25 Skytop Dr, Madison, CT 06443
OFF MARKET

25 Skytop Dr
Madison, CT 06443

  • 3 Beds
  • 3 Baths
  • 2,886 sqft (on 1.07 acres)

$858,200

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $5,892/mo*
Refinance Your Home

$858,200

Trulia Estimate
as of Jun 7, 2026
Est. Refi. Payment $5,892/mo*
Refinance Your Home
3 Beds
3 Baths
2,886 sqft
(on 1.07 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This very desirable cul-de-sac neighborhood is located just north of the town center and has easy access to the famous Madison beaches, shops, restaurants, and transportation (highway and commuter train.) As a 1966 reproduction of the Jonathan Murray House, built in Madison in 1690, 25 Skytop Dr. shares the features of the several rows of clapboard above the entrance which gives this Cape-style home its distinctive presentation. The home features a large center chimney with a fireplace in the large, fronttoback living room/dining room and a second fireplace in the family room located in the lower level walkout basement. The kitchen has a newer oak floor and painted cabinets. There is a cozy den with built-in bookshelves and painted wainscoting. A distinctive feature in the main level rooms is the beaded boxed corners. A feature often found in 17th and 18th-century homes. A few steps down from the kitchen are the stairs to the lower level with access to the family room and an adjacent full bath. There is access from this room to the patio. The unfinished part of the basement has great storage. There are two, two-bay garages. Upstairs, there are two very large bedrooms with a second floor full bath. At the back of the house is a nicely sized deck. The yard has mature trees and many flowering shrubs. This home is sited between Boston and NYC and only 20 minutes from New Haven. Beautifully maintained and in move-in condition, 25 Skytop Dr. is a rare find in Madison, CT.
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 only
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 25 Skytop Dr

Interior Features

Heating & Cooling
Heating: Baseboard, ElectricHeating Fuel: Baseboard
Interior Details
Number of Rooms: 6
Appliances & Utilities
Washer

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: Wood
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1966
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Lot Information

Lot Area: 1.07 acres

Price History for 25 Skytop Dr

DatePriceEventSource
12/19/2022$540,000Sold
Smart MLS #170528429
12/09/2022$549,900PendingToActiveWilliam Raveis Real Estate, Mortgage & Insurance #170528429
12/09/2022$549,900ContingentSmart MLS #170528429
11/14/2022$549,900PendingWilliam Raveis Real Estate, Mortgage & Insurance #170528429
10/20/2022$549,900Listed For SaleSmart MLS #170528429

Market trends in Madison

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
73
19MoM
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Property Tax and Assessment

Year2025
Tax$8,645
Assessment$385,400
Home facts updated by county records

Comparable Sales for 25 Skytop Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
38 Skytop Drive, Madison, CT
0.08
Single-Family Home
$878,000
06/27/25
3
2.5
2,204
26 Flintlock Road, Madison, CT
0.23
Single-Family Home
$775,000
02/09/26
5
3
2,904
76 Horse Pond Road, Madison, CT
0.23
Single-Family Home
$680,000
07/18/25
4
3
3,037
29 Flintlock Road, Madison, CT
0.20
Single-Family Home
$711,000
08/21/25
4
1.5
2,458
16 Yankee Peddler Path, Madison, CT
0.29
Single-Family Home
$645,000
05/12/26
4
3.5
3,590
41 Sportsman Hill Road, Madison, CT
0.44
Single-Family Home
$690,000
08/13/25
4
3.5
3,120
118 Flintlock Road, Madison, CT
0.42
Single-Family Home
$705,000
08/07/25
3
2
1,840
94 Sportsman Hill Road, Madison, CT
0.26
Single-Family Home
$739,000
08/22/25
5
3.5
3,892
67 New Road, Madison, CT
0.42
Single-Family Home
$550,000
06/23/25
3
2
1,576
40 Puritan Lane, Madison, CT
0.55
Single-Family Home
$625,000
03/02/26
4
3.5
2,656

Nearby homes

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Assigned Schools

These are the assigned schools for 25 Skytop Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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.
  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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25 Skytop Dr, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,886 sqft single-family home built in 1966. This property is not currently available for sale. 25 Skytop Dr was last sold on Dec 19, 2022 for $540,000. The current Trulia Estimate for 25 Skytop Dr is $858,200.