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317 Bebbington Road

Ashford, Connecticut 06278

ACTIVE$1,995,000

Reduced from $2,500,000

Beds
0
Baths
0
SqFt
Acres
153.10
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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WaterfrontPrice Reduced

About This Home

CROOKES ORCHARD - A LEGACY FARM OF EXTRAORDINARY BEAUTY AND OPPORTUNITY! One of Northeast Connecticut's most beloved agricultural destinations, presents an exceptionally rare opportunity to acquire 153 contiguous acres of working orchard, farmland, & scenic countryside. The property encompasses approximately 32 acres of improved cropland w/sprawling hay fields, picturesque ponds, & Bebbington Brook winding through the landscape, all abutting State Forest & Joshua's Trust protected land. More than 6,000 fruit trees, including 1,200 newly planted, yield 28 heirloom varieties of apples, peaches, & Asian pears. Carefully maintained orchard rows are supported by irrigation systems, while approximately 7 acres are enclosed by new 8-foot deer fencing w/3 double gates. A vibrant dahlia field further enhances the property's beauty & seasonal appeal. At the heart of the farm is the beautifully remodeled 3,601 SF retail farm store, long celebrated for its "Pick Your Own" traditions & broad assortment of locally grown & produced goods. Recent improvements include a turnkey commercial bakery, 2 walk-in coolers, updated office & restroom facilities, new HVAC, new roofs, partially replaced siding, new exterior doors, stone patios, and freshly painted exteriors. An attached glass greenhouse & additional hoop houses significantly extend the growing season. ***CONTINUE READING***

Key Facts

City/Town
Ashford
Property Type
Land
Days on Market
31 days
Beds
0
Baths
0 baths
Lot Size
153.10 acres
Property Taxes
$7,013 / Annually

Market Snapshot

The Ashford Market

Land · trailing 12 months

Median Days on Market

33

2 active listings

Median $ / Sq Ft

--

2 active listings

Sale-to-List Ratio

91.4%

5 sales

How this home compares

List Price

$2.00M

vs $1.06M median

88.2% above median

Price / Sq Ft

--

Median unavailable

Limited comparable data

Days on Market

31 days

vs 33 days median

2 days fresher than median

Based on 2 active and 5 closed sales (trailing 12 mo) of land in Ashford. Source: SmartMLS · As of July 28, 2026.

Location

317 Bebbington Road, Ashford, Connecticut

Property

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$11,421

per month

  • Principal & Interest$10,172
  • Property Taxes$584
  • Insurance$665
  • HOA$0

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

Location

City/Town
Ashford
County
Windham

Residence

Property Type
Land
Subtype
Agriculture

Exterior & Lot

Lot Size
153.10 acres
Zoning
RA
Waterfront
Direct waterfront
Waterfront Details
BrookViewAccess
Water Source
Private Well
Sewer
SepticSeptic Required
Lot Description
Some WetlandsTreedFarm LandBorders Open SpaceClearedRolling

Listing & Financials

Property Taxes
$7,013 / Annually
Days on Market
31
MLS #
24186879
MLS Status
Active

Similar Properties

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Listed By

Kiara Rusconi

(860) 573-3382

William Raveis Real Estate

(860) 633-0111

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:05 AM UTC.