29 Head Road, Callicoon, NY 12723
Property image
Property image
OFF MARKET

29 Head Road
Callicoon, NY 12723

  • 3 Beds
  • 2 Baths
  • 4,311 sqft (on 42.66 acres)
3 Beds
2 Baths
4,311 sqft
(on 42.66 acres)

Local Information

  • Map ViewExplore the area around 29 Head Road.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1948
Lot Size
42.66 acres
Living Area
4,311 sqft
Parking
2 Car Garage

About this House

Bluestone Barn may be the Mack Daddy of converted barns. This one-of-a-kind dwelling is sited on 42.66 bucolic acres with an eye-popping vista over its private swimming pond and out to the area’s scenic rolling hills. (All new Andersen windows added summer 2023, including 2 new glass sliding doors out to new decks off living room and primary bedroom). This is a warm, welcoming home created from a cavernous 4,000+ square foot space by enclosing rooms at either end, and dividing up the huge remaining open space in the middle into discrete areas with defined purposes. Then they utilized the huge overhead space to build 3 lofts, and the result is a series of dynamic, and often surprisingly intimate, character-filled spaces. You'll be wowed by the 29' ceiling and the stone fireplace that soars to its apex. Multiple large south-facing windows and skylights illuminate the room beautifully, highlighting the hand hewn beams, fireplace and hemlock floors. Moving around the fireplace, which is a central focal point, is the dining area and kitchen. Perhaps the most exciting spaces are overhead. Wide stairs lead to a long catwalk that connects two deep lofts at either side, one of which has a ladder to yet a third, which serves as a dedicated bedroom. Primary bedroom (en suite), guest bedroom and second bathroom are down a hall with a sauna. The “basement” runs the full length of the house; attached 2-car garage with 1,000 sf room at the back. The solar array (on the roof), is a 10.2 kW system with net metering. Numerous meadows on gently rolling hills facilitate extended views. Patio was built on the remains of an old stone silo. Taxes are for 74 (not 42.66) acres, and do not include reductions for solar and agricultural tax abatements.
29 Head Road, Callicoon, NY 12723 is a 3 bedroom, 2 bathroom, 4,311 sqft single-family home built in 1948. It last sold for $1,150,000 on Sep 23, 2024 (8% below the $1,250,000 asking price). It is currently off market. The Trulia Estimate rent is $3,351/month.

Home Details for 29 Head Road

Active Status

MLS Status: Closed

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Attic, Basement, Den, Dining Room, Family Room, Great Room, Kitchen, Living Room, Loft, Other Room, Utility Room, Workshop
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 4311 Square Feet
Appliances & Utilities
Appliances: Other, Water Heater, Washer, Refrigerator, Range, Dryer, DishwasherDishwasherDryerRefrigeratorWasher
Heating & Cooling
Heating: Propane,Radiant,Radiant Floor,WoodHas HeatingHeating Fuel: Propane
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Living Room, Stone, Wood BurningHas a Fireplace
Windows, Doors, Floors & Walls
Window: Skylight(s)Door: French DoorsFlooring: Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Floors: Ceramic Tile, Hardwood
View
Has a ViewView: Mountain(s), Water

Exterior Features

Exterior Home Features
Roof: Asphalt ShinglePatio / Porch: PatioOther Structures: Shed(s)
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Has a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Frontage
Road Surface Type: Gravel
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 4311 Square Feet

Property Information

Year Built
Year Built: 1948
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: BarndominiumArchitecture: Barndominium
Building
Construction Materials: Frame, Wood SidingNot a New Construction
Property Information
Parcel Number: 483200038 0001005000

Price & Status

Price
List Price: $1,250,000
Status Change & Dates
Off Market Date: Mon Aug 05 2024

Location

Direction & Address
City: Callicoon
School Information
High School District: Sullivan West Central Schools

Building

Building Area
Building Area: 4311 Square Feet

Lot Information

Lot Area: 42.66 Acres

Miscellaneous

Mls Number: 20223348Water ViewWater View: WaterAbove Grade Unfinished Area: 4311
Last check for updates: about 7 hours ago
Listed by Jennifer Grimes, (845) 593-9524
Country House Realty, Inc.
Bought with: NON MLS OFFICE, Anderson Agency
Source: HVCRMLS, MLS#20223348

Price History for 29 Head Road

DatePriceEventSource
09/23/2024$1,150,000Sold
HVCRMLS #20223348
08/05/2024$1,250,000PendingHVCRMLS #20223348
06/25/2024$1,250,000PriceChange
HVCRMLS #20223348
10/04/2023$1,375,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6214963
08/03/2023$1,500,000Listed For SaleHVCRMLS #20223348
07/12/2023ListingRemovedOneKey® MLS as distributed by MLS GRID #H6214963
01/08/2023$1,500,000PriceChange
OneKey® MLS as distributed by MLS GRID #H6214963
10/19/2022$1,650,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6214963
09/17/2022ListingRemovedOneKey® MLS as distributed by MLS GRID #H6141709
09/17/2021$2,499,000Listed For SaleOneKey® MLS as distributed by MLS GRID #H6141709

Market trends in Callicoon

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
22
3MoM
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Property Tax and Assessment

Year2022
Tax
Assessment$878,600
Home facts updated by county records

Comparable Sales for 29 Head Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
256 Pleasant Valley Road, Callicoon, NY
0.66
Single-Family Home
$385,000
12/18/25
2
2
1,010
582 N Branch Hortonville Road, North Branch, NY
0.81
Single-Family Home
$270,000
11/20/25
4
2
1,616
146 Buddenhagen Road, Callicoon, NY
1.36
Single-Family Home
$800,000
01/26/26
3
2
1,900
5 Hess Road, Callicoon, NY
1.07
Single-Family Home
$462,500
05/21/26
4
3
2,631
463 County Road 131, Fremont Center, NY
1.13
Single-Family Home
$340,000
05/22/26
3
2
1,056
54 Graby Road, Callicoon, NY
1.39
Single-Family Home
$350,000
10/24/25
3
2
1,400
858 N Branch Hortonville Road, North Branch, NY
1.28
Single-Family Home
$457,500
10/28/25
3
3
1,500
649 County Road 95, North Branch, NY
2.24
Single-Family Home
$885,000
10/23/25
3
2.5
2,161
136 Kautz Road #136, Callicoon, NY
1.60
Single-Family Home
$430,000
11/20/25
3
1.5
1,700

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Assigned Schools

These are the assigned schools for 29 Head 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 Callicoon

At least 6 Trulia users voted on each feature.

  • 100 % Say car is needed

  • 86 % Say it's dog friendly

  • 83 % Say there's wildlife

  • 71 % Say neighbors are friendly

  • 71 % Say it's walkable to grocery stores

  • 67 % Say streets are well-lit

  • 64 % Say there are community events

  • 62 % Say yards are well-kept

  • 60 % Say parking is easy

  • 60 % Say kids play outside

  • 56 % Say it's walkable to restaurants

  • 56 % Say people would walk alone at night

  • 55 % Say there are sidewalks

  • 50 % Say there's holiday spirit

  • 38 % Say they plan to stay for at least 5 years

  • 25 % Say it's quiet

Sourced by Trulia users. Learn more about our methodology.
  • Fceisenberg
    "The first 5 miles in the morning— and last at night — wind all no a curvy country road next to a scenic creek. Great way to start and end the day."
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IDX information © 2026 by the Hudson Valley Catskill Region MLS. All Rights Reserved. The data relating to real estate on this website comes in part from the IDX of the Hudson Valley Catskill Region MLS.
Information is deemed reliable but is not guaranteed accurate by the MLS. IDX information is provided exclusively 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.