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$1,165,000
3 Beds ⋅ 3 Baths ⋅ 73415423 MLS
Welcome to this stunning updt’d 3-bed, 2.5-bath multi-level home in one of Winchester’s most desirable neighborhoods, just two blocks to Vinson-Owen Elementary! Freshly painted inside&out for a modern, crisp feel, the home offers a perfect blend of style, comfort, convenience. Open layout with a beautiful fireplace, living room, bay windows, and formal dining room lead to a spacious deck and patio, ideal for entertaining. Stylish kitchen offers brand-new stainless steel appliances, white cabinetry, and tiled floors. Gleaming hardwoods flow throughout the main level with a serene primary suite, 2 generous bedrooms (one convertible to 2), and full bath. LL includes an office, cozy family room, half bath, and laundry. Features professionally landscaped grounds with irrigation, private backyard oasis, and central vac system. 9mi to Boston, enjoy the best of both worlds: close to town center, Fells, parks, dining, shopping, commuter rail, Wright-Locke Farm, and Winchester Swim &Tennis Club.

59 Johnson Rd, Winchester

Listing courtesy of Listing Agent: Angela Y. Zhang from Listing Office: Greatland Real Estate LLC.
$382,000
1 Beds ⋅ 1 Baths ⋅ 73409690 MLS ⋅ ['Parkview'] BLDG.
This beautifully maintained one-bedroom condo at Parkview offers exceptional value in Winchester—one of Massachusetts’ most desirable towns. Conveniently located within the building, this bright and inviting unit features a stylish kitchen with granite countertops and modern cabinetry, plus a renovated bathroom with contemporary finishes. Enjoy peaceful views from the private balcony. The well-maintained, gated community includes a pool, picnic area, cabana, on-site laundry, and ample parking. Just minutes to downtown Winchester, the commuter rail to Boston, and highly rated Winchester public schools. Also near local healthcare, dining, shops, parks, and walking trails. The monthly condo fee includes heat, AC, electricity, hot water, water, sewer, swimming pool, landscaping and more! With its unbeatable location and move-in-ready condition, this is one you won't want to miss!

200 Swanton St Unit 432, Winchester

Listing courtesy of Listing Agent: Mark Gilson from Listing Office: Keller Williams Realty.
$3,200
4 Beds ⋅ 2 Baths ⋅ 73439643 MLS
Great Location! Available now this 3 floor Townhouse features kitchen, living room, 1/2 bath and dining room. Second floor has 2 bedrooms, full bath and office space. Third floor has 2 bedrooms. Off street parking, small back yard and basement for Washer Dryer hook ups and storage. Hardwood through out and freshly painted. Great front porch to relax on. Convenient to Schools, Restaurants, Shopping and Major Highway access. Tenant is to pay Gas, Electric and Cable. First and Last is due at signing of lease. You will need to pay for a sticker for trash. The Tenant is responsible to purchase sticker at Transfer Station in Winchester, and cost is 340.00 for year.

45 Vine Street Unit 45, Winchester

Listing courtesy of Listing Agent: Robin Griffiths from Listing Office: J. Mulkerin Realty.
$2,862,500
6 Beds ⋅ 4 Baths ⋅ 73428556 MLS
Exceptional value, prime living in this stunning home w/ spectacular resort style back yard surrounded by mature plants and trees encompassing the gorgeous yard/setting. Completely updated throughout w/ custom high end finishes, open floor plan, wonderful chefs kitchen w/ Sub Zero- Wolf appliances, sunny breakfast/dining area w/ a wall of windows overlooking expansive backyard featuring gorgeous patio & maintenance free heated POOL w/ in- floor cleaning system & auto cover! Inviting covered rear porch /gazebo for outdoor living complete with movie night projector! Impressive family rm w/ views of yard, gas fireplace & built in bookshelves . Stylish formal dining rm w/ bay window & custom wainscoting, front to back LR w/ fplc; grand rooms, detailed moldings, updated baths, primary suite w/ 2 walk in closets, spa like bath w/oversized shower & soaking tub. Full 3rd floor w/ 3 Beds & full bath, new heating/ cooling, newer roof. 2 car garage w/space above & basement awaits finishing!

54 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,600,000
5 Beds ⋅ 4 Baths ⋅ 73362881 MLS
Come see this spacious 5-bedroom home offered at a NEW PRICE of $1,769,000! Located near the end of a quiet cul-de-sac in a wonderful neighborhood, this home offers privacy, space and natural beauty, just a short distance to Winchester Center and surrounding towns. Walking distance to the Vinson-Owen school, which has consistently been rated as one of the best elementary schools in the state. Set on an 18,000 sq ft lot that backs up to a wooded conservation area with walking trails. All 5 bedrooms and 3 full baths are situated on the second floor, including a cathedral-ceiling primary bedroom/bath with skylights and a steam shower. The main level features an office/den/potential guest room, a large living room/dining room combination leading to a screened-in porch overlooking serene woodlands, a half bath, a bright kitchen with lots of storage and water filtration system. The spacious walk-out lower level provides plenty of room for a playroom/family room/gym and has great storage.

10 Olde Lyme Road, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 73410427 MLS
Beautifully renovated multi-level home in top location abutting the town forest conservation/ walking trails & just minutes from downtown Winchester! This move-in ready property features many recent upgrades, 3+ bedrooms, hardwood floors w/an open concept spacious layout perfect for modern living. The large updated kitchen includes high-end appliances, gas stove, beverage fridge & an oversized island with plenty of prep and seating space. Enjoy meals in the dining area with a custom built-in banquette. The open living area features an oversized living room with fireplace, the adjacent sunroom/ home office or 4th bedroom overlooks the back yard and town forest-ideal for relaxing or entertaining. Additional highlights include large bedrooms, a primary with ensuite bath, a large LL family room w/ bar, fireplace & a 2-car garage plus 3 season bonus room. Many flexible living spaces for a home office or guests w/ thoughtful updates throughout. A must-see home in a peaceful perfect setting!

17 Dennett Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$519,000
1 Beds ⋅ 2 Baths ⋅ 73424752 MLS ⋅ ['Church Place'] BLDG.
Welcome to Church Place in Winchester. This light-filled one-bedroom condo offers a unique two-level layout with beautiful windows that frame picturesque views of the town. The main level features an airy, open-concept living and dining area, highlighted by a cathedral ceiling in the living room making it perfect for entertaining or enjoying a quiet evening at home. Upstairs, you’ll find a cozy retreat with the bedroom and bath, creating a sense of privacy and comfort. Additional features include in-unit laundry and a designated parking space for everyday ease. Step outside and experience the vibrant lifestyle Winchester has to offer, just moments from the town center with its inviting shops and restaurants, the weekly farmers market, library, town common, and more! Commuters will appreciate the close proximity to the commuter rail, offering quick access to Boston and beyond. This condo blends character, light, and location, making it a perfect place to call home!

115 Washington St Unit 3D, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$1,185,000
3 Beds ⋅ 4 Baths ⋅ 73420622 MLS
Gut renovated charming home sets back on a private way near downtown. This sun drenched home features hardwood floor, custom tile work, meticulous woodwork, wainscot, skylights, cathedral ceiling, marble bath, amazing custom mantles FP along w/all 3.5 designer baths w/all the fancy stone work and unique vanities. Open floor plan 1st fl. features large LivRm w/lots of custom touch which leads to Gourmet kitchen features cathedral ceiling, sky light, granite counter, SS appliances, wet bar & breakfast area. Kitchen has direct access to sunny deck which leads to back yard for perfect outdoor entertaining & relaxation. Jr. Master suite w/jacuzzi is conveniently located in 1st fl. Main Master suite in the 2nd fl. is equipped w/gas FP, cathedral ceiling & skylight. Custom wood work in lower level has 3rd bedroom w/en-suite bath. Stone paver walkway surrounded by tall greens w/plenty of parkings. Closed to Winchester Center, Restaurants, Middlesex Fells Reservation and Winchester/Commuter

5 Emerson Court, Winchester

Listing courtesy of Listing Agent: H. Elaine Song from Listing Office: Coldwell Banker Realty - Lexington.
$1,280,000
4 Beds ⋅ 2 Baths ⋅ 73407455 MLS
Located in the popular Winchester Highlands neighborhood with Elegance and Stature is this 4 bed, 1.5 bath Center Entrance Colonial with 2 car garage, minutes to I-93 and Winchester Center with boutique shops, cafes, restaurants, and newly renovated MBTA Station. Welcoming front vestibule opens to sprawling front-to-back living room with wood burning fireplace and attached sunroom. Formal dining room with chair rail and crown molding leads to 2019 updated kitchen with new gas range, exhaust hood, countertops and hardware. A rear vestibule and mudroom with half bath complete this level. Natural woodwork and crown molding throughout the main level. Mini splits provide comfortable A/C throughout. Architectural tilt-in Pella windows in all rooms except sunroom. Detached 2 car garage with full basement offers great potential for ADU, plus a large driveway for 5+ cars. Level yard with new fence, granite stairs, stone wall and patio, perfect for entertaining and relaxing.

162 Forest St, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
$2,575
2 Beds ⋅ 2 Baths ⋅ 73420760 MLS
Located at 35 Vine Street U:306, Winchester, MA, this residential property offers a superb opportunity to enjoy refined living. Situated on floor number 3, this home presents a wonderful chance to live in a comfortable residence in a vibrant community just steps to Winchester Center and Commuter Rail. The residence features two full bathrooms, providing convenience and privacy for yourself and guests alike. Enjoy the ease of 1-floor living, elevator in lobby and 2 assigned parking spots. (1 spot in garage under w/automatic door opener, 1 in parking lot). Laundry in building. Heat and hot water included. Central A/C. Newly carpeted throughout. Dishwasher /disposal /over-the-stove microwave. Available NOW or September 1st.

35 Vine Street Unit 306, Winchester

Listing courtesy of Listing Agent: Jill Shanley from Listing Office: CJL Rentals & Property Management Co., Inc..
$4,800
3 Beds ⋅ 3 Baths ⋅ 73422112 MLS
Don’t miss the opportunity to lease this beautifully maintained multi-level single-family home, nestled on a quiet and private dead-end street. Recently updated with fresh interior paint and refinished hardwood floors, this spacious residence offers over 2,300 square feet of comfortable living space. Enjoy central A/C, a generous kitchen with an open-concept dining area—perfect for both everyday living and entertaining—and a large, private, and beautifully landscaped backyard. Ideally located just minutes from the highly rated Vinson Owen Elementary School, local parks, and public transportation. Available September 1st.

12 Trinity Road, Winchester

Listing courtesy of Listing Agent: Michael Rauseo from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
$1,800
1 Beds ⋅ 1 Baths ⋅ 73419090 MLS
A lobby level studio / one bedroom condo in the center of Winchester to rent. Beautiful views of the courtyard and many updates over the past few years, including granite countertops, sink and appliances. Well managed building has gone through some recent renovations and upgrades including new landscape, paved driveways and walkways. This Back Unit is overlooking The Pond. ALL utilities (heat, A/C and even electric) are included in the rental. Common coin-op laundry rooms, pool, card-entry gated complex. Very close to Winchester town center, schools, restaurants, and major highways 93/95 and Middlesex Fells. Extra storage room and close to Fells Reservation.

200 Swanton Unit L6, Winchester

Listing courtesy of Listing Agent: WINN Rental Team from Listing Office: WINN Real Estate & Consulting.
$6,000
4 Beds ⋅ 4 Baths ⋅ 73409522 MLS
Discover elegant living in this stunning Winchester duplex offering exceptional space and comfort across four thoughtfully designed levels. Ideal for both relaxation and entertaining, the home boasts an expansive kitchen flowing seamlessly into inviting dining and spacious family areas. Retreat upstairs to generously sized bedrooms, each designed for restful privacy, including the ensuite primary bed & bath, complemented by a dedicated home office ideal for remote work. Additional highlights include a finished lower-level room for exercise, hobbies, or to be a playroom. Complete with central air conditioning, garage parking, and ample off-street parking, this residence is the most versatile rental on the market. Renting for September 1st, 2025.

192 Cross St Unit 192, Winchester

Listing courtesy of Listing Agent: Anne Spry from Listing Office: Barrett Sotheby's International Realty.
$738,000
3 Beds ⋅ 3 Baths ⋅ 73422508 MLS ⋅ ['The Village In Winchester'] BLDG.
Well kept, end-unit townhouse at The Village offering a blank slate for new owners to update or renovate to their precise desire! End unit means you have more windows, more natural light and 3 parking spots (1 garage spot w direct access into the home & EVSE charging unit, 1 spot in front of your garage AND 1 spot adjacent)! Kitchen has an opening to the dining room that has fabulous, vaulted ceilings and skylights offering even more natural light. Dining room also offers direct access to your private patio and common grass beyond. Large, front-to back living room offers gas fireplace and built-in shelving. Full size, side-by-side laundry is ideally located on 2nd floor along with all 3 bedrooms. Principal suite offers walk-in-closet and en suite bath. Verizon Fios available for entertainment. The Village is a professionally managed 80-unit townhouse complex built in 1984 (lead free!) with in-ground pool, tennis courts and clubhouse! Just a couple minutes to Winchester Center!

171 Swanton St Unit 60, Winchester

Listing courtesy of Listing Agent: Michaela Hellman from Listing Office: Redfin Corp..
$878,000
3 Beds ⋅ 2 Baths ⋅ 73421565 MLS
Here's your chance to get into Winchester! Currently the only home under a million dollar! A short distance off Route 93 montvale exit, makes this location great for commuting to Boston; route 2 or NH! Charming 3-bedroom, 1.5-bath single-family home located on a quiet dead-end street, offering peace and privacy. This property boasts a spacious yard—perfect for gardening, outdoor entertaining, or play. Inside, a functional floor plan, and an abundance of natural light throughout. While it's in move in condition, the the interior is dated and awaits your personal touch. Don’t miss this opportunity to make it your own! The house and yard have endless possibilities! Vacant and ready to go!

17 Baldwin St, Winchester

Listing courtesy of Listing Agent: Dennis Oliveira from Listing Office: JDS Realty Group.
$1,475,000
2 Beds ⋅ 3 Baths ⋅ 73416503 MLS
Meticulously maintained, 2-bedroom, 2.5-bath townhome with 2 car garage. The kitchen features custom cabinets, granite countertops, high-end stainless steel appliances and gleaming hardwood floors. The living/dining room combo features hardwood floors, gas fireplace, cathedral ceilings along with french doors that open to a private patio with gas grill. Spacious first floor primary suite boasts a full bath with a walk-in custom shower and large walk-in closet and first floor laundry area, just outside the kitchen. Second floor offers a spacious loft family room, perfect for office or sitting area and a large second bedroom with full bath and walk-in closet. Some units have converted office into a third bedroom. Large basement with high ceilings that could be finished into extra living space.

60 Graystone Cir Unit 60, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Advisors Living - Winchester.
$1,713,000
3 Beds ⋅ 3 Baths ⋅ 73385650 MLS
Picture your family in this unique colonial, just one street over from the amazing Vinson-Owen school! 2 sizeable, private yards with lush grass, flagstone patios and even a dining room deck! Lots of upgrades include a new family room with brick wall, computer cubby, cathedral ceiling & mahogany deck. There's 3 bedrooms to start, including a spacious Primary Suite with walk-in closet, large dressing area and full bath, but an incredible home office easily converts back to the 4th bedroom! Everything you could want in a nearby school location is here- wood floors, granite counters & crown molding throughout! Check out the Great Room with fireplace, plus a finished basement, renovated bathrooms, stainless steel appliances, central air, sprinkler system and 2 car garage. You'll love it when you see it!

44 Amberwood Drive, Winchester

Listing courtesy of Listing Agent: Santana Team from Listing Office: Keller Williams Realty Boston Northwest.
$1,678,500
4 Beds ⋅ 2 Baths ⋅ 73409731 MLS
Welcome to 10 Blossom Hill Road. Tucked away in a cozy and desirable West Side Winchester neighborhood, this enchanting storybook home is full of warmth, charm, and heart. Here you will find a lovingly cared-for 4-bedroom home with a guest or in-law suite offering wonderful flexibility to suit your needs. Inside, you’ll find light-filled spaces, thoughtful updates, and timeless character that make every room feel special. Outside, the magic continues—a private yard and lush gardens create a peaceful oasis, perfect for relaxing, entertaining, or simply enjoying the beauty around you. Just minutes from the town center, top schools, and commuter routes - so close to everything yet so far away from it all. Loved and admired for its charm, this is a home where memories are made and life feels just right. Now ready to begin its next chapter with someone who will live here, enjoying all that it offers, and love it just as much for years to come

10 Blossom Hill Rd, Winchester

Listing courtesy of Listing Agent: Stephen DeConto from Listing Office: Cameron Real Estate Group.
$1,950,000
5 Beds ⋅ 4 Baths ⋅ 73394140 MLS
Nestled in a desirable Westside neighborhood, this stunning California contemporary/colonial home sits on a quiet cul-de-sac and offers 5 bedrooms, 3.5 baths, and over 20,000 sq ft of beautifully landscaped grounds. The sun-drenched interior features an open-concept kitchen and dining room with five fully opening doors leading to a bright four-seasons sunroom—perfect for gatherings year-round. The home includes two fireplaces, a freshly painted interior, and a finished basement with a full bath. A spacious oversized garage provides ample storage and parking.Enjoy tranquil views from the greenhouse and sunroom overlooking a serene koi pond with a cascading waterfall. The lush yard includes raised vegetable garden beds, vibrant flowers, and mature landscaping—a private oasis right at home. Walking distance to VO Elementary School, this home offers an ideal combination of style, space, and location. Don't miss the opportunity to make this exceptional property your own

4 Fieldstone Dr, Winchester

Listing courtesy of Listing Agent: Wenli Zheng from Listing Office: Fairview Partners International LLC.
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 73366046 MLS
Call for a private showing anytime! Discover this charming renovated 3 bed 2 bath home with close proximity to the Fells trails & Winchester town center including schools, train to Boston, restaurants, shops & all the town has to offer!! Beautifully renovated & lovingly maintained, this great home welcomes you w/ a spacious living room w fplc that flows seamlessly into a sun-drenched updated kitchen featuring stainless steel appliances & stylish finishes w/open concept dining, oversized windows & slider to deck. A family room just off the main living area offers a cozy, versatile space & potential for another BR w/ full 1st floor bath. The expansive back deck is ideal for dining, entertaining, or simply unwinding overlooking a large grassy rear yard- a gardeners dream w/ layers of terraced vegetable gardens plus plenty of space for family fun! The second floor offers three great BR's including a vaulted primary & full bath. A detached garage completes this perfect home, move right in!

147 Highland Ave, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
$1,890
1 Beds ⋅ 1 Baths ⋅ 73420546 MLS
Available Oct 1Bright and inviting top-floor studio condo at the sought-after Parkview community. This unit features a private balcony overlooking the pond, perfect for enjoying peaceful views. Rent includes heat, hot water, electricity, and air conditioning for added convenience. Residents benefit from on-site laundry, parking, and access to the community pool. A well-maintained building in a great location with easy access to major routes, shopping, and dining.

200 Swanton St Unit 708, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: Advisors Living - Merrimac.
$1,780
1 Baths ⋅ 73416349 MLS
All utilities included! Available now! Studio apartment on the 7th floor in Winchester with a private balcony overlooking Duck Pond. Heat, hot water, AC, and electricity included. Building amenities include an elevator, outdoor swimming pool, visitor parking, and 1 free parking pass (additional parking available at extra cost to HOA). Convenient location close to shopping, restaurants, and major highways. Enjoy comfortable and affordable living in this well-maintained building

200 Swanton Unit 738, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: Advisors Living - Merrimac.
$287,000
1 Beds ⋅ 1 Baths ⋅ 73417947 MLS
Immaculate, studio condominium within the desirable Parkview Condominiums in Winchester. This unit is located on the east side of the building, where it is filled with natural sunlight. The large private balcony overlooks a beautiful wildlife pond, and the grounds are meticulously landscaped. The kitchen features tile flooring, updated granite countertops, and a breakfast bar. The Condominium amenities include: in-ground swimming pool, barbecue area, large parking area with plenty of overnight guest parking, on-site laundry rooms, on-site management, and private storage units. The low condo fee includes: heat, hot water, trash services, electricity, and air conditioning. Winchester is a quaint and charming New England town, only 8 miles north of Boston. This amazing location is only two blocks from Winchester center, shops, restaurants, parks, and the commuter rail. Don’t miss this exceptional opportunity!

200 Swanton St Unit 402, Winchester

Listing courtesy of Listing Agent: Michael Masci from Listing Office: North Atlantic Realty Group.
$1,725,000
3 Beds ⋅ 3 Baths ⋅ 73417086 MLS
Welcome to this beautiful split-level home nestled on a desirable corner lot in Winchester’s sought after west side. Featuring gleaming hardwood floors throughout, this home offers a perfect blend of comfort and style. The main level boasts an open floor plan connecting the dining room, kitchen, and living room, and seamlessly flows into a stunning vaulted family room, perfect for both everyday living and entertaining. Three spacious bedrooms and two full baths are located on this level, which includes a serene primary suite. Step out from the family room onto the screened in porch with a relaxing hot tub or enjoy outdoor gatherings on the deck overlooking the private, landscaped yard. The lower level offers a versatile additional family room with direct access to a full bath and laundry area, providing the perfect space for guests, a playroom, or a home office. With a two-car garage, central air, generous natural light, and a thoughtful layout, this home truly has it all.

9 Pilgrim Dr, Winchester

Listing courtesy of Listing Agent: McGlynn & Nigro Team from Listing Office: Berkshire Hathaway HomeServices Commonwealth Real Estate.
$4,200
3 Beds ⋅ 3 Baths ⋅ 73427093 MLS
Charming townhome in The Village at Winchester offers serene living near conservation land, 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 + assigned driveway parking, 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.
$1,465,000
4 Beds ⋅ 3 Baths ⋅ 73409241 MLS
4 BD, 2.5 BA home tucked away from the road for added privacy. Kitchen has spacious dining area for enjoying family meals & entertaining guests. Inviting family room, w/ FP brings warm ambiance & convenient access to the deck, enhancing your indoor-outdoor living experience. Large living/dining area w/ backyard views is a versatile space w/ an open layout make it a welcoming spot. Convenience is key, w/ 1st-floor laundry area & spacious 2-car garage w/ storage. This 0.65-acre lot features a large fenced backyard with a deck, patio, & screened-in gazebo—perfect for relaxing, entertaining, or enjoying outdoor activities. Heated & A/C bonus room on 2nd floor provides flexible options for expansion, making it an ideal space for home office, studio, playroom, or guest suite. Expansive 1,100 sq ft LL is a blank canvas ready to be transformed to suit your needs. 1.4 miles to downtown Winchester & the commuter train, this home provides easy access to amenities & transportation. A must see gem!

6 Highland Ave, Winchester

Listing courtesy of Listing Agent: Peter Rooney from Listing Office: Compass.
$1,945,000
5 Beds ⋅ 5 Baths ⋅ 73408155 MLS
Another Tree Top Group masterpiece—where natural light, luxury finishes, & thoughtful design come together in perfect harmony. This 5-bed, 4.5-bath new construction home boasts 9+ ft ceilings, exceptional light fixtures, and a stunning waterfall center island that anchors the designer kitchen w/ custom cabinetry that extends to the ceiling. Custom built-ins & storage throughout. A sleek linear fireplace adds warmth to the open-concept family room. With two primary suites to choose from, flexibility meets luxury. The third-floor primary feels like a private hotel retreat w/ a sitting area, dual walk-in closets, & a spa-inspired bath. The second-floor primary offers a spacious en-suite & walk-in closet. Finished lower level includes a fifth bedroom, full bath, wet bar, & bonus living space. Additional highlights: mudroom, EV-charger ready setup, & a rear deck with a spacious backyard. Located minutes from Winchester Center, commuter rail and top-rated schools—this is a rare opportunity!

20 Grayson Rd, Winchester

Listing courtesy of Listing Agent: The Marrocco Group from Listing Office: Coldwell Banker Realty - Lexington.
$505,000
2 Beds ⋅ 1 Baths ⋅ 73410035 MLS
Sunny second-floor 2-bedroom unit overlooking a serene duck pond. This home features an open layout with hardwood floors, an updated granite and stainless-steel kitchen, and a modern bath with a sleek barn door. Each bedroom offers two closets, plus three additional hallway closets for exceptional storage. Enjoy a private enclosed balcony with serene views. The HOA fee includes heat, hot water, and AC. Community amenities include two large laundry rooms, a seasonal pool, storage unit, and ample parking. Ideally located near downtown Winchester, the commuter rail, and major highways.

200 Swanton St Unit 239, Winchester

Listing courtesy of Listing Agent: Joan Powell from Listing Office: Advisors Living - Merrimac.
$1,770,000
3 Beds ⋅ 3 Baths ⋅ 73409381 MLS
This carefully crafted Colonial, custom-built by Andrew Pywell, combines solid construction with a bounty of special touches and timeless charm. Delight in sun-splashed living spaces, gleaming hardwood floors, crown moldings, and a layout that balances an open flow, defined spaces and beautifully proportioned rooms across 2,850 square feet. The gracious formal living room, dining room, and inviting family room offer endless entertaining possibilities. The expansive primary suite upstairs includes an ensuite bathroom, walk-in closet/dressing room, walk-in cedar room, and plenty of additional storage. The unfinished attic (with electric!) awaits your design plans! An unfinished basement is plumbed for a bathroom and sump pump. Outside, you'll find a beautifully landscaped lawn and gardens with a picturesque Beacon Hill-style yard. Located just steps from absolutely all that Winchester has to offer! A true walk-to-town gem with every Winchester amenity right at your doorstep.

178 Mystic Valley Pkwy, Winchester

Listing courtesy of Listing Agent: Katherine Waters Clark from Listing Office: Compass.
$1,100,000
3 Beds ⋅ 2 Baths ⋅ 73407591 MLS
OFFER DEADLINE TUE JULY 29th 5:00PM | Exceedingly charming + in-town location to be envied. Shops, schools + both MBTA stations at your fingertips. Step up onto your porch, pass the bench swing you’re yet to install; entering into the inviting foyer w/ original stairs preserved & tall ceilings. The main level is sophisticated & functional. A front facing dining room w/ plantation shutters + oversized windows flows into a well laid-out kitchen for the chef in the family! Direct patio access, ½ bath & custom pantry closet + laundry. Beyond your bar/coffee station a sophisticated living room awaits anchored by a gas FP w/ built-ins feat. grass cloth backed glass shelves. The 2nd level offers 3 bedrooms; a primary with walk in closet & custom drapery. Newly updated bath is soothing + sports radiant floors for those crisp fall mornings. The grounds are landscaped w/ a patio for alfresco dining, tidy flat yard & darling storage shed. Pkg. for 3+ cars & basement for storage/workshop. Perfect.

5 Cutting Street, Winchester

Listing courtesy of Listing Agent: Oliver Koester from Listing Office: Compass.

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