Winchester MA Homes For Sale

2 Beds ⋅ 3 Baths ⋅ 73290747 MLS ⋅ NEW Status ⋅ ['Graystone At Winchester'] BLDG.

Discover luxury & convenience in this beautifully maintained 2-3 bed, 2.5-baths in desirable Graystone!! A high end townhome community located just outside Winchester center offering first floor primary suites! The gourmet kitchen showcases custom maple cabinetry, granite countertops, top-of-the-line stainless steel appliances, induction cooking & gleaming hardwood floors. The open-concept living & dining area, complete w/ a gas fireplace & soaring cathedral ceilings with skylights, creates a bright & inviting space. French doors lead to a private, deck & yard—perfect for outdoor relaxation. The spacious first-floor primary suite offers a marble bathroom w/ a custom walk-in shower & generous closet space. Upstairs, an oversized loft area w/ potential to wall off a portion for 3rd bedroom plus an additional second bedroom w/ walk-in closet and full bath. The lower level has extremely high ceilings and offers opportunity for gym/rec room, media room, storage or anything you desire!

22 Graystone Circle Unit 22, Winchester

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

$4,399,000

7 Beds ⋅ 8 Baths ⋅ 73290667 MLS ⋅ NEW Status

Step into this stunning, newly constructed home that redefines modern luxury! Designed w/ both elegance & everyday comfort in mind, this residence blends beauty w/ ease of living. The 8’ arched, handcrafted wrought-iron front doors open to a grand 20' foyer, showcasing soaring 10' ceilings, custom rift-sawn beams, and expansive floor-to-ceiling windows. With 25 years of expertise, the master builder’s commitment to exceptional quality & craftsmanship shines through every detail. Spanning four meticulously finished levels, this home leaves nothing to be desired. Highlights include a chef's kitchen w/ dual islands, vaulted ceilings, 3-bay garage (with space for 6 cars), a charming breakfast nook, butler's & dry pantries, a direct entry first-floor office or in-law suite, & an open, finished attic w/ bath. The expansive lower level offers private entry separate living quarters w/full in-law apartment w/ kitchen, 2nd laundry, bedroom, bath, movie theatre, game room & gym w/flex floor plan!

54 Johnson Road, Winchester

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

$2,890,000

4 Beds ⋅ 4 Baths ⋅ 73290646 MLS ⋅ NEW Status

Beautifully renovated 4 bedroom home in sought after Winchester Flats! Featuring a picturesque combination of stylish comfort and modern design. The 1st floor welcomes with an oversized custom mudroom leading to a spacious chef's kitchen featuring upgraded Wolf appliances including gas range, steam oven, and 2 built-in beverage fridges. The family room invites with custom built-in window seats, vaulted ceiling, and a scenic view of the manicured yard. The dining room impresses with show-stopping wallpaper and wainscoting, while the chic living room and home office with built-in desks create a space for all occasions.The 2nd floor features a beautiful primary suite with walk-in closet and ensuite bath with dual vanity, while 3 more spacious bedrooms, 2 full bathrooms, and laundry room provide the ideal set up for family living. The finished lower level boasts additional living space and ample storage, and outside enjoy the ease of a 2 car garage, large yard, and long driveway. Must see!

56 Salisbury St, Winchester

Listing courtesy of Listing Agent: The McLaren Team from Listing Office: Compass.

$3,895,000

5 Beds ⋅ 5 Baths ⋅ 73290640 MLS ⋅ NEW Status

Experience the epitome of luxury living in this exceptional, high-end renovation of a breathtaking Winchester gem, located in one of the town’s most coveted neighborhoods. Enjoy stunning lake views from numerous rooms & the expansive 1000SF deck! Thoughtfully redesigned by RENEW, a company committed to blending historical integrity with modern design, paying meticulous attention to every detail. This home boasts a new floor plan w/ fabulous kitchen featuring a LaCornue 5 burner stove, 9' Calacatta marble island & fplc w/ adj family rm. 5 spacious bedrooms & 4.5 baths, including a magnificent primary suite w/ marble turret shower. The finished lower level offers a custom wine cellar, perfect for entertaining w/direct entry access to yard. Every detail in this home has been beautifully crafted w/ hand-selected, top-tier finishes throughout. 3-car garage, & close proximity to Winchester's town center, the commuter train to Boston, Mystic Lakes beach, playgrounds & scenic walking trails.

6 Lakeview Road, Winchester

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

$2,350,000

6 Beds ⋅ 4 Baths ⋅ 73289247 MLS ⋅ ACTIVE Status

Welcome to your dream home, nestled in a tranquil cul-de-sac! This property combines luxury and functionality, featuring multiple living areas perfect for entertaining. At the heart of the home is a gourmet kitchen with a Wolf cooktop, dual ovens, two Sub Zero refrigerators, and butler's pantry with a wine cooler—ideal for culinary enthusiasts. The family room boasts cathedral ceilings with a slider leading to the deck that accesses the fenced-in yard. The six spacious bedrooms can comfortably support your family’s needs. Enjoy the convenience of both upstairs and downstairs laundry rooms. The custom gym in the lower level offers an excellent space for fitness enthusiasts, while the additional unfinished square footage can be used to suit your needs as a playroom, media room, or game room. This home also features an electric car charger, catering to eco-conscious living. This property offers everything you need for modern living, combining elegance and practicality in one package!

5 Pilgrim Dr, Winchester

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

$1,570,000

4 Beds ⋅ 3 Baths ⋅ 73289136 MLS ⋅ ACTIVE Status

Located in a wonderful neighborhood, close to schools, downtown Winchester, and the commuter rail, this beloved Victorian home exudes timeless charm and elegance. Its handsome facade features large windows, and a welcoming wrap-around front porch, while the interior has soaring 10-foot ceilings, rich wood floors, and ornate moldings. The living areas are thoughtfully designed to enhance the architectural details, including a spacious living room with beamed ceiling and wood-burning fireplace, dining room with high plate rail and built-in china cabinet, and a cook’s kitchen with gas range, vented hood, stainless appliances, marble counters, and dining area. Highlighting the second floor is the primary bedroom with ensuite bath and walk-in closet, as well as access to a second floor porch overlooking the lush, landscaped back yard. The third floor offers a family/screening room, plus an office, and sleeping nook. Two blocks from the Middlesex Fells hiking trails.

22 Hancock Street, Winchester

Listing courtesy of Listing Agent: Vantage Point Team from Listing Office: William Raveis R.E. & Home Services.

$3,100,000

5 Beds ⋅ 6 Baths ⋅ 73289050 MLS ⋅ ACTIVE Status

Your dream home in the perfect location awaits at a phenomenal new price! This brand-new residence has an unparalleled blend of luxury & comfort. Close to the vibrant town center, schools & train. The stunning open floor plan offers a high-end kitchen anchored by a large island with seating, a dining area & a wet bar with a beverage fridge & ice maker. This flows easily to the spectacular family room with high vaulted ceilings, loads of natural light, a fireplace & access to a spacious deck. A dining room, living room, mudroom & powder room complete this floor. Custom mahogany doors, custom molding, trim, & cabinets will delight any discerning buyer. Upstairs, the large primary suite is an oasis with an elegant large bath, a big walk-in closet & soaking tub. 3 other bedrooms complete this floor, including an en-suite guest room. Third floor is has a 5th bedroom & bath, plus a study or playroom. The basement has a massive media room, wet bar, gym & full bath. Big yard, oversized garage.

59 Bacon St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Leading Edge Real Estate.

$1,999,000

6 Beds ⋅ 4 Baths ⋅ 73288857 MLS ⋅ ACTIVE Status

Step into a world of timeless elegance in this beautifully preserved home, where classic architectural details seamlessly blend with modern comfort. The inviting front porch welcomes you. Inside, high ceilings complement a living room w/beamed ceilings & custom built-ins, a gracious dining room, & a light-filled, eat-in kitchen. The cozy family room offers a charming window seat. A quaint stone patio overlooks a serene, lush backyard, creating your own private oasis! The 2nd floor has 3 spacious bedrms & an updated bath, while the 3rd floor offers 2 more bedrms & a bath. Additional private bedrm w/it's own staircase & bath lends itself to a perfect guest suite. The finished basement adds flexibility for an office, playrm, or gym. With a 2-car garage, exceptional upkeep, & a prime location of just steps to Winchester's vibrant downtown, top-rated schools, & commuter rail, this move-in-ready home is perfect! Outdoor lovers will enjoy the nearby Fells Reservation for hiking & recreation.

7 Herrick St, Winchester

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

$2,599,000

5 Beds ⋅ 5 Baths ⋅ 73288818 MLS ⋅ ACTIVE Status

Stunning new construction! Energy star rated, high efficiency 5 bed 4.5 bath home perfectly situated in a prime East Side location! The first floor welcomes you w/ an open, airy layout, featuring a stylish mudroom, pantry, bath & home office. The gourmet, high-end kitchen flows seamlessly into the living room, complete w/ a cozy fireplace; the dining area extends out to a deck, overlooking a beautifully landscaped yard & patio. The second floor boasts four spacious bedrooms & three full baths, including a lavish primary suite w/ a spa like bathroom. A well-appointed laundry room is also conveniently located on this floor. The third-floor suite is a true retreat, offering two versatile rooms ideal for extended family, office, or lounge, complete w/ a wet bar, an oversized bath & a 5th bedroom with abundant closet space. The expansive lower level adds even more living space, featuring a large family room and an additional full bath, perfect for entertaining. This home truly has it all

50 Winford Way, Winchester

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

$699,999

2 Beds ⋅ 2 Baths ⋅ 73288434 MLS ⋅ ACTIVE Status

Discover your dream home in this bright and airy townhome located in the desirable Villages Condominium. A stunning foyer welcomes you, leading to a spacious living room bathed in natural light from the skylight. Relax by the inviting fireplace or entertain guests in this well-lit space. The home features generous walk-in closets, providing ample storage space. A brand new HVAC system with a two-year warranty ensures your comfort year-round. Just outside, your private patio area awaits, perfect for morning coffee or evening gatherings. Enjoy access to community amenities, including a refreshing pool and well-maintained tennis courts—ideal for active lifestyles. With well-rated schools nearby, you can enjoy peace of mind regarding education. Plus, with the Winchester Town Center just moments away, you’ll have shopping, dining, and entertainment at your fingertips. This townhome offers the perfect blend of comfort, community, and convenience, making it the ideal place to call home!

171 Swanton St Unit 33, Winchester

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

$3,999,000

6 Beds ⋅ 6 Baths ⋅ 73287578 MLS ⋅ ACTIVE Status

This is one of the most notable and distinguished homes on Everett Avenue, with preeminent siting on more than half an acre. Designed by famous architect Robert Coit, this residence combines the magnificence of early 1900s architecture with today's modern amenities. Completely renovated in 2023/2024, this residence features hallmark architectural details including Tudor-style balusters, high ceilings, and a beautiful floor plan centered with a large entrance hall. Large-scale rooms, coffered ceilings, original crown moldings, mantels, and decorative trim are enhanced by the beauty of restored hardwood floors. The brand-new kitchen is a chef's dream with a walk-in pantry w/laundry and refrigerator drawers plus a butler's pantry with a wine fridge. Floor-to-ceiling windows flank the huge family room, overlooking park-like flat grounds. The huge lawn is one of the biggest you can find. Magnificent old oak trees, beautiful birches, and an ample driveway grace this legacy residence.

27 Everett Ave, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Leading Edge Real Estate.

$1,599,000

4 Beds ⋅ 4 Baths ⋅ 73287535 MLS ⋅ ACTIVE Status

Attention buyers/builders looking for a unique opportunity to complete the renovation of this stately 1932 brick colonial in the “The Flats.” This 4 bedroom, 3 1/2 bath home has been partially gutted/framed so the unglamorous work has already been done for you! The 1st floor, which is open down to the studs, plumbed & wired, includes a large living room w/ gas-ready fireplace, home office, kitchen overlooking a deck, mudroom, dining room & half bath. This floor includes new Andersen windows. The 2nd floor features 3 bedrooms w/ hardwood floors. The front-to-back primary suite includes a new bath that has been framed, wired & plumbed. A spacious family bath is plumbed, wired & partially demoed. The basement which includes new Andersen windows, is framed, wired & plumbed & includes a bedroom, family room, full bath, laundry, & storage. Updates include a 3-zone HVAC system (2015), new roof (2014), rebuilt chimney, new Andersen windows, Leafguard Gutters, & Azek trim & deck.

41 Foxcroft Rd, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$279,000

1 Baths ⋅ 73287523 MLS ⋅ ACTIVE Status ⋅ ['Parkview'] BLDG.

A rare opportunity to own in a prime Winchester location! Desirable private/direct-entry terrace level Studio condo at the Parkview Condominiums. This updated sun flied unit offers convenient walk-out access with a private covered patio, perfect for enjoying the outdoors & offers direct views into the duck pond, waterways & courtyard gardens. This unit is larger than many offering ample space for dining, living & bedroom areas with a large walk in closet! Amenities include a pool for hot summer days, a large unassigned parking lot with plenty of guest parking, an on-site laundry room, on-site management, and private storage units. The low condo fee covers heat, hot water, electricity, and air conditioning! Ideal for first-time homeowners, down-sizers, or investors. Close to town location with easy access to the grocery store, restaurants, shops & train to Boston~ This one won’t last!

200 Swanton Street Unit T8, Winchester

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

$1,899,000

4 Beds ⋅ 4 Baths ⋅ 73287487 MLS ⋅ ACTIVE Status

Welcome to this custom-built oversized ranch, cherished & meticulously maintained by the current owners. This idyllic property is situated on a large lot at the end of a cul-de-sac, abutting peaceful conservation land. The main level features grand scale rooms including a spacious eat in kitchen, 2 beautiful living rooms w/ wood burning fireplaces, a stunning dining room for holidays & dinner parties, a home office, laundry & 2 1/2 baths.This home features 2 first floor bedrooms including the spacious primary suite complete with two walk in closets, ensuite bath & a cozy sitting room. The 2nd floor has two additional bedrooms & full bath as well as a large unfinished space w/ plenty of room for expansion. The lower level offers more entertaining space with a custom bar & open space for recreation, movies, etc. Outside, a lovely patio awaits, overlooking conservation where you can relax and enjoy nature. Winchester has top rated schools, a fabulous downtown & is just 7 miles from Boston

5 Thoreau Circle, Winchester

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

$3,200,000

4 Beds ⋅ 5 Baths ⋅ 73287473 MLS ⋅ ACTIVE Status

Meticulously renovated home in desirable Winchester Flats! Set on a tranquil corner lot surrounded by mature trees, less than a mile from schools, Winchester Center, and commuter rail, this exquisite four-level Tudor offers the perfect blend of modern elegance and classic charm. The main level showcases 2 inviting family rooms adorned with fireplace and integrated sound system, gourmet kitchen with Wolf and Subzero appliances, peaceful 3-season porch, and thoughtfully designed mudroom. Ascend to the 2nd floor to discover the primary suite, a peaceful sanctuary featuring a fireplace, cozy sitting area, custom walk-in closet, and ensuite bathroom with dual sinks and zero-entry shower. 2 additional bedrooms with shared bathroom provide ample accommodations for guests or family members, while the 3rd floor offers a private retreat with spacious bedroom and luxurious bathroom with soaking tub. The finished lower level is ideally set up to be used as media room/family room/gym. A must see!

27 Cabot St, Winchester

Listing courtesy of Listing Agent: The McLaren Team from Listing Office: Compass.

$3,899,000

5 Beds ⋅ 5 Baths ⋅ 73283741 MLS ⋅ PRICE CHANGED Status

Nestled on 1.8 acres in Winchester, this fully custom renovated home is truly a hidden gem. Accessing via a winding driveway, the property is completely secluded from the main road, offering a tranquil retreat. Transformed in 2024, this home features 5 spacious beds, 4.5 baths and custom spaces throughout. The grand kitchen, with white oak accents, is a culinary centerpiece. The light-filled family room has expansive windows and a custom marble gas fireplace. A dual sided wood-burning fireplace connects the study and living room. The upstairs study, perfect for office or homework area, has custom built ins. The rec room includes quartz counters and a beverage fridge, ideal for a media room. The primary suite offers a generous walk in closet space and a luxurious bath with dual opposing vanities and a stunning dolomite marble shower. Landscaping features an expansive bluestone patio and thoughtful organic plantings. This rare home is truly an exceptional work of art!

25 Ledgewood Rd, Winchester

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

$549,000

2 Baths ⋅ 73281749 MLS ⋅ ACTIVE Status

Welcome to your new office location in Winchester center. With beautiful views of Judkin Pond, Jenks center and High School. Right next door to the Arthur Griffin Museum of Photography. The views from your office window will amaze you as the seasons change. Enjoy wildlife passing thru on their migratory journey to new adventures. The unit itself is 1617 sq feet of office space. All five individual offices have windows that open to let the fresh breeze and natural light in. The conference room centrally located has floor to ceiling oak built ins. The interior walls for this unit have been sound proofed and go to the decking above. Parking is deeded and this unit comes with three spaces under the building close to the entrance. The waiting room has three desk spaces for admins or para legals. Two private half baths and storage for files or server racks. This unit was custom built for an attorneys office, designed to be private and quiet. Bring your vision and let us see what we can do.

63 Shore Rd Unit 24, Winchester

Listing courtesy of Listing Agent: David Jackson from Listing Office: Leading Edge Real Estate.

$699,000

3 Beds ⋅ 2 Baths ⋅ 73279548 MLS ⋅ ACTIVE Status

Welcome to Winchester ! This townhouse with large backyard is located on lovely tree lined street . The front porch welcomes you as you can sit and watch the world go by. First floor has living room, dining room and kitchen with laundry. Half bath completes the first floor. Three bedrooms and full bath upstairs. One bedroom is a pass through. Back stairway to half of full size attic is off the kitchen. Basement stairs are located off the back entry to full sized unfinished basement. Property being offered "as is". Shared driveway, parking off street in back and large fenced lawn also shared with neighbor. Great location close to schools, commuter line and downtown.

20 Hancock St Unit 20, Winchester

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

$2,799,000

5 Beds ⋅ 5 Baths ⋅ 73279517 MLS ⋅ ACTIVE Status

This exquisite, custom-built home from local master builder boasts a grand two-story foyer, a spacious chef's kitchen seamlessly flows into a vaulted ceiling family room, & an open concept living room & dining room perfect for entertaining. Upstairs, discover a luxurious primary bedroom suite w/expansive walk-in closet & a primary bath featuring double vanities, jacuzzi tub, & a large tiled shower. Two additional well-appointed bedrooms and bathroom complete the 2nd floor, while the 3rd floor offers expansive living w/two ensuite bedrooms, each with a full bath and walk-in closet. Enjoy the high ceilings, detailed custom woodwork, and elegant trim throughout. Additional amenities include central air, central vacuum, deck, & a spacious three-car garage. This stunning home epitomizes elegance and functionality in a prime Winchester location. Nestled near the scenic Fells reservation for outdoor enjoyment & vibrant Winchester center with it's restaurants, shops, farmer's market and more!

92 Hillcrest Pkwy, Winchester

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

$999,000

73277176 MLS ⋅ ACTIVE Status

This commercially zoned property has been recently gutted & offers so much potential, this free standing building offers 4 levels of space with a direct walk out lower level to a large rear parking lot. 4 floor through levels of open space with high ceilings, many windows & great sunlight. This property is located close to Winchester center, restaurants, shops, the MBTA and more! With permission from the town for change of use, this property can potentially be converted to residential/ or mixed use. Buyers to perform their own due diligence. Property has been fully gutted and is need of interior reconstruction but the opportunities are endless! Come take a look today!

968 Main Street, Winchester

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

$50,000

2 Baths ⋅ 73276780 MLS ⋅ ACTIVE Status

Full-service Beauty Salon Business for sale in Winchester. Jumpstart your hair stylist career by taking over a 30-year established business being offered with the entire book of business complete with well known business name, phone number, equipment, clients, and products, and the current 3-year lease locked in at a competitive rate of $2,350 a month which will be transferred to the new owner. Gorgeous ground level salon in a high walking traffic area with a Walk Score of 91. Salon includes 9 styling stations, 3 washing stations, 2 nail booths, 2 bathrooms, a private massage room, an office/break room, and a laundry room with a sink. Large glass windows welcome natural light into the reception area. Enjoy the convenience of a private, shared parking lot for clients plus plenty of on street parking. This is an amazing opportunity to start your own beauty business without the cost of construction or renovating. Potential seller financing available.

746 Main Street, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.

$1,549,000

4 Beds ⋅ 2 Baths ⋅ 73274439 MLS ⋅ ACTIVE Status

Welcome to 28 Thornberry Road, located in Winchester's highly sought-after West Side. Situated on .34 acres, this home has been fully remodeled and is ready for its new owner. The home features four bedrooms plus a bonus room that works perfectly as an office or exercise room, and two full bathrooms. Since the home sits high above the road, you can enjoy complete privacy in your open-concept living, dining, kitchen, and family room spaces. The kitchen features all brand-new appliances as well as quartz countertops. Directly off of the living room, you have a generous-sized, peaceful balcony overlooking your front yard - perfect for coffee in the mornings, or unwinding after a long day at work. Off of the family room to the back of the house, you have a tranquil outdoor patio area. New roof, upgraded electrical and all new windows - this home needs nothing. Get into one of Winchester's top neighborhoods before the school year starts!

28 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Shaundize Moosavizadeh from Listing Office: Coldwell Banker Realty - Boston.

$1,695,000

2 Beds ⋅ 3 Baths ⋅ 73274235 MLS ⋅ ACTIVE Status ⋅ ['The Ledges'] BLDG.

New Price!!! Welcome to an exquisite, turn-key condo where luxury meets comfort. Upon arrival, a charming courtyard sets a serene tone. The stunning, updated kitchen boasts granite countertops, cherry cabinets, and high-end stainless steel appliances. The kitchen seamlessly connects to the dining area and living room, creating a perfect open-concept floor plan. The living room, featuring built-in cabinetry, a soaring ceiling with skylights, and a large deck, offers breathtaking views of a tranquil creek and natural wildlife. The spacious primary suite, located on the first floor, includes a walk-in closet and an updated en-suite bath. The second floor features an office, bedroom, full bath, and a loft space with built-in cabinetry. The lower level offers a spacious family room with walkout access to the yard, a private office/flex space, and a huge walk-in closet with storage space. Indulge in the epitome of sophisticated living in this remarkable residence at The Ledges.

7 Wainwright Rd Unit 22, Winchester

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

$1,219,000

5 Beds ⋅ 3 Baths ⋅ 73273924 MLS ⋅ ACTIVE Status ⋅ ['Cutting House Condominium'] BLDG.

Wonderful turn of the century Victorian townhome in fabulous downtown location! Ideally situated in close proximity to trains, schools, restaurants and everything Winchester Center has to offer! Front porch welcomes you into this lovingly cared for home blending old world charm with modern amenities. First floor features high ceilings, beautiful hardwood flooring, fireplaced living room with pocket doors leading to the sun drenched dining room with builtin cabinet. Updated kitchen with beautiful solid natural cherry cabinets,quartz countertops,Krause sink & stainless steel appliances! Updated 1/2 bath complete w/ radiant flooring rounds out the first floor. Second floor includes 2 bedrooms,an office,a walk in closet & a serene bathroom w/ shower and an oversized jacuzzi tub. Space abounds filled w/ natural light on the third floor featuring 3 bedrooms (1 ensuite), pumpkin wide pine flooring, skylight and a bonus room! Cozy private patio with lovely gardens! Broker tour 8/6 11:30-12:30

89 Mystic Valley Parkway Unit 89, Winchester

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

$1,299,000

3 Beds ⋅ 4 Baths ⋅ 73270991 MLS ⋅ ACTIVE Status

Single Family alternative. Imagine coming home to peace & serenity at The Ledges. Perched on a hilltop on the West side of Winchester, this oasis offers tranquility & carefree living. Day-lilies greet you leading to your private sanctuary with gleaming hardwood floors. Fireplace living room with sliders to your private deck. The main bedroom en suite on the first floor. The second level boasts loft, skylit bonus room for a home office, cedar closet, guest bedroom & full bath. The lower level walk-out features natural light, a guest bedroom and a kitchenette for your extended stays guests or entertaining. After tennis or a long walk, unwind by the pool. Perfect for downsizing without sacrificing space, enjoy stunning views throughout the community. The open floor plan with cathedral ceilings enhances spaciousness & light. Customize this home with your personal touch, start living the life you've always imagined. Don’t delay-seize the opportunity to own a piece of The Ledges today!

7 Wainwright Rd Unit 29, Winchester

Listing courtesy of Listing Agent: Joanne Hofmann from Listing Office: Coldwell Banker Realty - Lexington.

$732,000

2 Beds ⋅ 2 Baths ⋅ 73270797 MLS ⋅ ACTIVE Status ⋅ ['Wedgewood Place Condominium'] BLDG.

Location location. This well maintained two bedroom two bath condominium on one level is a must see. Conveniently located to Winchester Center, Commuter Rail, shops and restaurants makes it very desirable. Enjoy watching the swans swim by while sitting on your patio. Central Air keeps you comfortable during this hot summer. Stackable washer dryer located in the unit for your convenience, Large master bedroom has walk in closet and private bath. The second bedroom is presently used as a den with wall to wall built in bookcases. Recently renovated kitchen invites you to get cooking ! Quartzite Counters, new Bosch refrigerator, Induction stovetop, Whirlpool dishwasher...Custom Cabinets with pull out drawers makes cooking easy. Covered garage offers assigned parking for one car. Complex has a beautiful community pool. Property is well managed. Don't miss out on this opportunity to live in Winchester.

666 Main Street Unit LV3, Winchester

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

$1,299,000

3 Beds ⋅ 4 Baths ⋅ 73268672 MLS ⋅ ACTIVE Status ⋅ ['The Ledges'] BLDG.

Imagine coming home to peace and serenity at The Ledges. Perched on a hilltop on the West side of Winchester, this oasis offers tranquility & carefree living. Day-lilies greet you leading to your private sanctuary with gleaming hardwood floors. Fireplace living room with sliders to your private deck. The main bedroom en suite on the first floor. The second level boasts loft, skylit bonus room for a home office, cedar closet, guest bedroom and full bath. The lower level walk-out features natural light, a guest bedroom and a kitchenette for your extended stays guests or entertaining. After tennis or a long walk, unwind by the pool. Perfect for downsizing without sacrificing space, enjoy stunning views throughout the community. The open floor plan with cathedral ceilings enhances spaciousness and light. Customize this home with your personal touch, start living the life you've always imagined. Don’t delay – seize the opportunity to own a piece of The Ledges today!

7 Wainwright Rd Unit 29, Winchester

Listing courtesy of Listing Agent: Joanne Hofmann from Listing Office: Coldwell Banker Realty - Lexington.

$999,000

2 Baths ⋅ 73268580 MLS ⋅ ACTIVE Status

This commercially zoned property awaits your customization! Recently gutted & offering so much potential, this free standing building offers 4 levels of space with a direct walk out lower level to a large rear parking lot. 4 floor through levels of open space with high ceilings, many windows & great sunlight. This property is located close to Winchester center, restaurants, shops, the MBTA and more! With permission from the town for change of use, this property can potentially be converted to residential/ or mixed use. Buyers to perform their own due diligence. Property has been fully gutted and is need of interior reconstruction but the opportunities are endless! Come take a look today!

968 Main Street, Winchester

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

$1,559,900

5 Beds ⋅ 2 Baths ⋅ 73263803 MLS ⋅ ACTIVE Status

Welcome to this newly renovated contemporary home, nestled in the highly sought-after West-side neighborhood with surprising space! This 3+ level home boasts 4-5 spacious bedrooms and 2 full stylish baths, this home offers versatile space for multiple home offices, in law/ au-pair space plus comfortable family spaces all great for entertaining. The main level features a beautiful open-concept kitchen w/ high end appliances & quartz counters w/ island seating, adjacent dining w/ soaring ceilings, step down the living room w/fplc & walls of glass overlooking large lot w/ patio & fire pit. 4 spacious BR's plus finished LL perfect family/playroom, plus BR #5 or office. Enjoy the convenience of a 2-car garage and additional driveway parking, with ready connections for EV's. Located just minutes from top-rated schools, parks, conservation land, shopping, and a variety of dining options, this home offers the best of suburban living with easy access to downtown Boston in just 15 min! Must see!

7 Thornberry Road, Winchester

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

$3,988,000

6 Beds ⋅ 7 Baths ⋅ 73261491 MLS ⋅ ACTIVE Status

Stunning 8800 sq ft brand-new contemporary in one of Winchester's favorite neighborhoods. A gracious foyer w/ high ceiling welcomes you to this elegant home loaded with natural light and architectural detail. Custom features include a gourmet eat-in kitchen w/ granite countertops, high-end appliances, secondary prep area, and fabulous outside dining options from the oversized deck. The spacious fire-placed family room, banquet-size dining room w/ wine-column, private home office and bedroom w/ en-suite bath complete the first floor. Luxurious primary suite w/a large balcony, expansive walk-in closets & spa-like bath w/ dual vanities, an oversized shower, and a lavish soaking tub on upper level, along w/ 3 additional en-suite bedrooms and an oversized laundry room. Finished lower level features additional entertainment areas, gym & en suite-bedroom. Fantastic location just up the hill from top-rated Vinson Owen School. Enjoy all that Winchester has to offer.

20 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Sino-US Realty Team from Listing Office: Keller Williams Realty.

$1,429,000

4 Beds ⋅ 4 Baths ⋅ 73258738 MLS ⋅ ACTIVE Status

Welcome to this newly constructed luxurious 4-bedroom, 3.5-bathroom townhome spanning four levels of exquisite living space! Step through the charming covered porch into the striking open floor plan. The elegant living room boasts expansive windows, custom fireplace wall and hardwood floors. The showstopper kitchen dazzles with gorgeous white cabinetry accented by gold details, quartz countertops with a centerstage waterfall island. From the dining area, step out onto a delightful deck overlooking a fenced-in yard. Upstairs, find a primary suite which showcases a board & batten wall, custom closet and modern bath, alongside another bedroom, full bath, and laundry room. The top level offers versatile space for a bedroom/bonus room. The fully finished lower level features a playroom/media room, bedroom, full bath, and a convenient mudroom with direct exterior access. Move right in and enjoy all that Winchester has to offer, award winning schools, bike path, fells, easy access to Boston.

14 Pine Grove Park Unit 14, Winchester

Listing courtesy of Listing Agent: Danielle Storella from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$1,429,000

4 Beds ⋅ 4 Baths ⋅ 73257092 MLS ⋅ ACTIVE Status

Welcome to this newly constructed luxurious 4-bedroom, 3.5-bathroom townhome spanning four levels of exquisite living space! Step through the charming covered porch into the striking open floor plan. The elegant living room boasts expansive windows, custom fireplace wall and hardwood floors. The showstopper kitchen dazzles with gorgeous white cabinetry accented by gold details, quartz countertops with a centerstage waterfall island. From the dining area, step out onto a delightful deck overlooking a fenced-in yard. Upstairs, find a primary suite which showcases a board & batten wall, custom closet and modern bath, alongside another bedroom, full bath, and laundry room. The top level offers versatile space for a bedroom/bonus room. The fully finished lower level features a playroom/media room, bedroom, full bath, and a convenient mudroom with direct exterior access. Move right in and enjoy all that Winchester has to offer, award winning schools, bike path, fells, easy access to Boston.

14 Pine Grove Park Unit 14, Winchester

Listing courtesy of Listing Agent: Danielle Storella from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.

$4,599,000

7 Beds ⋅ 9 Baths ⋅ 73248514 MLS ⋅ ACTIVE Status

Unparalleled masterpiece nestled on prestigious Myopia Hill, just 7 miles from Boston! With its awe inspiring architecture and exquisite design this majestic home is sure to captivate you! From the grandeur of the facade, to the breathtaking all new interior set on meticulously manicured grounds w/ carriage house, this home is like nothing you've ever seen. Boasting 15 oversized rooms spanning over 10,000 sf with 13' ceilings, 7 beds/ 8.5 exquisite lavish marble baths w/ oversized showers & indulgent soaking tubs w/ high end bath fixtures. The kitchen offers a 12' island, top of the line appliances, 48' gas range, w/dual dishwashers, custom cabinetry, wine fridge & pantry w/ dining area & stunning family room w/ sliders to the fabulous stone courtyard featuring a built in outdoor kitchen/w grilling station. Enjoy dinner parties for 20 in the grand dining room, step down formal LR, handsome home office, au-pair quarters & and more. A distinguished home for the most discerning buyer!

3 Myopia Road, Winchester

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

$745,000

2 Beds ⋅ 2 Baths ⋅ 73247999 MLS ⋅ ACTIVE Status ⋅ ['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.

$2,498,800

4 Beds ⋅ 4 Baths ⋅ 73243947 MLS ⋅ ACTIVE Status

Experience the pinnacle of refined living at 5 Girard Road, a custom built Contemporary Colonial in Winchester, MA. This captivating home boasts 4 bedrooms and 4 bathrooms. Tasteful architecture and custom woodwork create a timeless and sophisticated ambiance, complemented by an abundance of natural light from oversized windows and skylights. Cathedral ceilings and a Swiss-imported fireplace add grandeur and warmth. Experience the serenity of nature from the comfort of your own home with abundant natural light and picturesque views of the surrounding landscape through expansive windows. The kitchen features timeless maple wood cabinets and a seamless connection to the outdoor entertainment area. The multi-functional basement offers versatile space, while the expansive yard is perfect for seasonal activities. Nearby, Ambrose,Wright-Locke Farm and various outdoor options await. Conveniently located near Whole Foods and Trader Joe's, this home offers elegance, comfort, and natural beauty.

5 Girard Rd, Winchester

Listing courtesy of Listing Agent: Jay Noble from Listing Office: Compass.

$1,045,000

1 Beds ⋅ 2 Baths ⋅ 73242791 MLS ⋅ ACTIVE Status ⋅ ['15 Dix Residences'] BLDG.

Get ready to enjoy one level living with elevator access from heated garage with 2 exclusive use parking spots. This is the place to be for LOCATION, LOCATION, LOCATION AND GARAGE PARKING!!! Inviting, open floor plan features hardwood flooring, large windows, and a generous amount of storage space. Kitchen features large marble topped island with counter seating, gas range and Sub Zero refrigerator. Bedroom has ample storage space (much more than meets the eye!), view of Wedge Pond and large en-suite bathroom with laundry. Office also has full en-suite bathroom. Elegant layout with quality details throughout including a skylight at the entrance. More storage space in garage. Live in town with easy access to commuter rail, shops, restaurants and services. Enjoy everything this great community has to offer: Middlesex Fells Reservation, Wright-Locke Farm, annual community events, Saturday Farmer's Market, a vibrant arts community and more!

15 Dix Street Unit 9, Winchester

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

$1,995,000

6 Beds ⋅ 5 Baths ⋅ 73235871 MLS ⋅ ACTIVE Status

Winchester Estate on Lexington line with your choice of Schools! This Mediterranean inspired home provides the ultimate in large,private,charming space!15 rooms on three living levels.Generous rooms throughout.2 car attached garage with lots of outdoor parking.Large,well appointed 2-tier kitchen ideal for large gatherings and entertaining.Over-sized Dining room with beamed ceiling and connecting bright breakfast room.Dramatic Catherdral Living room with Grand 2-story fireplace leads to 3rd level,upper loft style Study complementing an adjacent home office.6 large bedrooms on both first and second levels.Comfortable,huge first floor family room with oversized stone fireplace.An unequaled space for family,friends,and years of enjoyment.Abutting 100 acres of private,lush conservation land only minutes to beautiful downtown Winchester.Close proximity to corporate hubs in Burlington,Woburn,Waltham and Wilmington.#1 Vinson Owen Elementary School district.Rare lifetime opportunity awaits you!

280 High Street, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.