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67-69 Hemingway St, Winchester
$1,450,000
8 Beds ⋅ 6 Baths ⋅ 73594547 MLS ⋅ NEW Status
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
5 Forest Cir, Winchester
$2,999,000
5 Beds ⋅ 5 Baths ⋅ 73594545 MLS ⋅ NEW Status
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
16-18 Russell Rd, Winchester
$1,049,000
4 Beds ⋅ 2 Baths ⋅ 73594513 MLS ⋅ NEW Status
Welcome to 16-18 Russell Road, a classic two-family home tucked along a tranquil one-way street just a short walk from downtown Winchester. The bright upper level features 3 bedrooms and 1 bath, while the flexible lower level offers a 1-bedroom, 1-bath layout with the potential to expand to two bedrooms, providing added versatility for investors, multigenerational living, or owner-occupants looking to offset their mortgage with rental income. Hardwood floors run throughout much of the home, while ductless mini-split systems provide efficient heating and cooling, complemented by a gas forced-air system in the basement*. Vinyl siding and an asphalt roof help keep exterior maintenance manageable, while ample off-street parking and a yard add everyday convenience. Located within the district for the newly built Lynch Elementary School, the home is also just a short walk to the commuter rail, a new neighborhood coffee shop, restaurants, and amenities of Winchester's vibrant town center.

16-18 Russell Rd, Winchester
18 Middlesex St, Winchester
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 73593868 MLS ⋅ ACTIVE Status
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
15 Foxcroft Rd, Winchester
$3,799,000
8 Beds ⋅ 6 Baths ⋅ 73593484 MLS ⋅ ACTIVE Status
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
419-421 Washington St, Winchester
$1,299,000
6 Beds ⋅ 2 Baths ⋅ 73592723 MLS ⋅ ACTIVE Status
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
18 Surrey Road, Winchester
$2,950,000
6 Beds ⋅ 4 Baths ⋅ 73592433 MLS ⋅ ACTIVE Status
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
80 Nelson St, Winchester
$890,000
2 Beds ⋅ 1 Baths ⋅ 73591108 MLS ⋅ ACTIVE Status
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
6 Aricia Ln, Winchester
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 73590311 MLS ⋅ ACTIVE Status
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
30 Surrey Rd, Winchester
$1,985,000
4 Beds ⋅ 4 Baths ⋅ 73589478 MLS ⋅ ACTIVE Status
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
21 Amberwood Dr, Winchester
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73588059 MLS ⋅ PRICE CHANGED Status
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
20 Arthur St Unit 20, Winchester
$329,900
2 Beds ⋅ 1 Baths ⋅ 73587970 MLS ⋅ ACTIVE Status
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
39 Henry Street, Winchester
$850,000
3 Beds ⋅ 1 Baths ⋅ 73585414 MLS ⋅ ACTIVE Status
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
15 Vinson Circle, Winchester
$18,000,000
6 Beds ⋅ 7 Baths ⋅ 73585235 MLS ⋅ ACTIVE Status
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
1 Plymouth Rd., Winchester
$3,299,000
7 Beds ⋅ 8 Baths ⋅ 73585058 MLS ⋅ ACTIVE Status
Ideally situated in one of Winchester’s most serene neighborhoods, this exceptional residence offers impressive scale, thoughtful design, and remarkable versatility in a quiet, peaceful setting. It also represents one of Winchester's best values, with tremendous square footage and an au-pair/in-law apartment. Surrounded by beautiful homes and a sense of established elegance, this is a property designed to feel both private and welcoming. Thoughtfully expanded and beautifully built, the home offers 7 bedrooms and 7.5 baths, with generous living spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, a stunning chef’s kitchen opens seamlessly to a dramatic fireplaced living room with soaring cathedral ceilings, creating a warm and inviting gathering space filled with natural light. There is also a family room, also with a fireplace and large picture windows, allowing for an abundance of sunlight. Explore further and you'll find a huge butler's pantry, a must-have feature in today's homes. There is also a wet bar with a beverage fridge. This is a home that has been very thoughtfully designed for how today's buyers actually live, but what truly distinguishes it is the flexibility of design. A private two-bedroom suite offers its own living area, office, wet bar, and full bath, providing an exceptional option for an au pair, extended stays, guests, returning college students or a more private living arrangement. The finished lower level adds even more space for recreation, fitness, entertaining, or simply spreading out. Beautifully proportioned rooms, exceptional functionality, and a serene neighborhood setting come together to create a home that feels substantial yet comfortable, sophisticated yet wonderfully livable. The natural light is exceptional, and outside, an oversized lot offers plenty of play space and a deck to hang out on. Just moments from Mullen Field, close to the town center and trains and an easy trip to Lexington or Cambridge, 1 Plymouth offers a rare opportunity to enjoy exceptional space and privacy in one of Winchester’s most sought-after neighborhoods.

1 Plymouth Rd., Winchester
724 Main St, Winchester
$4,000,000
73582018 MLS ⋅ ACTIVE Status
Exceptional opportunity to own or lease a beautifully renovated, meticulously maintained mixed-use property with exciting development potential just outside Winchester Center! Offering approximately 7,010 sq. ft. across four levels, this versatile building offers expansion potential & features a flexible layout with numerous private offices, conference and meeting spaces, open work areas & multiple restrooms ideal for a variety of professional, office or mixed-use possibilities. Additional highlights include 19 parking spaces, a direct-access garage and beautiful Wedge pond views. The generous floor plan can accommodate a single occupant, multiple businesses or teams, while the property’s mixed-use zoning offers potential for residential redevelopment. Conveniently located close to Winchester Center with access to the bus line right outside the door & easy access to the commuter rail, schools, restaurants, coffee shops, shopping, banks and downtown amenities. A rare opportunity to purchase, lease or explore the property’s development potential in a highly desirable Winchester location! Call for additional info/ brochure!

724 Main St, Winchester
63 Shore Rd Unit 12, Winchester
$345,000
1 Baths ⋅ 73582003 MLS ⋅ ACTIVE Status
Excellent opportunity to own your own office condo at Judkin Green in downtown Winchester. This garden office condo consists of 625 square feet of open space with 1 private bathroom and storage room. Turn this office into your own! Other businesses include accountants, insurance, mortgage lenders, dentists/medical, and more. Excellent location- close to other businesses, restaurants, shops, parking, and commuter rail. Last two photos are AI generated.

63 Shore Rd Unit 12, Winchester
1 Overlook Way, Winchester
$1,750,000
4 Beds ⋅ 3 Baths ⋅ 73581571 MLS ⋅ ACTIVE Status
Welcome to One Overlook Way in Winchester. This spacious 4+ bedroom center-entrance Colonial is tucked away on a short cul-de-sac off High Street, in a premier location close to Ambrose Elementary School and the Winchester Country Club. The foyer opens to a thoughtfully designed floor plan with wonderful flow for everyday living and entertaining. The generously sized eat-in kitchen features stone countertops and stainless steel appliances and connects to the beautiful dining room. The kitchen also opens naturally into the cozy family room - with gas fireplace, custom built-ins and access to the back and side yard, the family room will be well utilized! A larger front-to-back living room with fireplace and box windows is located off the foyer and is complemented by an adjoining oversized library or playroom. Upstairs, the spacious primary suite offers a private bath with double vanity, full shower and great closet space. Three additional bedrooms feature hardwood floors, generous closets and access to a shared full bath. The third-floor bonus space provides flexible room for guests, a home office or storage. The finished lower level adds even more usable space, with a fireplace and room for exercise, hobbies or relaxation. Enjoy the outdoors in this large, level yard with established plantings, brick patio and plenty of space to entertain. There is a two-car garage plus 300+sf of unfinished space above the garage. Please ask the agent for more information. This home truly has it all. This is one home you do not want to miss.

1 Overlook Way, Winchester
666 Main Street Unit 217, Winchester
$700,000
2 Beds ⋅ 2 Baths ⋅ 73581469 MLS ⋅ ACTIVE Status
Easy one-floor living in Winchester Center with garage parking for one car! Fabulous location near town center, TRAIN, shopping, restaurants, schools and library. Enjoy the open layout with extra wall of beautiful kitchen cabinets, large peninsula/eating bar, fireplace, balcony and a nook for a desk or whatever you wish. Large primary bedroom has two windows, large walk-in closet and full bath. Second bedroom is across hall from laundry and bath with shower. Air handler and condenser replaced in 2022. Central air throughout. Hot water heater and water shutoff installed - 2018. The additional storage unit is off the main lobby for easy access. Amenities include 2 elevators, inviting POOL and onsite rubbish pickup. Perfect home for first time buyers, downsizers, anyone commuting to Boston or in search of a vibrant town center lifestyle. New budget meets conventional financing guidelines!

666 Main Street Unit 217, Winchester
9 Priscilla Ln, Winchester
$1,325,000
4 Beds ⋅ 2 Baths ⋅ 73579538 MLS ⋅ ACTIVE Status
1st OPEN HOUSE! SUNDAY, OCTOBER 4th, 11:30am-1:00pm! Timeless New England charm meets prime Winchester living at 9 Priscilla Lane. Tucked along a quiet, tree-lined neighborhood on Winchester’s East side, this inviting 4-bedroom home offers the perfect balance of suburban tranquility, outdoor adventure, and seamless connectivity.Inside, the sun-drenched home features rich hardwood floors, a gorgeous kitchen, wood burning fireplace, flexible living areas, and an intuitive layout designed for both daily relaxation and effortless entertaining. Step outside to an expansive, private backyard—a sunlit haven perfect for weekend barbecues, garden projects, or crisp New England evenings.Outdoor enthusiasts will love living moments away from the endless hiking, trail running, and scenic escapes of the Middlesex Fells Reservation. For commuters, rapid access to I-93 and Route 128/I-95, combined with nearby Commuter Rail stations, makes reaching Boston, Cambridge, or local tech hubs exceptionally fast and direct. Complete with proximity to top-rated Winchester public schools and vibrant downtown dining and shops, this property delivers the quintessential North Shore lifestyle in an unmatched location. MAKE 9 PRISCILLA LANE YOUR HOME TODAY!

9 Priscilla Ln, Winchester
200 Swanton St Unit 727, Winchester
$399,000
1 Beds ⋅ 1 Baths ⋅ 73579389 MLS ⋅ ACTIVE Status
Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and electricity, as well as access to the in-ground swimming pool. A private basement storage unit is also included for added convenience. With its comfortable layout, private balcony, pond and garden views, included utilities, and convenient location, this move-in-ready condo is a great opportunity you won’t want to miss!

200 Swanton St Unit 727, Winchester
7 Lakeview Terrace, Winchester
$2,400,000
6 Beds ⋅ 4 Baths ⋅ 73578443 MLS ⋅ ACTIVE Status
RARE WATERFRONT OPPORTUNITY on Upper Mystic Lake with spectacular sunset views! Tucked away on Lakeview Terrace, this special 1910 home offers a combination rarely found in Winchester: waterfront living, privacy, beautiful southwest light and exceptional convenience. Gracious rooms, period details and quality craftsmanship give the home wonderful character, while its generous layout offers an exciting opportunity to update and create something truly special. The home features 5-6 bedrooms, a home office and expansive living spaces designed to take advantage of the lake views. The kitchen, renovated some years ago, was thoughtfully positioned so the view can be enjoyed while preparing meals. An unfinished lower level with high ceilings offers additional possibilities. Just steps from Wedgemere Commuter Rail Station, 1/2 mile to Shannon Beach and less than a mile to Winchester Center via the Tri-Community Bikeway. A remarkable setting, beautiful sunsets and an opportunity that may not come again for years. Don't delay your visit!

7 Lakeview Terrace, Winchester
200 Swanton St Unit 303, Winchester
$495,000
2 Beds ⋅ 1 Baths ⋅ 73578112 MLS ⋅ ACTIVE Status
Enjoy the best of Winchester living in this beautifully updated two-bedroom condo at Parkview, just minutes from Winchester Center, local shops, dining, parks, and commuter access. A bright, open-concept layout creates an inviting flow for everyday living and entertaining. The modern kitchen features stainless steel appliances, while fresh paint throughout adds a crisp, contemporary feel. Both generously sized bedrooms offer excellent closet space and flexible living options. The living area overlooks a scenic duck pond and professionally maintained grounds, creating a peaceful setting year-round. The secure card-entry building offers ample resident parking, guest parking off Swanton Street, and access to an in-ground pool. HOA includes heat, hot water, electricity, and AC for exceptional convenience and value. One basement storage unit is included.

200 Swanton St Unit 303, Winchester
30 Willowdale Rd, Winchester
$3,200,000
8 Beds ⋅ 7 Baths ⋅ 73577116 MLS ⋅ ACTIVE Status
A rare expression of quality, craftsmanship, and enduring style, 30 Willowdale Road presents an exceptional opportunity to own a newly constructed residence in one of Winchester’s most coveted neighborhoods. Set on a beautifully proportioned, large and level lot, this remarkable home has been thoughtfully conceived to offer the space, sophistication, and effortless lifestyle expected of a truly exceptional property.From the moment you enter, the quality is unmistakable. Gracious proportions, refined architectural details, exceptional craftsmanship, and carefully curated finishes create a home designed not simply for today, but with a sense of lasting beauty that will transcend trends for years to come. Every space feels considered, polished, and substantial, with an elevated yet welcoming character throughout.At the heart of the home, a spectacular chef’s kitchen pairs custom finishes with premium Viking appliances, creating a beautiful gathering place for everyday living and entertaining. Expansive living spaces flow naturally from one to the next, equally suited to intimate evenings, holiday celebrations, and a house full of family and friends. 8 bedrooms and 6.5 baths provide extraordinary flexibility, privacy, and comfort, with abundant space for guests, home offices, fitness, recreation, and the evolving needs of modern life. Outside, the expansive level grounds are a luxury unto themselves, offering wonderful possibilities for outdoor entertaining, recreation, gardens, and the simple pleasure of having room to breathe. A two-car garage and the ease and efficiency of brand-new construction further enhance the lifestyle.Sophisticated without being showy and luxurious without sacrificing warmth, 30 Willowdale Road is the kind of home that feels exceptional today and will remain so for generations. A rare combination of location, land, craftsmanship, and enduring quality in a premier Winchester neighborhood.

30 Willowdale Rd, Winchester
258 Cross St, Winchester
$974,900
3 Beds ⋅ 3 Baths ⋅ 73575764 MLS ⋅ ACTIVE Status
Are rates making you feel like home buying is out of reach? The sellers are now offering A TWENTY THOUSAND DOLLAR ($20,000) CREDIT, PERFECT to put towards closing costs or a 2/1 rate buy down. Enjoy over a ONE THOUSAND ($1000) DOLLAR PER MONTH savings year one and over a FIVE HUNDRED ($500) DOLLAR PER MONTH savings year two. A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! 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 3 bedrooms, a versatile bonus room (4 beds on public record), 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. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

258 Cross St, Winchester
189 Washington St Unit 2, Winchester
$765,000
3 Beds ⋅ 2 Baths ⋅ 73575116 MLS ⋅ ACTIVE Status
SELLERS WILL PRE-PAY 1 YEAR OF CONDO FEE! Carefree professionally managed condo convenience in Winchester Center! Soaring ceilings and generous living spaces make this home feel exceptionally spacious and inviting. Plenty of space to gather in the bright living room with oversized windows, family room with beautiful french doors, and large dining room with new built-in bar area. A versatile bonus room is perfect for a home office, gym, or additional living space. The kitchen opens directly to the generous dining room and features granite countertops, stainless steel appliances, and access to the deck. A full bathroom completes the first level. Upstairs, you’ll find three bedrooms, another full bathroom, and convenient laundry. This spacious home also offers a shared fenced-in yard, off-street parking for two cars, and additional storage in the basement. Abundant public transportation plus the charming shops and restaurants of Winchester Center, as well as elementary, middle, and high schools all at your fingertips. Welcome home to Winchester!

189 Washington St Unit 2, Winchester
4 Dartmouth, Winchester
$4,299,000
5 Beds ⋅ 6 Baths ⋅ 73574948 MLS ⋅ ACTIVE Status
Gracefully positioned along Winter Pond, this exceptional waterfront residence offers a rare opportunity to own one of the Flats most desirable addresses. A true legacy property, it has been beautifully renovated, maintained and updated, blending classic architecture with modern comfort. This 5-bedroom, 5.5 bath classic provides generous, well-proportioned rooms designed for both refined entertaining and relaxed daily living. Water views serve as a serene backdrop to the large modern kitchen, where the natural light dapples and shines all day. It's what everyone craves: the bright, sunny, warm inviting hub of the home. There is an attached mudroom with custom lockers/cabinets, and radiant heat floors. A large family room is attached and is highlighted by a gas-burning fireplace. The expansive living and dining rooms offer plenty of space for more formal entertaining and big groups. One of our favorite features is the study, tucked off the living room and connected to a divine screened-in porch. The natural woodwork and handsome architecture harken to yesteryear while providing the perfect home office and a place to unwind when done working. A generous primary suite is a private retreat with a spacious bath and ample walk-in closets. There are 4 other ample bedrooms, 3 of which are connected to baths, and a second-floor laundry complete this floor. The basement has a huge media and game room, sauna, gym, wine cellar and direct access through a mudroom to a covered patio. Several curated outdoor dining and gathering areas invite entertaining, sunset dinners or quiet reading, overlooking the pond. There is also a full walk-up attic with great ceiling height, unfinished and waiting for your inspiration. An oversized two-car garage with soaring ceilings complete the must-haves. Kayak, skate, go fishing and enjoy life on the water in one of Winchester's most prized, quiet neighborhoods!

4 Dartmouth, Winchester
465 Washington Street, Winchester
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73574928 MLS ⋅ ACTIVE Status
Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street, Winchester
465 Washington Street Unit 465, Winchester
$1,250,000
4 Beds ⋅ 3 Baths ⋅ 73574929 MLS ⋅ ACTIVE Status
Refined, low-maintenance living with the scale, finishes, and lifestyle advantages rarely found at this price point. This 4-bedroom, 3-bath townhouse (built in 2017) features open-concept design and high-end finishes. The main living area is anchored by a designer chef’s kitchen with premium appliances and a large island that flows to a large living room with a gas fireplace. The primary suite is a true oasis with a walk-in closet, spa bath, and a private balcony for evening relaxation. 3 other bedrooms, a refined bath plus second floor laundry provide flexibility for family, guests, or home office needs. The lower level is versatile, perfect for a media room and home gym. Convenience & Amenities: Enjoy a private, fenced backyard, dining patio, EV charger, and premium parking. Quick access to the Fells, major routes, plus close to top schools, parks, and the town center for an easy downtown commute. A rare turn-key value, bigger and better than most single families at this price.

465 Washington Street Unit 465, Winchester
37 Mayflower Road, Winchester
$3,149,000
7 Beds ⋅ 8 Baths ⋅ 73573670 MLS ⋅ ACTIVE Status
Magnificent newer sun-filled Colonial ideally situated in a premier West Side cul-de-sac, offering over 8,000 sq ft of beautifully finished living space across four levels-A great price at only $368psf! !Designed for grand-scale entertaining and multi-generational living, this exceptional home features 7 bedrooms, 7.5 baths, four fireplaces and a 3-car direct-entry garage, all complemented by custom built-ins, fine cabinetry and beautiful millwork throughout. The newly renovated chef’s kitchen showcases quartz countertops, an oversized center island, two dishwashers and a butler’s pantry with wine fridge and ice maker, flowing seamlessly into the elegant dining room, living room and fireplaced family room overlooking the meticulously maintained grounds. A dedicated first-floor wing offers incredible flexibility for extended family, au pair or guests, while a private office with custom wet bar and additional spaces can easily accommodate two executive home offices. Upstairs, the grand primary suite is joined by four additional bedroom suites, each offering a private bath, sitting area and generous closet space. The third floor provides a completely private guest or teen suite with a full bath and two closets.The finished lower-level offers media, game and gym areas with a full bath and direct access to the inviting heated pool and lush landscaped grounds. Unmatched in scale and versatility with resort-like amenities, exceptional craftsmanship and a coveted West Side location, this remarkable home offers luxury living at its finest.

37 Mayflower Road, Winchester

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