Refine Search
Map
Sort by
$11,500
5 Beds ⋅ 3 Baths ⋅ 73570878 MLS
Beautiful newer construction 4/5 bedroom *furnished or *unfurnished home with an attached garage, ideally situated on a gorgeous 11,000+ sq. ft. lot in a wonderful neighborhood with easy access to Route 93 and Boston. This spacious and inviting home offers a flexible floor plan, including a first-floor bedroom with a full bath, perfect for guests, a home office, or additional living space. The heart of the home is the oversized marble kitchen featuring a large center island, stainless steel appliances, gas cooking, and plenty of space for gathering. The kitchen opens to a warm and welcoming family room with a fireplace, while a mudroom provides convenient direct access from the garage. A formal dining room and gleaming hardwood floors complete the main level. Upstairs you’ll find four generously sized bedrooms, including a beautiful primary suite with a soaking tub and separate spa-like shower, plus an additional family room with plantation shutters. Enjoy the private backyard and patio, perfect for entertaining, grilling, and relaxing outdoors. Located in the desirable Muraco Elementary School district and convenient to Winchester Center, commuter routes, shopping, dining, and more. A wonderful opportunity to rent a spacious, beautifully maintained home in Winchester! Flexible lease terms!

10 Bellevue Avenue, Winchester

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

77 Church Street Unit A, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,699,000
5 Beds ⋅ 4 Baths ⋅ 73568493 MLS
Built in 2019 and perfectly positioned near downtown Winchester and the commuter rail, this 5 bed, 3.5 bath Colonial offers a bright, open layout with oversized windows, newly installed custom interior shutters and great natural light throughout. The large living room flows into the dining room, making the first floor great for everyday living and entertaining. The kitchen features a 2025 Thermador appliance package and oversized breakfast nook, with access to the deck, patio and fully fenced yard. Exterior work and fencing were completed in 2022, with mature evergreens and the newer fence creating a private and serene outdoor setting. Upstairs, the spacious primary suite includes a walk-in closet and en-suite bath with soaking tub and standing shower. Two additional bedrooms, a Jack-and-Jill bathroom and laundry room complete the second floor, with two more bedrooms and a full bath on the third. Ample storage throughout the home, including custom closets and additional storage tucked under the eaves on the third floor. Solar panels with Tesla Powerwalls and a HEATED DRIVEWAY are great added features. The unfinished basement with 8'+ ceilings offers excellent potential for future living space.

30 Farrow St, Winchester

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

17 Russell Rd, Winchester

Listing courtesy of Listing Agent: Tsz Mui Kwan from Listing Office: Kwan Realty Inc..
$1,999,000
4 Beds ⋅ 3 Baths ⋅ 73565817 MLS
Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, and an enviable setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High St, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$4,400
3 Beds ⋅ 2 Baths ⋅ 73564765 MLS
Rare opportunity to rent an exceptionally spacious home on historic Church Street in the heart of Winchester! Offering over 2000 sq. ft. of living space, this charming Victorian features 3 generous bedrooms, 1.5 baths, a grand foyer, spacious living and dining rooms, and an eat-in kitchen with granite countertops and gas cooking. High ceilings, hardwood floors, original architectural details and a decorative fireplace add to the home's character. Enjoy a private wraparound farmer's porch, in-unit washer/dryer, ample closet space and two off-street driveway parking spaces. Pet friendly. Ideally located less than half a mile from Winchester Center and approximately 0.3 mile from the commuter rail, with shops, restaurants and cafés nearby. A beautiful combination of space, character and convenience!

79 Church St Unit 1, Winchester

Listing courtesy of Listing Agent: Anna Mean from Listing Office: AC Realty.
$1,880
1 Baths ⋅ 73564703 MLS
Welcome to 200 Swanton Street, Unit 738—a top-floor studio condominium offering comfortable, convenient, and low-maintenance living. All utilities are included, making monthly expenses simple. Enjoy laundry facilities in the building, additional storage downstairs for an extra fee, and a pool.

200 Swanton Unit 738, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
$4,100
4 Beds ⋅ 2 Baths ⋅ 73563763 MLS
This luxurious townhome is now available for immediate occupancy. Spanning two floors, it boasts an exceptional layout. The main floor is particularly impressive, featuring a primary bedroom, an additional bedroom, Open Concept living room and dining area, and a bright, inviting eat-in kitchen. The kitchen is equipped with ample cabinets, counter space, and stainless steel appliances. Natural light floods the home, highlighting the beautiful hardwood floors throughout. The property also includes two full bathrooms, unique spots for multiple work stations or an office, and much more. The Town of Winchester is a commuters dream with easy access to downtown Boston. Either drive or take the MBTA Bus of Commuter Rail Train. Additional amenities include two driveway parking spots, common use of the backyard plus limited basement storage. All applicants must be 18 years of age or older and complete a Rental Application. EXCELLENT credit, income, and references are required. The lease signing requires First month's rent $4,200 and a Security deposit of $4,200.

7 Park Ave Unit 7, Winchester

Listing courtesy of Listing Agent: Christopher L. Barnard from Listing Office: Barnard Real Estate Advisors, LLC.
$3,500
3 Beds ⋅ 1 Baths ⋅ 73563669 MLS
**Flexible lease terms** Prime location close to town! Spacious and beautifully maintained 3-bedroom first floor unit in the heart of Winchester, with a full driveway! This great home offers a blend of classic character and thoughtful updates. This unit has always been owner occupied and is in meticulous condition .. featuring generously sized rooms with high ceilings, oversized windows, hardwood floors, beautiful original woodwork, crown molding, and timeless architectural details. The layout includes a welcoming living room with a wood-burning fireplace, dining room with wainscoting, sunroom, updated kitchen with upgraded cabinets and countertops, and an updated full bath. The kitchen includes a range, dishwasher, refrigerator, and freezer, with washer and dryer also available. Additional features include pantry and storage space, an enclosed porch/patio & a great back yard. Ideally located near downtown Winchester, with convenient access to shops, restaurants, parks, walking and biking trails, schools, public transportation, and the commuter rail. A spacious home combining historic charm, modern updates, and a convenient Winchester location.

303 Washington Street Unit 1, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,295,000
6 Beds ⋅ 7 Baths ⋅ 73563095 MLS
Introducing 2 Atherton Road, an exceptional new construction residence offering over 6,100 sq. ft. of beautifully designed living space with 6 bedrooms, 6.5 baths, and a 3-car garage. A dramatic entry with soaring ceilings and a striking staircase sets the tone for the home’s sophisticated interiors. Designed for both everyday living and entertaining, the open-concept main level showcases an impressive oversized living and dining space that flows seamlessly into the chef’s kitchen, featuring a Thermador appliance package, wine chiller, wet bar, and custom finishes. The adjoining family room is anchored by an electric fireplace, while a private home office and first-floor guest suite add versatility to the floor plan. Upstairs, four bedrooms each feature private en-suite baths, including a spacious primary retreat with a beautifully appointed bath and oversized custom walk-in closet. The finished lower level expands the living space with a media room ideal for movie nights, an additional bedroom, and full bath. Outdoors, a private fenced backyard and patio create the perfect setting for relaxing and entertaining. Pella windows and thoughtfully selected finishes can be found throughout. Ideally situated in a desirable Winchester neighborhood just down the street from Ambrose Elementary School and moments from downtown Winchester’s restaurants, shops, cafés, and commuter rail service to Boston’s North Station. A sophisticated new construction offering that combines space, style, and an exceptional Winchester location.

2 Atherton Rd, Winchester

Listing courtesy of Listing Agent: Peter Kasseris from Listing Office: Serhant.
$2,700
1 Beds ⋅ 1 Baths ⋅ 73562666 MLS
Best rental on the market in Winchester! This Beautifully updated one bedroom and one bathroom condo is avaiable for rent. The enter island kitchen opens up to a bright living and dining room area. This home boasts of all new kitchen appliances, heat pump (heat and AC), efinished hardwood floors, & recessed dimmable lighting. California closets in both closets in the bedroom, laundry room with washer dryer in unit and entryway to provide ample storage. Walk in laundry room with extra storage is a bonus! Enjoy the convenient location to the commuter rail, library, town restaurants, & shops.

115 Washington Unit 1B, Winchester

Listing courtesy of Listing Agent: Leah Polacke from Listing Office: Gamut Group LLC.
$1,329,000
3 Beds ⋅ 3 Baths ⋅ 73562273 MLS
110 Thornberry Road. Strong west side location near Vinson-Owen Elementary School and the Winchester Swim & Tennis Club. An exceptional opportunity to establish roots in Winchester. 2021 Natural Gas Brute FT Floor Standing Boiler. Replacement windows. Central cooling. 200 amp electric. Updated Kitchen w Double oven. Prefinished hardwood floors. Therma-Tru French doors flow from the dining room to a window-lined bonus room off the dining room provides flexible year-round living space. In-ground swimming pool.

110 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Mark Kiklis from Listing Office: Kiklis Real Estate, LLC.
$2,499,000
4 Beds ⋅ 5 Baths ⋅ 73555666 MLS
Introducing 54 Squire Road,an exceptional newer Colonial privately sited within one of Winchester’s most desirable enclaves.Set on a beautifully landscaped, wooded lot, this sun-filled residence blends timeless architecture with numerous substantial owner upgrades.Highlights include 9’ ceilings, elegant millwork,a designer chef’s kitchen with premium appliances,an impressive family room with custom built-ins and entertaining bar,formal dining with butler’s pantry, private office,and luxurious primary suite with vaulted ceilings, walk-in closets,and spa bath.Expanded outdoor living features a custom outdoor kitchen,fire pit,and multiple patios designed for exceptional entertaining.The finished lower level offers a bonus room, home gym, mudroom, and oversized 2-car garage.Professionally landscaped with exceptional privacy, yet just moments to the Vinson-Owen School,steps to the Swim & Tennis Club,and major commuter routes.A rare opportunity to own one of Winchester’s finest newer homes. See Video: https://player.vimeo.com/progressive_redirect/playback/1217669935/rendition/1080p/file.mp4%20%281080p%29.mp4?loc=external&log_user=0&signature=65fb6c1e2692e9ac8d5b781ceed13c02239d5128d88af87ce725ce6cd7907704

54 Squire Road, Winchester

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

24 Lebanon Unit 1, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$949,999
4 Beds ⋅ 2 Baths ⋅ 73561829 MLS
Discover a rare opportunity to own a versatile ranch in sought-after Winchester, offering flexible living with a two-bedroom main level and a full two-bedroom in-law suite below. The gracious first floor welcomes you with gleaming hardwood floors and a handsome fireplace anchoring the living room. A generously proportioned dining room, complete with a classic built-in china cabinet, opens effortlessly into a bright eat-in kitchen — an inviting space for both everyday living and entertaining. Two well-sized bedrooms with ample closet space and a full bath complete the main level, kept comfortable year-round by central air-conditioning.The lower level offers exceptional flexibility with its own private in-law suite, featuring a warm, fireplaced living room, two bedrooms with plush wall-to-wall carpeting, and a full bath — ideal for extended family, guests, or additional living space.Outside, enjoy a level, easy-to-maintain backyard, convenient off-street parking, and a one-car garage. Ideally located just minutes from Skillings Field and McDonald Field, this home offers wonderful access to local recreation, with Lynch Elementary only 0.8 miles away and the scenic Horn Pond Recreation Area close at hand. Enjoy the convenience of nearby Winchester Hospital, easy access to Route 3, and commuter rail service for a smooth trip into Boston. A home that blends comfort, versatility, and an unbeatable location — a must-see that won't last long. Showings begin 8/22 @ Open House 1:30-3PM

96 Loring Ave, Winchester

Listing courtesy of Listing Agent: Jeremy Smith from Listing Office: StartPoint Realty.
$3,450,000
6 Beds ⋅ 5 Baths ⋅ 73561703 MLS
Situated on a generous18,000SF level lot! Must see this custom built spectacular masterpiece by some of winchester's finest builders, offering unique architectural design and dramatic finishes showcasing a fabulous dining room w/ a custom wine wall cabinet, gorgeous kitchen, with high end 48 inch gas range w/double ovens, 48"paneled fridge, 10' island w/ seating & a walk in pantry! Enter from the oversized three car garage into the stunning mudroom & into the most fabulous home that has hit the market in quite some time. Wide plank oak flooring, high ceilings & tasteful finishes throughout. The family room feature wall has custom arched inset bookshelves & cabinetry with led lighting, gas fireplace & plenty of windows to enjoy views of the gorgeous yard. Enjoy conversations & cocktails in the stylish lounge featuring elegant arched details, a custom wet bar & wine fridge. Oversized sliders to spacious deck draw you to the gorgeous 1/2 acre level lot with **room for pool ** pool shown is virtual image*. The first floor also offers a bedroom or home office option; The second floor features 5 large bedrooms & 3 full baths w/ soaring ceilings in every room; the primary being a dreamy retreat showcasing a spa like porcelain bath w 10' shower & 2 shower heads with soaking tub, bidet toilet & walk in closet! Second floor laundry w/sink & custom cabinetry make doing laundry a joy. The lower level offers plenty of space for media room, game room plus space for a home gym & full bath! This exceptional home is a must see ~the top quality finishes and stunning design will not disappoint!

7 Hutchinson Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,200,000
5 Beds ⋅ 6 Baths ⋅ 73561372 MLS
Introducing 18 Ridge Street — a masterfully restored and reimagined Greek Revival residence where timeless architectural beauty meets elevated modern luxury. Set on a beautifully landscaped 20,654 sq ft lot, this exceptional 5-bedroom, 5 full and 1 half bath home offers over 5,295 square feet of exquisitely curated living space designed for both sophisticated entertaining and everyday comfort. From the moment you arrive, the home’s striking historical columns, wraparound porch, circular driveway, and natural stone detailing create an unforgettable first impression. Inside, every space has been thoughtfully crafted with premium finishes and custom design elements throughout. The showstopping chef’s kitchen features paneled Thermador appliances, a stunning La Cornue induction range, and a custom white oak island that seamlessly anchors the heart of the home. Formal and informal living spaces flow beautifully together, highlighted by exposed chimneys, restored 1800s double doors, multiple fireplaces, floor-to-ceiling windows, and rich hardwood flooring. The luxurious primary suite serves as a private retreat, complete with a tray ceiling, fireplace, spa-inspired bath with radiant heated floors, soaking tub, oversized custom shower, and an impressive walk-in closet with built-in island storage. Additional bedrooms offer ensuite and Jack-and-Jill bath configurations, while the finished third floor provides flexible living with cathedral ceilings, sitting area, and office space.Designed with entertainment and lifestyle in mind, the finished lower level features a custom movie theater, wet bar, wine room, and additional pantry storage. Above the detached two-car garage, finished bonus rooms with a full bath create the ideal space for a home office, gym, studio, or guest accommodations.Blending historic character with cutting-edge efficiency, the home has undergone an extensive structural rebuild and offers fully electric, energy-efficient living with multi-zone heat pumps, EV-ready garage spaces, radiant heated bathroom floors, Pella windows, and premium construction materials throughout. A rare opportunity to own a truly distinctive luxury residence in one of Winchester’s most sought-after neighborhoods.

18 Ridge St, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.
$3,200
3 Beds ⋅ 2 Baths ⋅ 73561319 MLS
Great opportunity to rent this spacious 3-bedroom duplex offering three levels of living space, tucked away on a quiet dead-end street. Freshly painted throughout, the unit features new flooring, an updated kitchen equipped with a stove, dishwasher, and refrigerator, three generously sized bedrooms, and 1.5 bathrooms. The basement offers additional storage space, with a washer and dryer available if needed. The property also includes off-street parking for up to two vehicles.

5 Quigley Court Unit 5, Winchester

Listing courtesy of Listing Agent: Anna Mean from Listing Office: AC Realty.
$3,200
2 Beds ⋅ 2 Baths ⋅ 73560790 MLS
Enjoy easy living at Wedgewood Place, a sought-after condominium community in the heart of Winchester Center. This spacious 2-bedroom, 2-bath home offers a bright, open layout with a wood-burning fireplace and a great balcony. The updated kitchen flows seamlessly into the living and dining areas, creating an inviting space for everyday living and entertaining. The generous primary suite features a walk-in closet, private bath, and separate vanity area, while the second bedroom and updated guest bath provide flexibility for guests or a home office. New hardwood floors & new carpet in bedrooms, in unit laundry, central air, parking, extra storage, and access to the community pool. The professionally managed elevator building. Located near Winchester Center’s restaurants, shops, commuter rail, parks, and everyday conveniences! move right in and enjoy!

666 Main Street Unit 315-3, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,500
3 Beds ⋅ 2 Baths ⋅ 73560549 MLS
Spacious and well-maintained 3-bedroom, 2-bath townhouse featuring three levels of living space, with a large private yard and a storage shed. Enjoy hardwood floors throughout, a fully equipped kitchen with stainless steel appliances, and a finished basement with laundry and abundant storage space. The property includes 4 off-street parking spaces on a paved driveway. Conveniently located with an easy commute to Boston and access to Winchester's highly regarded schools and community amenities.No smoking. First month's rent, last month's rent, and a security deposit are due upon lease signing.

28 East St Unit 28, Winchester

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

7 Ridge Street, Winchester

Listing courtesy of Listing Agent: Shannon Jenkins from Listing Office: RE/MAX Realty Experts.
$4,950
5 Beds ⋅ 2 Baths ⋅ 73560281 MLS
Welcome to this spacious 3-story Colonial, where timeless curb appeal meets modern living. A bluestone path invites you to the main entry, setting the tone for a home designed for both comfort and sophistication. Inside, expansive living and dining rooms showcase wood trim and custom built-ins, while hardwood floors and oversized replacement windows flood the space with natural light. The heart of the home is a fully equipped kitchen featuring granite counters and a premium appliance suite: Sub-Zero refrigerator, Wolf gas range, and Bosch dishwasher. 3/4 bath on the main level. Upstairs, a spacious layout offers 4 bedrooms and 1 bathroom, perfect for families or those seeking generous space. The third floor includes a bedroom & a bonus office ideal for remote work or a quiet retreat. Outside, enjoy a private yard with a shed, plus parking for 4 cars. Located just 8 miles from Boston and moments from the Wedgemere train Station. You’ll be close to outstanding public and private schools, downtown Winchester, Upper Mystic Lake, Winchester Boat Club, Winchester Country Club, Ginn Field Park, and a variety of shopping, dining, and scenic nature trails. Additional features include a washer and dryer with dry storage in the basement. Tenant pays utilities; pets will be considered. Immediate availability.

79 Bacon St Unit 79, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.
$3,700
4 Beds ⋅ 2 Baths ⋅ 73559841 MLS
Spacious 4-bedroom, 2-bath apartment available for immediate occupancy in a two-family home just minutes from Winchester Center. Please note: This is NOT a single-family home. This unique unit occupies the entire first floor and finished lower level. The main level features hardwood floors throughout, a living room, dining room, two spacious bedrooms, a full bath, and an eat-in kitchen with a new refrigerator and dishwasher. The finished lower level offers a large family room, two additional bedrooms, a second full bath, laundry, and ample storage. Private driveway with parking for up to 3 cars, patio, and shared backyard. Conveniently located near Winchester Center, shopping, restaurants, commuter rail, and major routes.

10-12 Webster St Unit 1, Winchester

Listing courtesy of Listing Agent: Ryan Kelly from Listing Office: Real Broker MA, LLC.
$6,000
3 Beds ⋅ 3 Baths ⋅ 73559660 MLS
This beautifully renovated home offers over 2,400 sq ft of thoughtfully designed living space across two levels. The home blends modern finishes with functional comfort, making it ideal for today's lifestyle. Step inside to find a spacious open layout enhanced by high-quality updates throughout. The kitchen, baths, and mudroom feature custom cabinetry with high end Spanish panels, dovetail drawers, and Blum hardware. Additional upgrades include Harvey windows and doors, sleek Kuzco modern lighting, and Italian tile finishes that bring a touch of elegance to every room. With 3 full baths, 3 generous bedrooms, and multiple living areas, there's plenty of room to spread out. The home also offers a two-car garage and ample storage. Set on almost half an acre lot, this home is close to shopping, schools, medical facilities, public transportation and highway access. Convenience and style.

25 Berkshire Dr, Winchester

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

200 Swanton St Unit 705, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.
$5,500
3 Beds ⋅ 3 Baths ⋅ 73557783 MLS
Welcome to this spacious and charming Colonial offering beautiful architectural character, a flexible floor plan, and generous living space across multiple levels.Step into the welcoming foyer and discover a bright, inviting home featuring a fireplaced living room with beamed ceilings and oversized windows, complemented by a sun-filled adjoining sunroom.The beautiful kitchen features granite countertops, ample workspace, and a cozy breakfast nook with convenient access to the side yard. A separate home office and full bathroom on the first floor provide additional flexibility for working from home, guests, or everyday living.Upstairs, the spacious primary bedroom includes a walk-in closet and en-suite bathroom, along with an additional adjoining room that can serve as a nursery, private office, dressing room, or guest space. Two additional generously sized bedrooms, a full family bathroom, and a spacious landing with additional closet storage complete the second floor.The lower level offers an unheated bonus/family room with a decorative fireplace, laundry area, additional storage, and direct access to the two-car garage.Outside, enjoy a beautiful, spacious fenced backyard, perfect for relaxing, entertaining, and outdoor activities.Conveniently located near Middlesex Fells Reservation and all that Winchester has to offer, this home combines space, character, privacy, and convenience in a highly desirable residential setting.

111 Highland Ave, Winchester

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

50 Holland Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$3,600,000
7 Beds ⋅ 8 Baths ⋅ 73556474 MLS
Spectacular ground-up NEW construction estate on expansive, large level lot of 24,688sf, ready for move in, located on a quiet Winchester cul-de-sac. Newly completed, this exceptional residence spans more than 7,000 square feet across impeccably finished levels. Ideally positioned on a quiet cul-de-sac on over half an acre of land in one of Winchester’s most desirable locations, the home offers an extraordinary combination of new construction, refined design, privacy, and convenience, just moments from Winchester Country Club. Designed with entertaining in mind, the residence features seven spacious bedrooms and 7.5 designer baths, providing beautifully appointed private retreats for family and guests. At the heart of the home is an outstanding chef’s dream kitchen, thoughtfully designed with custom cabinetry, expansive preparation and gathering spaces, double oven, top-of-the-line 48" Wolf gas stove, Sub-Zero fridge, 2 Bosch dishwashers. steam oven, built in microwave and wine fridge. The kitchen flows seamlessly into expansive, light-filled lamily, living and dining areas, creating an inviting setting for large gatherings, celebrations, and relaxed everyday living. The flexible floor plan is perfectly suited to today’s lifestyle, with dedicated spaces for a professional home office, private fitness studio, and expansive recreation wing. Set in a lush, private lot with a three-car garage, this large lot property also offers excellent potential for a future pool and outdoor entertaining oasis. A rare opportunity to own a substantial, newly built entertainer’s home in an ideal Winchester setting, close to the town center, dining, schools, recreational amenities, hiking trails, and Wright Locke Farm. Ready to move in and enjoy!

11 Viking Road, Winchester

Listing courtesy of Listing Agent: Post Advisory Group from Listing Office: Engel & Volkers Boston.
$2,100,000
4 Beds ⋅ 4 Baths ⋅ 73556476 MLS ⋅ ['The Ledges'] BLDG.
Experience elevated living in this exquisitely renovated luxury townhouse at The Ledges! This sought-after condominium community, just minutes from Winchester Center, offers the ease of low-maintenance living w/ the feel of a single-family home, plus exceptional amenities including a private clubhouse, swimming pool, & tennis courts. Featuring the community's most desirable floor plan, this home offers an elegant first-floor primary suite w/ dual walk-in closets and a stunning spa-inspired bath. Meticulously reimagined from top to bottom, every element of this extraordinary renovation was thoughtfully curated using the finest imported designer finishes and bespoke craftsmanship, creating an unparalleled level of luxury. The dramatic open-concept main level is highlighted by soaring vaulted ceilings, a fireplaced living room w/ a custom-designed mantel, & walls of glass that open to a private deck overlooking breathtaking western sunsets & tranquil natural surroundings. The designer kitchen is a true showpiece, featuring premium finishes, a sun-filled breakfast area, & seamless flow into the elegant dining room, ideal for both intimate gatherings & entertaining.The second floor offers 3 rooms including a spacious bedroom, beautifully renovated full bath, loft ideal for a home office, & an additional sitting room/TV room or guest space. The walk-out lower level it’s another suite in itself offering a spacious family room, second kitchenette, dining area, game room, additional bedroom with double closets, a luxurious spa bath, oversized laundry room, and abundant storage. Step outside to a private patio surrounded by peaceful, picturesque grounds, creating the perfect retreat for relaxing or entertaining. Ideally located w/ easy access to Winchester Center, Whole Foods, major highways, restaurants, and shops, this exceptional home offers luxury living just 7 miles from downtown Boston.

7 Wainwright Road Unit 113, Winchester

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

1 Town Way, Winchester

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

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