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9 Watson Pl, Winchester
$1,599,000
3 Beds ⋅ 3 Baths ⋅ 73599800 MLS
A complete renovation brings fresh style & modern comfort to this 3 bed, 2.5 bath home, offering an inviting layout designed for the way we live today. The main level features a welcoming living room, spacious family room with fireplace, sun-filled dining room, & beautifully appointed kitchen that connects seamlessly to the surrounding spaces. A dedicated home office offers flexibility for working from home, while a convenient mudroom adds everyday practicality. Upstairs, the primary suite provides a private retreat, complemented by two additional bedrooms, a full bath, & second-floor laundry room. The oversized one-car garage offers additional storage space and potential for modification to accommodate two vehicles. Tucked away on a dead-end street, this home enjoys a convenient location near downtown Winchester's shops & restaurants, commuter rail, Lynch Elementary, Horn Pond, scenic trails, & easy access to Routes 93 & 95. Currently under construction with anticipated completion in Spring 2027. Renderings are for illustrative purposes; final details may vary. Plans available upon request.

9 Watson Pl, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
15 Madison Ave W, Winchester
$1,449,000
4 Beds ⋅ 3 Baths ⋅ 73599772 MLS
Welcome to 15 Madison Avenue West, a classic 1924 Colonial on a 6,338-square-foot lot in Winchester’s Wedgemere neighborhood, just a short stroll from the Wedgemere commuter rail station and the shops and restaurants of Winchester Center. Wood shingle siding and a graceful hip roof offer timeless curb appeal. Inside, eleven rooms, four bedrooms, and 2.5 baths span approximately 2,855 square feet of living space, with hardwood floors and a fireplace for cozy New England evenings. The main level includes a living room, dining room, kitchen, and a den overlooking the picturesque backyard, while all four bedrooms and a full bath are upstairs. The partially finished lower level, included in the total living area, offers 735 square feet of flexible space, a second full bath, and a rare bomb shelter. Steam heat, central air, and a long driveway with ample off-street parking complete the home, all within the Lincoln Elementary School district.

15 Madison Ave W, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
421 Washington Street Unit 421, Winchester
$649,000
3 Beds ⋅ 1 Baths ⋅ 73599605 MLS ⋅ ['419-421 Washington Street'] BLDG.
Turnkey living meets Winchester convenience in this beautifully refreshed three-bedroom, one-bath condominium. Abundant windows fill the rooms with natural light, highlighting refinished hardwood floors and freshly painted interiors. Central heating and air conditioning, separate utilities, and in-unit laundry provide everyday comfort, while a newly paved driveway offers ample parking. Recent building improvements include a brand-new roof and fresh exterior paint, further enhancing the property’s appeal. Ideally situated near vibrant Winchester Center, enjoy convenient access to local dining, boutique shopping, and commuter rail service to Boston. Nearby Winchester Hospital, Middlesex Fells Reservation, I-93, and Route 128/I-95 complement this desirable location. Beautifully presented and move-in ready, this inviting home offers an exceptional opportunity to enjoy all that Winchester has to offer.

421 Washington Street Unit 421, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
419 Washington Street Unit 419, Winchester
$675,000
3 Beds ⋅ 1 Baths ⋅ 73599604 MLS ⋅ ['419-421 Washington Street'] BLDG.
Turnkey living meets Winchester convenience in this beautifully refreshed three-bedroom, one-bath condominium. Abundant windows fill the rooms with natural light, highlighting refinished hardwood floors and freshly painted interiors. A sun-drenched sunroom offers an inviting retreat, while the unit’s own private deck provides a lovely setting for morning coffee or relaxing outdoors. Central heating and air conditioning, separate utilities, and in-unit laundry provide everyday comfort, complemented by a newly paved driveway with ample parking. Recent building improvements include a brand-new roof and fresh exterior paint. Ideally situated near vibrant Winchester Center, enjoy local dining, boutique shopping, and commuter rail service to Boston, with convenient access to Winchester Hospital, Middlesex Fells Reservation, I-93, and Route 128/I-95. Beautifully presented and move-in ready, this inviting home offers an exceptional opportunity to enjoy all that Winchester has to offer.

419 Washington Street Unit 419, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
200 Swanton St Unit 240, Winchester
$1,650
1 Beds ⋅ 1 Baths ⋅ 73597478 MLS
AVAILABLE NOW! Bright and inviting second-floor studio at Parkview Condominiums! Rent includes heat, hot water, electricity, and air conditioning. Additional amenities include storage, an outdoor swimming pool, on-site laundry, and one parking space. An additional parking pass may be purchased. Tenant is responsible for obtaining renters insurance. First month’s rent, last month’s rent, security deposit are required. Virtual Staging used.

200 Swanton St Unit 240, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
171 Swanton St Unit 79, Winchester
$4,200
3 Beds ⋅ 3 Baths ⋅ 73597310 MLS
Charming townhome in The Village at Winchester offers serene living near Horn Pond & the expansive Middlesex Fells Reservation. This well-maintained 3-bedroom residence features an inviting living room with fireplace, flowing into a dining area & patio access. Traditional kitchen opens to the living space, perfect for casual entertaining. Main level includes convenient half bath & storage. Upper level presents a primary bedroom with private bath, two additional bedrooms, & dedicated laundry area. One-car garage + one driveway space, with ample guest parking available. Community amenities feature landscaped grounds, tennis court, pool, & clubhouse. Prime location near Winchester's top-rated schools including the new Lynch Elementary, Winchester Middle & High Schools. Minutes to Winchester Center's amenities including grocery, shops, restaurants, & commuter rail. Flexible lease terms available, 6+ months. Outstanding value in a sought-after complex.

171 Swanton St Unit 79, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.
85 High Street, Winchester
$1,749,000
4 Beds ⋅ 3 Baths ⋅ 73596915 MLS
Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, within a rare 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 Street, Winchester

Listing courtesy of Listing Agent: Catherine Albiani from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
3 Sunset Road, Winchester
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 73596720 MLS
1/2 Acre lot! Welcome to 3 Sunset Road, a beautifully updated 4 BR 2.5 bath colonial with rear addition featuring a 1st floor primary option, a fabulous great room w/vaulted ceilings, and a versatile floor plan! This beautiful home is situated on a generous oversized level lot in one of Winchester’s most loved neighborhoods! The large renovated kitchen with custom cabinetry & high end appliances offers plenty of room for storage, cooking and gathering and opens to a lovely dining room w/ easy access to an expansive deck overlooking the gorgeous back yard, perfect for indoor and outdoor entertaining. A warm and inviting living room features a wood-burning fireplace, while the impressive family room with soaring vaulted ceilings provides an incredible space to gather. The luxurious primary suite offers a spacious bath with double vanities, a walk-in closet, and a private sunroom, ideal for a home office, gym, or quiet retreat. Three additional bedrooms and a full updated bath complete the second level. The finished lower-level playroom offers even more flexible living space. Outside, the expansive, private backyard is truly special, offering endless possibilities for kids play, gardening, entertaining, relaxing. A wonderful opportunity to move right in and enjoy spacious living in a fantastic Winchester location, convenient to schools, shops, restaurants, and all that Winchester has to offer!

3 Sunset Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
238 Washington St Unit 1, Winchester
$2,750
2 Beds ⋅ 1 Baths ⋅ 73595587 MLS
Convenient location! This great apartment features a spacious living room, bright dining room, updated full bath and two cozy bedrooms and in-unit laundry is located in center of Winchester close to commuter rail, shop, school, hiking trails. Sufficient income and credit are required. First month's rent, last month's rent, and security deposit required upon lease signing.

238 Washington St Unit 1, Winchester

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

28 Olive St, Winchester

Listing courtesy of Listing Agent: Ethan Forrest from Listing Office: The Aland Realty Group LLC.
67-69 Hemingway St, Winchester
$1,450,000
8 Beds ⋅ 6 Baths ⋅ 73594547 MLS
Excellent development opportunity in Winchester! This 22,403 sq. ft. lot at 67-69 Hemingway Street is approved for the construction of two townhomes, with architectural plans included in the sale. The proposed design features two spacious residences, each offering 4 bedrooms, 2.5 baths, open-concept living and dining areas, mudroom, walk in pantry, a private primary suite, outdoor living space, an attached garage, and the option to finish the basement for additional living space. Zoned RG, the property will be delivered as a vacant lot, with public water, public sewer, and natural gas available, providing an excellent opportunity for builders and developers to bring this project to life. The location offers an appealing combination of neighborhood living, outdoor recreation, and commuter convenience. Just minutes from the newly constructed Lynch Elementary School, Horn Pond's scenic walking trails, and the Tri-Community Bike Path, the property provides easy access to some of Winchester's favorite outdoor destinations. Downtown Winchester offers a vibrant mix of local shops, restaurants, cafés, and community amenities, along with commuter rail service to Boston. Convenient access to Routes 93 and 95 adds to the property's appeal. Winchester continues to be a highly desirable community with a strong buyer pool seeking quality new construction. With approvals in place, architectural plans included, and a location that appeals to today's homebuyers, this is an attractive opportunity to develop two new residences in one of the area's most sought-after markets.

67-69 Hemingway St, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
5 Forest Cir, Winchester
$2,999,000
5 Beds ⋅ 5 Baths ⋅ 73594545 MLS
New construction currently underway. Estimated completion in approximately Spring/Summer 2027. Set on an impressive 22,629 sq. ft. lot, this beautifully crafted new construction offers exceptional space, thoughtful design, and a peaceful setting with easy access to the Middlesex Fells Reservation and I-93. Designed for today's lifestyle, the main level features a welcoming foyer, elegant living and dining rooms, a spacious family room with fireplace, and a stunning chef's kitchen with a walk-in pantry and adjoining mudroom and half bath. Upstairs, the luxurious primary suite is complemented by four additional bedrooms, 4 beautifully appointed baths, and a convenient second-floor laundry room. An attached two-car garage, generous backyard, and exceptional craftsmanship throughout complete this rare opportunity to own a stunning new home on a charming side street.

5 Forest Cir, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
18 Middlesex St, Winchester
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 73593868 MLS
Inspired by the timeless villas of Europe, this exceptional residence blends classic elegance with modern design. A dramatic curved staircase and soaring architectural details introduce inviting living spaces featuring handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that connect seamlessly to the outdoors. At the heart of the home, a chef’s kitchen showcases custom cabinetry, luxury appliances, and an adjoining mudroom. The outdoor setting offers a private retreat with a granite-columned loggia, heated saltwater pool, landscaped grounds with irrigation, and multiple areas for entertaining.The spa-inspired primary suite, ensuite guest bedrooms, and finished lower level with flexible bonus spaces provide comfort and versatility. Heated driveways and walkways add year-round convenience. Ideally located within walking distance of downtown, the new Lynch School, the new commuter rail station, and an array of shops and restaurants, this home offers a thoughtful balance of timeless style, modern amenities, and everyday comfort.

18 Middlesex St, Winchester

Listing courtesy of Listing Agent: Jennifer Taves from Listing Office: Coldwell Banker Realty - Boston.
15 Foxcroft Rd, Winchester
$3,799,000
8 Beds ⋅ 6 Baths ⋅ 73593484 MLS
Welcome to 15 Foxcroft Road, an 8-bedroom home with 4 full and 2 half baths in Winchester's sought-after Flats neighborhood, offering over 7,000 sq ft on a beautiful corner lot. Two private suites make it ideal for multigenerational living, in-laws, caregivers, au pairs, or long-term guests, with ADU-style flexibility already built in. A full 2012 renovation created a large kitchen with oversized butler's pantry, a spacious family room with built-in cabinetry, a dining room, a playroom, and a mudroom with half bath on the first floor. The second floor has four more bedrooms, including a primary suite with full bath and large walk in closet. The third floor adds an additional bedroom and an office as well as cedar closet. The finished lower level features a full bar, a half bath, and ample space for a game room or media room. This property offers the unique ability to offer two suites perfect for extended family or caretakers. The first-floor suite offers single-level living with two bedrooms, a living room, and a full bath with a zero-entry shower. The second-floor suite has its own private staircase, bedroom, living room, and full bath for real independence from the main household. Outside, enjoy a fully fenced yard, wraparound porch, patio with fire pit, and an attached two-car garage. A unique and special property in one of Winchester's best neighborhoods!

15 Foxcroft Rd, Winchester

Listing courtesy of Listing Agent: Karen S. Garrett from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
38-40 Florence Street Unit 2, Winchester
$3,600
3 Beds ⋅ 2 Baths ⋅ 73593210 MLS
(All are recent repainted, new kitchen floor and countertops) 3-Bed / 2 Full-bath apartment in a desirable Winchester neighborhood for rent. Situated at a quiet street, this three-bedroom and two-bathroom in a two-family house setting has a nice floor plan and decent flow. Hardwood floor throughout. It has a spacious eat-in kitchen with a pantry and with stainless appliances. Two bright generous bedrooms are with high ceiling and fans on the second floor. One big bedroom with a full bath and a fridge is on the third floor. Features also include front enclosed porch, storage shed, and large flat backyard. Full basement provides tons of storage space. Great opportunity to move into Winchester and take advantage of the great schools, cozy community and close proximity to Boston. Two off-street parking are included. Very convenient location and close to Winchester Town Center, schools, shopping and Rt. 93 and 95.

38-40 Florence Street Unit 2, Winchester

Listing courtesy of Listing Agent: WINN Rental Team from Listing Office: WINN Real Estate & Consulting.
419-421 Washington St, Winchester
$1,249,000
6 Beds ⋅ 2 Baths ⋅ 73592723 MLS
An exceptional turnkey opportunity in Winchester, 419–421 Washington Street presents a beautifully refreshed two-family residence featuring significant mechanical upgrades and refined finishes throughout. Major improvements include a brand-new roof, newly paved driveway with parking for 4–5 vehicles, separate central heating and air conditioning systems, separate utilities, fresh interior and exterior paint, and beautifully refinished hardwood floors. Ideally situated near vibrant Winchester Center, enjoy convenient access to local dining, boutique shopping and commuter rail service to Boston. Proximity to Winchester Hospital, I-93, Route 128/I-95, Middlesex Fells Reservation and Winchester's highly regarded schools further enhances the appeal. Move-in ready with extensive recent improvements, this exceptional property offers an ideal opportunity for owner-occupants and investors seeking lasting value in one of Greater Boston's most desirable communities.

419-421 Washington St, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
200 Swanton St Unit 635, Winchester
$2,500
2 Beds ⋅ 1 Baths ⋅ 73592615 MLS
ALL UTILITIES INCLUDED. Spacious 2-bedroom, 1-bath unit featuring a well-designed layout with balcony overlooking the duck pond. Both bedrooms are a good size with closet space. Professionally managed community with on-site laundry, outdoor pool, landscaped grounds, and off-street parking. Conveniently located near downtown Winchester, commuter rail, shopping, dining, and major highways. Tenant responsible for cable and internet. Photos are virtually staged.

200 Swanton St Unit 635, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: REMAX Andrew Realty Services.
18 Surrey Road, Winchester
$2,950,000
6 Beds ⋅ 4 Baths ⋅ 73592433 MLS
Spacious seven-bedroom, four-bath home in one of the area's most sought-after neighborhoods, thoughtfully designed with the flexible living space today's lifestyles demand. Whether accommodating a multigenerational household, extended family, long-term guests, or creating dedicated work and hobby spaces, this home offers exceptional versatility. The main level features an oversized living room with an open-concept layout flowing seamlessly into the dining area and kitchen, creating the perfect gathering space for everyday living and entertaining. French doors open to a large deck, extending the living space outdoors. Two first-floor bedrooms and a full bath provide convenient options for guests, family members, or a home office. Upstairs, you'll find four additional bedrooms, including a spacious primary suite with its own private balcony, a peaceful retreat to begin and end the day. The finished lower level adds even more flexibility with a generous family room, an additional bedroom or office, and direct access to the heated three-car garage. With abundant space to grow, gather, and adapt to changing needs, this exceptional home is ready to welcome its next chapter.

18 Surrey Road, Winchester

Listing courtesy of Listing Agent: Mary Kelly from Listing Office: Century 21 Property Central Inc..
80 Nelson St, Winchester
$815,000
2 Beds ⋅ 1 Baths ⋅ 73591108 MLS
Endless possibilities in this well-loved home less than 1/3rd mile from Winchester High School. Owned by the same family since 1950, this home has been lovingly cared for and is now ready for your updates. The main floor features high ceilings, an eat-in kitchen, and a large rear family sunroom drenched in light. Upstairs you'll find a front-to-back main bedroom, full bath, and nursery, as well as a finished staircase to the third floor, which was used as additional bedroom space. Large level back yard on a quiet street means ample opportunity to entertain or expand.

80 Nelson St, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
258 Cross Street, Winchester
$4,500
4 Beds ⋅ 3 Baths ⋅ 73590971 MLS
--IMMEDIATELY AVAILABLE --- A rare opportunity to rent a detached home in Winchester with the space, privacy and flexibility often missing from condo or townhome living. The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 4 bedrooms, 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Pets negotiable. First month's rent & security deposit due at lease signing. Lease term negotiable.

258 Cross Street, Winchester

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

6 Aricia Ln, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
30 Surrey Rd, Winchester
$1,985,000
4 Beds ⋅ 4 Baths ⋅ 73589478 MLS
Set on over an acre of beautifully landscaped grounds abutting acres of woodland, this extensively renovated Contemporary Cape offers exceptional privacy and a peaceful connection to nature. A thoughtfully designed open floor plan features hardwood floors, a fireplaced living room, elegant dining room, and a beamed-ceiling family room adjoining the remodeled kitchen with stone counters, stainless appliances, and island. A private great room off the foyer, with windows on three walls and a slider to the spacious deck, offers a wonderful retreat. French doors open to the expansive deck overlooking the fenced backyard and wooded surroundings. Upstairs, four bedrooms include a primary suite with custom closets and private bath. The finished walkout lower level offers flexible space for a home office, gym, or guests, with separate entrance and full bath. Stone walls, mature landscaping, a long private driveway, and two-car garage complete this exceptional home.

30 Surrey Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
5 Quigley Court Unit 1, Winchester
$3,200
3 Beds ⋅ 2 Baths ⋅ 73589212 MLS
Great opportunity to rent this spacious 3-bedroom duplex offering three levels of living space, tucked away on a quiet dead-end street. Freshlypainted throughout, the unit features new flooring, an updated kitchen equipped with a stove, dishwasher, and refrigerator, three generouslysized bedrooms, and 1.5 bathrooms. The basement offers additional storage space, with a washer and dryer available if needed. The property alsoincludes off-street parking for up to two vehicles.

5 Quigley Court Unit 1, Winchester

Listing courtesy of Listing Agent: Anna Mean from Listing Office: AC Realty.
5A Euclid Ave Unit 5A, Winchester
$4,500
3 Beds ⋅ 4 Baths ⋅ 73588474 MLS
Completely renovated and beautifully appointed, this exceptional two-level residence offers sophisticated, move-in-ready living in one of Winchester’s most convenient locations. Featuring 3 bedrooms, 3.5 baths, and a private one-car garage, this stylish home combines modern luxury, thoughtful updates, and everyday convenience. The stunning renovated kitchen features high-end stainless steel appliances, contemporary finishes, and a clean, modern aesthetic. The spacious two-level layout provides excellent separation between living and sleeping areas, creating a comfortable and versatile floor plan. Additional amenities include central AC, in-unit laundry, a security system, and the convenience of a private one-car garage. Ideally situated close to vibrant downtown Winchester, enjoy easy access to shops, restaurants, cafés, the commuter rail to Boston, and the beautiful hiking and recreation trails of the Middlesex Fells Reservation. A rare opportunity to enjoy a completely renovated, high-end residence with the space, amenities, and location that make Winchester living so desirable.

5A Euclid Ave Unit 5A, Winchester

Listing courtesy of Listing Agent: Domingo Medina from Listing Office: Coldwell Banker Realty - Lexington.
616 Main Street Unit 3, Winchester
$2,295
2 Beds ⋅ 1 Baths ⋅ 73588377 MLS
GREAT LOCATION!!!Two bedroom one bath brownstone located in Winchester Center. Two good size bedrooms, living room with office area, eat in kitchen with gas stove, dishwasher, and laundry. Pantry in kitchen for additional storage. Deck off of kitchen, one full bath with tub. Street Parking--snow emergencies have to park in town lot with permit $50 a yearWalk out your door to commuter rail, bus, Starbucks, Brueggers, Stop and Shop, and schools.Terms: first, last, 12 month lease

616 Main Street Unit 3, Winchester

Listing courtesy of Listing Agent: Kristine Welch from Listing Office: Greater Metropolitan R. E..
21 Amberwood Dr, Winchester
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73588059 MLS
Welcome to this beautifully appointed and exceptionally spacious home, ideally situated in a quiet, desirable West Side Winchester neighborhood within the sought-after Vinson-Owen School district. Offering an impressive combination of elegant living spaces, flexible accommodations, and thoughtful upgrades, this home provides room for everyone while easily adapting to a variety of lifestyles. At the heart of the home is the expansive granite kitchen, designed for both everyday living and entertaining. Custom cabinetry, Thermador double ovens, a Dacor warming drawer, Sub-Zero refrigerator, wine refrigerator, recessed lighting, and an impressive 50-square-foot center island create a wonderful gathering space with plenty of room for cooking, dining, and entertaining. The kitchen flows into a comfortable family room featuring a custom-built entertainment center and electric fireplace. A gracious formal dining room showcases handcrafted molding and classic wainscoting, while additional first-floor living spaces provide tremendous flexibility for a formal living room, playroom, home office, den, or whatever best suits your needs.One of the home's most appealing features is the first-floor bedroom suite with a full bath, offering exceptional versatility for extended family, guests, an au pair, or anyone seeking the convenience of first-floor living. A dedicated laundry room on this level adds even more functionality. With multiple living areas and flexible rooms throughout the first floor, there are countless ways to create private spaces for additional family members while still enjoying plenty of room to gather together.Upstairs, the generously sized primary suite provides a relaxing retreat with vaulted ceilings, recessed lighting, double closets, and a beautifully tiled private bath with double sinks. Three additional spacious bedrooms, another full bath, and additional office space provide abundant room for family, guests, work-from-home needs, hobbies, or study areas.With its generous proportions, flexible floor plan, multiple bedroom and living configurations, and outstanding West Side location, this is a home designed to grow and change with its owners. Enjoy the peace and privacy of a quiet neighborhood while being part of the wonderful Winchester community. This is more than simply a beautiful house—it is a home offering the space, versatility, and comfort today's buyers are looking for.

21 Amberwood Dr, Winchester

Listing courtesy of Listing Agent: Gayle Winters & Co. Team from Listing Office: Compass.
20 Arthur St Unit 20, Winchester
$329,900
2 Beds ⋅ 1 Baths ⋅ 73587970 MLS
Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

20 Arthur St Unit 20, Winchester

Listing courtesy of Listing Agent: Dan O'Connell Sr from Listing Office: LAER Realty Partners.
22 Salem St. Unit 1, Winchester
$2,600
2 Beds ⋅ 1 Baths ⋅ 73586209 MLS
Welcome to Unit 1, a well maintained residence in a classic 1890 building at 22 Salem St in Winchester. This 2 bedroom, 1 bath condo offers 793 square feet of living space with a layout that works for everyday living and working from home. The kitchen is a true centerpiece, featuring rich cherry wood cabinetry with arched panel doors, dark granite countertops, and a full stainless steel appliance package including a French door refrigerator, dishwasher, gas range, and microwave. Recessed lighting and a window over the sink brighten the space, while the light tile floor adds a clean, easy to maintain finish. The second bedroom offers flexibility as a home office, guest room, or space for a roommate. Enjoy the convenience of laundry in the basement, plus dedicated basement storage for bikes, seasonal items, and extras. Two off street parking spaces add everyday ease. Located in Winchester, this home puts you a 15-minute walk from the Winchester Center commuter rail station on the Lowell Line, with direct service to North Station. Local favorites like Lucia Ristorante, Black Horse Tavern, and Camilla's are close by, with Stop & Shop in town and Whole Foods a short drive away in Woburn.

22 Salem St. Unit 1, Winchester

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

39 Henry Street, Winchester

Listing courtesy of Listing Agent: Kelly Batti from Listing Office: Coldwell Banker Realty - Belmont.
15 Vinson Circle, Winchester
$18,000,000
6 Beds ⋅ 7 Baths ⋅ 73585235 MLS
A NEW BENCHMARK FOR LUXURY LIVING IN WINCHESTER. Introducing a truly one-of-a kind estate—an extraordinary new residence created without compromise on approximately one private acre at the end of a cul-de-sac. Encompassing nearly 10,000 SF, 21 rooms, 6 bedrooms and 7 baths, this remarkable property brings together architectural presence, exceptional craftsmanship, advanced technology and resort-caliber amenities rarely found in a single Greater Boston residence.Beyond its gated entrance and heated driveway, sophisticated interiors unfold through grand entertaining spaces, a statement chef’s kitchen, library/office with wet bar, glass-enclosed fitness studio, acoustically designed cinema, wine lounge and underground wine cellar. The exceptional primary suite features a luxurious dressing room and dramatic two-tier panoramic veranda overlooking the grounds.Outside, the estate transforms into a private resort: spectacular pool with waterfall, integrated spa, flame features and automatic cover; covered outdoor kitchen; sunken conversation lounge with central fire feature; covered dining terrace with fireplace; and beautifully designed grounds offering extraordinary privacy.Behind the elegance is equally impressive infrastructure: 18 heating zones, 9 cooling zones, 600-amp electrical service, approximately 2.5M BTU gas capacity, integrated AV/security, automated gated entry and a 3-car climate-conscious auto lounge with porcelain flooring and dual EV charging.Minutes from Winchester Center and convenient to Boston, this is far more than exceptional new construction. It is a meticulously conceived private estate where architecture, technology, wellness, entertainment and resort living converge—created for the buyer seeking something that simply cannot be replicated.

15 Vinson Circle, Winchester

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

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