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148 & 153 Wallingford Road

Durham, Connecticut 06422

ACTIVE$4,100,000
Beds
0
Baths
0
SqFt
Acres
414.50
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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About This Home

The Greenbacker Brookfield is one of the largest farms now on the Connecticut market with over 400 acres. It has been in operation for over 100 years and is ready now for a new multi-generation family to take the reins or for a progressive investor. There is ample accommodation with 7 houses that have 29 bedrooms for the family to share. (The average size farm in CT is approximately 80 acres). The current owners are using 4 houses and renting 3 other homes. The investor agriculture buyer may also generate rental income from the farm's other rental property; 1. a Two story 35x50 horse barn, 2.a 35x80 stable with 1.5 story horse stalls. 3 a. Barn with double row stalls and indoor riding arena, 4. a 4-bay garage, 5. Dairy barn, and Chicken coops, etc.. These items may also be considered depreciable property (see your tax advisor). Other sources of income from the farm would include renting land for; 1, growing crops (92 acres of cropland leased, currently), 2, Durham Fair parking. 3, pastureland (20 acres of pasture leased, currently), 4, hunt club (land leased currently), 5, equestrian rental (stable & indoor/outdoor riding, currently leased) and for dairy farming. Potential income may come from establishing a farm stand, growing grapes/ winery, Christmas tree sales, blue berries, and more. The State of Connecticut Conservation Restriction requires this property to be 'agriculture in nature' according to development rights the state acquired approximately 70 years ag

Key Facts

City/Town
Durham
Property Type
Land
Days on Market
812 days
Beds
0
Baths
0 baths
Lot Size
414.50 acres
Property Taxes
$15,052 / Annually

Market Snapshot

The Durham Market

Land · trailing 12 months

Median Days on Market

33

3 active listings

Median $ / Sq Ft

--

3 active listings

Sale-to-List Ratio

102.6%

1 sale

How this home compares

List Price

$4.10M

vs $199,000 median

20.6× the median

Price / Sq Ft

--

Median unavailable

Limited comparable data

Days on Market

812 days

vs 33 days median

779 days longer than median

Based on 3 active and 1 closed sales (trailing 12 mo) of land in Durham. Source: SmartMLS · As of July 27, 2026.

Location

148 & 153 Wallingford Road, Durham, Connecticut

Property + 2 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$23,526

per month

  • Principal & Interest$20,905
  • Property Taxes$1,254
  • Insurance$1,367
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Durham
County
Middlesex

Residence

Property Type
Land
Subtype
Agriculture

Exterior & Lot

Lot Size
414.50 acres
Zoning
FR
Waterfront Details
Not Applicable
Water Source
Private WellShared Well
Sewer
SepticShared Septic
Lot Description
Some WetlandsFarm LandRolling

Listing & Financials

Property Taxes
$15,052 / Annually
Days on Market
812
MLS #
24015202
MLS Status
Active

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Listed By

Gary Dobratz

(203) 213-9097

Century 21 AllPoints Realty

(203) 265-1931

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/27/2026 at 7:25 AM UTC.