Winchester, MA Real Estate | Winchester, MA Homes for Sale

Stunning custom-built colonial home from 2017! This property boasts an open floor plan with soaring ceilings, abundant natural light, and hardwood floors paired with recessed lighting throughout. The first floor features a spacious layout centered around a show-stopping kitchen, crafted by Bespoke of Winchester, equipped with BlueStar/Sub-Zero stainless steel appliances. A large bedroom with an ensuite bathroom—ideal for an in-law suite or master option—and a half bath/powder room complete the main level. The second floor offers a grand master suite with a luxurious walk-in closet (with an additional washer/dryer hookup) and a spa-inspired ensuite bathroom. Two more bedrooms, each with ensuite baths, and an office space are also located on this level. The extra-deep two-car garage and double driveway provide ample parking. The expansive, private backyard backs directly onto the Fells Reservation, offering a tranquil setting to enjoy nature and entertain.

57 Winford Way, Winchester

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

$2,350,000

6 Beds ⋅ 4 Baths ⋅ 73289247 MLS

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

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.

$849,000

3 Beds ⋅ 3 Baths ⋅ 73289100 MLS ⋅ ['Pepper Hill Estates'] BLDG.

Welcome to this stunning townhouse in Pepper Hill Estates. It features an open floor plan with beautiful hardwood floors and abundant natural light. The kitchen with stainless steel appliances, flows into a spacious living area. With 3 bedrooms plus a guest room/office or playroom, the flexible floor plan caters to your needs.The home also boasts 2 fireplaces, 2.5 bathrooms, and central A/C and heating. Picture windows offer serene views of the conservation land, and the large backyard provides ample space for outdoor activities.Additional highlights include a one-car garage and 3 off-street parking spaces. Recent upgrades over the past 3 years include new appliances, flooring, paint, hot water tank, patio door,garage opener,etc.Conveniently located near Vinson Owen Elementary School, Wright-Locke Farm, Mullen Field, McClennen Park, and Whipple Hill Reserve with its ponds and trails, this home offers easy access to Winchester Town Center, Arlington Heights, and Lexington Town Center.

49 Edward Dr Unit 49, Winchester

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

$3,100,000

5 Beds ⋅ 6 Baths ⋅ 73289050 MLS

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

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

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

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.

$1,200,000

4 Beds ⋅ 3 Baths ⋅ 73288392 MLS

Welcome to 15 Mayflower Road! This property includes 4 bedrooms and 2.5 bathrooms, providing a comfortable living space. The layout features common areas suitable for everyday living and gatherings. The home is in need of some work and updates to fully realize its potential. The neighborhood is welcoming and a good place to establish a home. Consider this property if you're looking for a practical and well-located home in Winchester that offers the opportunity to make it your own.

15 Mayflower Rd, Winchester

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

$2,799,900

5 Beds ⋅ 6 Baths ⋅ 73288292 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.

$3,999,000

6 Beds ⋅ 6 Baths ⋅ 73287578 MLS

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

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 ⋅ ['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

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

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.

$1,899,000

5 Beds ⋅ 3 Baths ⋅ 73287432 MLS

Meticulously maintained 2005 classic hip roof colonial located on a quaint 4 home street close to Winchester center, the Tri-Community bike path, Horn Pond, Packer tennis courts & Wedge pond! Warm and welcoming 10 Room, 5 bed, 2.5 bath home with impeccable finishes throughout. First floor offers a great flow w/ 9 ft ceilings, formal living and dining room with custom architectural details, gourmet eat in chef’s kitchen with custom cherry cabinets, granite counters & Sub Zero & Viking stainless appliances. A large family room w/gas fireplace is perfectly situated off kitchen.The 2nd floor has 4 spacious bedrooms with custom-built closets, including the primary suite w spacious bath, soaking tub & tiled shower. The private 3rd floor flex space showcases high vaulted ceilings, and is plumbed for a 3rd bath. Oversized attached 2 car garage w/ cabinets/built-in storage. Enjoy the sunny 40 ft farmhouse porch off the eat-in kitchen overlooking the charming manicured Beacon Hill-style yard

2 Fairfield Place, Winchester

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

$3,500

2 Beds ⋅ 2 Baths ⋅ 73287414 MLS

A rare opportunity to live at the Willows in Winchester. Fabulous corner unit on 2nd floor with 2 elevators and a private garage. New granite counters in kitchen and both baths. New carpeting just added in the bedrooms and fresh paint thru out. With beautiful hardwood floors, crown moldings, solid granite counters and stainless steel sink and appliances, you will be impressed. Gas fireplace for the cold winter nights and private balcony for the warm weather. In unit washer and dryer. 2 full baths and whirlpool tub for relaxing after your work out in the pool or gym. Large walk in closets offer lots of storage. You will discover that complex is very well maintained and beautiful inside and out. Close to Winchester center, restaurants and the T.Gas heat and central air will you comfortable year round.

7 Conant Rd Unit 24, Winchester

Listing courtesy of Listing Agent: Paul Bettencourt from Listing Office: Beaudoin & Associates, REALTOR®.

$4,600

3 Beds ⋅ 3 Baths ⋅ 73287087 MLS

Beautiful and Spacious 3 bed 2.5 bath available November 1st! 8 Month lease preferred to 06/30/2025. A 2 car garage, central AC and in unit laundry makes for a convenient short term residence. There is a large well maintained yard perfect for outdoor recreation. Amazing craftsmanship throughout and needs to be seen in person. This is one of Winchester's most sought after neighborhoods due to the beauty and quiet of the location. Many of the rooms get lots of natural light. This home is just down the road from Mystic Lake and has easy access to Route 2. No smoking. Pets allowed.

8 Albamont, Winchester

Listing courtesy of Listing Agent: Adam Shoulkin from Listing Office: Gibson Sotheby's International Realty.

$4,500

4 Beds ⋅ 2 Baths ⋅ 73286762 MLS

This is a 4 bedroom, 2 bathroom rental property situated on a corner lot. The first floor living room includes a wood burning fireplace, hardwood floors and the doorway to the spacious three season sunroom. Next you will find the dining room-which is nestled between the living room and the kitchen. The door off the kitchen allows access to the nice backyard space for easy entertaining outside in the warmer weather. There are two bedrooms (or work from home space) and a full bathroom that complete this floor. Upstairs you will find the other two generous sized bedrooms and second full bathroom. Laundry is in the spacious lower level along with plenty of storage space and a bonus finished room. This quaint New England town has everything you need including easy access to 93 and less than 10 miles to downtown Boston. Plenty of coffee shops, restaurants, salons, boutiques, bookstores & more.

70 Canal Street, Winchester

Listing courtesy of Listing Agent: Rebecca Zeng from Listing Office: Quintess Real Estate.

$1,550

1 Baths ⋅ 73286333 MLS

Discover this charming corner studio, featuring a private patio overlooking serene gardens and a tranquil pond. Enjoy the convenience of a private entrance that is easily accessible from the rear parking area. All utilities are included in the rent: heat, hot water, electricity, water/sewer, A/C, and refuse. This unit includes one unassigned parking space, with the option to lease a second space if needed. Ample guest parking is also available. Upgrades to the unit include new vinyl floor planking. Window shades will be replaced before move in. You'll find two large common laundry rooms conveniently located near the unit. Relax at the seasonal in-ground pool. The location is ideal, with easy access to I-93 and I-95, bus routes, the commuter train, and the picturesque downtown Winchester. First and last month's rent, plus a $500 security deposit required at lease signing. Broker fee: one month's rent. No pets. No smoking. Available 10/1. Email for all showing requests.

200 Swanton Street Unit T38, Winchester

Listing courtesy of Listing Agent: Alex Guarino from Listing Office: Lyv Realty.

$4,500

2 Beds ⋅ 2 Baths ⋅ 73285781 MLS

Stunning 2-Bedroom 2-Bathroom beautifully constructed multi-family apartment walking distance to Winchester Center. Pride of craftsmanship is more than evident including top of the line fully applianced custom kitchen. Some features include radiant floor heat, meticulously crafted woodwork and modern fixtures. Entertainment system installed including flat screen TVs and Sonos music system throughout. Close to all major highways and public transportation. Not your typical rental, this home is above and beyond all expectations. A must see!

4 Dix Terrace Unit 4, Winchester

Listing courtesy of Listing Agent: Rachel Ventresca from Listing Office: Greater Metropolitan R. E..

$2,899,999

5 Beds ⋅ 5 Baths ⋅ 73284396 MLS

Stunning cedar shingle Colonial home nestled in sought-after East Hill. As you step inside, you are greeted by an elegant foyer leading to a chef's kitchen with center island, pantry, granite counters, SS appliances and a sun-filled dining area.The kitchen seamlessly flows to a stone deck, perfect for grilling and alfresco dining. Large family room wrapped with windows featuring a stone fireplace, while the dining room has wainscoting and butler's pantry. The living room offers a fireplace and a wet bar leading to a study with French doors opening to a blue stone patio in your private back yard. The second floor offers 5 nicely appointed bedrooms all with custom closets, the private primary suite has 2 walk-in closets and a large bath. A finished lower level provides additional flexible living space with a full bath and storage room. Views from every room. So many outdoor spaces to enjoy including a turf sports court, large driveway, 3 Car garage with EV charger. Walk to town center.

50 Lorena Road, Winchester

Listing courtesy of Listing Agent: Leigh Ventura from Listing Office: Compass.

$3,999,000

5 Beds ⋅ 5 Baths ⋅ 73283741 MLS

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.

$2,150

1 Beds ⋅ 1 Baths ⋅ 73282840 MLS

Ready for immediate move in! Bright and sunny unit, just painted, all utilities are included in the rent; heat, hot water, electricity and central air. one bedroom unit at the Parkview Condominium complex has everything you have been looking for in Winchester. Living/Dining combo, large primary bedroom with walk in closet, open kitchen with dishwasher. You’ll love spending summer days by the in-ground pool with its expansive picnic grounds and cabana. Amenities include laundry room, resident and guest parking, elevator, air conditioning, and utilities. Move right in and enjoy all that Winchester offers, Middlesex Fells, Tri-Community Bikeway, Farmer's Market, library, downtown shops and restaurants, commuter rail station, and easy access to downtown Boston. Credit check required by owner.

200 Swanton St Unit 417, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Leading Edge Real Estate.

$7,500

4 Beds ⋅ 3 Baths ⋅ 73282769 MLS

This stunning property features an expansive family room off the kitchen providing the perfect setting for entertaining guests or simply relaxing with your loved ones. The kitchen features modern appliances and a convenient slider that leads to the back deck. Laundry room and easily accessible bedroom/office on the first floor. Retreat to the large primary bedroom, which boasts two walk-in closets, a convenient ensuite bathroom, and room for a relaxing sitting area. The newly renovated basement is a true gem, offering additional living space and versatility for playroom, media room, or home gym. With a dedicated office area complete with its own exterior entrance, this space is perfect for those who desire a separate work area. The entire house is wired for internet access, perfect for working from home. Unique to this property is a fully heated driveway and walkway. You'll enjoy not shoveling!

18 Grant Rd, Winchester

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

$2,995

2 Beds ⋅ 2 Baths ⋅ 73282209 MLS

Right in the heart of Winchester center with its fabulous shops and restaurants, farmers' market, commuter rail to Boston and easy access to all major routes. Water views from your private deck of Wedge Pond and access to its beach and town tennis courts. This top floor unit has lots of natural light and living room sky light. Sliders to private deck. Fireplace for chilly nights and beautiful patio by the pool and garden area. One deeded garage space. Kitchen and both baths have been renovated and have granite counters and stainless steel appliances. Wood floors throughout. King size master bedroom with HUGE walk in closet. Additional storage on ground floor. Come see all that Winchester has to offer besides the excellent schools!

666 Main St Unit 403, Winchester

Listing courtesy of Listing Agent: Sheri O'Connor from Listing Office: Plunkett Properties.

$2,900

2 Beds ⋅ 3 Baths ⋅ 73282174 MLS

This beautifully updated large 2+Bedroom townhouse very close to Winchester Center, boasts amenities including shopping, restaurants, Farmer’s Market, library, award-winning schools, parks, and commuter rail. The renovated kitchen offers custom made cabinets, granite countertops and a breakfast bar. The open kitchen looks onto the large living room, with recessed lighting as well as a ton of natural light. The second floor offers a bright full bath, a bedroom, and a spacious bonus room that would be perfect for a home office, playroom, or guest space. The third-floor master suite is a private retreat featuring a skylight, a custom designed bathroom with skylight and tons of storage. This unit has a full basement family room with spacious closets, a half bath and in-unit laundry room with additional storage. Winchester's Top Rated Schools, Fells Conservation area, and so much more are the perfect place to live! Don't miss this amazing property!

247 Washington St Unit #11, Winchester

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

$1,299,000

4 Beds ⋅ 4 Baths ⋅ 73281019 MLS

Step into this brand-new, luxurious 4-bedroom, 3.5-bathroom townhome, where four levels of sophisticated living await you! An inviting covered porch opens into the grand open floor plan. The elegant living room boasts gleaming hardwood floors and expansive windows that flood the space with natural light. The showstopper kitchen dazzles with gorgeous white cabinetry adorned with exquisite gold details, quartz countertops, and a centerpiece waterfall island. A delightful deck overlooks a fenced-in yard. Upstairs, you'll discover a primary suite highlighted by a board-and-batten wall, a custom closet, and a modern bath. This level also includes an additional bedroom, a full bathroom, and laundry. The top floor offers flexible space ideal for a bedroom or bonus room. The finished lower level features a playroom/media room, another bedroom, and a bath. Move right in and enjoy Winchester with award-winning schools, the fells, bike paths, restaurants, shops, and easy access to Boston.

12 Pine Grove Park Unit 12, Winchester

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

$375,000

1 Beds ⋅ 1 Baths ⋅ 73280945 MLS ⋅ ['Parkview Condominium'] BLDG.

An excellent opportunity for investors or owner-occupants to own a property in picturesque Winchester! Located just a short stroll from Winchester Center's restaurants, shops, and parks, this spacious and sunlit one-bedroom unit at Parkview Condominiums offers stunning views of gardens, ponds, and wildlife from your living room or private balcony. Enjoy the convenience of ample parking, including a large overnight guest lot. The low condo fee covers all utilities—central air, central heat, hot water, water and sewer, electricity—as well as an in-ground swimming pool, elevator, and exterior landscaping and maintenance. With easy access to highways (I-93 and I-95) and everything Boston and Cambridge have to offer, plus a short walk to the commuter rail into Boston, this condo is an exceptional find!

200 Swanton St Unit 422, Winchester

Listing courtesy of Listing Agent: Jack Bruneau from Listing Office: Coldwell Banker Realty - Newton.

$699,000

3 Beds ⋅ 2 Baths ⋅ 73279548 MLS

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. 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

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.

$12,000

5 Beds ⋅ 6 Baths ⋅ 73277494 MLS

Almost entirely new construction (gut renovation) this magnificent Colonial home includes 11 rooms comprised of 5 bedrooms, 4 full baths and 2 half baths with 2 ensuite, a bonus 3rd floor open space with bedroom and bath and a lower level game room with a half bath. The bright, open kitchen with farmhouse sink, center island, separate drink bar and refrigerator and stainless and paneled appliances overlooks the large, level back yard with stone patio. Traditional details include crown moldings, gorgeous hardwood floors. A breezeway connects the heated 2 car garage to the kitchen and provides a large mudroom entry. Originally built in 1938, the builder updated to create a comfortable and state of the art contemporary feel to the home.Overlooking Winter Pond, the home sits on a cul de sac with spectacular views. Close to the new Lynch School expected to be ready for 2025. Perfect venue to entertain or simply enjoy an elegant lifestyle. A short distrance to Horn Pond and trails.

16 Ardley Place, Winchester

Listing courtesy of Listing Agent: Nancy Phillips from Listing Office: Coldwell Banker Realty - Lexington.

$999,000

73277176 MLS

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.

$1,549,000

4 Beds ⋅ 2 Baths ⋅ 73274439 MLS

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 ⋅ ['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.

$9,800

5 Beds ⋅ 4 Baths ⋅ 73274209 MLS

Experience the charm of Winchester in this beautifully maintained and updated home. Offering nearly 5,000 sq. ft. of easy living with 5 bedrooms and 4.5 bathrooms in a delightful Winchester neighborhood, it is nestled upon a west facing knoll on a pretty tree-lined street with an easy walk to the top ranked Vinson Owen Elementary School. This home offers an exceptional location. Designed for comfortable living and elegant entertaining by a master builder, the main level features a custom-designed eat-in chef's kitchen that flows into a generously proportioned family room with a fireplace or to the very private backyard patio. Nearby there's an expansive dining room; perfect for entertaining. Upstairs, the home showcases an impressive master suite complete with a luxurious bath, jacuzzi tub, and a separate dressing room with 5 closets and makeup area, plus three additional bedrooms and and extra ensuite bedroom. Enjoy 2 home offices and a 3 car garage. Live here in comfort and style!

12 0lde Village Drive, Winchester

Listing courtesy of Listing Agent: Stephen DeConto from Listing Office: Cameron Real Estate Group.

$1,219,000

5 Beds ⋅ 3 Baths ⋅ 73273924 MLS ⋅ ['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.

$2,395

1 Beds ⋅ 1 Baths ⋅ 73273445 MLS

ALL Utilities Included. Updated 1 bedroom, 1 bathroom apartment at the desirable Parkview Condominiums. Newer kitchen with stainless steel appliances (stove, fridge, microwave, dishwasher), new bathroom and hardwood floor. The bedroom has a walk-in closet. The apartment unit is conveniently located in the second floor, right off the elevator, quick and easy just one flight of strairs. All utilities are included in the rent. Coin laundry available in the building,extra storage space in the basement, parking, in-ground pool, and bbq picnic area in the premises to enjoy. Close to the supermarket and within a mile to Winchester center, restaurants, and commuter rail. Nice and quiet complex.

200 Swanton St Unit 210, Winchester

Listing courtesy of Listing Agent: Ina Shollo from Listing Office: Cameron Real Estate Group - Framingham.

$5,500

4 Beds ⋅ 4 Baths ⋅ 73271274 MLS

Available now!Great family home in Winchester in the Lynch school district (brand new Lynch School!).There is room for the whole family with 4 bedrooms, 4 full bathrooms, an office, and a fully finished basement Space (1 of the bathrooms is on this level.)There is a large 2-car garage, a big deck, and a fenced backyard to enjoy. It is a very convenient location close to parks and walking trails.Can park up yo 6 cars (2 in Garage) 4 in Driveway.Note: There is a one-month broker fee.Small Dogs Allowed on a case by case basis.

270 Cross St., Winchester

Listing courtesy of Listing Agent: The Abundant Group from Listing Office: Real Broker MA, LLC.

$1,299,000

3 Beds ⋅ 4 Baths ⋅ 73270991 MLS

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 ⋅ ['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 ⋅ ['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.

$2,600

2 Beds ⋅ 1 Baths ⋅ 73267705 MLS

Enjoy easy living at the much sought-after Parkview Condominium complex. This oversized 2 bedroom unit is on the third floor, facing northeast with stunning views of the pond. Open kitchen/dining/living, perfect for entertaining. Living room features a sliding glass door and opens to the large, covered balcony. Granite kitchen with dishwasher, electric cooking, full-size refrigerator, and ample cabinet storage. Ceramic tile bathroom. Two large bedrooms, both with closets. Additional storage in the hallway for both coats and linens. Well maintained association features a laundry room, pond, outdoor picnic area, and seasonal inground pool. Prime Winchester location with easy access to the shops and restaurants on Main Street as well as the MBTA Commuter Rail.

200 Swanton Street Unit 339, Winchester

Listing courtesy of Listing Agent: Jennifer M. Keenan from Listing Office: Keller Williams Realty Boston Northwest.

$2,100

1 Beds ⋅ 1 Baths ⋅ 73266291 MLS

3rd 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 and broker fee due at signing. Renters insurance required.

200 Swanton St Unit 314, Winchester

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

$3,995,000

5 Beds ⋅ 5 Baths ⋅ 73264918 MLS

Stunning Waterfront Estate on Upper Mystic Lake! This exceptional 5-bedroom, 4.5-bathroom home features a brand new chef's kitchen, a spacious family room with high ceilings, a gas fireplace, built-ins, and direct access to a stone patio overlooking a fenced-in level yard with a private dock. Enjoy breathtaking lake views from nearly every room of this beautifully crafted estate. Designed for seamless entertaining, the main level leads into a versatile walk-out lower level, perfect for a home gym, office, or media room, complete with ample storage. The second floor boasts a luxurious primary suite and three additional corner bedrooms, providing an ideal family living environment. This home combines luxury with a tranquil setting, making it ideal for both peaceful family life and vibrant gatherings. Just minutes from Boston, this property offers a rare opportunity to own a spectacular waterfront estate that truly has it all!

6 Robinson Park, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.

$1,559,900

5 Beds ⋅ 2 Baths ⋅ 73263803 MLS

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.

$4,195

2 Beds ⋅ 2 Baths ⋅ 73263526 MLS

Discover a rare opportunity to live in a stunning 2nd floor apartment in Winchester. This generously sized unit features two spacious bedrooms, an office/den, and 1.5 baths. Upon entering, you are welcomed by a large foyer leading to a fireplaced living room and a dining room with a beautiful built-in china cabinet, all showcasing elegant hardwood floors. The updated kitchen, complete with a separate 13x6 breakfast nook bathed in natural light, is perfect for enjoying meals. Additional conveniences include an in-unit laundry, and the office/den space, conveniently located just off the kitchen, includes a half bath. This move-in ready rental is ideal for those looking to downsize or enjoy hassle-free living. Rent INCLUDES all exterior maintenance, snow removal, heat, hot water, trash/recycling and basic cable. Enjoy the benefits of carefree living in a prime location close to the town center, public transportation, and major highways, all while experiencing the charm of Winchester.

75 Church Street Unit 3, Winchester

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

$3,988,000

6 Beds ⋅ 7 Baths ⋅ 73261491 MLS

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.

$1,125,000

3 Beds ⋅ 2 Baths ⋅ 73260439 MLS

Opportunity is Knocking! Attention savvy buyers and investors looking to bring their updates and personal style and make this custom one owner ranch style home their own in the much-anticipated brand new Lynch Elementary School District. You will surely appreciate the large scale of this home with a beautiful fireplace and mantel, hardwood floors and custom moldings throughout. This home flows wonderfully with kitchen, dining room complete with a custom cabinet and a family room all connecting to the super-sized living room and 3 generous bedrooms all on one floor. Additionally, the attic is partially finished with stairs, electric heat and hardwood floors. Complete this project and you can enjoy 2 additional bedrooms or home office and media room. The picturesque backyard oasis includes a 20x40 inground pool which will surely be enjoyed in this beautiful private setting abutting the Lynch School field. Very convenient location and right across the coveted Horn Pond Recreation Area.

253 Pond St, Winchester

Listing courtesy of Listing Agent: Ida M. Bianco from Listing Office: Coldwell Banker Realty - Lexington.

$4,600

3 Beds ⋅ 2 Baths ⋅ 73259870 MLS

perfect single-family home in Winchester’s sought-after neighborhood at condominium pricing. Step inside to a spacious layout of 3 bedrooms, 1.5 bathrooms, and gleaming,hardwood floors throughout. This meticulously maintained and updated home welcomes you with a charming mudroom entry, featuring bead board walls and radiant floor heat. The main floor features a spaciousopen-concept layout where cozy bow window seating augments a sun-filled living room and a generous kitchen with abundant cabinets and counter space. Dining room sliders open to a deck and a tree-linedbackyard that is fully fenced. The 2nd floor boasts a master with a stunning walk-in closet, two more bedrooms, and a full bath. Recent updates include refinished floors, new furnace, new water heater, de-leading,electrical updates, some new appliances, and fresh interior paint— truly move-in ready. Quiet 1-way street! Great family neighborhood that is 1 mile from town and MBTA.

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Zhonghui Zhu from Listing Office: Keller Williams Realty.

$1,429,000

4 Beds ⋅ 4 Baths ⋅ 73258738 MLS

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

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.

$5,900

4 Beds ⋅ 3 Baths ⋅ 73256587 MLS

A one-of-a-kind 1983 built Post and Beam Home in the Vinson-Owen elementary school district. Experience a casual but elegant lifestyle in this custom designed & built home, nestled on a half-acre corner lot. The gourmet Kitchen is a chef’s delight & includes top of the line custom cabinetry, granite countertops, Sub-Zero Refrigerator, double Thermador ovens. With this smartly designed floor plan you can set up for a formal, sophisticated setting and accommodate a play area in view of the kitchen workspace. The second floor has three good-sized bedrooms, and an additional room can serve as a nursery or a home office. The first floor also contains an amply sized bedroom and full bath. The walk-out basement makes an ideal recreation room, office space or exercise room. Lovely details abound in this special home.

32 Surrey, Winchester

Listing courtesy of Listing Agent: Barbara Wales from Listing Office: Engel & Volkers Newton.

$5,300

4 Beds ⋅ 3 Baths ⋅ 73256403 MLS

Experience all that Winchester has to offer in this gracious center entrance Garrison Colonial located on a quiet cul-de-sac just moments from town center, public transit, and schools. The bright and inviting front-to-back living room with fireplace, built-in cabinets, and crown molding sets the perfect scene for serene daily living. Entertain in the elegant dining room with dual built-in hutches that flows seamlessly into the eat-in kitchen outfitted with custom cabinetry and gas range. Spend mornings overlooking the back yard from the screened-in porch and evenings on the patio with family and friends. The spacious primary suite offers ample closet space and a large en-suite bathroom with double vanity. Three additional bedrooms, home office, full bathroom, and laundry room complete the second floor. The partially finished basement offers a family/play room area and plenty of storage. Enjoy restaurants, coffee shops, and local boutiques all within a stone's throw of your front door!

17 Hillside Ave, Winchester

Listing courtesy of Listing Agent: Erica Carson from Listing Office: Coldwell Banker Realty - Lexington.

$3,600

2 Beds ⋅ 3 Baths ⋅ 73250768 MLS

Beautiful and spacious condominium for rent at a desirable condominium complex in Winchester: the Willows. This 2 beds/2.5 baths units features over 1600sqft of floor plan, central AC, three balconies, and two parking spots. Modern amenities such as hardwood floor in living area, in-unit washer/dryer, gas fireplace, and Nest thermostat for temperature adjustment are all the perks that you would enjoy living in this unit. As an added perks, the complex features an in-ground heated swimming pool, fitness room, and spacious Club Room with kitchen for entertaining your extended friends and family. Located within short distance to I-93 highway access, Commuter rail to Boston, downtown Winchester shops, and top-rated Winchester school, this unit truly must be seen!

7 Conant Rd Unit 60, Winchester

Listing courtesy of Listing Agent: Irene Novia Loka from Listing Office: Matahari Real Estate LLC.

$4,599,000

7 Beds ⋅ 9 Baths ⋅ 73248514 MLS

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 ⋅ ['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.

$7,500

5 Beds ⋅ 4 Baths ⋅ 73246303 MLS

From the moment you enter the foyer of this 1910’s Victorian, you will be charmed. The first level features an eat-in kitchen with quartz countertops, LG Cafe appliances, a wine refrigerator, island, and large windows, as well as a living room, den, and half bath. The second level boasts a master suite with skylight, ceiling fan, two walk-in closets with built-ins, a large balcony overlooking the yard, jacuzzi bath, and a second full bath with steam shower. Two additional bedrooms, a second full bath, and a sitting area complete this level. The third level is perfect for fourth and fifth bedrooms or an office and provides additional storage space. The lower level includes a family room, wine cellar, sauna, exercise room and full bath. Enjoy the spacious, private, tree-lined backyard with a large deck and hot tub ideal for entertaining. The home office exits to the deck and backyard, as well as the two-car garage with level 2 EV charger hookup, and laundry. Entire house air conditioned

20 Grove Pl, Winchester

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

$2,498,800

4 Beds ⋅ 4 Baths ⋅ 73243947 MLS

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 ⋅ ['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.

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