Pittsboro Homes under $400,000

Welcome to Pittsboro, Indiana – a charming small town nestled in the heart of Hendricks County, just a short drive from the vibrant city of Indianapolis. Known for its friendly community and picturesque landscapes, Pittsboro offers a perfect blend of small-town charm and modern conveniences. With a rich history dating back to the 19th century, this delightful town features a quaint downtown area filled with local shops and eateries, making it an ideal place for families and individuals seeking a peaceful yet engaging lifestyle.

For those looking to call Pittsboro home, you'll be pleased to discover a variety of beautiful homes available for under $400,000. Whether you're a first-time buyer, looking to downsize, or seeking a family-friendly neighborhood, Pittsboro has something for everyone. The real estate market here features a mix of charming older homes with character and newer constructions that offer contemporary amenities, ensuring you can find a property that suits your needs and budget.

Living in Pittsboro means enjoying the benefits of a close-knit community while still having easy access to the bustling energy of nearby Indianapolis. With excellent schools, beautiful parks, and a variety of recreational activities, residents can enjoy a high quality of life. Imagine weekends spent exploring the outdoors, attending local events, or simply relaxing in your backyard.

If you’re ready to find your dream home in this idyllic town, Pittsboro awaits you with open arms. Discover the charm of Hendricks County and make Pittsboro your next home sweet home!

Newest Pittsboro Homes under $400,000

$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®

$399,900

3 Beds ⋅ 2 Baths

Welcome to 287 S Woodridge Drive - a rare opportunity in Woodridge Commons, where homes seldom become available. This 3-bed, 2-bath mostly brick ranch offers 1,869 sq. ft. of single-level living and, at only 10 years old, has been kept in tremendous condition. Inside, the kitchen offers extended-height cabinetry and solid-surface countertops with a long breakfast bar that is complemented by a custom tile backsplash and stainless steel appliances. The kitchen opens naturally into the main living area, where a gas fireplace creates a warm focal point for everyday living or entertaining. A separate flex space offers the versatility to serve as a dedicated dining room, home office, or additional sitting area depending on your needs. The primary suite features double sinks and a custom tile shower, creating a comfortable retreat of its own. The thoughtfully designed floor plan provides added privacy by separating the primary suite from the home's two large secondary bedrooms. One of the standout features is the massive 32' x 12' wood deck with railing overlooking a backyard lined with mature privacy trees. It provides an ideal setting for grilling, gathering with friends, or simply enjoying a quiet evening outdoors. A side-load three-car garage with an extended driveway offers exceptional parking options, along with attic access for even more usable storage space. Homeowners also enjoy the convenience of HOA-provided lawn care at an affordable cost, including mowing, aeration, trimming, and mulching - making low-maintenance living even easier. With its exceptional condition, flexible floor plan, impressive outdoor space, three-car garage, and rare availability in Pittsboro, 287 S Woodridge Drive is a property you won't want to miss. Schedule your showing today!

287 S Woodridge Drive, Pittsboro

Listing courtesy of Ryan Nelson. CrestPoint Real Estate

$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

$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

$299,900

3 Beds ⋅ 2 Baths

NEW NEW NEW. Welcome home to this fully updated, turn-key gem offering 3 bedrooms, 1.5 baths, and 1,372 square feet of beautifully modernized living space. Every detail has been refreshed from top to bottom, starting with the stunning brand-new kitchen featuring hardwood shaker cabinets with soft close hardware, elegant quartz countertops, a modern single-basin sink with garbage disposal, and a full suite of stainless steel appliances. Durable, new luxury vinyl plank flooring throughout, updated light fixtures, fresh neutral paint, and new outlets/switches. Flow seamlessly through the bright living room and into the spacious eat-in kitchen. Relax in the cozy family room anchored by a charming fireplace, or step through the sliding glass doors onto your private backyard deck-perfect for outdoor entertaining. Both bathrooms boast brand-new vanities and toilets. Enjoy ultimate peace of mind with major mechanical updates, including a brand-new HVAC system, a new well pressure tank and switch, water proofing crawlspace system with vapor barrier. Almost everything in the house is new.

2656 E County Road 900 N, Pittsboro

Listing courtesy of Michael Powell. United Real Estate Indpls

$344,900

4 Beds ⋅ 3 Baths

**** ASSUMABLE LOAN **** Rare opportunity in Pittsboro with an assumable loan! This well-maintained 4-bedroom, 2.5-bath home sits on nearly half an acre and offers the space and flexibility buyers are looking for. Enjoy an updated kitchen, baths, and flooring throughout, plus a 2-car attached garage with an additional detached garage space, perfect for car enthusiasts, hobbies, projects, or extra storage. With no HOA and convenient access to I-74 and I-65, you'll enjoy the best of both worlds: convenient access to nearby amenities while coming home to a quiet, peaceful setting surrounded by beautiful cornfields. Homes offering this much space, flexibility, and peaceful country-style living in this price range don't come along often. Come see everything this one has to offer before it's gone!

2616 E County Road 900 N, Pittsboro

Listing courtesy of Rebecca Bondurant. Wall and Associates

$399,999

4 Beds ⋅ 3 Baths

What's Special: Walk-In Closets | Flat Lot | Loft. New Construction - November Completion! Built by Taylor Morrison America's Most Trusted Home Builder. Welcome to the Legacy 2432 at 458 Chester Lane in Hidden Hills! This spacious new home features an open-concept design and flexible living spaces throughout. The main level offers a bright great room that flows into the dining area and kitchen, creating the perfect setting for everyday living and entertaining. A versatile flex room near the foyer is ideal for a home office, hobby space, or playroom. The kitchen features a large island, pantry, and ample storage, while the patio extends your living space outdoors. Upstairs, a loft provides additional gathering space, along with three secondary bedrooms, a full bathroom, and a convenient laundry room. Tucked away for privacy, the primary suite offers a spacious bedroom, luxurious bathroom, and oversized 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: 42" upgraded upper kitchen cabinets, water softener rough-in at laundry room, gas line and 110V in kitchen. Photos are for representative purposes only. MLS#22121960

458 Chester Lane, Pittsboro

Listing courtesy of Jerrod Klein. Pyatt Builders, LLC

$345,000

5 Beds ⋅ 3 Baths

Seriously, this is the ONE! "Like new" but with lots of upgrades not typically found in new construction. Fantastic floor plan with 5 bedrooms and 3 full bathrooms, including a bedroom and full bathroom on the main. There's plenty of room for everyone to spread out in this home while providing an open and spacious main living and gathering area. The main level features upgraded luxury vinyl plank flooring (2024), updated lighting, and custom wainscotting entry way with coat hooks. Neutral colors throughout. All stainless kitchen appliances and laundry appliances included. Upstairs features newer carpet (2024), a huge primary bedroom with en-suite, 3 additional bedrooms, full bath, and a loft. The exterior has great curb appeal and back yard features a fence and extended patio and firepit creating a lovely space to entertain and relax. Newer water heater, (2025), and dishwasher (2026). If you're looking for a move in ready home with tastful custom finishes, come see this one and be prepraed to fall in love!

670 Albermarle Drive, Pittsboro

Listing courtesy of Robin Pickett. Blu Nest Realty

$349,900

3 Beds ⋅ 2 Baths

Just What You've Been Looking For - NO HOA! This fantastic one owner home offers the perfect combination of comfortable living, incredible garage space, and an outdoor setup you'll love. The property features an attached garage PLUS a huge detached garage with a workshop, giving you plenty of room for vehicles, hobbies, projects, and storage. Enjoy the HUGE sunroom with barn that leads to the relaxing, fenced-in backyard where you'll find an above-ground pool, large deck, patio area, and two storage sheds-plenty of space to enjoy summer and store everything you need. Inside, you'll love the updated living room featuring a cozy electric fireplace that flows into the dining area, which also boasts an electric fireplace for the perfect ambiance. The updated kitchen features quartz countertops, new cabinets, stainless steel appliances, and waterproof luxury vinyl plank flooring. This home offers 3 bedrooms, including one with brand-new carpet, plus a recently updated hall bathroom. With thoughtful updates, amazing garage and workshop space, a great backyard, and North West Hendricks Schools, this home truly has so much to offer! NO HOA + TWO GARAGES + WORKSHOP + POOL + FENCED YARD = A WINNING COMBINATION!

7360 N County Road 150 E, Pittsboro

Listing courtesy of Lori Redman. Sold It Realty Group

$240,000

2 Beds ⋅ 2 Baths

Bring your ideas and make this one your own! This 2-bedroom, 1.5-bath home offers vintage character, generous living spaces, and plenty of possibilities on approximately half an acre near the heart of Pittsboro. Inside, you'll find a spacious living room with a decorative stone fireplace, an eat-in kitchen, and a separate office/den that could potentially be converted into a third bedroom. Original details throughout give the home a distinctive sense of its era while offering the next owner an opportunity to update and personalize the spaces over time. The property also includes an attached one-car garage, plus a large detached two-story barn that adds a tremendous amount of flexibility. Use it for a workshop, hobbies, equipment, storage, or a combination of all four. The second level provides even more room for storage and future possibilities. Outside, the half-acre lot gives you space to garden, entertain, work on projects, or simply enjoy having a little more room around you. And the location puts you close to Main Street Pittsboro, local dining and shops, Scamahorn Park, and community activities. If you've been looking for a home with character, usable space, and the opportunity to make it truly your own, 50 Terrell Dr is ready for its next chapter.

50 Terrell Drive, Pittsboro

Listing courtesy of Christopher Porter. CENTURY 21 Scheetz

$225,000

3 Beds ⋅ 2 Baths

NEW PRICE!! Looking for a home with great potential and room to make it your own? This 3-bedroom, 2-bath ranch offers 1,118 square feet of comfortable, single-level living and is ready for your personal touch. Built in 2000, the home features a functional layout, attached garage, and a NEW HVAC system. Whether you're looking to add your own style, make some updates, or build equity over time, this home offers a great opportunity. Conveniently located near local amenities with easy access to surrounding communities. Bring your vision and see what you can create here! Schedule your private showing today!

410 Lockerbie Lane, Pittsboro

Listing courtesy of Betty Harris. Carpenter, REALTORS®

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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 Homes under $400,000

Newest Pittsboro Homes under $400,000

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