398 Olmstead Hill Rd, Wilton, CT 06897
Property image
Property image
OFF MARKET

398 Olmstead Hill Rd
Wilton, CT 06897

  • 3 Beds
  • 2 Baths
  • 2,373 sqft (on 2 acres)

$1,146,800

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $7,549/mo*
Refinance Your Home

$1,146,800

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $7,549/mo*
Refinance Your Home
3 Beds
2 Baths
2,373 sqft
(on 2 acres)

Home Value

Trulia Estimate
$1.15M
Since last month
Increased$7K (+0.6%)
Since last year
Increased$69K (+6.4%)
Since last sale
Increased$534K (+86.8%)
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 +89% in the last 10 years
MonthEstimated value
2026
August 2026$1.15M
July 2026$1.14M
June 2026$1.17M
May 2026$1.16M
April 2026$1.13M
March 2026$1.11M
February 2026$1.07M
January 2026$1.05M
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
22 Cobblestone Place, Wilton, CT
0.42
Single-Family Home
$1,030,000
07/24/26
4
3
2,872
63 Cannon Road, Wilton, CT
0.32
Single-Family Home
$875,000
08/14/26
4
3
1,864
32 Cobblestone Place, Wilton, CT
0.48
Single-Family Home
$1,125,000
11/12/25
4
2.5
2,000
146 Scribner Hill Road, Wilton, CT
1.05
Single-Family Home
$650,000
02/27/26
3
1.5
1,368
43 Blue Ridge Road, Wilton, CT
0.60
Single-Family Home
$839,000
11/10/25
4
3.5
1,484
221 Catalpa Road, Wilton, CT
0.81
Single-Family Home
$1,310,000
06/30/26
4
2.5
2,520
32 Catalpa Road, Wilton, CT
0.70
Single-Family Home
$983,000
05/29/26
4
3.5
2,964
20 Warncke Rd, Wilton, CT
0.58
Single-Family Home
$1,445,000
06/03/26
5
4
4,258
79 Warncke Road, Wilton, CT
0.59
Single-Family Home
$1,600,000
06/04/26
4
4.5
4,386
36 Scribner Hill Road, Wilton, CT
0.79
Single-Family Home
$345,000
06/01/26
1
2
1,288

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 Sugarloaf Drive, Wilton, CT 06897
0.06
$1,373,200
3
3
3,284
Off Market
20 Saunders Drive, Wilton, CT 06897
0.13
$1,956,400
4
4.5
4,460
Off Market
8 Fairview Lane, Wilton, CT 06897
0.12
$1,023,900
4
2
2,102
Off Market
64 Sugarloaf Drive, Wilton, CT 06897
0.26
$888,600
3
2
1,740
Off Market
63 Cannon Road, Wilton, CT 06897
0.32
$875,000
4
3
1,864
Recently Sold
33 Cannon Road, Wilton, CT 06897
0.34
$1,850,000
6
6
7,068
Recently Sold
66 Saunders Drive, Wilton, CT 06897
0.33
$1,410,500
4
4
3,782
Off Market
72 Cannon Road, Wilton, CT 06897
0.36
$2,346,900
5
6
7,523
Off Market
323 Olmstead Hill Road, Wilton, CT 06897
0.39
$1,106,900
5
3.5
2,434
Off Market
105 Seeley Road, Wilton, CT 06897
0.38
$5,819,800
5
6
6,843
Off Market
22 Cobblestone Place, Wilton, CT 06897
0.42
$1,030,000
4
3
2,872
Recently Sold
32 Cobblestone Place, Wilton, CT 06897
0.47
$1,125,000
4
2.5
2,000
Recently Sold

Local Information

  • Map ViewExplore the area around 398 Olmstead Hill Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1949
Lot Size
2 acres
Living Area
2,373 sqft
Price/Sqft
$483
Parking
Garage

About this House

Storybook cottage with off the charts charm, appeal, and updates, this impressive 2,373 sqft Cape measures up to much more expensive homes. Special MAIN-FLOOR features include stylish new kitchen open to vaulted FR; Front-to-Back LR; 2 FPLs; Expanded DR to comfortably seat 16; and gracious MBR with sitting area; UPPER-FLOOR bedrooms are spacious enough to share or divide as desired. Sited beautifully on 2 level acres of corner property, the open backyard, lush landscape, perennial gardens, and huge deck maximize outdoor fun. With so much to enjoy, this house will suit as charming down-sizer or warm family-sized home, perfectly located close to all amenities, schools, shopping, dining, and commutes. Make this special house your special home!
398 Olmstead Hill Rd, Wilton, CT 06897 is a 3 bedroom, 2 bathroom, 2,373 sqft single-family home built in 1949. It last sold for $615,000 on Jul 18, 2014. It is currently off market. The Trulia Estimate is $1,146,800, with a rent estimate of $5,313/month.

Home Details for 398 Olmstead Hill Rd

Interior Features

Interior Details
BasementNumber of Rooms: 7
Heating & Cooling
Heating: Forced Air, OilAir ConditioningHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: Other
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1949
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 2.00 acres

Price and Tax history

DateEventPrice
Jul 18, 2014
Source: Smart MLS #99062602
Sold
$615,000
May 2, 2014
Source: Agent Provided
Listed For Sale
$619,000
Jun 12, 1998
Source: Smart MLS #98005901
Sold
$357,500

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 398 Olmstead Hill Rd

  • What is 398 Olmstead Hill Rd estimated to be worth?
    Trulia's estimated value for 398 Olmstead Hill Rd in Wilton, CT is $1,146,800.
  • What is the price history for 398 Olmstead Hill Rd?
    398 Olmstead Hill Rd in Wilton, CT last sold for $615,000 in July 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.
  • How big is the lot at 398 Olmstead Hill Rd?
    The lot at 398 Olmstead Hill Rd in Wilton, CT is about 2 acres.
  • Does 398 Olmstead Hill Rd have a garage?
    Yes, 398 Olmstead Hill Rd in Wilton, CT has a garage.

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Off Market Homes Near 398 Olmstead Hill Rd

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