296 PINE RANCH TRAIL, Osprey, FL 34229
Property image
Property image
FOR SALE
NEW - 1 HR AGO
1.14 ACRES

$1,100,000

  • 5 Beds
  • 3.5 Baths
  • 3,354 sqft (on 1.14 acres)

296 PINE RANCH TRAIL, Osprey, FL 34229

Est. Mortgage $6,743/mo*
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Home Highlights

Parking
2 Car Garage
Outdoor
Pool
HOA
None
Price/Sqft
$328
Climate Control
Central & Central Air
Listed
Less than a day ago

Local Information

  • Map ViewExplore the area around 296 PINE RANCH TRAIL.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Welcome to this rare slice of coastal paradise tucked away in the boutique enclave of Pine Ranch East in Osprey, Florida. Situated on a sprawling 1.137-acre private lot, this magnificent residence offers an extraordinary blend of space, serenity, and convenience. The property boasts five spacious bedrooms and three-and-a-half baths, providing a flexible layout designed to accommodate large families, host overnight guests, or create dedicated home office spaces. Every detail of the interior reflects thoughtful maintenance and pride of ownership, offering a seamless flow between the primary living areas. Designed for quintessential Florida living, the expansive backyard functions as your own private resort. Step out onto the oversized covered lanai to entertain year-round, or cool off in the crystal-clear heated pool and integrated spa while taking in the tranquil scenery of your secluded acreage. Despite the incredible privacy, you are just minutes away from pristine Gulf beaches and iconic local dining hot spots like Pops Sunset Grill and the Casey Key Fish House. Adding to the unmatched value of this property is its setting within Pine Ranch East, an exclusive neighborhood comprised of only 26 homes. While the community maintains an established HOA structure, homeowners enjoy the astonishing benefit of paying no HOA fees thanks to a unique financial setup that leaves the neighborhood fully funded years into the future. Contact us today to learn more about this remarkable community story or to schedule your private tour.
Last check for updates: about 1 hour ago
Listing Provided by: Darren Dowling, (941) 204-0493
BEYOND REALTY LLC, (941) 467-4673
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4704317
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 296 PINE RANCH TRAIL

Interior Features

Interior Details
Number of Rooms: 12Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Primary Bathroom, Bathroom 2, Bathroom 3, Dining Room, Family Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3354 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity ConnectedAppliances: Oven, Cooktop, Dishwasher, Dryer, Refrigerator, WasherDishwasherDryerLaundry: Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Spa: HeatedNo FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Window TreatmentsDoor: Sliding DoorsFlooring: Carpet, Engineered Hardwood, Tile
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Carpet, Engineered Hardwood, Tile
View
Has a ViewView: Garden, Park/Greenbelt

Exterior Features

Exterior Home Features
Roof: ShingleExterior: GardenFoundation: SlabGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Pool
Pool: Heated, In GroundPool
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Days on Market: <1 day on Trulia

Property Information

Year Built
Year Built: 1995
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 0141080010

Price & Status

Price
List Price: $1,100,000Price Per Sqft: $328

Active Status

MLS Status: Active

Location

Direction & Address
City: OSPREYCommunity: PINE RANCH EAST

Agent Information

Listing Agent
Listing ID: A4704317

Building

Building Area
Building Area: 4500 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 1.137 Acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4704317Showing Requirements: ShowingTimeUniversal Property Id: US-12115-N-0141080010-R-N

Around this home

What Locals Say about Osprey

At least 46 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 87 % Say it's dog friendly

  • 85 % Say it's quiet

  • 84 % Say parking is easy

  • 75 % Say people would walk alone at night

  • 74 % Say there's wildlife

  • 67 % Say yards are well-kept

  • 67 % Say there's holiday spirit

  • 64 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 41 % Say there are community events

  • 31 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Lindsey W.
    "It’s a quiet and low key suburb area of Sarasota county. It’s very accessible to I-75 and Nokomis beach and about a 25 minute drive to siesta key beach. "
    4
    Flag
  • Mary V.
    "I am retired now but my commute to Stickney Point was only about 10 min and downtown was about 25 min during rush hour when there is no construction "
    0
    Flag
  • Mary V.
    "Pineview School is very close, nice safe area for children. CVS and Publix are also close, as well as Historic Spanish Pointe. The beach is ten minutes or less."
    3
    Flag
  • Bob T.
    "I don’t commute....retired. There are no sidewalks here and our street has a large amount of speeders making walking dangerous. Some neighbors park on the county right of way destroying our water flow/drainage which has caused flooding here. Many homes are unkept even though there is an active hoa."
    14
    Flag
  • Bob T.
    "Neighborhood is pet friendly. Wide road we walking dogs. Only problem noticed now is daily construction vehicles speeding in neighborhood."
    1
    Flag
  • Larysathor
    "Well, the Mother Nature taking its tall, water level raised over last ten years and a lot of beaches are washed out to nonexistence."
    0
    Flag
  • Brenda F. D.
    "Neighborhood is beautiful love the area close to everything and beaches and shopping . Local restaurant "
    1
    Flag
  • Michelle C.
    "I've lived in this neighborhood for twenty years +. My neighbors are the friendliest. We all look out for each other and lend a hand when needed. Can't think of anywhere else I'd want to live."
    0
    Flag
  • nancybuscher
    "This quiet, beautifully landscaped, pet friendly subdivision is close to beaches, shopping, restaurants, cultural events in Sarasota and Venice, beside Oscar Scherer State Park for hickers & boaters, and has easy access to airports by way of US41 & I-75."
    0
    Flag
  • info
    "Centrally located, minutes to beaches and shopping"
    1
    Flag
  • bookwoman39
    "Wonderful community, close to Sarasota and all restaurants, cultural activities, etc. The condo development is a designated bird sanctuary. Nice pools, exercise room, community room. Good neighbors. What the development lacks is diversity. "
    0
    Flag
  • trishmainey1111
    "Osprey Florida is one of the most beautiful, accessible communities in Florida. Ten minutes to the white sands beach and ten minutes to I-75. "
    1
    Flag
  • Gail L.
    "I work here, belong to the club and have lived in the neighborhood for the last 12 years it is one of 5 golf communities I have belonged to and bar none my favorite due to the people that live here. They are multicultural, down to earth and just fabulous. This is a community that rates above the rest . it is very common for folks to move up and down in house sizes and styles as their lifestyles change. Give me a call as I'd love to show you around. "
    0
    Flag

Market trends in Osprey

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
133
7MoM

Home Value

Trulia Estimate
$1.05M
Since last month
Decreased$16K (-1.5%)
Since last year
Decreased$272K (-20.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +62% in the last 10 years
MonthEstimated value
2026
August 2026$1.05M
July 2026$1.06M
June 2026$1.06M
May 2026$1.06M
January 2026$1.23M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
462 E MACEWEN DRIVE, Osprey, FL
0.13
Single-Family Home
$1,500,000
09/19/25
3
2.5
2,611
448 E MACEWEN DRIVE, Osprey, FL
0.18
Single-Family Home
$1,865,160
08/27/26
4
3.5
3,768
453 E MACEWEN DRIVE, Osprey, FL
0.18
Single-Family Home
$1,850,000
01/22/26
4
3.5
4,191
201 EAGLENOOK WAY, Osprey, FL
0.43
Single-Family Home
$1,014,000
11/12/25
4
3
3,379
898 MACEWEN DRIVE, Osprey, FL
0.44
Single-Family Home
$1,700,000
09/18/25
4
4
4,132
600 EAGLE WATCH LANE, Osprey, FL
0.45
Single-Family Home
$2,035,000
06/18/26
3
3
3,681
889 MACEWEN DRIVE, Osprey, FL
0.51
Single-Family Home
$2,100,000
01/30/26
4
4
3,235
895 MACEWEN DRIVE, Osprey, FL
0.50
Single-Family Home
$2,000,000
02/09/26
3
3.5
4,828

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
328 PINE RANCH TRAIL, Osprey, FL 34229
0.06
$1,318,400
4
3
3,215
Off Market
269 PINE RANCH TRAIL, Osprey, FL 34229
0.12
-
4
3.5
3,572
Off Market
462 E MACEWEN DRIVE, Osprey, FL 34229
0.13
$1,472,000
3
2.5
2,611
Off Market
453 E MACEWEN DRIVE, Osprey, FL 34229
0.18
$1,850,000
4
3.5
4,191
Recently Sold
451 MAC EWEN DR, Osprey, FL 34229
0.18
$1,997,300
4
3.5
4,368
Off Market
448 E MACEWEN DRIVE, Osprey, FL 34229
0.18
$1,865,160
4
3.5
3,768
Recently Sold
465 MACEWEN DRIVE, Osprey, FL 34229
0.20
$2,021,100
5
5
4,357
Off Market
336 PINE RANCH EAST ROAD, Osprey, FL 34229
0.21
$873,900
4
3
2,705
Off Market
402 PINE RANCH EAST ROAD, Osprey, FL 34229
0.24
$573,700
3
3.5
2,887
Off Market
851 E BAY STREET, Osprey, FL 34229
0.25
$839,400
3
2
2,329
Off Market
482 E MACEWEN DRIVE, Osprey, FL 34229
0.26
$2,083,300
4
3
3,327
Off Market

Price and Tax history

DateEventPrice
Aug 28, 2026
Source: Stellar MLS #A4704317
Listed For Sale
$1,100,000
Jun 2, 2026
Source: Stellar MLS #A4653218
ListingRemoved
$1,150,000
May 1, 2026
Source: Stellar MLS #A4653218
PriceChange
$1,150,000
Price decreased by 8%
Mar 28, 2026
Source: Stellar MLS #A4653218
PriceChange
$1,250,000
Price decreased by 3%
Feb 3, 2026
Source: Stellar MLS #A4653218
PriceChange
$1,295,000
Price decreased by 4%

LGBTQ Local Legal Protections

Darren Dowling, BEYOND REALTY LLC, (941) 467-4673
Agent Phone: (941) 204-0493

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Frequently asked questions about 296 PINE RANCH TRAIL

  • What is the estimated monthly payment for 296 PINE RANCH TRAIL?
    Based on a $1,100,000 list price with 20% down at today's rates, the estimated monthly payment for 296 PINE RANCH TRAIL in Osprey, FL is approximately $6,916 (about $5,677 principal & interest, $1,164 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Osprey?
    Residents describe Osprey, FL as dog-friendly, quiet, and easy to park in. Most residents say you need a car. See homes for sale in Osprey, FL.
  • What are the closest schools to 296 PINE RANCH TRAIL?
    The closest schools to 296 PINE RANCH TRAIL in Osprey, FL are Laurel Nokomis School (Pre-K/Elementary/Middle, rated 8/10), Venice Senior High School (rated 7/10).
  • What is 296 PINE RANCH TRAIL estimated to be worth?
    Trulia's estimated value for 296 PINE RANCH TRAIL in Osprey, FL is $1,049,400.
  • Does 296 PINE RANCH TRAIL have air conditioning?
    Yes, 296 PINE RANCH TRAIL in Osprey, FL has air conditioning.
  • Does 296 PINE RANCH TRAIL have a pool?
    Yes, 296 PINE RANCH TRAIL in Osprey, FL has a pool.
296 PINE RANCH TRAIL, Osprey, FL 34229 is a 5 bedroom, 4 bathroom, 3,354 sqft single-family home built in 1995. This property is currently available for sale and was listed by Stellar MLS on Aug 28, 2026. The MLS # for this home is MLS# A4704317.