Discover the timeless charm and exceptional potential of the Chestnut House Bed & Breakfast, a distinctive historic property nestled in the heart of The Village at Winona. Built in 1906, this beautiful Princess Anne style home blends historic character with modern comforts, offering a unique opportunity to own a well-established hospitality property in one of the area's most desirable destinations. Featuring four thoughtfully appointed guest suites, each with a private bath and inviting accommodations, the Chestnut House provides a welcoming experience for visitors seeking a memorable stay. The home's historic architecture and enduring charm create an atmosphere that sets it apart from traditional lodging options. Adding even greater value and versatility to this exceptional offering is a separate, newly updated one bedroom, one bath caretaker's home. Complete with all appliances and offered turnkey, this additional residence is ready for immediate use and provides comfortable on-site living for an owner operator, innkeeper, or caretaker. Ideally located within walking distance of the shops, restaurants, and attractions of The Village at Winona, the property also offers convenient access to Winona Lake, Grace College, and the surrounding area's year-round activities and events. Whether you're looking to continue the bed and breakfast's hospitality tradition, invest in a unique income producing property, or explore new possibilities, this rare offering combines historic appeal, a desirable location, and the added benefit of a move in ready second residence. Two homes. One exceptional opportunity. Experience the charm, character, and possibilities of the Chestnut House Bed & Breakfast in Winona Lake, Indiana.
Active
$899,900
806 & 808 Chestnut St, Winona Lake, IN 46590
5beds
4,882sqft
Single Family Residence
Built in 1904
9,147 Square Feet Lot
$857,200 Zestimate®
$--/sqft
$-- HOA
What's special
Princess anne style homeHistoric architectureComfortable on-site livingEnduring charmComplete with all appliancesInviting accommodations
- 18 days
- 1,479
- 61
Zillow last checked:
Listing updated:
Listed by:
Julie Hall Cell:574-268-7645,
Patton Hall Real Estate
Source: IRMLS,MLS#: 202644202
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
- Main level bedrooms: 1
Bedroom 1
- Level: Upper
Bedroom 2
- Level: Upper
Dining room
- Level: Main
- Area: 192
- Dimensions: 12 x 16
Kitchen
- Level: Main
- Area: 156
- Dimensions: 12 x 13
Living room
- Level: Main
- Area: 221
- Dimensions: 13 x 17
Office
- Level: Upper
- Area: 55
- Dimensions: 11 x 5
Heating
- Natural Gas, Forced Air
Cooling
- Central Air
Appliances
- Included: Dishwasher, Microwave, Refrigerator, Washer, Dryer-Electric, Double Oven, Electric Oven, Electric Range, Gas Water Heater, Water Softener Owned
- Laundry: Washer Hookup
Features
- Countertops-Solid Surf, Eat-in Kitchen, Entrance Foyer, Kitchen Island, Natural Woodwork, Tub/Shower Combination, Formal Dining Room, Custom Cabinetry
- Flooring: Hardwood, Carpet, Ceramic Tile
- Doors: Six Panel Doors
- Windows: Window Treatments
- Basement: Crawl Space,Full,Unfinished,Block
- Number of fireplaces: 2
- Fireplace features: Living Room, 1st Bdrm
Interior area
- Total structure area: 5,709
- Total interior livable area: 4,882 sqft
- Finished area above ground: 4,430
- Finished area below ground: 452
Video & virtual tour
Property
Parking
- Parking features: Paver Block
- Has uncovered spaces: Yes
Features
- Levels: Three Story
- Stories: 3
- Patio & porch: Deck, Porch Covered, Porch, Screened
- Fencing: None
Lot
- Size: 9,147 Square Feet
- Dimensions: 111X80
- Features: 0-2.9999, City/Town/Suburb, Near College Campus, Near Walking Trail, Landscaped
Details
- Additional parcels included: 4311-15-300-361.000-033
- Parcel number: 431115300352.000033
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Roof: Asphalt,Metal,Shingle
Condition
- New construction: No
- Year built: 1904
Utilities & green energy
- Electric: NIPSCO
- Gas: NIPSCO
- Sewer: City
- Water: City, Indiana American Water Co
Community & HOA
Community
- Subdivision: None
Location
- Region: Winona Lake
Financial & listing details
- Annual tax amount: $10,132
- Date on market: 10/26/2026
- Listing terms: Cash,Conventional
Estimated market value
$857,200
$814,000 - $900,000
$3,550/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/26/2026 | Listed for sale | $899,900 |
Source:  IRMLS #202644202 Report a problem | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 46590
Nearby schools
Schools provided by the listing agent
- Elementary: Jefferson
- Middle: Edgewood
- High: Warsaw
- District: Warsaw Community
Source: IRMLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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