Jaystarr.com Search Results

$685,000

Own a remarkable piece of Greencastle history with the iconic Gilland Guest House, located at 101 E. Baltimore Street. Built around the turn of the 20th century by Dr. Gilland as both his medical practice and family residence, this stunning Victorian property offers a rare investment opportunity filled with quality craftsmanship and immediate, proven income potential. Unlike many converted homes, this property was originally designed to accommodate multiple living spaces and currently features four one-bedroom apartments, with the potential to create a fifth unit on the third level. Each apartment has been thoughtfully updated to preserve the building's historic charm while providing the modern conveniences today's tenants desire, including in-unit laundry facilities and off street parking. Timeless architectural details are found throughout, including beautifully preserved hardwood floors, intricate Victorian woodwork and moldings, reglazed tile, and original hand-crafted oak shutters that adorn every window. The attention to detail and quality of construction are a testament to a bygone era rarely found in today's properties. Situated in the heart of downtown Greencastle, this property offers strong rental appeal with walkable access to local shops, restaurants, and community amenities. Conveniently located less than two miles from Interstate 81, residents have easy commuting access north and south, with Frederick, MD and Carlisle, PA both approximately 44 miles away. Whether you're looking to expand your investment portfolio or own a truly distinctive historic property with reliable cash flow, the Gilland Guest House presents a rare opportunity to own one of Greencastle's most treasured landmarks.

101 E Baltimore St, Greencastle

Listing courtesy of Samson Properties. Contact: 7033788810

$609,900

Video Tour is a MUST SEE! Ask for it Today! Where Luxury Lives — And Nature Awaits Just Beyond Your Back Door This brick colonial in the Greencastle Greens Golf Community delivers over 4,650 finished square feet of thoughtfully upgraded living space — and then offers something truly rare: your own private pathway to nature, steps from the Conococheague Creek. From the moment you enter, the scale and quality make an impression. The gourmet kitchen is where this home truly earns its reputation. Stretching 26x13 feet with over 40 feet of counter space, this is a kitchen that handles everything from quiet weekday breakfasts to full holiday gatherings without breaking a sweat. The 10-foot island anchors the space beautifully, wrapped in Kashmir White granite and surrounded by LifeArt solid wood cabinetry with furniture-grade finishes, dovetail drawer construction, 42-inch wall cabinets, and 65 soft-close doors and drawers — including three glass-front display cabinets that add a touch of elegance. A gas cooking range, stainless appliances, convenient pantry, recessed lighting, casement windows, and a reverse osmosis drinking water system complete a kitchen that is as functional as it is stunning. A sliding door opens directly to the rear deck, making outdoor dining effortless. The sunken family room — with its gas fireplace and French doors — flows seamlessly to a 30x14 rear deck overlooking a wooded backdrop built for every season. Upstairs, the primary suite is a world of its own: trayed ceilings, a private sitting room with a gas fireplace, an intimate morning coffee balcony, and a spa-inspired bath complete with dual vanities, a jetted soaking tub, and a glass walk-in shower. The lower level raises the bar entirely — a 48-foot rec room anchored by a 17-foot horseshoe granite wet bar with Brooklyn loft-style brick wall accents, a full bath, and a dedicated theater room with projector and screen. For peace of mind in 2020 the roof had a major upgrade to 50 Year Long-Life, IKO Dynasty/Cambridge Architectural Shingles and to give additional comfort and security, the heat pumps have been recently replaced; one in 2021 and the other in 2023. Then step outside — and let the land tell its own story. A short walk through your wooded backyard opens up to over an acre of flat, open ground a few steps from the banks of the Conococheague Creek — and what awaits you there is nothing short of remarkable. This is the kind of land that invites you to slow down and build something meaningful. Pitch a tent and wake up to wild flowers and bird songs. Raise a pavilion for family gatherings under the trees. Carve out a meditation space where the sounds are mostly water, wind, and wildlife. Watch deer slip quietly through the tree line. Listen to ducks and geese settle onto the creek at dusk. Spot wild turkey moving through the brush, and squirrels working the canopy overhead. As evening falls, the soundtrack shifts — spring peepers, crickets, tree frogs, and the distant call of an owl fill the air in a way no playlist ever could. Why drive fifty miles for a weekend escape when yours is already waiting, just steps from your back door? Located in the sought-after Greencastle-Antrim School District, minutes to I-81, with recent upgrades throughout. Schedule your private tour today and experience everything this extraordinary home — and its land — has waiting for you.

4 Beds ⋅ 4 Baths

Video Tour is a MUST SEE! Ask for it Today! Where Luxury Lives — And Nature Awaits Just Beyond Your Back Door This brick colonial in the Greencastle Greens Golf Community delivers over 4,650 finished square feet of thoughtfully upgraded living space — and then offers something truly rare: your own private pathway to nature, steps from the Conococheague Creek. From the moment you enter, the scale and quality make an impression. The gourmet kitchen is where this home truly earns its reputation. Stretching 26x13 feet with over 40 feet of counter space, this is a kitchen that handles everything from quiet weekday breakfasts to full holiday gatherings without breaking a sweat. The 10-foot island anchors the space beautifully, wrapped in Kashmir White granite and surrounded by LifeArt solid wood cabinetry with furniture-grade finishes, dovetail drawer construction, 42-inch wall cabinets, and 65 soft-close doors and drawers — including three glass-front display cabinets that add a touch of elegance. A gas cooking range, stainless appliances, convenient pantry, recessed lighting, casement windows, and a reverse osmosis drinking water system complete a kitchen that is as functional as it is stunning. A sliding door opens directly to the rear deck, making outdoor dining effortless. The sunken family room — with its gas fireplace and French doors — flows seamlessly to a 30x14 rear deck overlooking a wooded backdrop built for every season. Upstairs, the primary suite is a world of its own: trayed ceilings, a private sitting room with a gas fireplace, an intimate morning coffee balcony, and a spa-inspired bath complete with dual vanities, a jetted soaking tub, and a glass walk-in shower. The lower level raises the bar entirely — a 48-foot rec room anchored by a 17-foot horseshoe granite wet bar with Brooklyn loft-style brick wall accents, a full bath, and a dedicated theater room with projector and screen. For peace of mind in 2020 the roof had a major upgrade to 50 Year Long-Life, IKO Dynasty/Cambridge Architectural Shingles and to give additional comfort and security, the heat pumps have been recently replaced; one in 2021 and the other in 2023. Then step outside — and let the land tell its own story. A short walk through your wooded backyard opens up to over an acre of flat, open ground a few steps from the banks of the Conococheague Creek — and what awaits you there is nothing short of remarkable. This is the kind of land that invites you to slow down and build something meaningful. Pitch a tent and wake up to wild flowers and bird songs. Raise a pavilion for family gatherings under the trees. Carve out a meditation space where the sounds are mostly water, wind, and wildlife. Watch deer slip quietly through the tree line. Listen to ducks and geese settle onto the creek at dusk. Spot wild turkey moving through the brush, and squirrels working the canopy overhead. As evening falls, the soundtrack shifts — spring peepers, crickets, tree frogs, and the distant call of an owl fill the air in a way no playlist ever could. Why drive fifty miles for a weekend escape when yours is already waiting, just steps from your back door? Located in the sought-after Greencastle-Antrim School District, minutes to I-81, with recent upgrades throughout. Schedule your private tour today and experience everything this extraordinary home — and its land — has waiting for you.

2384 Castlegreen Drive, Greencastle

Listing courtesy of RE/MAX 1st Advantage. Contact: (717) 591-5555

$639,900

This stunning 5-bedroom, 3 Full bath home is located in a well-established neighborhood with lots of upgrades. The home offers plenty of space with an open floor plan perfect for entertaining, the large windows let in plenty of light. The home was built in 2021 and has all the modern amenities you could want, including a gourmet kitchen with stainless steel appliances a cook's dream! A spacious living room with a cozy fireplace, a main level bedroom and full bathroom, a nice office on the main level with new French doors for privacy when you are working. A finished basement with 2 added rooms, one for storage and the other is currently used as an exercise room. The basement has a walkout and windows adding nice light. A 3-car garage. A nice size deck leading to wonderful stone patio and natural gas firepit. A professionally landscaped yard offering privacy with beautiful wrought iron fencing. This home is perfect for entertaining guests inside and outside. The primary bedroom has its own private bathroom and walk-in closet. This home is move-in ready. Close to schools, parks, and shopping!

5 Beds ⋅ 3 Baths

This stunning 5-bedroom, 3 Full bath home is located in a well-established neighborhood with lots of upgrades. The home offers plenty of space with an open floor plan perfect for entertaining, the large windows let in plenty of light. The home was built in 2021 and has all the modern amenities you could want, including a gourmet kitchen with stainless steel appliances a cook's dream! A spacious living room with a cozy fireplace, a main level bedroom and full bathroom, a nice office on the main level with new French doors for privacy when you are working. A finished basement with 2 added rooms, one for storage and the other is currently used as an exercise room. The basement has a walkout and windows adding nice light. A 3-car garage. A nice size deck leading to wonderful stone patio and natural gas firepit. A professionally landscaped yard offering privacy with beautiful wrought iron fencing. This home is perfect for entertaining guests inside and outside. The primary bedroom has its own private bathroom and walk-in closet. This home is move-in ready. Close to schools, parks, and shopping!

202 Delanie Drive Dr, Greencastle

Listing courtesy of Ronnie Martin Realty, Inc.. Contact:

$650,000

Rare Investment Opportunity: The Castle Motel. This versatile commercial property features 8 motel units plus an attached single-family residence, offering a perfect live-work setup or an additional long-term rental stream. Situated on 1.26 level acres, the property includes a spacious parking lot and a large unfinished basement, rear garage access for ample storage or workshop space. With public sewer connectivity and room for potential expansion, this 1960s landmark is primed for its next chapter.

7967 Molly Pitcher Highway, Greencastle

Listing courtesy of Real Estate Today. Contact:

$699,900

Rare opportunity to own one of the largest and finest brick ranch homes ever offered in Greencastle Greens Golf Course Community. Built in 2002, a local and renowned Toria Build, this one-owner, immaculately maintained home stands in a class of its own; and buyers who have been searching this community know exactly how seldom a home like this comes available. With 3,854 square feet of finished living space above grade and an additional 4,067 square feet of open, walk-out lower level ready to be finished, the total usable footprint reaches 7,921 square feet on 1.66 private, wooded acres. 4 bedrooms, 3 full baths, 1 half bath, 3-car garage with epoxy style floor finish and upgraded doors. The quality of construction is evident from the moment you arrive: full brick exterior, concrete driveway, mature landscaping including Holly, Quickfire and Oak Leaf hydrangeas, Lilac, Crepe Myrtle, Nikko Deutzia, Boxwood, and Soft Serve evergreens framing the approach and flowering through three seasons. Inside: boasts 10-foot and cathedral ceilings, Brazilian cherry hardwood floors, granite countertops, Steve Hollenshead custom cherry cabinetry throughout, two propane fireplaces, Anderson windows, and a Therma-Tru front door. The open kitchen-to-living-room design captures wooded views from every angle. The primary suite features a jetted tub, separate shower, elegant vanity, and two large walk-in closets, complete with custom organizers. An upper-level bedroom with private bath serves equally well as a studio, home office, or exercise room. The 500-sq-ft covered rear veranda; finished in stamped concrete with recessed lighting, T&G ceiling, and rear grill hookup also overlooks a private wooded backdrop. Dual Carrier heat pump systems, (Installed 2015) 5-zone climate control, electric backup heat, private well, and poured concrete walk-out lower level with French doors complete the picture. Greencastle-Antrim School District. I-81 corridor. Reach out today for your private showing!

4 Beds ⋅ 4 Baths

Rare opportunity to own one of the largest and finest brick ranch homes ever offered in Greencastle Greens Golf Course Community. Built in 2002, a local and renowned Toria Build, this one-owner, immaculately maintained home stands in a class of its own; and buyers who have been searching this community know exactly how seldom a home like this comes available. With 3,854 square feet of finished living space above grade and an additional 4,067 square feet of open, walk-out lower level ready to be finished, the total usable footprint reaches 7,921 square feet on 1.66 private, wooded acres. 4 bedrooms, 3 full baths, 1 half bath, 3-car garage with epoxy style floor finish and upgraded doors. The quality of construction is evident from the moment you arrive: full brick exterior, concrete driveway, mature landscaping including Holly, Quickfire and Oak Leaf hydrangeas, Lilac, Crepe Myrtle, Nikko Deutzia, Boxwood, and Soft Serve evergreens framing the approach and flowering through three seasons. Inside: boasts 10-foot and cathedral ceilings, Brazilian cherry hardwood floors, granite countertops, Steve Hollenshead custom cherry cabinetry throughout, two propane fireplaces, Anderson windows, and a Therma-Tru front door. The open kitchen-to-living-room design captures wooded views from every angle. The primary suite features a jetted tub, separate shower, elegant vanity, and two large walk-in closets, complete with custom organizers. An upper-level bedroom with private bath serves equally well as a studio, home office, or exercise room. The 500-sq-ft covered rear veranda; finished in stamped concrete with recessed lighting, T&G ceiling, and rear grill hookup also overlooks a private wooded backdrop. Dual Carrier heat pump systems, (Installed 2015) 5-zone climate control, electric backup heat, private well, and poured concrete walk-out lower level with French doors complete the picture. Greencastle-Antrim School District. I-81 corridor. Reach out today for your private showing!

2368 Castlegreen Drive, Greencastle

Listing courtesy of RE/MAX 1st Advantage. Contact: (717) 591-5555

$685,000

Like-New Rancher on 3 Acres with Mountain & Pastoral Views - Welcome to this stunning, nearly new rancher, just 4 years old and meticulously maintained, this home truly feels like new. Features 3 bedrooms, 2 full baths & 2 half baths. The open floor plan features 9' ceilings and a bright great room with beautiful wood floors and a cozy gas fireplace—perfect for everyday living or entertaining. The eat-in kitchen is a dream, offering granite countertops, a large center island, and all appliances included. Two dining areas provide flexibility for casual meals or formal gatherings. The private primary bedroom suite is a peaceful retreat with a walk-in closet and a stylish en-suite bath featuring a walk-in shower, double vanity, and tile flooring. The second and third bedrooms are thoughtfully located on the opposite side of the home, offering privacy for family or guests. French doors open to a dedicated home office with serene pastoral views—ideal for remote work or a quiet study. Main-level laundry includes washer and dryer for added convenience. Additional highlights include triple garage with workshop space, a walk-up attic heated & cooled and offers abundant storage or potential to convert into additional living space. The finished basement has a spacious family room, second fireplace, half bath, and storage galore. Even the crawl space is insulated and temperature-controlled—no detail overlooked. Nice level lot, large back porch with view of 300+ trees planted for privacy in rear. Peaceful country living with modern comforts, stunning views, and room to grow—this exceptional rancher checks every box. Located 10 min from Greencastle, 7 min to Mercersburg.

3 Beds ⋅ 4 Baths

Like-New Rancher on 3 Acres with Mountain & Pastoral Views - Welcome to this stunning, nearly new rancher, just 4 years old and meticulously maintained, this home truly feels like new. Features 3 bedrooms, 2 full baths & 2 half baths. The open floor plan features 9' ceilings and a bright great room with beautiful wood floors and a cozy gas fireplace—perfect for everyday living or entertaining. The eat-in kitchen is a dream, offering granite countertops, a large center island, and all appliances included. Two dining areas provide flexibility for casual meals or formal gatherings. The private primary bedroom suite is a peaceful retreat with a walk-in closet and a stylish en-suite bath featuring a walk-in shower, double vanity, and tile flooring. The second and third bedrooms are thoughtfully located on the opposite side of the home, offering privacy for family or guests. French doors open to a dedicated home office with serene pastoral views—ideal for remote work or a quiet study. Main-level laundry includes washer and dryer for added convenience. Additional highlights include triple garage with workshop space, a walk-up attic heated & cooled and offers abundant storage or potential to convert into additional living space. The finished basement has a spacious family room, second fireplace, half bath, and storage galore. Even the crawl space is insulated and temperature-controlled—no detail overlooked. Nice level lot, large back porch with view of 300+ trees planted for privacy in rear. Peaceful country living with modern comforts, stunning views, and room to grow—this exceptional rancher checks every box. Located 10 min from Greencastle, 7 min to Mercersburg.

7654 Windmill Road, Greencastle

Listing courtesy of RE/MAX Results. Contact:

$659,900

SEE VIDEO TOUR!!! This is the one you’ve been waiting for. . . the house on the hill that everyone knows! Welcome to this beautiful, custom built, 3 bedroom, 3 bath all brick rancher on 2.55 acres. Approaching the front door, you’ll find all brick steps leading inside to the stately foyer boasting stained trim, crown molding and gorgeous marble flooring. The dining room is adjacent featuring hardwood flooring, chair molding, full height windows, crown molding and tray ceiling. Opposite the foyer is the formal living/sitting room with a continuance of the hardwood floors, full height windows, crown molding and tray ceiling. Don’t miss the pocket doors leading to this room as well as the dining room and dining to kitchen area. Leading from the foyer is the living room where you will find a beautiful natural gas fireplace with marble surround, marble hearth and stained mantle as well as matching stained wainscoting, crown molding and whole house audio system. Adjacent is the kitchen with ample custom cabinetry, Corian peninsula and countertops, double oven, gas cooktop, country sink and a full complement of matching appliances. The crown molding and tray ceilings continue to the kitchen area where a desk/hutch can also be found. Ten-foot ceilings are found throughout these areas. Transitioning from the kitchen is the breakfast nook area with, yes, you guessed it, crown molding and full height windows. The laundry area is found through the nook area as well as a door leading to rear patio and entrance area. Heading back through the kitchen with a quick left turn, takes you to the added great room of over 700 square feet which can only be described as MAJESTIC! You’ll be taken by the gorgeous ceramic flooring, chair molding throughout, walk-out doors to the brick patio area and vaulted ceilings. Family room, game room, theater room, office or all the above? No problem! Back through the living room area and down the hallway, you’ll find a full bath with tub/shower combination. The primary bedroom is the next stop featuring crown molding, marble flooring, a walk-in closet and an additional cedar closet. The adjacent en-suite bath includes a jetted soaking tub, shower stall, linen cabinet, vanity with make-up desk and continuance of the crown molding. At the end of the hall, you will find two additional adequately sized bedrooms. Back through the kitchen and off the nook area is the entrance to the 2-car heated garage as well as stairs to the basement area. Descending the stairs, you will find almost 800 square feet of finished space which includes a sink area as well as an additional full bath. Finally, is the utility/storage area offering 450 square feet of additional space, Bilko walk-out doors to the back yard area, wood stove and a connection to an exterior generator if desired. Combine all of this with well insulated 2x6 construction, air gap, and a 4 inch all brick exterior, custom interior finishes and upgrades to the hilt, curb appeal well beyond the norm and a great location close to I-81 and downtown Greencastle and you may have just found the castle for which you’ve been looking!

3 Beds ⋅ 3 Baths

SEE VIDEO TOUR!!! This is the one you’ve been waiting for. . . the house on the hill that everyone knows! Welcome to this beautiful, custom built, 3 bedroom, 3 bath all brick rancher on 2.55 acres. Approaching the front door, you’ll find all brick steps leading inside to the stately foyer boasting stained trim, crown molding and gorgeous marble flooring. The dining room is adjacent featuring hardwood flooring, chair molding, full height windows, crown molding and tray ceiling. Opposite the foyer is the formal living/sitting room with a continuance of the hardwood floors, full height windows, crown molding and tray ceiling. Don’t miss the pocket doors leading to this room as well as the dining room and dining to kitchen area. Leading from the foyer is the living room where you will find a beautiful natural gas fireplace with marble surround, marble hearth and stained mantle as well as matching stained wainscoting, crown molding and whole house audio system. Adjacent is the kitchen with ample custom cabinetry, Corian peninsula and countertops, double oven, gas cooktop, country sink and a full complement of matching appliances. The crown molding and tray ceilings continue to the kitchen area where a desk/hutch can also be found. Ten-foot ceilings are found throughout these areas. Transitioning from the kitchen is the breakfast nook area with, yes, you guessed it, crown molding and full height windows. The laundry area is found through the nook area as well as a door leading to rear patio and entrance area. Heading back through the kitchen with a quick left turn, takes you to the added great room of over 700 square feet which can only be described as MAJESTIC! You’ll be taken by the gorgeous ceramic flooring, chair molding throughout, walk-out doors to the brick patio area and vaulted ceilings. Family room, game room, theater room, office or all the above? No problem! Back through the living room area and down the hallway, you’ll find a full bath with tub/shower combination. The primary bedroom is the next stop featuring crown molding, marble flooring, a walk-in closet and an additional cedar closet. The adjacent en-suite bath includes a jetted soaking tub, shower stall, linen cabinet, vanity with make-up desk and continuance of the crown molding. At the end of the hall, you will find two additional adequately sized bedrooms. Back through the kitchen and off the nook area is the entrance to the 2-car heated garage as well as stairs to the basement area. Descending the stairs, you will find almost 800 square feet of finished space which includes a sink area as well as an additional full bath. Finally, is the utility/storage area offering 450 square feet of additional space, Bilko walk-out doors to the back yard area, wood stove and a connection to an exterior generator if desired. Combine all of this with well insulated 2x6 construction, air gap, and a 4 inch all brick exterior, custom interior finishes and upgrades to the hilt, curb appeal well beyond the norm and a great location close to I-81 and downtown Greencastle and you may have just found the castle for which you’ve been looking!

1015 Buchanan Trail East, Greencastle

Listing courtesy of Coldwell Banker Realty. Contact:

$619,900

Experience the beauty of this property - inside & outside. Tranquil & Peaceful Wooded Setting in Greencastle Greens! Home with main level primary & upper level primary plus finished walk-out-to grade lower level - multiple living options for you! So, let's start with describing the chance to have your own wooded backdrop, paths to walk in the woods, a deck & a patio to sit out & enjoy your mornings & evenings. A beautiful fenced in-ground pool installed by Flohr Pools & serviced consistently two times a year to open & close with new filter & heater within the past 2-3 years. Plus, a cabana for quiet times or entertaining times. This is a beautiful custom-built 5BR/4.5BA with close to 4400 finished SF home located on a cul de sac in Greencastle Greens. Walking into the foyer, you will find a room for everyone in this home with abundant windows & beautiful views. Starting with the main floor, a cozy office w/built-in bookcases, large dining rm, kitchen w/stainless steel appliances, breakfast nook, family rm w/gas fireplace w/french doors to the deck. Also located on the main level is a primary suite plus main level laundry area. The upper level has three generous-sized bedrooms w/hall bath & a huge second primary suite. Main & upper level w/hardwood floors throughout. The lower level which could be used as an in-law suite or great entertaining space has a small kitchenette, full bath, large living area w/French doors leads to the brick patio & pool area. In addition, you have the utility rm, storage area, plus an additional laundry hook up & hallway to the oversized two-car garage. Exterior with electric dog fence to keep your puppies at home. This home has been well-maintained with only one owner. Plan your visit today to see your future wooded retreat with private space in the Greens! Seller is motivated! Pool opening May 22 and Power washing May 23.

5 Beds ⋅ 5 Baths

Experience the beauty of this property - inside & outside. Tranquil & Peaceful Wooded Setting in Greencastle Greens! Home with main level primary & upper level primary plus finished walk-out-to grade lower level - multiple living options for you! So, let's start with describing the chance to have your own wooded backdrop, paths to walk in the woods, a deck & a patio to sit out & enjoy your mornings & evenings. A beautiful fenced in-ground pool installed by Flohr Pools & serviced consistently two times a year to open & close with new filter & heater within the past 2-3 years. Plus, a cabana for quiet times or entertaining times. This is a beautiful custom-built 5BR/4.5BA with close to 4400 finished SF home located on a cul de sac in Greencastle Greens. Walking into the foyer, you will find a room for everyone in this home with abundant windows & beautiful views. Starting with the main floor, a cozy office w/built-in bookcases, large dining rm, kitchen w/stainless steel appliances, breakfast nook, family rm w/gas fireplace w/french doors to the deck. Also located on the main level is a primary suite plus main level laundry area. The upper level has three generous-sized bedrooms w/hall bath & a huge second primary suite. Main & upper level w/hardwood floors throughout. The lower level which could be used as an in-law suite or great entertaining space has a small kitchenette, full bath, large living area w/French doors leads to the brick patio & pool area. In addition, you have the utility rm, storage area, plus an additional laundry hook up & hallway to the oversized two-car garage. Exterior with electric dog fence to keep your puppies at home. This home has been well-maintained with only one owner. Plan your visit today to see your future wooded retreat with private space in the Greens! Seller is motivated! Pool opening May 22 and Power washing May 23.

8140 Golf Vista Dr, Greencastle

Listing courtesy of Coldwell Banker Realty. Contact: