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.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Joan Francis "Joan" Sullivan
$2,975,000 (USD)
Winchester Area Single Family Home
Active
115 Church St Winchester, MA 01890
7 Bed
4.2 Baths
5888 sqft
MLS# 73512327
Distinguished Colonial Revival located in the desirable “Flats neighborhood offering 5,888 SF with 7 bedrooms and 6 baths across three finished levels. Period details include a quartered oak foyer and staircase, bay windows, pocket doors, and decorative millwork. Chef's kitchen features a Viking gas range, Thermador refrigerator, and granite countertops. Family room has a wood-burning fireplace and built-ins. Formal living and dining rooms offer generous proportions and period character. Second floor hosts a primary with en suite bath, a second en suite bedroom, and two additional bedrooms served by a hall bath. Renovated third floor features wide pine floors, a full bath, and flexible space for offices or bedrooms. Recreation room has a wet bar, half bath, and a balcony. Situated on a .41-acre corner lot that boasts a large flagstone patio, a basketball court and driveway access from Wedgemere Avenue. Minutes to Winchester Center, commuter rail, schools, and conservation trails.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Jenny Ryer
$2,500,000 (USD)
Winchester Area Single Family Home
Contingent
15 York Road Winchester, MA 01890
5 Bed
3.5 Baths
4500 sqft
MLS# 73510389
This 5-bed colonial was built in 2017 and offers a bright open floor plan ideal for today’s lifestyle. The kitchen features a large quartz island, breakfast nook, and flows into dining and living areas with gas fireplace. Sliders open to a private lot with stone patio and fire pit. First floor includes half bath, pantry, and an enormous mudroom with cubbies for everyone. The oversized primary suite offers a marble bath and bonus space for a gym or office. Two large bedrooms and full bath on second floor. Third floor adds two bedrooms, a full bathroom, and laundry room. Finished basement provides additional living space perfect for play room or game room, with ample storage. Two-car detached garage with overhead flex space. Modern construction, updated finishes, and a true neighborhood setting makes this home a perfect fit!
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Nannette Shanahan
$2,299,000 (USD)
Winchester Area Single Family Home
Contingent
216 Highland Avenue Winchester, MA 01890
5 Bed
3.5 Baths
4822 sqft
MLS# 73511014
Welcome to this fully updated 5 BR, 3.5 BA Victorian showcasing elegant period detail throughout, including intricate woodwork, moldings, high ceilings & hardwood floors. The main level features a gourmet eat-in kitchen w/ quartz island & high-end stainless appliances, opening to a custom butler’s pantry w/ additional oven, sink & wine chiller. A sun-filled family room w/French doors leads to the patio, along w/ a fireplaced living room w/ built-ins, & formal dining room. Home includes 2 primary bedroom options, one on the 2nd floor & a private 3rd-floor primary suite w/ fireplace & full bath. The 2nd level also has 3 additional spacious bedrooms & two full baths, while the 3rd floor features a dramatic great room w/ beamed ceiling.Additional highlights include partially finished basement & newer heat & AC. Enjoy a wrap-around porch, patio & large fenced yard. Ideally located near town center, Middlesex Fells Reservation, Commuter Rail, Lincoln Elementary, Middle School, & Highschool.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Paula Sughrue
$1,700,000 (USD)
Winchester Area Single Family Home
Contingent
307 Cross Street Winchester, MA 01890
5 Bed
5 Baths
3500 sqft
MLS# 73508927
Thoughtfully reimagined & expanded in 2019, this sophisticated colonial offers 5-6 bedrooms & 5 baths with a beautiful open floor plan - perfect for a growing family or multi-generational living. A striking granite kitchen with crisp white cabinetry, premium stainless appliances & oversized island flows seamlessly into the dining area - ideal for everyday living & refined entertaining. A fireplaced living room, office, bedroom & full bath complete this main level. Upstairs, two spacious bedrooms & a family bath complement a serene primary suite with spa-like bath amenities. The 3rd level offers an additional primary suite with luxurious soaking tub & flexible bonus space to use how you choose. A finished walk-out lower level with wet bar, bath, family room, exercise & play space adds further appeal. Acoustic windows enhance comfort throughout. Enjoy the one car garage, fully fenced yard, patio & deck - just moments to parks, town center, major routes, & Winchester's top-rated schools.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Dara Singleton
$1,500,000 (USD)
Winchester Area Condominium
Active
38 Salem Street 38 Winchester, MA 01890
5 Bed
3.5 Baths
3362 sqft
MLS# 73513154
A rare opportunity to enjoy easy, yet refined living in Winchester, this well-maintained newer construction home offers 4-5 bedrooms and 3 ½ baths with a thoughtfully designed open floor plan. The main level features a spacious living area, eat-in kitchen with granite countertops, stainless steel appliances and pantry, along with a ½ bath and practical mudroom for everyday ease. Upstairs, generously proportioned bedrooms provide comfort and flexibility across two levels. The finished lower level with laundry adds valuable living space. Outside, an oversized paver driveway, two-car attached garage and inviting patio overlook a pleasant and private backyard setting. Ideally located just moments to the town center commuter rail, local shops and dining, and nearby schools, including brand new Lynch Elementary School. Move-in ready and offering exceptional value in a sought-after location.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Dara Singleton
$1,500,000 (USD)
Winchester Area Single Family Home
Active
38 Salem Street Winchester, MA 01890
5 Bed
3.5 Baths
3362 sqft
MLS# 73513155
A rare opportunity to enjoy easy, yet refined living in Winchester, this well-maintained newer construction home offers 4-5 bedrooms and 3 ½ baths with a thoughtfully designed open floor plan. The main level features a spacious living area, eat-in kitchen with granite countertops, stainless steel appliances and pantry, along with a ½ bath and practical mudroom for everyday ease. Upstairs, generously proportioned bedrooms provide comfort and flexibility across two levels. The finished lower level with laundry adds valuable living space. Outside, an oversized paver driveway, two-car attached garage and inviting patio overlook a pleasant and private backyard setting. Ideally located just moments to the town center commuter rail, local shops and dining, and nearby schools, including brand new Lynch Elementary School. Move-in ready and offering exceptional value in a sought-after location.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Dara Singleton
$1,325,000 (USD)
Medford Area Multi-Family Home
Active
70-72 Windsor Road Medford, MA 02155
5 Bed
2 Baths
2134 sqft
MLS# 73497310
Exceptional 2-family on a prime corner lot just steps from Tufts University and Green Line. Enjoy open views toward Alumni Field in one of the area’s most desirable neighborhoods. This turnkey property features two well-separated units, each unit with private off-street parking for two cars, offering great rental potential, owner-occupant, or condo living. Bright, open interiors benefit from abundant natural light. The upper unit is a fully renovated 3-bedroom with modern kitchen, bath, and in-unit laundry. The lower unit is a spacious 2-bedroom with strong rental history. Major updates include central A/C and heating systems (2017&2024) in both units,& renovated front and rear porches. Lead compliant and separately water-metered, minimizing owner expenses. The corner lot, space and light, location, two separate off-street parking areas and overall condition set this home apart from others in the Tufts area, presenting a rare opportunity to own a well-located, upper-tier 2-family home.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Michael Rauseo
$1,300,000 (USD)
Winchester Area Condominium
Contingent
7 Wainwright Road 30 Winchester, MA 01890
3 Bed
3.5 Baths
2803 sqft
MLS# 73513982
This three bedroom condo in Winchester offers 2025 kitchen and bath updates with a thoughtfully designed, expansive layout across multiple levels. Hardwood floors span the first level with a den and open living and dining area ideal for everyday living and entertaining. The second floor features a generous primary suite with walk-in glass shower and stackable laundry, plus an additional bedroom and full bath. The lower level adds a bedroom, full bath, and office, providing flexible space for guests or work from home. New front windows in 2025 enhance natural light. Enjoy treetop views from the private deck, perfect for watching the sunset. Set within a beautifully landscaped community surrounded by lush greenery, this home blends space, comfort, and modern updates in Winchester.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Karen Garrett
$1,100,000 (USD)
Winchester Area Condominium
Active
83 Church Street 15 Winchester, MA 01890
2 Bed
1.5 Baths
1365 sqft
MLS# 73497739
Stunning corner unit, fully renovated 2 BR,1.5 BA condo offering an exceptional blend of elegance & modern updates in a prime in-town location.Soaring ceilings, dramatic arched openings, & oversized windows flood the space w/natural light.French doors open to charming private balcony.Main living area showcases beautifully refinished marble flooring, gas FP, & designer lighting including crystal chandeliers & wall sconces. The thoughtfully renovated kitchen features granite countertops, custom cabinetry, stainless steel appliances, & opens to a stylish butler’s pantry complete w/wine fridge, sink, & in-unit washer/dryer. Upstairs, both bedrooms offer HW flooring, updated lighting, & skylight w/shade. Bathrooms have been tastefully updated. Additional highlights include updated electrical, gas line connection, & integrated sound wiring.Includes one car garage, an additional outdoor parking space & basement storage w/bonus cedar closet.Turnkey home near town center, shops & commuter rail.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Paula Sughrue
$750,000 (USD)
Medford Area Single Family Home
Active
161 Main Street Medford, MA 02155
3 Bed
1.5 Baths
1166 sqft
MLS# 73508358
Looking for a charming, move-in-ready single family home? 161 Main Street checks all the boxes. This home has been thoughtfully upgraded with a brand-new roof, new windows, updated electrical service, new heating system, new water heater, and newly added central A/C, offering modern comfort and peace of mind. This adorable 3 bedroom, 1.5 bath home has so much to offer. The spacious first-floor bedroom and open-concept layout create an inviting flow, with the modern kitchen seamlessly connecting to the living room. Upstairs, you’ll find a generously sized primary bedroom with two closets, a third bedroom, and a beautifully renovated full bathroom. With easy access to Medford Square’s dining and shops, Tufts University, Davis Square and Green line the location is hard to beat. The cozy outdoor patio space is perfect for grilling, relaxing, and gathering. A must see!!!
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Michael Rauseo
$699,000 (USD)
Medford Area Single Family Home
Active
19 Fourth St 19 Medford, MA 02155
2 Bed
2 Baths
1050 sqft
MLS# 73509469
Newly gut renovated 2 bedroom, 2 full bath duplex-style condo. This inviting home sits on a quiet street and offers a seamless open-concept layout and dining area, ideal for entertaining and daily living. The modern, white kitchen features a spacious island, stylish lighting, and a full suite of stainless appliances. Two sizable bedrooms, two updated baths, in-unit laundry, and generous storage add to the home’s comfort and convenience. Enjoy an exclusive, rear deck, a small garden area, beautiful plantings plus additional basement storage. Two deeded off-street parking spaces come with this unit. Ideally located near tennis and basketball courts, a dog-friendly park, splash pad, the Wellington T, Assembly Row shops, and the Northern Strand bike path. This condo sits on a quiet street, has a low $210/month condo fee and is a short commute to Boston or Cambridge -do not miss your opportunity to own!
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Lynne Russo
$690,000 (USD)
Barnstable Area Single Family Home
Active
37 Ansel Howland Road Barnstable, MA 02632
3 Bed
2 Baths
2650 sqft
MLS# 73498124
Welcome to 37 Ansel Howland Road, located in one of the most sought-after neighborhoods in Centerville. Whether you’re searching for a year-round home or a seasonal Cape retreat, this property is move in ready, delivering comfort, flexibility, and location. The main level features an inviting open concept layout for the living, kitchen and dining spaces. Three generous bedrooms, including a private primary en-suite, an additional full bath, and laundry, round out the main floor, offering convenience of one-level living. The finished lower level provides additional options for potential media room, playroom, home office, fitness area, etc. Enjoy summer evenings on the covered patio, overlooking a beautiful level yard perfect for gardening, relaxing, or entertaining. Central A/C and an attached one car garage complete this meticulously maintained home. All just minutes from Craigville Beach and the village shops and amenities in Centerville.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Melissa Perrone
$690,000 (USD)
Centerville Area Single Family Home
Active
37 Ansel Howland Road Centerville, MA 02632
3 Bed
2 Baths
2650 sqft
MLS# 22601299
Welcome to 37 Ansel Howland Road, located in one of the most sought-after neighborhoods in Centerville. Whether you're searching for a year-round home or a seasonal Cape retreat, this property is move in ready, delivering comfort, flexibility, and location. The main level features an inviting open concept layout for the living, kitchen and dining spaces. Three generous bedrooms, including a private primary en-suite, an additional full bath, and laundry, round out the main floor, offering convenience of one-level living. The finished lower level provides additional options for potential family room, home office, fitness area, etc. Enjoy summer evenings on the covered patio, overlooking a beautiful level yard perfect for gardening, relaxing, or entertaining. Central A/C and an attached one car garage complete this meticulously maintained home. All just minutes from Craigville Beach and the village shops and amenities in Centerville.
Listing Courtesy of CCIMLS / Better Homes And Gardens Real Estate The Shanahan Group / Melissa Perrone
$485,000 (USD)
Stoneham Area Condominium
Active
144 Marble St 403 Stoneham, MA 02180
2 Bed
2 Baths
1295 sqft
MLS# 73508197
Welcome to The Gates of Stoneham, a desirable and well-maintained condo community on the Winchester/Stoneham line. This bright 2-bed, 2 bath home offers 1,295 sq ft of move-in-ready space with elevator access and assigned parking. The open-concept layout includes a generously sized kitchen and separate dining area, perfect for everyday living and entertaining. Sunlight pours in through glass doors leading to an expansive 43-foot private balcony. Enjoy the sunset or morning coffee with beautiful views of the landscaped grounds. The primary suite features a custom walk-in closet and an updated private bath, while the second bedroom and full bath provide flexibility. Additional highlights include an amazing community, AC, storage, and laundry across the hall. Residents enjoy included amenities such as an outdoor pool, clubhouse for entertaining, a sauna, large lobby and guest parking, all with access to Boston, shops, restaurants and the Middlesex Fells.
Listing Courtesy of MLS PIN / Better Homes And Gardens Real Estate The Shanahan Group / Lynne Russo