18 Highview Dr, Wilton, CT 06897
OFF MARKET

18 Highview Dr
Wilton, CT 06897

  • 5 Beds
  • 6.5 Baths
  • 7,618 sqft (on 3.70 acres)

$3,325,100

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $21,642/mo*
Refinance Your Home

$3,325,100

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $21,642/mo*
Refinance Your Home
5 Beds
6.5 Baths
7,618 sqft
(on 3.70 acres)

Local Information

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

Description

Welcome to High View, a distinctive custom country estate on 3.7 beautiful acres in the heart of Wilton. Surrounded with landscaped lawn and magnificent meadow, the home's outstanding architecture features mahogany wrap-around porches, three-story curved staircase tower, handsome millwork and a stunning 40'x 20' pool with limestone decking. Vibrant vistas of the expansive property bordered by a 14 acre preserve bring a sense of serenity and total privacy. Upon entering, one feels the warm, relaxed living with the open flow and Craftsman-style sensibility. Chef's dream Kitchen boasts Wolf, Miele & Subzero appliances & central island w/ refrigerator & freezer drawers, prep sink & cherry countertop. Gather by a warm fire in the sunlit Family Room or curl-up with a great book in the cozy Den. Entertaining is easy with doors to the deck, terraces and steppingstones to the lower yard & meadow. After a long day, retire to the Master Suite with fireplace & spa-like bath w/ heated floor, soaking tub & steam shower. Additional bedrooms are close by and a special suite down the hall with bright common area is ideal for visiting family & guests. Ready for a workout? Head to the LL with gym, full bath, kitchenette & 2nd laundry. Stream your favorite shows in the recreation area and come summer, a refreshing swim in the pool is just steps away Close to Wilton's top-rated schools, great restaurants & convenient commute to the City, 18 Highview is the perfect home for the discerning buyer.
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
Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 18 Highview Dr

Interior Features

Interior Details
BasementAtticNumber of Rooms: 13
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 3
Appliances & Utilities
DishwasherDryerMicrowaveWasher
Fireplace & Spa
Fireplace
Security
Security System

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: WoodPatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2005Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 3.70 acres

Price History for 18 Highview Dr

DatePriceEventSource
06/11/2021$2,720,000Sold
Smart MLS #170379947
04/03/2021$2,799,000PendingBerkshire Hathaway HomeServices New England Properties #170379947
04/03/2021$2,799,000ContingentSmart MLS #170379947
03/19/2021$2,799,000Listed For SaleSmart MLS #170379947
04/23/2003$900,000Sold
N/A
01/25/2001$595,000Sold
N/A
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$39,741
Assessment$1,628,060
Home facts updated by county records

Comparable Sales for 18 Highview Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
148 Drum Hill Road, Wilton, CT
0.22
Single-Family Home
$2,800,000
08/13/25
5
5.5
6,798
33 Middlebrook Farm Road, Wilton, CT
0.38
Single-Family Home
$2,335,000
03/31/26
5
6
5,860
88 Drum Hill Road, Wilton, CT
0.16
Single-Family Home
$2,250,000
03/23/26
6
4.5
4,009
46 Glen Hill Road, Wilton, CT
0.35
Single-Family Home
$1,400,000
08/28/25
5
3.5
4,336
132 Belden Hill Road, Wilton, CT
0.86
Single-Family Home
$2,500,000
09/05/25
6
7
8,636
12 Comstock Ln, Wilton, CT
0.84
Single-Family Home
$2,120,000
06/02/25
5
5
8,281
93 Graenest Ridge Road, Wilton, CT
0.98
Single-Family Home
$2,600,000
09/04/25
5
6
6,447
175 Middlebrook Farm Road, Wilton, CT
1.00
Single-Family Home
$2,475,000
05/30/25
5
6
6,560
125 Middlebrook Farm Rd, Wilton, CT
0.96
Single-Family Home
$2,875,000
09/19/25
5
7
6,426
87 Catalpa Road, Wilton, CT
0.82
Single-Family Home
$2,220,000
10/30/25
5
3.5
5,153

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 18 Highview 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 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

  • 18 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • 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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature

Homes for sale near 18 Highview Dr

Skip to last item
Skip to first item

Off Market Homes Near 18 Highview Dr

Skip to last item
Skip to first item

Homes for rent near 18 Highview Dr

Skip to last item
Skip to first item
18 Highview Dr, Wilton, CT 06897 is a 5 bedroom, 7 bathroom, 7,618 sqft single-family home built in 2005. This property is not currently available for sale. 18 Highview Dr was last sold on Jun 11, 2021 for $2,720,000. The current Trulia Estimate for 18 Highview Dr is $3,325,100.