# 16 Deepwood Drive, Cheshire, CT 06410 > **TL;DR:** 3bd/2ba single family, $465,000 ($297/sqft), built 1955, 1,566 sqft. > A/C, 2-car garage. Est. $2,487/mo. Listed 140 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $465,000 | | Price/sqft | $297 | | Bedrooms | 3 | | Bathrooms | 2 full | | Square Feet | 1,566 | | Year Built | 1955 | | Lot Size | 18,295 sqft (0.42 acres) | | Garage | 2-car | | Property Type | Single Family (Other) | | Status | Active | | Days on Market | 140 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,351 | | Estimated Insurance | $136 | | **Total** | **$2,487** | ## Nearby Schools - **Elementary:** Per Board of Ed - **High:** Cheshire ## Key Amenities - A/C - 2-car garage ## Property Highlights - Built in 1955 - 0.42 acre lot ## Description ### Agent Description Seller is offering first year mortgage rate buydown, currently saving $246 per month on this stunningly remodeled 3 BR, 2 bath Gambrel Cape and its spacious oversized garage! Updated from top to bottom, this is a rare move in ready gem where every detail has been done for you. Enjoy an unbeatable location near dining, shops and the 11 mile Farmington Canal Heritage Trail! The beautifully renovated exterior offers new vertical board and batten siding, a brand-new shingle roof, and a level, private backyard shaded by mature trees. The property boasts a massive garage with a spacious loft-ideal for a home studio, workshop, or gym. Step inside to find a sun-drenched floor plan showcasing gleaming hardwood floors and brand-new luxury laminate. The main level offers ultimate flexibility with a primary bedroom that can easily double as a home office. The fully renovated kitchen features sleek quartz countertops and stainless steel appliances, opening directly to a durable composite deck for seamless outdoor entertaining. The dining area is accented by beautiful, custom built-ins. This home has been upgraded for maximum efficiency and peace of mind with its new energy-efficient windows and doors, new recessed lighting, a new 100-amp electrical panel, natural gas heat, a brand-new hot water heater, city water/sewer connections and underground utilities. Enjoy a fantastic community investing $166M in top-tier education with 2 brand new elementary schools! Agent related. ## Location - **Address:** 16 Deepwood Drive, Cheshire, CT 06410 - **County:** New Haven - **Coordinates:** 41.508641, -72.914502 - **Google Maps:** https://www.google.com/maps?q=41.508641,-72.914502 ## Virtual Tour & Media - **Video Tour:** https://unbranded.visithome.ai/F2pRKGrkVzeCG4BFfKKQkz?mu=ft ## Listing Agent - **Name:** Lisa Rollins - **Brokerage:** Page Taft~Christie's IRE - **Broker Phone:** (203) 623-4078 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/16-Deepwood-Dr_Cheshire_CT_06410_M39423-83178?f=listhub&s=CTMLS&m=24182948&c=propsimple) ## Photos ![16 Deepwood Drive - Photo 1](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f983661119r.jpg) ![16 Deepwood Drive - Photo 2](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f4048312923r.jpg) ![16 Deepwood Drive - Photo 3](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3359845528r.jpg) ![16 Deepwood Drive - Photo 4](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3437088044r.jpg) ![16 Deepwood Drive - Photo 5](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f786332912r.jpg) ![16 Deepwood Drive - Photo 6](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f1016868071r.jpg) ![16 Deepwood Drive - Photo 7](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f924836842r.jpg) ![16 Deepwood Drive - Photo 8](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3707414028r.jpg) ![16 Deepwood Drive - Photo 9](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f1430123568r.jpg) ![16 Deepwood Drive - Photo 10](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3133751433r.jpg) ![16 Deepwood Drive - Photo 11](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f536866769r.jpg) ![16 Deepwood Drive - Photo 12](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3798890313r.jpg) ![16 Deepwood Drive - Photo 13](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f1561905487r.jpg) ![16 Deepwood Drive - Photo 14](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2239530987r.jpg) ![16 Deepwood Drive - Photo 15](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2518345425r.jpg) ![16 Deepwood Drive - Photo 16](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2845977116r.jpg) ![16 Deepwood Drive - Photo 17](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3355170354r.jpg) ![16 Deepwood Drive - Photo 18](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f658381314r.jpg) ![16 Deepwood Drive - Photo 19](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f207570391r.jpg) ![16 Deepwood Drive - Photo 20](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f4262727649r.jpg) ![16 Deepwood Drive - Photo 21](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2198256795r.jpg) ![16 Deepwood Drive - Photo 22](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2920425381r.jpg) ![16 Deepwood Drive - Photo 23](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3470111748r.jpg) ![16 Deepwood Drive - Photo 24](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f1576311572r.jpg) ![16 Deepwood Drive - Photo 25](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f114891119r.jpg) ![16 Deepwood Drive - Photo 26](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2943038860r.jpg) ![16 Deepwood Drive - Photo 27](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f783157842r.jpg) ![16 Deepwood Drive - Photo 28](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3180559280r.jpg) ![16 Deepwood Drive - Photo 29](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f1328348705r.jpg) ![16 Deepwood Drive - Photo 30](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3010668828r.jpg) ![16 Deepwood Drive - Photo 31](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f1069947636r.jpg) ![16 Deepwood Drive - Photo 32](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3137145706r.jpg) ![16 Deepwood Drive - Photo 33](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2232087967r.jpg) ![16 Deepwood Drive - Photo 34](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f445742098r.jpg) ![16 Deepwood Drive - Photo 35](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f3869737919r.jpg) ![16 Deepwood Drive - Photo 36](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f2975013656r.jpg) ![16 Deepwood Drive - Photo 37](http://lh.rdcpix.com/850ff0fc12320d61cf06a739f61f8513l-f242441368r.jpg) --- **MLS#:** 24182948 | **Updated:** 2026-10-31 **Source:** listhub *Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/16-deepwood-drive-cheshire-ct-06410-6c7755f78a4246b6bd99f5325aeb22f0) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/16-deepwood-drive-cheshire-ct-06410-6c7755f78a4246b6bd99f5325aeb22f0#listing", "url": "https://www.propertysimple.ai/listing/16-deepwood-drive-cheshire-ct-06410-6c7755f78a4246b6bd99f5325aeb22f0", "name": "16 Deepwood Drive, Cheshire, CT 06410", "description": "Seller is offering first year mortgage rate buydown, currently saving $246 per month on this stunningly remodeled 3 BR, 2 bath Gambrel Cape and its spacious oversized garage! Updated from top to bottom, this is a rare move in ready gem where every detail has been done for you. Enjoy an unbeatable location near dining, shops and the 11 mile Farmington Canal Heritage Trail! The beautifully renovated exterior offers new vertical board and batten siding, a brand-new shingle roof, and a level, private backyard shaded by mature trees. The property boasts a massive garage with a spacious loft-ideal for a home studio, workshop, or gym. Step inside to find a sun-drenched floor plan showcasing gleaming hardwood floors and brand-new luxury laminate. The main level offers ultimate flexibility with a primary bedroom that can easily double as a home office. The fully renovated kitchen features sleek quartz countertops and stainless steel appliances, opening directly to a durable composite deck for seamless outdoor entertaining. The dining area is accented by beautiful, custom built-ins. This home has been upgraded for maximum efficiency and peace of mind with its new energy-efficient windows and doors, new recessed lighting, a new 100-amp electrical panel, natural gas heat, a brand-new hot water heater, city water/sewer connections and underground utilities. Enjoy a fantastic community investing $166M in top-tier education with 2 brand new elementary schools! 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