Browse All Holliston MA Between $500K - $600K Properties for Sale

Consider this your invitation to fall a little bit in love with Holliston! This beautifully maintained gem proves that 1,356 sq. ft. can live remarkably large. Step inside to a bright, inviting main level where gleaming hardwood floors create an effortless flow from the spacious living area into a cozy dining space. The charming kitchen brings plenty of personality with beautiful natural wood cabinetry, granite countertops, and a skylight that pours in natural light. Three comfortable bedrooms and a full bath round out the main level, while the delightful sunroom is ready for everything from morning coffee to quiet afternoons. Head downstairs to discover a versatile family room offering even more room to spread out, work from home, host guests, or create your favorite hangout space. Outside, the charm continues with a lovely white garden arbor, storage shed, and inviting yard space to enjoy in the warmer months. Recent improvements offer wonderful peace of mind, including a 2024 roof and newer heating and water heater systems, while fresh 2025 paint and 2026 washer and dryer add to the move-in-ready appeal. Enjoy all that Holliston has to offer, with Holliston High School, local shops and restaurants, parks, walking trails, and easy access to commuter routes all close by. Warm, welcoming, and wonderfully cared for, this is a home that makes everyday living feel easy!

93 Jerrold St, Holliston

$599,900

3 Beds ⋅ 1 Baths ⋅ 73567586 MLS

CHERISHED FAMILY HOME IN BRENTWOOD! Lovingly held by the same family since 1965, this classic Holliston property on Chamberlain Street offers a rare combination of long-held heritage, privacy and an extraordinary list of major brand-new improvements. Set in one of the town's most established neighborhoods, this home is ready for its next chapter to be written. At its heart is a bright kitchen featuring a convenient breakfast bar, dedicated eat-in dining area and ample counter space. Updates include the skylights with remote-controlled blinds (2026), dishwasher and oven (2025). The formal dining room and sprawling living room offer the ideal footprint to host holiday celebrations with NEW carpet (2026) while the finished lower level provides excellent, flexible bonus space. Upstairs, beautiful hardwood floors carry through all three bedrooms. A full bathroom has built-in storage that showcases the home’s authentic character. True peace of mind comes from the extensive list of big-ticket capital improvements completed by the sellers. ***Recent upgrades include a NEW roof, NEW septic system, NEW driveway, NEW 200-amp electrical panel, NEW wall-to-wall carpeting, NEW skylights, and FRESH interior paint — all completed in 2026 – with a NEW hot water tank (2024) and REBUILT AC condenser and furnace (2025).*** Exterior painted in 2022. Outside enjoy half an acre of land with plenty of room for outdoor play, gardening, or weekend entertaining. Move right in, relax, and start making your own memories from day one!

210 Chamberlain St, Holliston

$599,900

3 Beds ⋅ 1 Baths ⋅ 73564423 MLS

Welcome to 36 Regal Street! This charming ranch offers comfortable single-level living in a desirable Holliston neighborhood, just moments from the Rail Trail. The bright and inviting living room features beautiful hardwood floors and a large bay window. The spacious kitchen offers ample cabinetry, counter space, and stainless steel appliances, with a versatile bonus space perfect for a home office, dining area, playroom, or flex space.Three bedrooms and a full bath complete the main level. But the real showstopper may be outside! Set on a large, level lot, the private backyard is made for summer entertaining, complete with a spacious deck and above-ground pool, your own backyard escape just in time to enjoy the last moments of summer! A storage shed provides additional space for gardening equipment and outdoor essentials. Central air, natural gas heating, and a fantastic location close to schools, shopping, the Rail Trail, Route 16, Route 109, and major commuter routes add to the appeal. Homes like this don't come around often, move-in ready and perfectly positioned for enjoying everything this wonderful community has to offer, this is one you won't want to miss!

36 Regal St, Holliston

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Between $500K - $600K Holliston Real Estate

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