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1981 Caledonian Court, Greenwood
$1,150,000
5 Beds ⋅ 6 Baths
Welcome to this exceptional custom-built Greg Allen home in the highly sought-after Highland Park neighborhood, where timeless craftsmanship, luxury, and resort-style living come together on a private, tree-lined homesite. Offering 5 bedrooms and 6 baths, this thoughtfully designed residence blends elegant living with incredible entertaining spaces. The dramatic two-story great room is filled with natural light and flows seamlessly into the gourmet kitchen, showcasing stunning Taj Mahal Quartzite countertops, premium finishes, and generous gathering space. Just beyond, the sunroom overlooks the expansive deck and private backyard, creating the perfect setting for relaxing or entertaining. The spacious primary suite is a true retreat, complete with a sitting area and a recently renovated spa-inspired bath. Additional bedrooms provide ample space for family and guests, including a convenient Jack-and-Jill bath. A main-level bedroom with a full bath offers the flexibility for guests, multigenerational living, or a private home office. The finished lower level is truly one of a kind. Designed for unforgettable gatherings, the custom pub features a built-in cigar exhaust system, kegerator, glass chiller, and pool table area. A dedicated office, workout room, and additional recreation space complete this exceptional level. Step outside to your own private backyard oasis surrounded by mature trees. The in-ground pool features a diving board, brand-new liner, and new cover installed in 2026, while the expansive deck provides the perfect backdrop for summer entertaining. Tucked among the trees, a charming private treehouse adds a unique touch to this remarkable property. With luxury finishes, an outstanding floor plan, and exceptional indoor-outdoor living, this is more than a home-it's a lifestyle opportunity in one of Center Grove's premier neighborhoods.

1981 Caledonian Court, Greenwood

Listing courtesy of Denis O'Brien. Keller Williams Indy Metro Partners
1091 Margate Drive, Greenwood
$720,000
5 Beds ⋅ 5 Baths
Stunning 5-BEDROOM home offering just under 5000SQFT, an incredible 18x40 HEATED IN-GROUND POOL, FINISHED BASEMENT, 3-CAR GARAGE, & oversized MAIN-LEVEL GUEST SUITE! Beautifully maintained w/ numerous upgrades, exceptional entertaining spaces, & valuable extras included! Your own backyard retreat awaits w/ the 18x40 HEATED POOL! Installed in 2024, it features an automatic cover, sun deck, underwater lighting, upgraded liner, & energy-efficient heat pump. COVERED & OPEN PATIOS provide space for outdoor dining, entertaining, & relaxing poolside with a POND VIEW! The OPEN-CONCEPT main level features a spacious great room, dining area, & GOURMET KITCHEN w/ a large CENTER ISLAND, granite countertops, tile backsplash, vent hood, generous pantry, & upgraded refrigerator. A beautiful STONE FIREPLACE creates a stunning focal point in the dining room. The dedicated OFFICE with bay windows offers a comfortable work-from-home space, while the oversized 20x12 MAIN-LEVEL BEDROOM SUITE provides incredible flexibility for guests, multigenerational living, or a main-level primary retreat. Upstairs, the spacious PRIMARY SUITE offers a large walk-in closet, double vanities, garden tub, & separate shower. Three additional bedrooms feature WALK-IN CLOSETS, upgraded ceiling fans, & window coverings. An additional full bath & convenient upstairs laundry room w/ utility sink & extra storage complete the upper level. The FINISHED BASEMENT offers even more room to spread out, featuring a wet bar, game room w/ POOL TABLE INCLUDED, theater/family room w/ TV, dedicated workout area w/ GYM EQUIPMENT INCLUDED, & abundant storage. Additional upgrades include 3-CAR GARAGE w/ epoxy flooring, whole-home humidifier, water softener & purifier, radon mitigation system, smart thermostat, & numerous improvements. POOL EQUIPMENT & RIDING MOWER also included! Convenient location to both Greenwood & Center Grove schools (open enrollment), Freedom Springs, & shopping, dining, & recreation. Don't miss it!

1091 Margate Drive, Greenwood

Listing courtesy of Jessica Carl Roof. Highgarden Real Estate
1402 Hove Drive, Greenwood
$590,000
4 Beds ⋅ 3 Baths
Discover an exceptional opportunity at 1402 Hove DR, GREENWOOD, IN, USA. This 2022 single-family residence, spanning 4245 square feet of living area, offers a truly luxurious living experience with its impeccable condition, amazing design, and top-tier materials. The heart of this home, the living room, impresses with its soaring high ceiling, creating an expansive and inviting atmosphere for both relaxation and entertaining. This magnificent French Provincial-style residence, set on a generous 15594 square foot lot, features four comfortable bedrooms and two full bathrooms, along with an additional half bathroom for convenience. The great room provides further flexible living space, perfect for a variety of activities. To truly appreciate the sophisticated design and superior craftsmanship of this home, schedule your private viewing today.

1402 Hove Drive, Greenwood

Listing courtesy of Sarabjit Sikand. Legacy Homes International
4023 Cedar Hills North Drive, Greenwood
$3,499,999
5 Beds ⋅ 7 Baths
Welcome to this private luxury estate in the heart of the Center Grove community. This unique property offers unparalleled privacy and luxury living. This home has been meticulously transformed into a stunning property, boasting over 14,000 square feet of exquisite craftsmanship and design. Step inside to discover a warm and inviting atmosphere, perfect for both entertaining and family gatherings. The main level features two primary suites, along with bar, sports style pool with gas grill hook up and window access to the indoor bar and beautiful game area on the main floor. A formal dining room sets the stage for elegant meals, while the stunning gourmet kitchen is a chef's delight, equipped with luxury amenities and a spacious island that opens into the expansive great room with breathtaking views along with brand new Maple Hardwood floors and offers a souring 20 foot coffered ceiling that makes it feel so grand with decorative columns that add a touch of classic elegance. Cold in the winter? Enjoy one of your 4 fireplaces throughout the home. The main level also includes an additional apartment style kitchen connected to a separate family/seating room with fireplace and 2nd laundry and office. The upper level offers two bedrooms that include Jack & Jill bath with each having their own separate sink and endless storage. The lower level offers a breathtaking view of the front of the property with huge family room, private bedroom and bathroom, a home gym, amazing home theater with 109" screen, an additional family room & spa that includes an indoor hot tub & sauna. It also includes another home office and huge storage room. But wait, there's more! 6 car courtyard garage, terrace with heated sport style pool, 32x60 shop plus 20x28 garage attached (with epoxy floors with new siding, roof and gutters). There is a heart shaped pond stocked with fish! Basement also includes safe room with land line for valuables OR natural disasters. it's a must see!!

4023 Cedar Hills North Drive, Greenwood

Listing courtesy of Scott Weddle. F.C. Tucker Company
4064 Shady Pointe Row, Greenwood
$510,000
3 Beds ⋅ 4 Baths
Are you looking for a custom built home near Hickory Stick? Well this only 2 owner home is ready for you to move in and make it your own! This home is a short sale situation. This stately beauty offers an expansive list of upgrades including grand 2 story foyer accented in french stone, breakfast room & formal dining room w/tray ceiling & crisp white pillars. Sunken 2 story great room w/gas log fireplace, chef's kitchen w/cherry soft-close cabinets, professional grade appliances including gas cooktop w/grill & pot filler tap, stainless steel hood w/warming rack, convection oven & microwave. Office w/custom woodwork could be main level 4th bedroom. Primary Bedroom w/tray ceiling & WIC + private bath w/double sink vanity, separate tub & W/I shower. The finished basment theatre room offers a 1/2 bath, full wet bar w/double wine fridge & dimmable lighting + projector, screen, surround sound stay! 50yr. roof only 4 year old.

4064 Shady Pointe Row, Greenwood

Listing courtesy of Andrew Prince. CENTURY 21 Scheetz
2239 Summer Shore Drive, Greenwood
$415,000
5 Beds ⋅ 4 Baths
If space is on your wish list, this one delivers! With over 3,700 square feet, five bedrooms, three and a half baths, and a finished basement, this Greenwood home offers an incredible amount of room to live, relax, and entertain. The layout gives you plenty of places to gather while still providing those extra spaces that make everyday life a little easier. On the main level, a private office is tucked away from the main living areas, giving you a great spot to work from home or simply enjoy a little quiet. The kitchen is open to the living room and features a large center island with breakfast bar seating, making it easy to cook, visit, and stay part of the conversation. A cozy fireplace adds warmth to the living area and makes it an inviting place to unwind. Upstairs, you'll find four spacious bedrooms along with a loft that works beautifully as a second living area, media room, playroom, or reading space. The finished basement adds an entire additional level to enjoy, with a large recreation room, fifth bedroom, and full bath. It's perfect for overnight guests, movie nights, a home gym, game room, or simply having extra room when everyone is home. Outside, sliding glass doors lead to a pergola-covered patio that's just waiting for morning coffee, dinner outside, or a relaxing evening. The fully fenced backyard gives you even more space to enjoy. And when it comes to location, you'll love being close to Greenwood shopping, restaurants, and major routes, with downtown Indianapolis approximately 25 minutes away. With over 3,700 square feet of finished living space and room for everyone and then some, this is a home you'll want to see in person!

2239 Summer Shore Drive, Greenwood

Listing courtesy of Cindy Stockhaus. Better Homes and Gardens Real Estate Gold Key
4261 W Stones Crossing Road, Greenwood
$1,600,000
6 Beds ⋅ 6 Baths
You won't find 5 private, secluded acres this close to everything else in Center Grove - this is that rare exception. Just minutes from schools, shopping, dining, and I-69, with easy access to both Indianapolis and Bloomington, this exceptional custom estate sits on 5.52 park-like acres that feel worlds away from it all. The home offers a fresh new look, with recent updates including new interior paint, updated lighting, brand-new carpet, and a newly sealed aggregate driveway - showcasing it at its very best. The residence includes a heated seven-car attached garage with epoxy floors, ideal for car collectors, hobbyists, or a workshop. Beyond the home, enjoy natural beauty and wildlife, along with lighted tennis, pickleball, and basketball courts, plus an expansive deck set among mature trees with full irrigation and an invisible fence. Inside, hardwood floors, beautiful woodwork, and exceptional craftsmanship throughout reflect the care this custom home was built with, complemented by abundant natural light and a thoughtful floor plan built for both everyday living and entertaining. The great room opens to a spacious kitchen, while the living room's fireplace anchors a warm, inviting space. Upstairs, six generously sized bedrooms include four private en-suites and a dedicated office with custom built-ins. The finished lower level adds a full bar, pool table, and family room - built for hosting. Set in the highly sought-after Center Grove School District, this one-of-a-kind estate blends timeless craftsmanship and refined comfort. Schedule your private tour today.

4261 W Stones Crossing Road, Greenwood

Listing courtesy of Natalie Latkowski. Mark Dietel Realty, LLC
1206 Barrington Drive, Greenwood
$359,900
5 Beds ⋅ 4 Baths
This Center Grove Community home in Barrington West of Greenwood offers a refined living with 4 BRs, a possible 5th or a Bonus room with a full bath in Walk Out basement, 3.5 Baths and a 2 car Attached garage with ample of parking space. Other great features include extended driveway, a grandeur 2-story high foyer and multilevel decks. Main level includes a Den/Library room, a cozy Great Room with gas log fireplace, a powder room, a dining room with a spacious kitchen. Kitchen comes with granite countertops, center island, a large pantry and kitchen appliances. Upper Level offers 4 BRs, Full baths with double sinks, and a convenient laundry room. Primary Suite offers Cathedral ceilings, Walk in closets, a full shower stall and double sinks. A finished walk out basement offers great entertainment area with tile floorings as well as a Family room with carpet flooring, and a bonus room with full bathroom. Built in 2000, Roof was replaced in 2022, Recent Flooring updates include flooring in Kitchen, Loft area, Living Room, and staircase. Home offers a blend of functionality and style ensuring a refreshing start or end to each day. This home provides a generous outdoor space for recreation and relaxation. From grandeur entrance to amazing outdoors, it offers an exceptional opportunity for comfortable living. This is a perfect place to create lasting memories. A must see.

1206 Barrington Drive, Greenwood

Listing courtesy of Chancung Lian. Mang Tha Real Estate, LLC

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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