Cumberland Homes with Pool

Cumberland Homes with Pool

Welcome to Cumberland, Maryland, a charming city nestled in the picturesque Allegany County. Known for its rich history and vibrant community, Cumberland offers a unique blend of small-town charm and modern amenities. Surrounded by the stunning Appalachian Mountains, this city is an outdoor enthusiast's paradise, boasting a plethora of hiking trails, parks, and scenic views that will take your breath away.

Cumberland's downtown area is a delightful mix of historical architecture and contemporary shops, cafes, and restaurants. Stroll along the bustling streets, where you can find art galleries showcasing local talent, and enjoy the rich cultural scene that includes music festivals and community events throughout the year. The city’s rich heritage is reflected in its well-preserved buildings and landmarks, making it a perfect place for history buffs.

For those seeking a home that offers a touch of luxury, Cumberland features an array of stunning properties with pools. Imagine coming home to your own oasis, where you can unwind and relax in your private retreat. These homes not only provide a refreshing escape during the warm summer months but also create an ideal setting for entertaining friends and family. Whether you prefer a cozy backyard pool or a sprawling outdoor space, Cumberland has something for everyone.

With its welcoming atmosphere, access to nature, and beautiful homes with pools, Cumberland is not just a place to live; it's a place to thrive. Discover your dream home in this hidden gem of Maryland and experience the perfect blend of comfort and adventure!

Newest Cumberland Homes with Pool

$275,000
3 Beds ⋅ 2 Baths
NESTLED IN A PRIME SOUGHT-AFTER NEIGHBORHOOD - THIS 3 BDRM - 2 BATH HOME FEATURES A BEAUTIFUL IN-GROUND POOL - VAULTED CEILINGS AND AN ELEGANT GAS FIREPLACE IN THE FAMILY ROOM - THE OVER 1/2 ACRE LANDSCAPED LOT PROVIDES PRIVACY AND PLENTY OF OUTSIDE RECREATIONAL FUN - THE STUNNING POOL AREA HAS A COVERED POOLSIDE PATIO PERFECT FOR RELAXING - THE PLENTIFUL POOL DECKING AREA ALSO PROVIDES LOTS OF ROOM FOR TABLES - CHAIRS AND SUNBATHING (THE SELLER IS OFFERING $10,000 TOWARDS UPDATES TO THE DECKING ON THE SWIMMING POOL) THIS HOME HAS MANY UPDATES INCLUDING A NEWER ROOF - HVAC AND LANDSCAPING - LOCATED IN A VERY LOW TRAFFIC AREA - OUTSIDE OF CITY LIMITS - LOWER TAXES

11909 Mulberry Ave, Cumberland

Listing courtesy of Century 21 Potomac West. Contact:

$40,000
This large duplex property is a wonderful opportunity for any investor with a vision. It has a very strong resale potential. The house needs a complete reno and is perfect for a flip or rebuild-and-sell strategy. Enter at own risk.

516 Shriver Ave, Cumberland

Listing courtesy of Perry Wellington Realty, LLC. Contact: 2409794660
$399,900
4 Beds ⋅ 3 Baths
Welcome to 935 Dingle Park Drive! This stunning mid-century home has been lovingly maintained by the same family since it was was built in 1966. It offers a truly unique setting at the end of a quiet West Side street, surrounded by mature woods offering exceptional privacy and peaceful views. The main level features a spacious foyer, formal living and dining rooms, a large kitchen with abundant counter space and a breakfast area, and a cozy den with custom built-ins, including a record player, and expansive picture windows overlooking the woods. The private bedroom wing includes a spacious primary suite with wooded views, a large walk-in closet/dressing area, and an en-suite bath, along with a second bedroom and a full hall bath. The fully finished walk-out lower level offers two additional bedrooms, a third full bath, a family room with a wood-burning fireplace and wet bar, an office area, laundry room, and ample storage. Both floors offer approx. 4,300 finished square feet! Outside, enjoy a patio that leads to the in-ground pool, which has not been operational for approximately 10 years. The sellers are offering a $10,000 credit that can be used toward filling in the pool or restoring it, and an outdoor storage room provides space for pool equipment. Completing the property is a spacious two-car attached garage and circular driveway. New roof, soffit, gutters in 2024. Call today- this home is a rare combination of timeless mid-century character, generous living space, and a serene natural setting just MINUTES away from Downtown Cumberland and I-68.

935 Dingle Park Dr, Cumberland

Listing courtesy of Mountainside Home Realty. Contact: 3017220190
$575,000
4 Beds ⋅ 4 Baths
Prepare to be impressed by this spectacular 4-bedroom, 3.5-bath custom home where timeless elegance meets exceptional comfort. From the moment you step into the grand foyer, you'll appreciate the impressive scale, refined finishes, and thoughtfully designed floor plan that make this home truly unforgettable. Designed for both everyday living and grand entertaining, the main level features an expansive family room, an elegant formal living room, and an oversized dining room perfect for hosting family and friends. At the heart of the home, the stunning chef's kitchen is both beautiful and functional, opening seamlessly to the sun-filled breakfast room and inviting sunroom—perfect for morning coffee or quiet evenings overlooking the backyard. Everyday living is effortless with a main-level laundry room, an oversized mudroom, and convenient access to the attached two-car garage. Upstairs, escape to the luxurious primary suite, a private retreat offering generous space to unwind, while three additional bedrooms and a dedicated upper-level study provide flexibility for today's lifestyle. The finished walk-out lower level is an entertainer's dream, offering abundant recreation space along with a charming wine cellar that's sure to impress guests. Outside, your own private resort awaits. Relax on expansive decks, entertain on the patio, or spend summer days enjoying the sparkling in-ground pool, all surrounded by a beautifully fenced yard offering privacy and room to roam. From grand entertaining to everyday living, every space has been designed with comfort, style, and functionality in mind. This extraordinary property delivers the space, amenities, and lifestyle you've been searching for—a place you'll be proud to call home.

1022 Cherrywood Ave, Cumberland

Listing courtesy of Coldwell Banker Premier. Contact: (301) 777-3380
$309,300
4 Beds ⋅ 3 Baths
The Dingle--Cumberland's premier development began just after the Roaring '20's and was the replacement for the Victorian home styles. The syles of the homes blended the fine workmanship of the times pre-depression where the homes were opulant and massive in size to a more compact home still complete with the elegance of the era and some of the finest workmanship available. This quaint neighborhood itself is small and at one time was likely one of the first gated communties. You can still see where the gates were located--but, even without the gate, it still offers a sense of privacy with only one way in and out. All names of the streets, Buckingham, Dingle, Windsor, Piccadily reflect british aristocracy and, for a little trivia also names for men's shirt styles in that era--that darned Google! It is located at the cross roads of 220 S and I 68 E and West within a few minutes and a stone's throw to the Great Allegheny Bike Passage and downtown arts and entertainment section. To go on, this is a home that blends the style and structure of a home from the 1930's home, only updated to todays modern needs....well worth a look!

833 Buckingham Rd, Cumberland

Listing courtesy of Perry Wellington Realty, LLC. Contact: 2409794660
$449,900
4 Beds ⋅ 3 Baths
Welcome to 325 Francis Court! Offering more than 2,900 square feet of living space, this beautifully maintained home also includes a basement with excellent potential for additional finished square footage. The main level features a welcoming foyer, formal living room, formal dining room, a spacious kitchen with abundant counter space and a bright breakfast area, a family room, a convenient half bath, and a laundry room. Upstairs, you'll find a spacious primary suite with a private bathroom and walk-in closet, along with three additional bedrooms and a full hall bathroom. The partially finished basement provides additional flexibility with a finished room and ample unfinished space ready to be customized to fit your needs. Outside, enjoy a private backyard that backs to woods and features a fully fenced yard, above-ground pool, and hot tub—perfect for relaxing or entertaining. Recent updates include a new AC unit in 2023, a new roof in 2024, a new back door and garage door in 2025, and a new refrigerator, washer, and dryer in 2026. Conveniently located just minutes from downtown Cumberland, Constitution Park, Allegany College of Maryland, UPMC Western Maryland, and I-68, this home offers the perfect blend of space, comfort, and convenience.

325 Francis Ct, Cumberland

Listing courtesy of Mountainside Home Realty. Contact: 3017220190
$189,900
4 Beds ⋅ 1 Baths
MOTIVATED SELLER! ALL REASONABLE OFFERS WELCOME! Charming brick cape cod offering 4 bedrooms and 1 full bath in a very convenient location! Situated within walking distance of Fort Hill High School and Constitution Park and just minutes from UPMC, this home combines comfort and accessibility. The spacious layout features a converted carport that now serves as a cozy den, providing additional living space perfect for relaxing and entertaining. A durable metal roof offers peace of mind, while the paved driveway provides ample off-street parking. Whether you're looking for your first home or room to grow, this property offers plenty of potential in a desirable neighborhood. Schedule your private tour today!

520 Winifred Rd, Cumberland

Listing courtesy of Mountainside Home Realty. Contact: 3017220190
$297,500
3 Beds ⋅ 3 Baths
Price Reduced!! This beautifully maintained stone rancher combines timeless charm with spacious living and exceptional outdoor amenities. From the moment you arrive, the home’s attractive curb appeal and mature landscaping create a warm and inviting first impression. The main level offers a thoughtfully designed floor plan featuring a bright and comfortable living room, dining room perfect for gatherings, and a well-equipped kitchen with ample cabinetry and workspace. The cozy family room is highlighted by a wood stove, creating the perfect setting for relaxing evenings at home. Three generously sized bedrooms and two full baths provide comfortable accommodations and convenient onefloor living. The fully finished lower level greatly expands the home’s living and entertaining space. Enjoy a large family room complete with a wet bar, an additional recreation room ideal for game nights, hobbies, a home gym or could be used as a 4th bedroom, a full bath, and a dedicated laundry room with extra storage space. Step outside to your own private backyard retreat. The fenced rear yard features a sparkling inground pool, pool house, spacious rear deck, and patio area—perfect for summer entertaining, outdoor dining, and relaxing weekends. The beautifully landscaped grounds provide privacy and a peaceful setting for enjoying the outdoors. Additional features include a 2-car attached garage, a 1-car carport, and plenty of parking and storage. This exceptional property offers the perfect blend of indoor comfort and outdoor enjoyment.

203 Wempe Dr, Cumberland

Listing courtesy of Appalachian Realty. Contact:

$500,000
4 Beds ⋅ 2 Baths
BRAND NEW ROOF ADDED MAY 2026!!! Don’t miss this once-in-a-lifetime chance to own a move in ready home with over 90 acres on Haystack Mountain in the desirable Bowling Green area. Located just three minutes outside city limits, with NO CITY TAXES, this property offers the perfect balance of privacy and convenience by giving you a big country feel that is only minutes from I-68, LaVale, and Cumberland, or an easy commute to Northrop Grumman. The property features a 4-bedroom, 2-bath home with a paved driveway, an in ground pool, and a pool house. The main level includes 3 bedrooms and 2 full bathrooms, including a spacious primary bedroom and recently renovated primary bathroom. The basement includes 1 bedroom that has been completely remodeled a few months ago. The home has also undergone extensive professional improvements to the drainage system and basement, giving peace of mind to future owners and adding long-term value. In addition to a brand new architectural shingle roof that was completed in May 2026 . Step outside and explore everything this land has to offer, including some of the best year around hunting in Allegany County: Over 90 acres of usable land, a rare natural spring on the property, a custom hunting shack with scenic views, ATV/side-by-side trails throughout, frequent animal sightings (deer, bear, coyotes, and turkeys), and potential build sites for an additional, future home. Whether you’re looking to build, invest, or enjoy outdoor living, this property offers unmatched flexibility. Live in the existing home while building your custom home in the woods, then rent or sell the original house—the possibilities are endless. Utilities are available at the road, making future development even more accessible. Imagine mornings with coffee overlooking the mountains, afternoons exploring your own trails, and evenings under the stars—this is more than a home, it’s a lifestyle. If you’ve been searching for space, privacy, and potential all in one property, this is it!

12717 N Cresap St, Cumberland

Listing courtesy of Mountainside Home Realty. Contact: 3017220190
$264,900
3 Beds ⋅ 1 Baths
HERE IS SOMETHING YOU WILL NOT FIND OFTEN - COMMERCIAL LOT APPROX 1.56 ACRES ZONED B2 - COMMERCIAL INCLUDES AN OLDER HOME CURRENTLY RENTED - RESTAURANT DEVELOPMENT - RETAIL - AUTO - SO MANY POTENTIAL USES - POSSIBLE USES ON FILE - 3 LOTS INCLUDED IN SALE - AVERAGE TRAFFIC COUNT DAILY APPROX 14,000 PLUS - IMAGINE THE POSSIBLILITES - DO NOT DISTURB TENANTS

11902 Mcmullen Hwy Sw, Cumberland

Listing courtesy of Century 21 Potomac West. Contact:

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