Homes for Sale near Shady Side Academy

• 

  

  

  /31

  $240,000

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  8952 Eastwood Rd, Pittsburgh, PA 15235

  Reimagined Penn Hills craftsman delivers space, style, and updates from top to bottom. Set on tree-lined Eastwood Road—where stately homes and mature trees create a picturesque backdrop—this three-bed, two-bath stunner is deceptively spacious and move-in ready. A shady front porch introduces a proper entry foyer with original trim, flowing into airy, open-concept living and dining rooms with

  Emily Fraser PIATT SOTHEBY'S INTERNATIONAL REALTY

  

  8952 Eastwood Rd, Pittsburgh, PA 15235
• 

  

  

  /50

  $699,900

  • 7 Beds
  • 5.5 Baths
  • 4,638 Sq Ft

  630 N Negley Ave, Pittsburgh, PA 15206

  This stately colonial, a grand brick masterpiece spanning over two stories, exudes old-school charm & timeless elegance. The current zoning is RM-M. Single family to multi units are permitted. Boasting stunning woodwork throughout, including exquisite stained-glass windows, pocket doors, a large formal entry, the home is a true testament to craftsmanship. Some bedrooms are rented to mo-to mo

  Susan Kaczorek RE/MAX SELECT REALTY

  

  630 N Negley Ave, Pittsburgh, PA 15206
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  /38

  $1,150,000

  • 5 Beds
  • 4.5 Baths
  • 3,475 Sq Ft

  17 Carolina Ave, Oakmont, PA 15139

  Experience low-maintenance luxury in the sought-after River’s Edge community of Oakmont. This 5-bedroom, 4.1-bath home offers high ceilings, hardwood floors, and a chef’s kitchen that anchors the open, light-filled living space. The first-floor primary suite provides convenient single-level living, while additional bedrooms and baths across the upper levels offer flexibility for guests,

  Tyler Petit RE/MAX SELECT REALTY

  

  17 Carolina Ave, Oakmont, PA 15139
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  /38

  $259,900

  • 3 Beds
  • 1.5 Baths

  601 Dressel Rd, Allison Park, PA 15101

  Welcome to this All Brick 3-bedroom, 1.5-bath Ranch nestled in The heart of the desirable Stoneridge plan! Dressel Rd is located minutes from major roadways, schools, parks, shopping and dining. The home features an inviting one-level layout with beautiful hardwood floors, perfect for everyday living and entertaining. Large Eat-in Kitchen, Master bed complete with a half bath, plenty of closet

  Jason Rakers RE/MAX SELECT REALTY

  

  601 Dressel Rd, Allison Park, PA 15101
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  /42

  $1,595,000 Open Sun 12PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 3,045 Sq Ft

  54 1st St, Oakmont, PA 15139

  Live at the best waterfront location in Pittsburgh, The River’s Edge of Oakmont! This elegant Brownstone offers luxury living in one of Pittsburgh’s most desirable communities. Nestled along the scenic Allegheny River, The River’s Edge combines timeless architecture w/modern amenities. The Brownstones stand out with distinctive brick & stone exteriors. Inside you'll find a private in-home

  Deborah Donahue-Kane HOWARD HANNA REAL ESTATE SERVICES

  

  54 1st St, Oakmont, PA 15139
• 

  

  /50

  $254,900

  • 3 Beds
  • 2 Baths

  7872 Mount Carmel Rd, Verona, PA 15147

  Welcome to your dream home in Penn Hills! Perfectly positioned on a spacious corner lot, this home has been beautifully renovated. Step into the cozy living room with a stone wood burning fireplace. Off the living room, the dining area flows into an updated kitchen with sleek appliances & a delightful balcony. Down the hall, you'll find two well-sized bedrooms & a thoughtfully updated bathroom.

  Anjelica Macioce RE/MAX SELECT REALTY

  

  7872 Mount Carmel Rd, Verona, PA 15147
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  /27

  $179,000

  • 3 Beds
  • 1 Bath
  • 1,125 Sq Ft

  819 8th St, Verona, PA 15147

  Welcome to 819 8th Street in Verona, a charming and cozy home featuring 3 bedrooms, one full bath, and a lovely rear deck. The main level includes a nice sized living room with a wood-burning fireplace, dining room, kitchen w/additional corner storage. A full bath and a conveniently located main-level bedroom add to the home’s ease and functionality. Upstairs, you’ll find two additional bedrooms

  Joe Weltner COLDWELL BANKER REALTY

  

  819 8th St, Verona, PA 15147
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  /50

  $639,000

  • 4 Beds
  • 3 Baths
  • 2,840 Sq Ft

  107 Cove Run Aka 60 Candy Hollow, Indiana Township, PA 15024

  SITUATED ON OVER 7 ACRES IN FOX CHAPEL SCHOOL DISTRICT, THIS WONDERFUL HOME OFFERS NUMEROUS AMMENITIES & CLASSIC STYLING! LARGE FRONT PORCH WITH COLUMNS LEAD INTO A SPACIOUS LIVING ROOM ,1ST FLOOR DEN WITH BUILT IN BOOK CASES PLUS A FULL BATH. A FORMAL DINING ROOM THAT HAS HARDWOOD FLOORS & WALK OUT BAY WINDOW. EQUIPPED KITCHEN WITH CENTER ISLAND OPENS TO PANTRY WITH WASHER/DRYER AND OPENS TO A

  Gregory Higbee BERKSHIRE HATHAWAY THE PREFERRED REALTY

  

  107 Cove Run Aka 60 Candy Hollow, Indiana Township, PA 15024
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  /2

  $159,900

  • Land
  • 0.08 Acre
  • $1,998,750 per Acre

  675 (Lot 132) Arbor Ct, O'Hara Township, PA 15238

  New construction in O'Hara Township in Fox Chapel School District. Design and build your custom floor plan. Chapel Harbor at the Water is a riverfront community very close to the Waterworks shopping plaza and Fox Chapel Yacht Club. Easy access to route 28 and a short drive from downtown Pittsburgh. HOA takes care of snow removal from main roads and alleys as well as lawn maintenance and mulching.

  Kathryn Heinauer KELLER WILLIAMS STEEL CITY

  

  675 (Lot 132) Arbor Ct, O'Hara Township, PA 15238
• 

  

  /12

  $375,000

  • Land
  • 1 Acre
  • $375,000 per Acre

  329 Dorseyville, O'Hara, PA 15215

  Build Your Dream Home at Meinert Estates – A Rare Opportunity in the Fox Chapel School District. Welcome to Meinert Estates, a premier new subdivision that offers the perfect setting to bring your dream home to life. Tucked away in a peaceful, natural environment, yet conveniently located. Enjoy the serenity of parks, streams, and scenic trails right nearby, offering endless opportunities for

  Vicky Chang COLDWELL BANKER REALTY

  

  329 Dorseyville, O'Hara, PA 15215
• 

  

  /23

  $940,000

  621-623 Lincoln Ave, Pittsburgh, PA 15206

  Welcome to this a rare opportunity to own a 7-unit apartment building offering the perfect blend of convenience, style, comfort, and affordability. Each spacious unit features updated finishes, modern appliances, and access to outdoor space—ideal for tenants seeking style and functionality. Off-street parking ensures hassle-free living, while separate utilities empower residents to manage energy

  Jeannine Dabecco COLDWELL BANKER REALTY

  

  621-623 Lincoln Ave, Pittsburgh, PA 15206
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  /29

  $1,995,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,703 Sq Ft

  Lot 1 Cascades Way, O'Hara Township, PA 15215

  The Hither Hills blends refined Modern European style with function and charm in The Cascades, an exclusive community in the Fox Chapel School District. Dramatic rooflines and natural wood accents create standout curb appeal. Inside, enjoy an elegant great room with tray ceiling, vaulted kitchen and dining with exposed beams, and a signature arched window. A walk-in pantry and dedicated coffee

  David Onufer HOWARD HANNA REAL ESTATE SERVICES

  

  Lot 1 Cascades Way, O'Hara Township, PA 15215
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  /45

  $1,150,000

  • 4 Beds
  • 5 Baths
  • 3,300 Sq Ft

  112 Wynnwood Dr, Pittsburgh, PA 15215

  Secluded contemporary situated in a private natural setting with amenities to make this your private retreat. The greenhouse attached to the garage provides for year-round greenery, giving you the ability to make this home a truly special home for you and your family. Built to maximize the natural light with views of the woods and Camp Guyasuta from two sides of the home. A large office has

  Amanda Cullen COLDWELL BANKER REALTY

  

  112 Wynnwood Dr, Pittsburgh, PA 15215
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  /28

  $100,000

  • 3 Beds
  • 1 Bath
  • 1,122 Sq Ft

  8325 Bricelyn St, Pittsburgh, PA 15221

  This approximately 1,500 square foot house offers three bedrooms, and one bathroom located in East Hills. The living room features access to an enclosed front porch. The kitchen has ample cabinetry and complemented by the adjacent dining area. The three bedrooms offer comfortable accommodation, with the primary bedroom being a versatile space that could serve a variety of needs. The property

  Monica Reynolds COLDWELL BANKER REALTY

  

  8325 Bricelyn St, Pittsburgh, PA 15221
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  /28

  $239,900

  • 4 Beds
  • 2 Baths
  • 1,313 Sq Ft

  1954 Outlook Dr, Verona, PA 15147

  4 Bedroom Cape Cod on a level usable lot in PRISTINE condition. Perfect for those that may need a First Floor Primary Suite .Has 2 Bedrooms and a bath of First floor and 2 bedrooms and a bath on 2nd floor. Large Spacious Living room, eat in Dining area and Updated Kitchen Appliances. Much larger home than it looks from the street. Great neighborhood of similar homes and area. Very close to

  Joe Larkin HOWARD HANNA REAL ESTATE SERVICES

  

  1954 Outlook Dr, Verona, PA 15147
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  /27

  $335,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,978 Sq Ft

  710 Spencer Woods Dr, Glenshaw, PA 15116

  Must-see opportunity in the highly desirable Spencer Woods Community! Pride of ownership shines throughout this meticulously maintained patio home, offered by its original owner.A soaring cathedral ceiling and cozy fireplace create a welcoming focal point in the spacious living room. The open kitchen and dining area offer excellent flow—ideal for everyday living and entertaining.The first-floor

  Nancy Snider COLDWELL BANKER REALTY

  

  710 Spencer Woods Dr, Glenshaw, PA 15116
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  /32

  $149,900

  • 3 Beds
  • 1.5 Baths
  • 1,612 Sq Ft

  104 Rivermont Ct, Cheswick, PA 15024

  Move in ready 3 bedroom 1.5 bath condominium in The Highlands Woods community of Cheswick. Enjoy the perfect blend of comfort, convenience & low maintenance living. Step inside to find newer stainless steel appliances in the kitchen. This open-concept layout featuring new flooring throughout this condo of approximately 1612 Sq ft provides plenty of easy living space. Elevated dining area with 1st

  Jan Jursa COLDWELL BANKER REALTY

  

  104 Rivermont Ct, Cheswick, PA 15024
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  /25

  $4,770,000

  • 4 Beds
  • 6 Baths

  Walden the Oberoi Fox Chapel, Fox Chapel, PA 15238

  Introducing The Oberoi—Fox Chapel’s last great estate opportunity. Set on approximately 5 acres of untouched woodland in one of Pittsburgh’s most prestigious communities, this rare property offers unparalleled privacy and the chance to create a lasting legacy. Nestled within this extraordinary setting, Walden is a modern cottage-inspired residence blending timeless elegance with contemporary

  David Onufer HOWARD HANNA REAL ESTATE SERVICES

  

  Walden the Oberoi Fox Chapel, Fox Chapel, PA 15238
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  /14

  $550,000

  628 Haverhill St, Pittsburgh, PA 15208

  Huge Development Opportunity in Homewood-Brushton!! Duplex situated on 1 Acre! 175 Ft of Frontage! Various strategies here: 1. Subdivide and sell off the lots, 2. Renovate the Duplex to live in, hold, or sell, and keep the land, 3. Teardown the duplex and build multiple houses on Haverhill. 4. A combination of these 3 strategies. In either case- multiple buildings could be built on this parcel.

  Ryan Shedlock HOWARD HANNA REAL ESTATE SERVICES

  

  628 Haverhill St, Pittsburgh, PA 15208
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  /18

  $25,000

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft

  6983 Lemington Ave, Pittsburgh, PA 15206

  Don't miss this opportunity to invest in a neighborhood experiencing significant revitalization and growth. Bring your contractor, your vision, and prepare to unlock the full potential. Easy access to Penn Ave, Butler st, East Liberty, and Bloomfield. Full renovation required.

  Jason Zalin REALTY CO LLC

  

  6983 Lemington Ave, Pittsburgh, PA 15206
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  /33

  $300,000

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  6319 Stanton Ave, Pittsburgh, PA 15206

  This delightful 3-bedroom, 1-bath rowhouse is a perfect blend of classic style and modern convenience in a highly sought-after area. Step inside to a home filled with natural light, featuring nicely sized rooms for comfortable living. Floors have been refinished throughout. The kitchen has been updated to include newer appliances, neutral quartz countertops and lots of storage space. Enjoy your

  Sara Leitera BERKSHIRE HATHAWAY THE PREFERRED REALTY

  

  6319 Stanton Ave, Pittsburgh, PA 15206
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  /6

  $4,950,000 New Construction

  • 5 Beds
  • 6 Baths
  • 7,849 Sq Ft

  280 Glen Laurel Ln, Pittsburgh, PA 15238

  Welcome to your dream home opportunity nestled on a premier 3-acre lot. This custom residence offers an unparalleled chance to fully customize your ideal living space amidst breathtaking natural surroundings. Collaborate with Wade Weissman Architecture and Phillip Wentzel Custom Homes, where the fusion of innovative design and masterful craftsmanship brings your vision to life. With a site ready

  Meredith Ward HOWARD HANNA REAL ESTATE SERVICES

  

  280 Glen Laurel Ln, Pittsburgh, PA 15238
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  /44

  $699,000

  • 4 Beds
  • 3 Baths
  • 1,940 Sq Ft

  101 Buckingham Rd, Pittsburgh, PA 15215

  Sophisticated single-level living in sought-after close-in Fox Chapel. This beautifully updated ranch offers effortless elegance with three bedrooms and two full baths on the main level, including a fully accessible suite with roll-in shower. The expansive kitchen, featuring new premium appliances, island cooktop, and telescoping exhaust fan, flows seamlessly for entertaining. The lower level

  David Onufer HOWARD HANNA REAL ESTATE SERVICES

  

  101 Buckingham Rd, Pittsburgh, PA 15215
• 

  

  /22

  $179,900

  412 Short Canal St, Pittsburgh, PA 15215

  Investment opportunity in the heart of Sharpsburg! This up/down duplex is perfect to add to your blossoming rental portfolio or as an owner occupied house hack. Gas and electric are separated. Two separate furnaces and two water heaters. Shared basement with laundry hook ups. All the appliances stay. Fenced in side yard perfect for parties. Upstairs is 2 bedrooms (with an additional captive 3rd

  Adam Gleve DEACON & HOOVER REAL ESTATE ADVISORS LLC

  

  412 Short Canal St, Pittsburgh, PA 15215
• 

  

  /27

  $495,000

  5423 Wellesley Ave, Pittsburgh, PA 15206

  Pretty darn turn key opportunity for investment purposes in the desirable Morningside neighborhood! Located on a quiet street with new roof, and a complete interior cosmetic renovation, this place should provide years of worry free income potential! The upper unit offers four bedrooms, and two baths! imagine how fast this will fill up with students if that's the route you choose! A great covered

  Chad Church KELLER WILLIAMS REALTY

  

  5423 Wellesley Ave, Pittsburgh, PA 15206
• 

  

  /35

  $515,000

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  305 Butternut Ct, Pittsburgh, PA 15238

  If spacious, low-maintenance, cul-de-sac living is on your must-have list, then hurry in to see 305 Butternut Court! Located in the Forest Manor Neighborhood, this sun-drenched brick townhome is brimming with updates. Parquet wood floors usher you in to the first floor which boasts fully equipped kitchen/granite countertops, dining room, living room, 1/2 bath & family room with gas fireplace.

  Suzanne Spears REALTY ONE GROUP GOLD STANDARD

  

  305 Butternut Ct, Pittsburgh, PA 15238
• 

  

  /35

  $539,000

  • 3 Beds
  • 2.5 Baths
  • 1,812 Sq Ft

  102 Alleyne Dr, Pittsburgh, PA 15215

  Full of natural light and surrounded by a beautiful, tree-lined backyard, this 3 bedroom, 2.5 bath home feels warm, welcoming, & spacious! Step into the bright living & dining rooms, where large, beautiful windows invite the sunlight in & give a bright & cheerful feeling. The kitchen features a stunning full-length window with views of the trees & is the perfect place to gather, cook, and enjoy

  Molly Finley HOWARD HANNA REAL ESTATE SERVICES

  

  102 Alleyne Dr, Pittsburgh, PA 15215
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  /50

  $809,000

  • 3 Beds
  • 3.5 Baths

  100 Denniston St Unit 40, Pittsburgh, PA 15206

  Beautiful end-unit townhouse. Meticulously renovated with premium finishes. Bathed in light from a southern exposure. Warmed by Brazilian rosewood floors. Remodeled kitchen with granite, custom cabinetry & high-end appliances. Renovated powder room & deck on main level. Upstairs are 3 bedrooms and 3 baths. 2 are suites with updated baths and walk-in closets. One has vaulted ceilings, beautiful

  Michael Toretti RE/MAX SELECT REALTY

  

  100 Denniston St Unit 40, Pittsburgh, PA 15206
• 

  

  /19

  $22,500

  • 3 Beds
  • 1 Bath
  • 900 Sq Ft

  1114 N Wheeler St, Pittsburgh, PA 15208

  Investment opportunity at 1114 Wheeler St, PGH 15208! Solid 3BD/1BA home, approx 900 sqft on a manageable lot. Perfect for investors looking for a value-add project. Home needs general cosmetics & mechanical updates—ideal chance to customize & build equity. Efficient layout w/ 3 beds. Quick access to major routes, public transit, parks & local shops. Urban convenience, walkable blocks & strong

  Tina Nobers JANUS REALTY ADVISORS

  

  1114 N Wheeler St, Pittsburgh, PA 15208
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  /14

  $198,000

  • Land
  • 1.11 Acres
  • $179,024 per Acre

  104 Chapel Crest Terrace, Pittsburgh, PA 15238

  Tucked in the woods of the Fox Chapel School District, bring your own builder to create your perfect home. Situated on a sleepy street of unique builds, you can take advantage of two portions of frontage on Chapel Crest - either atop the slope near the head of the street, or around the bend for a more private entry drive. Nestled in the heart of the Fox Chapel School District with a short drive

  Amanda Troup COLDWELL BANKER REALTY

  

  104 Chapel Crest Terrace, Pittsburgh, PA 15238
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  /17

  $99,000

  • Land
  • 0.05 Acre
  • $2,156,863 per Acre

  520 Kendall St, Pittsburgh, PA 15201

  Prime Upper Lawrenceville Lot with City Views – A Rare Opportunity! Build your dream home!Nestled on a quiet street in one of Pittsburgh’s hottest neighborhoods, this Upper Lawrenceville lot is a hidden gem waiting for your next big project. Just three blocks from the vibrant energy of Butler Street—home to acclaimed restaurants, pubs, and coffee shops—you’ll enjoy the perfect blend of

  Ed Noschese RE/MAX HOME CENTER

  

  520 Kendall St, Pittsburgh, PA 15201
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  /36

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft

  6333 Glenview Place, Pittsburgh, PA 15206

  Character & Charm describe this row house located in such a key spot in the heart of Highland Park! Natural sunlight flows in through the windows making it bright and cheerful throughout. The interior has been freshly repainted with brand new carpet. The front porch invites you into a lovely living room with a decorative fireplace and a spacious dining room leading into a cozy kitchen. From the

  Priscilla Bromley HOWARD HANNA REAL ESTATE SERVICES

  

  6333 Glenview Place, Pittsburgh, PA 15206
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  /39

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,973 Sq Ft

  169 Woodshire Dr, Pittsburgh, PA 15215

  Welcome to this timeless stone home, filled with character, craftsmanship, and warm natural light throughout. Set on a level yard, this property welcomes you with a classic stone facade and an inviting Mediterranean- inspired elegance. Inside, you'll find beautiful tile, adding artistry and charm to the space. Refined marble accents and wrought iron railings enhance the home's architectural

  Gina Gruden HOWARD HANNA REAL ESTATE SERVICES

  

  169 Woodshire Dr, Pittsburgh, PA 15215
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  /26

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,152 Sq Ft

  5923 Bryant St, Pittsburgh, PA 15206

  Welcome Home! This lovely brick home is situated in the heart of Highland Park's thriving Bryant Street business district. The home has a neutral decor throughout. The updated kitchen is fully equipped with stainless steel appliances, both the full bath and 1/2 bath are updated the covered front porch and fenced in meticulously maintaind back yard is a perfect respite for summer and fall

  Lee Harris COLDWELL BANKER REALTY

  

  5923 Bryant St, Pittsburgh, PA 15206
• 

  

  /8

  $329,000

  • 3 Beds
  • 2.5 Baths
  • 2,032 Sq Ft

  5404 Black St, Pittsburgh, PA 15206

  This enormous 3 story single family residence is conveniently located near local shopping, public transit, and offers easy access to anywhere in the city. 5 minutes from Whole Foods, Target, Home Depot, local restaurants, coffee shops, and charming Lawrenceville. This is an absolute stunner!!! The original woodwork provides old world charm of pocket doors, tray ceilings, decorative fireplaces,

  Blake McNeely KELLER WILLIAMS EXCLUSIVE

  

  5404 Black St, Pittsburgh, PA 15206
• 

  

  /16

  $125,000

  • 3 Beds
  • 1 Bath
  • 1,841 Sq Ft

  5308 Verona Rd, Verona, PA 15147

  Welcome to 5308 Verona Rd—a cozy home with a great layout and plenty of natural light throughout. The main level offers a comfortable living space that flows nicely into the kitchen and dining area. There are two full bedrooms on this level, as well as a full bath! The property also features space for a usable yard perfect for outdoor seating, pets, or gardening. This home is ready for you to add

  Shane Smith COLDWELL BANKER REALTY

  

  5308 Verona Rd, Verona, PA 15147
• 

  

  /29

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 1,883 Sq Ft

  1260 Fox Chapel Rd, Pittsburgh, PA 15238

  Private setting

  Harold Sankey FOX CHAPEL REAL ESTATE INC.

  

  1260 Fox Chapel Rd, Pittsburgh, PA 15238
• 

  

  /37

  $144,900

  2402 Laketon Rd, Pittsburgh, PA 15221

  Seasoned investors will tell you to buy an easy to maintain brick box. 2400-2402 Laketon is exactly that. Throw in all utilities are separated and paid by the tenants, the units are large 3 bedrooms, each has some nice outdoor space, parking, storage and laundry hook ups. This one checks all the boxes and once managed up, it will kick off some nice cash flow. The location is prime. Close to the

  Richard Brown NEXTHOME PPM REALTY

  

  2402 Laketon Rd, Pittsburgh, PA 15221
• 

  /2

  $85,000

  • 3 Beds
  • 1 Bath
  • 1,676 Sq Ft

  1812 Maplewood Ave, Pittsburgh, PA 15221

  Dante Egizio RE/MAX SELECT REALTY

  

  1812 Maplewood Ave, Pittsburgh, PA 15221
• 

  

  /42

  $349,000

  • 3 Beds
  • 2.5 Baths
  • 1,975 Sq Ft

  213 18th St, Pittsburgh, PA 15215

  This well-maintained home sits on a rare double lot in the Fox Chapel School District, offering plenty of space both inside and out. The main level features an open kitchen that connects to a spacious dining room, with easy access to a large outdoor area—ideal for everyday living or hosting guests. Two light filled bedrooms upstairs and full bath with large walk-in closet in hallway. Downstairs,

  Trudy Ward HOWARD HANNA REAL ESTATE SERVICES

  

  213 18th St, Pittsburgh, PA 15215

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