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$1,549,000
3 Beds ⋅ 3 Baths ⋅ 73449320 MLS
Must see! Nestled along Winchesters beloved Winter Pond, this beautiful home offers a rare opportunity to live the waterfront dream just 7 miles from Boston! Featuring an oversized lot with breathtaking panoramic water views & offering a lifestyle that could include kayaking, paddle boarding, ice skating, fishing etc..along with serenity and privacy so hard to find. This home offers ample living space that flows nicely between the formal living room, dining room, kitchen, office and family room, all of which have picturesque views. Many recent updates including kitchen, baths, roof, heating & de-leading; making this lovely home move in ready! 3 to 4 bedrooms, 2 1/2 baths w/ a finished walk out basement w/ mud room, laundry, rec. room, storage and gym area. The setting is simply gorgeous with expansive rolling green lawn offering plenty of room for future expansion.Enjoy your morning coffee from deck appreciating all that nature offers, plus spectacular sunsets in the western skies!

32 Woodside Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,150,000
4 Beds ⋅ 2 Baths ⋅ 73442848 MLS
This beautiful Victorian home, featuring an inviting front porch, stunning period detail including wainscoting, original tin ceilings, custom built-ins, and three fireplaces is not to be missed! Maple hardwood floors flow through an open-concept layout to a spacious eat-in kitchen with a lovely exposed brick wall. The second floor has three bedrooms and a full bath plus a sweet window seat and an additional built-in. The third floor offers a fourth bedroom and a versatile bonus—ideal for a family room, office or studio. Freshly painted throughout and updated baths, newer windows, and electrical system enhance modern comfort and complement the original charm. Outside, enjoy a large brick patio and a detached garage with upstairs storage. This is a highly desirable neighborhood, conveniently located near excellent schools, the quaint town center, and commuter rail to Boston. Scenic Middlesex Fells has acres of forested trails to explore. Also nearby aer Leonard Park and the TC bike path.

50 Lincoln Street, Winchester

Listing courtesy of Listing Agent: Lynne Russo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73442291 MLS
NEW PRICE & UPDATES BEAUTIFULLY REIMAGINED!Welcome home to this stunning brick ranch tucked on a quiet cul-de-sac in Winchester’s coveted West Side. Every space has been thoughtfully designed, blending classic craftsmanship with distinct elegance. The bright open layout invites you in with a chef’s granite and stainless kitchen, sun-filled family room framed by floor-to-ceiling windows, and French doors opening to a new composite deck and tranquil backyard. Gather in the elegant dining room and sunken living room with fireplace, or retreat to the serene primary suite with sitting area and spa-inspired bath. A flexible fifth bedroom or office with private entrance is perfect for guests or in-laws. The finished lower level offers a game room, gym, wine storage, cedar closet, and more. Spectacular & unbeatable location and neighborhood awaits you! Move-in ready, moments to Winchester Center, top schools, and commuter access—where timeless style meets effortless living.

5 Azalea Road, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.
$2,250,000
6 Beds ⋅ 5 Baths ⋅ 73438521 MLS
Welcome to 14 Grant Road – a stunning new construction home offering spacious, open-concept living in one of Winchester’s most desirable neighborhoods. Designed for modern lifestyles, this home features a chef’s kitchen that flows seamlessly into the dining and living areas, creating the perfect space for entertaining and everyday living. A sun-drenched 3-season porch expands your living space and offers a peaceful retreat. Enjoy the flexibility of dual primary suites on both the first & second floors, providing exceptional layout options for multi-generational living or guest accommodations. The mudroom w/ dual closets adds everyday functionality and style, while the finished lower level includes a full bathroom and versatile flex space—ideal for a home office, gym, or playroom. Located in the sought-after Muraco School District w/ easy access to I-93, this home combines luxury, convenience, and thoughtful design. Don’t miss your chance to own this exceptional new build in Winchester!

14 Grant Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
$1,200,000
2 Beds ⋅ 2 Baths ⋅ 73452498 MLS ⋅ ['Allegro'] BLDG.
Welcome to unit # 2 at Allegro, an ELEVATOR building, built in 2021. Containing 11 units. This building is comfortable, quiet, and modern. Just set back far enough to be out of the traffic. Easy one-level living with an open concept, living room, dining room, and kitchen that all flow seamlessly together. The primary bedroom has its own ¾ bathroom with a full bathroom for the rest of the household/visitors. This unit is unique in that it comes with TWO PARKING SPACES in the heated garage and your own storage area. PLUS, this unit is one of only two units with the largest OUTDOOR brick PATIO with sliding glass door access from the living room. Comforting to be able to open your slider and be outside in a spacious, quiet area of your own. In unit laundry. Step out to the street and enjoy being minutes away from all that Winchester Center has to offer: restaurants, shops,a supermarket, even a hardware store,and the commuter rail to North Station. You will truly enjoy living at the Allegro

36 Elmwood Ave Unit 2, Winchester

Listing courtesy of Listing Agent: from Listing Office: Coldwell Banker Realty - Lexington.
$1,825,000
6 Beds ⋅ 4 Baths ⋅ 73418086 MLS
A truly special opportunity to own a home in one of Winchester’s most desirable neighborhoods, just outside the vibrant town center! Welcome to 19 Glengarry Road~ this character-filled residence offers the perfect blend of charm, warmth & potential, making it ideal for buyers looking to personalize & create their dream home. Nestled in a top neighborhood near wedge pond, the home boasts classic details throughout, from original woodwork, beautiful fireplaces & hardwood floors to cozy, sun filled living spaces incl. a dreamy sun porch overlooking gorgeous back yard. 4 bedrooms & 2 baths on the 2nd floor, while the 3rd floor offers 2 additional beds. Full basement with flex living spaces including an additional bed or office & full bath. A large yard awaits with access/ frontage all the way to Grassmere Ave. With easy access to schools, shops, restaurants & the commuter rail, you’ll enjoy the best of Winchester living with unmatched convenience & one of the best neighborhoods around!

19 Glengarry Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,630,000
7 Beds ⋅ 6 Baths ⋅ 73383662 MLS
This stunning Colonial Revival home, is just moments from the train station, town center, and Ambrose School. The kitchen features radiant floor heating. The first floor includes a chef-designed kitchen, expansive living and family rooms, a formal dining room, a half bath, and a mudroom. On the second floor, you'll find a luxurious master suite with walk-in closets and a Jacuzzi bath, along with two additional bedrooms and an updated bathroom. The third floor offers a variety of flexible living spaces: one separate bedroom with an en suite, one study that can share the en suite as a separate bedroom, and one suite/bedroom with a bath, morning kitchen area, and living room. The finished basement is equipped with a wet bar and wine cellar. Outside, a new two-car garage, storage shed, and patio/deck enhance the generous lot. Recent upgrades include kitchen, porch, HVAC, electrical systems, IT wiring, and beautiful wood flooring.

10 Sheffield Road, Winchester

Listing courtesy of Listing Agent: Andersen Group Realty from Listing Office: Keller Williams Realty Boston Northwest.
$1,290,000
3 Beds ⋅ 2 Baths ⋅ 73437800 MLS
Nestled in Winchester’s coveted Lincoln School district, this classic Colonial offers timeless charm, modern comfort, and unbeatable curb appeal! Situated on a beautiful corner lot, the property features a detached 2-car garage and welcoming exterior that sets the tone for what awaits inside. The main level boasts a warm and inviting living room with a wood-burning fireplace, perfect for cozy evenings. A flexible office or playroom offers additional space for today’s lifestyle needs, while the formal dining room provides a wonderful setting for gatherings and special occasions. The kitchen boasts easy access to the patio and yard, ideal for outdoor entertaining and everyday enjoyment. Upstairs, you’ll find 3 bedrooms, including a spacious primary suite with dual closets and a private walk-out area — which could be the perfect retreat for your morning coffee. Available for the first time in over 40 years, this cherished home is ready to be passed down from one loving owner to the next.

40 Sargent Road, Winchester

Listing courtesy of Listing Agent: Vita Realty Group from Listing Office: Compass.
$950,000
3 Beds ⋅ 2 Baths ⋅ 73426760 MLS
Breathtaking luxury condo just moments from Winchester Center and the commuter rail. This recently updated home offers bright, spacious, one-level living with hardwood floors and custom shutters throughout. The kitchen features quartz countertops, stainless steel appliances–including GE Café range and microwave, an oversized sink, and large peninsula with ample seating flows seamlessly to the adjoining living room with gas fireplace. The nearby pantry offers plenty of storage with stacked laundry adding exceptional convenience. A versatile dining room with large windows provides additional space for flexible use. The primary suite, which includes a walk-in closet and private bath with double vanity and walk-in shower, is complemented by two additional bedrooms and a marble-tiled guest bath. Thoughtful storage throughout includes multiple closets and a dedicated basement. Enjoy a fenced yard with patio for entertaining and off-street parking for four vehicles. Welcome home!

16 Park Ave Unit 1, Winchester

Listing courtesy of Listing Agent: Andrea Mackey from Listing Office: Barrett Sotheby's International Realty.
$1,425,000
4 Beds ⋅ 2 Baths ⋅ 73447622 MLS
Attention renovators and investors! This Cape-style home in need of significant renovation offers 7 rooms, 4 bedrooms, and 2 full baths. Features include a fireplace living room, dining room, and hardwood flooring throughout. Enjoy a private yard for outdoor enjoyment. Prime location directly across from the Middlesex Fells Reservation and minutes to Winchester Center, schools, shops, and restaurants. Great potential to restore or redevelop in one of Winchester’s most desirable areas. All offers due Tuesday the 28th at 12 PM.

102 Hillcrest Pkwy, Winchester

Listing courtesy of Listing Agent: Curtis Howe from Listing Office: Howe Realty Group.
$1,015,000
4 Beds ⋅ 2 Baths ⋅ 73444775 MLS
Tucked away on a private cul-de-sac in one of Winchester’s most desirable neighborhoods, this adorable 4-bedroom, 1.5-bath single-family cape style home with full rear dormer offers a rare opportunity to renovate, expand, and build equity in a prime location. Set in the brand new **Lynch School District**, this property is ideal for homeowners, investors, or builders looking to customize and add value. The home features a traditional floor plan with sun-filled rooms, hardwood floors with great outdoor space on a generously sized lot. It is the perfect canvas to customize and add your personal touch! Large bedrooms, bright sunny rooms, large newer windows, gleaming hardwood floors and so much curb appeal. Located just minutes from Winchester Center, the commuter rail, schools, and major routes. Don’t miss your chance to own in a top-tier neighborhood with strong potential to build equity. Bring your vision and make 9 Sylvester Court your own!

9 Sylvester Court, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$2,030,000
6 Beds ⋅ 6 Baths ⋅ 73442841 MLS
Welcome to 58 Bacon Street—a perfect blend of classic charm and modern comforts. The main level features a front-to-back fireplaced living room, sunroom, formal dining room, and a stunning 2024 kitchen renovation with custom cabinetry, quartz island, and high-end stainless appliances, opening to a bright family room. Upstairs offers flexible space with dual primary suite options (one with elevator access & attached sitting room), plus an additional bedroom and office. The third floor includes two bedrooms, a bath, and a bonus room; the finished basement adds a playroom, full bath, ample storage and a mud area. Enjoy two outdoor living areas and a fully fenced yard. Elevator access from the attached, heated garage, plus a detached two car garage. Ideally located near Wedgemere Station with quick access to Boston, Winchester Center, Mystic Lakes, and the Fells, this expansive home is perfect for multigenerational living or those seeking accessibility and space.

58 Bacon St, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,038,500
3 Beds ⋅ 2 Baths ⋅ 73438045 MLS
Discover this charming raised ranch set on an oversized lot in one of Winchester’s most desirable neighborhoods. Enjoy the convenience of an attached garage and a wide driveway with ample parking for multiple vehicles. Step outside to a spacious, fenced-in yard and deck—perfect for gatherings, play, or simply relaxing. Inside, the sun-filled living room features gleaming hardwood floors and a cozy fireplace, opening seamlessly to the dining room and kitchen. Three comfortable bedrooms and a full bath complete the main level. The lower level offers a welcoming family room with a second fireplace and a dedicated storage room for added functionality. Ideally located just minutes from downtown Winchester, the brand-new commuter rail station, and with easy access to Boston, this home blends comfort, convenience, and charm. Loved by one family for many years—now it’s ready to become yours!

41 Englewood Rd, Winchester

Listing courtesy of Listing Agent: Lesley Smith from Listing Office: Barrett Sotheby's International Realty.
$1,627,000
4 Beds ⋅ 3 Baths ⋅ 73435608 MLS
This stunning 4-bedroom Center Entrance Colonial in the desirable Ambrose School District has been beautifully updated for modern living. A complete first-floor renovation features a reimagined layout with a custom-designed kitchen boasting Thermador and Bosch appliances, marble and quartzite counters, walk-in pantry, and a bar w/ beverage fridge. Spacious, light-filled rooms showcase gleaming hardwood floors, three fireplaces, and two staircases, blending timeless character with today’s style. The inviting living room w/ stone fireplace opens through French doors to a Trex deck & expansive backyard, perfect for entertaining. The primary suite offers vaulted ceilings, walk-in closet, & spa-like bath w/ soaking tub & walk-in shower. Additional highlights include central air, mudroom off 2-car garage, updated baths, & enhanced insulation throughout. Conveniently located near Winchester Center & the train station, this move-in ready home offers comfort, elegance, and everyday convenience!

73 Grove St, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
$2,900,000
6 Beds ⋅ 7 Baths ⋅ 73404870 MLS
*Incredible value!* Nestled in the heart of Myopia Hill, this custom-built home is sure to impress! Live your best life at 26 Swan Road offering 6 bedrooms, 6.5 bathrooms with 2 primary & suite options! This magnificent residence boasts expansive living spaces, elevator, indoor pool & 3 car garage! Exquisite craftsmanship is shown throughout this home including a newly renovated gourmet kitchen w/custom cherry cabinetry & high end appliances leading to adj. family room w/ fireplace. A handsome library w/ fireplace offers a warm and inviting space to relax. The highlight of this extraordinary home is the 16x32 indoor gunite pool & jacuzzi set within a breathtaking atrium room w/soaring vaulted ceilings, perfect for year round exercise and entertainment. Each of the spacious bedrooms provides a retreat-like atmosphere, complete w/ensuite baths for ultimate comfort & privacy. The home also features 4 fireplaces, 2 home offices, a newly finished basement w/ rec room, fplc, BR & full bath!

26 Swan Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$899,000
4 Beds ⋅ 3 Baths ⋅ 73404303 MLS
Exceptional investment opportunity. Located in the heart of desirable Winchester, this multi family property offers a rare opportunity to own a ready to renovate, vacant building with incredible potential. Two 1 bedroom, 1 bathroom units and 1 two bedroom unit. This property is primed for a full renovation. Perfect for investors, end users or travellers looking for their own pied-a'-terre, while collecting rents. Property also has a detached 2 car garage with 2nd level. Plenty of off street parking with 3 separate driveways. Bring your vision and unlock the full value of this well located multi-family just minutes from its gorgeous downtown, the commuter rail, schools and local area amenities. Opportunities like this rarely come in Winchester. Here's your chance to keep this in your family for generations to come.Sold as is Buyer and Buyers agent to perform due diligence.

60 Harvard, Winchester

Listing courtesy of Listing Agent: Mark Krasnyansky from Listing Office: eXp Realty.
$8,000
4 Beds ⋅ 3 Baths ⋅ 73421342 MLS
An elegant property on one of Winchester's most beautiful residential side streets, facing the Middlesex Fells, with breathtaking seasonal views of the reservoir. Feels like a wooded retreat! Features 4 BR, 3 full BA; granite & stainless kitchen; a huge open-concept living area with 10ft+ ceilings, grand fireplace & wet bar; secluded screened patio, deck. Hardwood floors, designer light fixtures. Lovely, muted, neutral paint colors. 2 car garage. Newer furnace. AC. Outdoor fire pit. Screened patio. Home office area. Only 7 mi north of Boston & a short drive to lively, charming, downtown Winchester -- with shops, dining & a 20-min train to North Station. Muraco Elementary school. This property is unique and special -- was once used as an art gallery. If you're going to rent, why not choose a home that's really cool?! Available 1/1/26 or later. First, security due at lease signing. Delead certification.

10 Hillcrest Parkway, Winchester

Listing courtesy of Listing Agent: Robyn Bonnett from Listing Office: Coldwell Banker Realty - Lexington.
$999,999
3 Beds ⋅ 2 Baths ⋅ 73443017 MLS
Experience luxury living just steps from vibrant Winchester Center in this beautifully renovated 2016 condo. High ceilings & gleaming HW floors flow throughout this spacious, light-filled home, w/an open floor plan that features fireplaced living & dining area adjoining a chef’s eat-in kitchen, outfitted w/ SS appliances & granite countertops.The home offers 3 generously sized bedrooms & 2 full bathrooms, including a luxurious primary suite w/a custom walk-in closet & spa-like double-vanity bathroom. 2 additional flexible rooms are perfect for a home office, playroom, dining room, or sunroom, offering wonderful sunset views.Exceptional storage is found throughout, including generous custom closets, a pantry, & a large walk-out basement w/ potential for future expansion. Private fenced-in yard w/patio & garden area, plus side-by-side parking for up to 4 vehicles.This turnkey home offers oversized windows & central air, located about half mile from scenic Middlesex Fells & commuter rail.

16 Park Ave Unit 2, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,200,000
5 Beds ⋅ 2 Baths ⋅ 73440354 MLS
This well-maintained two-family home offers desirable one-level living on each floor & is filled with/natural light throughout. Both units feature high ceilings, HW floors, replacement windows, & generous storage.The 1st floor unit includes 2 BR, an eat-in kitchen, full bath, & open-concept DR & LR w/ built-in china cabinet. The 2nd floor unit has been tastefully renovated, featuring a modern kitchen w/granite countertops, SS appliances, & peninsula w/seating.The updated bath & den add to the appeal, while the DR w/ built-in china cabinet opens to a spacious living room.This unit also offers 3 BR, a bonus office space, & the comfort of central AC. Additional updates include a newer roof, new siding, new gutters, & a new boiler for Unit 1. Enjoy a fenced-in yard w/a patio & side-by-side driveway parking conveniently located on a side street. Ideally located just 0.2 miles from the highly rated Muraco school, half mile from the Fells, & less than a mile from Winchester center.

415-417 Washington Street, Winchester

Listing courtesy of Listing Agent: Paula R. Sughrue from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$2,600,000
5 Beds ⋅ 4 Baths ⋅ 73419963 MLS
Thoughtfully renovated & meticulously maintained, this classic colonial home in the Flats invites with timeless charm & modern conveniences. Through the center entrance be welcomed into the fireplaced living room & dining room- both refreshed in 2025 with new lighting, paint & wallpaper. The open-plan custom kitchen with marble counters, stainless appliances, and a butler’s pantry with sink, granite counters, and second dishwasher make this a wonderful home for entertaining. The second floor features a primary suite with walk-in closet & marble bath w/ soaking tub, 3 generous bedrooms with a full hall bath, and a laundry-ready closet. The lower level offers an excellent option for guests with a bedroom & ¾ bath, plus an office, laundry room & playroom. Plentiful closets & functional storage space abound throughout this home. The professionally landscaped yard is a welcoming spot to entertain on the deck & bluestone patio, or relax & play in the flat back yard.

48 Salisbury Street, Winchester

Listing courtesy of Listing Agent: Katie Tully from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,199,000
3 Beds ⋅ 4 Baths ⋅ 73415198 MLS
NEW CONSTRUCTION!! Welcome to this meticulously crafted, modern townhouse END UNIT offering over 2,100 sq ft of thoughtfully designed living space. The open-concept main level features gorgeous mill work, gleaming hardwood floors, a cozy fireplace & sleek chef-inspired kitchen w/ stainless appliances, large center island & an adjacent mudroom w/ half bath perfect for today’s lifestyle. The 2nd floor includes 2 generous bedrooms & a stylish full bath, while the top level is dedicated to the luxurious primary suite w/ a spa-like en-suite bath & great custom closet space. The finished lower level provides flexible space ideal for a family room, home gym, or office, complete with a full bath. Enjoy the convenience of two off-street parking spaces with an EV charger & a location that’s a commuter’s dream just minutes to the train, I-93, Route 128, Logan Airport, & downtown Boston. This exceptional home is close to Winchester Center’s shops, schools, restaurants & all the town has to offer!

162 Swanton Street Unit 162, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,355,000
4 Beds ⋅ 3 Baths ⋅ 73441705 MLS
Welcome to the Winchester Highlands! This inviting 4-bedroom, 2.5-bath home blends comfort and character in the desirable Lincoln School District—just a short distance to downtown Winchester, the commuter rail, I-93, and the Middlesex Fells. A sun-filled living room with custom stone fireplace flows seamlessly into the dining area, perfect for gatherings. The kitchen offers a vented gas range, light maple cabinetry, and a peninsula with views of the private backyard oasis featuring a stone patio and tree lined property. Enjoy easy single-level living with four bedrooms and 1.5 baths on the main floor, including a spa-inspired bath with walk-in shower and whirlpool tub not to mention hardwood floors throughout. The finished lower level offers a family room, home gym, full bath, laundry, and direct garage access. Thoughtfully maintained with many homeowner improvements, this home combines warmth, functionality, and timeless appeal in one of Winchester’s most sought-after neighborhoods.

4 Sargent Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
$3,599,000
6 Beds ⋅ 5 Baths ⋅ 73420138 MLS
This extraordinary, fully renovated home blends rich architectural detail w/ modern luxury in one of Winchester’s most sought-after neighborhoods. Designed by a shipbuilder, this home offers 5,876 sq ft of elegant living space filled w/ natural light, coffered ceilings, crown moldings, restored hardwood floors & more. The breathtaking chef’s kitchen includes a quartzite island, 8-burner Wolf range, paneled appliances, & wine bar. The first floor features generously sized rooms that flow beautifully, offering grand entertaining spaces, 4 fireplaces, & a statement staircase. Upstairs offers 4 bedrooms & 3 updated baths, including a serene primary suite w/ fireplace, marble bath & double closets. The third floor includes 2 add'l. beds, full bath, & room for expansion. Enjoy a private fenced yard w/ lush gardens, patio, & a 2+ car garage. With timeless character and thoughtful updates throughout, this is a rare opportunity just moments from town, train, and top schools!

5 Stratford Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$8,000
4 Beds ⋅ 4 Baths ⋅ 73398859 MLS
No Broker Fee! Large Sun-filled Windows, Contemporary, Minimalist, and Modern Design. A truly rare opportunity to rent this magnificent single-family home in one of Winchester’s most desirable neighborhoods. The home was ground-up construction in 2010 with over 3,500 square feet of living space. Its open concept, large loft-style office / second living room area, four bedrooms, three and a half bathrooms, attached 2 car garage, and plush landscaping leaves nothing left to be desired. Do not miss out on this one - these opportunities don’t come around often.

35 Thornberry Road, Winchester

Listing courtesy of Listing Agent: Frank Celeste from Listing Office: Gibson Sotheby's International Realty.
$1,987,000
4 Beds ⋅ 4 Baths ⋅ 73416647 MLS
Step into comfort and sophistication in this beautifully curated Colonial, where thoughtful design meets everyday luxury. A spacious kitchen anchors the main level, showcasing quartz countertops, a generous breakfast bar & seating area complemented by a central island. The kitchen flows effortlessly into a family room lit by skylights, wood fireplace & soaring ceilings. Just beyond, a step-up private office offers a private & inspiring space for the at-home professional. The separate dining room is ideal for entertaining, while the eat-in kitchen provides a casual space for daily meals. Upstairs, a vaulted-ceilinged primary bath impresses with dramatic windows and a serene ensuite bath. All 4 bedrooms are spacious with plenty of natural light. The finished lower level is a dream—complete with a bonus room, game room, exercise room, and full bath—versatile enough to suit any lifestyle. Outside, the private backyard features a stunning stone patio, professional landscaping, & a hot tub.

6 Samoset Rd, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$3,900
3 Beds ⋅ 3 Baths ⋅ 73453104 MLS
Newly renovated Town home at The Village in Winchester offers an idyllic condominium community nestled near conservation land and the Aberjona River. This 3-bedroom home features a spacious living room with a gas fireplace and a dining area leading to a private patio. The kitchen was renovated in 2023. The main level includes a half bath and ample storage. Upstairs, the master bedroom has plenty of closet space and a private bath with a walk-in shower. Two more bedrooms, a laundry area, and extra closets are upstairs. This unit comes with a garage and two more parking spaces. The community features landscaped grounds, a tennis court, pool, and clubhouse. Enjoy these amenities within walking distance of Winchester's town center, commuter rail, and shops. The complex offers pool and tennis court as well. Tesla wall charger comes in the Garage. Unit comes with TESLA WALL CONNECTOR.

171 Swanton St Unit 65, Winchester

Listing courtesy of Listing Agent: Yuanming Cheng from Listing Office: Dreamega International Realty LLC.
$2,450,000
6 Beds ⋅ 6 Baths ⋅ 73442428 MLS
NEW HIGH-END CONSTRUCTION - 13 Rms - 6 BD's - 5.5 BA's You will be captivated by the grand entrance - attention to detail - high coffered 10' ceilings and excellent flow that leads you to the magnificent Open Floor Plan - custom-designed Kitchen which is the heart of this home. no expense was spared; custom Cabinets, Thermador appliances, oversized Center Island; Living Rm/Great Rm w/FP, Dining Rm, Butler Pantry, Mud Rm, Laundry, Powder Rm and Guest BD w/BA. The 2nd flr offers 4 BD's w/BA's, gorgeous Master Suite w/BA and Laundry, FP and custom-designed oversized Walk-in Closet. Finished Lower Level has spacious Family/Game Rm w/custom cabinets and Bar, Office/Exercise Rm and full BA - perfect space for a NANNY/IN-LAW SUITE. Professionally landscaped Yard, Patio - Deck - oversized 2-Car Garage - plenty of land for a pool; Enjoy Winchester amenities, minutes to Center, top-rated Schools, Fells Reservation, Parks, Restaurants, Shopping, Commuter Train, major routes - 8 miles to Boston.

382 S. Border Road, Winchester

Listing courtesy of Listing Agent: Lucille Murray from Listing Office: Gibson Sotheby's International Realty.
$1,225,000
2 Beds ⋅ 2 Baths ⋅ 73437251 MLS ⋅ ['Winchester Place'] BLDG.
Elegant and expansive condo with soaring ceilings in the sought-after Winchester Place, just moments from the vibrant town center, boutique shops, idyllic Mill Pond, newly improved commuter rail, and so much more. Offering over 1,500 square feet of refined living, this home showcases gleaming wood floors, sun-filled open living room with a dedicated dining areas for hosting, and a beautifully designed kitchen with built-in cabinets, abundant counter space, and direct access to a private deck. The spacious primary suite features a full bath with a soaking tub, complemented by a second well-appointed bedroom. Enjoy the convenience of in-unit laundry, two deeded garage spaces, your own basement storage room, and modern amenities like central air and a cozy fireplace, adding to the timeless appeal of this exceptional home.

10 Winchester Pl Unit 301, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$1,250,000
5 Beds ⋅ 2 Baths ⋅ 73434284 MLS
Luscious landscaping and a beautiful farmers porch create amazing curb appeal for this classic colonial in the coveted Muraco School district. Offering a lovely floorplan which offers a welcoming foyer which allows access into the front living room, formal dining room and directly into a large kitchen with plenty of cabinets and granite countertops. The second level features a full bath as well as 3 sunlit bedrooms which include a primary bedroom with private ensuite bath. The walk up third floor is appointed with 2 additional bedrooms and ample storage space. Additional highlights include central air, storage shed, sprinkler system and fully fenced in yard. The home sits with convenient access to major highways, Winchester center and the commuter rail.

35 Harvard Street, Winchester

Listing courtesy of Listing Agent: Joanne Mulkerin from Listing Office: J. Mulkerin Realty.
$397,000
1 Beds ⋅ 1 Baths ⋅ 73427774 MLS ⋅ ['Parkview Condominiums'] BLDG.
OPEN HOUSES CANCELLED !Move right into this immaculate, renovated walk-in condo with an oversized layout and a highly sought-after private terrace patio. Terrace units rarely go on the market—don’t miss this opportunity to purchase a unit in the best location in the building. The sun-filled home offers an eat-in kitchen with granite counters, modern cabinets, newer stainless-steel appliances, and a dining area overlooking the tranquil duck pond and landscaped grounds. Updates include fresh paint, new lighting, bathroom mirror, kitchen tile floor, slider blinds, and gleaming hardwood floors. The spacious living room opens directly to the private patio, perfect for relaxing or entertaining. Enjoy resort-style amenities in this gated community: sparkling pool, BBQ area, storage, laundry close to the unit, and ample parking. A low condo fee covering heat, hot water, A/C, electric, water, and sewer adds exceptional value. Conveniently located near the train, downtown, shops, and restaurants

200 Swanton St Unit T11, Winchester

Listing courtesy of Listing Agent: Shannon Jenkins from Listing Office: RE/MAX Realty Experts.

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