398 Olmstead Hill Rd, Wilton, CT 06897
OFF MARKET

398 Olmstead Hill Rd
Wilton, CT 06897

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

$1,146,100

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $7,460/mo*
Refinance Your Home

$1,146,100

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $7,460/mo*
Refinance Your Home
3 Beds
2 Baths
2,373 sqft
(on 2 acres)

Local Information

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

Description

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!
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 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 History for 398 Olmstead Hill Rd

DatePriceEventSource
07/18/2014$615,000Sold
Smart MLS #99062602
05/02/2014$619,000Listed For SaleAgent Provided
06/12/1998$357,500Sold
Smart MLS #98005901
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Property Tax and Assessment

Year2025
Tax$13,063
Assessment$535,150
Home facts updated by county records

Comparable Sales for 398 Olmstead Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
32 Cobblestone Place, Wilton, CT
0.48
Single-Family Home
$1,125,000
11/12/25
4
2.5
2,000
66 Saunders Drive, Wilton, CT
0.33
Single-Family Home
$1,325,000
07/28/25
4
4
3,782
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
160 Olmstead Hill Road, Wilton, CT
0.89
Single-Family Home
$1,885,000
10/24/25
4
3
3,282
322 Mountain Road, Wilton, CT
1.33
Single-Family Home
$950,000
10/01/25
3
2
2,153
33 Cannon Road, Wilton, CT
0.34
Single-Family Home
$1,850,000
12/01/25
6
6
7,068
37 Saint Johns Road, Wilton, CT
0.88
Single-Family Home
$1,435,000
07/15/25
5
3.5
4,062
72 Cannon Road, Wilton, CT
0.36
Single-Family Home
$2,202,805
07/22/25
5
6
7,523
11 Ambler Lane, Wilton, CT
1.09
Single-Family Home
$1,305,000
06/30/25
5
2.5
3,034

Nearby homes

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Assigned Schools

These are the assigned schools for 398 Olmstead Hill Rd.
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
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398 Olmstead Hill Rd, Wilton, CT 06897 is a 3 bedroom, 2 bathroom, 2,373 sqft single-family home built in 1949. This property is not currently available for sale. 398 Olmstead Hill Rd was last sold on Jul 18, 2014 for $615,000. The current Trulia Estimate for 398 Olmstead Hill Rd is $1,146,100.