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One of Hampton's most treasured waterfront estates, 1500 Chesapeake Avenue offers a rare opportunity to own a historic landmark overlooking Hampton Roads Harbor and the Chesapeake Bay. Originally built in 1900 by Hampton entrepreneur Captain John C. Robinson and later known as the Dorothy Rouse-Bottom Estate, this remarkable residence has been meticulously restored while preserving its timeless craftsmanship and architectural character. Set on approximately 1.23 landscaped acres, the home offers nearly 8,000 square feet of living space, including a private guest suite above the detached garage with a full bath and an additional half bath below. Featuring seven bedrooms, six full and two half baths, and additional first-level flex rooms ideal for guests, offices, or multi-generational living, the home showcases grand formal rooms, exceptional millwork, original moldings, stained glass, elegant lighting, soaring ceilings, and five working fireplaces. Beautifully updated bathrooms complement the historic character, while the gourmet kitchen features an iconic Aga range, Smallbone English cabinetry, premium appliances, a butler's pantry, and abundant natural light. The lower level provides recreation space, storage, and direct access to a private waterfront fitness room or flex space connected by a breezeway. Outside, English-inspired gardens, brick walkways, wrought iron fencing, fountains, an expansive covered porch with panoramic harbor views, and a commercial-scale pier with an enclosed Tidetamer boat lift and dual 10,000-pound lifts create an extraordinary waterfront setting. Ideally located along historic Chesapeake Avenue near Fort Monroe, Hampton University, downtown Hampton, marinas, and waterfront dining, this legacy estate is one of Coastal Virginia's most admired waterfront homes.
| DAYS ON MARKET | 3 | LAST UPDATED | 8/5/2026 |
|---|---|---|---|
| TRACT | Wythe | YEAR BUILT | 1900 |
| COMMUNITY | 124 - Hampton | GARAGE SPACES | 2.0 |
| COUNTY | Hampton | STATUS | Active |
| PROPERTY TYPE(S) | Single Family |
| Elementary School | Hunter B. Andrews |
|---|---|
| Jr. High School | C. Alton Lindsay |
| High School | Hampton |
| ADDITIONAL DETAILS | |
| AIR | Central Air, Zoned |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Gas Cooktop, Gas Water Heater, Microwave, Oven, Refrigerator, Washer |
| AREA | 124 - Hampton |
| BASEMENT | Crawl Space, Full, Walk-Out Access, Yes |
| CONSTRUCTION | Brick, Frame, Wood Siding |
| EXTERIOR | Dock, Storage |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Forced Air, Natural Gas, Radiant, Zoned |
| INTERIOR | Beamed Ceilings, Bookcases, Built-in Features, Granite Counters, High Ceilings, Kitchen Island, Walk-In Closet(s) |
| LOT | 1.23 acre(s) |
| LOT DESCRIPTION | Level, Waterfront |
| PARKING | Circular Driveway, Driveway, Detached, Garage, Garage Door Opener, Off Street, Paved |
| POOL DESCRIPTION | None |
| SEWER | Public Sewer |
| STORIES | 3+ |
| STYLE | Colonial, Victorian |
| SUBDIVISION | Wythe |
| TAXES | 20338.74 |
| VIEW | Yes |
| VIEW DESCRIPTION | Water |
| WATER | Public |
| WATER ACCESS | Hampton Roads Harbor, James River |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | River Front, Navigable Water, Waterfront |
| ZONING | R13 |
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Listed with Shaheen Ruth Martin & Fonville
All or a portion of the multiple Listing information is provided by the Central Virginia Regional Multiple Listing Service, LLC, from a copyrighted compilation of Listings. All CVR MLS information provided is deemed reliable but is not guaranteed accurate. The compilation of Listings and each individual Listing are ©2026 Central Virginia Regional Multiple Listing Service, LLC. All rights reserved.
IDX information is provided exclusively for consumers’ personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing
Last Updated: 8/6/26 3:28 AM PDT
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