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A rare offering on the shores of Little Pleasant Bay, 40 Tom's Hollow is a generational waterfront estate encompassing nearly four acres of bucolic landscape with an expansive shoreline, private sandy beach, and iconic boathouse. A winding drive leads through a serene coastal setting to a timeless center-entrance Colonial, where soaring ceilings and panoramic bay views set the tone. The cathedral-ceilinged great room, with pass-through hearth, forms the heart of the home--flanked by a custom kitchen and gracious dining area, perfectly positioned to capture the beauty beyond. A first-floor primary suite offers privacy and comfort, while separate guest quarters provide flexibility for extended stays. The finished walkout lower level adds space for recreation, gatherings, or overflow guests--all opening to a lawn that invites entertaining and the potential for a pool. Outside, a wide stretch of shoreline allows for private beach access, and mooring rights open the door to water-sport adventures. The historic boathouse, brimming with potential, anchors the property in authentic Cape Cod tradition. This is a rare legacy estate where nature and coastal elegance live in quiet harmony.
General Information for 40 Toms Hollow Lane Orleans, MA 02653 |
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| Town | Orleans |
| Village | Orleans |
| County | Barnstable |
| Stories | 2 |
| SQFT | 4,000 |
| Status | Available |
| Listing Number | 22501262 (CCIMLS) |
Rooms Information for 40 Toms Hollow Lane Orleans, MA 02653 |
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| Family Room | 0X0 |
| Kitchen Features | 0X0 |
| Dining Room | 0X0 |
| Bedroom | 0X0 |
| Bedroom 1 | 0X0 |
| Bedroom 2 | 0X0 |
| Bedroom 3 | 0X0 |
| Bedroom 4 | 0X0 |
Interior Information for 40 Toms Hollow Lane Orleans, MA 02653 |
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| Basement | Finished |
| Interior Features | Sound System |
Exterior Information for 40 Toms Hollow Lane Orleans, MA 02653 |
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| Lot Size | 3.84 acres |
| Construction | Shingle Siding |
| Garage | 3 Car Garage |
| Water | Well |
| Sewer | Private Sewer |
| Exterior Features | Outdoor Shower |
Neighborhood Information for 40 Toms Hollow Lane Orleans, MA 02653 |
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| Ocean/River/Lake Features | Little Pleasant Bay |
Schools information for 40 Toms Hollow Lane Orleans, MA 02653 |
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| Elementary | Nauset |
| Middle | Nauset |
| High | Nauset |
| General Area Public, Private School and College Information | |
Miscellaneous Information for 40 Toms Hollow Lane Orleans, MA 02653 |
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| Year Built | 1999 |
| Association Fee | 0 |
| Taxes | $33,210 /Yr |
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| Condo | Data |
|---|---|
| Units | 6,749 |
| Avg Price | $950,196 |
| Avg Days Listed | 96 |
| Total New Listings | 1 |
| House | Data |
|---|---|
| Units | 12,415 |
| Avg Price | $1,281,740 |
| Avg Days Listed | 80 |
| Total New Listings | 6 |
| Multi-Family | Data |
|---|---|
| Units | 2,042 |
| Avg Price | $1,290,923 |
| Avg Days Listed | 101 |
| Total New Listings | 0 |
For a more detailed market analyis one of our real estate agents can provide you with a full report.
| Address | Closing Date | List Price | Closing Price | % of List Price |
|---|---|---|---|---|
| 48 Namequoit Road Orleans, MA 02653 |
12/31/2024 | $2,750,000 | $2,550,000 | 93% |
| 190 Route 6A 3A Orleans, MA 02653 |
12/30/2024 | $324,900 | $315,000 | 97% |
| 310 S Orleans Road 3C Orleans, MA 02653 |
12/23/2024 | $549,500 | $549,500 | 100% |
| 33 Clayton Circle Orleans, MA 02653 |
12/23/2024 | $799,900 | $800,000 | 100% |
| 136 Main Street Orleans, MA 02653 |
12/20/2024 | $899,000 | $889,500 | 99% |
| 188 Rock Harbor Road Orleans, MA 02653 |
12/20/2024 | $1,049,000 | $1,049,000 | 100% |
| 24 Old Colony Way 11 Orleans, MA 02653 |
12/19/2024 | $390,000 | $400,000 | 103% |
| 87 Captain Linnell Road Orleans, MA 02653 |
12/19/2024 | $900,000 | $824,000 | 92% |
| 57 Route 6A Orleans, MA 02653 |
12/16/2024 | $325,000 | $300,000 | 92% |
| 19 Kings Way Orleans, MA 02653 |
12/12/2024 | $765,000 | $760,000 | 99% |
| 33 Mill Pond Road Orleans, MA 02653 |
12/05/2024 | $795,000 | $795,000 | 100% |
| 17 Hidden Valley Road Orleans, MA 02653 |
12/04/2024 | $925,000 | $925,000 | 100% |
| 9 Fox Ridge Drive Orleans, MA 02653 |
11/27/2024 | $1,195,000 | $1,115,000 | 93% |
| 82 Main Street Orleans, MA 02653 |
11/22/2024 | $1,495,000 | $1,395,000 | 93% |
| 65-67 Towhee Lane Orleans, MA 02653 |
11/19/2024 | $4,500,000 | $4,100,000 | 91% |
| 260 Tonset Road Orleans, MA 02653 |
11/15/2024 | $1,200,000 | $1,150,000 | 96% |
| 45 Mill Pond Road Orleans, MA 02653 |
11/15/2024 | $2,399,000 | $2,200,000 | 92% |
| 27 Grandview Drive Orleans, MA 02653 |
11/14/2024 | $2,199,900 | $1,850,000 | 84% |
| 5 Northwood Drive Orleans, MA 02653 |
11/13/2024 | $1,749,000 | $1,710,000 | 98% |
| 29 Pond Road Orleans, MA 02653 |
11/12/2024 | $980,000 | $970,000 | 99% |
| 79 Finlay Road Orleans, MA 02653 |
11/09/2024 | $11,400 | $11,400 | 100% |
| 24 Camp Road Orleans, MA 02653 |
11/06/2024 | $1,845,000 | $1,810,000 | 98% |
| 14 Pleasant View Drive Orleans, MA 02653 |
11/01/2024 | $1,200,000 | $1,200,000 | 100% |
| 33 Sea Mist Drive Orleans, MA 02653 |
11/01/2024 | $2,975,000 | $2,600,000 | 87% |
| 27 Grannys Lane Orleans, MA 02653 |
10/30/2024 | $1,300,000 | $1,220,000 | 94% |
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Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Cape Cod & Islands Multiple Listing Service, Inc. Detailed information about real estate listings held by brokerage firms other than Kinlin Grover Compass include the name of the listing broker. Neither the listing company nor Kinlin Grover Compass shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2025 Cape Cod & Islands Multiple Listing Service, Inc. All rights reserved.
This site was last updated 07/16/2025. All properties are subject to prior sale, changes, or withdrawal.
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