Pittsboro Real Estate

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

$699,900
4 Beds ⋅ 4 Baths
Set on a huge corner lot with 1.27 acres, mature trees, and NO HOA, this custom home in Pittsboro's highly desired Cambridge neighborhood is the kind of property that rarely comes available! With 4 bedrooms, 2 full baths, 2 half baths, and nearly 4,000 sq ft of finished living space, this home offers room to spread out without sacrificing character or charm. Step outside and you will find where this home truly sets itself apart! The covered back patio is a true outdoor living room with vaulted wood ceilings, a wood burning fireplace, retractable screens, and an outdoor kitchen complete with granite counters, a built in grill, and a beverage fridge, with views of mature trees giving you peace and privacy. A hot tub adds even more space to unwind in this private backyard retreat. Back inside, the main level welcomes you with real hardwood floors, 2 living spaces, and a kitchen that has been beautifully updated with white cabinetry, granite countertops, stainless steel appliances, and 2 pantries for extra storage. One living room features a cozy gas fireplace and opens to the kitchen with an eat in dining table for everyday living, while a more traditional dining room sits just off the kitchen, finished with custom wall trim that adds instant character. Upstairs, all 4 bedrooms offer walk in closets, including a spacious primary suite with a soaking tub, separate shower, double vanity, and custom board and batten trim on the bedroom walls. A second full bath with double sinks serves the additional 3 bedrooms, and a dedicated private office provides the perfect work from home setup. The finished basement adds even more space to enjoy with its own kitchen and half bath, ideal for hosting! The oversized 3 car garage impresses with a bump out, utility sink, service door, and custom mud room cabinetry built right in! This well loved Cambridge neighborhood, paired with a location close to everything Pittsboro and Brownsburg offer, makes this one hard to pass up!

4665 Devonshire Drive, Pittsboro

Listing courtesy of @properties.

$449,900
3 Beds ⋅ 3 Baths
Custom ranch on a cul-de-sac in the highly sought after Cambridge neighborhood! 3 beds, 2 full baths, 1 half bath & over 2,000 square feet, all in one of Pittsboro's most loved neighborhoods. Out back you'll find your own private retreat, complete with an in-ground pool fenced in on one side of the yard, plenty of open green space on the other for pets or play, & a back deck that ties it all together for summer days spent outside. The home itself has been well maintained and updated inside & out, starting with a front porch perfect for morning coffee, a shed for extra storage, & a lot lined with mature trees for added privacy. Inside, engineered hardwood floors run through most of the main living space, while the living room offers plush carpet, vaulted ceilings & a wood burning stove for a cozy spot to relax. The kitchen looks out over the backyard through a window above the sink, with stainless steel appliances & quartz counters that open easily to a large dining area, perfect for everyday meals or hosting. 2 bedrooms are on the main level, and the primary bath has been totally updated (2023) with tile floors, double sinks, a newer vanity & tile surrounding the tub. The second full bath on the main level has also been updated (2022), with tile floors, a new vanity & tile around the tub. The laundry & mechanical room adds tons of storage with cabinetry & shelving. Upstairs, a private loft offers flexible space for an office, playroom, secondary living area or hangout room, along with a 3rd bedroom tucked off to the side for added privacy. Cambridge is one of those neighborhoods people love & never want to leave, with an unbeatable location close to everything Pittsboro & Brownsburg have to offer!

6056 Canterbury Court, Pittsboro

Listing courtesy of @properties.

$599,900
3 Beds ⋅ 3 Baths
Welcome to 406 Wind Drift CT, a delightful single-family residence in PITTSBORO, IN, built in 2008. This 2978 square foot charmer is in great condition, ready for its next chapter of fun and frolic! Step into the heart of the home, where the kitchen is a culinary playground. Imagine whipping up gourmet delights with stainless steel appliances, all within a G-shaped layout that makes cooking a breeze. A convenient peninsula offers extra counter space for your morning coffee or evening snacks, and a pantry ensures all your goodies are perfectly organized. Plus, a high-end refrigerator keeps everything cool and fresh - just like you! The living room is where comfort meets charisma. Curl up by the fireplace on a chilly evening, or showcase your favorite books and treasures on the built-in shelves. It's the perfect spot for movie nights, board game showdowns, or simply unwinding after a long day. When it's time to refresh, the bathroom offers a spacious layout with a double vanity, featuring two sinks, so there's no more jostling for mirror time. And for a truly invigorating experience, a walk-in shower awaits. One of the bedrooms boasts a lovely tray ceiling, adding a touch of architectural elegance to your private sanctuary. Beyond the interior, you'll find an outdoor dining area, perfect for al fresco meals and entertaining under the stars. The attached garage keeps your vehicles happy and dry, and a convenient laundry room makes chore day a little less of a chore. A patio extends your living space outdoors, offering a sunny spot for relaxation. Ready to add a dash of playful charm to your everyday? Schedule your showing today!

406 Wind Drift Court, Pittsboro

Listing courtesy of F.C. Tucker Company.

$525,000
3 Beds ⋅ 2 Baths
Beautiful home on 2.76 wooded acres with seperate In-Law Quarters/ADU. Main house offers 3 bedrooms, 2 full baths, living room, family/dining room with fireplace, kitchen & laundry/pantry with 2 car garage. Large Pole barn with loft and electric. The In-Law Quarters features large family/dining, kitchen, bedroom with walk in closet, full bath & laundry room. Mulitple decks overlooking wooded acres. Come see today!

4006 E County Road 550 N, Pittsboro

Listing courtesy of Carpenter, REALTORS®.

$309,900
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 and mold remediation. Foundation work including new sill plates, band joist, floor joists and beam. Almost everything in the house is new.

2656 E County Road 900 N, Pittsboro

Listing courtesy of United Real Estate Indpls.

$670,000
4 Beds ⋅ 4 Baths
Welcome to this beautifully maintained 4-bedroom, 2 full and 2 half bath custom-built home situated on 2.63 acres in Hendricks County, offering the perfect blend of space, privacy and comfortable living. A timeless brick exterior and impressive two-story foyer with a beautiful staircase welcome you inside. The open floor plan features a dramatic Great Room with soaring vaulted ceilings and a gas fireplace, adjoining the spacious kitchen with generous cabinetry, casual dining area and pantry. Just beyond, the inviting Sun Room provides another wonderful space to relax while enjoying views of the expansive backyard. The main-level Primary Suite features tray ceilings, a spacious bath with whirlpool tub and separate shower, plus a walk-in closet with custom built-ins. Upstairs, a spacious Bonus Room provides the additional living space you might otherwise look for in a lower level-an ideal place for everyone to spread out and enjoy movie nights, games, hobbies or a separate recreation area. The additional bedrooms offer flexibility for family, guests or working from home. Step outside to enjoy the 2.63-acre setting with a partially fenced backyard, open deck and beautiful sunset views-a peaceful setting with plenty of room to relax, entertain and enjoy the outdoors. Additional highlights include a spacious 3-car garage with service door to the backyard, a roof approximately 4 years old and a recently painted exterior. A wonderful opportunity to enjoy a custom home, generous acreage and beautiful surroundings while still being conveniently located in Hendricks County.

4674 E County Road 1000 N, Pittsboro

Listing courtesy of F.C. Tucker Company.

$339,900
3 Beds ⋅ 2 Baths
Set on 2 parcels totaling 1.01 acres with no HOA and located in the Brownsburg school district, this 3-bedroom, 2-bath brick ranch offers space, flexibility, and a convenient Pittsboro location. A charming covered front patio welcomes you inside, where you'll find a formal living room, kitchen, and a huge family room with fireplace, plus flexible dining and living space to fit your needs. Hardwood floors under the carpet, along with newer windows and a newer back sliding door, add even more value and appeal. The primary suite features an en suite bath and walk-in closet, while the additional bedrooms are all generously sized. The full basement adds exceptional usable space, including a 48-foot recreation area, utility/laundry room, workshop area, and an additional flex room ideal for hobbies, exercise, storage, or office use. Outside, the property also includes a 2-car attached garage with attic stairs for extra storage. The second parcel has its own parcel ID, creating added potential, and public utilities are nearby, with buyer to verify availability and connection options. The location offers quick access to I-74, shopping, dining, the Indianapolis airport, and downtown Indianapolis, making everyday commuting and errands simple. All appliances stay, and the home is being sold as-is, with all contents remaining.

5276 E County Road 550 N, Pittsboro

Listing courtesy of Carpenter, REALTORS®.

$349,900
4 Beds ⋅ 3 Baths
Rare opportunity in Pittsboro! 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 Wall and Associates.

$454,999
5 Beds ⋅ 3 Baths
What's Special: 1st Floor Guest Suite | Pond View | Spacious Kitchen | No Rear Neighbors | Large Kitchen Island. New Construction - November Completion! Built by Taylor Morrison America's Most Trusted Home Builder. Welcome to the Legacy at 427 Chester Lane in Hidden Hills! This spacious two-story home offers five bedrooms, three bathrooms, a private office, flexible living spaces, and room to grow. The open-concept kitchen features a large island, walk-in pantry, and seamless flow into the dining area and great room, creating the perfect setting for entertaining. A first-floor guest bedroom with a nearby full bathroom provides added convenience, while the flex room and dedicated office offer versatility for work or hobbies. Upstairs, the expansive primary suite features a well-appointed bathroom and two generous walk-in closets. Three additional bedrooms, a loft, and second-floor laundry complete this thoughtfully designed layout. 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, water softener rough-in, and tile wall shower with bench at primary bathroom. Photos are for representative purposes only. MLS#22122083

427 Chester Lane, Pittsboro

Listing courtesy of Pyatt Builders, LLC.

$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 Pyatt Builders, LLC.

$414,999
4 Beds ⋅ 3 Baths
What's Special: Sunroom Included | Pond View | Spacious Kitchen | Premium Location | Oversized Pantry. New Construction - November Completion! Built by Taylor Morrison America's Most Trusted Home Builder. Welcome to the Legacy 2719 at 244 Commodore Drive in Hidden Hills! This spacious new home is designed for comfort and flexibility. The open-concept main level features a well-appointed kitchen with a large island overlooking the dining area and great room, plus a walk-in pantry for added convenience. A versatile flex room near the foyer is ideal for a home office, playroom, or hobby space, while the sunroom provides additional living space filled with natural light. Upstairs, the private primary suite features a walk-in closet and spacious bath with a walk-in shower. Three secondary bedrooms, a loft, and a full bathroom with dual sinks provide room for everyone. Enjoy outdoor living on the covered front porch and patio. 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 in great room, gas line in kitchen, and water softener rough-in. Photos are for representative purposes only. MLS#22121958

244 Commodore Drive, Pittsboro

Listing courtesy of Pyatt Builders, LLC.

$485,000
5 Beds ⋅ 4 Baths
Rare Opportunity in Whispering Fields Estates, Pittsboro! Stunning 5-bedroom, 3.5-bath Craftsman-style retreat offering 3,178 square feet of luxury living. Open-Concept Interior blends gathering spaces seamlessly and features primary suites on both the main and upper floors-ideal for multi-generational living, guests, or long-term flexibility. Large, open kitchen with island and desk area is the hub of the home and in full view of great room, breakfast room and your BACKYARD OASIS - oh Yah!! Step outside to an entertainer's paradise featuring a fully fenced backyard, a sprawling patio, and an in-ground pool; ready for summer gatherings. Home features an upper-level loft for movie nights plus a second-floor laundry room for ultimate convenience. 3 car garage provides loads of space. Enjoy the peaceful neighborhood living with rapid access to local dining, shopping, and effortless commuting to Indianapolis via nearby I-74. Don't wait-opportunities in Whispering Fields Estates don't come around often. Schedule your private tour today!

4916 Myrtle Drive, Pittsboro

Listing courtesy of F.C. Tucker Company.

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