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53 W Pearl Street, Greenwood
$268,900
3 Beds ⋅ 2 Baths
Experience the charm of downtown living in this inviting 3-bedroom, 1.5-bath cottage-style home, ideally situated in the heart of Greenwood just off Main Street. A welcoming covered front porch sets the tone, offering the perfect spot for morning coffee or unwinding at the end of the day. Inside, raised ceiling heights, abundant natural light, and a neutral color palette create a warm, airy atmosphere. The open-concept living area flows seamlessly into the eat-in kitchen, featuring white cabinetry, contrasting black hardware and accents, pendant lighting over the breakfast bar, a stylish backsplash, stainless steel appliances including a new refrigerator, and a pantry. The primary bedroom stands out with French doors, while the second bedroom features decorative wall trim. Privately positioned toward the rear of the home, the third bedroom offers flexibility for guests, a home office, or additional living space. A full tiled bathroom is conveniently located near the primary and second bedrooms, while a centrally located half bath adds convenience for guests. Select bedrooms feature updated ceiling fans and dimmer lighting.Outside, enjoy a spacious backyard with a patio, open wood deck, and mini shed for additional storage. The unfinished basement provides valuable storage space and houses the home's mechanicals, including a water softener and dehumidifier. Enjoy a walkable lifestyle with local restaurants, coffee shops, the library, Greenwood Fieldhouse, shopping, and everyday conveniences nearby, along with easy access to I-65 and US-31. With its inviting character, functional layout, outdoor living spaces, and desirable downtown location, this home offers the opportunity to enjoy the convenience and charm of Greenwood living-all with no HOA.

53 W Pearl Street, Greenwood

Listing courtesy of Tana Smythe Turner. Smythe & Co, Inc

450 S Valley Lane, Greenwood
$399,999
3 Beds ⋅ 3 Baths
Welcome to this Completely Updated All brick Ranch home with daylight finished basement that sits on almost 1/2 an acre of land in the rolling valley of greenwood! This attractive raised ranch is more than just a home; it's a playful invitation to a life well-lived. There are SO many updates in this home that there are too many to mention them all. A few features include a completely updated kitchen featuring granite counter tops, Huge farm sink, stainless appliances and kitchen island on wheels! The kitchen is a culinary playground with its G-shaped layout and a peninsula that practically begs for impromptu breakfast bar gatherings or lively cocktail prep. Imagine whipping up your favorite dishes with ease and flair! Primary bedroom has an addition that was added onto the home to include a primary bathroom and Indulge yourself in a spa-like experience in the primary bathroom, featuring a grand double vanity that promises plenty of elbow room for your morning routine. And for those moments when you need to wash away the day, indulge in a spacious walk-in shower and then open your frosted barn door into a custom walk in closet with built ins. With three full bathrooms and three cozy bedrooms, everyone can find their happy place in this charming home. The private partially black aluminum fenced yard offers a secret garden escape, perfect for sunny afternoons or starlit evenings, and a Custom Shed that provides a convenient hideaway for your chariot, or she shed or man cave. Ready to add a dash of joy to your everyday? Come discover this Custom built house that has been completely updated from top to bottom and imagine all the possibilities.

450 S Valley Lane, Greenwood

Listing courtesy of Sheila Davis. Sheila Alvarez Brunette Realty

4288 Aurelius Drive, Greenwood
$1,799,900
5 Beds ⋅ 5 Baths
Welcome Home to Homes by Nest's Latest Design, SINCLAIR! Not All Houses Immediately Feel Like Home- but Sinclair Brings a COZY, Luxurious Vibe Right from the Foyer! Timeless Trim Work and Extra Large Windows of Natural Light bring just the Right Mix of Old & New! The Main Floor of Sinclair has been Designed Carefully to Balance Airy, Light-Filled Sightlines w/ Functional Room Separation! Engineered Hdwds Welcome you to the Vaulted Great Rm w/ Beams, Bookcases + Dreamy Trim that opens to a Neutral, Warm Kitchen of Custom Designed Cabinetry, Hidden Appliances + Oversized Island! A Dual Swing Pantry Door provides Maximum Ease of Use for both Adults AND Kids! A Formal Dining Space Overlooks the Backyard + Opens to the Covered Patio! Can you find the HIDDEN study? A Private Hall on the Main Level Leads to the ULTIMATE Primary Suite! Vaulted Bdrm, Spacious Walk In Closet + Private Bath w/ Over 40SF of ZERO THRESHOLD Tile Shower, a Freestanding Tub w/ a View and Dual, Custom Vanities! Sinclair Includes a Main Floor Laundry Rm w/ Sink and Large MUD RM w/ Custom Built-In Lockers, Drop Zone + Charging Drawer. A Sunshine- Filled Staircase takes you to both the Second and Lower Levels! Upstairs includes 3 Additional Bdrms. 2 Bdrms share a Jack & Jill Bath, and 1 Bdrm includes a PRIVATE Ensuite Bath. 2ND Laundry Rm for MAX Convenience! Head Downstairs to TWO Spaces for Entertainment PLUS a Spacious Wet Bar w/ Pretty, Paneled Appliances - Fridge + DW DRAWER! Private Guest Suite w/ Egress Window + Full Bath w/ Tile Shower! Fun Kids' Play Area Under the Stairs! Sinclair has over 1200SF of GARAGE w/ 4 Bays and is ready for an EV Car Charger! The Feature Highlight of Sinclair could quite possibly be the Dramatic, VAULTED PORCH w/ Statement Two Story Gas FIREPLACE! This is the place for Evening Relaxation! Sinclair is located in CG's latest development, PRATI. Prati is the Best of Both Worlds- 36 Homesites for a Neighborhood Feel but Larger Lots + a Gated Entrance for Some Privacy!

4288 Aurelius Drive, Greenwood

Listing courtesy of John Stone. Blubird Real Estate

1055 Old Eagle Way, Greenwood
$675,900
4 Beds ⋅ 3 Baths
Custom-built by J. Greg Allen and located in the heart of the Center Grove school district, this spacious ranch in Eagle Trace offers high-end finishes, thoughtful design, and plenty of room to live, work, and entertain. The main level features rich hardwood floors, a beautiful primary suite, spacious kitchen with expanded cabinetry and counter space, and a split-bedroom floor plan with convenient Jack and Jill-style access between the second bedroom and full bath. Remote-controlled blinds add everyday convenience, while the fully screened back porch provides the perfect spot to relax and enjoy the peaceful surroundings, rain or shine. The full basement adds two additional bedrooms with egress windows, a full bathroom, finished living space, a pool table that stays, and an abundance of storage. Convenient access behind the finished space makes it easy to connect electronics and equipment for the basement or throughout the home. Additional features include a side-load three-car garage and extensive attic storage with pull-down access from the garage. Recent updates include a new roof and gutters in 2024, new HVAC in May 2025, a new fence in May 2025, new GE and GE Profile appliances spring of 2026, and freshly painted exterior trim in September 2026. Eagle Trace is known for its 222 beautifully landscaped custom homes, mature tree-lined streets, and welcoming atmosphere. The neighborhood offers miles of opportunities to walk, run, bike, rollerblade, or simply enjoy the outdoors without crossing busy intersections. With its combination of beautiful homes, peaceful streets, and room for every stage of life, Eagle Trace is a special place to call home.

1055 Old Eagle Way, Greenwood

Listing courtesy of Nathan Inskeep. Highgarden Real Estate

4664 Fox Moor Lane, Greenwood
$730,000
4 Beds ⋅ 4 Baths
This Coopenhaver custom-built ranch offers nearly 5,000 square feet of living space with a finished walkout basement and a layout designed to take full advantage of the mature setting. Just inside opens to an inviting foyer with an open dining room and a light-filled living room featuring hardwood floors and a double-sided gas fireplace. The kitchen offers an abundance of cabinet and countertop space, stainless steel appliances, center island with seating, breakfast nook, and the opposite side of the fireplace, plus a large picture window and access to the enclosed porch. The primary suite features dual vanities with a separate makeup station, dual closets including a walk-in, linen storage, step-in shower, and freestanding tub. Two additional main-level bedrooms share an updated Jack and Jill bathroom with a tiled step-in shower. The finished walkout basement provides plenty of additional living space with a large family room featuring another double-sided fireplace and direct access to the covered patio. A spacious private office enjoys the other side of the fireplace, while a fourth bedroom and updated full bathroom provide a comfortable space for guests. An exercise room and generous utility and storage areas round out the lower level. Outdoor living is tucked into the mature backyard with a private deck just off the enclosed porch and a shaded concrete patio below. With 4 bedrooms, multiple living and entertaining spaces, a walkout basement, and nearly 5,000 square feet, this home offers the space and character you would expect from a custom-built Center Grove home.

4664 Fox Moor Lane, Greenwood

Listing courtesy of Ryan Moriarty. Weichert, Realtors-Tralee Prop

2307 Willow Lakes East Boulevard, Greenwood
$564,900
4 Beds ⋅ 3 Baths
Welcome to this spacious all-brick custom home featuring 4 impressive BR's with walk-in closets, 3 Baths & a 3-car garage. This home is designed for everyday living, space to entertain or room to grow. 4th BR is used as an office. The heart of the home is a delightful kitchen with cherry oak cabinets, abundant workspace, island, pantry, & breakfast bar adjacent to the great room with a fireplace. Separate DR for holiday gatherings. The basement provides exceptional flexibility for a recreation room, media room, home gym, office and ample storage. Step outside to enjoy the screened porch and a brand-new deck, offering multiple spaces for relaxing, entertaining & outdoor BBQ's. Sports enthusiasts will love the private basketball court offering fun right at home. Schedule your private showing today!

2307 Willow Lakes East Boulevard, Greenwood

Listing courtesy of Deanna Jackson. Carpenter, REALTORS®

4438 Hickory Grove Boulevard, Greenwood
$859,000
4 Beds ⋅ 3 Baths
On a scale of 1-10, this is a true "11"! Welcome home to your custom luxury residence, situated in the prestigious neighborhood of Hickory Stick Golf Course. Owners have added over $250k in updates and improvements within the last three years! Amenities galore, including but not limited to: custom modern iron railings, all new upgraded windows, new hickory hardwood flooring throughout, massive stamped concrete patio, professional landscaping with irrigation and outdoor lighting, quartz filled bathrooms and kitchen boasting extensive countertop space, an executive front office, extensive storage, large main floor primary en-suite with oversized sitting area, a basement that doubles as a large workout space complete with pitching/batting cage. Your dream home is complete with a private lot, encompassing both a gorgeous view of the pond and the 9th hole!

4438 Hickory Grove Boulevard, Greenwood

Listing courtesy of Joshua Vida. Paradigm Realty Solutions

1324 Eagle Valley Drive, Greenwood
$777,000
6 Beds ⋅ 5 Baths
An EXTRA $5,000 reason to FALL in love with this home! The seller is offering a $5,000 buyer INCENTIVE toward closing costs or an interest rate buydown. Two-story living room features soaring ceilings and gas fireplace. Two ELEGANT arched windows fill the space w/natural light. Professionally painted interior features newer carpet, updated lighting and ceiling fans. Plantation blinds ADD a nice finishing touch. A dramatic 72-inch statement ceiling fan makes the living rm even MORE impressive. The main-level primary suite features an elegant tray ceiling, new flooring, and a spa-inspired bathroom w/Jacuzzi tub, separate walk-in shower, and Bluetooth-enabled exhaust fan. WAIT until you see the custom walk-in closet, professionally designed to keep everything organized! The kitchen features granite countertops, a center island, tile backsplash, and a large walk-in pantry. The LG Smart InstaView Door-in-Door refrigerator offers Wi-Fi connectivity, filtered water and even a craft ice maker. The breakfast area opens to a sunroom surrounded by windows. Four generously sized bedrooms upstairs, each with ample closet space, along with two full bathrooms. Need even MORE room? The finished basement delivers - family room, game room, sixth bedroom, full bathroom, utility room, and a bonus space previously used as a wine room. Imagine a home gym, hobby room, wine cellar. Beautifully landscaped and fully fenced backyard. A spacious garage and wide driveway provide plenty of parking and additional storage. ADDITIONAL improvements include a newer roof, gutters and flashing, an HVAC system approx six years old, two water heaters (one replaced less than a year ago), a PureSoft Hague water filtration/softening system, whole-home air purification, and a sump pump w/battery backup. Smart home conveniences include an Ecobee thermostat with app access, a Wi-Fi enabled front door smart lock, and a Vivint security system panel. Updated exterior garage lighting adds ANOTHER finishing touch.

1324 Eagle Valley Drive, Greenwood

Listing courtesy of Ema Boykova. M & E Realty Group

1091 Margate Drive, Greenwood
$720,000
5 Beds ⋅ 5 Baths
Stunning 5 BEDROOM home with nearly 4800 sqft, 18x40 HEATED POOL (only 2 years old), FINISHED BASEMENT, 3-car garage, & private MAIN LEVEL GUEST SUITE. Beautifully maintained & ready for its new owner. The backyard oasis has a heated, IN-GROUND POOL (installed 2024) featuring an automatic cover, underwater lighting, sun deck, upgraded liner, & energy-efficient heat pump. COVERED AND OPEN PATIO spaces create an incredible setting for gatherings, relaxing poolside, & enjoying evenings at home. Inside, the OPEN-CONCEPT main level connects the spacious great room, dining area, & GOURMET KITCHEN featuring a large CENTER ISLAND, granite countertops, tile backsplash, vent hood, generous pantry, & upgraded refrigerator. Enjoy entertaining or cozy meals at home w/ the stunning dining room STONE FIREPLACE as your backdrop. A large dedicated OFFICE w/ bay windows provides ideal work space & the oversize 20x12 MAIN-LEVEL BEDROOM SUITE offers flexibility for guests, multi-generational living, or even as the primary bedroom. Upstairs, the spacious PRIMARY SUITE features a large walk-in closet, double vanities, garden tub, & separate shower. Three additional bedrooms each offer WALK-IN CLOSETS, upgraded fans, & window coverings. Second full bath & spacious laundry room w/ wash tub & extra storage also conveniently upstairs. The FINISHED BASEMENT adds more living & entertaining space w/ a wet bar, game room (POOL TABLE STAYS), theater/family room, dedicated gym area (EQUIPMENT STAYS!), & abundant storage. Additional highlights include 3-car garage w/ epoxy flooring, whole-home humidifier, water softener & purifier, radon system, smart thermostat, & numerous seller improvements. POOL EQUIPMENT & RIDING MOWER remain, making this home truly ready to enjoy. Convenient location to both Greenwood & Center Grove schools, Freedom Springs, & shopping, dining, & recreation.

1091 Margate Drive, Greenwood

Listing courtesy of Jessica Carl Roof. Highgarden Real Estate

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

1266 N Morgantown Road, Greenwood
$414,900
3 Beds ⋅ 2 Baths
Beautifully updated 3BR brick/limestone ranch in prominent Center Grove with NO HOA on nearly 1/2 acre! This 3,428 sq ft home features a main-floor layout with a partially finished basement, including a large rec room and versatile bonus room. Fully remodeled in 2021 with luxury PVC wood flooring, wide baseboards, crown molding, and a gourmet kitchen boasting 42" soft-close cabinets and 2021 appliances. Cozy up to both gas and wood-burning fireplaces. Massive capital updates provide ultimate peace of mind: New roof & garage doors (2025); Master bath remodel, water heater, front porch, & serviced septic (2024); Full exterior paint & gutters (2021); and new windows with a transferable warranty (2019). Fully plumbed for gas or electric. The spacious backyard features a mini-barn with electricity and a dedicated electrical hookup for a pool. Washer/dryer negotiable. Move right in!

1266 N Morgantown Road, Greenwood

Listing courtesy of Karen Hogan. Carpenter, REALTORS®

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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