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806 & 808 Chestnut Street, 
Winona Lake, IN 46590

$899,900


5

Beds


6

Baths


4,882

Sq Ft


Single Family


Virtual Tour

Active

Listed by

Julie Hall, Cell: 574-268-7645

Patton Hall Real Estate

Last updated:

October 31, 2026, 09:30 PM

MLS#

202644202

Source:

Indiana Regional MLS

About This Home

806 & 808 Chestnut Street

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.

Home Facts

Single Family

6 Baths

5 Bedrooms

Built in 1904

Subdivision & Development:

None

Price Summary

899,900

$184 per Sq. Ft.

MLS #:

202644202

Last Updated:

October 31, 2026, 09:30 PM

Added:

10 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

5

Bathrooms

Total Bathrooms:

6

Full Bathrooms:

5

Interior

Living Area:

4,882 Sq. Ft.


Structure

Structure

Architectural Style:

Three Story

Building Area:

5,709 Sq. Ft.

Year Built:

1904


Lot

Lot Size (Sq. Ft):

9,148


Finances & Disclosures

Finances

Price:

$899,900

Price per Sq. Ft:

$184 per Sq. Ft.

Source:Indiana Regional MLS
IRMLS information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IRMLS Data is deemed reliable but is not guaranteed accurate by the MLS. IRMLS information provided by the Indiana Regional MLS. Copyright 2026 Indiana Regional MLS LLC.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.