20 Crestview Dr
Madison, CT 06443
6 Beds
5 Baths
5,210 sqft (on 1.39 acres)
$1,303,400
as of Jun 6, 2026
$1,303,400
as of Jun 6, 2026
6 Beds
5 Baths
5,210 sqft
(on 1.39 acres)
Local Information
© Google
-- mins to
Description
The best of "All" worlds ! Beautifully maintained & updated Colonial PLUS fully equip one bedroom in-law apartment with private entrance PLUS newly built living space in walk out lower level that includes custom bathroom, spacious bedroom, living room & tons of storage.
First floor flow is perfect for today's lifestyle. Spacious & open kitchen with a bright & sunny family room that overlooks your private back yard. Huge multi-layer deck with hot tub will be the hit of all your outdoor gatherings.
Second floor includes three generous bedrooms, and a master bedroom suite with a walk in closet that you'll get lost in!
Bonus room above garage perfect for office, fitness center or just your private retreat.
This home has it all and way too many updates to list but just a few benefits you'll enjoy will be propane cooking & fireplace, quartz kitchen countertop, freshly painted in-law apartment, hardwood floors throughout first floor of main home, multi zone heating/cooling, and so much more. Absolutely move in condition! All of this in the perfect location close to town with over an acre of land in a sought after neighborhood.
First floor flow is perfect for today's lifestyle. Spacious & open kitchen with a bright & sunny family room that overlooks your private back yard. Huge multi-layer deck with hot tub will be the hit of all your outdoor gatherings.
Second floor includes three generous bedrooms, and a master bedroom suite with a walk in closet that you'll get lost in!
Bonus room above garage perfect for office, fitness center or just your private retreat.
This home has it all and way too many updates to list but just a few benefits you'll enjoy will be propane cooking & fireplace, quartz kitchen countertop, freshly painted in-law apartment, hardwood floors throughout first floor of main home, multi zone heating/cooling, and so much more. Absolutely move in condition! All of this in the perfect location close to town with over an acre of land in a sought after neighborhood.
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
Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 20 Crestview Dr
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Heating & Cooling Heating: Other, Oil, Propane ButaneAir ConditioningCooling System: CentralHeating Fuel: Other |
Interior Details In-law unitNumber of Rooms: 15Types of Rooms: Dining Room, Family Room, Office, Sun Room |
Appliances & Utilities DishwasherMicrowaveRefrigerator |
Fireplace & Spa Hot Tub or Spa |
Levels, Entrance, & Accessibility Floors: Other |
Security Security System |
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Exterior Home Features Roof: Asphalt, Shake ShingleDeckExterior: VinylPatio |
Parking & Garage GarageParking Spaces: 2Parking: Garage Attached |
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Year Built Year Built: 1996 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Lot Area: 1.39 acres |
Price History for 20 Crestview Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 06/10/2021 | $800,000 | Sold | Smart MLS #170383345 |
| 03/29/2021 | $800,000 | Pending | Real Living Real Estate #170383345 |
| 03/29/2021 | $800,000 | Contingent | Smart MLS #170383345 |
| 03/26/2021 | $800,000 | Listed For Sale | Smart MLS #170383345 |
| 09/14/2018 | $582,000 | Sold | Smart MLS #170090269 |
| 08/17/2018 | $609,900 | Pending | Agent Provided |
| 06/13/2018 | $609,900 | PriceChange | Agent Provided |
| 05/17/2018 | $625,000 | PriceChange | Agent Provided |
| 04/11/2018 | $639,900 | PriceChange | Agent Provided |
| 02/21/2018 | $659,900 | PriceChange | Agent Provided |
| 05/27/2017 | $679,900 | PriceChange | Agent Provided |
| 03/22/2017 | $699,900 | Listed For Sale | Agent Provided |
| 03/24/2016 | $659,000 | ListingRemoved | Agent Provided |
| 10/27/2015 | $659,000 | Pending | Agent Provided |
| 10/20/2015 | $659,000 | Listed For Sale | Agent Provided |
| 09/14/2015 | $649,900 | ListingRemoved | Agent Provided |
| 08/04/2015 | $649,900 | Listed For Sale | Agent Provided |
| 05/15/2015 | $649,500 | Sold | Smart MLS #N10022770 |
| 04/07/2015 | $659,000 | Pending | Agent Provided |
| 03/20/2015 | $659,000 | PriceChange | Agent Provided |
| 10/31/2014 | $649,900 | PriceChange | Agent Provided |
| 07/22/2014 | $696,500 | PriceChange | Agent Provided |
| 05/21/2014 | $669,000 | PriceChange | Agent Provided |
| 05/09/2014 | $699,000 | Listed For Sale | Agent Provided |
| 09/18/2008 | $799,000 | ListingRemoved | Agent Provided |
| 12/15/1993 | $359,000 | Sold | N/A |
Market trends in Madison
Last updated April 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
73 19MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $15,461 |
| Assessment | $689,300 |
Home facts updated by county records
Comparable Sales for 20 Crestview Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.26 | Single-Family Home | $1,325,000 | 03/29/26 | 5 | 4.5 | 4,760 | |
0.28 | Single-Family Home | $1,675,000 | 05/01/26 | 5 | 4.5 | 5,575 | |
0.58 | Single-Family Home | $900,000 | 04/02/26 | 4 | 3.5 | 3,982 | |
0.26 | Single-Family Home | $650,000 | 07/28/25 | 4 | 2.5 | 2,511 | |
0.55 | Single-Family Home | $699,000 | 12/19/25 | 4 | 2.5 | 2,882 | |
0.60 | Single-Family Home | $770,000 | 02/18/26 | 4 | 2.5 | 2,797 | |
0.77 | Single-Family Home | $860,000 | 03/02/26 | 4 | 3 | 3,517 | |
0.61 | Single-Family Home | $715,000 | 06/18/25 | 4 | 2.5 | 1,986 | |
0.83 | Single-Family Home | $725,000 | 10/29/25 | 3 | 3.5 | 3,933 | |
0.65 | Single-Family Home | $1,200,000 | 08/15/25 | 4 | 2.5 | 4,437 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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Assigned Schools
These are the assigned schools for 20 Crestview Dr.
- 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 20 Crestview Dr.
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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20 Crestview Dr, Madison, CT 06443 is a 6 bedroom, 6 bathroom, 5,210 sqft single-family home built in 1996. This property is not currently available for sale. 20 Crestview Dr was last sold on Jun 10, 2021 for $800,000. The current Trulia Estimate for 20 Crestview Dr is $1,303,400.