Pennsy Rail Trail Homes for Sale

The Pennsy Rail Trail is so named because of its historic roots in the Pennsylvania Railroad. The track was pulled up in 1982, after providing rail service for the folks in Indiana and many other states from 1853 until 1921, when the line was abandoned. The Greenfield, Indiana portion of the Pennsy Trail connects to Cumberland and Indianapolis' Pleasant Run Trail, though portions of this multi-purpose trail are still under construction.

Never miss a new listing near the Pennsy Rail Trail!

Latest Pennsy Rail Trail Homes for Sale

181 N 600 W Road, Greenfield, IN 46140

181 N 600 W Road, Greenfield, IN 46140

21.04 acres out of 24.04 acres are located in Sugar Creek Township and are zoned CN commercial zoning! The remaining 3.0 Acres are located in Buck Creek Township and...

0 Beds 0 Bath Areas 0 SqFt

$2,200,000

Midland Realty Group, Inc.
00 N 200, Fortville, IN 46040

00 N 200, Fortville, IN 46040

Great location and convenient to the schools and town. Come see this great lot with a wonderful fishing pond on the property.

0 Beds 0 Bath Areas 0 SqFt

$846,225

RE/MAX Realty Group
Lot 5 N 700th, Greenfield, IN 46140

Lot 5 N 700th, Greenfield, IN 46140

Don't miss your great opportunity to build your dream home on 13.19 acres with wooded private lot. Close to highway and great neighborhood. 2 parcels are being sold ...

0 Beds 0 Bath Areas 0 SqFt

$650,000

CENTURY 21 Scheetz
7144 N Hart Street, Cumberland, IN 46229

7144 N Hart Street, Cumberland, IN 46229

Olthof Homes presents The Preston. This home is appointed with 3,352 square feet of living space, find a foyer that merges with a flex room & a welcoming open area. ...

5 Beds 3 Bath Areas 3352 SqFt

$438,104

F.C. Tucker Company
7139 Hart Street, Cumberland, IN 46229

7139 Hart Street, Cumberland, IN 46229

Olthof Homes presents the Linden. Open the front door to 2,511 sf of living space. The welcoming foyer, showcases a flex room for hobbies, or a home office or music ...

4 Beds 3 Bath Areas 2511 SqFt

$431,079

F.C. Tucker Company
7096 W Payne Circle, Cumberland, IN 46229

7096 W Payne Circle, Cumberland, IN 46229

Olthof Homes presents the Keystone. Open the front door to 2,722 sf of well designed space. The spacious foyer showcases a flex room for hobbies, home office or dini...

4 Beds 3 Bath Areas 2722 SqFt

$428,059

F.C. Tucker Company
7103 E Hart Street, Cumberland, IN 46229

7103 E Hart Street, Cumberland, IN 46229

Olthof Homes presents our grand Sonoma plan with 2488 sqft and a 3-car garage. This open concept plan showcases our luxurious kit with 42” cabinets, quartz counter...

4 Beds 3 Bath Areas 2444 SqFt

$418,666

F.C. Tucker Company
5514 E Michigan Street, Indianapolis, IN 46219

5514 E Michigan Street, Indianapolis, IN 46219

Rare Opportunity to own this Gorgeous Historic Irvington Residence! Home of Irvington artist/designer Wayne Kimmell. 2003 Benton House Home Tour. Elegant details thr...

3 Beds 3 Bath Areas 2274 SqFt

$395,000

Centurion R.E.S., LLC
11803 W Adair Place, Indianapolis, IN 46229

11803 W Adair Place, Indianapolis, IN 46229

New built 4 bedroom, 2 full bath in great Warren Township location. Home features, Custom Amish built cabinets in kitchen and bathroom, granite counter tops, Stainle...

4 Beds 2 Bath Areas 1983 SqFt

$380,736

United Real Estate Indpls
609 S Sonoma Lane, Greenfield, IN 46140

609 S Sonoma Lane, Greenfield, IN 46140

3 bedroom 2 bathroom stunner in Converse! Fully equipped eat-in kitchen includes sleek counters and stainless appliances. Discover a bright interior with neutral woo...

4 Beds 3 Bath Areas 3087 SqFt

$365,000

Opendoor Brokerage LLC
850 S Summerhaven Court, New Palestine, IN 46163

850 S Summerhaven Court, New Palestine, IN 46163

Welcome Home!!! This beautiful home features 5 bedrooms 3 full bathrooms and over 2,500sqft. Main floor bedroom and full bath. Open floor plan with upstairs loft. Sp...

5 Beds 3 Bath Areas 2564 SqFt

$359,999

MayRealtors, LLC
359 S Ritter Avenue, Indianapolis, IN 46219

359 S Ritter Avenue, Indianapolis, IN 46219

Unique Victorian-Gothic house divided into 3 apartments. Possibilities abound here!! Home is currently used as a large family home with in-law quarters. Originally b...

0 Beds 0 Bath Areas 0 SqFt

$350,000

Carpenter, REALTORS®
359 S Ritter Avenue, Indianapolis, IN 46219

359 S Ritter Avenue, Indianapolis, IN 46219

Step back in time to this Victorian-Gothic home in beautiful Historic Irvington.Possibilities abound here!Historical records indicate the home was built in 1876 by...

4 Beds 4 Bath Areas 5388 SqFt

$350,000

Carpenter, REALTORS®
921 E Main Street, Greenfield, IN 46140

921 E Main Street, Greenfield, IN 46140

Pride of ownership shines throughout! Fresh paint, new carpet are just the tip of the iceberg. Other updates: custom tile flooring, granite counters & cabinets give ...

3 Beds 3 Bath Areas 2511 SqFt

$339,900

RE/MAX Realty Group
776 N Van Buren Street, Greenfield, IN 46140

776 N Van Buren Street, Greenfield, IN 46140

New Construction by D.R. Horton! Welcome to the Chatham in Meridian North. This home provides 4 bedrooms and 2 baths in a single-level, open living space. The main l...

4 Beds 2 Bath Areas 1771 SqFt

$336,525

HMS Real Estate, LLC
932 S Havens Drive, New Palestine, IN 46163

932 S Havens Drive, New Palestine, IN 46163

IMMEDIATE OCCUPANCY. This Havens beauty is so clean, loved and move-in ready. Comfortable circular floor plan. Master suite features Cathedral ceiling, walk-in close...

3 Beds 3 Bath Areas 2157 SqFt

$334,900

Ala Carte Realty
229 W North Street, Greenfield, IN 46140

229 W North Street, Greenfield, IN 46140

Spacious home in booming Greenfield! This turn of the last century home boasts over 2200 sq ft of living space and was remodeled approximately 4 years ago. Updates ...

4 Beds 4 Bath Areas 2499 SqFt

$314,999

Hanza Realty, LLC
861 N Swope Street, Greenfield, IN 46140

861 N Swope Street, Greenfield, IN 46140

Over 2 acres in the heart of Greenfield! So much potential in this growing area with city street access, woods, and more. Zoning: Vacant Platted Land.

0 Beds 0 Bath Areas 0 SqFt

$304,977

Level Up Real Estate Group
1042 E Hopkins Road, Indianapolis, IN 46229

1042 E Hopkins Road, Indianapolis, IN 46229

Outstanding 4 Bedroom/3Bath, 2-story home in popular Harvest Glen! Beautiful wooded/corner lot within Mt Vernon School District features: 2 Master Bedrooms w/ full b...

4 Beds 3 Bath Areas 2093 SqFt

$289,900

CENTURY 21 Scheetz
472 S Old Glory Drive, Greenfield, IN 46140

472 S Old Glory Drive, Greenfield, IN 46140

Property is in need of repair, but there is tons of potential. This would make a great investment property! One of the largest floorplans in the neighborhood.

5 Beds 3 Bath Areas 1922 SqFt

$279,900

Compass Indiana, LLC
120 N Pennsylvania Street, Greenfield, IN 46140

120 N Pennsylvania Street, Greenfield, IN 46140

4-unit investment property has everything that you could need as it is close to everything in the Greenfield square.

0 Beds 0 Bath Areas 0 SqFt

$275,000

The Stewart Home Group
7041 S Lillian Place, Cumberland, IN 46229

7041 S Lillian Place, Cumberland, IN 46229

Olthof Homes presents the Laine Paired Villa. Wonderful maintenance free living. Never have to worry about the yardwork or snow removal again. We do it for you. This...

2 Beds 2 Bath Areas 1515 SqFt

$274,433

F.C. Tucker Company
6030 E 9th Street, Indianapolis, IN 46219

6030 E 9th Street, Indianapolis, IN 46219

1930'S brick Tudor on a wonderful lot that faces Pleasant Run Golf Course! Enjoy the character of the vaulted cathedral ceilings as you enter the home, built in chin...

3 Beds 2 Bath Areas 2655 SqFt

$269,000

F.C. Tucker Company
121 W Tinker Trail, Greenfield, IN 46140

121 W Tinker Trail, Greenfield, IN 46140

This updated 3 bedroom, 2.5 bath home in Greenfield is a must see! Updates include LVP flooring throughout majority of the home, updated light fixtures, new water he...

3 Beds 3 Bath Areas 1802 SqFt

$255,000

Indianapolis Homes Realty Grou
441 E Woodstream Dr., Greenfield, IN 46140

441 E Woodstream Dr., Greenfield, IN 46140

Well maintained, almost completely updated home on a beautiful lot that backs up to woods and a creek! Hard surface flooring throughout ENTIRE home! New within the...

3 Beds 3 Bath Areas 1580 SqFt

$250,000

Level Up Real Estate Group
N~2Fa E Us 40, Greenfield, IN 46140

N~2Fa E Us 40, Greenfield, IN 46140

14 +/- acres located outside of desirable Greenfield, IN. Excellent addition to your already tillable acreage or build your dream home on. Property has roughly 495' ...

0 Beds 0 Bath Areas 0 SqFt

$250,000

Ferris Property Group
906 W North Street, Greenfield, IN 46140

906 W North Street, Greenfield, IN 46140

Check out this charming farmhouse in the heart of downtown Greenfield! Just one block north of Main Street, this 3 bedroom & 3.5 bath home is walking-distance to res...

3 Beds 4 Bath Areas 2296 SqFt

$249,900

CENTURY 21 Scheetz
905 Burbank Road, Indianapolis, IN 46219

905 Burbank Road, Indianapolis, IN 46219

If you are an Outdoor Enthusiast, this property is for you! There is It a Pond with Waterfall, 2 Sheds both with electricity, above ground pool for hot days, Screen...

3 Beds 2 Bath Areas 1829 SqFt

$249,900

eXp Realty, LLC
2429 W Us Highway 40, Greenfield, IN 46140

2429 W Us Highway 40, Greenfield, IN 46140

Fall in love with this country charmer with acreage! Right when you step into this beauty you can begin to feel the updates throughout the home which includes floor...

3 Beds 1 Bath Areas 2214 SqFt

$249,000

F.C. Tucker Company
25 N Sheridan Avenue, Indianapolis, IN 46219

25 N Sheridan Avenue, Indianapolis, IN 46219

Freshly updated Irvington home features the original details you are looking for, along with the extra space that you need. Brand new kitchen features Silestone quar...

3 Beds 2 Bath Areas 2880 SqFt

$240,000

Ala Carte Realty
1853 S Roosevelt Drive, Greenfield, IN 46140

1853 S Roosevelt Drive, Greenfield, IN 46140

Well established neighborhood. One owner home. Sellers had the home built with Melody Home Builders. Nice sunroom on the back of the home for year round use. All app...

3 Beds 2 Bath Areas 1370 SqFt

$239,999

Home Loop Realty, LLC
453 Ashby Drive, Greenfield, IN 46140

453 Ashby Drive, Greenfield, IN 46140

You will love this ranch style home in a quiet Greenfield neighborhood, This home features 3 bedrooms, 2 full baths, and a large flex room with open concept. Gather...

3 Beds 2 Bath Areas 1338 SqFt

$239,000

RE/MAX Advanced Realty
647 E Center Street, Greenfield, IN 46140

647 E Center Street, Greenfield, IN 46140

Bring your furniture and you can walk right in and make this spotless house yours! Some updates include roof 2 years new, vinyl plank flooring throughout the entire ...

3 Beds 2 Bath Areas 1496 SqFt

$234,000

McGauley Realty, Inc.
159 N Welker Drive, Greenfield, IN 46140

159 N Welker Drive, Greenfield, IN 46140

1950s Ranch house with 3 beds and 2 full bathrooms on two lots in Southern Hancock County School District is ready for you to make it your home! This home comes comp...

3 Beds 2 Bath Areas 1463 SqFt

$230,000

The Cooper Real Estate Group
2832 W Walnut Drive, Greenfield, IN 46140

2832 W Walnut Drive, Greenfield, IN 46140

Check out this unique 3 bed, 2 bath house on a half acre lot in an established, quiet neighborhood! Fully fenced back yard, 2 car garage, cozy wood burning fireplac...

3 Beds 2 Bath Areas 1426 SqFt

$230,000

Level Up Real Estate Group
115 S Boehning Street, Indianapolis, IN 46219

115 S Boehning Street, Indianapolis, IN 46219

Checkout this sprawling ranch on an almost an acre lot! NEW AC, NEW Paint, NEW flooring, NEW carpet...Lots of spacy in this bright cheery floor plan with new tile fl...

3 Beds 2 Bath Areas 1318 SqFt

$225,000

Vylla Home
138 N 350 West, Greenfield, IN 46140

138 N 350 West, Greenfield, IN 46140

Fabulous multiple story home with over 3700 sq ft with 4 bedrooms, 2.5 baths, on over 1 acre of gorgeous wooded and private setting. Home is being sold As-Is. Kitche...

4 Beds 3 Bath Areas 3780 SqFt

$225,000

RE/MAX Realty Group
316 E North Street, Greenfield, IN 46140

316 E North Street, Greenfield, IN 46140

Classical Victorian in one of Greenfield's finest areas. This 5 bedroom home has 2 full baths with updates that include vinyl thermopane windows, new 200AMP electric...

5 Beds 2 Bath Areas 3575 SqFt

$219,900

RE/MAX Realty Group
503 W Sixth Street, Greenfield, IN 46140

503 W Sixth Street, Greenfield, IN 46140

This four bedroom two full bath home located in the Greenfield Central School district features a fully fenced rear yard, three car detached garage, and includes kit...

4 Beds 2 Bath Areas 1728 SqFt

$216,500

RE/MAX Realty Group
737 N Spring Street, Greenfield, IN 46140

737 N Spring Street, Greenfield, IN 46140

2 units located on one lot. Rental #1 is 2 bedrm, 1 bath, with detached garage, LEASED $975.00 month-tenant pays all utilities. Updated roof, furnace/AC, laminate fl...

0 Beds 0 Bath Areas 0 SqFt

$214,000

RE/MAX Realty Group
737 N Spring Street, Greenfield, IN 46140

737 N Spring Street, Greenfield, IN 46140

Great Investor opportunity includes 2 bedroom 1 bath ranch with detached garage, plus 1 bedroom rental. 468 sq ft Detached in-laws quarters with so many uses. Updat...

2 Beds 1 Bath Areas 1372 SqFt

$214,000

RE/MAX Realty Group
1015 W North Street, Greenfield, IN 46140

1015 W North Street, Greenfield, IN 46140

Welcome home to 1015 W. North St. it has 3-4 bedrooms and 2 full bathrooms. Features include an updated kitchen with appliances, open concept kitchen/living room, up...

3 Beds 2 Bath Areas 1594 SqFt

$205,000

Hoosier Dream Homes Real Estate LLC
392 W Ashby Drive, Greenfield, IN 46140

392 W Ashby Drive, Greenfield, IN 46140

Wonderful family home w/new 18x14 wood deck overlooking fenced back yard. This 3 bedroom, 2.5 bath home is clean and neat w/updates. Large great room w/ceramic tile ...

3 Beds 3 Bath Areas 1344 SqFt

$199,000

RE/MAX Realty Group
19 N Ritter Avenue, Indianapolis, IN 46219

19 N Ritter Avenue, Indianapolis, IN 46219

This very large home that is in the desirable Irvington historic district. It's been family owned for over 70 years. It needs work but can become a great home that h...

5 Beds 4 Bath Areas 2818 SqFt

$199,000

David Hunter
909 N Waring Drive, Indianapolis, IN 46229

909 N Waring Drive, Indianapolis, IN 46229

This attractive Tri-level home is in the Warren School District has been freshly painted with a new hood microwave oven and stove and a new dishwasher. Nice back yar...

3 Beds 2 Bath Areas 1404 SqFt

$189,900

Offerpad Brokerage, LLC
326 S Catherwood Avenue, Indianapolis, IN 46219

326 S Catherwood Avenue, Indianapolis, IN 46219

Great move-in ready home very convenient to all Irvington has to offer!! Home has been remodeled with a new roof, fresh paint, new flooring, remodeled kitchen and ba...

2 Beds 1 Bath Areas 1700 SqFt

$169,999

RE/MAX Advanced Realty
401 N Swope Street, Greenfield, IN 46140

401 N Swope Street, Greenfield, IN 46140

Great family home in Greenfield. Fenced in back yard and covered front porch. 2 rooms could be used as bedrooms but do not meet the requirements to call a bedroom. ...

2 Beds 2 Bath Areas 1524 SqFt

$160,000

RE/MAX Realty Group
303 E Douglas Street, Greenfield, IN 46140

303 E Douglas Street, Greenfield, IN 46140

**INVESTORS SPECIAL** - This large 2,561sf home sits on a corner lot and was previously a duplex. Home still has separate utilities. This would make a great investme...

0 Beds 0 Bath Areas 2561 SqFt

$150,000

Steve Lew Real Estate Group, LLC
115 N Gibson Avenue, Indianapolis, IN 46219

115 N Gibson Avenue, Indianapolis, IN 46219

Affordable 3 bedroom home plus basement sitting on 1/2 acre just 3 minutes from 465 and shops/restaurants. New roof and many upgrades have just been completed such ...

3 Beds 1 Bath Areas 2260 SqFt

$149,900

RE/MAX Advanced Realty
232 E Main Street, Greenfield, IN 46140

232 E Main Street, Greenfield, IN 46140

Two story current was used as a double but could be converted back to a beautiful single residence. There is a third level that could be another BR or great storage ...

0 Beds 0 Bath Areas 0 SqFt

$145,000

Berkshire Hathaway Home

Return to "Homes for Sale Near Central Indiana Trails"

The Pennsy Trail winds its way through the southern sector of downtown Greenfield into the lovely wooded areas to the east of town. It therefore lies within easy walking distance to all the downtown Greenfield restaurants, shops and services. At one point, the trail crosses James Whitcomb Riley's "old swimmin' hole" at Brandywine Creek.

Picture of the Pensy Trail at Pennyslvania Street in Greenfield, Indiana
Picture of the Pennsy Trail at Pennsylvania Street in Greenfield, Indiana.

Already in use, though new, the trail is the site of the Pennsy Trail Art Fair and several organized community runs. It's a smooth, asphalt-paved surface meant to be used for activities such as strolling, running, rollerblading and biking. When it comes to things to do in Greenfield, health- and beauty-conscious locals often choose the Pennsy Trail as a prime location.

Trailheads in Greenfield are stationed at the parking area on downtown Greenfield's Center Street and at Morristown Pike. The Pennsy Trail runs parallel to the Old National Road. In the works is another tributary consisting of one mile along the beautiful Brandywine Creek. The length of the primary corridor of Pennsy Trail is about five and one-half miles, three of which meander through the city of Greenfield.

The Pennsy Trail is, in fact, part of a grand plan, spearheaded by the "Rails-to-Trails" National Road Heritage Trail project, to lay 150 miles of practical and beautiful trails, eventually connecting several states.