38 Skytop Drive
Madison, CT 06443
3 Beds
2.5 Baths
2,204 sqft (on 1.47 acres)
3 Beds
2.5 Baths
2,204 sqft
(on 1.47 acres)
Local Information
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Description
Fall in love with this beautifully transformed 3-bedroom, 2.1-bath expanded Cape just minutes from downtown Madison and the beach. Step into a dramatic great room featuring a soaring 20+ ft ceiling, a floor-to-ceiling fireplace, and a striking light fixture-perfect for cozy evenings or stylish entertaining. The open layout flows into a dream kitchen with custom shaker cabinets, quartz countertops, upgraded stainless steel appliances, tile backsplash, and designer hardware. The slate-floored entryway and open staircase add architectural flair, leading to three spacious bedrooms upstairs, including a luxurious primary suite with a spa-like ensuite and ample closet space. The second full bath offers double sinks and elegant custom tile with champagne fixtures. A large den with a second fireplace and a private office with built-ins offer flexible living options and could also serve as a 4th bedroom. French doors from the office and a slider from the kitchen lead to a bluestone patio overlooking a serene wooded backdrop-ideal for entertaining or relaxing. A 2-car garage with new doors, openers, and epoxy floors completes the package. Located just a mile from town, under two miles from the beach, and close to I-95, this rare shoreline gem blends luxury, comfort, and convenience. Don't miss this opportunity!
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. This description is from June 27, 2025
Home Highlights
Parking
2 Car Garage
Outdoor
Porch, Patio
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 38 Skytop Drive
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Interior Details Basement: FullNumber of Rooms: 8Types of Rooms: Master Bedroom, Bedroom, Dining Room, Living Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2204 Square Feet |
Appliances & Utilities Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Water HeaterDishwasherMicrowaveRefrigerator |
Heating & Cooling Heating: Baseboard,Hot Water,OilNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Baseboard |
Fireplace & Spa Number of Fireplaces: 2Has a Fireplace |
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Exterior Home Features Roof: AsphaltPatio / Porch: Porch, PatioExterior: Stone WallFoundation: Concrete PerimeterNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 6Parking: Attached,Off Street,Driveway,Garage Door Opener,Private |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 2204 Square Feet |
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Year Built Year Built: 1972 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Cape Cod,Colonial |
Building Construction Materials: ClapboardNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 1157371 |
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Price List Price: $869,900 |
Status Change & Dates Off Market Date: Mon Jun 02 2025Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: Madison |
School Information Elementary School: Per Board of EdHigh School: Per Board of Ed |
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Building Area Building Area: 2204 Square Feet |
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No HOA |
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Lot Area: 1.47 Acres |
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BasementMls Number: 24099432Attic: Access Via HatchAbove Grade Unfinished Area: 2204 |
Last check for updates: about 4 hours ago
Listed by Luke Florian, (860) 877-5800
SSG Real Estate LLC, (860) 657-4754
Bought with: Phoebe V. Finch, (617) 645-3907, William Pitt Sotheby's Int'l, (203) 245-6700
Source: Smart MLS, MLS#24099432
Price History for 38 Skytop Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 06/27/2025 | $878,000 | Sold | Smart MLS #24099432 |
| 06/22/2025 | $869,900 | Pending | Smart MLS #24099432 |
| 05/29/2025 | $869,900 | Listed For Sale | Smart MLS #24099432 |
| 12/17/2024 | $565,000 | Sold | N/A |
| 09/30/2005 | $570,000 | Sold | Smart MLS #M9088260 |
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 | $7,954 |
| Assessment | $354,600 |
Home facts updated by county records
Comparable Sales for 38 Skytop Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.14 | Single-Family Home | $711,000 | 08/21/25 | 4 | 1.5 | 2,458 | |
0.15 | Single-Family Home | $775,000 | 02/09/26 | 5 | 3 | 2,904 | |
0.25 | Single-Family Home | $680,000 | 07/18/25 | 4 | 3 | 3,037 | |
0.43 | Single-Family Home | $705,000 | 08/07/25 | 3 | 2 | 1,840 | |
0.18 | Single-Family Home | $739,000 | 08/22/25 | 5 | 3.5 | 3,892 | |
0.29 | Single-Family Home | $850,000 | 10/06/25 | 4 | 3 | 3,464 | |
0.37 | Single-Family Home | $690,000 | 08/13/25 | 4 | 3.5 | 3,120 | |
0.50 | Single-Family Home | $625,000 | 03/02/26 | 4 | 3.5 | 2,656 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
OFF MARKETWilliam Raveis Real Estate
OFF MARKETClayton Property Brokers L.L.C
SOLDAUG 21, 2025William Pitt Sotheby's Int'l
SOLDFEB 9, 2026DB Associates of CT, LLC
OFF MARKETWilliam Raveis Real Estate
SOLDAUG 22, 2025Dow Della Valle
OFF MARKETWilliam Raveis Real Estate
OFF MARKETWilliam Pitt Sotheby's Int'l
OFF MARKETColdwell Banker Realty
OFF MARKETBerkshire Hathaway NE Prop.
OFF MARKETWilliam Raveis Real Estate
Assigned Schools
These are the assigned schools for 38 Skytop Drive.
- J. Milton Jeffrey Elementary School
- K-3
- Public
- 362 Students
10/10GreatSchools RatingParent Rating AverageExcellent. Jeffrey school IS the place to be!Parent Review8y ago - 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 - 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 38 Skytop Drive.
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 38 Skytop Drive
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Off Market Homes Near 38 Skytop Drive
SOLDJUN 4, 2026William Pitt Sotheby's Int'l
SOLDJUN 4, 2026Berkshire Hathaway NE Prop.
SOLDJUN 1, 2026William Pitt Sotheby's Int'l
SOLDMAY 29, 2026William Raveis Real Estate
SOLDMAY 29, 2026LPT Realty
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Homes for rent near 38 Skytop Drive
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38 Skytop Drive, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,204 sqft single-family home built in 1972. This property is not currently available for sale. 38 Skytop Drive was last sold on Jun 27, 2025 for $878,000 (1% higher than the asking price of $869,900). The current Trulia Estimate for 38 Skytop Drive is $906,300.