Boston Open Houses This Weekend: May 15-17,2026

Tour Featured Homes Across Boston, Newton, Back Bay, Brighton, Jamaica Plain & Beyond

This weekend’s open house lineup offers buyers an opportunity to explore a wide range of properties across Greater Boston and Central Massachusetts, from historic Back Bay brownstones and city condos to expansive Colonials in Newton and Westminster. As spring inventory continues to move quickly throughout the region, buyers are increasingly using weekend open houses to compare neighborhoods, home styles, renovation quality, and overall value before competition intensifies further into the season.

Whether you are searching for your first condo, a long-term family home, or an investment opportunity, touring homes in person remains one of the most effective ways to understand today’s market. If you’re preparing to buy this year, be sure to also explore our [First-Time Home Buyer Resources], [Boston Neighborhood Guides], and [Buying a Home in Greater Boston] pages for additional insights and planning tools.

👉 Boston’s spring real estate market continues to reward buyers who start touring homes early and stay informed on neighborhood trends.

What Buyers Are Looking for This Spring

Across Greater Boston, buyer demand continues to center around move-in ready homes, flexible layouts, updated kitchens, outdoor space, and commuter accessibility. Many buyers are also comparing the lifestyle differences between city neighborhoods and suburban communities more closely than ever before. While Boston condos continue to attract professionals and investors seeking walkability and transit access, larger suburban homes remain highly desirable for buyers prioritizing square footage, private outdoor space, and long-term flexibility.

This weekend’s open houses highlight how varied the market has become, offering everything from historic homes with preserved character to fully renovated modern living spaces throughout Newton, Dedham, Brighton, Back Bay, and Westminster.

👉 Buyers exploring multiple neighborhoods often uncover stronger value opportunities and lifestyle fits they had not originally considered.

Featured Open Houses This Weekend

243 Upland Ave, Newton ($2,150,000)

Saturday & Sunday: 2:00 PM – 4:00 PM

Perched atop one of Newton Highlands’ most sought-after hilltop locations, this award-winning Colonial blends historic charm with high-end modern upgrades throughout nearly 3,850 square feet of living space. The property features four bedrooms, five bathrooms, multiple fireplaces, a chef’s kitchen with Sub-Zero appliances, expansive two-level deck space, and a luxurious primary suite with spa-inspired finishes.

The home’s setting is especially notable, surrounded by luxury properties and mature wooded views while remaining convenient to Newton’s village centers, parks, and commuter routes. With architectural details preserved alongside thoughtful renovations, the property offers a rare combination of character, scale, and future potential in one of Greater Boston’s strongest luxury markets.

Open house hosted by Adam Kotkin, Dan Bedjanov, and Max Rosenberg.

👉 Luxury homes in Newton Highlands continue to see strong demand due to their balance of privacy, prestige, and commuter convenience.

2031 Commonwealth Ave, Newton ($1,490,000)

Saturday: 11:00 AM – 12:00 PM

Located along the serene carriage lane of Commonwealth Avenue in Auburndale, this beautifully restored Dutch Colonial blends historic character with a complete modern renovation. The five-bedroom home features nearly 2,900 square feet of living space, including a bright open kitchen, spacious family room, preserved woodwork details, and a finished lower level with a private entrance ideal for guests or extended family.

The property also includes an oversized deck, central air, updated bathrooms, and flexible living areas that work well for larger households or hybrid work setups. Open house hosted by Jake Rosenberg.

👉 Renovated single-family homes in Newton remain some of the most competitive listings in the Greater Boston market.

56 Riverview St, Dedham ($779,000)

Saturday: 12:00 PM – 1:00 PM | Sunday: 12:00 PM – 2:00 PM

This newly renovated Riverdale cottage offers a strong alternative for buyers seeking a turnkey suburban home with modern systems and outdoor space. The property underwent a full 2026 gut renovation and now features high ceilings, hardwood floors, quartz countertops, new bathrooms, and energy-efficient heat pumps with ductless A/C systems throughout.

One standout feature is the enormous backyard and oversized rear deck, creating a rare amount of usable outdoor space for the price point. The home also benefits from close proximity to Millennium Park, the Charles River, and several walking trails, making it especially attractive for buyers prioritizing recreation and accessibility.

Open house hosted by Sarah McIntyre.

👉 Updated homes under $800K with outdoor space continue to see strong buyer demand across Dedham and nearby suburbs.

829 Chestnut St, Newton ($1,899,000)

Saturday: 12:00 PM – 1:30 PM | Sunday: 12:00 PM – 1:00 PM

Situated in Waban, one of Newton’s most desirable villages, this expansive Colonial delivers over 4,800 square feet of living space across four finished levels. The home features five bedrooms, four-and-a-half bathrooms, multiple fireplaces, a dramatic cathedral-ceiling family room, and a large landscaped backyard with an oversized rear deck.

Inside, the layout balances formal entertaining space with comfortable everyday living. The third-floor guest suite and office create flexibility for remote work or multigenerational living, while the finished lower level includes additional recreation and wellness space. Located moments from Waban Center and the MBTA Green Line, the property combines suburban privacy with commuter convenience.

Open house hosted by Eric Anderson and Max Rosenberg.

👉 Luxury homes near village centers and transit remain highly sought-after throughout Newton’s spring market.

2 Seaver Street, Westminster ($629,999)

Saturday: 11:00 AM – 1:00 PM and Sunday: 12:00 PM – 2:00 PM

For buyers looking beyond Greater Boston’s urban core, this historic 1854 Colonial in Westminster offers a unique opportunity to own a beautifully preserved New England home with over 2,500 square feet of living space and a massive attached three-level barn. The property includes four bedrooms, three full bathrooms, original character details, wood-burning stove accents, updated systems, and generous outdoor space on a 0.75-acre lot.

The home blends historic craftsmanship with practical modern living, featuring flexible office space, large gathering rooms, and direct access to outdoor recreation near Wachusett Mountain. Buyers searching for more space and historic character outside Boston’s immediate suburbs may find strong value in communities like Westminster.

Open house hosted by Katy Moy.

👉 Historic homes with acreage and flexible bonus space continue attracting buyers seeking alternatives to denser suburban markets.

80 Marlborough St #7, Back Bay ($619,000)

Saturday & Sunday: 12:00 PM – 2:00 PM

Situated inside a classic Back Bay brownstone just steps from the Public Garden and Newbury Street, this beautifully updated studio condo offers a refined city lifestyle in one of Boston’s most iconic neighborhoods. The unit features soaring 11-foot ceilings, oversized bay windows, crown molding, central air, a marble fireplace, and a renovated kitchen with stainless steel appliances.

Back Bay remains one of Boston’s premier residential destinations due to its historic architecture, walkability, and proximity to shopping, dining, and green space. Buyers seeking a true city-living experience will likely appreciate the property’s blend of historic charm and modern functionality.

Open house hosted by Dan Bedjanov.

👉 Well-located Back Bay condos continue to hold strong long-term appeal for both owner-occupants and investors.

5 Spofford St #11, Allston ($649,000)

Sunday: 12:00 PM – 2:00 PM

This Packard’s Corner condo places buyers directly in one of Boston’s most active rental and investment corridors. The two-bedroom unit features a renovated kitchen, hardwood floors, in-unit laundry, and a custom California Closet, all within walking distance of Boston University, Brookline, restaurants, and the Green Line.

Currently rented through July 2026 at $3,200 per month, the property also presents a compelling opportunity for investors seeking stable rental income in a high-demand neighborhood. The combination of transit access and university proximity continues to drive strong long-term demand throughout Allston and Brighton.

Open house hosted by Erika Hedden.

👉 Transit-oriented condos near universities remain among Boston’s most resilient investment property types.

1564 Commonwealth Ave #5, Brighton ($489,000)

Saturday & Sunday: 12:00 PM – 1:30 PM

This move-in-ready Brighton condo offers a quieter take on city living while remaining close to public transit, parks, restaurants, and Whole Foods. Tucked toward the rear of the building, the corner unit benefits from added privacy and reduced street noise while still sitting directly along Commonwealth Avenue.

The unit features a renovated kitchen and bathroom, hardwood flooring, bay windows, and a flexible living space ideal for both owner-occupants and investors. Professionally managed amenities and proximity to the Green Line make this an attractive option for first-time buyers looking to establish themselves within Boston proper.

Open house hosted by Dino Bacoka.

👉 Brighton continues to attract buyers seeking relative affordability with strong transit access into downtown Boston.

70 Day St #1, Jamaica Plain ($645,000)

Saturday: 11:30 AM – 1:00 PM and Sunday: 10:30 AM – 11:30 AM

Located moments from Hyde Square and Jamaica Pond, this newly converted Jamaica Plain condominium blends classic Boston architecture with updated finishes and outdoor living space. The two-bedroom unit offers over 1,000 square feet, featuring hardwood floors, oversized windows, updated stainless steel appliances, private deck space, assigned parking, and exclusive storage with laundry.

Jamaica Plain continues to attract buyers looking for neighborhood energy, walkability, green space, and a balance between city access and residential charm. The proximity to both the Orange Line and Green Line adds further convenience for commuters and long-term homeowners alike.

Open house hosted by Erika Hedden.

👉 Jamaica Plain remains one of Boston’s strongest lifestyle-driven neighborhoods for buyers seeking walkability and character.

Tips Before Touring Open Houses

Before heading out this weekend, buyers should prepare a shortlist of priorities to help compare homes more effectively. Pay close attention to layout flow, renovation quality, natural light, storage space, and neighborhood accessibility. Touring homes across different neighborhoods can also help buyers better understand where their budget stretches furthest in today’s market.

If you’re beginning your search, connecting with an experienced local agent early can also provide valuable insight into financing options, offer strategies, and upcoming inventory before properties officially hit the market.

👉 Touring homes early in your buying journey can create a major advantage once the right property becomes available.

Planning Your Weekend Tour Route

For buyers hoping to maximize their weekend, these open houses create an efficient opportunity to compare suburban and city inventory side-by-side. Newton and Dedham offer larger renovated homes with outdoor space, while Allston, Brighton, and Jamaica Plain showcase more urban condo living with strong transit access and investment potential.

If you’d like additional details on any of these listings or want recommendations tailored to your budget and goals, contact the Red Tree Real Estate team to schedule private tours or discuss upcoming inventory before it reaches the market.

👉 The best opportunities often come from seeing multiple homes and neighborhoods in the same weekend.