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

0 N State Road 9, Greenfield, IN 46140

0 N State Road 9, Greenfield, IN 46140

A total of 3 parcels all bordering each other. 161 + acres are in Center Township and sits on Steele Ford Road, 80 acres are in Brandywine Township and sit on State...

0 Beds 0 Bath Areas 0 SqFt

$3,192,000

Landtree, REALTORS®
97 N 150, Greenfield, IN 46140

97 N 150, Greenfield, IN 46140

Multiple use opportunity for business owner and/or hobbyist to transform this space with multiple outbuildings into whatever they desire! With 5 outbuildings (all w...

3 Beds 3 Bath Areas 3122 SqFt

$899,000

Front Porch Real Estate, LLC
220 S Post Road, Indianapolis, IN 46219

220 S Post Road, Indianapolis, IN 46219

Robert Hamilton Estate 1835 Classical charm blends seamlessly with modern lifestyle in this fully updated 5 bedroom 2 bath 3400 sqft Victorian home on 2 acres of pr...

5 Beds 2 Bath Areas 3364 SqFt

$377,700

Paradigm Realty Solutions
865 N German Church Road, Indianapolis, IN 46229

865 N German Church Road, Indianapolis, IN 46229

This commercial property with a C3 zoning classification has excellent exposure to German Church Road and East 10th Street. The site has all utilities available to i...

0 Beds 0 Bath Areas 0 SqFt

$350,000

McLane Realty
7067 E Hart Street, Cumberland, IN 46229

7067 E Hart Street, Cumberland, IN 46229

Olthof Homes presents our Huntington, single family ranch model with 3 car garage. This home features open concept living at its best, and it includes a sunroom with...

3 Beds 2 Bath Areas 2047 SqFt

$323,094

F.C. Tucker Company
6909 E Washington Street, Indianapolis, IN 46219

6909 E Washington Street, Indianapolis, IN 46219

Amazing opportunity to purchase a oversized brick duplex that also has commercial zoning and has been family owned for decades! Beautiful built-ins, retro decor make...

0 Beds 0 Bath Areas 0 SqFt

$299,900

No Limit Real Estate, LLC
135 S Ritter Avenue, Indianapolis, IN 46219

135 S Ritter Avenue, Indianapolis, IN 46219

At the epicenter of Historic Irvington you will find this updated 3BD 2.5BA home! The main floor offers a more open feel w/ spacious living & dining area, tall ceili...

3 Beds 3 Bath Areas 2372 SqFt

$296,900

United Real Estate Indpls
3211 W Sharon Drive, Greenfield, IN 46140

3211 W Sharon Drive, Greenfield, IN 46140

Seller financed - No credit and bad credit accepted with a down payment. Move-in-ready brick ranch on a cul-de-sac. This home has new floors, new windows, paint, a...

3 Beds 2 Bath Areas 1428 SqFt

$295,000

Five-Star Realty Group, LLC
1984 E Fairmont Drive, Greenfield, IN 46140

1984 E Fairmont Drive, Greenfield, IN 46140

New Construction by D.R. Horton! Welcome to the Henley in Meridian North. This two-story home provides 5 large bedrooms and 3 full baths. The main level living area ...

5 Beds 3 Bath Areas 2600 SqFt

$291,480

HMS Real Estate, LLC
1956 N Fairmount Drive, Greenfield, IN 46140

1956 N Fairmount Drive, Greenfield, IN 46140

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

4 Beds 3 Bath Areas 2053 SqFt

$282,295

HMS Real Estate, LLC
1926 W Fairmount Drive, Greenfield, IN 46140

1926 W Fairmount Drive, Greenfield, IN 46140

New Construction by D.R. Horton! Welcome to the Chatham Meridian North at Springhurst. This home provides 4 bedrooms and 2.5 baths in a single-level, open living spa...

4 Beds 2 Bath Areas 1771 SqFt

$277,545

HMS Real Estate, LLC
5936 E Oak Avenue, Indianapolis, IN 46219

5936 E Oak Avenue, Indianapolis, IN 46219

Looking for that “move in” ready, updated home in one of the coolest parts of Irvington? Wind your way down Oak Ave to 5936, a classic two story originally built...

4 Beds 3 Bath Areas 2664 SqFt

$274,900

United Real Estate Indpls
602 N State Street, Greenfield, IN 46140

602 N State Street, Greenfield, IN 46140

An exceptional property offering a timeless turn-of-the-century feel. The residence has been renovated and restored to perfection showcasing both past and present fe...

3 Beds 1 Bath Areas 1506 SqFt

$264,900

Turnkey Realty of Indiana LLC
1962 N Fairmount Drive, Greenfield, IN 46140

1962 N Fairmount Drive, Greenfield, IN 46140

New Construction by D.R. Horton! Welcome to the Harmony in Meridian North. This home design provides 3 bedrooms and 2 full baths in a single-level, open living space...

3 Beds 2 Bath Areas 1498 SqFt

$259,845

HMS Real Estate, LLC
3800 W U S Highway 40 Highway, Greenfield, IN 46140

3800 W U S Highway 40 Highway, Greenfield, IN 46140

THERE ARE TWO TRACTS OF LAND TO THIS PROPERTY...IT HAS BEEN USED AS FARM GROUND IN THE PAST...LAND IS FLAT PRESENT ZONING IS CN (COMMERCIAL NEIGHBORHOOD).. GREAT LO...

0 Beds 0 Bath Areas 0 SqFt

$249,900

Janet L. Tucker REALTORS
128 S Arlington Avenue, Indianapolis, IN 46219

128 S Arlington Avenue, Indianapolis, IN 46219

Check out this beautiful 4 bedroom home located in the heart of Irvington. This home features a master suite and en-suite bath, large open concept kitchen with new c...

4 Beds 3 Bath Areas 2418 SqFt

$229,900

Trahan Realty Group
138 W Megan Way, Cumberland, IN 46229

138 W Megan Way, Cumberland, IN 46229

Olthof Homes presents our paired Villa Aria plan with 1465 sqft and a 2 car garage. This Villa home is a part of maintenance-free living with lawn care and snow remo...

2 Beds 2 Bath Areas 1465 SqFt

$229,354

F.C. Tucker Company
100 S Edmondson Avenue, Indianapolis, IN 46219

100 S Edmondson Avenue, Indianapolis, IN 46219

Tons of potential and possibilities on this 3.05 acre lot. Located just a 1/4 of a mile from the Shadeland/Washington St interchange, and 1 mile from the I-465/Wash...

0 Beds 0 Bath Areas 0 SqFt

$225,000

Weichert REALTORS® Cooper Grou
7001 S Lillian Place, Cumberland, IN 46229

7001 S Lillian Place, Cumberland, IN 46229

Our family-owned homebuilder is ready to have you in one of our new maintenance-free Laine home! This paired villa features 1615 square feet with 2 beds, 2 bath, den...

2 Beds 2 Bath Areas 1615 SqFt

$221,107

F.C. Tucker Company
11117 S Deer Valley Drive, Indianapolis, IN 46229

11117 S Deer Valley Drive, Indianapolis, IN 46229

This home has 4 bedrooms, 2 and 1/2 bathrooms and a spacious communal floorplan. It’s an excellent opportunity to move into the Warren area. Main Street Renewal do...

4 Beds 3 Bath Areas 2152 SqFt

$219,900

Main Street Renewal, LLC
11 S Kitley Avenue, Indianapolis, IN 46219

11 S Kitley Avenue, Indianapolis, IN 46219

Very nice completely updated home located in historic Irvington. New kitchen cabinets with granite tops, stainless steel appliances, new floor coverings and light fi...

3 Beds 3 Bath Areas 2281 SqFt

$216,000

Vintage Realty, Inc.
10465 E 10th Street, Indianapolis, IN 46229

10465 E 10th Street, Indianapolis, IN 46229

This parcel is labeled with the the address of the lot with the building of 10465 E Washington St but is actually a separate lot with 685 feet road frontage on Washi...

0 Beds 0 Bath Areas 0 SqFt

$200,000

Artisan, REALTORS®
11111 W Deer Valley Drive, Indianapolis, IN 46229

11111 W Deer Valley Drive, Indianapolis, IN 46229

Large home in a great community.

4 Beds 3 Bath Areas 2464 SqFt

$195,000

TBH Realty and Management, Inc
400 N 500e Road, Greenfield, IN 46140

400 N 500e Road, Greenfield, IN 46140

10 acres - approximate dimensions are 443 x 1009.76 ( 443 frontage on 500 E) Good drainage septic and well required,

0 Beds 0 Bath Areas 0 SqFt

$185,000

OK Baird, LLC
362 N Bazil Avenue, Indianapolis, IN 46219

362 N Bazil Avenue, Indianapolis, IN 46219

Nice property with 4 bedrooms and 2 bathrooms, fresh paint, new flooring with high quality water proof vinyl flooring and quality carpet.

4 Beds 2 Bath Areas 1792 SqFt

$180,000

Mentor Listing Realty Inc
6306 E Washington Street, Indianapolis, IN 46219

6306 E Washington Street, Indianapolis, IN 46219

Beautiful 2 story home in Historic Irvington! This home is in a great location close to restaurants and shops. It is accessible from Washington St as well as the all...

4 Beds 2 Bath Areas 2480 SqFt

$169,900

RE/MAX At The Crossing
55 N Shortridge Road, Indianapolis, IN 46219

55 N Shortridge Road, Indianapolis, IN 46219

This potential 4-bedroom 2-bath home has hardwood floors throughout the house, remodeled bathrooms, spacious living room, dining/breakfast kitchen area, detached 2 c...

2 Beds 2 Bath Areas 2224 SqFt

$160,000

F.C. Tucker Company
6037 N Dewey Avenue, Indianapolis, IN 46219

6037 N Dewey Avenue, Indianapolis, IN 46219

Wonderfully updated home with fenced yard, garage and enclosed front porch. The home offers original woodwork, arched wall, open floorplan kitchen, original hardwood...

2 Beds 2 Bath Areas 2048 SqFt

$152,500

Wynkoop Brokerage Firm, LLC
10435 E 10th Street, Indianapolis, IN 46229

10435 E 10th Street, Indianapolis, IN 46229

Open field with 193 feet of Road Frontage. Property is about half flood zone that is considered flood hazard AE which would require flood insurance or elevation cer...

0 Beds 0 Bath Areas 0 SqFt

$150,000

Artisan, REALTORS®
5821 E New York Street, Indianapolis, IN 46219

5821 E New York Street, Indianapolis, IN 46219

Quaint and cozy 2 bedroom home in historic Irvington on nice quiet street! Exterior updating needed and subject to the Irvington historic society. Interior just nee...

2 Beds 2 Bath Areas 1092 SqFt

$149,900

TKW
0 W Us Hwy 40, Brazil, IN 47834

0 W Us Hwy 40, Brazil, IN 47834

Great commercial opportunity on the "GROWING" west side of Brazil - Build to suit on 1.99 Acres in front of NEWLY constructed Villas of Holly Brook Assisted Living. ...

0 Beds 0 Bath Areas 0 SqFt

$149,250

Hoosier Homes and Land
7027 N Lakeshore Drive, Greenfield, IN 46140

7027 N Lakeshore Drive, Greenfield, IN 46140

Perfect setting for your new custom dream home! There are just a few lots remaining in the Sapphire Springs community. These are currently the best lots in Hancock c...

0 Beds 0 Bath Areas 0 SqFt

$145,000

Trueblood Real Estate
8431 E New York Street, Indianapolis, IN 46219

8431 E New York Street, Indianapolis, IN 46219

Incredible opportunity with this home! 3 bedrooms 1.5 baths, hardwood floors, fireplace and enclosed breezeway. Some updates already made, newer windows, HVAC and wa...

3 Beds 2 Bath Areas 1628 SqFt

$135,000

Elite Indy Realty Group
7831 E Vermont Street, Indianapolis, IN 46219

7831 E Vermont Street, Indianapolis, IN 46219

This cozy 3 bed, 2 bath sits in a quiet neighborhood on the city's east side. The large living room features a fireplace and access to an outdoor all-season room. A ...

3 Beds 2 Bath Areas 1276 SqFt

$134,900

The Modglin Group
327 N Noble Street, Greenfield, IN 46140

327 N Noble Street, Greenfield, IN 46140

Affordable turn of the century home located in the heart of Greenfield. Front and side porches. Walk-ability to downtown restaurants, churches, shops, schools, and...

3 Beds 1 Bath Areas 1681 SqFt

$124,900

Berkshire Hathaway Home
846 W North Street, Greenfield, IN 46140

846 W North Street, Greenfield, IN 46140

INVESTOR ALERT !!! Cute as can be duplex in great location of Greenfield. Each side provides a large one bedroom and bath with large kitchen and laundry hook ups/s...

0 Beds 0 Bath Areas 0 SqFt

$110,000

KORO Development, LLC
0 W Us Hwy 40, Brazil, IN 47834

0 W Us Hwy 40, Brazil, IN 47834

Great commercial opportunity on the "GROWING" west side of Brazil - Build to suit on 1.31 Acres in front of NEWLY constructed Villas of Holly Brook Assisted Living. ...

0 Beds 0 Bath Areas 0 SqFt

$98,250

Hoosier Homes and Land
7091 N Lakeshore Drive, Greenfield, IN 46140

7091 N Lakeshore Drive, Greenfield, IN 46140

Perfect setting for your new dream home. There are just a few lots remaining in the Sapphire Springs community. These are currently the best lots in Hancock county t...

0 Beds 0 Bath Areas 0 SqFt

$85,000

The Vearus Group
221 N Noble Street, Greenfield, IN 46140

221 N Noble Street, Greenfield, IN 46140

Perfect rental investment opportunity. Present tenant would like to remain. Covered front porch & enclosed back porch. New furnace in 2020. Laundry in back porch, so...

1 Beds 1 Bath Areas 1001 SqFt

$64,900

F.C. Tucker Company
515 E Grove Street, Greenfield, IN 46140

515 E Grove Street, Greenfield, IN 46140

Investment Opportunity! Property is in need of a Full Renovation. Home appears to be framed for 3 bedrooms and 2 full baths, but currently a 2 bedroom and 1 Full bat...

3 Beds 2 Bath Areas 1584 SqFt

$60,000

Red Oak Real Estate Group
0 Lot 1a Walnut Trce, Greenfield, IN 46140

0 Lot 1a Walnut Trce, Greenfield, IN 46140

Gorgeous condominium sub-division with variety of custom designed floor plans. There are extraordinary views of the woods year round. Beautiful Spring Flowers, Fal...

0 Beds 0 Bath Areas 0 SqFt

$35,000

RE/MAX Realty Group
106 S Webster Avenue, Indianapolis, IN 46219

106 S Webster Avenue, Indianapolis, IN 46219

Residential lot near Irvington

0 Beds 0 Bath Areas 0 SqFt

$19,000

CENTURY 21 Scheetz

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.