Jonathan Dempsey

Philadelphia PA

HomeSmart Realty Advisors

82 Closed Sales

$35.5M Total Value

$160K - $1.3M Price Range

$433K Average Price

Prior 5 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: 7

Education: Lafayette College

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	16
Total Value	$9,092,000
Average Sale Price	$568,250
Price Range	$270K - $1.2M

Buyer Deals
Total Deals	16
Total Value	$4,047,000
Average Sale Price	$252,938
Price Range	$13K - $837K

1 Year View by Quarter

Seller Deals
Total Deals	24
Total Value	$14,142,000
Average Sale Price	$589,250
Price Range	$75K - $1.3M

Buyer Deals
Total Deals	25
Total Value	$7,470,000
Average Sale Price	$298,800
Price Range	$12K - $1.3M

2 Year View by Quarter

Seller Deals
Total Deals	30
Total Value	$16,642,000
Average Sale Price	$554,733
Price Range	$75K - $1.3M

Buyer Deals
Total Deals	52
Total Value	$18,866,613
Average Sale Price	$362,819
Price Range	$12K - $1.3M

5 Year View

Neighborhoods Jonathan is Experienced In

Tobyhanna

27 Sales
Clifton

13 Sales
Coolbaugh

8 Sales
Penn Forest

7 Sales
Norris Square

6 Sales
Port Richmond

4 Sales

Jonathan's Recent Active Listings

$359,900
- 3 Beds
- 1 Bath
- 1,326 Sq Ft
2104 Mink Ln

Long Pond, PA
Unwind in a cozy modern-rustic cottage in the heart of the Poconos -- the perfect base for outdoor adventures, waterparks, and relaxing nights in. This turnkey home provides the perfect escape as your next vacation home or 100% ready to go and high performing STR asset. Top features include: Hot tub & outdoor firepit, Lake access within community, Indoor fireplace, cozy loft reading nook, and

Jonathan Dempsey HomeSmart Realty Advisors

$259,000
- 1 Bed
- 1 Bath
- 690 Sq Ft
314 Anthony Ln

Pocono Pines, PA
Turnkey Short-Term Rental | Proven Income | 44,900 Gross Income 2025 | LOW Taxes & No HOA Fully operational and income-producing short-term rental located in high-demand Pocono destination - central and highly coveted Pocono Pines. This property offers a rare opportunity to step into a true turnkey investment with established revenue history and systems already in place. The home is being sold

Jonathan Dempsey HomeSmart Realty Advisors

$245,000
- 1 Bed
- 1 Bath
- 528 Sq Ft
111 Sweet Pea Ln

Pocono Pines, PA
Turnkey Short-Term Rental | Proven Income | 42,768 Gross Income 2025 | LOW Taxes & No HOA Fully operational and income-producing short-term rental located in high-demand Pocono destination - central and highly coveted Pocono Pines. This property offers a rare opportunity to step into a true turnkey investment with established revenue history and systems already in place. The home is being sold

Jonathan Dempsey HomeSmart Realty Advisors

$279,900
- 1 Bed
- 1 Bath
- 714 Sq Ft
112 Sweet Pea Ln

Pocono Pines, PA
Turnkey Short-Term Rental | Proven Income | 46,847 Gross Income 2025 | LOW Taxes & No HOA Fully operational and income-producing short-term rental located in high-demand Pocono destination - central and highly coveted Pocono Pines. This property offers a rare opportunity to step into a true turnkey investment with established revenue history and systems already in place. The home is being sold

Jonathan Dempsey HomeSmart Realty Advisors

$385,000
- 4 Beds
- 2 Baths
- 1,500 Sq Ft
619 Washington Place

Tobyhanna, PA
Your dream second home or STR investment awaits! Completely renovated and fully furnished, move right in or rent day one. The authentic chalet look and feel is highly sought after. Spend summer nights at the deck grilling with friends, cozy up by the wood fireplace after day of skiing. Enjoy your private Pocono Chalet with your loved ones and make memories for a lifetime. The chalet is located in

Jonathan Dempsey HomeSmart Realty Advisors

$440,000
- 4 Beds
- 2 Baths
- 1,775 Sq Ft
4121 Hemlock Trail

Pocono Pines, PA
Welcome to your ideal Pocono escape in the heart of Lake Naomi -- where comfort, privacy, and year-round recreation come together seamlessly. The home offers the perfect balance of relaxed mountain charm and modern convenience, with a spacious 1775sf two story layout. Step inside to an inviting open-concept layout with soaring ceilings, abundant natural light, and a spacious great room anchored

Jonathan Dempsey HomeSmart Realty Advisors

$325,000
- 3 Beds
- 1 Bath
- 864 Sq Ft
102 Sweet Briar Rd

Pocono Pines, PA
Recently remodeled getaway home only 500 feet to the Lake & Watercraft Access. Walk to West & North Beaches for Summer Fun. Kitchen upgraded with Stainless Steel Appliances and Granite Open dining & living areas with vaulted Ceiling and cozy woodstove For Winter Nights after Skiing. Featuring a large Front Deck, on a wooded corner lot, split system A/C - a Pocono rarity, full size stack W/D,

Jonathan Dempsey HomeSmart Realty Advisors

Co-Listing Agent

$159,999
- Land
- 2 Acres
- $80,000 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

$279,900
- 2 Beds
- 1 Bath
- 728 Sq Ft
109 Sweet Pea Ln

Pocono Pines, PA
Turnkey Short-Term Rental | Proven Income | Immediate Cash Flow | 49,302 Gross Income 2025 Fully operational and income-producing short-term rental located in high-demand Pocono destination - central and highly coveted Pocono Pines. This property offers a rare opportunity to step into a true turnkey investment with established revenue history and systems already in place. The home is being sold

Jonathan Dempsey HomeSmart Realty Advisors

Recently Sold

$1,150,000

Sold Jan 22, 2026
- 7 Beds
- 3 Baths
- 3,000 Sq Ft
257 Lidio Rd

Pocono Lake, PA
- 5% Above List
- $383/SF
- 127 Days On Market
Jonathan Dempsey HomeSmart Realty Advisors

$1,110,000

Sold Jan 8, 2026
- 7 Beds
- 3 Baths
- 3,680 Sq Ft
52 Driftwood Dr

Blakeslee, PA
- 3% Below List
- $302/SF
- Current Est. Value $1M
Jonathan Dempsey HomeSmart Realty Advisors

$355,000

Sold Dec 11, 2025
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
114 Petrarch Trail

Albrightsville, PA
- 3% Below List
- $355/SF
- 91 Days On Market
- Current Est. Value $364K
Jonathan Dempsey HomeSmart Realty Advisors

$415,000

Sold Nov 15, 2025
- 3 Beds
- 2 Baths
- 1,388 Sq Ft
11 Laurel Ct

Unit JJ24

Big Bass Lake, PA
- $299/SF
- 0 Days On Market
Jonathan Dempsey HomeSmart Realty Advisors

$350,000

Sold Oct 23, 2025
- 3 Beds
- 1.5 Baths
- 1,553 Sq Ft
19 Yana Ln

Albrightsville, PA
- $225/SF
- 10 Days On Market
- Current Est. Value $364K
Jonathan Dempsey HomeSmart Realty Advisors

$1,100,000

Sold Oct 3, 2025
- 7 Beds
- 3 Baths
- 3,000 Sq Ft
245 Lidio Rd

Blakeslee, PA
- $367/SF
Jonathan Dempsey HomeSmart Realty Advisors

$1,085,000

Sold Sep 17, 2025
- 7 Beds
- 3 Baths
- 3,000 Sq Ft
261 Lidio Rd

Blakeslee, PA
- 1% Below List
- $362/SF
Jonathan Dempsey HomeSmart Realty Advisors

$390,000

Sold Sep 9, 2025
- 4 Beds
- 2 Baths
- 1,355 Sq Ft
22 Mountain Glen Dr

Gouldsboro, PA
- 8% Below List
- $288/SF
- 9 Days On Market
- Current Est. Value $390K
Jonathan Dempsey HomeSmart Realty Advisors

$370,000

Sold Aug 29, 2025
- 4 Beds
- 3 Baths
- 1,882 Sq Ft
5266 Beechwood Rd

Blakeslee, PA
- 2% Below List
- $197/SF
- 87 Days On Market
- Current Est. Value $370K
Jonathan Dempsey HomeSmart Realty Advisors

Awards and Designations

NAR - National Association of Realtors

Other Experience

Investments, Luxury Homes, New Construction, Property Management

Jonathan Dempsey

(484) 897-7409

Homes for Sale by City

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 is Experienced In

Jonathan's Listings and Deals

Jonathan's Recent Active Listings

Recently Sold

Awards and Designations

Other Experience