We don't do much business in Fairfield County and the contractors we do deal with are definitely on the expensive side. $450/mo. for an acre isn't too bad. We pay $75/week for 1/2+ acre of turf and $40/mow & blow for a 1/4 acre (at least for a legit, insured one) is pretty much the going rate in central CT and things are a helluva lot more expensive down there. The snow removal is on the steep side, though (unless it's a corner lot), and storm cleanup really depends on the extent but seems to be on the high side.

If the guy has been reliable I'd let him know you're shopping around. In the current climate most guys will do whatever they have to to keep a customer.

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1980 300TD-China Blue/Blue MBTex-2nd Owner, 107K (Alt Blau) OBK #15
'06 Chevy Tahoe Z71 (for the wife & 4 kids, current mule) '03 Honda Odyssey (son #1's ride, reluctantly) '99 GMC Suburban (255K+ miles, semi-retired mule) 21' SeaRay Seville (summer escape pod)