38 Skytop Drive, Madison, CT 06443
OFF MARKET

$917,700

Trulia Estimate
  • 3 Beds
  • 2.5 Baths
  • 2,204 sqft (on 1.47 acres)

38 Skytop Drive, Madison, CT 06443

Est. Refi. Payment $6,466/mo*
Refinance Your Home
Currently Off Market - Sold Jun 27, 2025 for $878,000

Home Value

Trulia Estimate
$918K
Since last month
Increased$7K (+0.7%)
Since last year
Increased$29K (+3.3%)
Since last sale
Increased$39K (+4.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +133% in the last 10 years
MonthEstimated value
2026
August 2026$917K
August 2026$916K
July 2026$911K
June 2026$910K
May 2026$901K
April 2026$895K
March 2026$904K
February 2026$904K
January 2026$908K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
190 Wildcat Road, Madison, CT
0.20
Single-Family Home
$1,260,444
08/07/26
3
2.5
2,451
26 Flintlock Road, Madison, CT
0.15
Single-Family Home
$775,000
02/09/26
5
3
2,904
6 Yankee Peddler Path, Madison, CT
0.30
Single-Family Home
$660,000
06/12/26
4
2
2,642
107 Horse Pond Road, Madison, CT
0.11
Single-Family Home
$430,000
06/12/26
3
2
864
125 Wildcat Road, Madison, CT
0.34
Single-Family Home
$1,000,000
07/07/26
4
2.5
3,909
221 Duck Hole Road, Madison, CT
0.49
Single-Family Home
$600,000
07/17/26
3
3
2,068
241 Hunters Trail, Madison, CT
0.29
Single-Family Home
$850,000
10/06/25
4
3
3,464
40 Puritan Lane, Madison, CT
0.50
Single-Family Home
$625,000
03/02/26
4
3.5
2,656
71 Madison Springs Drive, Madison, CT
0.61
Single-Family Home
$975,000
12/17/25
3
2.5
3,333

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
107 Horse Pond Road, Madison, CT 06443
0.11
$430,000
3
2
864
Recently Sold
137 Horse Pond Road, Madison, CT 06443
0.12
$893,800
4
3
3,509
Off Market
99 Horse Pond Road, Madison, CT 06443
0.12
$579,400
3
2
1,956
Off Market
29 Flintlock Road, Madison, CT 06443
0.14
$740,900
4
1.5
2,458
Off Market
26 Flintlock Road, Madison, CT 06443
0.15
$775,000
5
3
2,904
Recently Sold
142 Horse Pond Road, Madison, CT 06443
0.19
$883,300
4
2.5
3,420
Off Market
190 Wildcat Road, Madison, CT 06443
0.20
$1,260,444
3
2.5
2,451
Recently Sold
94 Sportsman Hill Road, Madison, CT 06443
0.18
$770,000
5
3.5
3,892
Off Market
92 Sportsman Hill Road, Madison, CT 06443
0.20
$626,600
4
2.5
1,902
Off Market
128 Horse Pond Road, Madison, CT 06443
0.24
$891,100
3
2.5
2,578
Off Market
252 Hunters Trail, Madison, CT 06443
0.25
$1,129,200
3
3.5
4,186
Off Market

Local Information

  • Map ViewExplore the area around 38 Skytop Drive.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1972
1.47 acre lot
2,204 sqft
$416/sqft
2 Car Garage

About this House

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!
38 Skytop Drive, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,204 sqft single-family home built in 1972. It last sold for $878,000 on Jun 27, 2025 (1% above the $869,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $917,700, with a rent estimate of $4,197/month.
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

Home Details for 38 Skytop Drive

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $869,900
Status Change & Dates
Off Market Date: Mon Jun 02 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: Madison
School Information
Elementary School: Per Board of EdHigh School: Per Board of Ed

Building

Building Area
Building Area: 2204 Square Feet

HOA

No HOA

Lot Information

Lot Area: 1.47 Acres

Miscellaneous

BasementMls Number: 24099432Attic: Access Via HatchAbove Grade Unfinished Area: 2204

Price and Tax history

DateEventPrice
Jun 27, 2025
Source: Smart MLS #24099432
Sold
$878,000
Jun 22, 2025
Source: Smart MLS #24099432
Pending
$869,900
May 29, 2025
Source: Smart MLS #24099432
Listed For Sale
$869,900
Dec 17, 2024
Source: N/A
Sold
$565,000
Sep 30, 2005
Source: Smart MLS #M9088260
Sold
$570,000

Market trends in Madison

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$710K
$53.67KMoM
Sale-to-List Price
101.6%
0.9%MoM
Price per sq ft
$334
$7MoM
Available listings
63
8MoM

Around this home

What Locals Say about Madison

At least 57 Trulia users voted on each feature.

  • 92 % Say car is needed

  • 91 % Say parking is easy

  • 90 % 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.
  • Nancy Bussiere
    "My commute to work is under 15mins. I love the easy access to highways. There is public transportation available but I haven’t used it as of yet"
    0
    Flag
  • Ginavan1
    "Safe,beautiful and family oriented. Beach and hiking places nearby. Great schools and town and local sport leagues for the kids."
    0
    Flag
  • Ginavan1
    "Good schools . Neighbors are nice and welcoming. Good sense of community. Clean, safe and great outdoors."
    0
    Flag
  • Jv4450
    "I’m just trying my luck with this and it doesn’t look too great for the job and the way the company looks I just have no confidence "
    0
    Flag
  • Trulia User
    "I’ve lived here for 30 years. Home prices continue to go up with the NYC families inching this way causing taxes to get out of control. "
    1
    Flag
  • Diana
    "I see people walking dogs but there is no dog park like in neighboring towns. However, there are many walking trails that you can take your leashed dog to walk in."
    4
    Flag
  • Elizabeth L.
    "Great neighborhood. Great schools. Beautiful town. Great library. Great beaches. New England vibe. Shoreline East train takes you to new Haven with direct connection to NYC. "
    2
    Flag
  • Cassidy W.
    "Great place. Been here for 23 years, wouldn’t change a thing. Very small town. Not a lot of commercial business in Madison, close by in Guilford, very local business oriented. "
    1
    Flag
  • Diana
    "People seem friendly enough but aren’t nosy neighbors. I think it would be fairly easy for young families to socially connect."
    2
    Flag
  • Jcimino5
    "Nice community with good school system and organized sports teams. Nice beach and walking trails. Can get a bit crowded in the summer."
    2
    Flag
  • Mike H.
    "A wonderful seaside community. Colonial New England meets the beach. Great Resaurant’s and small businesses. "
    0
    Flag
  • Junedday1
    "I've lived in this neighborhood for 9 years and love it. Great neighbors, quite, well-maintained and very safe."
    3
    Flag
  • Bob B
    "Great community. Families partipate in local activities. Safe town. Beautiful town beach properties. Great local shopping and restaurants. School system is top notch and lots of state parks close by. It’s really a picture perfect town. Lived in Madison for 42 years "
    0
    Flag
  • Robuess
    "Its the best town in America hands down. We love the local restaurants and can ride our bikes to the beach. Friendly locals who will stop and ask if you need help. Very fortunate to have lived here for 40 years!!"
    0
    Flag
  • Joy J.
    "great area to live. Good neighbors, good food. beautiful backyards. Good for animals and nature.?I would definitely suggest living here"
    0
    Flag
  • Pamelajbrown1234
    "Almost everyone has a dog, we take them everywhere. There is a dog park in town. People walk their dogs all over town and down at Hammonasette State Park. Dogs mostly seem very well trained and socialized"
    7
    Flag
  • Nicole L.
    "There is a real sense of community and people actually care about each other here. Schools are excellent and our beaches make it feel like you're always on vacation. "
    0
    Flag
  • Mike H.
    "I’ve lived here since 1990 and love it! There’s everything here, from great dining and great bookstore, coffee shops and terrific local cinema!"
    0
    Flag
  • David F.
    "Great for young families!"
    0
    Flag
  • Robert S.
    "We have lived in Madison for 15 years. This is a great neighborhood with only 12 houses. It is quiet and private as well as being a friendly and considerate group of folks. Mix of retierees and families with close proximity to many local amenities."
    0
    Flag

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Frequently asked questions about 38 Skytop Drive

  • What is 38 Skytop Drive estimated to be worth?
    Trulia's estimated value for 38 Skytop Drive in Madison, CT is $917,700.
  • What is the price history for 38 Skytop Drive?
    38 Skytop Drive in Madison, CT last sold for $878,000 in June 2025.
  • Is Madison a buyer's or seller's market?
    Madison is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Madison?
    The median sale price in Madison is $710K. That is down $53.67K from the prior month.
  • How big is the lot at 38 Skytop Drive?
    The lot at 38 Skytop Drive in Madison, CT is about 1.5 acres.
  • Does 38 Skytop Drive have a garage?
    Yes, 38 Skytop Drive in Madison, CT has an attached garage.

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