East Stroudsburg Homes with Chalet Style

East Stroudsburg Homes with Chalet Style

Welcome to East Stroudsburg, a charming city nestled in the heart of Monroe County, Pennsylvania. Known for its scenic beauty and vibrant community, East Stroudsburg offers a perfect blend of small-town charm and modern amenities.

One of the unique features of the real estate landscape in East Stroudsburg is the prevalence of homes with chalet style architecture. These homes are characterized by their cozy and rustic design, featuring steeply pitched roofs, large windows, and exposed wooden beams. Living in a chalet-style home in East Stroudsburg allows residents to enjoy the beauty of the surrounding nature while still being close to all the conveniences of city life.

Whether you are looking for a weekend getaway or a permanent residence, East Stroudsburg has something to offer for everyone. From outdoor enthusiasts to foodies and art lovers, this city has a diverse range of activities and attractions to explore. With easy access to hiking trails, ski resorts, and charming downtown shops and restaurants, East Stroudsburg truly has something for everyone.

If you are considering making East Stroudsburg your home, let us help you find the perfect property to suit your needs. Contact us today to learn more about the homes with chalet style architecture and other real estate opportunities in this beautiful city.

Newest East Stroudsburg Homes with Chalet Style

1274 Park Dr, East Stroudsburg
$499,000
3 Beds ⋅ 2 Baths ⋅ PM-145969 MLS
Do Not Wait to See This Active, Fully-Permitted Short Term Rental that Generated Over $81K in Gross Rental Revenue Across Just 9 Months from January 1st through September 30 2026! With annual income likely to exceed $100K in its first year in operation, this property is being delivered as a proven winner - fully turn-key, investment-ready and with proof of concept already in place! Set in a quiet East Stroudsburg neighborhood just moments to The Delaware River National Recreation Area, Shawnee Ski Resort and with ultra-easy access to Route 80 towards NJ/NY, it is rare that an active STR in this condition comes to market. Having undergone a full remodel just last year, step into something fresh, updated and loaded with mountain getaway vibes. Inside, entry foyer w wood accents leads to light and bright vaulted chalet-style main space featuring exposed beams, new and large windows. Downstairs, find awesome game room space that provides direct access to the backyard. Additional movie room features comfy couches and projector setup perfect for a fun night in. Just off the back deck access covered hot tub, barrel sauna, firepit, 'igloo' and giant chess setup to stay entertained in flat, spacious and partially-fenced backyard. NEW ductless heat/cool throughout for year-round comfort and cost efficiency. NEW roof too! Nothing to Do Here But Bring Your Bags - A Perfect Opportunity to Purchase and Get a Property In Service This Year! Do Not Delay - Call for More Info Today!

1274 Park Dr, East Stroudsburg
259 Sandlewood Dr, East Stroudsburg
$389,000
4 Beds ⋅ 2 Baths ⋅ PM-145891 MLS
Tree house Experience with all amenities & luxuries the Poconos can offer in minutes, right on the most QUIET Cul-De-Sac! This beautiful Property is located in the Amenity filled Penn Estates community, that is STR friendly and within 90 miles to NYC and only 20 minutes from the NJ Border. This property has been very well cared for and it SHOWS! 4 Great Sized bedrooms, 2 full, renovated Bathrooms, and a Kitchen that is perfectly constructed for hosting and gathering with friends and family with ALL STAINLESS STEAL APPLIANCES. The Dining room is truly a wonderful highlight, surrounded by trees, creating the feeling of tree house living! The Living room Features Vaulted Ceilings & A WOOD Burning Fireplace to cozy up around making it the PERFECT Mountain home! This location is ideal, because not only it's quiet, and although it's located on .59 Acres you are neighboring wooded acres that give you endless sight of bliss in the woods & privacy. This is a fully furnished home that is turn key ready for the new owners. NEW Roof in 2022 and New Water Heater in 2024. The Basement has a Separate walk in/out entrance (but also access within the main home) & can be used to create Additional living potential as it is currently unfinished. There is definitely room to grow even more! Whether you want to live full time, Or even use it as an investment property this could be a great opportunity to take advantage of!

259 Sandlewood Dr, East Stroudsburg
334 Clubhouse Dr, East Stroudsburg
$349,000
4 Beds ⋅ 2 Baths ⋅ PM-145529 MLS
Looking for an outstanding ski chalet, STR, vacation retreat or primary residence? Look no further! This custom-built home features 4 bedrooms, 2 full baths, solid oak floors and ceilings along with an open concept great room with a spacious loft. There's plenty of room to relax, entertain, and make lasting memories. Previously enjoyed as a vacation home, the property is being offered fully furnished, making it ideal opportunity for a primary, vacation home or short-term rental. Step outside and enjoy the peaceful natural setting, with the property backing up to 65 acres of community-owned land, providing a beautiful sense of privacy and tranquility. A true Poconos paradise you won't want to miss!

334 Clubhouse Dr, East Stroudsburg
3217 Woodchip Ln, East Stroudsburg
$324,900
3 Beds ⋅ 2 Baths ⋅ PM-145287 MLS
Welcome to this freshly painted 3-bedroom, 1.5-bath home tucked away on a quiet cul-de-sac in sought-after Penn Estates! The main level features an inviting open floor plan that flows seamlessly from the living room to the kitchen and dining area, making it ideal for everyday living and entertaining. Step outside and enjoy the first-floor deck, perfect for relaxing and taking in the peaceful surroundings. The second floor offers a spacious family room highlighted by a cozy fireplace and vaulted ceiling, along with access to a second-story deck. Two comfortable bedrooms and a full bath complete this level, while the third floor features an additional private bedroom--perfect for guests, a home office, or flexible living space. Enjoy all that Penn Estates has to offer, including multiple lakes, a community pool, tennis courts, basketball courts, and more. With fresh paint, versatile living spaces, two decks, and a peaceful cul-de-sac location, this home is ready for its next owner to move in and enjoy! Property can be an STR.

3217 Woodchip Ln, East Stroudsburg
467 Lakeside Dr, East Stroudsburg
$350,000
3 Beds ⋅ 2 Baths ⋅ PM-145229 MLS
Discover elevated Pocono living in this spacious 3-bedroom, 2-bath retreat in amenity-filled Penn Estates. Designed for both relaxation and entertaining, the home offers seasonal lake views, generous living spaces and oversized closets. The modern kitchen features stainless steel appliances and a charming breakfast room, while sun-filled interiors and skylights create a bright, airy feel. A stunning stone wood-burning fireplace anchors the living room with warmth and character. The private third-floor primary bedroom and loft offer a peaceful escape. The finished lower level features a fireplace/stove and double French doors. Multiple decks invite you to relax and take in the surroundings. Airbnb/STR potential--buyer to verify.

467 Lakeside Dr, East Stroudsburg
3257 Trafalgar Ave, East Stroudsburg
$369,900
3 Beds ⋅ 3 Baths ⋅ PM-144612 MLS
Do Not Wait to See This Fully Remodeled Modified A-Frame Retreat Tucked Away on a Private, Wooded Lot in Wilderness Acres! Blending modern upgrades with classic mountain character, this home delivers the perfect balance of style, comfort, and setting. Set back from the road with a long driveway and surrounded by trees, the property offers a peaceful, secluded feel from the moment you arrive. Inside, the dramatic open-concept main living space is highlighted by soaring vaulted ceilings, exposed beams, and rich wood finishes that create warmth and charm throughout. A wood-burning stove anchors the room, making it the perfect place to unwind. The completely updated kitchen features sleek cabinetry, modern appliances, and clean lines, flowing seamlessly into the dining and living areas. Sliding doors lead to a spacious front deck, ideal for relaxing, entertaining, or enjoying the natural surroundings. The main level offers multiple bedrooms and updated bathrooms, while the upper-level loft-style primary suite creates a comfortable and private retreat. Efficient mini-split systems provide heating and cooling year-round. Located just minutes from Route 80, Shawnee Mountain, the Delaware Water Gap, and endless outdoor recreation including hiking, skiing, and river activities, this home is perfectly positioned for both convenience and lifestyle. Move-in ready and thoughtfully updated, this is a standout Pocono property you won't want to miss.

3257 Trafalgar Ave, East Stroudsburg
5110 Yukon Dr, East Stroudsburg
$224,900
3 Beds ⋅ 2 Baths ⋅ PM-142688 MLS
Room to relax, space to gather, and a peaceful wooded setting to enjoy. This 3-bedroom, 2-bath Pocono chalet offers comfortable living indoors and out, whether you're looking for a full-time home or a weekend retreat. The main level features an open-concept living and dining area with vaulted ceilings, a wood-burning fireplace, and a kitchen with breakfast bar. Large glass doors open to an expansive deck overlooking the surrounding woods, offering plenty of space for outdoor dining, morning coffee, or simply enjoying the quiet. Downstairs, the spacious recreation room with a cozy wood stove gives you another place to gather, watch movies, or unwind. An additional room offers flexibility for a third bedroom, home office, or hobby space, with a laundry area and half bath nearby. Practical features include a roof replaced in 2017, Nest smart thermostats, wall A/C, electric baseboard heat, generator hookup, EV charging station, and a horseshoe driveway with ample parking. Community amenities include a clubhouse and indoor and outdoor pools. Skiing, hiking, lakes, shopping, and dining are all within easy reach. With inviting living spaces, a generous outdoor deck, and room to make it your own, this chalet offers a comfortable place to enjoy everything the Poconos have to offer.

5110 Yukon Dr, East Stroudsburg
5110 Yukon Dr, East Stroudsburg
$224,900
3 Beds ⋅ 2 Baths ⋅ 779980 MLS
Room to relax, space to gather, and a peaceful wooded setting to enjoy. This 3-bedroom, 2-bath Pocono chalet offers comfortable living indoors and out, whether you're looking for a full-time home or a weekend retreat. The main level features an open-concept living and dining area with vaulted ceilings, a wood-burning fireplace, and a kitchen with breakfast bar. Large glass doors open to an expansive deck overlooking the surrounding woods, offering plenty of space for outdoor dining, morning coffee, or simply enjoying the quiet. Downstairs, the spacious recreation room with a cozy wood stove gives you another place to gather, watch movies, or unwind. An additional room offers flexibility for a third bedroom, home office, or hobby space, with a laundry area and half bath nearby. Practical features include a roof replaced in 2017, Nest smart thermostats, wall A/C, electric baseboard heat, generator hookup, EV charging station, and a horseshoe driveway with ample parking. Community amenities include a clubhouse and indoor and outdoor pools. Skiing, hiking, lakes, shopping, and dining are all within easy reach. With inviting living spaces, a generous outdoor deck, and room to make it your own, this chalet offers a comfortable place to enjoy everything the Poconos have to offer.

5110 Yukon Dr, East Stroudsburg
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The data relating to real estate for sale on this web site includes listings held by MLS-IDX Participants of the Internet Data Exchange program of the Multiple Listing Service of the Pocono Mountains Association of Realtors. Listings marked with the Internet Data Exchange logo are not necessarily the listings of the owner of this web site. All listing data is the copyrighted property of the aforesaid Association and its MLS-IDX Participants with all rights reserved. The information contained herein is believed to be accurate, but no warranty as such is expressed or implied.

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