5 Highview Rd, Madison, CT 06443
Property image
Property image
OFF MARKET

5 Highview Rd
Madison, CT 06443

  • 5 Beds
  • 3.5 Baths
  • 3,936 sqft (on 1.53 acres)

$1,237,800

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $8,596/mo*
Refinance Your Home

$1,237,800

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $8,596/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,936 sqft
(on 1.53 acres)

Home Value

Trulia Estimate
$1.24M
Since last month
Decreased$2K (-0.2%)
Since last year
Increased$72K (+6.2%)
Since last sale
Increased$313K (+33.8%)
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 +81% in the last 10 years
MonthEstimated value
2026
August 2026$1.24M
July 2026$1.24M
June 2026$1.26M
May 2026$1.22M
April 2026$1.21M
March 2026$1.19M
February 2026$1.16M
January 2026$1.15M
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
31 Meadowbrook Road, Madison, CT
0.20
Single-Family Home
$1,005,000
08/28/25
4
2.5
3,360
123 Five Fields Road, Madison, CT
0.40
Single-Family Home
$860,000
08/29/25
5
2.5
3,664
318 Horsepond Road, Madison, CT
0.30
Single-Family Home
$725,000
12/22/25
4
2.5
2,622
56 Buttonball Ln, Madison, CT
0.58
Single-Family Home
$735,000
10/30/25
5
2.5
3,230
8 Highview Rd, Madison, CT
0.07
Single-Family Home
$1,050,000
03/03/26
5
3
2,781
125 Wildcat Road, Madison, CT
0.73
Single-Family Home
$1,000,000
07/07/26
4
2.5
3,909
97 Kelsey Springs Drive, Madison, CT
0.54
Single-Family Home
$1,022,500
01/12/26
4
2.5
2,632
72 Kelsey Springs Drive, Madison, CT
0.59
Single-Family Home
$815,000
10/23/25
4
2.5
3,039
9 Randi Drive, Madison, CT
0.64
Single-Family Home
$967,500
08/20/26
4
2.5
2,807
190 Wildcat Road, Madison, CT
0.55
Single-Family Home
$1,260,444
08/07/26
3
2.5
2,451

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
18 Richborough Road, Madison, CT 06443
0.09
$1,213,600
4
3
3,048
Off Market
15 Richborough Road, Madison, CT 06443
0.11
$1,113,700
4
3
3,262
Off Market
31 Highview Road, Madison, CT 06443
0.16
$1,107,000
4
4.5
4,401
Off Market
57 River Road, Clinton, CT 06413
0.19
$345,600
1
1.5
590
Off Market
31 Meadowbrook Road, Madison, CT 06443
0.20
$1,039,900
4
2.5
3,360
Off Market
69 River Road, Clinton, CT 06413
0.26
$299,000
1
1.5
452
For Sale
96 River Road, Clinton, CT 06413
0.27
$249,700
3
1.5
1,600
Off Market
49 River Road, Clinton, CT 06413
0.29
$450,000
2
1.5
1,179
Recently Sold
4 Oscela Trail, Clinton, CT 06413
0.30
$353,700
4
1
1,962
Off Market
318 Horsepond Road, Madison, CT 06443
0.30
$725,000
4
2.5
2,622
Recently Sold
7 Old Duck Hole Road, Madison, CT 06443
0.37
$596,200
4
2.5
3,680
Off Market
7 Ridgeway Road, Clinton, CT 06413
0.36
$582,900
3
2
2,401
Off Market

Local Information

  • Map ViewExplore the area around 5 Highview Rd.
  • Schools2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1986
Lot Size
1.53 acres
Living Area
3,936 sqft
Price/Sqft
$314
Parking
Garage

About this House

A Showstopper! This Stunning Colonial is located on a quiet corner cul-de-sac in a much sought after Richborough Subdivision was renovated in 2014 with a fresh, modern interior. A masterfully designed kitchen with stainless steel appliances, granite counters, 6 burner gas oven range, ice maker and wine fridge opens to the formal dining room and a leisurely family room. The living room is spectacular with floor to ceiling windows, open beamed ceiling, custom mill work and a striking gas fireplace . The dining room area offers a custom built bar area large enough for entertaining on a grand scale or intimately. On the 2nd floor, the master bedroom en suite has a beautifully tiled steam shower and jetted tub. The 3rd floor offers a private bedroom suite perfect for guests or just about anyone. A wrap around deck looks out over the tiered backyard, which is adjacent to the tennis courts and pond for easy kayaking access. According to the zoning department, a built in swimming pool is possible with some reconstruction of the backyard. Superb location in a desirable neighborhood and just minutes from Madison Town Center and beaches.
5 Highview Rd, Madison, CT 06443 is a 5 bedroom, 4 bathroom, 3,936 sqft single-family home built in 1986. It last sold for $928,000 on Sep 11, 2021. It is currently off market. The Trulia Estimate is $1,237,800, with a rent estimate of $6,376/month.

Home Details for 5 Highview Rd

Interior Features

Interior Details
BasementNumber of Rooms: 11Types of Rooms: Walk In Closet, Dining Room, Family Room, Master Bath, Recreation RoomWet Bar
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceJetted Bath Tub

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: Other, WoodLawnSprinkler System
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1986Year Updated: 2014
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Lot Information

Lot Area: 1.53 acres

Price and Tax history

DateEventPrice
Sep 11, 2021
Source: Smart MLS #170424417
Sold
$928,000
Feb 23, 2020
Source: Agent Provided
ListingRemoved
$749,000
Dec 30, 2019
Source: Agent Provided
PriceChange
$749,000
Price decreased by 2%
Sep 27, 2019
Source: Agent Provided
PriceChange
$765,000
Price decreased by 4%
Jun 24, 2019
Source: Agent Provided
Listed For Sale
$795,000

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

LGBTQ Local Legal Protections

Frequently asked questions about 5 Highview Rd

  • What is 5 Highview Rd estimated to be worth?
    Trulia's estimated value for 5 Highview Rd in Madison, CT is $1,237,800.
  • What is the price history for 5 Highview Rd?
    5 Highview Rd in Madison, CT last sold for $928,000 in September 2021.
  • 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.
  • Does 5 Highview Rd have air conditioning?
    Yes, 5 Highview Rd in Madison, CT has air conditioning.
  • Does 5 Highview Rd have laundry facilities?
    Yes, 5 Highview Rd in Madison, CT has in-unit laundry.

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