23 Highland Road, Springfield, VT 05156
OFF MARKET
Listed by Laird Bradley, Williamson Group Sothebys Intl. Realty, (802) 457-2000 . Bought with Williamson Group Sothebys Intl. Realty

23 Highland Road
Springfield, VT 05156

  • 6 Beds
  • 7 Baths
  • 6,506 sqft (on 4.38 acres)

$842,400

Trulia Estimate
as of Jun 3, 2026

$842,400

Trulia Estimate
as of Jun 3, 2026
6 Beds
7 Baths
6,506 sqft
(on 4.38 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination
Last check for updates: about 19 hours ago
Listed by Laird Bradley
Williamson Group Sothebys Intl. Realty, (802) 457-2000
Bought with: Terry Davis, Williamson Group Sothebys Intl. Realty, (802) 457-2000
Source: PrimeMLS, MLS#4811649

Description

The 'Smiley Manse',is named after a Scottish Presbyterian minister and original owner-builder in 1811 of this extraordinary historic home. A later occupant, Senator Ralph Flanders, commissioned the 1929 addition and a comprehensive renovation, which has been refined and maintained to a high standard under the stewardship of successive owners. The gracious historic floor plan remains relevant for modern living styles with the spacious gathering rooms, bespoke Smallbone kitchen imported from England with its AGA stove and a variety of special purpose rooms. The home offers 10 working wood burning fireplaces and all 6 bedrooms are appointed for comfort and privacy with bath en suite. A remarkable feature of the home is the former Flanders Library, which was originally conceived as a music room with a parabolic shaped ceiling possessing superb acoustics. Currently this great room is used for recreation and display of historic reference books and collections of sporting equipment. The grounds are superbly landscaped and feature an in-ground spa, Har-tru tennis court wide covered patio, grape arbor and one of the regions' finest carriage barns. All of the structures are clad with Vermont slate roofs and old-growth clapboards. Oriented to southerly views, the Manse is discretely located in a neighborhood populated by dozens of Vermont's finest residences representing architectural styles and sizes afforded by wealth produced at the zenith of the Machine Tool Industry.
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. This description is from June 02, 2022

Home Highlights

Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 23 Highland Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Basement: Bulkhead,Concrete,Concrete Floor,Unfinished,Basement Stairs,Interior EntryNumber of Rooms: 18
Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 8Number of Bathrooms (full): 6Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 6506 Square Feet
Appliances & Utilities
Utilities: CableAppliances: Dishwasher, Disposal, Dryer, Microwave, Gas Range, Washer, Oil Water Heater, Wine CoolerDishwasherDisposalDryerLaundry: 1st Floor LaundryMicrowaveWasher
Heating & Cooling
Heating: Oil,Hot Water,Zoned,SteamHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Oil
Fireplace & Spa
Fireplace: Wood Burning, 3+ FireplacesHas a Fireplace
Gas & Electric
Electric: 200+ Amp Service
Windows, Doors, Floors & Walls
Flooring: Hardwood, Softwood, Tile
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Hardwood, Softwood, Tile
View
Has a ViewView: Mountain(s)

Exterior Features

Exterior Home Features
Roof: SlateFoundation: Concrete, Stone
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageParking Spaces: 3Parking: Paved,Attached
Frontage
Road Frontage: PublicRoad Surface Type: Paved
Water & Sewer
Sewer: Public Sewer
Farm & Range
Frontage Length: Road frontage: 480
Finished Area
Finished Area (above surface): 6506 Square Feet

Property Information

Year Built
Year Built: 1811
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Federal
Building
Construction Materials: Masonry, Timber Frame, Wood Frame, Brick Exterior, Clapboard ExteriorNot a New Construction

Price & Status

Price
List Price: $889,500

Location

Direction & Address
City: Springfield
School Information
Elementary School: Elm Hill SchoolElementary School District: Springfield School DistrictJr High / Middle School: Riverside Middle SchoolJr High / Middle School District: Springfield School DistrictHigh School: Springfield High SchoolHigh School District: Springfield School District

Building

Building Area
Building Area: 10504 Square Feet

Lot Information

Lot Area: 4.38 Acres

Miscellaneous

BasementMls Number: 4811649Attic: Attic with Hatch/SkuttleAttribution Contact: Phone: 802-457-2000Above Grade Unfinished Area: 6506Above Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area: 2654Below Grade Unfinished Area Source: Public RecordsBelow Grade Unfinished Area Units: Square Feet

Price History for 23 Highland Road

DatePriceEventSource
06/01/2022$864,000Sold
PrimeMLS #4811649
12/27/2021$889,500ContingentPrimeMLS #4811649
06/23/2021$889,500PriceChange
PrimeMLS #4811649
05/28/2021$985,000Listed For SalePrimeMLS #4811649
04/29/2021ListingRemovedPrimeMLS #4811649
06/18/2020$985,000Listed For SalePrimeMLS #4811649
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Comparable Sales for 23 Highland Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1016 Cherry Hill, Springfield, VT
0.53
Single-Family Home
$535,000
12/11/25
4
3.5
2,865
47 Dell Road, Springfield, VT
0.29
Single-Family Home
$310,000
08/18/25
4
2
2,484
64 Summer Hill Street, Springfield, VT
0.22
Single-Family Home
$365,000
04/28/26
3
2
2,776
215 Elm Hill Street, Springfield, VT
0.57
Single-Family Home
$340,000
03/31/26
4
2.5
2,240
29 Summer Hill, Springfield, VT
0.23
Single-Family Home
$289,000
05/18/26
3
2
1,451
81 Wall Street, Springfield, VT
0.50
Single-Family Home
$245,000
07/31/25
4
1.5
1,742
10 Derby Court, Springfield, VT
0.44
Single-Family Home
$265,000
09/17/25
4
1.5
1,616
9 Fairview Street, Springfield, VT
0.51
Single-Family Home
$180,000
02/10/26
4
1.5
1,482
62 Mark Street, Springfield, VT
0.37
Single-Family Home
$231,500
03/31/26
3
1.5
1,056

Nearby homes

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Assigned Schools

These are the assigned schools for 23 Highland Road.
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 Springfield

At least 18 Trulia users voted on each feature.

  • 88 % Say parking is easy

  • 79 % Say yards are well-kept

  • 78 % Say there are sidewalks

  • 75 % Say car is needed

  • 71 % Say it's dog friendly

  • 68 % Say kids play outside

  • 67 % Say it's walkable to grocery stores

  • 65 % Say it's walkable to restaurants

  • 64 % Say people would walk alone at night

  • 61 % Say there's wildlife

  • 58 % Say there's holiday spirit

  • 52 % Say they plan to stay for at least 5 years

  • 50 % Say it's quiet

  • 46 % Say neighbors are friendly

  • 41 % Say streets are well-lit

  • 26 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "There are not many other dogs around and it is a very nice loop and easy walk to the reservoir. There are a couple of places for them to get wet in the brook and river nearby also!"
    0
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  • Ray Bent
    "Nice and cozy if you live in the north Springfield area. I personally live off of a private road. Neighbors don’t bug me. People here are friendly . "
    0
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  • Sissy A.
    "I’ve lived here for 8 years. The drug epidemic is bad. Schools are not good at all(have 3 in all grades) . Too expensive and not much for the youth to do. Not many shops or stores "
    1
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Homes for sale near 23 Highland Road

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Off Market Homes Near 23 Highland Road

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Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated 2026-06-02 14:59:41 PDT.
This display of listings may or may not be the entire Compilation from the PrimeMLS database, and PrimeMLS does not guarantee the accuracy of such information.

Homes for rent near 23 Highland Road

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23 Highland Road, Springfield, VT 05156 is a 6 bedroom, 8 bathroom, 6,506 sqft single-family home built in 1811. This property is not currently available for sale. 23 Highland Road was last sold on Jun 1, 2022 for $864,000 (3% lower than the asking price of $889,500). The current Trulia Estimate for 23 Highland Road is $842,400.