# 399 W Main Street, Greenwood, IN 46142 > **TL;DR:** commercial, $479,000, built 1946. > A/C. Est. $2,562/mo. Listed 98 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $479,000 | | Year Built | 1946 | | Lot Size | 23,958 sqft (0.55 acres) | | Stories | 2 | | Property Type | Commercial (Other) | | Status | Active | | Days on Market | 98 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $2,422 | | Estimated Insurance | $140 | | **Total** | **$2,562** | ## Nearby Schools - **Middle:** Greenwood Middle School - **High:** Greenwood Community High Sch ## Key Amenities - A/C ## Property Highlights - Built in 1946 - 0.55 acre lot - 2 stories ## Description ### Agent Description Charming Historic Office Space - Prime Commercial Opportunity. Step into a piece of history with this beautifully preserved 1946 property, offering timeless charm combined with flexible commercial functionality. Currently operating as professional office space, this property also offers residential-use potential, making it a rare and versatile find. Original hardwood floors flow throughout the main level, setting the tone for the character and craftsmanship found in every room. The main floor features two private offices, ideal for meeting with clients or focused work, along with a welcoming living room/waiting area anchored by a classic fireplace - perfect for greeting guests or clients in comfort. A formal dining room and sun-drenched sunroom add further versatility for meetings, breakrooms, or private workspace. The full kitchen includes an eat-in breakfast nook, a wonderful amenity for staff lunches or client hospitality, and a full bathroom completes the main level. Upstairs, you'll find an additional private office plus a spacious loft area with room for yet another workspace - ideal for a growing team or additional departments - along with a second full bathroom for added convenience. Outside, the property offers 5 designated parking spaces with room for more, ensuring easy access for staff and clients alike. A generous 26' x 35' unfinished basement/garage with an overhead door and rear entry provides excellent storage, workshop, or additional utility space. Blending historic character with modern-day functionality, this property is a standout opportunity for a business seeking a distinctive home base full of warmth and personality. ## Location - **Address:** 399 W Main Street, Greenwood, IN 46142 - **County:** Johnson - **Coordinates:** 39.613439, -86.112296 - **Google Maps:** https://www.google.com/maps?q=39.613439,-86.112296 ## Listing Agent - **Name:** Craig Deboor - **Brokerage:** REAL BROKER, LLC - **Broker Phone:** (317) 614-5445 ## Photos ![399 W Main Street - Photo 1](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f4225389842r.jpg) ![399 W Main Street - Photo 2](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1066759214r.jpg) ![399 W Main Street - Photo 3](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2530542858r.jpg) ![399 W Main Street - Photo 4](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1931529051r.jpg) ![399 W Main Street - Photo 5](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2988444027r.jpg) ![399 W Main Street - Photo 6](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2913360110r.jpg) ![399 W Main Street - Photo 7](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f18437890r.jpg) ![399 W Main Street - Photo 8](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f611253319r.jpg) ![399 W Main Street - Photo 9](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f71553083r.jpg) ![399 W Main Street - Photo 10](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1120134399r.jpg) ![399 W Main Street - Photo 11](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1530008598r.jpg) ![399 W Main Street - Photo 12](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3196522558r.jpg) ![399 W Main Street - Photo 13](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2316925056r.jpg) ![399 W Main Street - Photo 14](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2195650080r.jpg) ![399 W Main Street - Photo 15](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2583804789r.jpg) ![399 W Main Street - Photo 16](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1570611644r.jpg) ![399 W Main Street - Photo 17](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f381978546r.jpg) ![399 W Main Street - Photo 18](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1195726807r.jpg) ![399 W Main Street - Photo 19](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3819170846r.jpg) ![399 W Main Street - Photo 20](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f882868198r.jpg) ![399 W Main Street - Photo 21](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f953240797r.jpg) ![399 W Main Street - Photo 22](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3236329096r.jpg) ![399 W Main Street - Photo 23](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f694660854r.jpg) ![399 W Main Street - Photo 24](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3537325827r.jpg) ![399 W Main Street - Photo 25](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1549894458r.jpg) ![399 W Main Street - Photo 26](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f124198411r.jpg) ![399 W Main Street - Photo 27](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2023855768r.jpg) ![399 W Main Street - Photo 28](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f863170289r.jpg) ![399 W Main Street - Photo 29](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f943230848r.jpg) ![399 W Main Street - Photo 30](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f4193887287r.jpg) ![399 W Main Street - Photo 31](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1986432859r.jpg) ![399 W Main Street - Photo 32](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1005912590r.jpg) ![399 W Main Street - Photo 33](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3422587578r.jpg) ![399 W Main Street - Photo 34](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3412747261r.jpg) ![399 W Main Street - Photo 35](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2608921833r.jpg) ![399 W Main Street - Photo 36](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2784464660r.jpg) ![399 W Main Street - Photo 37](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1582034450r.jpg) ![399 W Main Street - Photo 38](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f1896631337r.jpg) ![399 W Main Street - Photo 39](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2140138121r.jpg) ![399 W Main Street - Photo 40](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f23682326r.jpg) ![399 W Main Street - Photo 41](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2593753883r.jpg) ![399 W Main Street - Photo 42](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3293849641r.jpg) ![399 W Main Street - Photo 43](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f3011453104r.jpg) ![399 W Main Street - Photo 44](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2056216797r.jpg) ![399 W Main Street - Photo 45](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2397664039r.jpg) ![399 W Main Street - Photo 46](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f81516732r.jpg) ![399 W Main Street - Photo 47](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f2183339440r.jpg) ![399 W Main Street - Photo 48](http://lh.rdcpix.com/c0a74a4f98547cf3dcae831ccc04d15cl-f4156352815r.jpg) --- **MLS#:** 22117040 | **Updated:** 2026-10-29 **Source:** listhub *Copyright © 2026 Broker Listing Cooperative®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://staging.propertysimple.ai/listing/399-w-main-street-greenwood-in-46142-7c21775c58a645dbab94ddd2fa0bd1d4) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://staging.propertysimple.ai/listing/399-w-main-street-greenwood-in-46142-7c21775c58a645dbab94ddd2fa0bd1d4#listing", "url": "https://staging.propertysimple.ai/listing/399-w-main-street-greenwood-in-46142-7c21775c58a645dbab94ddd2fa0bd1d4", "name": "399 W Main Street, Greenwood, IN 46142", "description": "Charming Historic Office Space - Prime Commercial Opportunity. Step into a piece of history with this beautifully preserved 1946 property, offering timeless charm combined with flexible commercial functionality. Currently operating as professional office space, this property also offers residential-use potential, making it a rare and versatile find. Original hardwood floors flow throughout the main level, setting the tone for the character and craftsmanship found in every room. The main floor features two private offices, ideal for meeting with clients or focused work, along with a welcoming living room/waiting area anchored by a classic fireplace - perfect for greeting guests or clients in comfort. A formal dining room and sun-drenched sunroom add further versatility for meetings, breakrooms, or private workspace. The full kitchen includes an eat-in breakfast nook, a wonderful amenity for staff lunches or client hospitality, and a full bathroom completes the main level. Upstairs, you'll find an additional private office plus a spacious loft area with room for yet another workspace - ideal for a growing team or additional departments - along with a second full bathroom for added convenience. 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