Homes, values and local insight for Sterling, Worcester County, Massachusetts. Typical home value $593,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Sterling is the birthplace of Mary Sawyer, whose pet lamb inspired "Mary Had a Little Lamb," and a lamb statue stands on the Town Common. It is an apple and farm town known for orchards, Davis Farmland, the Davis Mega Maze and the Sterling Fair, which bills itself as New England's largest free fair.
The area was first settled around the Waushacum Lakes in the 1640s, and Gamaliel Beaman became the first permanent settler in 1720. The town, once called Chocksett, split from Lancaster and was incorporated as Sterling in 1781, named for William Alexander, Lord Stirling. The annual town fair began on the Town Common as a farm show in 1859, and Ebenezer Butterick developed his dress patterns here in 1863. Sterling is a small farm town of over 8,000 people where orchards, farm stands and conservation land sit between quiet roads and a compact historic center. Daily life runs on Main Street cafes, farm stores and quick highway access to Worcester and Leominster.
The town center around the Town Common, the 1835 Town Hall and Pine Street, home to the Historical Society museum and Main Street spots like Emma's Cafe and The Brick. Compact village center. ( source )
The lake area where the town's first settlers lived in the 1640s. The town maintains an easy, dog-friendly Waushacum Trail. ( source )
The railroad-era section of town named for Lt. Joel Pratt, an aide to George Washington. The railroads reached Sterling in the 1850s. ( source )
Orchard country, home to Meadowbrook Orchards and Rota Spring Farm. Rolling farmland with homes set along rural roads. ( source )
Farm land worked by the Davis family since 1846, now home to Davis Farmland and the Davis Mega Maze. Rural roads and open fields. ( source )
The north-south route toward Leominster with restaurants like Barber's Crossing North and the Black Sheep Tavern, plus quick access to I-190. ( source )
Scratch kitchen and bar downtown since 2016. Known for ceviche, mariscada and handcrafted margaritas. ( source )
Cafe, breakfast and lunch · 37 Main St, Sterling CenterSet in the former Bank Building on Main Street. Scratch soups, fresh scones and a signature turkey chili. ( source )
American, barbecue · 175 Leominster Rd (Route 12)A Worcester-born restaurant family (founded 1984) with its Sterling location on Route 12. Open seven days, with function space. ( source )
Seasonal American · Chocksett Inn, 59 Laurelwood RdThe Chocksett Inn's restaurant, open to the public, with a changing seasonal menu, cocktails, local brews and a patio. ( source )
Farm restaurant and bakery · 209 Chace Hill RdYear-round breakfast and lunch on a family farm worked since 1912. Go for apple cider donuts, apple pie and David's BBQ sauce. ( source )
Homemade ice cream · 117 Chace Hill RdFarm ice cream stand with seasonal flavors, a food menu, picnic tables and goats to feed. Farm store sells its own grass-fed beef. ( source )
Pizza and subs · 239 Worcester RdFamily-owned since 1986, with dough made fresh daily. Pizzas, subs, salads and pastas. ( source )
Tavern · 261 Leominster Rd (Route 12)Local tavern on Route 12 with the slogan "Meet me at the Sheep." ( source )
Four 18-hole layouts through the orchards and woods, open sunrise to sunset every day, with a pro shop on site. ( source )
Fridays from 3 to 6:30 pm, May to October, at 1 Park Street. ( source )
The historic green in the town center, home to the lamb statue and the original site of the town fair. ( source )
Grab an ice cream, sit at a picnic table and let the kids pet and feed the goats. ( source )
Active, family-friendly group at 1 Maple Street focused on local agriculture, community gardening and town involvement. ( source )
Independent gift shop on Main Street with handmade goods from U.S. artisans and Fair Trade makers. ( source )
Home decor, furniture and gifts at 40 Main St, with interior design services. ( source )
Garden center with plants, a stone yard, pond store and pottery, plus landscape design, delivery and installation. ( source )
Farm store and bakery with house-made preserves, heat-and-serve entrees and pies to order. ( source )
Seasonal fruits and vegetables, homemade breads and jams, and the farm's own grass-fed beef. ( source )
Easy, scenic town trail. DCR runs public programs from 25 Gates Road, including a Halloween luminary walk. ( source )
borders townThe 65 billion gallon reservoir has 37 miles of shoreline. Shore fishing in designated areas, walking and interpretive programs. No dogs, swimming or boating. ( source )
in town19 acres of forest with a marked trail and views of the Wekepeke reservoir basin and farmland on Tuttle Road. ( source )
in town19+ acres of fields, woods and a barn on Lucas Road by Stewart Pond, with trails into Leominster State Forest. ( source )
about 10 miles to the beach entranceNearest state park. Hiking, mountain biking, the Midstate Trail, rock climbing at Crow Hill Ledges and swimming at Crow Hill Pond. ( source )
about 13 miles3,000 acres around a 2,006-foot peak with 17 miles of trails and a summit road with 360 degree views. ( source )
about 12 milesFederal refuge along the Nashua River with wetlands, oxbow ponds, trails and a kayak launch. ( source )
Family farm park on land the Davis family has farmed since 1846, known for rare and endangered livestock breeds, a focus that began with three highland cattle gifted after a 1990 fire, plus the Cowabunga Splash Park and U-pick apples. Built for kids 12 and under. ( source )
Giant fall corn maze on Redstone Hill with more than 60 attractions, live entertainment and food. ( source )
Statue on the Town Common honoring the lamb of Mary Sawyer, born in Sterling in 1806. ( source )
Museum and research library at 7 Pine Street in the Sterling Center Historical District. ( source )
Historic town hall in the center of town, one of Sterling's signature landmarks. ( source )
All-volunteer agricultural fair with rides, horse, oxen and tractor pulls, livestock shows, an antique engine show and food. Roots go back to the Sterling Cattlemen's Association. ( source )
FallThe Halloween Mystery Mega Maze with trick-or-treating in the maze and dozens of attractions. ( source )
Fridays, May to OctoberWeekly market at 1 Park Street, 3 to 6:30 pm. ( source )
OctoberDCR Wachusett Reservoir interpretive program starting at 25 Gates Road. ( source )
Late summer through fallPick-your-own at Davis Farmland and Meadowbrook Orchards. ( source )
Houghton Elementary School (Grades K-4, Sterling)
MiddleChocksett Middle School (Grades 5-8, Sterling)
HighWachusett Regional High School (Holden), Montachusett Regional Technical School (regional vocational option)
Listed for reference, not ranked. Confirm school zoning for any address with the district. ( source )
I-190, Route 12, Route 62 and Route 140, with I-290 and I-495 nearby
AirportsWorcester Regional Airport, about 30 min; Boston Logan International Airport, about 75 min without traffic
Clinton: about 10 min Leominster: about 15 min Fitchburg: about 20 min Worcester: about 20 min Boston: about 75 min without trafficRyan and Megan Winslow, broker owners of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Call 386-690-5858 Email Ryan and Megan Get pre-approvedResearched and verified 2026-09-28. Businesses change; call ahead.
The typical home in Sterling is worth $593,000, 19% above the Worcester County typical value of $498,000 and 10% below the Massachusetts typical value of $662,000.
Zillow Home Value Index for Sterling, August 2026. The middle of the market for single family homes and condos.
Home values in Sterling moved +28.3% over five years and +87.3% over ten.
Median gross rent in Sterling. Useful for investors running rental numbers.
Share of occupied homes in Sterling lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Sterling.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Sterling home of $593,000:
Ryan and Megan price Sterling homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $453,000 · 15,740 residents
Area guide →Typical value $472,000 · 44,209 residents
Area guide →Typical value $639,000 · 3,597 residents
Area guide →Typical value $520,000 · 7,938 residents
Area guide →Typical value $581,000 · 8,993 residents
Area guide →Typical value $629,000 · 5,064 residents
Area guide →See the full Worcester County real estate guide or the Massachusetts real estate guide.
The Zillow Home Value Index for Sterling was $593,000 in August 2026, +1.9% over the past year.
Sterling is in Worcester County, Massachusetts.
About 8,310 people as of the 2024 Census Bureau estimate, up from 7,982 in 2020.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009 and are licensed in Florida, Massachusetts, Connecticut and Rhode Island. Call or text 386-690-5858.
Apply at www.winslowloan.com. Ryan and Megan are mortgage bankers with The Federal Savings Bank and lend in all 50 states, including FHA, VA and conventional loans.
88% of occupied homes in Sterling are owner occupied, based on the 2019 to 2023 American Community Survey.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
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The typical home in Sterling is worth $593,444 as of August 2026 in ZIP code 01564. Values moved +1.9% over the last 12 months at the middle ZIP code.
| ZIP | Typical value | 12 months | 5 years | Median sale, Mar to May 2026 | Days on market |
|---|---|---|---|---|---|
| 01564 | $593,444 | +1.9% | +28.3% | $522,500 | 22 |
Sources: Zillow Home Value Index through August 2026 and the Redfin Data Center ZIP code tracker, March to May 2026. Ask Ryan and Megan for a value for your own home.
