Vintage homes for sale & real estate in Monroe County, IN

143 homes

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NEW 29 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Monroe County, IN:
Located at 3450 N Maple Grove Rd in Bloomington, Indiana, this 16.67 +/- acre property offers mature hardwood timber, Stout Creek, and potential building opportunities in a desirable area of Monroe County. Conveniently located near Indiana University, Griffy Lake Nature Preserve, Bloomington amenities, and I-69, the property combines privacy with accessibility. A paved driveway extending over 700 feet leads through the wooded landscape to an existing older home. The residence may require substantial renovation or removal, and no value has been assigned to the home. The property is being sold "As Is, " allowing buyers to determine the best use of the existing structure. Several rel

$374,900

2 beds1.5 baths1,780 sq ft

3450 N Maple Grove Rd, Bloomington, IN 47404

Existing utilities • Paved driveway • Custom home

FOR SALE BY OWNER

ABOUT THIS HOME
Vintage Home for sale in Monroe County, IN:
Mid-century opportunity with acreage in Bloomington! On a sprawling 1.4-acre parcel with a territorial view on Bloomington & rsquo; s highly desirable south side. This 1955-built classic offers the perfect blend of nostalgic character and unmatched property potential. Featuring 3 bedrooms, 1 bathroom, kitchen with beautiful original custom made cabinets, living room and 6 closets, wood flooring, open arched doorways in kitchen and living room and a full unfinished basement (1,050 sq. ft. on the main level plus an additional 1,050 sq. ft. below, delivering 2,100 total gross square feet of opportunity). Home retains its authentic, dated 1950s appeal and is ready for your personal modern u

$375,000

3 beds1 bath728 sq ft

4625 S Walnut Street Pike, Bloomington, IN 47401

Expansive lot • Territorial view • Open arched doorways

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Monroe County, IN:
Mid-century character, an all-limestone exterior, and almost 2400 sq ft to make it your own! This 3-bedroom, 1.5-bath ranch features a lovely stone fireplace in the living room, brand-new living room carpet, and real hardwood floors in the bedrooms. Several kitchen updates were made approximately 7 years ago. Downstairs, a second stone fireplace is an unexpected standout in the partially finished basement. Previously used for storage, hobbies, and recreational space, this level offers plenty of potential for your own plans. The oversized one-car garage provides generous room for parking, tools, and projects, while the nearly half acre, level yard offers usable outdoor space. Conveniently lo

$199,900

3 beds1.5 baths1,196 sq ft

100 S Kimble Dr, Bloomington, IN 47404

Kitchen updates • Usable outdoor space • Limestone exterior

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in Monroe County, IN:
Located just a few blocks from Bryan Park, this charming bungalow offers convenient access to IU, bus lines, and downtown Bloomington. Featuring 2 bedrooms, 1 bathroom, hardwood floors, a sunporch, an unfinished full basement, and a one-car garage, this home has plenty of potential. The furnace and air conditioning are only 3 years old! The spacious basement provides excellent space for projects, hobbies, or storage. Enjoy outdoor living in the partially fenced yard. Located in the Templeton, Jackson Creek, and Bloomington South school districts, this home is priced with its potential in mind and ready for a new owner to make it their own!

$220,000

2 beds1 bath740 sq ft

1208 S Fess Ave, Bloomington, IN 47401

Sunporch • Hardwood floors • 6,926 sq ft lot

$699,900

4 beds3 baths3,314 sq ft

1016 E Maxwell Ln, Bloomington, IN 47401

Hot tub • Brick fireplace • Updated kitchen

Property at 925 W Cedar Bluff Rd, Bloomington, IN 47403, 4 beds, 2 baths

$299,000

4 beds2 baths1,540 sq ft

925 W Cedar Bluff Rd, Bloomington, IN 47403

Property at 4062 W Broadway Ave, Bloomington, IN 47404, 3 beds, 1.5 baths

$254,900

3 beds1.5 baths2,592 sq ft

4062 W Broadway Ave, Bloomington, IN 47404

Property at 2615 S Rockport Rd, Bloomington, IN 47403, 2 beds, 1 bath

$214,000

2 beds1 bath826 sq ft

2615 S Rockport Rd, Bloomington, IN 47403

Property at 2912 S Walnut Street Pike, Bloomington, IN 47401, 3 beds, 1.5 baths

$225,000

3 beds1.5 baths1,118 sq ft

2912 S Walnut Street Pike, Bloomington, IN 47401

Property at 134 N Roosevelt St, Bloomington, IN 47408, 2 beds, 1 bath

$250,000

2 beds1 bath725 sq ft

134 N Roosevelt St, Bloomington, IN 47408

Property at 910 S Ransom Ln, Bloomington, IN 47403, 3 beds, 1 bath

$97,500

3 beds1 bath1,456 sq ft

910 S Ransom Ln, Bloomington, IN 47403

Property at 1175 W Bell Rd, Bloomington, IN 47404, 3 beds, 2 baths

$329,000

3 beds2 baths1,560 sq ft

1175 W Bell Rd, Bloomington, IN 47404

Property at 1106 S Madison St, Bloomington, IN 47403, 4 beds, 2 baths

$190,000

4 beds2 baths1,130 sq ft

1106 S Madison St, Bloomington, IN 47403

Property at 4414 N Old State Road 37, Bloomington, IN 47408, 3 beds, 2 baths

$299,000

3 beds2 baths1,955 sq ft

4414 N Old State Road 37, Bloomington, IN 47408

Property at 3625 Old Meyers Rd, Bloomington, IN 47408, 2 beds, 1 bath

$235,000

2 beds1 bath1,040 sq ft

3625 Old Meyers Rd, Bloomington, IN 47408

Property at 603 S Eagleson Ave, Bloomington, IN 47401, 2 beds, 2 baths

$550,000

2 beds2 baths1,924 sq ft

603 S Eagleson Ave, Bloomington, IN 47401

Property at 325 S Fairview St, Bloomington, IN 47403, 2 beds, 2 baths

$269,900

2 beds2 baths1,086 sq ft

325 S Fairview St, Bloomington, IN 47403

Property at 5050 N Union Valley Rd, Bloomington, IN 47404, 4 beds, 3 baths

$399,900

4 beds3 baths2,765 sq ft

5050 N Union Valley Rd, Bloomington, IN 47404

Property at 513 W Coolidge Dr, Bloomington, IN 47403, 2 beds, 1 bath

$195,000

2 beds1 bath824 sq ft

513 W Coolidge Dr, Bloomington, IN 47403

Property at 500 E Dodds St, Bloomington, IN 47401, 2 beds, 1 bath

$319,900

2 beds1 bath2,312 sq ft

500 E Dodds St, Bloomington, IN 47401

Property at 8820 S Strain Rdg, Bloomington, IN 47401, 3 beds, 2 baths

$850,000

3 beds2 baths3,436 sq ft

8820 S Strain Rdg, Bloomington, IN 47401

Property at 619 S Eastside Dr, Bloomington, IN 47401, 2 beds, 1.5 baths

$287,000

2 beds1.5 baths1,614 sq ft

619 S Eastside Dr, Bloomington, IN 47401

Property at 1401 W 6th St, Bloomington, IN 47404, 3 beds, 2 baths

$269,000

3 beds2 baths1,980 sq ft

1401 W 6th St, Bloomington, IN 47404

Property at 918 N Maple St, Bloomington, IN 47404, 1 bed, 1 bath

$145,000

1 bed1 bath600 sq ft

918 N Maple St, Bloomington, IN 47404

Property at 445 W Rogers Rd, Bloomington, IN 47403, 3 beds, 1 bath

$215,000

3 beds1 bath929 sq ft

445 W Rogers Rd, Bloomington, IN 47403

Property at 1205 W 8th St, Bloomington, IN 47404, 2 beds, 1 bath

$199,000

2 beds1 bath702 sq ft

1205 W 8th St, Bloomington, IN 47404

Property at 102 N Clark St, Bloomington, IN 47401, 2 beds, 1 bath

$250,000

2 beds1 bath800 sq ft

102 N Clark St, Bloomington, IN 47401

Property at 2900 N Smith Pike, Bloomington, IN 47404, 2 beds, 1 bath

$299,900

2 beds1 bath1,138 sq ft

2900 N Smith Pike, Bloomington, IN 47404

Property at 5410 W State Road 48 Rd, Bloomington, IN 47404, 3 beds, 2 baths

$349,900

3 beds2 baths2,076 sq ft

5410 W State Road 48 Rd, Bloomington, IN 47404

Property at 2312 S Ford Ave, Bloomington, IN 47403, 2 beds, 1 bath

$234,900

2 beds1 bath1,806 sq ft

2312 S Ford Ave, Bloomington, IN 47403

Property at 5601 S Handy Rd, Bloomington, IN 47401, 2 beds, 1 bath

$175,000

2 beds1 bath800 sq ft

5601 S Handy Rd, Bloomington, IN 47401

Property at 3990 W Forrest Park Dr, Bloomington, IN 47404, 2 beds, 1 bath

$289,900

2 beds1 bath1,300 sq ft

3990 W Forrest Park Dr, Bloomington, IN 47404

Property at 819 S Eagleson Ave, Bloomington, IN 47401, 3 beds, 2.5 baths

$969,900

3 beds2.5 baths3,271 sq ft

819 S Eagleson Ave, Bloomington, IN 47401

Property at 1130 W Briarcliff Dr, Bloomington, IN 47404, 5 beds, 3 baths

$365,000

5 beds3 baths2,664 sq ft

1130 W Briarcliff Dr, Bloomington, IN 47404

Property at 133 N Overhill Dr, Bloomington, IN 47408, 3 beds, 3 baths

$415,000

3 beds3 baths2,444 sq ft

133 N Overhill Dr, Bloomington, IN 47408

Property at 2470 N Mount Gilead Rd, Bloomington, IN 47408, 1 bed, 1 bath

$78,000

1 bed1 bath1,365 sq ft

2470 N Mount Gilead Rd, Bloomington, IN 47408

Property at 2219 S Rogers St, Bloomington, IN 47403, 2 beds, 1.5 baths

$272,000

2 beds1.5 baths2,792 sq ft

2219 S Rogers St, Bloomington, IN 47403

Property at 220 N Adams St, Bloomington, IN 47404, 3 beds, 1 bath

$259,900

3 beds1 bath1,376 sq ft

220 N Adams St, Bloomington, IN 47404

Property at 8798 S Strain Ridge Rd, Bloomington, IN 47401, 2 beds, 2 baths

$1,300,000

2 beds2 baths3,096 sq ft

8798 S Strain Ridge Rd, Bloomington, IN 47401

Property at 331 S Maple St, Bloomington, IN 47403, 3 beds, 1 bath

$239,000

3 beds1 bath1,225 sq ft

331 S Maple St, Bloomington, IN 47403

Property at 321 W Sylvan Ln, Bloomington, IN 47404, 4 beds, 2 baths

$325,000

4 beds2 baths1,748 sq ft

321 W Sylvan Ln, Bloomington, IN 47404

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Based on information submitted to the MLS GRID as of Sat Oct 24 2026. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Vintage Homes for Sale in Monroe County

There are currently 143 vintage homes for sale in Monroe County at a median listing price of $365K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Monroe County stay on the market for 86 days. This map is refreshed with the newest listings in Monroe County every 15 minutes.

In the past month, 120 homes have been sold in Monroe County. In addition to houses in Monroe County, there were also 164 condos, 1 townhouse, and 36 multi-family units for sale in Monroe County last month. Find your dream home in Monroe County using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Monroe County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Monroe County. If you're looking to sell your home in the Monroe County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Monroe County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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