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Below you can view all the condos for sale in the Pine Run subdivision located in Osprey Florida. Listings in Pine Run are updated daily from data we receive from the Tampa multiple listing service.

To learn more about any of these condos or to receive custom notifications when a new property is listed for sale in Pine Run, give us a call at 407-252-3959.

14 Results

Pine Run Osprey Florida Condos For Sale

Pine Run Pended $155,000

Beautiful condo exterior with a covered carport, and second-floor balcony at 767 Pine Run Dr, Osprey, FL 34229
View Details 66 Photos
Condo exterior with covered parking and a screened balcony overlooking lush landscaping at 767 Pine Run Dr, Osprey, FL 34229
Exterior of condo with a wooden staircase and a peek at the covered parking area at 767 Pine Run Dr, Osprey, FL 34229
Exterior of condo with a wooden staircase and a peek at the covered parking area at 767 Pine Run Dr, Osprey, FL 34229
On Market For 14 Days

  • Bedrooms

    1

  • Full Bath(s)

    1

  • Sq. Ft.

    736

  • Year Built

    1973

  • $/SqFt

    $211

Most of the thoughtfully chosen beach cottage furnishings and decor stay, so you can just move right in and start enjoying your new condo! COMPASS FLORIDA LLC.

Pine Run For Sale $279,000

Reduced By $10,000

Inviting exterior of a multi-story home with lush landscaping and a serene walkway leading to the entrance at 111 Woodland Pl, Osprey, FL 34229
View Details 35 Photos
Exterior view showing a gated wooden fence in a shady area with greenery around the perimeter at 111 Woodland Pl, Osprey, FL 34229
View of the carport showing the parking space with 2 vehicles parked beneath a wooden covering at 111 Woodland Pl, Osprey, FL 34229
Exterior view showing a gated wooden fence in a shady area surrounded by greenery and foliage at 111 Woodland Pl, Osprey, FL 34229
On Market For 32 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1316

  • Year Built

    1979

  • $/SqFt

    $212

Make an appt to see this fantastic condo. FLAT FEE MLS REALTY.

Pine Run Pended $175,000

Reduced By $24,000

Exterior shot of condo showcasing the walkway and the orange front door, with potted plants and a small balcony at 235 Woodland Dr, Osprey, FL 34229
View Details 93 Photos
An exterior shot of the condo showcasing its structure, roof, the balcony, and a small fenced-in yard at 235 Woodland Dr, Osprey, FL 34229
A view of the condo exterior shows the stairs leading up to the entrance, surrounded by lush tropical foliage at 235 Woodland Dr, Osprey, FL 34229
The condo exterior shows the entrance walkway and landscaping at 235 Woodland Dr, Osprey, FL 34229
*POTENTIAL GREAT VALUE
On Market For 59 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1223

  • Year Built

    1980

  • $/SqFt

    $143

Pine Run is also located less than a mile from the Gulf but not in a flood zone, no major damage sustained since the community was built in the 1970’s and because no building is over 2-stories, not subject to structural integrity inspections. COMPASS FLORIDA LLC.

Pine Run For Sale $275,000

Inviting front door with tropical landscaping, seating, and screened entry at 308 Pine Run Dr, Osprey, FL 34229
View Details 98 Photos
Exterior of condo features covered parking and second story balcony at 308 Pine Run Dr, Osprey, FL 34229
Front door adorned with a wreath, side panels, and concrete entry at 308 Pine Run Dr, Osprey, FL 34229
Light and bright entryway with coat rack, decor, and tiled floors at 308 Pine Run Dr, Osprey, FL 34229
On Market For 63 Days

  • Bedrooms

    2

  • Full Bath(s)

    1

  • Sq. Ft.

    1184

  • Year Built

    1973

  • $/SqFt

    $232

With parking included, this home is as convenient as it is charming. Don't miss out! COMPASS FLORIDA LLC.

Pine Run For Sale $250,000

Reduced By $39,900

Aerial view of condo community with ocean views, lush landscaping, and tennis courts at 362 Pine Run Dr, Osprey, FL 34229
View Details 72 Photos
Condo building featuring muted color, parking below units, and native landscaping at 362 Pine Run Dr, Osprey, FL 34229
A exterior shot of the condo showing the parking area and muted exterior at 362 Pine Run Dr, Osprey, FL 34229
Charming courtyard features a bistro set and view to interior at 362 Pine Run Dr, Osprey, FL 34229
On Market For 70 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1224

  • Year Built

    1973

  • $/SqFt

    $204

Experience the best of Osprey living at 362 Pine Run Drive. COMPASS FLORIDA LLC.

Pine Run Pended $279,000

Reduced By $36,000

Private outdoor patio features red tiling, tropical plants, and sliding glass doors at 360 Pine Run Dr, Osprey, FL 34229
View Details 69 Photos
Well-maintained landscaping and mature trees surround the exterior of this charming townhome at 360 Pine Run Dr, Osprey, FL 34229
The front entrance of the home shows the unit number and a terracotta tiled entry at 360 Pine Run Dr, Osprey, FL 34229
Private outdoor patio features a table and chairs, tropical plants, and sliding glass doors at 360 Pine Run Dr, Osprey, FL 34229
On Market For 77 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1379

  • Year Built

    1973

  • $/SqFt

    $202

Don’t miss the opportunity to make this architectural gem your own! COMPASS FLORIDA LLC.

Pine Run For Sale $299,900

Reduced By $40,000

Charming home exterior featuring lush landscaping and a well-manicured front yard at 304 Pine Run Dr, Osprey, FL 34229
View Details 57 Photos
Exterior view of a two-story condo with carport and landscaping at 304 Pine Run Dr, Osprey, FL 34229
Relaxing patio with seating area, plants, and access to interior at 304 Pine Run Dr, Osprey, FL 34229
Modern kitchen with stainless steel appliances and granite countertops at 304 Pine Run Dr, Osprey, FL 34229
On Market For 82 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1729

  • Year Built

    1973

  • $/SqFt

    $173

Don’t miss your chance—schedule your private showing today! KELLER WILLIAMS ON THE WATER S.

Pine Run For Sale $249,900

Private entrance to a condo with stairs leading to the second floor and lush landscaping at 109 Woodland Pl, Osprey, FL 34229
View Details 61 Photos
Small balcony with potted plants and a bench at 109 Woodland Pl, Osprey, FL 34229
Modern kitchen with white countertops, stainless steel appliances, and breakfast bar at 109 Woodland Pl, Osprey, FL 34229
Modern kitchen with stainless steel appliances, white countertops, and ample cabinet space at 109 Woodland Pl, Osprey, FL 34229
On Market For 116 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1223

  • Year Built

    1979

  • $/SqFt

    $204

Embrace the opportunity to reside in this peaceful blend of nature and modern living at 109 Woodland Place, where every detail is designed for comfort and serenity. KELLER WILLIAMS ON THE WATER S.

Pine Run For Sale $190,000

Reduced By $50,000

View of condo exterior with stairs, landscaping, and walkway at 137 Woodland Pl, Osprey, FL 34229
View Details 70 Photos
Condo entrance with orange door, welcome mat, and wood walkway at 137 Woodland Pl, Osprey, FL 34229
Entryway with access to the kitchen and a view of the balcony at 137 Woodland Pl, Osprey, FL 34229
Bright kitchen with white appliances, wood floors, and red curtains at 137 Woodland Pl, Osprey, FL 34229
On Market For 118 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1325

  • Year Built

    1979

  • $/SqFt

    $143

Whether you're moving right in to enjoy a seasonal retreat or to live here full time, join the residents already in on the well-kept secret of Pine Run! COMPASS FLORIDA LLC.

Pine Run Pended $245,000

Reduced By $54,000

Exterior view of a condo with landscaping and walkway at 225 Woodland Dr, Osprey, FL 34229
View Details 79 Photos
Landscaped patio area with a wooden fence and pathway at 225 Woodland Dr, Osprey, FL 34229
Small patio with table and chairs, perfect for relaxing at 225 Woodland Dr, Osprey, FL 34229
Private patio with table, chairs, and umbrella at 225 Woodland Dr, Osprey, FL 34229
On Market For 127 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1316

  • Year Built

    1980

  • $/SqFt

    $186

The recent $14,000 price reduction shows that the seller is motivated and ready for a quick sale so that you can enjoy the rest of the 2025 season immediately! COMPASS FLORIDA LLC.

Pine Run For Sale $274,900

Reduced By $12,100

Condo building exterior featuring a courtyard and landscaping at 232 Woodland Dr, Osprey, FL 34229
View Details 45 Photos
Condo entryway with a wooden bench and decorative wall art at 232 Woodland Dr, Osprey, FL 34229
Covered parking for two cars with lush green landscaping at 232 Woodland Dr, Osprey, FL 34229
Bright and airy living room with light teal couches and a large TV at 232 Woodland Dr, Osprey, FL 34229
On Market For 175 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1325

  • Year Built

    1980

  • $/SqFt

    $207

NO hurricane damage sustained to unit. PREMIER SOTHEBYS INTL REALTY.

Pine Run For Sale $249,900

Reduced By $50,000

Private backyard with a wooden fence and lush green plants at 201 Woodland Dr # 201, Osprey, FL 34229
View Details 75 Photos
Assigned carport parking with additional guest parking nearby at 201 Woodland Dr # 201, Osprey, FL 34229
Private carport with covered parking space and additional storage at 201 Woodland Dr # 201, Osprey, FL 34229
Covered carport parking space for residents at 201 Woodland Dr # 201, Osprey, FL 34229
On Market For 192 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1316

  • Year Built

    1980

  • $/SqFt

    $190

Rarely available 1st floor end unit! PREFERRED PROPERTIES OF VENICE INC.

Pine Run For Sale $267,300

Reduced By $2,200

Red front door entrance with lush tropical landscaping at 758 Pine Run Dr # 758, Osprey, FL 34229
View Details 61 Photos
Red front door entrance with lush tropical landscaping at 758 Pine Run Dr # 758, Osprey, FL 34229
Red front door with louvered sides and a welcome mat at 758 Pine Run Dr # 758, Osprey, FL 34229
Aerial view of community pool, building, and lush landscaping at 758 Pine Run Dr # 758, Osprey, FL 34229
On Market For 243 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1184

  • Year Built

    1973

  • $/SqFt

    $226

With its proximity to the beach, this property is perfect for those seeking a comfortable coastal lifestyle. Schedule your showing today! REALNET FLORIDA REAL ESTATE.

Pine Run For Sale $284,900

Reduced By $20,000

Condo building with lush landscaping and walkway at 207 Woodland Dr # 207, Osprey, FL 34229
View Details 48 Photos
Aerial view of a community with lush landscaping, tennis courts, and water access at 207 Woodland Dr # 207, Osprey, FL 34229
Bright entryway with hardwood floors, built-in shelving, and access to other rooms at 207 Woodland Dr # 207, Osprey, FL 34229
Light-filled hallway with wood floors, offering views to living room and other rooms at 207 Woodland Dr # 207, Osprey, FL 34229
On Market For 337 Days

  • Bedrooms

    2

  • Full Bath(s)

    2

  • Sq. Ft.

    1325

  • Year Built

    1980

  • $/SqFt

    $215

Pine Run is nestled between Sarasota and Downtown Venice and is 7 miles away from the famous Siesta Key Beach, voted the #1 beach in the U.S. PREMIER SOTHEBYS INTL REALTY.

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Viewing CONDOS 1 to 14 of 14

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at 407-252-3959 and speak with one of our real estate consultants.

Popular Condos

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Anna Maria
$673,475
$622,500
4
0.0%
50.0%
140

Bradenton
$330,702
$299,900
1355
0.2%
63.5%
111

Bradenton Beach
$718,880
$500,000
31
0.0%
38.7%
112

Cortez
$752,670
$787,500
10
0.0%
70.0%
135

Ellenton
$367,467
$377,450
6
0.0%
33.3%
35

Englewood
$358,211
$299,900
298
0.0%
57.7%
121

Holmes Beach
$855,741
$749,900
56
0.0%
42.9%
108

Lakewood Ranch
$412,067
$375,000
202
0.5%
69.8%
138

Longboat Key
$1,712,909
$1,010,000
300
0.0%
53.7%
93

Nokomis
$362,053
$340,500
77
0.0%
63.6%
102

North Port
$290,359
$289,900
105
0.0%
60.0%
104

Palmetto
$425,305
$335,000
119
0.0%
58.8%
98

Parrish
$328,392
$324,945
116
0.0%
68.1%
116

Sarasota
$828,052
$425,000
2061
0.3%
52.8%
112

Venice
$368,158
$335,000
838
0.4%
64.6%
106

EasyStreet

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