Pittsboro Real Estate

Welcome to Pittsboro, Indiana – a charming town nestled in the heart of Hendricks County. With its rich history, friendly atmosphere, and picturesque landscapes, Pittsboro offers a delightful blend of small-town charm and modern conveniences. Just a short drive from the bustling city of Indianapolis, this inviting community provides residents with the perfect balance of tranquility and accessibility.

Founded in the early 19th century, Pittsboro has retained its historic character while embracing growth and development. The town is known for its strong sense of community, where neighbors become friends and local businesses thrive. Residents enjoy a variety of recreational opportunities, including parks, walking trails, and community events that bring people together throughout the year.

Pittsboro’s location is ideal for those who appreciate the serenity of rural living but still want easy access to urban amenities. The town is conveniently situated near major highways, making it simple to commute to nearby cities for work or leisure. Whether you’re exploring the local shops, dining at cozy eateries, or participating in seasonal festivals, there’s always something happening in Pittsboro.

Families will appreciate the highly-rated schools and safe neighborhoods, making it a wonderful place to raise children. With a welcoming spirit and a strong emphasis on community engagement, Pittsboro is not just a place to live; it’s a place to call home.

If you’re considering a move to this delightful town, you’ll find a variety of real estate options that cater to different lifestyles and budgets. Discover the charm of Pittsboro, where every day feels like a warm welcome home.

Newest Listings in Pittsboro

$469,900

5 Beds ⋅ 3 Baths

WOW! Check out this beautiful custom-built ranch with over 3,600 square feet, a full basement, and a 3-car garage! Conveniently located between Brownsburg and Pittsboro, this home sits on a spacious double lot, with a partially fenced backyard and hot tub included! Offering 5 bedrooms with a possible 6th, this open-concept home features high ceilings, hardwood floors, and a spacious great room with a fireplace. The kitchen offers custom cabinetry, a center island, and all appliances included! The main-level primary suite features a tray ceiling and walk-in closet. The full basement offers a spacious playroom/rec room, two bedrooms with egress windows, a full bathroom, an additional flex room or possible 6th bedroom, and unfinished space perfect for storage or a home gym. Additional highlights include fiber cement siding and a 3-car garage. So much space, inside and out, in a fantastic location! Don't miss this one!

824 Declaration Drive, Pittsboro

Listing courtesy of Carl Vargas. F.C. Tucker Company

3 Beds ⋅ 2 Baths

Interior pictures coming soon! ON-SITE REAL ESTATE AUCTION - DECEMBER 1ST @ 6:30 PM. Experience country living at its finest with this well maintained 1,888 sq. ft. farmhouse situated on over 4 acres. Enjoy morning coffee on the front porch and invite guests into this open concept layout featuring an updated kitchen (approximately 5 years old), gas fireplace insert, and spacious living areas designed for comfortable everyday living. Outdoors, you'll find an above-ground pool with surrounding deck, a new Trex deck off the rear patio doors, fenced area, detached garage, utility shed, and two large barns (24'x14'x10' and 26'x24'x16') offering excellent storage, workshop, or hobby farm potential. Property extends beyond the maintained yard area into the adjoining farm ground. Additional features include owned 1,000-gallon and 600-gallon propane tanks, water heater new in 2021, new decking completed last year, and a metal roof approximately 15 years old. Personal property will be offered separately in an online-only auction. OPEN HOUSE: Sunday, November 15th, 2:00-4:00 PM. AUCTION TERMS: Auction held on-site, December 1st at 6:30 PM. Registration requires valid photo ID and proof of funds or lender pre-approval letter. 10% down payment due from successful bidder on auction day, with closing within 30 days. Selling at Auction - Don't Miss This Opportunity to Purchase a Beautiful Country Property with Acreage, Outbuildings, and Endless Possibilities!

2057 E County Road 1025 N, Pittsboro

Listing courtesy of Hannah Knotts. Freije Real Estate

$379,999

4 Beds ⋅ 3 Baths

What's Special: Loft | Flex Room | Front Porch. New Construction - December Completion! Built by Taylor Morrison, America's Most Trusted Home Builder. Welcome to the Legacy 2307 at 215 Commodore Drive in Hidden Hills! This spacious new home is thoughtfully designed for both comfort and flexibility. The open-concept kitchen, dining area, and great room create an inviting space for gathering, while the flex room off the foyer is ideal for a home office, hobby space, or playroom. Upstairs, the private primary suite features a large walk-in closet and well-appointed bathroom, while three additional bedrooms, a loft, and a centrally located laundry room provide room for everyone to spread out. Step outside to the uncovered rear patio, perfect for enjoying the outdoors, and take advantage of the extra storage space in the garage for tools, seasonal decor, or recreational gear. 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: smooth walled stand-up shower in primary bathroom, water softener rough-in located under the stairs, 9' ceiling on main floor, and 42" upper cabinets in kitchen. Photos are for representative purposes only. MLS#22134534

215 Commodore Drive, Pittsboro

Listing courtesy of Jerrod Klein. Pyatt Builders, LLC

$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®

$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®

$525,000

3 Beds ⋅ 3 Baths

Welcome to the highly sought-after Windfield neighborhood! Brownsburg School District! Situated on over an acre, this spacious 3 bedroom, 2.5 bath home offers room to spread out, relax, and entertain. Inside, you'll find a beautiful living space featuring a stunning floor-to-ceiling brick fireplace, creating a warm and inviting focal point. The large living room provides plenty of space for gathering, while the kitchen offers abundant cabinet storage, a cozy breakfast nook, and a separate formal dining room perfect for hosting family and friends. Need even more space? The impressive 31x22 bonus room is currently being used as a movie theater and workout room but could easily be converted into two additional large bedrooms, offering endless possibilities to fit your needs. The primary bathroom received a brand-new remodel in 2026, along with new bedroom flooring. Outside, enjoy the fresh look of the newly painted exterior and deck, plus a new pool liner installed in 2026. The amazing backyard is ready for entertaining, whether you're hosting summer gatherings, enjoying the pool, or simply relaxing in your own private outdoor retreat. With generous living spaces, flexible bonus room options, and an expansive lot in a desirable neighborhood, this home offers the perfect combination of comfort, functionality, and outdoor enjoyment. Don't miss the opportunity to make this wonderful property your own!

6599 Fenway, Pittsboro

Listing courtesy of Sara Westrich. 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

$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®

$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

$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,

$379,900

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

$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

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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.

Pittsboro Real Estate

Newest Listings in Pittsboro

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