Middle Real Estate

Middle Real Estate

Welcome to Pittsboro, Indiana – a charming town nestled in the heart of Hendricks County. Known for its picturesque landscapes and tight-knit community, Pittsboro offers a unique blend of small-town charm and modern conveniences, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Situated just a short drive from the bustling city of Indianapolis, Pittsboro provides residents with easy access to urban amenities while maintaining a serene, rural atmosphere. The town boasts a rich history, with roots dating back to the early 19th century, evident in its beautifully preserved architecture and friendly neighborhoods.

Nature enthusiasts will appreciate the abundance of green spaces and parks in and around Pittsboro. With scenic walking trails, playgrounds, and picnic areas, it’s the perfect spot for outdoor activities and family gatherings. The nearby White Lick Creek offers opportunities for fishing and kayaking, ensuring that adventure is never far away.

Pittsboro is also home to a vibrant local community, with various events and festivals throughout the year that foster camaraderie and connection among residents. From farmers' markets to holiday celebrations, there’s always something happening in this lively town.

Education is a priority here, with access to quality schools that focus on nurturing young minds. Families will find a supportive environment for their children’s growth and development.

Whether you’re looking to buy your first home, relocate, or invest in real estate, Pittsboro, IN, offers a welcoming community with a bright future. Discover the charm and opportunity that await in this delightful town!

Newest Listings in Middle

35 S Walnut Street, Pittsboro
$295,000
3 Beds ⋅ 2 Baths
Welcome Home to Easy Living in Pittsboro! This charming 3-bedroom, 2-bath brick ranch offers the perfect blend of classic appeal and everyday functionality. Featuring 1,602 square feet of living space plus an additional 300-square-foot sunroom, there's plenty of room to relax, entertain, and enjoy the home. Freshly painted interior walls and trim and new flooring in the kitchen, breakfast room, family room and laundry room give the home a refreshed feel, making it easy to settle in and make it your own. The inviting sunroom provides the perfect spot for entertaining, morning coffee, a good book, or just enjoying views of the backyard. Outside, the privacy-fenced backyard offers space for pets, gardening, or entertaining, while the mini barn provides convenient extra storage for lawn equipment and outdoor essentials. There are even two small apple trees that produced apples this year! Other perks of this home include a newer furnace, a water softener, and an osmosis system. Great location near the town of Pittsboro and parks, and easy access to I74. If you're looking for one-level living with a spacious sunroom, a private backyard, and the charm of a brick ranch in a small town setting, this home is a must-see!

35 S Walnut Street, Pittsboro

Listing courtesy of Steve Brower. Carpenter, REALTORS®
4501 Quail Creek Trace N, Pittsboro
$350,000
2 Beds ⋅ 2 Baths
LUXURY, LOW MAINTENANCE LIVING in this Beautifully Maintained, FREE-STANDING CUSTOM BRICK CONDO in desirable Quail Creek Estates, adjacent to Quail Creek GOLF COURSE! Step inside to experience the SPACIOUS FEEL of this 1883 sf RANCH w/ UPSTAIRS LOFT & FINISHED 2 CAR GAR. Impress guests from the OPEN DECORATIVE STAIRWAY to the OPEN-CONCEPT DESIGNED GREAT RM with soaring vaulted ceilings and a WALL OF WINDOWS that flows seamlessly into the Generous Gathering Kitchen with maple cabinetry, granite countertops & center island w/ bar stools. The SUNNY Dining/SUNROOM is accented with wainscoting & leads out to the CUSTOM STAMPED CONCRETE PATIO! RETREAT to the PRIMARY SUITE at the end of a day with double vanities, custom mirrors, walk-in shower & large walk-in closet. The POPULAR SPLIT BEDROOM FLOORPLAN places the 2nd Bedroom & FULL BATH with tub/shower combo on the other side of the home. Everything you need is on the MAIN, including convenient LAUNDRY Rm with Cabinets & Utility sink plus consistent NEWER LVP flooring is found throughout the entire Main level! Send Kids, Guests or You can enjoy the EXTRA SPACE in the LARGE LOFT overlooking the Great Room - perfect for a Playroom, Office/Den, Crafts, Exercise or additional GUEST RETREAT! You'll love having the Spacious Rooms & Storage! Conveniently Located between Pittsboro & Brownsburg, with easy access to both towns & Interstate to get where ever you need! Truly a wonderful combination of space, style and easy living in a wonderful sought-after GOLF COURSE COMMUNITY! NOTE: No Homestead Exemption is currently filed, so taxes will be approximately half, if new owner DOES file the Homestead Exemption!

4501 Quail Creek Trace N, Pittsboro

Listing courtesy of Jamie Hall. Carpenter, REALTORS®
10954 N County Road 150 Road E, Pittsboro
$680,000
4 Beds ⋅ 4 Baths
This Gorgeous & Tranquil Country Retreat can be yours! Perfectly maintained 4 BR/4BA traditional w multi levels provides plenty of living space. Walk in to the desirable layout that accommodates plenty of room. Kitchen overlooks the serene views of back property, Paver Patio and Sunroom. Bkfst Rm offers a complete Wet Bar/Coffee Bar. Living Rm boasts wood paneled walls and built in bookcases. Plenty of entertaining space thru-out main level. Huge Great room/game room includes Kitchen & Bar area. The home has been meticulously maintained, featuring all appliances including new HVAC 2025, Tankless Water Heater 2024, Roof 2013 and Fresh Exterior Paint completed in 2025. The property also is equipped with a 400 AMP electrical service. Exterior 35x100 barn, ideal for equipment, animals, storage, or hobby use. Outdoor living includes a large deck, paver patio, and a 3-season sunroom that lets you enjoy the property in every season. An outstanding property you don't want to miss. Nature lover's paradise! Original family owned. Close to the new Lilly Center in Lebanon, I-465, and a 30 min commute to Downtown Indy.

10954 N County Road 150 Road E, Pittsboro

Listing courtesy of Parge June. F.C. Tucker Company
301 Osborne Avenue, Pittsboro
$249,500
3 Beds ⋅ 2 Baths
Charming Pittsboro ranch on a corner lot - walkable to schools and town! This 3-bed, 2-bath home offers hardwood floors, an updated kitchen, a spacious family room, and a bonus room perfect for a home office or playroom. The primary bedroom features hardwoods and easy access to a remodeled bath with a walk-in shower. Enjoy the enclosed sunroom, attached 2-car garage and a large fenced backyard with mature trees. Located directly across from Pittsboro Primary and Elementary - an unbeatable convenience. A solid, well-maintained home with low taxes, municipal utilities, and USDA- eligible financing. Move-in ready and easy to love.

301 Osborne Avenue, Pittsboro

Listing courtesy of Tim Boston. Carpenter, REALTORS®
467 Chester Lane, Pittsboro
$424,999
5 Beds ⋅ 3 Baths
What's Special: 5th Bedroom | Backs to Greenbelt | Large Kitchen Island | East Facing Patio. New Construction - December Completion! Built by Taylor Morrison America's Most Trusted Home Builder. Welcome to the Legacy 3040 at 467 Chester Lane in Hidden Hills! Step into this spacious and thoughtfully designed five-bedroom home. The open-concept main level brings everyone together with a bright great room, expansive dining area, and a kitchen featuring a large island and walk-in pantry. A versatile flex room, private bedroom, and powder bath on the main floor offer flexibility for guests, work, or hobbies. Upstairs, the luxurious primary suite includes a spa-inspired bath, oversized walk-in closet, and a private retreat, while three additional bedrooms and a central loft provide room to grow and gather. With a convenient upstairs laundry room and a three-car garage, this home blends comfort, functionality, and everyday ease. Hidden Hills offers the perfect blend of peaceful Pittsboro and the lively energy of Brownsburg in Hendricks County. Explore growing Downtown Pittsboro with its parks, local spots, and historic charm. Head to Brownsburg to enjoy the B&O Trail, horseback riding at Natural Valley Ranch, West Chase Golf Club, Lucas Oil Raceway, and more outdoor fun. Additional Highlights Include: walk-in shower at primary bath, uncovered patio, and water softener rough-in. Photos are for representative purposes only. MLS#22130756

467 Chester Lane, Pittsboro

Listing courtesy of Jerrod Klein. Pyatt Builders, LLC
5870 Essex, Pittsboro
$685,000
3 Beds ⋅ 4 Baths
Custom built home situated on .68 acre partially wooded lot in Pittsboro's highly sought-after Cambridge neighborhood. Spacious layout w/just under 4,000 Sq. Ft., features 3 BR/3.5 BAs/bonus room & extra room/office in basement, walk-out basement and more. Upon entering you are greeted w/a large foyer and recently redesigned staircase that seamlessly connects you to the dining room, great room & kitchen. Natural light filled great room and kitchen share a gas fireplace and both overlook the pristine and well cared for backyard. Lg. kitchen has wet bar, center island w/gas range & downdraft, built-in oven, microwave that converts to 2nd oven, granite counter tops & ceramic tile flooring. All SS kitchen appliances stay w/home. Notice the breakfast nook area - great place to enjoy your morning coffee. Main level primary bedroom with walk-in closet and private bath was recently remodeled/updated w/new custom built double vanity, quartz counter top, soaker tub, & walk-in tiled shower. 2nd level you will find 2 bedrooms & expansive bonus room. 2 bedrooms share Jack & Jilly style bathroom w/new custom built double vanity, quartz counter top, & new tub/shower combo. Walk-out basement offers family room, full bath, office/bedroom and rec/entertainment area that is plumbed for refrigerator, wet bar/sink - possibly a 2nd kitchen? Basement has potential for in-laws suite w/private access. Basement full bath was also recently updated w/new custom built vanity, quart counter top and new show stall. Once outside the semi private lot showcases multiple wood decks on different levels, TV mount on upper deck, 16x36 inground pool w/automatic cover, mini barn, well cared for yard & landscaping. WiFi - remote enable feature on oven to turn on/off when away; Seller used this feature often. Refrigerator - screen allows you to upload photos;Seller has never used this feature.

5870 Essex, Pittsboro

Listing courtesy of Maria Ridenour. Ridenour Real Estate Services,
287 S Woodridge Drive, Pittsboro
$389,900
3 Beds ⋅ 2 Baths
Single-level living, HOA-provided lawn care, and a side-load three-car garage in Woodridge Commons. Built in 2016, this mostly brick ranch offers 1,869 square feet with three bedrooms, two full baths, and a separate flex room for a home office, dining room, or additional sitting area. The kitchen connects to the breakfast area and living room and features extended-height cabinetry, solid-surface countertops, a tile backsplash, stainless steel appliances, and a breakfast bar. A vaulted ceiling and gas fireplace complement the main living space, while the split-bedroom layout separates the primary suite from the two secondary bedrooms. The primary suite includes a tray ceiling, a large walk-in closet, a double vanity, and a custom tiled shower. Enjoy outdoor dining and relaxing on the rear deck, with mature trees providing screening along the backyard. The three-car garage and extended driveway offer ample parking, with attic access providing additional storage. HOA dues of $350 semiannually-approximately $58 per month-include lawn-care services such as mowing, aeration, trimming, and mulching. Seller is offering a temporary 2-1 mortgage payment buydown, subject to lender approval and agreed terms. Schedule your private showing today!

287 S Woodridge Drive, Pittsboro

Listing courtesy of Ryan Nelson. CrestPoint Real Estate
1707 E County Road 1025 N, Pittsboro
$245,000
Beautiful 3.495-acre homesite offering mature trees and an open clearing ready for your new home. Enjoy the privacy and natural setting of this attractive property while remaining conveniently located in the Pittsboro area. The parcel has been split from a larger tract and is identified as Minor Residential Plat #170/26. Survey stakes are in place, with a legal description and boundaries established for the 3.495 acres. The property is unimproved and will require a private well and septic system. Located south of 1025 N on the east side of County Road 150 E. Bring your plans and builder and make this beautiful setting your own!

1707 E County Road 1025 N, Pittsboro

Listing courtesy of Connie Bowman. Bowman & Associates, LLC
256 Commodore Drive, Pittsboro
$416,999
5 Beds ⋅ 3 Baths
What's Special: 5th Bedroom | Pond View | 3-Car Garage | Primary Retreat. New Construction - December Completion! Built by Taylor Morrison America's Most Trusted Home Builder. Welcome to the Legacy 3040 at 256 Commodore Drive in Hidden Hills! Step into the home you've been dreaming of. A charming, covered porch welcomes you into the foyer, where a versatile flex room and convenient powder room offer space to fit your lifestyle. Continue into the heart of the home, where the open-concept great room, kitchen with a spacious island, and inviting breakfast nook to create the perfect setting for everyday living and entertaining. Just off the garage entry, a first-floor bedroom provides comfort and flexibility for guests or a home office. Upstairs, you'll find three additional bedrooms, a spacious loft ideal for movie nights or relaxation, and a luxurious primary suite featuring a cozy retreat, spa-inspired bathroom, and expansive walk-in closet. Hidden Hills offers the perfect blend of peaceful Pittsboro and the lively energy of Brownsburg in Hendricks County. Explore growing Downtown Pittsboro with its parks, local spots, and historic charm. Head to Brownsburg to enjoy the B&O Trail, horseback riding at Natural Valley Ranch, West Chase Golf Club, Lucas Oil Raceway, and more outdoor fun. Additional Highlights Include: 3-car garage, uncovered patio, tile wall shower with bench at primary bath, and water softener rough-in. Photos are for representative purposes only. MLS#22129165

256 Commodore Drive, Pittsboro

Listing courtesy of Jerrod Klein. Pyatt Builders, LLC
223 Commodore Drive, Pittsboro
$419,999
4 Beds ⋅ 3 Baths
What's Special: Sunroom Included | Flat Lot | Flex Room | 3-Car Garage. New Construction - December Completion! Built by Taylor Morrison America's Most Trusted Home Builder. Welcome to the Legacy 2719 at 223 Commodore Drive in Hidden Hills! This spacious two-story home offers a thoughtfully designed layout with a welcoming covered porch, versatile flex room, and an open-concept great room that flows seamlessly into the dining area and kitchen. Enjoy relaxing in the bright sunroom with direct access to the patio. A half bathroom and three-car garage provide added convenience to the home. Upstairs, the private primary suite features a luxurious bathroom and expansive walk-in closet, while three additional bedrooms, full bathroom, a loft, and convenient laundry room provide plenty of space for everyday living and entertaining. Hidden Hills offers the perfect blend of peaceful Pittsboro and the lively energy of Brownsburg in Hendricks County. Explore growing Downtown Pittsboro with its parks, local spots, and historic charm. Head to Brownsburg to enjoy the B&O Trail, horseback riding at Natural Valley Ranch, West Chase Golf Club, Lucas Oil Raceway, and more outdoor fun. Additional Highlights include: Revwood flooring at great room, tile wall shower with bench at primary bathroom, gas line to kitchen, and water softener rough-in. Photos are for representative purposes only. MLS#22129187

223 Commodore Drive, Pittsboro

Listing courtesy of Jerrod Klein. Pyatt Builders, LLC
502 Osborne Avenue, Pittsboro
$285,000
4 Beds ⋅ 2 Baths
At 502 Osborne AVE, PITTSBORO, IN, a captivating single-family residence built in 1920 offers 2364 square feet of thoughtfully designed living space. This property presents a unique opportunity to embrace a lifestyle of comfort and character. With four well-proportioned bedrooms, there is ample space for rest and personalization. Two full bathrooms provide convenience and functionality for daily routines. Spanning 1.5 stories, this home offers a distinctive layout that maximizes both privacy and shared living areas. The generous 13242 square foot lot provides a substantial outdoor canvas for recreation and relaxation. Discover the potential of this inviting residence and envision your future at 502 Osborne AVE.

502 Osborne Avenue, Pittsboro

Listing courtesy of Rachel Mappes. F.C. Tucker Company
133 Brixton Woods West Drive, Pittsboro
$282,000
3 Beds ⋅ 2 Baths
Lovely Three Bedroom, Two Bath home situated on a superb lot with pond view from the Kitchen and the patio. Even better the house is located next to common area that is maintained by the HOA. Many updates have been made in this home - most of all, in the last couple of years this owner has all windows and atrium door replaced ($30,000 addition expense) which has had a tremendous affect to the utility costs. The majority of floors have waterproof laminate flooring with two bedrooms carpeted. Home features split bedroom floor plan, vaulted ceilings in the Great Room and the Primary Bedroom. Owner has done all she can to make this home appealing to all.

133 Brixton Woods West Drive, Pittsboro

Listing courtesy of Judi Bartley. Berkshire Hathaway Home
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Listings courtesy of MIBOR Broker Listing Cooperative as distributed by MLS GRID.


Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of 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. Some listings have been excluded from this website.


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