21 Highview Dr, Wilton, CT 06897
Property image
Property image
OFF MARKET

21 Highview Dr
Wilton, CT 06897

  • 3 Beds
  • 3 Baths
  • 2,964 sqft (on 2.73 acres)

$1,361,900

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $8,959/mo*
Refinance Your Home

$1,361,900

Trulia Estimate
as of Aug 21, 2026
Est. Refi. Payment $8,959/mo*
Refinance Your Home
3 Beds
3 Baths
2,964 sqft
(on 2.73 acres)

Home Value

Trulia Estimate
$1.36M
Since last month
Decreased$1K (-0.1%)
Since last year
Increased$48K (+3.6%)
Since last sale
Increased$636K (+87.7%)
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 +90% in the last 10 years
MonthEstimated value
2026
August 2026$1.36M
July 2026$1.36M
June 2026$1.4M
May 2026$1.38M
April 2026$1.33M
March 2026$1.35M
February 2026$1.27M
January 2026$1.27M
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
46 Glen Hill Road, Wilton, CT
0.33
Single-Family Home
$1,400,000
08/28/25
5
3.5
4,336
20 Pheasant Run Road, Wilton, CT
0.61
Single-Family Home
$1,505,000
03/06/26
4
2.5
3,290
88 Drum Hill Road, Wilton, CT
0.20
Single-Family Home
$2,250,000
03/23/26
6
4.5
4,009
2 Pheasant Run Road, Wilton, CT
0.63
Single-Family Home
$1,350,000
07/31/26
4
2.5
3,817
65 Ridgefield Road, Wilton, CT
0.53
Single-Family Home
$2,600,000
07/13/26
4
2.5
3,324
300 Ridgefield Road, Wilton, CT
0.59
Single-Family Home
$1,370,000
10/15/25
5
2.5
4,303
352 Ridgefield Road, Wilton, CT
0.80
Single-Family Home
$1,600,000
10/15/25
4
3.5
4,152
112 Middlebrook Farm Road, Wilton, CT
0.94
Single-Family Home
$1,350,000
12/30/25
4
2.5
3,880
12 Walnut Place, Wilton, CT
0.69
Single-Family Home
$1,615,000
09/24/25
4
4
4,780
33 Middlebrook Farm Road, Wilton, CT
0.44
Single-Family Home
$2,335,000
03/31/26
5
6
5,860

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
148 Drum Hill Road, Wilton, CT 06897
0.17
$2,978,900
5
5.5
6,798
Off Market
127 Drum Hill Road, Wilton, CT 06897
0.14
$1,663,400
4
3.5
3,057
Off Market
90 Drum Hill Road, Wilton, CT 06897
0.16
$905,000
-
-
-
Recently Sold
88 Drum Hill Road, Wilton, CT 06897
0.20
$2,250,000
6
4.5
4,009
Recently Sold
24 Glen Hill Road, Wilton, CT 06897
0.25
$1,494,500
5
2.5
3,026
Off Market
105 Drum Hill Road, Wilton, CT 06897
0.23
$2,929,200
7
6
6,259
Off Market
174 Ridgefield Road, Wilton, CT 06897
0.25
$2,297,000
5
4.5
5,070
Off Market
188 Drum Hill Road, Wilton, CT 06897
0.31
$934,800
2
2
1,792
Off Market
74 Drum Hill, Wilton, CT 06897
0.24
$2,451,400
4
6
5,400
Off Market
122 Ridgefield Road, Wilton, CT 06897
0.32
$2,194,600
5
5.5
5,591
Off Market
208 Ridgefield Road, Wilton, CT 06897
0.30
$1,404,300
4
3
4,674
Off Market
46 Glen Hill Road, Wilton, CT 06897
0.33
$1,488,700
5
3.5
4,336
Off Market

Local Information

  • Map ViewExplore the area around 21 Highview Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1952
Lot Size
2.73 acres
Living Area
2,964 sqft
Price/Sqft
$459
Parking
Garage

About this House

This single-family home is located at 21 Highview Dr, Wilton, CT. 21 Highview Dr is in Wilton, CT and in ZIP code 06897. This property has 3 bedrooms, 3 bathrooms and approximately 2,964 sqft of floor space. This property has a lot size of 2.73 acres and was built in 1952.
21 Highview Dr, Wilton, CT 06897 is a 3 bedroom, 3 bathroom, 2,964 sqft single-family home built in 1952. It last sold for $725,000 on Jun 19, 2014. It is currently off market. The Trulia Estimate is $1,361,900, with a rent estimate of $7,218/month.

Home Details for 21 Highview Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 6
Heating & Cooling
Heating: Radiant, OilAir ConditioningHeating Fuel: Radiant
Levels, Entrance, & Accessibility
Stories: 1
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltExterior: WoodPatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1952
Property Type / Style
Property Type: Single Family HomeArchitecture: Ranch / Rambler

Community

Units in Building: 1

Lot Information

Lot Area: 2.73 acres

Price and Tax history

DateEventPrice
Jun 19, 2014
Source: Smart MLS #99054623
Sold
$725,000
Apr 8, 2014
Source: Agent Provided
Listed For Sale
$749,000
Oct 27, 1991
Source: N/A
Sold
$415,000
Aug 3, 1988
Source: N/A
Sold
$379,000

Market trends in Wilton

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.42M
Sale-to-List Price
105.8%
Price per sq ft
$424
Available listings
64
2MoM

Around this home

What Locals Say about Wilton

At least 67 Trulia users voted on each feature.

  • 94 % Say car is needed

  • 88 % Say parking is easy

  • 86 % Say there's holiday spirit

  • 84 % Say it's quiet

  • 81 % Say yards are well-kept

  • 81 % Say it's dog friendly

  • 80 % Say there's wildlife

  • 68 % Say people would walk alone at night

  • 66 % Say neighbors are friendly

  • 57 % Say they plan to stay for at least 5 years

  • 56 % Say kids play outside

  • 43 % Say there are community events

  • 24 % Say it's walkable to restaurants

  • 21 % Say streets are well-lit

  • 19 % Say it's walkable to grocery stores

  • 17 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Jelani37
    "It’s a small town, and traffic can be bad during rush hours on the Merritt "
    0
    Flag
  • Aimee Calandria
    "Christmas caroling, Memorial parade, farmers market, garden sale, Halloween parade, summer outside sale"
    0
    Flag
  • Kim Biltoft
    "Family oriented, very neighborly, help is there when you ask for it. Lots of ways to get involved in the community. "
    0
    Flag
  • Avdi R.
    "Very nice and friendly town! Very quiet and peaceful. Well kept neighborhoods and town. I spend a lot of time walking trails and enjoying the local town plazas"
    2
    Flag
  • Geneveaninevanstaden
    "Wilton is a lovely town to live in and the community is kind, friendly & welcoming. The public & communal areas are well kept and the parks & recreation facilities are well maintained. Wilton has great schools & is a great town for families."
    2
    Flag
  • Kelly H.
    "Best area to raise a family! The people are great! The schools are great! The public areas are great!"
    0
    Flag
  • Geneveaninevanstaden
    "Recently moved to Wilton and absolutely love it. We love going for family walks in the nature trails, or just taking a walk to the local restaurants or cafes. The parks are clean and well maintained, the rivers and lakes are clear and looked after. The Wilton community is friendly and welcoming, it’s a great place to call home."
    3
    Flag
  • Annie O.
    "This is a small city located in Fairfield Co Connecticut, known locally as “the country” and for being a little over an hour commute outside of NYC. Getting to a major highway requires driving through neighborhoods. "
    1
    Flag
  • Ygibney
    "Great schools close to ymca close to supermarket and close to train. Convenient location to neighboring towns ."
    0
    Flag
  • Barbara S.
    "Wilton is a caring, active, and beautiful community. A terrific library and many interest groups expand the reach of the educational resources. "
    0
    Flag
  • Azlouko
    "Fun family events in town Friendly neighbors Good school system Halloween parade Memorial Day parade"
    1
    Flag
  • Nya
    "Great schools, safe to live. We don’t have a great downtown but near by towns have. We have few good restaurants, great library and a farmers market. "
    0
    Flag
  • Samwals
    "No , there is no public transportation here. Everything is done by car. The city is spread out and there is no way they could supply public transportation except for the elderly "
    1
    Flag
  • BlessedOne
    "Lived in Wilton for 11 years. Plus is Low crime rate. Negative is expensive rent for old houses that are not update and built in 1900’s."
    1
    Flag
  • Trulia User
    "Great fairs, library events, parades! Super fun place to live. Outdoor activities too including hiking and biking. "
    0
    Flag
  • Pookie368
    "Most parts near me are not good to walk a dog. Not a lot of sidewalks and a lot of traffic. There are however a few parks to walk with your dog scattered around town."
    0
    Flag
  • Samwals
    "It doesn’t feel unique . There is nothing special about the town nor the neighborhood. The people are hoodwinked by the propaganda about how great the schools are. Scores have declined each year. "
    2
    Flag
  • Elizabethalleva
    "Wilton is amazing! Great schools. Great people. Beautiful homes!! This is a wonderful place to raise a family"
    4
    Flag
  • Samwals
    "Beautiful neighborhood, over rated schools. High taxes, high debt, Low turnout on budget issues. Poor road maintenance, wasted money on new school, with declining school age population. Retail outlets closing, with no incentives to stay. No plan to attract new businesses. A pompous attitude prevails by a community who time past by"
    0
    Flag
  • nrbattista
    "Outstanding area for raising children and commuting to NYC."
    0
    Flag
  • Liz C.
    "We live here and it is the best place we have ever lived! We thought when we bought it that we would move in a couple of years, but now we know this has everything we need and is safe, walkable, pet friendly, conveniently located and the neighborhood community is awesome. Having 4 bedrooms and a detached house with plenty of parking for our family and guests makes living easy. Our resident board and the management company are proactive and approachable. The grounds and upkeep through every season have been outstanding, nothing to complain about! These houses rarely come on the market and when they do there are always multiple bids. This has proven to be an amazing investment. Grumman Village possesses a desirable and stable mixed neighborhood of families, singles, couples and retirees."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 21 Highview Dr

  • What is 21 Highview Dr estimated to be worth?
    Trulia's estimated value for 21 Highview Dr in Wilton, CT is $1,361,900.
  • What is the price history for 21 Highview Dr?
    21 Highview Dr in Wilton, CT last sold for $725,000 in June 2014.
  • Is Wilton a buyer's or seller's market?
    Wilton is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Wilton?
    The median sale price in Wilton is $1.42M.
  • Does 21 Highview Dr have a pool?
    Yes, 21 Highview Dr in Wilton, CT has a pool.
  • Does 21 Highview Dr have laundry facilities?
    Yes, 21 Highview Dr in Wilton, CT has in-unit laundry.

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Off Market Homes Near 21 Highview Dr

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