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

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

$799,000

Front Porch Real Estate, LLC
181 N 600 W Road, Greenfield, IN 46140

181 N 600 W Road, Greenfield, IN 46140

21.04 acres are located in Sugar Creek Township zoned CN commercial zoning. 3.0 Acres located in Buck Creek Township zoned R-1. Owner does not want to split the pro...

0 Beds 0 Bath Areas 0 SqFt

$720,000

Berkshire Hathaway Home
5250 W Us 40, Greenfield, IN 46140

5250 W Us 40, Greenfield, IN 46140

Present zoning is “Commercial Neighborhood” as defined by Hancock Co zoning ordinance. Cumberland water approx. 500’west on N side of US #40. County will requ...

0 Beds 0 Bath Areas 0 SqFt

$501,500

F.C. Tucker Company
2248 W Us Highway 40, Greenfield, IN 46140

2248 W Us Highway 40, Greenfield, IN 46140

BRAND....NEW....HOME. The former home on this site burned down. It has been replaced from the foundation up with a spectacular modern farmhouse! The attention to det...

3 Beds 3 Bath Areas 2162 SqFt

$397,500

Keller Williams Indy Metro NE
100 N Derbyshire Drive, Indianapolis, IN 46229

100 N Derbyshire Drive, Indianapolis, IN 46229

Welcome to 100 Derbyshire! You love this well appointed home with room for the whole family. Features include a 2 story foyer, granite countertops/newer appliances i...

4 Beds 3 Bath Areas 3965 SqFt

$395,000

Plat Collective
236 W North Street, Greenfield, IN 46140

236 W North Street, Greenfield, IN 46140

INVESTORS ALERT!!! Very unique opportunity. So many options with this one. Two separate investment properties on the same parcel. Front property is a duplex. Ma...

0 Beds 0 Bath Areas 0 SqFt

$395,000

KORO Development, LLC
5849 W Beechwood Avenue, Indianapolis, IN 46219

5849 W Beechwood Avenue, Indianapolis, IN 46219

Come check out this beautiful historic 1895 home in Irvington with updates throughout. 4 bedroom, 3 full bath with an amazing master suite in the finished large att...

4 Beds 3 Bath Areas 3340 SqFt

$364,900

Indy Home Shop LLC
1483 W Us Highway 40, Greenfield, IN 46140

1483 W Us Highway 40, Greenfield, IN 46140

GREAT INVESTMENT OPPORTUNITY FOR PUTTING BUSINESS OR RENOVATION OF HOME TO LIVE IN AND BUILD YOUR PERFECT VENUE TO RENT OUT WHILE LIVING ON THE PROPERTY. THERE ARE T...

3 Beds 1 Bath Areas 1800 SqFt

$350,000

CENTURY 21 Scheetz
242 S Green Meadow Drive, Indianapolis, IN 46229

242 S Green Meadow Drive, Indianapolis, IN 46229

Gorgeous 5 bedroom, 3 full bathrooms, and 1 half bath on a premium lot (no rear neighbors). Enter immediately to the office/den. Kitchen has granite counter tops, wa...

5 Beds 4 Bath Areas 3616 SqFt

$325,000

Carpenter, REALTORS®
303 N Arlington Avenue, Indianapolis, IN 46219

303 N Arlington Avenue, Indianapolis, IN 46219

This charming Craftsman style home located in Irvington, has been completely remodeled. Huge front porch, front and back lawn has brand new sod! 2 large Bedrooms wi...

3 Beds 2 Bath Areas 2207 SqFt

$259,900

Carpenter, REALTORS®
325 W Main Street, Greenfield, IN 46140

325 W Main Street, Greenfield, IN 46140

Main Street large duplex is the perfect locale for business owner or investor to live and work here or rent out to commercial tenant downstairs and residential tenan...

6 Beds 6 Bath Areas 4758 SqFt

$250,000

The Vearus Group
0 W Us Hwy 40, New Palestine, IN 46163

0 W Us Hwy 40, New Palestine, IN 46163

Great Highway 40 Frontage! Land is level and ready to build on and is prime location for many commercial uses. No trees or high power lines to deal with. All city...

0 Beds 0 Bath Areas 0 SqFt

$250,000

Quality Real Estate Solutions
318 N Bolton Avenue, Indianapolis, IN 46219

318 N Bolton Avenue, Indianapolis, IN 46219

Historic Irvington charmer on beautiful, tree lined street; Charming screened in front porch gives a great first impression; Enter the living room through classic, g...

2 Beds 2 Bath Areas 2550 SqFt

$230,000

VKN Realty, LLC
2818 W Sycamore Drive, Greenfield, IN 46140

2818 W Sycamore Drive, Greenfield, IN 46140

SOUTHERN HANCOCK SCHOOLS! Almost 1/2 an acre of Hamilton Heights heaven in Hancock County with 3 bedrooms 1 1/2 baths. Large trees,, detached garage, and brick exter...

3 Beds 2 Bath Areas 2136 SqFt

$226,000

Ala Carte Realty
34 N 300, Greenfield, IN 46140

34 N 300, Greenfield, IN 46140

Private ranch style home in sought after Southern Hancock schools. Over half an acre of wooded lot close to Greenfield. Park like setting , attractive living room wi...

3 Beds 2 Bath Areas 1812 SqFt

$226,000

Ala Carte Realty
128 S Arlington Avenue, Indianapolis, IN 46219

128 S Arlington Avenue, Indianapolis, IN 46219

BEAUITFUL 4 bedroom home located in the middle of Irvington. Home was just fully remodeled featuring a master suite with an en-suite bath, a large kitchen concept, n...

4 Beds 3 Bath Areas 2418 SqFt

$210,000

Trahan Realty Group
416 N Mitchner Avenue, Indianapolis, IN 46219

416 N Mitchner Avenue, Indianapolis, IN 46219

INVESTORS, take a look at this cute, Irvington, 3 bedroom, 2 bathroom, brick ranch, with mature trees in front, large fenced in backyard, hardwoods and tile througho...

3 Beds 2 Bath Areas 2350 SqFt

$210,000

eXp Realty, LLC
32 N Grant Street, Greenfield, IN 46140

32 N Grant Street, Greenfield, IN 46140

Buy a little history!!! This well-maintained home that was built in 1885 has been converted to a duplex and has been a wonderful income property for many years, with...

0 Beds 0 Bath Areas 0 SqFt

$204,900

Berkshire Hathaway Home
2399 E Walnut West Street, Greenfield, IN 46140

2399 E Walnut West Street, Greenfield, IN 46140

Charming home in quiet neighborhood! Feel like you're living in the country with quick and easy access to Indy! Enjoy coffee on the covered back patio looking out at...

2 Beds 1 Bath Areas 2740 SqFt

$200,000

Carpenter, REALTORS®
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®
333 S Gibson Avenue, Indianapolis, IN 46219

333 S Gibson Avenue, Indianapolis, IN 46219

Diamond in the rough but so much potential. Solid structure, Home has some missing drywall which could be a plus for your own design to move walls or change layout. ...

3 Beds 2 Bath Areas 960 SqFt

$199,900

House to Home Realty Solutions
247 S Arlington Avenue, Indianapolis, IN 46219

247 S Arlington Avenue, Indianapolis, IN 46219

A Must See beautiful bungalow in Historic Irvington with 3 bedrooms, 1.5 baths and great outdoor space. The front porch greets you as you enter this updated charmer ...

3 Beds 2 Bath Areas 2396 SqFt

$169,900

Trueblood Real Estate
6048 E Washington Street, Indianapolis, IN 46219

6048 E Washington Street, Indianapolis, IN 46219

Investors wanted. Cash flowing 4 plex. 1 bed, 1 bath, 560 sqft x 4. All 4 units are rented. Current gross monthly rent $2,125. Tenants pay Electric, Owner Pays Ga...

0 Beds 0 Bath Areas 0 SqFt

$167,500

eXp Realty, LLC
1015 E Third Street, Greenfield, IN 46140

1015 E Third Street, Greenfield, IN 46140

Roomy 3 bedroom, 2 full bath home w/3 car detached garage, fenced yard, and extra storage barn. Open floor plan with dine in kitchen, includes all appliances, and la...

3 Beds 2 Bath Areas 1404 SqFt

$150,000

RE/MAX Realty Group
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®
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/Washi...

0 Beds 0 Bath Areas 0 SqFt

$149,900

Weichert REALTORS® Cooper Grou
752 N Post Road, Indianapolis, IN 46219

752 N Post Road, Indianapolis, IN 46219

Welcome to this 3 bedroom, 1.5 bath brick ranch home w/over 1500 sq. ft. of beautifully open living space!! Large front room, efficient furnace & A/C unit, free-stan...

3 Beds 2 Bath Areas 1500 SqFt

$149,000

Scott Estates
247 N Routiers Avenue, Indianapolis, IN 46219

247 N Routiers Avenue, Indianapolis, IN 46219

Full Brick home. Cute as can be. Nothing to do but move in and enjoy. You have a extra large detached garage with workshop awaiting your cars and projects. Entertai...

2 Beds 1 Bath Areas 932 SqFt

$137,900

Eaglecrest Realty Group, LLC
518 N State Street, Greenfield, IN 46140

518 N State Street, Greenfield, IN 46140

Lots of potential on a nice sized duplex in Greenfield! This duplex has two bedrooms and one bath in each unit with the possibility for more. Attic space is usable...

0 Beds 0 Bath Areas 0 SqFt

$128,900

Evermark Property Group, LLC
37 S Johnson, Indianapolis, IN 46219

37 S Johnson, Indianapolis, IN 46219

Beautiful remodeled townhome in quiet, cozy block of central Historic Irvington. Charming turn-of-the-century building is a short walk to restaurants, shops & servic...

2 Beds 1 Bath Areas 1448 SqFt

$126,000

Keller Williams Indy Metro NE
1009 E Third Street, Greenfield, IN 46140

1009 E Third Street, Greenfield, IN 46140

Adorable home on 2 lots. Large living room, master bedroom plus guest bedroom and bonus room. Updated bathroom, separate utility room, and oversized 2 car garage (52...

2 Beds 1 Bath Areas 872 SqFt

$120,000

RE/MAX Realty Group
508 S State Street, Greenfield, IN 46140

508 S State Street, Greenfield, IN 46140

Walking distance to downtown Greenfield! 2 bed, 1 bath with 2 car detached garage. Property has a fenced in backyard, open patio area. Furnace is approximately 4 yea...

2 Beds 1 Bath Areas 1040 SqFt

$118,000

RE/MAX Realty Group
5 E Tague Street, Greenfield, IN 46140

5 E Tague Street, Greenfield, IN 46140

Partially Renovated. The Exterior was Completed within the last Three Years; New Roof, Gutters, Siding and Several Windows. The inside is a Blank Canvas. Most of ...

3 Beds 3 Bath Areas 2151 SqFt

$118,000

Carpenter, REALTORS®
12004 E Welland Street, Indianapolis, IN 46229

12004 E Welland Street, Indianapolis, IN 46229

Lovely 3 Bed/2.5 Bath condo features Large Living Room with French Doors opening to the Fenced Backyard, Wooden Deck and Storage Shed. Beautiful Vinyl Wood Flooring ...

3 Beds 3 Bath Areas 2207 SqFt

$108,000

Honor Realty LLC
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
143 S Arlington Avenue, Indianapolis, IN 46219

143 S Arlington Avenue, Indianapolis, IN 46219

Fantastic lot in beautiful Irvington community! Ready for you to build on! Already has a concrete pad for parking and a mulberry tree.

0 Beds 0 Bath Areas 0 SqFt

$12,500

Gallery of Homes Real Estate

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.