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Explore Similar Homes Within 2 Miles of Winchester Highlands, MA

  • 159 Main St Unit 39A, Stoneham, MA 02180
    159 Main St Unit 39A, Stoneham, MA 02180
    159 Main St Unit 39A, Stoneham, MA 02180
    /41

    $448,800

    • 2 Beds
    • 2 Baths
    • 1,010 Sq Ft

    159 Main St Unit 39A, Stoneham, MA 02180

    NEW LOW PRICE! Beautiful move-in ready, Sun-drenched 2 BR / 2 bath corner condo in desirable Monterosa complex with its pool! Afternoon sun fills the open concept living space & glistens off the HW floors including in the BRs.Recently updated kitchen with granite countertops and high-end Bosch appliances. 4th floor condo with balcony overlocks the back (quiet side) of the bldg. 2 elevators

    Agent Photo

    Steven Mango

    StartPoint Realty

    (781) 488-5181

    159 Main St Unit 39A, Stoneham, MA 02180
  • 200 Swanton St Unit T28, Winchester, MA 01890
    200 Swanton St Unit T28, Winchester, MA 01890
    200 Swanton St Unit T28, Winchester, MA 01890
    /34

    $380,000

    • 1 Bed
    • 1 Bath
    • 634 Sq Ft

    200 Swanton St Unit T28, Winchester, MA 01890

    Beautiful terrace-level 1-bedroom condo in Winchester! This garden-level unit offers tranquil pond views and direct patio access just outside the pond. The condo features a bright, open layout with large windows bringing in natural light. HOA fee includes heat, hot water, electricity, and air conditioning—making it easy and affordable to maintain. Enjoy a peaceful setting with access to the

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (781) 384-5553

    200 Swanton St Unit T28, Winchester, MA 01890
  • 200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    200 Swanton St Unit 228, Winchester, MA 01890
    /14

    $399,000

    • 1 Bed
    • 1 Bath
    • 606 Sq Ft

    200 Swanton St Unit 228, Winchester, MA 01890

    Beautifully maintained and freshly painted 1-bedroom condo at Parkview Condominiums in Winchester. This bright unit features an open layout with peaceful views overlooking the pond. The low HOA fee includes heat, hot water, electricity, and air conditioning—an exceptional value. Highlights include a spacious living area, updated kitchen with new stainless steel appliances, a large bedroom with

    Agent Photo

    Joan Powell

    RE/MAX Andrew Realty Services

    (781) 417-5122

    200 Swanton St Unit 228, Winchester, MA 01890
  • 31 Arlington Rd Unit 6, Woburn, MA 01801
    31 Arlington Rd Unit 6, Woburn, MA 01801
    31 Arlington Rd Unit 6, Woburn, MA 01801
    /26

    $405,000

    • 2 Beds
    • 1 Bath
    • 856 Sq Ft

    31 Arlington Rd Unit 6, Woburn, MA 01801

    Welcome to this beautifully updated top-floor unit (3rd floor- walk up) at the highly sought-after Ambassador Manor! This sun-filled 2-bedroom, 1-bath condo offers a perfect blend of comfort, convenience, and style.Step inside to find a spacious open-concept living and kitchen area, ideal for entertaining or relaxing at home. The modern kitchen is with sleek cabinetry and updated lighting.

    Agent Photo

    Jay Liu

    Jiang Hua Liu

    (339) 331-1336

    31 Arlington Rd Unit 6, Woburn, MA 01801
  • 48 Tremont St, Malden, MA 02148
    48 Tremont St, Malden, MA 02148
    48 Tremont St, Malden, MA 02148
    /6

    $2,400,000

    • 7 Beds
    • 9 Baths
    • 5,888 Sq Ft

    48 Tremont St, Malden, MA 02148

    Location, Location, Location!! Exceptional - 9 family apartment building. Great investment opportunity. On the bus line. Close to downtown Malden. Less than one mile from Malden Center T Station - the orange line. Complex consists of two studios, five one bedrooms and two one bedroom plus office room. Large parking lot with three garages.

    Agent Photo

    Maria DiPierro

    Atlantic Realty Services

    (339) 674-6505

    48 Tremont St, Malden, MA 02148
  • 477 Main St, Woburn, MA 01801
    477 Main St, Woburn, MA 01801
    /2

    $779,000

    • Land
    • 0.09 Acre
    • $8,655,556 per Acre

    477 Main St, Woburn, MA 01801

    Approved 7 unit development in the heart of downtown Woburn. Luxury, mixed use building, with loft style residential units sitting on top of a prime retail location. Inquire for more details.

    Agent Photo

    Paul Connolly

    1M Realty LLC

    (339) 229-6455

    477 Main St, Woburn, MA 01801
  • 124 Grant Ave, Medford, MA 02155
    124 Grant Ave, Medford, MA 02155
    124 Grant Ave, Medford, MA 02155
    /41

    $1,495,000

    • 6 Beds
    • 3 Baths
    • 3,203 Sq Ft

    124 Grant Ave, Medford, MA 02155

    Incredible opportunity to own a well-maintained three-family in a prime Medford location minutes from Tufts, Medford Square, and the Green Line Extension. Perfect for investors or owner-occupants, this property offers immediate cash flow and long-term upside. The first-floor unit has been fully renovated with two bedrooms, one bath, and an open layout. The second-floor unit mirrors the first and

    Agent Photo

    Hans Nagrath

    Compass

    (339) 201-9537

    124 Grant Ave, Medford, MA 02155
  • 62 Foundry St Unit 204, Wakefield, MA 01880
    62 Foundry St Unit 204, Wakefield, MA 01880
    62 Foundry St Unit 204, Wakefield, MA 01880
    /35

    $499,999

    • 1 Bed
    • 1 Bath
    • 796 Sq Ft

    62 Foundry St Unit 204, Wakefield, MA 01880

    New construction at The Wrenly. Completed in 2024, this residence offers refined single-level living in the center of Wakefield. The open-concept floor plan is anchored by a kitchen featuring a quartz island and stainless steel appliances, flowing into living spaces detailed with engineered hardwood and smart home integration. The layout includes a spacious bedroom, a tiled bath, and a French

    Agent Photo

    North Shore and More Team

    eXp Realty

    (339) 330-4695

    62 Foundry St Unit 204, Wakefield, MA 01880
  • 37-39 Park St, Malden, MA 02148
    37-39 Park St, Malden, MA 02148
    37-39 Park St, Malden, MA 02148
    /34

    $1,680,000

    • 4 Beds
    • 4 Baths
    • 3,381 Sq Ft

    37-39 Park St, Malden, MA 02148

    NEWLY RENOVATED DUPLEX IN DESIRABLE MALDEN LOCATION!! Location! Location! Beautiful, large newly renovated duplex (2 side-by-side units) close to Malden Center T and steps away from Malden High School! Located on a quiet one-way street! Each unit features 8 rooms, 4 generously-sized bedrooms, and 4 full bathrooms spanning 3 levels of living space. 1st floors features a beautiful, modern kitchen

    Derek Wong V & E Realty

    37-39 Park St, Malden, MA 02148
  • 19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    19 Town Way, Winchester, MA 01890
    /42

    $2,899,000

    • 5 Beds
    • 5.5 Baths
    • 5,257 Sq Ft

    19 Town Way, Winchester, MA 01890

    Welcome to a stunning new-construction home in Winchester’s coveted Lincoln Elementary district, where thoughtful design and refined style come together effortlessly. Every detail has been curated to create a warm, inviting vibe, from the gorgeous family room with custom walnut built-ins and artful lighting to the seamless flow of the open yet intentionally defined floor plan. The impressive

    Philip Vita Compass

    19 Town Way, Winchester, MA 01890
  • 10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    10 Viking Rd, Winchester, MA 01890
    /42

    $2,595,000

    • 4 Beds
    • 4 Baths
    • 5,674 Sq Ft

    10 Viking Rd, Winchester, MA 01890

    Experience the perfect blend of craftsmanship & modern luxury in this stunning custom-built brick ranch. From the moment you enter the spacious front foyer, you’re greeted by soaring cathedral beamed ceilings & an inviting open-concept layout that seamlessly connects the living, dining, & family areas—ideal for effortless entertaining & comfort. A thoughtfully designed private wing includes 4

    Anne Spry Barrett Sotheby's International Realty

    10 Viking Rd, Winchester, MA 01890
  • 601 Franklin St Unit 2, Melrose, MA 02176
    601 Franklin St Unit 2, Melrose, MA 02176
    601 Franklin St Unit 2, Melrose, MA 02176
    /25

    $525,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 1 Bath
    • 1,330 Sq Ft

    601 Franklin St Unit 2, Melrose, MA 02176

    Located in Melrose Highlights! 0.2 miles to the commuter rail. This condo lives like a single-family home in the heart of Melrose. Discover the perfect balance of privacy & convenience in this beautifully designed end-unit condo that truly lives like a single-family home—without the upkeep. Open layout featuring coffered ceilings, in-unit laundry, abundant natural light, & custom finishes

    Joanne Rodrigues Redfin Corp.

    601 Franklin St Unit 2, Melrose, MA 02176
  • 1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    1 Town Way, Winchester, MA 01890
    /40

    $1,899,000

    • 3 Beds
    • 3.5 Baths
    • 3,010 Sq Ft

    1 Town Way, Winchester, MA 01890

    Welcome home to this completely renovated gem, ideally situated on a corner lot in the highly sought-after Lincoln Elementary School district. Warm, inviting, and truly move-in ready, this home offers the open-concept first floor buyers dream of—featuring a beautiful kitchen flowing seamlessly into the dining and living areas, plus a sunken family room perfect for relaxing or entertaining. Enjoy

    Philip Vita Compass

    1 Town Way, Winchester, MA 01890
  • 69 Foundry St Unit 310, Wakefield, MA 01880
    69 Foundry St Unit 310, Wakefield, MA 01880
    69 Foundry St Unit 310, Wakefield, MA 01880
    /27

    $645,000

    • 2 Beds
    • 2 Baths
    • 1,009 Sq Ft

    69 Foundry St Unit 310, Wakefield, MA 01880

    Welcome to The Foundry! This stunning 2bedroom, 2bath residence offers over 1,000 sq ft of single-level living & has been meticulously maintained. Conveniently located just off the elevator, this home combines high-end finishes, thoughtful design, & everyday convenience. The designer kitchen features granite countertops, ss appliances, custom cabinetry, & a breakfast bar, opening to a bright,

    Margi Shah Redfin Corp.

    69 Foundry St Unit 310, Wakefield, MA 01880
  • 545 Winthrop St Unit Lot 6, Medford, MA 02155
    545 Winthrop St Unit Lot 6, Medford, MA 02155
    545 Winthrop St Unit Lot 6, Medford, MA 02155
    /26

    $1,799,900

    • 4 Beds
    • 4.5 Baths
    • 3,700 Sq Ft

    545 Winthrop St Unit Lot 6, Medford, MA 02155

    60% SOLD OUT! Introducing The Mary Kenney Collection: 10 new single-family homes in a private cul-de-sac on the Winchester line. Secure your lot now and enjoy the rare ability to customize floor plans and finishes to fit your lifestyle. Each home offers an oversized 2-car garage, grand foyer & flex space perfect for a gym, theatre, or guest suite. The open-concept main level is designed for

    The Legacy Group EVO Real Estate Group, LLC

    545 Winthrop St Unit Lot 6, Medford, MA 02155
  • 15 Higgins St Unit 17, Arlington, MA 02476
    15 Higgins St Unit 17, Arlington, MA 02476
    15 Higgins St Unit 17, Arlington, MA 02476
    /41

    $1,095,000

    • 3 Beds
    • 2.5 Baths
    • 1,821 Sq Ft

    15 Higgins St Unit 17, Arlington, MA 02476

    Welcome to 15 Higgins Street, Unit 15 Arlington.This beautifully designed 3-bedroom, 2.5-bath condo offering a perfect blend of comfort and style.The main level features an open layout,abundance of natural light a spacious kitchen showcasing an oversized peninsula island with microwave drawer,Bertazzoni stove with direct vent range hood, abundant cabinetry,sleek quartz countertops overlooking the

    Skambas Realty Group Compass

    15 Higgins St Unit 17, Arlington, MA 02476
  • 1025 Massachusetts Ave Unit 204, Arlington, MA 02476
    1025 Massachusetts Ave Unit 204, Arlington, MA 02476
    1025 Massachusetts Ave Unit 204, Arlington, MA 02476
    /29

    $899,900 Open Thu 11AM - 2PM

    • 1 Bed
    • 1 Bath
    • 1,058 Sq Ft

    1025 Massachusetts Ave Unit 204, Arlington, MA 02476

    OPEN HOUSE Th/Fri/Sat 11-2pm. One of the only two remaining 1 bedroom residences with a private patio at Majestic Mill Brook, a luxury new construction condo complex built by The Maggiore Companies. Low-emissions development with high-quality finishes and contemporary flair. The stylish interiors feature an open concept living room, dining room, and kitchen with electric range, exterior vented

    Paul Cirignano The Synergy Group

    1025 Massachusetts Ave Unit 204, Arlington, MA 02476
  • 62 Foundry St Unit 310, Wakefield, MA 01880
    62 Foundry St Unit 310, Wakefield, MA 01880
    62 Foundry St Unit 310, Wakefield, MA 01880
    /36

    $869,900

    • 2 Beds
    • 2 Baths
    • 1,406 Sq Ft

    62 Foundry St Unit 310, Wakefield, MA 01880

    Largest 2 bed left in the building! Experience refined living at the AWARD WINNING Wrenly Residences - Where Luxury Meets Lifestyle. This elegant 2-bedroom plus office, 2-bathroom condo spans over 1,400 square feet all on one level, featuring engineered hardwood floors and a designer kitchen with top-of-the-line appliances. The spacious primary suite includes ample closet space and a luxurious

    Aranson Maguire Group Compass

    62 Foundry St Unit 310, Wakefield, MA 01880
  • 62 High St Unit Lot 8, Stoneham, MA 02180
    62 High St Unit Lot 8, Stoneham, MA 02180
    62 High St Unit Lot 8, Stoneham, MA 02180
    /17

    $1,549,900

    • 4 Beds
    • 2.5 Baths
    • 2,515 Sq Ft

    62 High St Unit Lot 8, Stoneham, MA 02180

    Only 5 homes left at Stoneham Heights! Stoneham’s newest and most prestigious neighborhood. Discover Stoneham Heights, an exclusive collection of 13 newly constructed, architect-designed, single-family residences. Crafted by a local builder with high-quality materials, these homes offer modern design and open floor plans for today’s lifestyle. Exceptional features include gourmet kitchens,

    Erin Anderson Anderson Realty Partners

    62 High St Unit Lot 8, Stoneham, MA 02180
  • 115 Emerald St, Medford, MA 02155
    115 Emerald St, Medford, MA 02155
    115 Emerald St, Medford, MA 02155
    /41

    $1,150,000

    • 4 Beds
    • 4 Baths
    • 2,150 Sq Ft

    115 Emerald St, Medford, MA 02155

    Welcome to 115 Emerald St. This beautifully designed gut renovated 4 bed 4 bath unit is a must see! As you walk into the unit the grandeur of the property just takes your breath away. The main level open concept living space just pops with elegance. The quality of workmanship & materials are noticed from the get-go. From the sleek fireplace to the spacious kitchen island this property just speaks

    Alex Genovese Flow Realty, Inc.

    115 Emerald St, Medford, MA 02155
  • 137 Franklin St Unit 102, Stoneham, MA 02180
    137 Franklin St Unit 102, Stoneham, MA 02180
    137 Franklin St Unit 102, Stoneham, MA 02180
    /25

    $424,900

    • 2 Beds
    • 2 Baths
    • 921 Sq Ft

    137 Franklin St Unit 102, Stoneham, MA 02180

    Welcome to this charming beautiful condo in Stoneham! This unit features an updated kitchen with adjacent dining room perfect for preparing and enjoying delicious meals. The living room has a slider to your private outdoor space for your morning coffee or evening wine. The primary bedroom has a walk-in closet and full bath, while the second bedroom has a bonus closet (2 closets). So many great

    Debi Malone LAER Realty Partners

    137 Franklin St Unit 102, Stoneham, MA 02180
  • 8 Ralph St, Medford, MA 02155
    8 Ralph St, Medford, MA 02155
    8 Ralph St, Medford, MA 02155
    /40

    $799,900

    • 3 Beds
    • 3 Baths
    • 1,842 Sq Ft

    8 Ralph St, Medford, MA 02155

    Exceptional Colonial in much sought after area! Gleaming hardwood floors abound throughout the spacious sun-filled living room, formal dining room w/sliders leading to two-tier deck overlooking the huge back yard with Gazebo and extra storage sheds offering potential for outdoor enjoyment and landscaping endeavors. Ultra remodeled kitchen w/Quartz Counters and Cherry Cabinets. Cozy family den and

    Diane Chuha Bond Realty, Inc.

    8 Ralph St, Medford, MA 02155
  • 722 Highland Ave, Malden, MA 02148
    722 Highland Ave, Malden, MA 02148
    722 Highland Ave, Malden, MA 02148
    /27

    $995,000

    • 4 Beds
    • 3 Baths
    • 2,013 Sq Ft

    722 Highland Ave, Malden, MA 02148

    Beautiful 2-family home located in Malden’s desirable West End, offering an excellent opportunity for both owner-occupants and investors. Unit 1 is currently rented, and well-maintained, long-term tenant in place with a strong history of on-time payments. while Unit 2 offer large layouts with great ceiling height, flexible floor plans, and tremendous potential for customization. Updates are

    Tianshi Liang Hooli Homes Boston

    722 Highland Ave, Malden, MA 02148
  • 46A Wentworth St, Malden, MA 02148
    46A Wentworth St, Malden, MA 02148
    46A Wentworth St, Malden, MA 02148
    /42

    $975,000

    • 5 Beds
    • 2 Baths
    • 2,208 Sq Ft

    46A Wentworth St, Malden, MA 02148

    5 BEDROOM/2 BATH . OWNER OCCUPIED FOR OVER 60 YEARS AND WELL MAINTAINED. NEWER ROOF (see drone photo) , NEWER SIDING, AMAZING AMOUNT OF OFF STREET PARKING HARD TO FIND. (see photo of plot plan) NEWER PAVED DRIVEWAY, 4 MINUTE WALK TO TRAIN. All new copper pipes to the street. Delivered empty of tenants. Unit #2 was getting $1950 a month and has home office and large updated kitchen . Laundry for

    Beth McGaffigan RE/MAX Encore

    46A Wentworth St, Malden, MA 02148
  • 92 Overlook Rd, Arlington, MA 02474
    92 Overlook Rd, Arlington, MA 02474
    92 Overlook Rd, Arlington, MA 02474
    /42

    $1,745,000

    • 4 Beds
    • 3.5 Baths
    • 2,936 Sq Ft

    92 Overlook Rd, Arlington, MA 02474

    Spectacular new construction on Arlington’s highly sought-after East Side, just approximately 1.5 miles from vibrant Arlington Center. This exceptional home showcases the builder’s pride of ownership and superior craftsmanship, with thoughtful attention to detail at every turn. A rare offering, this home features 4 spacious bedrooms, 3.5 beautifully appointed bathrooms, and 3 full levels of

    The Joanna Schlansky Residential Team Elite Realty Experts, LLC

    92 Overlook Rd, Arlington, MA 02474
  • 0 & 15 Whitman Rd, Medford, MA 02155
    0 & 15 Whitman Rd, Medford, MA 02155
    0 & 15 Whitman Rd, Medford, MA 02155
    /39

    $1,399,000

    • 4 Beds
    • 2 Baths
    • 2,064 Sq Ft

    0 & 15 Whitman Rd, Medford, MA 02155

    Treat yourself to a new home in 2026! Highly sought after West Medford neighborhood located close to the commuter rail, Brooks Elementary, local library and restaurants, with quick access to highway routes. This beautifully renovated Dutch/Colonial home was renovated in 2023 and includes a second lot providing a large, fenced in, outdoor space that’s unrivaled! Inside, you are welcomed with the

    Trevor Gearin Lamacchia Realty, Inc.

    0 & 15 Whitman Rd, Medford, MA 02155
  • 62 Foundry St Unit 312, Wakefield, MA 01880
    62 Foundry St Unit 312, Wakefield, MA 01880
    62 Foundry St Unit 312, Wakefield, MA 01880
    /32

    $949,900

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft

    62 Foundry St Unit 312, Wakefield, MA 01880

    Unique offering! Experience refined living at the AWARD WINNING Wrenly Residences - Where Luxury Meets Lifestyle. This elegant 2-bedroom, 2-bathroom condo spans over 1,300 square feet all on one level, featuring engineered hardwood floors and a designer kitchen with top-of-the-line appliances. The spacious primary suite includes ample closet space and a luxurious tiled en-suite bathroom. The

    Aranson Maguire Group Compass

    62 Foundry St Unit 312, Wakefield, MA 01880
  • 53 Perkins St, Stoneham, MA 02180
    53 Perkins St, Stoneham, MA 02180
    53 Perkins St, Stoneham, MA 02180
    /34

    $799,000

    • 2 Beds
    • 1.5 Baths
    • 1,244 Sq Ft

    53 Perkins St, Stoneham, MA 02180

    Condo Alternative! This meticulously renovated Cape-style home offers the perfect blend of classic charm and modern efficiency, featuring a total top-to-bottom transformation. The exterior boasts brand-new wood siding and windows, while the interior has been largely gutted and rebuilt with all-new electrical systems and central air conditioning for year-round comfort. The heart of the home is the

    Kathy Platcow Harbor View Real Estate Corp.

    53 Perkins St, Stoneham, MA 02180
  • 149 Pearl St, Malden, MA 02148
    149 Pearl St, Malden, MA 02148
    149 Pearl St, Malden, MA 02148
    /42

    $959,000

    • 3 Beds
    • 2 Baths
    • 2,647 Sq Ft

    149 Pearl St, Malden, MA 02148

    BRAND NEW CONSTRUCTION! This modern farmhouse blends timeless charm with modern design. The great room features high ceilings and LED recessed lighting, creating a bright, open space for everyday living. A dining area leads to the chef’s kitchen, beautifully appointed with stainless steel appliances and gas cooking. Adjoining the kitchen, you’ll find an oversized bonus room with a rear entrance

    Robert Leahey Coldwell Banker Realty - Waltham

    149 Pearl St, Malden, MA 02148
  • 27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    27 Everett Ave, Winchester, MA 01890
    /39

    $3,599,000

    • 6 Beds
    • 5.5 Baths
    • 7,431 Sq Ft

    27 Everett Ave, Winchester, MA 01890

    This exceptional Everett Avenue residence stands among the street’s most distinguished offerings, commanding a premier setting on over half an acre. Renovated in 2023-2025, timeless architecture is seamlessly married to today’s most coveted amenities. Hallmark architectural details abound. Balusters, soaring ceilings, coffered rooms, original crown moldings, mantels, and decorative trim are

    Nancy Pallotta Gibson Sotheby's International Realty

    27 Everett Ave, Winchester, MA 01890
  • 18 Cranston Cir, Woburn, MA 01801
    18 Cranston Cir, Woburn, MA 01801
    18 Cranston Cir, Woburn, MA 01801
    /42

    $789,900

    • 3 Beds
    • 2 Baths
    • 1,642 Sq Ft

    18 Cranston Cir, Woburn, MA 01801

    Situated on a peaceful cul-de-sac in a sought-after neighborhood, 18 Cranston Circle offers a quintessential suburban lifestyle in the heart of Woburn. This charming residence features a well-proportioned layout with bright living spaces, perfect for both daily comfort and weekend entertaining. The property boasts a spacious yard that provides a private oasis for outdoor activities, gardening, or

    Team ROVI Real Broker MA, LLC

    18 Cranston Cir, Woburn, MA 01801
  • 62 High St Unit Lot 5, Stoneham, MA 02180
    62 High St Unit Lot 5, Stoneham, MA 02180
    62 High St Unit Lot 5, Stoneham, MA 02180
    /15

    $1,475,000

    • 4 Beds
    • 2.5 Baths
    • 2,442 Sq Ft

    62 High St Unit Lot 5, Stoneham, MA 02180

    Only 5 homes left at Stoneham Heights! Stoneham’s newest and most prestigious neighborhood. Discover Stoneham Heights, an exclusive collection of 13 newly constructed, architect-designed, single-family residences. Crafted by a local builder with high-quality materials, these homes offer modern design and open floor plans for today’s lifestyle. Exceptional features include gourmet kitchens,

    Erin Anderson Anderson Realty Partners

    62 High St Unit Lot 5, Stoneham, MA 02180
  • 1025 Massachusetts Ave Unit 211, Arlington, MA 02476
    1025 Massachusetts Ave Unit 211, Arlington, MA 02476
    1025 Massachusetts Ave Unit 211, Arlington, MA 02476
    /37

    $1,011,500 New Construction

    • 1 Bed
    • 2 Baths
    • 1,231 Sq Ft

    1025 Massachusetts Ave Unit 211, Arlington, MA 02476

    OPEN HOUSE Th/Fri/Sat 11-2pm. Welcome to Majestic Mill Brook, a luxury new construction condo complex built by The Maggiore Companies. Low-emissions development with high-quality finishes and contemporary flair. This stylish 1 bed, 2 full bath residence offers open-concept living and dining area seamlessly connected to a modern kitchen, complete with electric range, exterior-vented exhaust hood

    Paul Cirignano The Synergy Group

    1025 Massachusetts Ave Unit 211, Arlington, MA 02476
  • 14 Church Ave, Woburn, MA 01801
    14 Church Ave, Woburn, MA 01801
    /2

    $1,498,000

    • 5 Beds
    • 4 Baths
    • 3,276 Sq Ft

    14 Church Ave, Woburn, MA 01801

    A Rare Opportunity in Woburn Town Center! Discover this exceptional property featuring four condo units perfectly situated in the vibrant heart of Woburn. This well-cared-for building offers ample parking and strong income-producing potential, making it a standout choice for savvy Buyers. With possibilities for interior expansion and value-add improvements, the property offers versatility whether

    Suraj Tamrakar Stuart St James, Inc.

    14 Church Ave, Woburn, MA 01801
  • 33 Lake Ave, Stoneham, MA 02180
    33 Lake Ave, Stoneham, MA 02180
    33 Lake Ave, Stoneham, MA 02180
    /39

    $949,000

    • 4 Beds
    • 2.5 Baths
    • 2,825 Sq Ft

    33 Lake Ave, Stoneham, MA 02180

    Gorgeous Brick Front Split Entry, Nestled, Secluded and gazing down upon a fantastic Colonial Park School Neighborhood...Welcome to 33 Lake Avenue, Stoneham. This Oversized, 2,800+ square foot (according to Town Records) Split Entry Home has all the extras. Central Air, Sprinkler System, Primary Bedroom with Bath connected Primary Bedroom Sunroom, Garage, Inground Pool (See Disclosures). Large

    Craig Celli Century 21 North East

    33 Lake Ave, Stoneham, MA 02180
  • 19 Indian Hill Rd, Woburn, MA 01801
    19 Indian Hill Rd, Woburn, MA 01801
    19 Indian Hill Rd, Woburn, MA 01801
    /32

    $849,900

    • 4 Beds
    • 2 Baths
    • 1,778 Sq Ft

    19 Indian Hill Rd, Woburn, MA 01801

    Classic charm, thoughtful updates, and an unbeatable West Side location—this beautifully maintained Cape checks every box. Set atop a highly desirable westside neighborhood, this inviting home blends traditional character with a spacious family room addition featuring vaulted ceilings, ideal for everyday living and entertaining. The first floor offers an open flow from the dining room with

    Joanne Mulkerin J. Mulkerin Realty

    19 Indian Hill Rd, Woburn, MA 01801
  • 35 Wright St, Stoneham, MA 02180
    35 Wright St, Stoneham, MA 02180
    35 Wright St, Stoneham, MA 02180
    /31

    $699,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    35 Wright St, Stoneham, MA 02180

    Gorgeous, fully renovated home in one of the best locations for commuting to Boston you've ever seen! The commute can be as quick as 10 minutes! Location is also walking distance to all of downtown Stoneham's fabulous restaurants and shops. This home was completely overhauled in 2024 with gorgeous herringbone hardwood flooring, open concept layout, accent wall in the living area, modern two-tone

    Jeanna Alimonti Clements Realty Group

    35 Wright St, Stoneham, MA 02180
  • 6 Stratton Dr Unit 307, Woburn, MA 01801
    6 Stratton Dr Unit 307, Woburn, MA 01801
    6 Stratton Dr Unit 307, Woburn, MA 01801
    /26

    $924,999 New Construction

    • 2 Beds
    • 2 Baths
    • 1,582 Sq Ft

    6 Stratton Dr Unit 307, Woburn, MA 01801

    Last chance to own a move-in ready home at Highland at Vale in Woburn! The Ivywood home design offers a corner unit filled with natural light. The kitchen, perfect for your inner chef, features stainless steel appliances, an oversized island, and soft-closing cabinets. The open floor plan makes entertaining a breeze—host in the private dining area, then relax in the gathering room. The owner's

    Erin Sullivan Pulte Homes of New England

    6 Stratton Dr Unit 307, Woburn, MA 01801
Massachusetts Middlesex County Winchester Winchester Highlands

Real Estate & Homes for Sale in Winchester Highlands, Winchester

Why Live in Winchester Highlands
Winchester Highlands is a neighborhood known for its diverse and grand homes, ranging from late 19th-century builds to contemporary houses, featuring styles such as ranches, colonials, and two-family homes. The area is part of one of the best public school districts in the state, with highly rated institutions like Muraco Elementary, McCall Middle, and Winchester High School, all offering robust academic and extracurricular programs. The neighborhood is safer than the national average, providing a secure environment for residents. Outdoor enthusiasts will appreciate the proximity to the 2,200-acre Middlesex Fells Reservation, which features over 100 miles of trails, and the Tri-Community Greenway, a paved path for walking, jogging, and biking. Winchester Highlands also has local dining options like Eighty Eight Cafe and The Gingerbread Construction Co., with more restaurants and a Stop & Shop located in nearby Winchester Center. The neighborhood is well-connected, with the Massachusetts Bay Transportation Authority commuter rail at Winchester Center offering a roughly one-hour ride to Boston, and Interstate 93 providing a convenient 11-mile drive to the city. Additionally, Winchester Hospital, a 229-bed medical center, is located within the neighborhood. Residents can enjoy community events such as Winchester Town Day, which features a block party, street fair, and fireworks each June.
Learn more about living in Winchester Highlands

Frequently Asked Questions

Is Winchester Highlands a good place to live?
Winchester Highlands is a good place to live. Winchester Highlands is considered very car-dependent and somewhat bikeable. Winchester Highlands is a suburban neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. Winchester Highlands has 7 parks for recreational activities. It is fairly sparse in population with 5.2 people per acre and a median age of 43. The average household income is $187,882 which is above the national average. College graduates make up 70.1% of residents. A majority of residents in Winchester Highlands are home owners, with 23.9% of residents renting and 76.1% of residents owning their home. A local real estate agent serving Winchester Highlands can help you decide if this neighborhood is the right one for you. Learn more on our Winchester Highlands neighborhood guide.
Is Winchester Highlands, MA a safe neighborhood?
Winchester Highlands, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
How much do you need to make to afford a house in Winchester Highlands?
The median home price in Winchester Highlands is $1,250,000. If you put a 20% down payment of $250,000 and had a 30-year fixed mortgage with an interest rate of 6.1%, your estimated principal and interest payment would be $6,060 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $260K a year to afford the median home price in Winchester Highlands. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winchester Highlands is $188K.
What are the best public schools in Winchester Highlands?
The best public schools that serve Winchester Highlands are:
What are the best private schools in Winchester Highlands?
The best private schools that serve Winchester Highlands are:
  • Greater Boston Academy has an A+ Niche grade, a student teacher ratio of 15:1 and an average review score of 4.9.
  • Acera School has an A Niche grade, a student teacher ratio of 4:1 and an average review score of 4.1.
  • St. Patrick Elementary School has an A- Niche grade, a student teacher ratio of 13:1 and an average review score of 4.2.
What are the most popular zip codes in Winchester Highlands, Winchester, MA?
The most popular zip codes in Winchester Highlands, Winchester, MA include 01890, 02180, 01801, 02155 and 02176.
What are the most popular neighborhoods near Winchester Highlands, Winchester, MA?
The most popular neighborhoods near Winchester Highlands, Winchester, MA are Nobility Hill, Walnut Hill, Haywardville, North Main and Downtown Woburn.

Home Trends in Winchester Highlands, MA

On average, homes in Winchester Highlands, Winchester sell after 18 days on the market compared to the national average of 53 days. The median sale price for homes in Winchester Highlands, Winchester over the last 12 months is $1,250,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,250,000
Median Single Family Sale Price
$1,265,000
Average Price Per Sq Ft
$592
Number of Homes for Sale
0
Last 12 months Home Sales
39
Months of Supply
0.00
Median List Price
$1,250,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
4%
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