A Crow’s Nest, Heated Kitchen Floors, and a Pool: Inside Waverly’s $365,000 Shepard House
A house with a crow’s nest already promises something out of the ordinary. Add lofty ceilings, fireplaces, and a kitchen with radiant heated floors, and the appeal becomes more personal: an old home with unusual spaces to explore and comforts to enjoy. 105 Chemung Street in Waverly, New York, is currently advertised at $365,000 by EXIT Realty Homeward Bound.
For readers searching for historic homes for sale in upstate New York, this property offers plenty to consider. Its substantial interior invites thoughts of long dinners, visiting friends, and rooms devoted to favorite pursuits. But the most interesting old houses deserve an honest reading, too. Here, the opportunity includes unfinished work—and understanding that work is essential to appreciating what the house could become.
The Backstory & Architectural Marvel
The current brokerage listing records an 1860 construction date, 4,430 square feet, five bedrooms, and two full bathrooms plus one half bathroom. It describes the property as the historic Shepard House, a brick Italianate Victorian. That name and architectural description come from the listing; an independently documented ownership history was not available in the sources reviewed.
There is an important wrinkle in the online records. The supplied Zillow page displays an earlier $310,000 sale in June 2025, along with different bedroom, bathroom, square-footage, and acreage figures. Its older description also calls the house Greek Revival.
For this article, the current MLS listing, #337361, provides the working details. Buyers should confirm the building measurements, parcel boundaries, and architectural history rather than assuming every portal describes precisely the same property configuration.
The current listing gives the land area as approximately 2.1 acres. That creates a different proposition from a compact village house: room to enjoy a landscape, but also grounds that require attention. realtor.com
The house’s attraction rests in how those generous spaces might feel when occupied. A large room can accommodate a gathering without making every evening a formal event; a quieter room can become a library, a work space, or simply somewhere to close the door.
Inside the Luxury/Unique Spaces
The current property details identify three fireplaces, hardwood and tile flooring, and a living room measuring approximately 22 feet 11 inches by 14 feet 10 inches. Separate dining spaces are also recorded.
Those proportions suggest several ways to furnish the house. A living room could hold a conversation area and a reading corner, while a dedicated dining room could give a long-loved table a permanent home.
For an old-house enthusiast, the pleasure may be in letting the rooms guide the decorating. Before choosing colors or buying furniture, spend time noticing where you would naturally sit, gather, and move through the house.
Fireplaces add atmosphere, but their condition matters as much as their appearance. A buyer would want to understand which units are operational and what inspection or servicing they need.
A Kitchen With Warmth Underfoot
The kitchen’s standout feature is radiant floor heating, according to the listing. It is a practical comfort that could make cold mornings more inviting without dominating the room visually. Zillow
Imagine preparing breakfast with a warm surface underfoot, then carrying a cup into another room as the household wakes. That small daily experience can be more persuasive than a long list of decorative upgrades.
A viewing should also test the ordinary essentials: counter space, storage, appliance condition, and the route between cooking and dining. A memorable kitchen still needs to work comfortably.
Bedrooms, Offices, and Unfinished Possibilities
The listed five-bedroom arrangement includes a first-floor bedroom. Two upstairs office spaces appear in the room schedule, offering additional flexibility for work or hobbies.
The description mentions potential for seven bedrooms, but that is a possibility rather than the verified bedroom count. Any conversion would need an assessment of layout, code requirements, and intended use.
It also reports that a second full bathroom is being remodeled and suggests adding a shower to the first-floor half bathroom. Neither should be treated as a completed improvement; prospective buyers should establish what has been finished and what remains. 
The Crow’s Nest and Workshop Potential
The crow’s nest gives the property an intriguing architectural talking point. Its condition, access, and permitted use deserve examination before imagining it as an everyday retreat.
Below the main rooms, the listing describes a walk-out basement with potential for workshop or storage use.
For someone who restores furniture or enjoys making things, that could be a meaningful advantage. Moisture control, electrical capacity, ventilation, and access would determine how useful it actually is.
A Pool With Work Ahead
The grounds include an inground pool, but the listing says it is awaiting a new liner. That makes it a project to assess rather than a ready-to-use summer amenity.
A pool inspection and repair estimate would help turn an appealing photograph into a realistic plan. The same approach applies to the wider landscape: decide which outdoor spaces you would use most, then understand the work needed to maintain them.
Market Context & Neighborhood Spotlight
Waverly provides a village setting with a historic downtown. New York State describes its central business district as containing independently owned shops, restaurants, service businesses, and community events. www.ny.gov
Outdoor recreation adds another dimension. Two Rivers State Park Recreation Area offers wooded terrain and views over the Chemung and Susquehanna river valleys. staffportal.parks.ny.gov
The property listing also places the house approximately 2.5 miles from Guthrie Robert Packer Hospital. Buyers considering the location for work should test the actual journey rather than relying only on mileage.
At $365,000 and 4,430 listed square feet, the asking price is approximately $82 per square foot. That ratio helps compare size, but it cannot establish value without considering condition, required repairs, and comparable completed sales.
Why Properties Like This Draw Interest / Investment Outlook
The appeal here is the combination of substantial space, distinctive architecture, and land within a village setting. It could attract a buyer who wants room for guests, creative pursuits, or a home office while accepting the responsibilities of an older building.
Waverly also has a documented revitalization story. In 2024, New York State announced nine projects associated with the village’s $4.5 million NY Forward award. This is useful community context, although it does not establish project completion or predict an individual home’s appreciation. www.governor.ny.gov
The strongest investment assessment would begin with the house itself:
- Establish the remaining bathroom work.
- Obtain a pool repair estimate.
- Inspect the roof, masonry, heating, and electrical systems.
- Confirm the included parcels and current property taxes.
- Compare recent sales of similarly sized homes.
These answers would reveal whether the asking price leaves room for the improvements a particular buyer considers necessary.
The Shepard House may appeal most to someone who wants an old home with substantial rooms and unusual features—and has the resources to address its unfinished work.
Its promise lies in the life those spaces could support: meals with friends, a dedicated workshop, a quiet upstairs office, and outdoor afternoons once the pool’s condition is resolved.
Which would draw you in first: the crow’s nest, the fireplaces, or the chance to give this old house its next chapter?
Current brokerage listing retrieved October 5, 2026: $365,000, represented by Steven Mandeville of EXIT Realty Homeward Bound, MLS #337361. Price, availability, and property details should be confirmed with the listing agent. EXIT Realty