Rockwood Meadows
Upton, Massachusetts · Worcester County
Rockwood Meadows is a 58-home age-restricted 55+ community at 2 Rockwood Lane in Upton, Massachusetts, built by Lobisser Building Corp. starting around 2016. The community mixes detached single-family and attached homes, nestled against Peppercorn Hill with a network of walking trails, open space, and unspoiled woodlands surrounding a community center. Homes range from 1,743 to 2,423 square feet with two bedrooms, two-to-two-and-a-half bathrooms, and attached two-car garages, featuring gas fireplaces, stainless steel appliances, custom cherry cabinetry, and hardwood floors.
Last researched 2026-09-17
- Price positioning
- Not publicly confirmed
- HOA
- Historical listing data from 2018 showed roughly $303/month; current figure not publicly confirmed
- Community size
- 58 single-family and attached homes
- Home types
- detached, attached
- Builder
- Lobisser Building Corp.
- Age policy
- Legally age-restricted 55+ -- listed under activeadultliving.com's dedicated Massachusetts '55-plus-communities' directory category, which is treated as a genuine confirming source for legal age restriction
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Overview
Independent Assessment
Rockwood Meadows is a relatively newer (2016-era) small community with reasonably consistent facts across independent sources -- Seniorly, 55places, and activeadultliving.com all describe the same 58-home count, Lobisser Building Corp. builder, and general setting against Peppercorn Hill. Current pricing for available units was not confirmed, and only a single, dated (2018) HOA fee figure of roughly $303/month from a historical listing was found, which is not a reliable guide to current costs. Whether Rockwood Meadows is now fully built out or whether any construction phases remain active could not be independently confirmed.
Who May Find This Community Appealing
Buyers who want a mix of single-family and attached home options within one small, nature-oriented Worcester County community -- with genuine walking trails and woodland open space rather than just a landscaped courtyard -- will find Rockwood Meadows appealing. Its Upton location suits buyers who want a quieter, more rural Central Massachusetts setting while still being within a reasonable drive of Worcester and the Boston area.
Homes & Prices
Homes, Builders & Development History
Lobisser Building Corp. began construction at Rockwood Meadows around 2016, building a planned 58 single-family and attached homes at 2 Rockwood Lane in Upton. Homes range from 1,743 to 2,423 square feet with two bedrooms, two-to-two-and-a-half bathrooms, and attached two-car garages, and feature gas fireplaces, stainless steel appliances, custom-built cherry cabinets, hardwood floors, and landscaped yards with sprinkler systems.
Current Pricing & Market Positioning
No publicly confirmed current price range was located in the sources reviewed for Rockwood Meadows. Buyers should request current pricing directly from a local agent experienced with Upton-area 55+ resale communities.
New Construction vs. Resale Considerations
No evidence of an active, ongoing new-construction sales office at Rockwood Meadows was found, and the community is treated as an established, resale-oriented product roughly a decade after construction began; buyers should confirm current availability and whether any builder inventory remains directly with a local agent.
Want current listings in this community?
Pricing changes fast. A connected local agent can send current active listings and recent comparable sales.
Fees
HOA Fees, Capital Contributions & Recurring Costs
The only HOA fee data point found was a dated 2018 listing showing roughly $303/month, described as covering sewer, insurance, road maintenance, grounds maintenance, snow removal, and trash. This figure is several years old and should not be relied upon for current budgeting; buyers should request the current fee schedule directly from the condominium association or a local agent.
Taxes, Insurance & Special Assessments
Homes at Rockwood Meadows are subject to the Town of Upton's property tax administration. A current effective property tax rate, the association's master insurance coverage, and any special-assessment history were not independently confirmed; buyers should confirm exact current figures with the Upton Assessor's Office and request the association's current financials before purchasing.
Amenities
Community Layout & Lifestyle
Rockwood Meadows' 58 single-family and attached homes are arranged in a tranquil setting abutting Peppercorn Hill, with open spaces, walking trails, and unspoiled woodlands woven through the community and a community center serving as the shared gathering space. The HOA handles building and common-area landscaping maintenance, giving residents a genuinely maintenance-free lifestyle set against a more rural, nature-forward backdrop than many of the region's more suburban 55+ developments.
Location
Shopping, Healthcare & Airport Access
Rockwood Meadows is located at 2 Rockwood Lane, Upton, MA 01568. Upton is a smaller, more rural Worcester County town; Boston is roughly a 45-minute drive away, with Boston Logan International Airport accessible for long-distance travel, and Worcester is about 25 miles away. Buyers should confirm current drive times to specific medical facilities and shopping from this exact address.
Restrictions
Age Qualification & Material Ownership Restrictions
Rockwood Meadows is listed under activeadultliving.com's dedicated Massachusetts '55-plus-communities' directory category, which is treated as a genuine confirming source for legal age restriction given that directory's explicit, dedicated age-restricted-community scoping. Rockwood Meadows' recorded condominium declaration or master deed language was not independently reviewed. Buyers should request the current recorded declaration and confirm the association's specific age-verification procedure directly before purchasing.
Pros & Tradeoffs
Tradeoffs & Limitations
Nothing in the sources reviewed confirmed current pricing for available units at Rockwood Meadows, and the only HOA fee figure found (roughly $303/month) is a dated 2018 listing data point that may not reflect current costs. Upton is a more rural, less commercially developed town than some other Worcester County 55+ locations, which may be a tradeoff for buyers who want walkable access to shopping and services. Buyers should request the condominium association's current budget, fee schedule, and reserve study directly before purchasing.
Comparison With Nearby Communities
Within Worcester County's tracked 55+ cluster, Rockwood Meadows is one of the smaller communities at 58 homes, comparable in scale to Northborough's 41-home Bigelow Farm but offering a mix of detached single-family and attached homes rather than Bigelow Farm's townhome-only format. Unlike Holden's two condominium-style communities (Seasons at Salisbury and Village at Westminster Place), Rockwood Meadows is set in a more rural, woodland-adjacent Upton location.
Listings
Current Listings
A connected local agent can provide current available Rockwood Meadows listings.
FAQs
Questions Buyers Should Verify
- Current pricing for available units at Rockwood Meadows
- Current HOA/condominium-association fee (the $303/month figure found is from a 2018 listing and likely stale)
- The exact recorded condominium declaration language establishing the 55+ age restriction and verification procedure
- Whether Rockwood Meadows is now fully built out or whether any construction phases remain active
- Current property tax rate for Upton
- How many homes are at Rockwood Meadows?
- 58 single-family and attached homes, built by Lobisser Building Corp. starting around 2016 at 2 Rockwood Lane in Upton, MA.
- What size are the homes at Rockwood Meadows?
- Homes range from 1,743 to 2,423 square feet, typically 2 bedrooms with 2 to 2.5 bathrooms and attached 2-car garages.
- Is Rockwood Meadows a legally age-restricted 55+ community?
- Yes. Rockwood Meadows is listed under activeadultliving.com's dedicated Massachusetts 55-plus-communities directory category. The recorded condominium declaration was not independently reviewed, so buyers should confirm the exact legal restriction and verification procedure directly with the association.
- What is the current HOA fee at Rockwood Meadows?
- Only a dated 2018 listing figure of roughly $303/month was found, covering sewer, insurance, road maintenance, grounds maintenance, snow removal, and trash. Buyers should request the current fee schedule directly.
Sources
- Rockwood Meadows - Upton MA 55+ Retirement Communities | activeadultliving.com — accessed 2026-09-17
- Rockwood Meadows | Upton, Massachusetts 55+ Retirement Community & Homes for Sale | 55places — accessed 2026-09-17
- 21 Rockwood Ln, Unit 21, Upton, MA 01568 | Compass — accessed 2026-09-17
- Upton, Massachusetts | Wikipedia — accessed 2026-09-17
Interested in Rockwood Meadows?
Connect with a local agent who understands the community, current homes, and buying process.
Nearby and similar communities
Bigelow Farm
Northborough, MA · Worcester County
Attached / townhome
Private community center
The Seasons at Salisbury
Holden, MA · Worcester County
Attached / townhome · Condo
Price: Started from the low $400,000s; current resale pricing not publicly confirmed
Del Webb Chauncy Lake
Westborough, MA · Worcester County
Attached / townhome · Condo
Outdoor swimming pool · Bocce ball courts · Tennis courts
Village at Westminster Place
Holden, MA · Worcester County
Single-family · Attached / townhome
Price: Marketed from the high $300,000s when new sections opened; current resale pricing not publicly confirmed
Full basements · Walking and biking trails · Setting on Chaffin Pond