16 Shepherds Trl
Madison, CT 06443
5 Beds
3.5 Baths
3,849 sqft (on 2.23 acres)
5 Beds
3.5 Baths
3,849 sqft
(on 2.23 acres)
Local Information
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Description
Nestled on a beautifully wooded lot, this extraordinary home borders conservation land trust for extensive privacy within a neighborhood environment. You will be captivated the moment you turn into the private drive! With soaring cath ceilings, skylights, floor-to-ceiling windows and an updated open floor plan, and 3 car attached garage, this totally renovated Colonial blends functionality with Contemporary flair. The LR with it's large FPL opens to a formal DR overlooking the backyard. The spacious eat-in KIT is a cook's dream, boasting a ZLINE range, pot-filler, huge center island, and view of the second FPL which is see-thru to Sun Rm. Two more light-filled bonus rooms off the KIT overlook a new multi-tiered composite deck where you can entertain or relax in the sun among the serene forest backdrop. A huge laundry rm offers a soaking sink and tremendous storage. The gorgeous HW floors have an intricate herringbone pattern on the second floor. Among the five bedrooms upstairs, there is an oversized MBR Suite featuring two heated walk-in closets, a sitting area, and a designer full bath with oversized walk-in shower and soaker tub. Two BR share a Jack and Jill Bth, with the final full Bth servicing the remaining BRs. The finished LL has a walk out French Door and a high-performance sealed floor and ample storage. This home provides easy access to the Shepherds Trailhead for hiking, a short hop to shopping, and is only a three-minute drive to Chatfield Hollow State Park.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info
Home Details for 16 Shepherds Trl
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Heating & Cooling Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 12 |
Appliances & Utilities DishwasherMicrowaveRefrigerator |
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Exterior Home Features Roof: AsphaltExterior: Wood |
Parking & Garage GarageParking Spaces: 3Parking: Garage Attached |
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Year Built Year Built: 1980 |
Property Type / Style Property Type: Single Family HomeArchitecture: Contemporary |
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Lot Area: 2.23 acres |
Price History for 16 Shepherds Trl
| Date | Price | Event | Source |
|---|---|---|---|
| 04/09/2021 | $765,000 | Sold | Smart MLS #170369539 |
| 02/13/2021 | $749,000 | Listed For Sale | Agent Provided |
| 09/30/2019 | $645,000 | Sold | Smart MLS #170216341 |
| 08/12/2019 | $649,900 | PriceChange | Agent Provided |
| 07/15/2019 | $669,000 | Listed For Sale | Agent Provided |
| 11/19/2018 | $307,000 | Sold | Smart MLS #170067632 |
| 10/09/2018 | $350,100 | PriceChange | Agent Provided |
| 08/24/2018 | $368,500 | PriceChange | Agent Provided |
| 07/20/2018 | $387,800 | PriceChange | Agent Provided |
| 06/21/2018 | $408,200 | PriceChange | Agent Provided |
| 05/26/2018 | $429,600 | PriceChange | Agent Provided |
| 04/21/2018 | $452,200 | PriceChange | Agent Provided |
| 04/05/2018 | $475,900 | PriceChange | Agent Provided |
| 04/02/2018 | $500,900 | PriceChange | Agent Provided |
| 03/27/2018 | $475,900 | PriceChange | Agent Provided |
| 02/23/2018 | $500,900 | PriceChange | Agent Provided |
| 01/26/2018 | $527,200 | PriceChange | Agent Provided |
| 12/29/2017 | $554,900 | PriceChange | Agent Provided |
| 12/11/2017 | $584,100 | PriceChange | Agent Provided |
| 12/09/2017 | $614,800 | PriceChange | Agent Provided |
| 12/02/2017 | $584,100 | PriceChange | Agent Provided |
| 11/01/2017 | $614,800 | PriceChange | Agent Provided |
| 09/28/2017 | $651,900 | Listed For Sale | Agent Provided |
| 11/15/2012 | $599,000 | ListingRemoved | Agent Provided |
| 06/24/2012 | $599,000 | Listed For Sale | Agent Provided |
| 01/17/1997 | $352,962 | Sold | N/A |
| 05/16/1995 | $320,000 | Sold | N/A |
| 07/08/1992 | $291,500 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $13,451 |
| Assessment | $599,700 |
Home facts updated by county records
Comparable Sales for 16 Shepherds Trl
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.14 | Single-Family Home | $775,000 | 01/16/26 | 4 | 2.5 | 4,879 | |
0.22 | Single-Family Home | $690,000 | 10/24/25 | 4 | 2.5 | 3,999 | |
0.51 | Single-Family Home | $705,000 | 05/28/26 | 4 | 2.5 | 3,212 | |
0.36 | Single-Family Home | $618,660 | 12/30/25 | 3 | 2.5 | 2,793 | |
0.86 | Single-Family Home | $860,000 | 03/02/26 | 4 | 3 | 3,517 | |
0.84 | Single-Family Home | $1,220,000 | 06/24/25 | 4 | 3.5 | 4,442 | |
1.02 | Single-Family Home | $900,000 | 04/02/26 | 4 | 3.5 | 3,982 | |
0.85 | Single-Family Home | $637,500 | 06/23/25 | 3 | 2.5 | 1,747 | |
1.01 | Single-Family Home | $960,000 | 08/29/25 | 3 | 2.5 | 2,558 | |
1.14 | Single-Family Home | $650,000 | 07/28/25 | 4 | 2.5 | 2,511 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETSunset Creek Realty, LLC
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SOLDDEC 30, 2025William Pitt Sotheby's Int'l
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Assigned Schools
These are the assigned schools for 16 Shepherds Trl.
- Daniel Hand High School
- 9-12
- Public
- 828 Students
10/10GreatSchools RatingParent Rating AverageI feel very unsafe when in the presence of many school administrators. I wouldn’t wish the experience I’ve had here on my worst enemy. I feel constantly harassed by some teachers but more namely the school administrators, including the Vice principal. Every day I try to come in with a positive attitude about this place, but someone has to ruin it. There are however some teachers that do a great job teaching and making everyone feel safe, but the negatives outweigh this way too much.Student Review1y ago - Kathleen H. Ryerson Elementary School
- K-3
- Public
- 316 Students
10/10GreatSchools RatingParent Rating AverageThis school is an absolute gem. My kids are greeted by name, helped out of the car and warmly escorted into the building. The principal loves her job, and it shows. The teachers make learning fun and curriculum is academically on point.. The culture is one of kindness and you can feel the love on site and at community events. We came from a huge school, so moving to this tight-knit but super welcoming community has been a dream come true!Parent Review4y ago - Dr. Robert H. Brown Middle School
- 4-5
- Public
- 354 Students
9/10GreatSchools RatingParent Rating AverageThe school is great. The teachers help you as much as they can and they want you to have as much fun as possible. At the end of every trimester some related arts classes let parents come to the school to watch there kid (in Xylorythems, Theater arts, Music and Art.) There is some bullying but you can quicky report if someone is bullying you and they will quickly handle it.Student Review2y ago - Walter C. Polson Upper Middle School
- 6-8
- Public
- 520 Students
9/10GreatSchools RatingParent Rating AverageMy kids are currently attending Polson MS and are receiving an excellent education that is preparing them for high school and beyond. The course work is challenging and homework is not lacking, however, the teachers are readily available to the students for extra help before and after school. But even with all the hard work the school has great spirit and the kids have fun either in sports, theater, music or what ever their area of interest is. The schools drew us to Madison and the location has kept us! GREAT TOWN! I believe the parent involvement in the school system is a primary driver for why the school system is so successful.Parent Review14y ago 
Check out schools near 16 Shepherds Trl.
What Locals Say about Madison
At least 57 Trulia users voted on each feature.
92 % Say car is needed
91 % Say parking is easy
89 % Say yards are well-kept
89 % Say it's dog friendly
88 % Say there's wildlife
85 % Say there's holiday spirit
78 % Say people would walk alone at night
74 % Say it's quiet
66 % Say neighbors are friendly
63 % Say they plan to stay for at least 5 years
62 % Say kids play outside
39 % Say there are community events
31 % Say streets are well-lit
29 % Say it's walkable to grocery stores
26 % Say it's walkable to restaurants
12 % Say there are sidewalks
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 16 Shepherds Trl
- 1.92 ACRESColdwell Banker Realty
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Off Market Homes Near 16 Shepherds Trl
SOLDMAY 29, 2026LPT Realty
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SOLDMAY 29, 2026Coldwell Banker Realty
SOLDMAY 28, 2026Exceptional Real Estate LLC
SOLDMAY 13, 2026Vanguard Private Client Grp
SOLDMAY 12, 2026Coldwell Banker Realty
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Homes for rent near 16 Shepherds Trl
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16 Shepherds Trl, Madison, CT 06443 is a 5 bedroom, 4 bathroom, 3,849 sqft single-family home built in 1980. This property is not currently available for sale. 16 Shepherds Trl was last sold on Apr 9, 2021 for $765,000. The current Trulia Estimate for 16 Shepherds Trl is $1,044,900.