car garage. Lovingly cared for over the years, this home is ready to enjoy as is, with room to make it your own over time. Conveniently located near Vinson-Owen School, Wright-Locke Farm, and the Winchester Swim & Tennis Club, it's a great opportunity to settle into one of Winchester's sought-after neighborhoods.

6 Aricia Ln, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
39 Henry Street, Winchester
$850,000
3 Beds ⋅ 1 Baths ⋅ 73585414 MLS ⋅ ACTIVE Status
Exceptional Winchester living awaits at this charming 3-bedroom ranch in the coveted Vinson-Owen district! Offering 1,313 sq. ft. of bright, comfortable space plus basement expansion potential, this home features a classic fireplace living room, formal dining, and a wonderful kitchen. Step outside to a sprawling deck and a lush, private backyard that feels like your own private retreat. Complete with a 2020 roof and 2023 electrical panel, this gem is ready to welcome its next chapter!

39 Henry Street, Winchester

Listing courtesy of Listing Agent: Kelly Batti from Listing Office: Coldwell Banker Realty - Belmont.
258 Cross St, Winchester
$974,900
3 Beds ⋅ 3 Baths ⋅ 73575764 MLS ⋅ ACTIVE Status
Are rates making you feel like home buying is out of reach? The sellers are now offering A TWENTY THOUSAND DOLLAR ($20,000) CREDIT, PERFECT to put towards closing costs or a 2/1 rate buy down. Enjoy over a ONE THOUSAND ($1000) DOLLAR PER MONTH savings year one and over a FIVE HUNDRED ($500) DOLLAR PER MONTH savings year two. A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

258 Cross St, Winchester

Listing courtesy of Listing Agent: Justin Blankenship from Listing Office: Fiv Realty Co.
189 Washington St Unit 2, Winchester
$765,000
3 Beds ⋅ 2 Baths ⋅ 73575116 MLS ⋅ ACTIVE Status
SELLERS WILL PRE-PAY 1 YEAR OF CONDO FEE! 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

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
17 Russell Rd, Winchester
$1,098,000
3 Beds ⋅ 2 Baths ⋅ 73566405 MLS ⋅ ACTIVE Status
Welcome to 17 Russell Rd, a meticulously maintained and updated 3-bedroom, 1.5-bath home in a highly desirable Winchester neighborhood! A charming mudroom with beadboard accents and radiant heated floors welcomes you into a bright open-concept layout with gleaming hardwood floors throughout. Enjoy a sun-filled living room with cozy bow window seating, a spacious kitchen with rich cabinetry, and a dining area with sliders to a private deck and fully-fenced, tree-lined yard. Upstairs features three bedrooms, including a impressive primary suite with a stunning walk-in closet, and a full bath. Major upgrades include deleading (2018), basement asbestos removal (2019), a newer furnace, and a brand-new water heater (2024). Ideally located just 1 mile from Winchester Center, top schools, dining, and the MBTA commuter rail to Boston! Conveniently located near local schools, with easy access for families.AI-generated virtual staging. Furniture and decor are digitally added for illustration purposes only.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..
50 Holland Street, Winchester
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 73556633 MLS ⋅ ACTIVE Status
Private showings available! Resort living just steps from the town center! Completely remodeled with custom finishes throughout, this stunning expanded cape with 3 levels, 3/4 bedrooms, 2.5-baths will exceed your expectations. The first floor features a spacious primary bedroom w/ full bath, an inviting living room w/ beautiful fireplace surrounded & custom built-ins, while the chef's kitchen is designed to impress with high end finishes, a large island and vaulted breakfast nook. The open floor plan flows into the dining room, complete with a custom built-in wine bar, ensuring easy entertaining. The second floor provides two very large bedrooms with great closet space and a tastefully remodeled hall bath. The beautifully finished lower level offers incredible flexibility with a cozy family room, kitchenette, laundry and 1/2 bath, with potential for a 4th BR, making it ideal for entertaining, guests, or extended living space. Step outside to an extraordinary backyard that feels like a resort! Enjoy the professionally landscaped grounds, lush gardens, and an expansive patio creating the ultimate outdoor oasis-featuring a built-in grill, pizza oven, bar seating, a hot tub, greenhouse, and shed. The retractable awnings make for comfortable shaded entertaining. It is truly a backyard that you will use all year round! Ideally located just outside Winchester center, enabling you to enjoy all the benefits of being close to town! This turn-key home is a must see, don't miss this one of a kind, move in ready home with so many recent upgrades!

50 Holland Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
1 Town Way, Winchester
$1,749,000
3 Beds ⋅ 4 Baths ⋅ 73555777 MLS ⋅ ACTIVE Status
Welcome home to this beautifully renovated gem, perfectly positioned on a corner lot in the highly sought-after LINCOLN ELEMENTARY SCHOOL district! Warm, inviting, and truly move-in ready, this home offers the open-concept first floor today’s buyers are looking for—featuring a stunning kitchen that flows effortlessly into the dining and living areas, plus a sunken family room ideal for relaxing or entertaining. Step outside to enjoy the beautifully fenced-in yard, offering a private outdoor retreat for play, pets, gardening, or gatherings. Everyday convenience continues with a mudroom located directly off the driveway, multiple off-street parking spaces, and a two-car garage. The finished lower level includes a full bathroom and versatile flex space perfect for a recreation room, home gym, playroom, or media room. Upstairs, you’ll find three bedrooms, including a lovely primary suite with a spacious bedroom, walk-in closet, and full bath. Thoughtfully renovated from top to bottom, this home features all new systems for peace of mind and effortless modern living. Located just a short walk to Winchester’s vibrant town center and commuter rail.

1 Town Way, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
47 Water Street, Winchester
$899,000
3 Beds ⋅ 2 Baths ⋅ 73549935 MLS ⋅ ACTIVE Status
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.
247 Washington St Unit 11, Winchester
$600,000
3 Beds ⋅ 3 Baths ⋅ 73549877 MLS ⋅ ACTIVE Status ⋅ ['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.
53 Lake Street, Winchester
$1,025,000
3 Beds ⋅ 3 Baths ⋅ 73519082 MLS ⋅ ACTIVE Status
GREAT OPPORTUNITY TO BUILD EQUITY!! LOW PRICE!!! Charming Colonial perfectly blending old world detail with modern updates- ideally located just moments from Winchester Center, Wedge pond, tennis courts, all schools, bike path, the commuter rail, shops & restaurants! This lovingly maintained home w/ central A/C features a spacious, flowing layout, high ceilings & newly refinished hardwood floors. The main level offers a welcoming enclosed entry porch, leading to sun-filled living & dining rooms w/ bay windows. The updated expanded kitchen w/ pantry opens to a bright breakfast room & connects seamlessly to the spacious family rm w/ closets & sliders providing direct access to the expansive multi-tiered decks & private level fenced yard, perfect for entertaining. Upstairs you will find 3 large bedrooms & 2 full baths including a generous primary bedroom w/ walk-in closet. The lower level can be finished for add'l space & includes laundry & storage options. Don't miss this great home complete with EV charger!

53 Lake Street, Winchester

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

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

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