Countryside, MA homes for sale & real estate

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NEW 4 HRS AGO

ABOUT THIS HOME
Countryside, MA Homes for Sale
Situated in the prestigious Whipple Hill neighborhood, this custom-designed home offers a rare combination of privacy and artistic design. Abutting conservation land, 30 Whipple Road provides serene natural vistas and exceptional outdoor spaces, including a self-cleaning heated pool perfect for entertaining and family time. Featuring soaring ceilings and gallery like walls throughout, the residence is complemented by a striking curved staircase and architectural European windows that allow abundant natural light to fill the home. Every space has been thoughtfully curated to maximize comfort and luxury. Additionally, the property is equipped with a modern Google smart home system allowing se

$4,195,000

6 beds6 baths7,827 sq ft

30 Whipple Rd, Lexington, MA 02420

Curved staircase • Natural vistas • European windows

OPEN SAT, 2PM TO 3:30PM

ABOUT THIS HOME
Countryside, MA Homes for Sale
SAT 11/22 OH 2-3:30PM! Celebrate the holidays in this exceptional 7-bed, 7.5-bath warm modern home. offering 4 spectacular finished levels with 6,600 SF of refined living space. Wide-plank white oak flooring and soaring ceilings 10' on main level, 9' on 2nd, 8' on 3rd + LL! Custom white oak cabinetry, exposed wood beams for a warm yet contemporary feel. Enjoy entertaining in this chef’s kitchen with a large island, high-end appliances, and walk-in pantry, sep DR & LR. 1st fl guest suite or office, huge mudroom off side driveway entrance. Upstairs includes a private office/library, laundry, and 4 spacious bedrooms, including 2 primary suites! 3rd fl offers a teen/au pair suit

$3,999,000

7 beds7.5 baths6,600 sq ft

15 Peachtree Rd, Lexington, MA 02420

Private office • New construction • Wine alcove

OPEN SUN, 12PM TO 1:30PM

ABOUT THIS HOME
Countryside, MA Homes for Sale
Welcome to your modern sanctuary — a beautifully crafted contemporary new home offering the perfect blend of clean architectural lines, thoughtful functionality, and luxurious comfort. This expansive 6-bedroom residence is ideal for today's lifestyle, boasting flexible living spaces and stunning design elements throughout. At the heart of the home is a spacious great room, designed to impress and inspire. Anchored by a sleek, modern fireplace, this open-concept living area is perfect for entertaining or relaxing with family. Large windows flood the space with natural light, creating a warm and inviting ambiance. The gourmet kitchen seamlessly flows into the great room, featuring high-

$3,799,000

6 beds7.5 baths7,653 sq ft

8 Blueberry Ln, Lexington, MA 02420

Modern fireplace • Generous island • Gourmet kitchen

OPEN SAT, 12:30PM TO 2PMVIDEO TOUR

ABOUT THIS HOME
Countryside, MA Homes for Sale
Luxurious builder’s own 3 year young Contemporary Colonial features 7,634 sq. living area on a private 22,626 sq. ft. lot, just steps from conservation. Custom designed home showcases exceptional craftsmanship and modern amenities throughout. Trend setting kitchen with an oversized island, quartzite countertops, high end appliances w/ 48” gas range, warming drawer, dual dishwashers, beverage fridge, walk-in pantry. Kitchen opens to a vaulted sunroom w/ wall of windows overlooking a private yard and spacious family room with custom built-ins, gas FP, surround sound. First floor includes office/guest suite w/ full bath. Upstairs features 4 BRS w/ stunning main suite w/ vaulted cei

$3,695,000

6 beds6.5 baths7,634 sq ft

71 Webb St, Lexington, MA 02420

Custom designed home • High end appliances • Oversized island

OPEN SAT, 1:30PM TO 2:30PM

ABOUT THIS HOME
Countryside, MA Homes for Sale
* * * MOVE IN FOR THE HOLIDAYS * * * An exceptional NEW 6-bedroom, 5.5-bath modern farmhouse colonial, perfectly positioned in one of Lexington’s most coveted neighborhoods. Thoughtfully designed for both everyday comfort and sophisticated entertaining, this sun-drenched, southern-facing home showcases refined craftsmanship and timeless architectural details. Inside, wide-plank white oak floors, soaring ceilings, and elegant millwork create a sense of warmth and sophistication. At the heart of the home, the chef’s kitchen impresses with a large center island, premium appliances, wet bar, service pantry, and a sun-filled breakfast room. A first-floor suite with ensuite bath

$3,650,000

6 beds5.5 baths5,531 sq ft

22 Tyler Rd, Lexington, MA 02420

Large center island • Wet bar • Service pantry

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ABOUT THIS HOME
Countryside, MA Homes for Sale
First time offering at the exclusive Village at Winning Farm! This brand new, bright & sun filled 6/7 rm townhouse features luxury living at it's finest! This may be your only chance for one of these end units as there are a limited number of these C style units left, boasting a large open flr plan w/ three 2nd flr bdrms & hdwd flrs thru out. As you enter the foyer, at one end you'll notice a french door to the private office/den then you'll be amazed at expansive 1st flr w/ gas frplc, gorg Kit w/ island & panrty plus sliders to deck overlooking the woods. Lge prim ensuite w/ huge walk-in closet & bath w/ 2 sep sinks and an upgraded tiled shower that rivals none! Two

$999,900

3 beds2.5 baths2,000 sq ft

21 Derby Dr #21, Woburn, MA 01801

$531 HOA • Garage • Community pool

ABOUT THIS HOME
Countryside, MA Homes for Sale
Mid Century Side Hall Colonial w Attached Garage on an Attractive Corner Lot in Winchester. Available for the first time in more than fifty years, this inviting home awaits its next owners' vision and personal touch. Exceptional opportunity to add immediate value with the right repairs and upgrades. Main floor features an open living room with fireplace, adjoining dining room with southwest exposure, eat-in kitchen, half bath, and access to the garage. Four bedrooms and full bath upstairs. Above grade finished basement with full windows walks out onto a natural backyard. Desirable west end location on Thornberry Hill. Vinson-Owen Elementary School and Winchester Swim & Tennis Club in

$989,000

4 beds1.5 baths2,162 sq ft

41 Squire Rd, Winchester, MA 01890

0.34 acre lot • Garage • Community pool

OPEN SUN, 11:30AM TO 1PM3D WALKTHROUGH

ABOUT THIS HOME
Countryside, MA Homes for Sale
Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in sunroom and enjoy the peaceful wooded backdrop—your own private oasis. The luxurious first-floor primary retreat offers an oversized spa-like bathroom, a large walk-in closet, and direct access to the convenient first-floor laundry. Upstairs, you’ll find two generous bedrooms, a

$2,299,000

3 beds2.5 baths3,953 sq ft

19 Gershon Way, Winchester, MA 01890

$975 HOA • 2 garage spots • Community pool

OPEN SUN, 11:30AM TO 1PM3D WALKTHROUGH

ABOUT THIS HOME
Countryside, MA Homes for Sale
Welcome to this gorgeous 5-year-young attached single-family home in Winchester’s desirable 55+ community! Barely lived in and beautifully cared for, this home feels brand new—only better. The inviting main level features a beautiful office with coffered ceilings and a stylish kitchen and dining area that opens to a warm, fireplaced living room. From there, step into the stunning screened-in sunroom and enjoy the peaceful wooded backdrop—your own private oasis. The luxurious first-floor primary retreat offers an oversized spa-like bathroom, a large walk-in closet, and direct access to the convenient first-floor laundry. Upstairs, you’ll find two generous bedrooms, a

$2,299,000

3 beds2.5 baths3,953 sq ft

19 Gershon Way #1, Winchester, MA 01890

$975 HOA • 2 garage spots • Community pool

ABOUT THIS HOME
Countryside, MA Homes for Sale
Welcome to this beautifully updated home! The interior boasts fresh interior paint, all new lighting with refinished hardwood flooring. The living room features a cozy fireplace, perfect for relaxing evenings. The kitchen is a chef's dream with all new stainless steel appliances, new cabinets, and new counter tops with an accent backsplash adding a touch of elegance. The primary bathroom is designed for convenience with double sinks and new shower. The exterior of the home is just as impressive with fresh exterior paint and a deck for outdoor enjoyment. This home is a must-see!. Included 100-Day Home Warranty with buyer activation.

$1,475,000

3 beds2.5 baths2,316 sq ft

26 Berkshire Dr, Winchester, MA 01890

0.54 acre lot • 2 garage spots • Car-dependent

OPEN SAT, 11:30AM TO 1PMVIDEO TOUR

ABOUT THIS HOME
Countryside, MA Homes for Sale
Welcome to this stunning West side custom built 6/7 Bed, 7.5 Bath NEW construction home perched on a gorgeous lot with spectacular tree line views. Thoughtfully designed & built by top builder w/ the finest finishes. This dramatic home features soaring ceilings in the family room complemented by floor to ceiling fireplace, flooded w/ natural light ~ sliders to deck overlooking the beautiful yard. The chef's kitchen is a dream, w/ island, custom cabinetry, Thermador appl & butlers pantry. Retreat to the expansive primary bedroom w/ stunning bathroom, soaking tub & oversized shower. All bedrooms are generously sized w baths, providing plenty of space for family & guest

$2,749,000

6 beds7.5 baths7,213 sq ft

14 Liana St, Woburn, MA 01801

0.43 acre lot • 3 garage spots • Community pool

Property at 16 Solomon Pierce Rd, Lexington, MA 02420, 5 beds, 7 baths

$5,990,000

5 beds7 baths8,682 sq ft

16 Solomon Pierce Rd, Lexington, MA 02420

Property at 14 Nassau Dr, Winchester, MA 01890, 6 beds, 6 baths

$2,850,000

6 beds6 baths6,968 sq ft

14 Nassau Dr, Winchester, MA 01890

Property at 1 Maureen Rd, Lexington, MA 02420, 5 beds, 5.5 baths

$2,798,000

5 beds5.5 baths4,979 sq ft

1 Maureen Rd, Lexington, MA 02420

Property at 257 High St, Winchester, MA 01890, 5 beds, 6 baths

$3,299,000

5 beds6 baths7,101 sq ft

257 High St, Winchester, MA 01890

Property at 276 High St, Winchester, MA 01890, 5 beds, 3.5 baths

$2,299,000

5 beds3.5 baths5,006 sq ft

276 High St, Winchester, MA 01890

Property at 5 Squire Rd, Winchester, MA 01890, 6 beds, 3.5 baths

$2,000,000

6 beds3.5 baths4,696 sq ft

5 Squire Rd, Winchester, MA 01890

Property at 197 Woburn St, Lexington, MA 02420, 5 beds, 7.5 baths

$4,250,000

5 beds7.5 baths8,868 sq ft

197 Woburn St, Lexington, MA 02420

Property at 23 Thoreau Rd, Lexington, MA 02420, 6 beds, 8 baths

$5,800,000

6 beds8 baths8,649 sq ft

23 Thoreau Rd, Lexington, MA 02420

Property at 23 Burroughs Rd, Lexington, MA 02420, 6 beds, 9 baths

$5,395,000

6 beds9 baths8,220 sq ft

23 Burroughs Rd, Lexington, MA 02420

Property at 7 Lothrop Cir, Lexington, MA 02420, 6 beds, 5.5 baths

$3,485,000

6 beds5.5 baths6,707 sq ft

7 Lothrop Cir, Lexington, MA 02420

Average home prices near Countryside, MA

Cities

Neighborhoods

Winchester Town Center homes for sale
$1,499,000
Kingston homes for sale
$724,900
Arlington Heights homes for sale
$1,359,900
West Medford homes for sale
$995,000
North Waltham homes for sale
$1,177,450
Burlington Town Center homes for sale
$859,000
Belmont Hill homes for sale
$2,724,500
North Lexington homes for sale
$2,898,000
Woburn Highlands homes for sale
$695,750
Brattle homes for sale
$1,096,750

Countryside, MA real estate trends

All Home Types trends in Countryside, MA

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$2,954,444

+39.7% YoY | Oct 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2025

Growth

% YoY

Countryside, MA

$2,954,444

+39.7%

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