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22 Arthur St Unit 22, Winchester
$414,500
2 Beds ⋅ 1 Baths ⋅ 73522504 MLS
This property is available to and priced for Income Eligible families in 100% of the moderate-income range. See attached application for eligibility requirements. Throughout the tenure of the current homeowner many upgrades have been made to this property. Roof, new porch, updated Electrical, kitchen cabinets, Gas furnace, DE leading, new brick chimney. The exterior of the home is being prepped at this time for brand new paint on siding and trim. Buyers must complete the application attached prior to any showings.

22 Arthur St Unit 22, Winchester

Listing courtesy of Listing Agent: Karen Morand from Listing Office: MCO Realty Service, LLC.
8 Hawthorne Road, Winchester
$1,775,000
5 Beds ⋅ 4 Baths ⋅ 73522773 MLS
Welcome to this spacious West Side home w/a versatile multi-level layout, offering ample room for comfortable living and entertaining. In the main level, you'll be greeted by a warm & inviting atmosphere, w/abundant natural light filtering through the windows. You enter a well-appointed kitchen, w/ample counter space, a breakfast nook and a french door access to the deck surrounded by tall trees. The open-concept living and dining area provides a seamless flow, ideal for hosting gatherings or simply relaxing with guests. Family room w/window seat and built-ins, leads to a sunny deck. Next level, you enter an en-suite bedroom and two large additional Bdrms with an updated bath. Two more Bdrms on the upper level can be utilized for a guest or family member w/ultimate flexibility. Lower level, there are Power Rm, Laundry Rm, Dog Spa & Study. This residence provides the ideal blend of functionality and style. Close to Vinson Owen School. This dream home provides easy access to everything!

8 Hawthorne Road, Winchester

Listing courtesy of Listing Agent: H. Elaine Song from Listing Office: Coldwell Banker Realty - Lexington.
2 Everett Ave, Winchester
$3,230,000
7 Beds ⋅ 6 Baths ⋅ 73488991 MLS
Welcome to one of Winchester’s most extraordinary residences. This one-of-a-kind Center Entrance Colonial Revival sits on a beautifully landscaped, private lot complete with in-ground swimming pool and ample outdoor space perfect for relaxation or entertaining. A grand foyer welcomes you in where you can entertain with ease throughout the expansive first floor. Here you will find a high-end eat-in kitchen with large island & granite countertops as well as a formal dining room with gas fireplace. A living room with custom built-ins & window seat, a family room overlooking the yard, and a bar complete this level. This distinguished residence offers 7 bedrooms and 6 bathrooms, blending timeless architectural details with luxurious modern amenities. Additional highlights include a primary suite with walk-in closet and sitting room, large entertainment room, 3 car garage, and close proximity to downtown and commuter rail. Don’t miss this rare opportunity to own a truly remarkable estate.

2 Everett Ave, Winchester

Listing courtesy of Listing Agent: Joan Francis Sullivan from Listing Office: Better Homes and Gardens Real Estate - The Shanahan Group.
18 Grant Road, Winchester
$6,995
4 Beds ⋅ 3 Baths ⋅ 73548131 MLS
Located in a favorite Winchester neighborhood, this spacious and thoughtfully designed home offers an ideal layout for today's lifestyle. The oversized family room flows seamlessly from the kitchen, creating a perfect space for entertaining and everyday living. The kitchen features modern appliances and a slider to the back deck for easy indoor-outdoor enjoyment. A first-floor bedroom or home office, along with a separate laundry room, adds flexibility and convenience. Upstairs, the expansive primary suite includes two walk-in closets, a private bath, and plenty of space for a sitting area. The newly finished expansive lower level provides exceptional bonus space for a family room, playroom, home gym, or media room, plus a dedicated office with its own exterior entrance—ideal for working from home. Enjoy easy winter living with a heated driveway and walkway!

18 Grant Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
59 Wedgemere Avenue, Winchester
$12,000
4 Beds ⋅ 4 Baths ⋅ 73524398 MLS
Beautifully maintained home in one of Winchester’s most desirable family neighborhoods, the Flats..This spacious home full of charm offers generous living spaces, with 4-5 bedrooms, 3 full updated baths, eat in kitchen, freshly painted interior, gleaming hardwood floors, and abundant natural light throughout. The first floor features a large living room, formal dining room, kitchen, family room, and flexible bedroom or office space plus a sunroom. The second floor offers 4 spacious bedrooms including a large 2 room primary suite w dressing area, 2 walk in closets & full updated bath. Additional highlights include a finished lower level with fireplace, brand new carpet offering great recreation space & plenty of storage. You will love the sunny private yard w/ beautiful flowering perennials & trees and a spacious 2-car garage. Ideally located just moments to Winchester Center, train, schools, parks, & everything the town has to offer. A rare rental opportunity in an unbeatable location!

59 Wedgemere Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
18 Graystone Circle Unit 18, Winchester
$1,800,000
3 Beds ⋅ 3 Baths ⋅ 73551306 MLS ⋅ ['Graystone At Winchester'] BLDG.
OFFER ACCEPTED-OH CANCELLED!Discover luxury & convenience in this impeccably maintained 2-3 bed, 2.5-baths unit in desirable Graystone!! A high end townhome community located just outside Winchester center offering a 1st floor primary suite! The gourmet kitchen showcases custom cabinetry, granite countertops, top-of-the-line stainless appliances w/new gas stove. The open-concept living & dining area w/ a gas fireplace, gleaming hardwood floors & soaring cathedral ceilings w/ skylights, leading to a private, deck & yard—perfect for outdoor relaxation. The spacious first-floor primary suite offers a marble bathroom w/ a custom walk-in shower & generous closet space. Upstairs, the spacious second bedroom, full bath plus an oversized loft family room area w/ potential to wall off a portion for 3rd bedroom, & a cozy a den/ office The walkout LL has high ceilings & offers opportunity to finish 1440SF for gym/rec room, media room, storage or anything you desire!

18 Graystone Circle Unit 18, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
52 Middlesex Street Unit 52, Winchester
$1,200,000
4 Beds ⋅ 3 Baths ⋅ 73546076 MLS ⋅ ['50-52 Middlesex St Townhomes'] BLDG.
Newly renovated 4-bedroom, 3-bath townhome offers the privacy and feel of a single-family home in one of Winchester's most desirable neighborhoods. Tucked away on a quiet, tree-lined street just moments from vibrant downtown, this home features its own private entrance, driveway, and backyard. Inside, enjoy new white oak hardwood floors, a stunning chef's kitchen with quartz countertops and full-height quartz backsplash, Bosch stainless steel appliances, and beautifully designed bathrooms with custom tile and premium Kohler fixtures. Additional upgrades include a new roof, new central A/C and heat, recessed lighting, and all-new systems throughout. Winchester is renowned for its award-winning schools, charming New England downtown filled with shops, restaurants, and cafés, easy commuter rail access to Boston, and convenient proximity to major highways—offering the perfect blend of suburban tranquility and city convenience.

52 Middlesex Street Unit 52, Winchester

Listing courtesy of Listing Agent: The North Star Group from Listing Office: Keller Williams Realty Evolution.
16-18 Richardson Unit 16, Winchester
$3,600
3 Beds ⋅ 2 Baths ⋅ 73551302 MLS
3 bedroom 2 bathroom colonial style duplex house in the center of Winchester for rent. Colonial style with spacious living room and kitchen room on the first floor. Second floor master bedroom has an office/exercise room attached. Full basement provides tons of storage spaces. Walking distance to schools, shops, bus stop and commuter rail station. Big backyard provides a great private space for outdoor entertainments. Great opportunity to move into Winchester and take advantage of the great schools, cozy community and close proximity to Boston.

16-18 Richardson Unit 16, Winchester

Listing courtesy of Listing Agent: WINN Rental Team from Listing Office: WINN Real Estate & Consulting.
3 Chesterford Terrace, Winchester
$1,325,000
3 Beds ⋅ 2 Baths ⋅ 73545054 MLS
Nestled at the end of a coveted cul-de-sac, 3 Chesterford Terrace presents a rare opportunity to own a timeless Winchester home on a picture-perfect 12,972 SQ FT flat lot. Designed by renowned Winchester architect Jerome Bailey Foster, this charming 3+ bed, 1.5-bath residence blends classic architectural character with an exceptional setting. Surrounded by mature landscaping & set on one of Winchester's most desirable streets, the home offers endless potential for today's buyer. Enjoy the convenience of being a short stroll to Lynch Elementary School & moments from Winchester's scenic Three Ponds area, where walking trails & outdoor recreation await. Whether you're looking to restore & enhance an architectural gem or create your dream home in an unbeatable location, this property offers a truly special combination of charm & opportunity. Rarely does a home with \setting & potential become available in Winchester. Estate Sale. Sold in as-is condition. Offers due @ noon on 7/14.

3 Chesterford Terrace, Winchester

Listing courtesy of Listing Agent: The Fenway Group from Listing Office: Compass.
14 Rangeley Rdg, Winchester
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 73538612 MLS
Located in the highly desirable Rangeley Estates - a location that puts everyday conveniences close with comfortable living. The main level is designed for everyday living & entertaining with a spacious fireplaced living room with built-in bookcase, separate family room with large closets, dining room opens to deck for easy indoor/outdoor entertaining, kitchen with island seating & stainless steel appliances, bedroom/office, bathroom with shower, & mudroom with storage. Hardwood floors extend throughout most of the first floor. Upstairs offers two bedrooms & full bath, including primary bedroom with skylight, large walk-in closet. Lower level provides valuable bonus space ideal for home office, gym, or playroom, plus laundry area & storage. Conveniently located near schools, shopping, restaurants, local amenities, train, parks, trails & outdoor recreation - this home offers a neighborhood setting with easy access to everything the area has to offer. A must see!

14 Rangeley Rdg, Winchester

Listing courtesy of Listing Agent: Peter Rooney from Listing Office: Compass.
15 Cabot St, Winchester
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 73502658 MLS
Set in one of Winchester’s most coveted neighborhoods, this distinguished Robert Coit-designed residence seamlessly blends timeless architecture with exceptional modern living. Rich in original detail and brimming with character, this 4-bedroom, 2.5-bath home is a true testament to enduring craftsmanship. Gracious living spaces are anchored by three fireplaces, creating warmth and elegance throughout. The expansive kitchen is a showpiece—generous in scale and thoughtfully designed for both everyday living and entertaining. A cypress-paneled den with a fireplace is located on the first floor. The top floor offers 1 room with sink and a large open gallery space, perfect for a home office. Outside, the property unfolds into spectacular, professionally curated gardens and lush landscaping, offering a private oasis that changes beautifully with the seasons. There is a full unfinished basement for additional space. Large welcoming front porch, close to the center and top-rated schools.

15 Cabot St, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
46 Loring Avenue, Winchester
$6,500
4 Beds ⋅ 3 Baths ⋅ 73547715 MLS
Move right into this spacious newer construction home with a great layout, hardwood floors, high ceilings, spacious bedrooms, located near Macdonald Field with playground, tennis etc.. kitchen is fully applianced with gas stove & granite countertop opens into family room w access to rear yard and patio, formal living room and dining room. Direct entry 2 car garage- The oversized primary bedroom offers a walk in closet and full bath w/ soaking tub. Available for a quick movie in!

46 Loring Avenue, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
11 Carriage Lane, Winchester
$1,655,000
4 Beds ⋅ 3 Baths ⋅ 73537920 MLS
15K LOT!! Move right into this beautifully updated 4 BR 3 BA open concept home w/stunning rear addition/primary bedroom suite! This impeccably maintained, nicely updated home has a bright & airy open layout w/ abundant natural light streaming through oversized windows. The main living area flows seamlessly from the spacious living room w/beautiful fireplace into the dining room & kitchen. The recently renovated kitchen includes high end appliances, a center island w/ seating & offers clear views of the back yard. Direct access through slider to oversized deck, patio & huge fenced yard with gorgeous perennials. The main floor bedroom wing offers 3 spacious BR's & 2 baths incl the 2 room primary w/office, spa like bath & walk in closet. LL offers add'l BR suite w/ full BA or family room, laundry & storage. Enjoy hardwood floors, central A/C & spacious 2-car garage. This home is perfect for family enjoyment or hosting large gatherings. Located in a vibrant neighborhood near the swim club

11 Carriage Lane, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
58 Oak St Unit 58, Winchester
$2,750
2 Beds ⋅ 1 Baths ⋅ 73560598 MLS
Don't miss this beautifully updated upper-level apartment at 58 Oak Street, offering two floors of bright, spacious living in one of Winchester's most convenient locations! Combining modern updates with classic charm, this sun-filled home features hardwood floors throughout, high ceilings, central air conditioning, and in-unit laundry for everyday comfort. The spacious eat-in kitchen offers ample cabinet space, gas cooking, and room for casual dining, while generous living areas provide flexible space for relaxing, entertaining, or working from home. Large bedrooms offer excellent closet space, and additional in-unit storage helps keep everything organized. Unwind outdoors on the spacious shared deck, with plenty of room for seating! Available September 1, this unique apartment includes water, trash removal, common area snow removal and a private driveway with parking for up to four cars, and is cat-friendly. Ideally located just moments from Winchester Center, you'll enjoy easy access to the commuter rail, public library, restaurants, cafés, shopping, parks and more. Schedule your showing today!

58 Oak St Unit 58, Winchester

Listing courtesy of Listing Agent: Marika & Associates Group from Listing Office: Hammond Residential Real Estate.
17 Irving Street Unit #3, Winchester
$3,000
3 Beds ⋅ 2 Baths ⋅ 73557638 MLS
Great opportunity to live close to Winchester Center. Available September 1st this 2nd floor unit features a large deck before entering unit. Kitchen has been completely done over new floors, cabinets and all new appliances, living room, bedroom and full bath. Next level, has two bedrooms, bath with shower. All hardwood floors and many windows. Tenant is responsible for Gas, Electric and Cable. First, and Last are due at signing. Basement has designated Washer and Dryer. Close to Winchester Center, Shopping, Restaurants, Schools and Highway Access. Tenant is responsible to get an annual facility permit to bring their trash to the Transfer Station @ 15 McKay Avenue Winchester. The cost is to be paid by Tenant 330 per year.

17 Irving Street Unit #3, Winchester

Listing courtesy of Listing Agent: Robin Griffiths from Listing Office: J. Mulkerin Realty.
171 Swanton St Unit 7, Winchester
$729,000
2 Beds ⋅ 3 Baths ⋅ 73532218 MLS
Easy living awaits at The Village, where this well-maintained, freshly painted, townhouse offers a functional layout, desirable amenities, and a convenient Winchester location. The main level features hardwood floors, an oversized living room with gas fireplace, an open dining area, and kitchen with direct access to a private patio overlooking the beautifully landscaped grounds. A half bath and generous closet space add convenience. Upstairs are 2 bedrooms including a spacious primary suite with walk-in closet and private bath, along with an additional full bath and in-unit laundry. Additional highlights include central air, carport with extra parking, ample storage, fresh interior paint, and custom closet systems. Enjoy access to the community pool, tennis court, clubhouse, and scenic grounds, all just minutes to Winchester Center, commuter rail, shops, restaurants, 2,600 acre Middlesex Fells, and major routes.

171 Swanton St Unit 7, Winchester

Listing courtesy of Listing Agent: Pirani & Wile Group from Listing Office: Gibson Sotheby's International Realty.
50 Brooks Street, Winchester
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 73510897 MLS
Discover this picture perfect 4 BD 3.5 BA colonial in coveted Brooks neighborhood! This distinguished property offers a gourmet kitchen featuring sleek SS appliances, AGA dual fuel range w/ gas burners, center island & tall wine cooler w/sunny brkfst area. The family rm is an architectural focal point, boasting cathedral ceilings, skylights & a cozy fireplace. Natural light floods the home & continues into the formal dining room, breakfast nook, formal living room & home office. The primary suite offers a ensuite bath & large walk in closet. 3 additional bedrooms & a full bath complete the 2nd floor. The finished lower level w/ full bath offers great space for movie nights, kids play space or guest area & gym. This property is complete w/ a 2 car garage & gorgeous level lot. The back yard features an expansive deck, patio & fenced in yard. This home truly has it all! Sought after Brooks neighborhood is close to town, Wedgemere train station & Brooks town forest. Don't miss this one!!

50 Brooks Street, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
282 High Street, Winchester
$10,000
6 Beds ⋅ 5 Baths ⋅ 73484748 MLS
Fabulous 6 month rental opportunity with full additional in-law suite with private kitchen, bedroom, bath, and laundry. Very generous in size and scale.Light filled,modern all brick home abundant in space and comfort.Unrivaled privacy at end of cul-de-sac.Masterfully built staircase presents the two story great room with double sided fireplace.Spacious kitchen with island, double gas range, and 60" of refrigeration. Grand formal dining room,serving pantry,dinette,and fabulous living room make up the first floor common areas. Add a main level bedroom,seperate full and half baths,and large office complete the primary level.Upstairs,open primary suite complete with stone fireplace,ensuite bath,and dressing room.Three additional bedrooms,big full bath,and laundry on second level.Full,finished walkout basement with kitchen,living area,brick oven,fireplace,dinette,and additional 6th bedroom and bathroom ideally suited for in-law,au pair,or multigenerational suite. Come see!!

282 High Street, Winchester

Listing courtesy of Listing Agent: Anthony Marino from Listing Office: The Marino Group Collection.
339-341 Washington Street, Winchester
$980,000
5 Beds ⋅ 2 Baths ⋅ 73534223 MLS
Exceptional opportunity for investors, owner-occupants, or multigenerational living in this two-family home conveniently located near Winchester Center, restaurants, shopping, commuter rail, and major routes. The first floor has 2 bedrooms plus an office, while the second floor includes a third bedroom. Both units are filled with natural light and share nearly identical layouts with enclosed front porches, spacious front-to-back living and dining rooms, original built-in china cabinets, high ceilings, and timeless character throughout. The kitchens offer granite countertops, stainless steel appliances, dedicated pantries, and access to rear porches, while renovated bathrooms and freshly painted interiors add modern appeal. Additional highlights include a 2-car garage, 4 off-street parking spaces, hardwood floors throughout, basement storage, laundry, and an expansive private backyard.

339-341 Washington Street, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
8 Mason Street Unit 8, Winchester
$2,100
1 Beds ⋅ 1 Baths ⋅ 73555538 MLS
Don't let the one-bedroom designation fool you! This spacious two-level apartment offers the flexibility and feel of a much larger home. The thoughtfully designed layout provides generous living space with room to spread out, making it ideal for working from home, entertaining, or simply enjoying separate living areas. Step outside to enjoy shared backyard space—perfect for relaxing or dining outdoors—and the convenience of one off-street parking space and in-unit laundry. Located just moments from the heart of Winchester Center, you'll enjoy easy access to the MBTA Commuter Rail, restaurants, cafés, boutiques, the Town Common, and everyday conveniences. Whether commuting to Boston or enjoying all that Winchester has to offer, this location combines neighborhood charm with exceptional accessibility. A rare opportunity to enjoy generous living space in one of Winchester's most sought-after communities

8 Mason Street Unit 8, Winchester

Listing courtesy of Listing Agent: Melanie Lentini from Listing Office: Leading Edge Real Estate.
186 Ridge Street, Winchester
$15,000
5 Beds ⋅ 5 Baths ⋅ 73510929 MLS
Custom-built ~6,000 sq ft Colonial estate offering 5 bedrooms, 4.5 bathrooms, and panoramic hilltop views on over an acre of beautifully landscaped grounds. Ideally located on the desirable West Side of Winchester, just minutes from Vinson-Owen Elementary School. This impeccably maintained residence features a gourmet chef’s kitchen with high-end appliances, oversized center island, walk-in pantry, and dining area that opens to a spacious family room with a gas fireplace and custom millwork. The main level also includes formal living and dining rooms, a private study, and an oversized mudroom with direct access to the attached three-car garage. The second level offers a luxurious primary suite with a spa-like ensuite bath, three additional bedrooms, a laundry room, and multiple well-appointed bathrooms. The finished walk-up third level serves as an ideal guest retreat or bonus living space, complete with a bedroom, full bathroom, and additional lounge area. The home offers multiple living and dining areas, a fully equipped laundry room, and abundant natural light throughout. Outside, enjoy a private patio overlooking the expansive backyard - perfect for outdoor dining, entertaining, or relaxing. Short- and long-term rentals available. Offered fully furnished or unfurnished.

186 Ridge Street, Winchester

Listing courtesy of Listing Agent: Anzor Sidamonidze from Listing Office: Skylight Real Estate, LLC.
200 Swanton Unit T30, Winchester
$1,800
1 Baths ⋅ 73544352 MLS
A rare opportunity to rent in a prime Winchester location! Desirable private/direct-entry terrace level Studio at the Parkview Condominiums. This updated unit offers convenient walk-out access with a private covered patio perfect for enjoying the outdoors & offers direct views of the duck pond & courtyard gardens. This oversized studio offers ample space for dining, living & bedroom areas! Amenities include a pool for hot summer days and an on-site laundry room. Close to town location with easy access to the grocery store, restaurants, shops & train to Boston. Rent includes all utilities + 1 parking space. No pets. 2 person occupancy maximum.

200 Swanton Unit T30, Winchester

Listing courtesy of Listing Agent: Noha Soliman from Listing Office: Leading Edge Real Estate.
10 Farrow Street, Winchester
$1,660,000
4 Beds ⋅ 4 Baths ⋅ 73538441 MLS
Winchester Single Family Home with Attached Garage. Completely rebuilt in 2019, 4 Bedrooms + 2 Home Offices & 3.5 Bathrooms across 2,750+ SF! Two "WFH Offices" with Door & Window for privacy. Open-Concept Kitchen: Quartz Island/Countertops & Stainless Steel Appliances. Induction cooking & Hood Venting. Open-Concept Flows into the Connected Dining Room & Sundrenched Living Room with Wood Burning Pellet Stove! Charming New England feature provides efficient winter heating bills! Glass Sliding Doors bring you Outside to a Large Deck with custom Motorized Awning. Multiple Zones: Forced Central Air + Heating. Mudroom & Storage! Thoughtful design: First Floor Bedroom Suite, 1BR/1BA. Upstairs 3 Large Bedrooms & Laundry Room. Finished Top Level Offers "Future" Expansion? The Unfinished Attic offers Epic Storage! The BACKYARD: Wowie a Tree House! Swing, Slide, Climbing Wall & 2 Sheds. Prime Location: Quiet street, walking distance to the new Lynch Elementary + Middle school + High school.

10 Farrow Street, Winchester

Listing courtesy of Listing Agent: Collin Bray from Listing Office: Century 21 Cityside.
7-9 Ridge St, Winchester
$1,460,000
5 Beds ⋅ 5 Baths ⋅ 73527738 MLS
Beautiful 2 family-duplex nestled in Winchester's desirable West Side. It tells the story of a home that has been treasured and exceptionally maintained over the years. Rich in warmth offering the kind of enduring quality and care that is increasingly hard to find. It reflects years of thoughtful stewardship with inviting spaces, natural light & flow designed for everyday living. Unit 1 3 beds w/primary suite, office, 2.5 baths, living room, dining room, family room with built-in shelving, eat-in kitchen. Unit 2 2 beds, 1.5 baths, living room, dining room, kitchen, lower level family room. Each unit bodes hardwood floors, in-unit laundry, dedicated basements with high ceilings, driveways, yards with patios. This special home offers flexibility, strong roots & the opportunity to become part of a beloved community. Located in sought after Vinson Owen School within Winchester's top rated school system. Minutes to Winchester Center, 2 MBTA stations direct to Boston & dining!

7-9 Ridge St, Winchester

Listing courtesy of Listing Agent: The Synergy Group from Listing Office: The Synergy Group.
12 Cox Rd, Winchester
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 73511596 MLS
Join me Saturday May 23rd 12-2pm for the 1st Open House at this amazing new price! Fabulous 11 room, 4 bedroom Colonial set on a beautiful lot on Winchester’s west side. The first floor offers a bright and sunny, open concept kitchen and family room which creates the perfect space for everyday living and entertaining and leads to a mud room, laundry, and home office . Completing the first floor is half bath off kitchen, a dining room and a front to back, fireplaced, living room with a peaceful screened in porch that creates a serene escape. An expansive deck that overlooks this magnificent property. Upstairs features a beautiful, new, primary en suite with custom walk- in closet. An additional 3 spacious bedrooms and a new full bath complete the second floor. Lower level includes a playroom, a fireplaced den and extensive storage. Close proximity to Vinson-Owen School, Winchester Swin and Tennis Club and Wright Locke Farm, as well as conservation and many walking trails.

12 Cox Rd, Winchester

Listing courtesy of Listing Agent: Darryl E. Brian from Listing Office: RE/MAX Bentley's.
211 Forest St, Winchester
$2,125,000
5 Beds ⋅ 4 Baths ⋅ 73532996 MLS
Welcomed by a convenient horseshoe driveway surrounded by thoughtfully designed gardens, 211 Forest has undergone a completely reimagined renovation. This curated family residence shows refined attention to detail and a designer’s eye at every turn. From the custom kitchen with bespoke cabinetry and premium hardware, AGA cast-iron range and Liebherr refrigerator to the sunporch filled with natural light, every space reflects intentional design. The living room is anchored by a wood-fired fireplace, while highlights include a 1,000-bottle wine room, home gym, outdoor barrel sauna for daily wellness, whole-house water filtration system with reverse osmosis drinking water, and Sonos surround sound inside and outside. Located in one of Winchester’s most desirable neighborhoods, imagine stepping out your door for a peaceful walk to a trailhead at The Fells or easily biking with your kids to the highly regarded Muraco Elementary School every day.

211 Forest St, Winchester

Listing courtesy of Listing Agent: Michael Gilbert from Listing Office: Stuart St James, Inc..
10 Graystone Cir Unit 10, Winchester
$1,825,000
2 Beds ⋅ 4 Baths ⋅ 73508182 MLS ⋅ ['Graystone At Winchester'] BLDG.
Tucked within the coveted enclave of Graystone, this exceptional townhouse offers a rare blend of scale, privacy, and refined living. Among the largest residences in the community, this impeccably maintained 2-bedroom, 3.5-bath home unfolds across more than 3,800 square feet of thoughtfully designed space. Sunlight pours through expansive windows, illuminating gracious living and entertaining areas that flow seamlessly from room to room. The interiors are polished yet inviting, with generous proportions that allow for both elegant gatherings and comfortable everyday living. The first floor primary suite is large and inviting; another full bedroom suite is on the second floor, along with an expansive office and a cozy den. A rare walk-out patio on the lower level opens directly to a serene, forested backdrop—an uncommon offering that creates a private retreat, perfect for morning coffee or evening relaxation surrounded by nature.

10 Graystone Cir Unit 10, Winchester

Listing courtesy of Listing Agent: The Pallotta Group from Listing Office: Gibson Sotheby's International Realty.
34 Glen Road, Winchester
$11,000
7 Beds ⋅ 4 Baths ⋅ 73501557 MLS
TOP location! Beautifully renovated single family colonial in Ambrose elementary district, situated on a gorgeous lot with oversized new 2 car garage, This 6-7 bedroom 3.5 bath home has been tastefully updated & redesigned offering desirable open concept living w/ central air & all new systems. This home features a welcoming front porch, spacious foyer, beautiful custom chefs kitchen w/ professional/Thermador appliances, spacious dining room, double living room w/ fireplace, custom built ins, high ceilings & gas fireplace. Family room with sliders to large deck and great level yard, perfect for family enjoyment. The second floor offers 4 bedrooms, including a spacious primary w/ full bath & oversized tile shower plus 3 additional bedrooms one (smaller) great for a home office. The full third floor is spacious & bright and offers 3 additional large bedrooms plus another full bath.

34 Glen Road, Winchester

Listing courtesy of Listing Agent: Kim Covino & Co. Team from Listing Office: Compass.
33 Nelson St, Winchester
$3,800
2 Beds ⋅ 2 Baths ⋅ 73534980 MLS
Wonderful single family home for rent! Located in nice quiet neighborhood close by acclaimed Winchester High School. House is certified lead paint compliant! Walking distance to train, shops and restaurants in beautiful downtown Winchester. Recently updated kitchen and baths. Granite counters and stainless steel appliances. New windows, gas heating and new central air conditioning make for energy efficient living! Second-story washer/dryer. Private backyard with patio; perfect for summertime dinners with family and friends! Available August 1st. Come see this fantastic home today!

33 Nelson St, Winchester

Listing courtesy of Listing Agent: Russell Hulteen from Listing Office: Coldwell Banker Realty - Lexington.
54 Spruce Street, Winchester
$8,000
5 Beds ⋅ 4 Baths ⋅ 73500087 MLS
Well maintained 5 bedroom, 3.5-bath single-family home built in 2004, ideally located within walking distance to the town center, schools, shopping, and the commuter rail. This spacious home features hardwood floors, central AC, and a thoughtfully designed layout perfect for everyday living and entertaining. The bright kitchen flows into generous living and dining spaces, while the finished basement provides additional room for recreation, a home office, or gym. A two-car garage offers convenience and storage. Enjoy a prime location combined with modern comforts perfect for today’s lifestyle. Available July 2026

54 Spruce Street, Winchester

Listing courtesy of Listing Agent: Dylan Archambault from Listing Office: The Archambault Group.

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

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