25 Skytop Dr, Madison, CT 06443
Property image
Property image
OFF MARKET

$835,600

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

25 Skytop Dr, Madison, CT 06443

Est. Refi. Payment $5,863/mo*
Refinance Your Home
Currently Off Market - Sold Dec 19, 2022 for $540,000

Home Value

Trulia Estimate
$836K
Since last month
Decreased$14K (-1.7%)
Since last year
Increased$27K (+3.3%)
Since last sale
Increased$292K (+54%)
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 +119% in the last 10 years
MonthEstimated value
2026
August 2026$832K
July 2026$846K
June 2026$884K
May 2026$858K
April 2026$849K
March 2026$824K
February 2026$813K
January 2026$813K
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
26 Flintlock Road, Madison, CT
0.23
Single-Family Home
$775,000
02/09/26
5
3
2,904
221 Duck Hole Road, Madison, CT
0.41
Single-Family Home
$600,000
07/17/26
3
3
2,068
190 Wildcat Road, Madison, CT
0.18
Single-Family Home
$1,260,444
08/07/26
3
2.5
2,451
6 Yankee Peddler Path, Madison, CT
0.33
Single-Family Home
$660,000
06/12/26
4
2
2,642
16 Yankee Peddler Path, Madison, CT
0.29
Single-Family Home
$645,000
05/12/26
4
3.5
3,590
107 Horse Pond Road, Madison, CT
0.05
Single-Family Home
$430,000
06/12/26
3
2
864
12 Sportsman's Hill Road, Madison, CT
0.56
Single-Family Home
$515,000
06/24/26
4
2
2,746
125 Wildcat Road, Madison, CT
0.39
Single-Family Home
$1,000,000
07/07/26
4
2.5
3,909
40 Puritan Lane, Madison, CT
0.55
Single-Family Home
$625,000
03/02/26
4
3.5
2,656
71 Madison Springs Drive, Madison, CT
0.65
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
38 Skytop Drive, Madison, CT 06443
0.08
$917,700
3
2.5
2,204
Off Market
107 Horse Pond Road, Madison, CT 06443
0.05
$430,000
3
2
864
Recently Sold
137 Horse Pond Road, Madison, CT 06443
0.04
$893,800
4
3
3,509
Off Market
99 Horse Pond Road, Madison, CT 06443
0.11
$583,100
3
2
1,956
Off Market
142 Horse Pond Road, Madison, CT 06443
0.11
$876,400
4
2.5
3,420
Off Market
29 Flintlock Road, Madison, CT 06443
0.20
$740,900
4
1.5
2,458
Off Market
128 Horse Pond Road, Madison, CT 06443
0.16
$891,100
3
2.5
2,578
Off Market
190 Wildcat Road, Madison, CT 06443
0.18
$1,260,444
3
2.5
2,451
Recently Sold
26 Flintlock Road, Madison, CT 06443
0.23
$775,000
5
3
2,904
Recently Sold
76 Horse Pond Road, Madison, CT 06443
0.23
$709,900
4
3
3,037
Off Market
94 Sportsman Hill Road, Madison, CT 06443
0.26
$770,000
5
3.5
3,892
Off Market
92 Sportsman Hill Road, Madison, CT 06443
0.28
$629,100
4
2.5
1,902
Off Market

Local Information

  • Map ViewExplore the area around 25 Skytop Dr.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1966
Lot Size
1.07 acres
Living Area
2,886 sqft
Price/Sqft
$290
Parking
Garage

About this House

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.
25 Skytop Dr, Madison, CT 06443 is a 3 bedroom, 3 bathroom, 2,886 sqft single-family home built in 1966. It last sold for $540,000 on Dec 19, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $835,600, with a rent estimate of $4,933/month.

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 and Tax history

DateEventPrice
Dec 19, 2022
Source: Smart MLS #170528429
Sold
$540,000
Dec 9, 2022
Source: William Raveis Real Estate, Mortgage & Insurance #170528429
PendingToActive
$549,900
Dec 9, 2022
Source: Smart MLS #170528429
Contingent
$549,900
Nov 14, 2022
Source: William Raveis Real Estate, Mortgage & Insurance #170528429
Pending
$549,900
Oct 20, 2022
Source: Smart MLS #170528429
Listed For Sale
$549,900

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

LGBTQ Local Legal Protections

Frequently asked questions about 25 Skytop Dr

  • What is 25 Skytop Dr estimated to be worth?
    Trulia's estimated value for 25 Skytop Dr in Madison, CT is $835,600.
  • What is the price history for 25 Skytop Dr?
    25 Skytop Dr in Madison, CT last sold for $540,000 in December 2022.
  • 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 25 Skytop Dr?
    The lot at 25 Skytop Dr in Madison, CT is about 1.1 acres.
  • Does 25 Skytop Dr have a garage?
    Yes, 25 Skytop Dr in Madison, CT has a garage.

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