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.
897 Hugo Street, Indianapolis, IN 46229

897 Hugo Street, Indianapolis, IN 46229

Newly remodeled rental portfolio property, new flooring, paint and appliances. Tenants right apply

3 Beds 1 Bath Areas 1104 SqFt

$1,955,000

REI Premier Realty
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
251 N 300 W, Greenfield, IN 46140

251 N 300 W, Greenfield, IN 46140

Step inside to a complete transformation! Modern & updated, this 3500 sq ft ranch on 10.43 acres has 4 bedrooms, 4 full baths & 1 half bath, & 2 basements! A recent ...

4 Beds 5 Bath Areas 5240 SqFt

$829,900

Home Bound Real Estate LLC
365 Johnson Drive, Greenfield, IN 46140

365 Johnson Drive, Greenfield, IN 46140

Here's your opportunity to own 7.52 acres in a country setting within the city of Greenfield, just minutes away from shopping and restaurants. This one-of-a-kind spa...

3 Beds 4 Bath Areas 3176 SqFt

$689,900

Compass Indiana, LLC
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
404 N State Street, Greenfield, IN 46140

404 N State Street, Greenfield, IN 46140

Unique opportunity for home/business combinations. This Victorian home has excellent exposure on busy State Road 9 on the edge of downtown Greenfield. Many parking p...

4 Beds 2 Bath Areas 2692 SqFt

$475,000

McGauley Realty, Inc.
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

$444,715

Keller Williams Indpls Metro N
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

$430,845

F.C. Tucker Company
156 Lynnette Way, Cumberland, IN 46229

156 Lynnette Way, Cumberland, IN 46229

Olthof Homes presents the Keystone. Open the front door to 2722 sq ft of open concept beauty. Covered porch leads to open & airy floorplan. Kitchen w/quartz counters...

4 Beds 3 Bath Areas 2772 SqFt

$429,840

Keller Williams Indpls Metro N
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

$422,330

F.C. Tucker Company
852 S Raylee Garden Drive, New Palestine, IN 46163

852 S Raylee Garden Drive, New Palestine, IN 46163

This spacious home sits on .35-acre, with a wonderful view. This home features 4 bedrooms 2.5 baths, 3rd car garage 10'x 37', full fenced in back yard with a 13 x 10...

4 Beds 3 Bath Areas 3774 SqFt

$419,900

RE/MAX Real Estate Solutions
7128 Hart Street, Indianapolis, IN 46229

7128 Hart Street, Indianapolis, IN 46229

This beautiful Sonoma showcases our grand two-story great room and a bright sunroom. This home exudes luxury. Light infiltrates through our argon filled low E glass ...

4 Beds 3 Bath Areas 2588 SqFt

$410,072

F.C. Tucker Company
162 Lynnette Way, Cumberland, IN 46229

162 Lynnette Way, Cumberland, IN 46229

Olthof Homes presents the Linden. Open the front door to 2,501 sq. ft. of living space. The welcoming foyer showcases a flex room for hobbies, a home office or music...

4 Beds 3 Bath Areas 2512 SqFt

$409,740

Trueblood Real Estate
7103 Hart Street, Cumberland, IN 46229

7103 Hart Street, Cumberland, IN 46229

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

4 Beds 3 Bath Areas 2444 SqFt

$395,544

F.C. Tucker Company
180 Lynnette Way, Cumberland, IN 46229

180 Lynnette Way, Cumberland, IN 46229

Olthof Homes presents the Hudson. This open concept ranch combines 2043 square feet with one level living, and the result is a smart floor plan that is sure to pleas...

3 Beds 2 Bath Areas 2047 SqFt

$382,131

F.C. Tucker Company
733 W North Street, Greenfield, IN 46140

733 W North Street, Greenfield, IN 46140

A Greenfield original. This home was built in 1910 and has been past down for 3 generations ( 112 years ). In May of this year we began a complete restoration of the...

3 Beds 2 Bath Areas 2556 SqFt

$349,900

Welch & Wilson Real Estate, LL
1557 Leisure Way, Greenfield, IN 46140

1557 Leisure Way, Greenfield, IN 46140

Never lived in as owner discovered health issues just after starting construction and never moved in. Taxes reflect no exemption. Approx 8 yrs remaining on home warr...

2 Beds 2 Bath Areas 1762 SqFt

$339,900

F.C. Tucker Company
6947 W 100, New Palestine, IN 46163

6947 W 100, New Palestine, IN 46163

Country home w/many updated features including white kitchen w/new laminate flooring, countertops, appliances & sliding patio door to fenced back yard & deck/patio. ...

4 Beds 3 Bath Areas 2366 SqFt

$330,000

RE/MAX Realty Group
11803 Adair Place, Indianapolis, IN 46229

11803 Adair Place, Indianapolis, IN 46229

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

4 Beds 2 Bath Areas 1983 SqFt

$329,000

United Real Estate Indpls
510 E North Street, Greenfield, IN 46140

510 E North Street, Greenfield, IN 46140

Gorgeous Victorian style home completely renovated & restored while maintaining the original charm & character. Sip on coffee on the covered front porch area & enjoy...

3 Beds 3 Bath Areas 2263 SqFt

$290,000

eXp Realty, LLC
7091 Lillian Place, Cumberland, IN 46229

7091 Lillian Place, Cumberland, IN 46229

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

2 Beds 2 Bath Areas 1632 SqFt

$281,117

F.C. Tucker Company
7131 Lillian Place, Cumberland, IN 46229

7131 Lillian Place, Cumberland, IN 46229

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

3 Beds 2 Bath Areas 1632 SqFt

$280,708

F.C. Tucker Company
5170 E Us Highway 40, Greenfield, IN 46140

5170 E Us Highway 40, Greenfield, IN 46140

MUST SEE Unique home with endless potential in Eastern Hancock School district. Bedford stone ranch, 3 bedroom, 1 and 1/2 baths with additional 1/2 bath in the gara...

3 Beds 2 Bath Areas 3472 SqFt

$280,000

Carpenter, REALTORS®
117 N Eastern Village Drive, Greenfield, IN 46140

117 N Eastern Village Drive, Greenfield, IN 46140

RARE OPPORTUNITY to own a home in Eastern Village & Eastern Hancock Schools!! This solid 3 bedroom, 3 bathroom home on a half acre lot with 2 car garage features a l...

3 Beds 3 Bath Areas 2444 SqFt

$280,000

Real Broker, LLC
444 Sedgewick Drive, Greenfield, IN 46140

444 Sedgewick Drive, Greenfield, IN 46140

This is an incredible home! Open concept with tons of space, large closets, on a cul-de-sac. 4 bedrooms with an office, Greenfield schools, partial privacy fence, th...

4 Beds 3 Bath Areas 2852 SqFt

$280,000

RE/MAX Realty Group
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

$279,900

eXp Realty, LLC
505 Runnymede Court, Greenfield, IN 46140

505 Runnymede Court, Greenfield, IN 46140

If you are looking for space this home is for you. The first floor boasts an open kitchen, living room, breakfast room, and separate dining room. 4 large bedrooms an...

4 Beds 3 Bath Areas 2338 SqFt

$279,500

United Real Estate Indpls
11771 Adair Place, Indianapolis, IN 46229

11771 Adair Place, Indianapolis, IN 46229

Wow! This is truly an amazing opportunity to own this brand new brick ranch home, built by Coronado Homes. This home boast on trend expresso durable fiber cement sid...

3 Beds 2 Bath Areas 1604 SqFt

$279,000

Keller Williams Indy Metro W
11765 Adair Place, Indianapolis, IN 46229

11765 Adair Place, Indianapolis, IN 46229

New built Stunning 3 bedroom, 2 bath Ranch home offers Amish built cabinets, Stainless appliances, granite countertops w/breakfast bar in kitchen and large area for ...

3 Beds 2 Bath Areas 1670 SqFt

$279,000

United Real Estate Indpls
230 Walnut Street, Greenfield, IN 46140

230 Walnut Street, Greenfield, IN 46140

This beautiful home in the heart of Greenfield retains much of its original charm! Original hardwood floors, crown molding, wrap around porch, quaint back yard that ...

3 Beds 2 Bath Areas 2306 SqFt

$259,900

Offerpad Brokerage, LLC
2746 Winding Creek Lane, Greenfield, IN 46140

2746 Winding Creek Lane, Greenfield, IN 46140

Move-in ready & newly updated 3 bedroom, 2.5 bath + 2-C garage home in Sawmill! Great floor plan offers lots of space. Living room boasts high ceilings, fresh paint ...

3 Beds 3 Bath Areas 1896 SqFt

$259,900

Fathom Realty
153 Woodstream Court, Greenfield, IN 46140

153 Woodstream Court, Greenfield, IN 46140

Bright and sunny with no rear neighbors! This 3-bed/2.5-bath open floor plan at the end of a cul-de-sac boasts a new roof, new gutters, and a new 2-stage HVAC ( all ...

3 Beds 3 Bath Areas 1756 SqFt

$259,000

Keller Williams Indy Metro S
2734 Winding Creek Lane, Greenfield, IN 46140

2734 Winding Creek Lane, Greenfield, IN 46140

Welcome home to this charming ranch in the desirable Sawmill neighborhood which features a playground and swimming pool! Move right into this 3 bedroom, 2 bath home ...

3 Beds 2 Bath Areas 1399 SqFt

$234,900

Goat Real Estate, LLC
202 N State Street, Greenfield, IN 46140

202 N State Street, Greenfield, IN 46140

Commercial or work from home potential in the heart of Greenfield. This Victorian home has excellent exposure on busy State Road 9 on the edge of downtown, near the ...

4 Beds 2 Bath Areas 2409 SqFt

$224,000

Fathom Realty
902 Washington Cove Lane, Indianapolis, IN 46229

902 Washington Cove Lane, Indianapolis, IN 46229

Located in popular Hartman Farms, this 3 bedroom 2 1/2 bath home is loaded with features including brand new carpet throughout! Starting on the exterior, you'll find...

3 Beds 3 Bath Areas 1664 SqFt

$220,000

White Stag Realty, LLC
532 N State Street, Greenfield, IN 46140

532 N State Street, Greenfield, IN 46140

Charming 4 Bedroom 2 bath home in the heart of Greenfield. Close to downtown shopping, eating and schools. Great Room with built in storage, parks and walking paths ...

4 Beds 2 Bath Areas 2390 SqFt

$215,000

F.C. Tucker Company
1034 Winding Hart Drive, Indianapolis, IN 46229

1034 Winding Hart Drive, Indianapolis, IN 46229

This 3 bedroom, 2 bath ranch is ready for new owners! Fantastic private lot. Completely fenced in backyard with large deck. Plenty of green space plus a flower and ...

3 Beds 2 Bath Areas 1200 SqFt

$214,900

RE/MAX Edge
210 S State Street, Greenfield, IN 46140

210 S State Street, Greenfield, IN 46140

Great opportunity for office or retail near the courthouse, or as rental until needed. Floor plan is easily adaptable & current zoning of "Downtown District" allow m...

2 Beds 2 Bath Areas 1504 SqFt

$210,000

F.C. Tucker Company
6785 E Springer Avenue, Indianapolis, IN 46219

6785 E Springer Avenue, Indianapolis, IN 46219

Loads of upgrades. Huge kitchen with tons of cabinets, gas fireplace makes for cozy evening dinners. Tile floor and backsplash.Insulated crawl space. Built in bookca...

3 Beds 2 Bath Areas 1640 SqFt

$209,900

HomeXpert, Ray Stuck & Co.
3626 W Us Highway 40, Greenfield, IN 46140

3626 W Us Highway 40, Greenfield, IN 46140

LOCATION! LOCATION! LOCATION! This property has endless possibilities! Over 2 1/2 acres with commercial zoning on high traffic US 40. 2 bedroom/1bathroom home and a ...

2 Beds 1 Bath Areas 1339 SqFt

$199,000

Indy Crossroads Realty Group
927 Washington Cove Way, Indianapolis, IN 46229

927 Washington Cove Way, Indianapolis, IN 46229

 

3 Beds 2 Bath Areas 1200 SqFt

$199,000

True Property Management
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
516 Payton Avenue, Indianapolis, IN 46219

516 Payton Avenue, Indianapolis, IN 46219

Fantastic 4BDRM/2BA ranch in Warren Park that will make a great addition to your rental portfolio! Gas fuel with central air on a large lot. Pick this one up today? ...

4 Beds 2 Bath Areas 1476 SqFt

$180,000

Matlock Realty Group
12235 Harvest Glen Drive, Indianapolis, IN 46229

12235 Harvest Glen Drive, Indianapolis, IN 46229

Come add your finishing touches!! 3 bed 2 bath home in Mount Vernon School district. Open floor plan with spacious bedrooms. Home has vaulted ceiling and ample natur...

3 Beds 2 Bath Areas 1401 SqFt

$179,900

E-Rocks Real Estate
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

$170,000

Premier Homes Group
34 N Catherwood Avenue, Indianapolis, IN 46219

34 N Catherwood Avenue, Indianapolis, IN 46219

This property is part of a portfolio for sale that must be sold as one package. Please see agent remarks for all other properties in portfolioRental Rate -- $1100/m...

2 Beds 1 Bath Areas 1750 SqFt

$170,000

Matlock Realty Group
11108~2D11110 E Washington Street, Indianapolis, IN 46229

11108~2D11110 E Washington Street, Indianapolis, IN 46229

Duplex that is part of a package of properties to be sold as one portfolio. Please see agent remarks regarding all properties11108 --$900/month. Lease expires 12/1/...

0 Beds 0 Bath Areas 0 SqFt

$170,000

Matlock Realty Group
50 N Catherwood Avenue, Indianapolis, IN 46219

50 N Catherwood Avenue, Indianapolis, IN 46219

This property is part of a portfolio for sale that must be sold as one package. Please see agent remarks for all other properties in portfolioRental Rate -- $1024/m...

3 Beds 1 Bath Areas 1842 SqFt

$170,000

Matlock Realty Group
41 ~2D 43 N Catherwood Avenue, Indianapolis, IN 46219

41 ~2D 43 N Catherwood Avenue, Indianapolis, IN 46219

This property is part of a portfolio for sale that must be sold as one package. Please see agent remarks for all other properties in portfolioRental Rates -- 41 N. ...

0 Beds 0 Bath Areas 0 SqFt

$170,000

Matlock Realty Group

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.