Winchester, MA Homes

/36
$1,175,000 Sold Aug 18, 2025
- 2,335 Sq Ft
- $503/SF
- 8 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1961
163 Main St, Winchester, MA 01890

Charming multi-level home in close proximity to Winchester Center, public transit, Lincoln Elementary, and McCall. The main level offers an open floor plan with beautiful hardwood floors, bay windows, a skylit eat-in kitchen, and abundant natural light. Perfect for entertaining, the living and dining rooms flow seamlessly to a spacious yard, relaxing patio, and mature gardens. The top floor

Andersen Group Realty Keller Williams Realty Boston Northwest

163 Main St, Winchester, MA 01890

/37
Est $2,234,992 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 4,209 Sq Ft
4 Mayflower Rd, Winchester, MA 01890

4 Mayflower Rd, Winchester, MA 01890

/31
$1,399,000 Pending
- 4 Beds
- 2.5 Baths
- 2,865 Sq Ft
4 Sargent Rd, Winchester, MA 01890

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,

Monte Marrocco Coldwell Banker Realty - Lexington

4 Sargent Rd, Winchester, MA 01890
/30
$640,000 Sold Aug 15, 2025
- 1,464 Sq Ft
- $437/SF
- 8 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1976
60 Lake St Unit I, Winchester, MA 01890

Enjoy the best of Winchester living in this spacious 2-bed, 1.5-bath townhouse at Wedge Pond Condominium, set along scenic Wedge Pond. The main level features hardwood floors, a sunny living room, dining room with charming bow window, half bath, and renovated kitchen with updated appliances. Upstairs offers two bedrooms and a full bath. The finished lower level provides flexible space for a

Pirani & Wile Group Gibson Sotheby's International Realty

60 Lake St Unit I, Winchester, MA 01890

/42
Est $2,064,118 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,770 Sq Ft
7 Plymouth Rd, Winchester, MA 01890

7 Plymouth Rd, Winchester, MA 01890

/41
$1,150,000 Pending
- 5 Beds
- 2 Baths
- 2,610 Sq Ft
415-417 Washington St, Winchester, MA 01890

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

Paula Sughrue Better Homes and Gardens Real Estate - The Shanahan Group

415-417 Washington St, Winchester, MA 01890
/41
$790,001 Sold Aug 15, 2025
- 1,441 Sq Ft
- $548/SF
- 12 Days On Market
- 3 Beds
- 2 Baths
- Built 1901
9 Emerson Ct, Winchester, MA 01890

Looking for the ideal first home or a peaceful place to settle into your next chapter? This charming 3-bedroom, 2-bath home, nestled at the end of a quiet dead-end street, was completely remodeled in 2009. Step inside to a warm and welcoming space with a practical layout—everything you need without the fuss. Whether you're just getting started or looking to simplify, this move-in-ready home is a

Rodrigo Serrano Leading Edge Real Estate

9 Emerson Ct, Winchester, MA 01890

/42
Est $3,086,403 Not Listed For Sale
- 5 Beds
- 5.5 Baths
- 5,600 Sq Ft
6 Pocahontas Dr, Winchester, MA 01890

6 Pocahontas Dr, Winchester, MA 01890

/16
$995,000 Pending
- 4 Beds
- 3 Baths
- 1,860 Sq Ft
60 Harvard St, Winchester, MA 01890

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

Mark Krasnyansky eXp Realty

60 Harvard St, Winchester, MA 01890
/42
$1,775,000 Sold Aug 15, 2025
- 3,150 Sq Ft
- $563/SF
- 6 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1961
19 Pilgrim Dr, Winchester, MA 01890

Your very own private oasis tucked away in a cul-de-sac-like neighborhood just mins. to Winchester Center! Set on a deep, tree-lined lot, this stunning home offers 5 beds, 3.5 baths, & over 3,000 sq. ft. The versatile floor plan offers ground-level entry w/ a 2 car garage, 2 bedrooms (which can also function as work/play space,) & full bath/laundry area. The upper level is the heart of the home –

Gorfinkle Group eXp Realty

19 Pilgrim Dr, Winchester, MA 01890

/36
Est $1,669,367 Not Listed For Sale
- 4 Beds
- 3 Baths
- 4,190 Sq Ft
43 Mayflower Rd, Winchester, MA 01890

43 Mayflower Rd, Winchester, MA 01890

/40
$2,250,000 Pending
- 6 Beds
- 5 Baths
- 3,728 Sq Ft
6 Ivy Cir, Winchester, MA 01890

Spacious newly gut renovated colonial set back on a cul-de-sac! Unbeatable location in quiet neighborhood less than a mile from all Winchester's amazing public schools and Wedge Pond. Hardwood floors throughout with gorgeous kitchen featuring huge island, large living and dining rooms. A vaulted family room with authentic barn board detailing sits adjacent to the kitchen, opening to a large

Rose Hall Blue Ocean Realty, LLC

6 Ivy Cir, Winchester, MA 01890
/42
$2,890,000 Sold Aug 14, 2025
- 5,386 Sq Ft
- $537/SF
- 9 Days On Market
- 5 Beds
- 4.5 Baths
- Built 1963
21 Fernway, Winchester, MA 01890

Exceptional colonial on Myopia Hill showcasing an expansive rear family room addition, perfectly situated on an idyllic lot surrounded by lush gardens & mature landscape. This stately residence offers a true private oasis just minutes from all conveniences. Rich in finish, elegant in design w/ stunning living areas, large scale rooms & 4 fireplaces creating warm inviting spaces for every day

Kim Covino Compass

21 Fernway, Winchester, MA 01890

/35
Est $2,139,616 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,439 Sq Ft
34 Mayflower Rd, Winchester, MA 01890

34 Mayflower Rd, Winchester, MA 01890

/42
$2,190,000 Pending
- 6 Beds
- 4 Baths
- 4,385 Sq Ft
5 Bacon St, Winchester, MA 01890

This stunning Victorian home, in the style of Painted Ladies w/ soaring ceilings & hardwood floors, is in a prime neighborhood just moments from Winchester Center, the commuter rail, Shannon Beach, & a short ride to the Airport & Boston. The house lives as a harmonious single family with a second kitchen on the 1st floor (multigenerational living potential). It has 6 beds & 4 baths, over 4,385 SF

Anne Spry Barrett Sotheby's International Realty

5 Bacon St, Winchester, MA 01890
/40
$2,175,000 Sold Aug 14, 2025
- 4,667 Sq Ft
- $466/SF
- 18 Days On Market
- 6 Beds
- 3.5 Baths
- Built 1895
9 Prospect St, Winchester, MA 01890

Step into timeless elegance with this Colonial Revival, a true celebration of classic architecture, refined style, and exceptional craftsmanship. From the moment you arrive, the home's rich character makes a striking first impression, setting the stage for everything that follows. Inside, you’ll discover a harmonious blend of historic charm and modern comfort. Gleaming hardwood floors, intricate

Nancy Pallotta Gibson Sotheby's International Realty

9 Prospect St, Winchester, MA 01890

/40
Est $1,533,502 Not Listed For Sale
- 2 Beds
- 3 Baths
- 2,874 Sq Ft
57 Hutchinson Rd, Winchester, MA 01890

57 Hutchinson Rd, Winchester, MA 01890

/36
$1,299,900 Pending
- 5 Beds
- 2 Baths
- 1,706 Sq Ft
35 Harvard St, Winchester, MA 01890

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

Joanne Mulkerin J. Mulkerin Realty

35 Harvard St, Winchester, MA 01890
/40
$1,160,000 Sold Aug 14, 2025
- 2,302 Sq Ft
- $504/SF
- 22 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1915
518 Washington St, Winchester, MA 01890

Set in the coveted Muraco School District, this classic 1915 Colonial offers the perfect blend of character and modern comfort. Featuring 4 bedrooms and 2.5 baths, the welcoming main level boasts an open-concept layout with an eat-in kitchen (granite countertops, stainless steel appliances), a dining room with charming built-ins, a spacious living room, and a convenient powder room with laundry.

Rodrigo Serrano Leading Edge Real Estate

518 Washington St, Winchester, MA 01890

/33
Est $1,350,612 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,636 Sq Ft
132 Cambridge St, Winchester, MA 01890

132 Cambridge St, Winchester, MA 01890

/42
$397,000 Pending
- 1 Bed
- 1 Bath
- 634 Sq Ft
200 Swanton St Unit T11, Winchester, MA 01890

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

Shannon Jenkins RE/MAX Realty Experts

200 Swanton St Unit T11, Winchester, MA 01890
/42
$2,215,000 Sold Aug 12, 2025
- 3,607 Sq Ft
- $614/SF
- 5 Days On Market
- 5 Beds
- 3.5 Baths
- Built 1895
4 Winslow Rd, Winchester, MA 01890

Situated in a coveted Winchester neighborhood, this classical five-bedroom home unfolds across 3 levels above grade—boasting sunlit living & dining spaces framed by walls of windows overlooking lush greenery, a chef’s kitchen appointed with an expansive butcher-block island & dual fuel oven & a serene primary suite featuring a private bath & walk-in closet. 2 additional bedrooms occupy the second

Anne Spry Barrett Sotheby's International Realty

4 Winslow Rd, Winchester, MA 01890

/42
Est $2,392,174 Not Listed For Sale
- 5 Beds
- 7 Baths
- 7,292 Sq Ft
7 Russett Ln, Winchester, MA 01890

7 Russett Ln, Winchester, MA 01890

/17
$999,000 Pending
- 3 Beds
- 1.5 Baths
- 1,683 Sq Ft
41 Englewood Rd, Winchester, MA 01890

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

Lesley Smith Barrett Sotheby's International Realty

41 Englewood Rd, Winchester, MA 01890
/6
$1,120,000 Sold Aug 11, 2025
- 2,060 Sq Ft
- $544/SF
- 2 Days On Market
- 4 Beds
- 2 Baths
- Built 1917
540-542 Washington St, Winchester, MA 01890

Great Two-Family Home in a Desirable Location! This well-maintained two-family property features a total of 4 bedrooms and 2 full bathrooms, with beautiful hardwood floors throughout. Each unit offers spacious living areas filled with natural light. The basement includes laundry hookups with washer and dryer included. Enjoy the convenience of 6 off-street parking spaces—a rare find! Situated just

Wei Wang WW Real Estate LLC

540-542 Washington St, Winchester, MA 01890

/42
Est $2,257,037 Not Listed For Sale
- 6 Beds
- 5.5 Baths
- 5,800 Sq Ft
8 Johnson Rd, Winchester, MA 01890

8 Johnson Rd, Winchester, MA 01890

/33
$1,399,000 Pending
- 3 Beds
- 4.5 Baths
- 2,722 Sq Ft
6 Wyman Ct Unit 6, Winchester, MA 01890

Another Tree Top Group masterpiece –Welcome to 6 Wyman Court! New full gut renovation townhome with 2,722 sq. ft., 3 beds, 4.5 baths & 4 levels of sun-drenched living space. Located in a prime end of cul-de-sac & moments from the vibrant Winchester Center including shops, dining & commuter rail. Main level features a thoughtfully designed kitchen w/ stainless steel appliances, a large center

Monte Marrocco Coldwell Banker Realty - Lexington

6 Wyman Ct Unit 6, Winchester, MA 01890
/37
$770,000 Sold Aug 11, 2025
- 1,123 Sq Ft
- $686/SF
- 44 Days On Market
- 2 Beds
- 1 Bath
- Built 1986
22 Grove Place Unit 4, Winchester, MA 01890

Looking to downsize or just live more modestly?Welcome to the sought-after White Horse Commons Condominiums, The perfect opportunity to enjoy the lovely town of Winchester and keep costs down. Near Symmes corner, downtown Winchester & Wedgemere train station, this wonderful 2 bedroom, 1 bathroom end unit lives and feels like a single home with windows on all three sides. The kitchen offers a

Kim Covino Compass

22 Grove Place Unit 4, Winchester, MA 01890

/40
Est $2,923,443 Not Listed For Sale
- 4 Beds
- 5 Baths
- 4,051 Sq Ft
50 Emerson Rd, Winchester, MA 01890

50 Emerson Rd, Winchester, MA 01890

/23
$999,999 Pending
- 3 Beds
- 2 Baths
- 1,535 Sq Ft
16 Park Ave Unit 1, Winchester, MA 01890

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 Cafe range and microwave, an oversized sink, and large peninsula with ample seating flows seamlessly to the

Andrea Mackey Barrett Sotheby's International Realty

16 Park Ave Unit 1, Winchester, MA 01890
/42
$3,745,000 Sold Aug 08, 2025
- 7,587 Sq Ft
- $494/SF
- 44 Days On Market
- 7 Beds
- 8 Baths
- Built 2010
25 Wedgemere Ave, Winchester, MA 01890

Stately elegance resides on one of the most desirable streets in the “Flats". This sprawling home details fine craftsmanship & modern finishes that a home of this caliber warrants. Sprawling open concept kitchen w/ impressive coffered ceilings, eat-in dining along w/ an adjoining family rm w/gas fireplace, dining room, and a formal living room make this the perfect space for entertaining. 7

Prestige Homes Realty Team Prestige Homes Real Estate, LLC

25 Wedgemere Ave, Winchester, MA 01890

/37
Est $1,910,670 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 3,689 Sq Ft
36 Robinhood Rd, Winchester, MA 01890

36 Robinhood Rd, Winchester, MA 01890

/42
$2,995,000 Pending
- 6 Beds
- 6.5 Baths
- 8,463 Sq Ft
26 Swan Rd, Winchester, MA 01890

*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

Kim Covino Compass

26 Swan Rd, Winchester, MA 01890
/37
$1,000,000 Sold Aug 01, 2025
- 1,977 Sq Ft
- $506/SF
- 5 Days On Market
- 3 Beds
- 2 Baths
- Built 1963
26 Olive St, Winchester, MA 01890

Don't miss this rare opportunity to own a charming home with an expansive yard on a quiet cul-de-sac street! This lovely 3-bedroom ranch is meticulously maintained and situated in the sought-after Muraco school district. The main floor features an eat-in kitchen, formal dining room, and a sun-filled living room with a fireplace, perfect for relaxing or entertaining. Gleaming hardwood floors run

Andersen Group Realty Keller Williams Realty Boston Northwest

26 Olive St, Winchester, MA 01890

/42
Est $1,754,077 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,635 Sq Ft
9 Blossom Hill Rd, Winchester, MA 01890

9 Blossom Hill Rd, Winchester, MA 01890

/39
$2,695,000 Pending
- 5 Beds
- 3.5 Baths
- 4,779 Sq Ft
48 Salisbury St, Winchester, MA 01890

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,

Katie Tully Better Homes and Gardens Real Estate - The Shanahan Group

48 Salisbury St, Winchester, MA 01890
/38
$1,627,000 Sold Jul 31, 2025
- 2,853 Sq Ft
- $570/SF
- 7 Days On Market
- 5 Beds
- 4 Baths
- Built 1930
32 Oneida Rd, Winchester, MA 01890

Move right into this 5 b/r 4 bth colonial steps to Ambrose School! This picture perfect colonial features high ceilings,hdwd floors & an open first floor plan that creates an airy, welcoming atmosphere.The bright kitchen equipped with ss appliances & charming banquette seating is perfect for casual family meals; step outside to the deck overlooking the spacious yard or into the beautiful

Stephanie McGowan Better Homes and Gardens Real Estate - The Shanahan Group

32 Oneida Rd, Winchester, MA 01890

/37
Est $1,467,963 Not Listed For Sale
- 5 Beds
- 2.5 Baths
- 2,793 Sq Ft
4 Albamont Rd, Winchester, MA 01890

4 Albamont Rd, Winchester, MA 01890

/27
$1,075,000 Pending
- 2 Beds
- 2 Baths
- 1,531 Sq Ft
10 Winchester Place Unit 301, Winchester, MA 01890

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

Anne Spry Barrett Sotheby's International Realty

10 Winchester Place Unit 301, Winchester, MA 01890
/41
$2,425,000 Sold Jul 31, 2025
- 5,501 Sq Ft
- $441/SF
- 61 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2025
15 Churchill Rd, Winchester, MA 01890

Indulge in modern luxury with this stunning home, set on a double 1/2 acre lot. This 4 bedroom, 4.5-bathroom home seamlessly blends chic style with an abundance of functional space. The architectural design is dramatic, showcasing soaring ceilings, a stunning contemporary fireplace, state of the art kitchen & sun filled living room which opens to a fabulous deck, creating a perfect indoor-outdoor

Kim Covino Compass

15 Churchill Rd, Winchester, MA 01890

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Massachusetts Middlesex County Winchester

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