Jonathan Dempsey

Philadelphia PA

HomeSmart Realty Advisors

75 Closed Sales

$30.6M Total Value

$160K - $1.3M Price Range

$407.9K Average Price

Prior five years

About Jonathan

Your guide to luxury short term rentals. Realtor, short term rental investor (turnkey , rehab, and new construction), and owner of Live Free Hospitality - the Poconos Premier Co-Hosting service

Home Types: Townhouse, House, Lot/Land, MultiFamily, Condo

Years of Experience: 6

Education: Lafayette College

Transaction History

1 Year
2 Year
5 Year

Seller Deals

Total Deals

Total Value

$7,629,500

Average Sale Price

$544,964

Price Range

$75K - $1.3M

Buyer Deals

Total Deals

Total Value

$4,622,500

Average Sale Price

$308,167

Price Range

$12K - $1.3M

1 Year View by Quarter

Seller Deals

Total Deals

Total Value

$9,487,000

Average Sale Price

$527,056

Price Range

$75K - $1.3M

Buyer Deals

Total Deals

Total Value

$11,470,285

Average Sale Price

$358,446

Price Range

$12K - $1.3M

2 Year View by Quarter

Seller Deals

Total Deals

Total Value

$10,677,000

Average Sale Price

$485,318

Price Range

$75K - $1.3M

Buyer Deals

Total Deals

Total Value

$19,918,205

Average Sale Price

$375,815

Price Range

$12K - $1.3M

5 Year View

Neighborhoods Jonathan Has the Most Experience In

Tobyhanna

21 Sales
Clifton Township Lackawanna

10 Sales
Coolbaugh

7 Sales
Norris Square

7 Sales
Point Breeze

6 Sales
Port Richmond

4 Sales

Jonathan's Active Listings

$350,000
- 3 Beds
- 1.5 Baths
- 1,553 Sq Ft
19 Yana Ln

Albrightsville, PA
Back on market with buyer financing falling through in the final hour...Welcome to Zen Escape, a modern mountain retreat nestled in the heart of the Poconos. This turnkey Airbnb property offers a unique blend of luxury and comfort, making it an ideal home, second home, or investment for those looking to capitalize on the thriving short-term rental market with excellent proven revenue history.

Jonathan Dempsey HomeSmart Realty Advisors

$1,100,000
- 7 Beds
- 3 Baths
- 3,000 Sq Ft
257 Lidio Rd

Pocono Lake, PA
An iconic A-frame design meets exceptional investment potential in this brand new mountain home —perfectly positioned for short-term rental success. With its striking architecture, oversized layout, and prime location near Lake Sinca, Vail owned Jack Frost Ski Resort, and year-round Pocono attractions, this property is built to capture the attention of today's vacation rental

Jonathan Dempsey HomeSmart Realty Advisors

$599,999
- 5 Beds
- 3 Baths
- 2,856 Sq Ft
116 Spyglass Hill Rd

Tobyhanna, PA
116 Spyglass Hill offers a rarely seen sizable and renovated lakeview five bedroom home with phenomenal location boasting many stunning features.The main level provides wall to wall windows from all common areas of the home allowing for a consistent gentle reminder that you're surrounded by nature, natural light, and a gorgeous lakeview.The completely remodeled kitchen features

Jonathan Dempsey HomeSmart Realty Advisors

$365,000
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
114 Petrarch Trail

Albrightsville, PA
Classic A Frame Chalet with new kitchen, new floors exposed wood beams, pine ceilings, open concept living, cozy propane fireplace, detached 1 car garage, expansive front deck, and hot tub to soak in. Situated on 0.45 acres in short term rental friendly Towamensing Trails. Perfect size vacation retreat for a family or a couple's getaway. Successful STR wrapping up a 12 month annual

Jonathan Dempsey HomeSmart Realty Advisors

Co-Listing Agent

$229,000
- 2 Beds
- 1.5 Baths
- 1,007 Sq Ft
50 Telemark

Kidder Township North, PA
Completely Modernized Turn-Key Townhome! STR friendly! Walk to skiing at Jack Frost Resort, play golf at Jack Frost National, or enjoy swimming in the pristine Boulder Lake at the Boulder Lake Club during the summer! Private Back Deck woods view and hiking trail. ALL FURNISHINGS INCLUDED (furniture, dishes, linens, Smart TV's, decorations, etc.). NEW DUCTLESS SPLIT UNIT AC and HEAT, in every

Jonathan Dempsey HomeSmart Realty Advisors

Co-Listing Agent

$234,999
- 2 Beds
- 1.5 Baths
- 850 Sq Ft
66 Snow Ridge Cir

Jim Thorpe, PA
WATERFRONT END-UNIT in sought-after Snow Ridge Village, perfectly positioned on peaceful Mill Pond. Whether you're looking for a cozy mountain retreat or a high-performing short-term rental (this home grossed over $9000 in its first two months), this charming Alpine-style townhouse delivers year-round appeal.Main-level primary bedroom with en suite bath, cathedral ceilings in the living

Jonathan Dempsey HomeSmart Realty Advisors

Co-Listing Agent

$169,999
- Land
- 2 Acres
- $85,000 per Acre
0 Hidden Hollow Rd

Lackawaxen Township, PA
Come See this 2 acres waterfront property on Huggy bear lake in Pike County. Build a Home, cabin, Chalet, A-Frame; whatever your heart desires. Lot is close by to Lake Wallen Paupack. Tour the lot today! Seller has previous Perc test and survey for lot.

Jonathan Dempsey HomeSmart Realty Advisors

$425,000
- 4 Beds
- 2 Baths
- 1,355 Sq Ft
22 Mountain Glen Dr

Gouldsboro, PA
Welcome to this stunning and freshly renovated 4-bedroom, 2-bath chalet nestled in the highly sought-after, amenity-rich Big Bass Lake community. Completely turnkey with high end furnishings and amenities included. This well-maintained mountain home has it all, featuring cathedral ceilings, an open-concept living space, and a wood-burning stove that adds rustic warmth. The spacious wraparound

Jonathan Dempsey HomeSmart Realty Advisors

Awards and Designations

NAR - National Association of Realtors

Other Experience

Investments, Luxury Homes, New Construction, Property Management

Agent License #RS346832

Jonathan Dempsey

(484) 897-7409

Jonathan Dempsey

About Jonathan

Transaction History

Seller Deals

Buyer Deals

Production Over Time

1 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

2 Year View by Quarter

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Jonathan Has the Most Experience In

Jonathan's Listings and Deals

Jonathan's Active Listings

Awards and Designations

Other Experience