Cobb Road
Cobb Road links Flying Point Road with the Wickapogue Road Historic District on Water Mill's western edge, past ca. 1900–1910 estate houses in the Town's 2014 survey.
Cobb Road runs through the western edge of Water Mill, in unincorporated Town of Southampton territory. It meets Flying Point Road and marks one end of the Wickapogue Road Historic District, which the State and National Registers list along Wickapogue Road between Narrow Lane and Cobb Road. Cobb was one of the small settlements combined in the nineteenth century to make the hamlet of Water Mill.
The road is short on public landmarks and long on early-twentieth-century estate architecture. The Town's 2014 draft historic survey placed four Cobb Road houses in a potential Water Mill Historic District and listed others as potential landmarks.
What the record shows
According to the 2014 draft Historic Resources Survey, prepared for the Town:
- 396 Cobb Road: a Craftsman and Tudor Revival house built around 1910 as part of a larger estate. 1 Little Cobb Road, a large Craftsman house with a shingled water tower, came from the same estate.
- 366 Cobb Road: a waterfront Arts & Crafts house that the survey says was reportedly designed by Grosvenor Atterbury around 1900.
- 326 Cobb Road: an octagonal shingled tower shaped like a windmill, apparently used as a residence, next to a larger Neoclassical and Colonial Revival house.
- 356 Cobb Road: listed in the potential district.
- 231 Cobb Road and 919 Cobb Road W: listed in a potential Water Mill Multiple Resource District. The survey describes the first as reportedly a Halsey house dating to the late eighteenth or early nineteenth century, and the second as a ca. 1880 farmhouse.
None of this is designation. The potential Water Mill district has not been adopted, so Cobb Road houses carry no Town historic-district review today. The survey matters because the Town works from it. The Bridgehampton district designated in December 2023 began as the same kind of survey finding.
The Wickapogue Road Historic District is different. It is a State and National Register listing, not a Town overlay. Register listing recognizes significance but does not by itself create local review of private alterations. Owners should still confirm with the Town before work on a property at the Cobb Road end of Wickapogue Road.
Land and water
Cobb Road is not an ocean road. One surveyed house is described as waterfront. Which water a given parcel touches, and whether the lot reaches it in fee or only has a view, has to come from the survey and the tax map.
Town of Southampton zoning governs. The zoning district, not the road, sets lot size, coverage and accessory-structure limits. Several Cobb Road houses were once part of a single larger estate. A buyer should read the filed subdivision map for covenants, clearing limits and shared driveways.
Buyer diligence
- Confirm whether the house is in the 2014 survey and in which potential district.
- Read the subdivision map and any covenants for estate-era lots.
- Establish water frontage, wetland setbacks and flood zone for any lot near the creeks or ponds.
- Check whether an architect attribution is documented or only "reported."
- Pull certificates of occupancy for towers, carriage houses and other outbuildings. Their lawful use is a separate question from their age.
Nearby lanes
Flying Point Road carries Cobb Road traffic to the ocean. Halsey Lane runs south from the Water Mill green. Mecox Road and Bay Lane lead to Mecox Bay. Hamlet context: Water Mill. For the incorporated village to the west, see Southampton Village.
Considering a Cobb Road property?
Request a private pricing review from The Roebling Research Desk for the specific Cobb Road parcel: estate history and survey status, documented authorship, water and wetland conditions, subdivision covenants and the recorded sales that genuinely compare.
Recorded sales
Recorded sales through July 2026
23 recorded arm’s-length sales of 21 distinct properties since October 2016 (16 house, 5 partial interest, 2 land).
3 single-parcel house sales in 2023–2025 — too few for a range or median; listed below.
Historical transaction median, Nov 15, 2016 to Feb 13, 2026: $5,600,000 (16 single-parcel house sales). A decade-wide figure, not a current value.
| Sale date | Address | Type | Recorded price | Beds (roll) | Built (roll) | Flood zone |
|---|---|---|---|---|---|---|
| Feb 13, 2026 | 317 Cobb Road | House | $6,100,000 | 4 | 2005 | X |
| Sep 16, 2025 | 112 Cobb Road | House | $3,900,000 | 3 | 1994 | X |
| Nov 3, 2023 | 360 Cobb Road | House | $5,000,000 | 3 | 1994 | X |
| Nov 3, 2023 | 366 Cobb Road | House | $14,000,000 | 4 | 2001 | X |
| May 25, 2022 | 158 Cobb Road | Land · house on the 2025 roll† | $3,100,000 | 7 | 2025 | X |
| Mar 24, 2022 | 349 Cobb Road | House | $5,100,000 | 3 | 2012 | X |
| Sep 17, 2021 | 88 Cobb Road | House | $6,500,000 | 4 | 2011 | X (0.2%) |
| May 6, 2021 | 308 Cobb Road | House | $10,800,000 | 5 | 2005 | X |
| Jan 22, 2021 | 89 Cobb Road | House | $3,755,000 | 4 | 2010 | X (0.2%) |
| Apr 22, 2020 | 209 Cobb Road | House | $2,700,000 | 5 | 1996 | X |
| Feb 12, 2019 | 396 Cobb Road | House | $5,100,000 | 2 | 2023 | X |
| May 29, 2018 | 374 Cobb Road | House | $8,150,000 | 8 | 2015 | X |
| Apr 13, 2018 | 377 Cobb Road | House | $7,700,000 | 7 | 2022 | X |
| Sep 7, 2017 | 80 Cobb Road | House | $7,400,000 | 7 | 2017 | X (0.2%) |
| Aug 1, 2017 | 89 Cobb Road | House | $1,900,000 | 4 | 2010 | X (0.2%) |
| May 31, 2017 | 68 Cobb Road | House | $7,832,500 | 5 | 2012 | AE |
| Apr 26, 2017 | 334 Cobb Road | Partial interest · package of 6 parcels | $6,000,000* | 3 | 2004 | — |
| Apr 26, 2017 | 336 Cobb Road | Partial interest | $2,000,000 | — | — | X |
| Apr 26, 2017 | 320 Cobb Road | Partial interest | $6,000,000 | 4 | 2000 | X |
| Apr 26, 2017 | 318 Cobb Road | Partial interest | $2,000,000 | — | — | X |
| Apr 26, 2017 | 324 Cobb Road | Partial interest | $6,000,000 | 5 | 1992 | X |
| Apr 26, 2017 | 316 Cobb Road | Land | $1,500,000 | — | — | X |
| Nov 15, 2016 | 158 Cobb Road | House | $2,275,000 | 7 | 2025 | X |
* One price for several parcels; it is not the price of the listed address alone, and it is left out of every median. † Recorded as land when it sold (vacant, or a house the buyer took down); the 2025 assessment roll now shows a house. Land sales never enter a house median. Sale date is the date of sale on the transfer form. Beds and year built come from the assessment roll where it records them. Source: New York State real property transfer record (form RP-5217, filed with every deed), arm's-length sales as flagged by the state. These figures are a separate series from the Roebling Index, which is built from published market reports. How these tables are built.
Flood and coastal exposure
5 of 55 residential and vacant parcels sit in FEMA’s 1% annual-chance flood area (zones VE, AE, A or AO), where a mortgage from a federally regulated or insured lender requires flood insurance on the building.
| FEMA zone | Parcels | What it means for an owner |
|---|---|---|
| AE — 1% annual-chance flood, base flood elevation set | 5 | A 1% chance of flooding in any year (about 26% over a 30-year mortgage). Flood insurance is required with a federally backed mortgage. A new or substantially improved house must have its lowest floor at or above the base flood elevation shown on the map; local codes can require more. |
| X (shaded) — 0.2% annual-chance flood | 5 | A 0.2% annual chance of flooding (the “500-year” flood). Flood insurance is not federally required, but it is usually available at lower rates and a lender may still ask for it. |
| X — minimal flood hazard | 45 | Outside the mapped flood areas. Flood insurance is not federally required. Flooding can still happen from heavy rain and drainage. |
Loans. In zones VE, AE, A and AO, any mortgage made, insured or bought by a federally regulated lender, Fannie Mae, Freddie Mac, FHA or VA requires flood insurance on the building for the life of the loan. A lender can require it in zone X as well. A cash buyer is not required to insure.
Premiums. Since 2021 the National Flood Insurance Program prices each house on its own features (elevation, distance to water, cost to rebuild), so the zone is a starting point, not the price. Private flood policies are an alternative. An elevation certificate is the document every insurer asks for.
Renovating. In the 1% flood area, if work on a house costs half or more of the building’s market value, or a storm damages it that badly, the whole house must be brought up to current flood rules, which usually means raising it. Plan a renovation budget against that line.
Zone at each tax parcel’s center point; part of a parcel can sit in a different zone. Source: FEMA National Flood Hazard Layer (Suffolk County, map 36103C), retrieved 2026-11-12; flood insurance rate map panels effective Sep 25, 2009. A parcel-level determination needs the current map panel, any Letter of Map Revision or Amendment, and an elevation certificate. State coastal erosion hazard areas are mapped separately and are not shown here. Flood and coastal-erosion guide.
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What buying, owning or selling here costs.
Peconic Bay CPF, mansion tax, title, MRT.
NY transfer tax, commission, attorney.
Taxes, flood and wind coverage, septic, upkeep.
Sell now, or rent the seasons and sell later.
A summer rental against owning the house.
Federal, NY, NYC and the nonresident payment.
Own on Cobb Road?
Request a pricing review of your property, prepared from the recorded sales on and around the road and what the public record shows about the parcel. Or ask about buying here.
646.939.7375 · c.cohen@compass.com
Considering a Hamptons purchase or sale?
A 30-minute consultation is the right starting point — the specific place, road or property you’re weighing, what the public record does and doesn’t settle, the diligence that matters on the South Fork, and connecting you with the right Compass East End specialist.
The Roebling Team at Compass is led by Corey Cohen, a New York licensed associate real estate broker. For the Hamptons we bring along a vetted Compass agent who specializes in the East End. This page and its calculators are research, not an offer of representation.