5 Highview Rd, Madison, CT 06443
OFF MARKET

5 Highview Rd
Madison, CT 06443

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

$1,218,700

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $8,381/mo*
Refinance Your Home

$1,218,700

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $8,381/mo*
Refinance Your Home
5 Beds
3.5 Baths
3,936 sqft
(on 1.53 acres)

Local Information

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

Description

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.
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
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

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, Oil, OtherAir 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 History for 5 Highview Rd

DatePriceEventSource
09/11/2021$928,000Sold
Smart MLS #170424417
02/23/2020$749,000ListingRemovedAgent Provided
12/30/2019$749,000PriceChange
Agent Provided
09/27/2019$765,000PriceChange
Agent Provided
06/24/2019$795,000Listed For SaleAgent Provided
01/16/2014$525,000Sold
Smart MLS #M9144163
11/05/2013$499,900Listed For SaleAgent Provided
05/29/2007$762,000Sold
Smart MLS #M9102580
06/17/1988$525,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$14,994
Assessment$668,500
Home facts updated by county records

Comparable Sales for 5 Highview Rd

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
78 Wildcat Springs Drive, Madison, CT
0.49
Single-Family Home
$1,350,000
08/12/25
4
3.5
3,569
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
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
94 Sportsman Hill Road, Madison, CT
0.91
Single-Family Home
$739,000
08/22/25
5
3.5
3,892
139 Five Fields Road, Madison, CT
0.50
Single-Family Home
$749,000
06/27/25
3
3
2,352

Nearby homes

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Assigned Schools

These are the assigned schools for 5 Highview Rd.
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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 56 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

  • 13 % 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
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  • 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
    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
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5 Highview Rd, Madison, CT 06443 is a 5 bedroom, 4 bathroom, 3,936 sqft single-family home built in 1986. This property is not currently available for sale. 5 Highview Rd was last sold on Sep 11, 2021 for $928,000. The current Trulia Estimate for 5 Highview Rd is $1,218,700.