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

174 Lynnette Way, Indianapolis, IN 46229

174 Lynnette Way, Indianapolis, IN 46229

Olthof Homes presents the Sedona. This home boasts 2682sf of living space. Private Owners Suite, deluxe owners bath and walk in closet. 4 bedrooms. The great room me...

4 Beds 3 Bath Areas 2722 SqFt

$449,381

F.C. Tucker Company
891 S Waterway Drive, New Palestine, IN 46163

891 S Waterway Drive, New Palestine, IN 46163

Brand new 5 beds & 3 bath home! Farmhouse style elevations welcomes you with a covered front & back porch. Once through the front door, you are greeted with an open ...

5 Beds 3 Bath Areas 3623 SqFt

$434,990

A G Wheeler Realty, LLC
7144 Payne Circle, Indianapolis, IN 46229

7144 Payne Circle, Indianapolis, IN 46229

This beautiful new arts and crafts two story home with full height cultured stone exterior features an open floor plan. The flex room, Great room, kitchen and mornin...

4 Beds 3 Bath Areas 2722 SqFt

$422,060

Keller Williams Indpls Metro N
232 Chadford Court, Indianapolis, IN 46229

232 Chadford Court, Indianapolis, IN 46229

Coronado Homes presents the "Bristol" Ranch home on a Basement! This 3-bedroom home with Master Suite and great room design. Located in Cumberland's Grassy Village,...

3 Beds 2 Bath Areas 2808 SqFt

$399,000

F.C. Tucker Company
234 Bardwell Court, Indianapolis, IN 46229

234 Bardwell Court, Indianapolis, IN 46229

Coronado home presents the Julianna floor plan. This Ranch home boast a full walk-out unfinished basement, which includes rough-ins for full bath and 4th bedroom, 2...

4 Beds 3 Bath Areas 2635 SqFt

$379,000

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

7096 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

$377,302

F.C. Tucker Company
1304 Byron Street, Greenfield, IN 46140

1304 Byron Street, Greenfield, IN 46140

New Construction by D.R. Horton! Welcome to the Holcombe in Meridian North. This two-story, open concept home provides 4 large bedrooms and 2.5 baths. The main level...

4 Beds 3 Bath Areas 2356 SqFt

$330,000

HMS Real Estate, LLC
11824 Adair Place, Indianapolis, IN 46229

11824 Adair Place, Indianapolis, IN 46229

Gorgeous new build. spacious corner lot. Kitchen has all white cabinetry with amazing granite and bar area. Quaint eat in kitchen with lovely windows to watch natur...

3 Beds 2 Bath Areas 1569 SqFt

$329,000

Manis Group M.S.WOODS
814 N Woodlark Drive, Indianapolis, IN 46229

814 N Woodlark Drive, Indianapolis, IN 46229

Immaculate 4 bed/ 2 bath property. Completely remodeled & updated. Features beautiful ceramic tile floors through living room, dining and kitchen. Bathrooms have bee...

4 Beds 2 Bath Areas 1902 SqFt

$249,900

eXp Realty, LLC
222 Douglas Street, Greenfield, IN 46140

222 Douglas Street, Greenfield, IN 46140

Investors Special! Great opportunity to reflip in a growing community. Large 2-story home in the heart of Greenfield, 2902 sqft, 5 bdrms, 2 full bathrooms, beautifu...

5 Beds 2 Bath Areas 3173 SqFt

$187,900

CENTURY 21 Scheetz
11629 Deanna Drive, Indianapolis, IN 46229

11629 Deanna Drive, Indianapolis, IN 46229

Really nice Cumberland location and the dead end street makes it so private! The large master bedroom features French doors and leads out to two woods decks! New vin...

3 Beds 1 Bath Areas 1255 SqFt

$165,000

Premier Homes Group
74 S Kitley Avenue, Indianapolis, IN 46219

74 S Kitley Avenue, Indianapolis, IN 46219

Good News!!! REDUCED! if you're looking for a home on a large lot -- this is it. Home features: LR, DR, KIT, 4 Brs, 2 Bas, Finished Bsmt, Encl front porch and 4 c...

4 Beds 2 Bath Areas 1752 SqFt

$159,900

Owens Realty
402 S Carroll Road, Indianapolis, IN 46229

402 S Carroll Road, Indianapolis, IN 46229

Undeveloped land south of Grassy Village. All utilities are available, this is a great opportunity to build your dream home or mini farm. Located within the Warr...

0 Beds 0 Bath Areas 0 SqFt

$159,900

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

25 N Arlington Avenue, Indianapolis, IN 46219

Charming duplex has much of it's original character. Main entrance has shared foyer with private access to each unit inside. The lower unit has large archways betw...

0 Beds 0 Bath Areas 0 SqFt

$139,500

Engel & Volkers
231 S Routiers Avenue, Indianapolis, IN 46219

231 S Routiers Avenue, Indianapolis, IN 46219

Back on Market because previous Buyer could not preform. Visit and Inspect property prior to making any offer. Sits on large lot. Sold AS-IS and needs total renovati...

3 Beds 1 Bath Areas 1316 SqFt

$130,000

Flat Fee Realty, LLC
902 Woodlark Drive, Indianapolis, IN 46229

902 Woodlark Drive, Indianapolis, IN 46229

Home is being sold as-is. It's in a demo state. Use caution when touring. Brokerage does not advertise on Craigslist and will never ask you to wire money or request ...

4 Beds 2 Bath Areas 1757 SqFt

$128,700

Main Street Renewal, LLC
0 Hill East Drive, Greenfield, IN 46140

0 Hill East Drive, Greenfield, IN 46140

2 lots totaling 1.21 acres that includes part lake ownership per lot lines. Great for building your dream home. Enjoy all a lake has to offer and the eagles in the a...

0 Beds 0 Bath Areas 0 SqFt

$80,000

Complete Real Estate Solutions
623 S State Street, Greenfield, IN 46140

623 S State Street, Greenfield, IN 46140

Amazing potential on this Victorian 5-Bedroom home in the heart of Downtown Greenfield. Potentially possibly for commercial use. Nearly 1 acre lot with partial fenci...

5 Beds 1 Bath Areas 2024 SqFt

$74,900

Keller Williams Indy Metro S

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.