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$1,475,000
4 Beds 4 Baths 73329785 MLS
Welcome to this stunning 4-bedroom, 3.5-bath townhouse, thoughtfully designed and built in 2016. 1st fl features an open-concept layout, the living room seamlessly transitions into the dining area, which opens to a private back deck. The kitchen is a chef's delight, boasting granite countertops, stainless steel appliances, and efficient vent-out ventilation. 2nd fl offers 3 spacious bedrooms, including a luxurious primary suite complete with a walk-in closet and en-suite bathroom featuring a double vanity and a glass-enclosed shower. An additional full bathroom and a convenient washer/dryer are also located on this floor. 3rd fl provides a private retreat with the 4th bedroom and an additional full bathroom, perfect for guests or a quiet workspace. The finished lower level offers versatility, whether you need a recreation room, home office, or extra storage. With walk-out access to the backyard, this space is both functional and inviting. Open house Saturday/Sunday 11am -1pm.

26 Adams Rd Unit 26, Winchester

Listing courtesy of Listing Agent: Wei Wang from Listing Office: WW Real Estate LLC.

$4,995
3 Beds 2 Baths 73328731 MLS
Discover a fantastic opportunity to rent this Top Floor beautifully gut-renovated townhouse located on picturesque Church Street. Just minutes from downtown Winchester, you'll have easy access to an array of restaurants, shopping, community events, and green spaces, along with the seasonal farmers market and Purple Line train access. A charming townhouse features everything brand new, gleaming hardwood floors that highlight the classic architectural details throughout. The spacious kitchen boasts stunning quartz countertops, perfect for culinary enthusiasts. Enjoy the convenience of in-unit laundry, making daily tasks a breeze. With three comfortable bedrooms, this home includes 1.5 baths and gas fireplace, providing ample space for relaxation. Additionally, two off-street parking spots, one garage parking space for compact car, motorcycle or work shop and generous basement storage. Don’t miss out on this inviting rental in a vibrant community—schedule a viewing today

71 Church St Unit 2, Winchester

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

$940,000
2 Beds 3 Baths 73327606 MLS ['Pepper Hill Estates'] BLDG.
Welcome to this move in ready townhouse in Pepper Hill Estates! Enjoy easy living with this stunning open concept home boasting a newer eat-in kitchen, spacious dining room & oversized living room with a wood burning fireplace and floor to ceiling windows that are flooded w/natural light. This main floor also has great closet space, a half bath and a beautiful rear deck to enjoy. The 2nd level features 2 large bedrooms, 2 baths, a walk in storage closet and laundry. The primary bedroom has new high end plush carpeting, 2 large closets and a beautifully updated bathroom with walk in shower and soaking tub. The 2 car garage enters into a nice mudroom w adjacent utility room offering plenty of space for additional storage. This home is situated nicely in the neighborhood w/ flat yard & beautiful natural views from every room. This home has been lovingly maintained and is in perfect, move in ready condition w/ many recent upgrades inside & out including new windows, siding, driveway & more

60 Edward Drive Unit 60, Winchester

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

$2,200,000
5 Beds 4 Baths 73331755 MLS
Tucked away on a dead-end street, 6 Ardley Place blends classic character with modern comforts. Beautifully expanded with a complete renovation & redesign in 2013, this home offers a warm & inviting atmosphere w/elegant finishes throughout. The heart of the home is a stunning chef’s kitchen, featuring a 10 foot walnut island, Viking gas stove, beautiful cabinetry, & flows into the family room w/custom built-ins. Plantation shutters & an impressive wet bar. The dining room, anchored by a classic fireplace, is perfect for gatherings. Upstairs, the serene primary suite is complemented by 2 spacious bedrooms & a convenient laundry room. The 3rd floor offers 2 additional bedrooms w/cozy sitting room, & full bath. Set on over half acre, the home boasts incredible curb appeal, a 2-car garage, a sprawling deck overlooks the beautifully landscaped yard w/a bluestone stone patio & fire pit —ideal for outdoor entertaining. Thoughtfully designed w/warmth & sophistication, this home is a true gem!

6 Ardley Pl, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$2,900,000
5 Beds 5 Baths 73310488 MLS
Exquisitely restored brick Colonial situated in the sought-after Flats neighborhood of Winchester. Boasting refinished hardwood floors, beautiful moldings and trim, and high ceilings throughout, no detail has been overlooked in this meticulous renovation. The gourmet kitchen, featuring high end appliances, is perfect for culinary enthusiasts, while the formal dining room, complete w/ wood-burning fireplace, creates an ideal setting for gatherings. Just off the kitchen, a bar area creates an inviting space for entertaining, while the large working pantry enhances functionality. A newly designed living room w/gas fireplace offers a cozy retreat, & the master suite provides a tranquil escape, boasting a lavish bath & spacious walk-in closet. A 2 car garage, slate roof, copper gutters, patio, & professionally landscaped yard further enhance the property’s appeal. This home showcases thoughtful design & superior craftsmanship, offering a perfect blend of historic character & modern comfort!

64 Wildwood St, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$3,500
2 Beds 3 Baths 73323582 MLS
This bright and sunny townhouse at The Village Condominiums offers a comfortable, convenient lifestyle in a highly desirable community. The home features beautiful white oak hardwood floors throughout and a newly renovated kitchen with granite countertops, a stainless steel farmhouse sink, dishwasher, electric cooktop, and exterior venting. The living room, complete with a wood-burning fireplace, opens to a private patio with views of the Aberjona River. An open railing staircase enhances the airy, spacious feel. The second level includes a generous primary bedroom with an en-suite bath, a second full bath, a second bedroom, and laundry. Carport parking and additional storage are just steps from your front door. The well-established complex offers amenities such as a swimming pool, tennis courts, and meticulously maintained grounds. With easy access to Winchester Center, restaurants, schools, and shopping, this townhouse is a must-see!

171 Swanton St Unit 13, Winchester

Listing courtesy of Listing Agent: Alina Wang Team from Listing Office: Coldwell Banker Realty - Lexington.

$1,600,000
4 Beds 3 Baths 73326415 MLS
Charming, updated carriage house on a private lot, where form meets function in an in-town location. The expansive living room with a fireplace and beam ceiling offers flexibility for dual purposes or a single use. The impressive kitchen boasts a timeless style with a coffee bar, an eat-in breakfast nook, & a convenient peninsula with a six burner stove and Thermador oven. Positioned by a bay window and screened in porch, the nook is flooded with natural sunlight, as is the generously sized dining room which enjoys the afternoon & evening sun for meals & entertaining. French doors open to bluestone patio, ideal for outdoor gatherings with views of the town. The 1st floor family room lends itself for either gatherings, office, or bedroom space. Upstairs, discover 3 spacious bedrooms, sitting area, and a primary suite with its own bath & sun-drenched windows. An inground, heated saltwater pool and 2-car garage completes this perfect home, offering a private oasis for relaxation and fun.

410 Main St, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.

$1,200,000
2 Beds 3 Baths 73274235 MLS ['The Ledges'] BLDG.
Now is the time to make a move! Step into a sophisticated lifestyle as you enter through a charming courtyard into this elegant condo. The beautifully updated kitchen is a standout, featuring granite countertops, cherry cabinetry, and premium new stainless steel appliances—a chef’s dream come true. The open-concept layout is perfect for modern living, with a dining area flowing into the inviting living room. Custom built-ins, a soaring ceiling with skylights, and a spacious deck overlooking a serene creek and vibrant wildlife complete this picture of luxury and tranquility. The first-floor primary suite offers the convenience you’ve been looking for, with a walk-in closet and a spa-like en-suite bath. Upstairs, enjoy a flexible floor plan with a versatile den/bedroom, another bedroom, a full bath, and a loft boasting custom cabinetry. The expansive lower level adds even more space with a family room, walkout access, a private office/flex space, and a generous walk-in closet.

7 Wainwright Rd Unit 22, Winchester

Listing courtesy of Listing Agent: DeWolfe Group from Listing Office: Gibson Sotheby's International Realty.

$1,800
1 Baths 73328463 MLS
A rare opportunity to rent in a prime Winchester location! Desirable private/direct-entry terrace level Studio at the Parkview Condominiums. This updated unit offers convenient walk-out access with a private covered patio perfect for enjoying the outdoors & offers direct views of the duck pond & courtyard gardens. This oversized studio offers ample space for dining, living & bedroom areas! Amenities include a pool for hot summer days and an on-site laundry room. Close to town location with easy access to the grocery store, restaurants, shops & train to Boston. Rent includes all utilities + 1 parking space. No pets. 2 person occupancy maximum. The apartment advertised may no longer be available for rental.

200 Swanton Unit T30, Winchester

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

$2,825,000
5 Beds 6 Baths 73323849 MLS
Tucked away on a quiet sought after neighborhood, just steps away from the Wedgemere Station and Winchester Center, this meticulously maintained 5-bedroom home built in 2018 perfectly blends modern design with refined details, including beautiful coffered ceilings, wainscoting, chair rails, and crown moulding. The 1st floor offers a formal living room, a spacious family room with a fireplace, a gourmet stainless steel kitchen with an expanded dining area, a formal dining room, and a versatile office/guest bedroom with a full bath. Upstairs, the primary bedroom spans front-to-back, featuring 2 custom closets, a spa-like en suite bath & a sitting area. 3 additional bedrooms, a laundry room, and 2 full baths complete the 2nd floor. The 3rd floor provides a bonus room and attic storage, while the finished LL offers a playroom, gym, and a half bath. With an ideal location and luxurious finishes, all you have to do is move in to start enjoying all of Winchester's restaurants and amenities!

16 Wickham Rd, Winchester

Listing courtesy of Listing Agent: The Serrano Team from Listing Office: Leading Edge Real Estate.

$630,000
2 Beds 2 Baths 73247999 MLS ['Wedgewood Place Condominium'] BLDG.
Welcome to 666 Main Street, Unit LV2, Winchester. This beautiful well maintained 2 bedroom, 2 bathroom condominium on the desirable ground level, features a Private Entrance & a Walk Out Patio w/ Wedge Pond views. Enjoy the close distance of all that Winchester Centre has to offer; shops, restaurants, commuter rail & more. Enjoy an updated kitchen w/ stainless appliances & peninsula, separate dining area w/ convenient custom built-ins. Fireplace living room w/ slider to patio. Large primary bedroom w/ walk in closet, full bathroom & extra sink outside the closed-off bathroom. Oversized second bedroom & closet w/ another large full bathroom off of the hall. Central Air, stackable in-unit laundry, a Community Pool, Deeded Storage & a Deeded Garage Parking Space! Very well managed building. Easy access to Routes 128 & 93. Rare find, not to be missed. Freshly painted & ready for a new owner. Owner has not recently lived in the residence & makes no warranties or representations.

666 Main Street Unit LV2, Winchester

Listing courtesy of Listing Agent: Katie DiVirgilio from Listing Office: RE/MAX 360.

$6,000
3 Beds 3 Baths 73312723 MLS
One of a kind 3 bed, 3.5 bath, luxury townhouse in the heart of Winchester Center! Don’t miss out on this home with both luxury & convenience. Top of the line Viking appliances and French doors in the kitchen which draw in natural sunlightthat enhances the hardwood floors & granite countertops. The spacious master bedroom is sure to impress, with its highlighted wall-to-wall fireplace. Each bedroom features its own private balcony. The crown jewel, master bath, is accompanied by top quality fixtures, including multiple rain shower heads Italian handmade bathtub, and one of kindmarble slabs. Heated floors are featured in all baths throughout the house. The house has a surround sound system, as well as a fully operational wet sprinkler, & fire alarm. Hand placed pavers coat the driveway, leading to a heated garage.Located adjacent to the T station, your daily commute is but a breeze. Enjoy your roof deck while taking in a breathtaking view of the cityscape of Winchester.

40 Church Unit B, Winchester

Listing courtesy of Listing Agent: Sarkis James Kavlakian from Listing Office: Real Estate by Hughes & Assoc. Inc..

$4,000
2 Beds 3 Baths 73293542 MLS
Discover the epitome of elegance in this one of one luxury townhome in the heart of downtown Winchester. This home is equipped with endless high-end finishes throughout, as well as a sophisticated open concept design which bathes the home in natural light. Mahogany hardwood floors coat the entire unit, as well as luxurious yet unique floor to ceiling tile in every bathroom. The gourmet kitchen features top-of-the-line fixtures and appliances, sleek granite waterfall countertops, and custom cabinetry, perfect for culinary enthusiasts and entertaining. A combination of preserved historical significance with modern materials make this unit unreplicable. Located steps from vibrant shops, fine dining, parks, and more. This home perfectly combines luxury and convenience. Don’t miss your chance to make this this exceptional property your home!

40 Church Unit 40, Winchester

Listing courtesy of Listing Agent: Sarkis James Kavlakian from Listing Office: Real Estate by Hughes & Assoc. Inc..

$8,500
5 Beds 4 Baths 73293540 MLS
Discover the epitome of elegance in this one of one luxury townhome in the heart of downtown Winchester. This home is equipped with endless high-end finishes throughout, as well as a sophisticated open concept design which bathes the home in natural light. Mahogany hardwood floors coat the entire unit, as well as luxurious yet unique floor to ceiling tile in every bathroom. The gourmet kitchen features top-of-the-line fixtures and appliances, granite waterfall countertops, and custom cabinetry, perfect for culinary enthusiasts and entertaining. This living area opens to a massive private outdoor roof deck, ideal for relaxing or hosting gatherings. Retreat to themaster suite, boasting colossal ceilings, walk-in closets and complete with a stunning master bath sure to impress the most elegant of tastes. Located steps from vibrant shops, fine dining, parks, and more. This home perfectly combines luxury and convenience. Don’t miss your chance to make this exceptional property your home!

40 Church Unit C, Winchester

Listing courtesy of Listing Agent: Sarkis James Kavlakian from Listing Office: Real Estate by Hughes & Assoc. Inc..

$2,025,000
3 Beds 4 Baths 73323471 MLS
Welcome to this exceptional one floor living ranch-style home, a true haven for both luxury living and car enthusiasts. Nestled among towering trees, this expansive property offers the perfect balance of privacy and beauty, with a stunning 4-car garage designed to accommodate your prized vehicles, ample storage space, workshop, home gym or additional living space. With a grand, welcoming entrance that sets the tone for the rest of the property into the spacious family room with standout features, boasting soaring skylights that flood the room with natural light, creating a warm and inviting atmosphere. The unique design elements, including crown molding throughout, add an elegant touch to the home’s refined aesthetic. Whether you’re relaxing in the family room, entertaining in the large open spaces, or enjoying the serenity of the surrounding trees, this home is designed to meet every need.

23 Olde Village Dr, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.

$7,250
4 Beds 4 Baths 73327351 MLS
ELECTRICITY INCLUDED - Gorgeous townhouse with a so much space and great layout! Featuring gas heat and cooking, CENTRAL AIR, PRIVATE FENCED YARD, OFFICE, 4 beds, 3.5 baths & 2 CAR GARAGE with electric car charger! Kitchen with quartz counter tops, stainless appliances, huge pantry, vent hood, built-ins. 4 levels of living space, including a 3rd floor in-law or au pair suite with bed, bath, & living area. Master bed & bath with expansive shower and walk-in closet. 3 heating/cooling zones and NEST thermostats! Mudroom and huge basement storage. On a one-way street, close to Winchester Center, w/charming restaurants, shops, & MBTA train to North Station. Lease that ends in a summer rotation preferred, but not mandatory. Pets considered. First, 1/2 mo security and 1 month agent fee. Credit and background check, proof of ID & income required. Make an appointment today.

89 Hemingway Unit 89, Winchester

Listing courtesy of Listing Agent: Robyn Bonnett from Listing Office: Coldwell Banker Realty - Lexington.

$2,680
2 Beds 1 Baths 73326729 MLS
Welcome to Parkview Condos! Updated 6th floor unit with views of the pond! This condo offers a desirable open concept floor plan with access to a private balcony for easy outdoor enjoyment. Ample closets throughout with additional storage on the lower level. 1 parking space included as well as availability to purchase a second pass. The pool and grounds are beautifully maintained. The condo fee includes heat, hot water and electric! The only utility bill you pay is Cable/Wifi. On-site professional management. Laundry in building. Within walking distance to the Tri-Community Greenway for the biking, running or walking enthusiast. Minutes to Winchester Center with plenty of restaurants, coffee shops and local boutiques. First, last, security $2,000 and broker fee due at signing. Renters insurance required.

200 Swanton St Unit 607, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: Keller Williams Realty Evolution.

$2,532,000
6 Beds 7 Baths 73317225 MLS
Exquisite 6-bed, 6.5-bath residence offers 6,300 sq ft of sophisticated design and luxurious features. The chef’s kitchen boasts dual islands, quartz countertops, Viking appliances, and a sunny breakfast nook perfect for entertaining. The family room with a gas fireplace opens to a deck and landscaped yard for seamless indoor-outdoor living. The first floor includes a guest bedroom or office with a full bath, a mudroom, and a powder room. The primary suite is a true retreat, featuring a spacious walk-in closet & a spa-like bath w/ double vanities, an oversized shower, and a soaking tub. Three additional bedrooms, two full baths, & a laundry room complete this level. The third-floor is ideal as a bedroom or bonus room that includes a full bath. The finished lower level is designed for entertainment & additional living space complete w/ a bedroom, full bath, playroom or office. Enjoy the ease of a two-car garage with mudroom access. Located just 7 miles north of Boston & near the Fells!

20 Bellevue Ave, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.

$1,020,000
3 Beds 2 Baths 73324877 MLS
Nestled at the end of a peaceful cul-de-sac in Winchester, this charming 3-bedroom, 1.5-bath home is a must-see. Recently updated with fresh paint, modern flooring, stylish lighting fixtures, and updated stainless steel appliances in the kitchen, it blends comfort with convenience. The living room features a cozy wood-burning fireplace, perfect for chilly evenings. The walk-out basement offers endless possibilities—finish it to create a family room or in-law suite! The partially fenced yard provides privacy and space for outdoor activities. Located just minutes from Winchester Center, enjoy easy access to dining, shopping, and vibrant community events. For outdoor enthusiasts, local biking and walking trails are nearby. Commuters will appreciate the quick access to I-93, making trips to Boston or beyond a breeze. This property is being sold *as is*—a fantastic opportunity for contractors or buyers looking to add their personal touch. Don’t miss out—schedule your showing today!

28 Bellevue Ave, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.

$1,450,000
4 Beds 4 Baths 73324430 MLS
Embrace elegance and convenience with this exquisite townhouse that's been meticulously designed. This residence presents a generous 4-bedroom, 3.5-bathroom, ample space for relaxation and entertainment across its three expansive levels. The heart of this home is the open floor plan, where natural light cascades over fine finishes that align with the rhythm of your daily life. Culinary enthusiasts will delight in the chef's kitchen, showcasing sleek stainless steel appliances, a 36" Verona range, crisp white cabinetry, and gleaming quartz countertops. Upstairs, indulge in the serenity of the primary suite with its walk-in closet, spa-like bathroom, and a balcony. Added conveniences include two dedicated parking spaces and a charming private yard. Situated within the vibrant community of Winchester, it benefits from top-tier schools, a lovely town center, seasonal Farmer’s Markets, a library, and commuter rail access. This is more than a home - it's a lifestyle waiting to be cherished.

48 Water St Unit 48, Winchester

Listing courtesy of Listing Agent: Chris Kostopoulos Group from Listing Office: Keller Williams Realty.

$8,000
4 Beds 4 Baths 73324069 MLS
Located in the desirable Vinson-Owen district of Winchester’s West Side, this stunning property offers a blend of contemporary design, flexible living spaces, and luxurious amenities. Spanning 3,000+ sq ft across multi-level layouts, the home features 4 bedrooms, 4 bathrooms, an additional home office, gourmet kitchen with modern appliances, and open-concept living areas perfect for entertaining. Highlights include master suites with spa-like baths with heated floors, versatile bonus rooms, large entertaining living rooms, and private outdoor spaces on multiple levels with stunning hillside views that feature private vegetable gardens. Additional amenities include upgraded appliances, two-car garages, and access to top-rated schools. 49 Amberwood residence is a balance of elegance and functionality, ideal for modern family living.

49 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Michael Gillespie from Listing Office: Senne.

$2,075
1 Beds 1 Baths 73328202 MLS
Modern 1-Bedroom with Pond Views – Available Now!This bright and newly painted 1-bedroom, 1-bathroom apartment offers stunning pond views and modern updates throughout. The rent includes heat, hot water, electricity, and A/C, providing exceptional convenience. Enjoy a kitchen with granite countertops, stainless steel appliances, and a dishwasher, as well as a sunny living space that opens to a private balcony. Additional features include access to a pool, bike parking, storage, and one included parking spot, with the option to purchase additional parking through the HOA. Move-in requires first, last, security, and a broker fee, along with renters insurance. Book your showing today and make this updated home yours!

200 Swanton St Unit 226, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: Keller Williams Realty Evolution.

$1,650,000
3 Beds 4 Baths 73312376 MLS
TOTAL RENOVATION! Thoughtfully crafted to create a warm and inviting abode. Step inside to discover the completely reimagined first floor with an open concept dining room, sitting room, and show-stopping brand new kitchen with a center island, and a slider leading to a patio, ideal for alfresco dining and entertaining. The first floor also hosts a versatile family room with access to a private deck, a laundry area, and a tastefully designed full bathroom. Venture upstairs to find 3 bedrooms, including a lovely primary suite. The lower level of this home is a true retreat, featuring a rec room with a wine closet, a full bathroom, and access to a covered patio. The fenced-in yard, two patios, and deck provide wonderful outdoor space for leisure and recreation. With brand new electrical, plumbing, windows, and systems, 36 Oneida is truly MOVE-IN READY! Just FOOTSTEPS away from Ambrose Elementary School and playground, and 1 mile from Winchester town center!

36 Oneida Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.

$2,799,000
5 Beds 6 Baths 73292579 MLS
Beautiful & magnificent, this colonial single family offers a perfect blend of timeless elegance and contemporary amenities. Situated at the end of a serene cul-de-sac & private hilltop oasis just minutes from the new Lynch Elementary School opening in 2025. Enjoy proximity to Horn Pond recreation areas & seasonal views of Winter Pond. Featuring 5 Bed,4 Full baths, 2-half with 2 ensuites plus a versatile huge 3rd-floor, and a lower-level game room & half bath. Expansive mudroom with closet connects the heated 2-car garage to a state-of-the-art kitchen featuring a farmhouse sink, large island, separate drink bar plus high-end stainless paneled appliances. The spacious backyard with a stone patio is perfect for outdoor living. Featuring crown moldings, stunning hardwood floors, and advanced heating and cooling system, this home is a masterpiece of design and efficiency, proudly Home Energy Rating Certified. Welcome to your dream home, where history and modernity live in perfect harmony

16 Ardley Place, Winchester

Listing courtesy of Listing Agent: Ann Norberg from Listing Office: Coldwell Banker Realty - Lexington.

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