237 Harbor House Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

237 Harbor House Dr
Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,566 sqft (on 0.26 acres)

$1,060,300

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $6,475/mo*
Refinance Your Home

$1,060,300

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $6,475/mo*
Refinance Your Home
3 Beds
3 Baths
2,566 sqft
(on 0.26 acres)

Local Information

  • Map ViewExplore the area around 237 Harbor House Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Beautiful 3 bedroom, 2.5 bath South Bay home. WIFI provided. Heated caged pool and spa. Large enclosed Florida room with pool table, fire pit conversation area, table and chairs over looking the pool. Gas grill. Garage parking for one car, circular driveway in front of house. Tennis courts across the street from house. Club house with pool and shuffleboard courts.
237 Harbor House Dr, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,566 sqft single-family home built in 1977. It last sold for $649,000 on Jun 20, 2013. More recently, it was listed as a rental in October 2017 with an asking price of $6,500 per month. That rental listing was removed on January 30, 2018. It is currently off market. The Trulia Estimate is $1,060,300, with a rent estimate of $4,387/month.

Home Highlights

Parking
Garage
Outdoor
Patio, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 237 Harbor House Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet
Appliances & Utilities
DishwasherMicrowave
Fireplace & Spa
FireplaceHot Tub or Spa

Exterior Features

Exterior Home Features
Roof: TileExterior: Other, StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 1977Year Updated: 1992
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.26 acres

Price History for 237 Harbor House Dr

DatePriceEventSource
01/30/2018$6,500ListingRemovedAgent Provided
10/11/2017$6,500Listed For RentAgent Provided
02/15/2016$6,500ListingRemovedAgent Provided
02/12/2016$6,500Listed For RentAgent Provided
04/29/2014$5,500ListingRemovedAgent Provided
04/18/2014$5,500Listed For RentAgent Provided
06/20/2013$649,000Sold
N/A
04/22/2013$659,000PriceChange
Agent Provided
02/07/2013$649,000PriceChange
Agent Provided
11/03/2012$659,000PriceChange
Agent Provided
07/24/2012$3,800ListingRemovedAgent Provided
06/23/2012$649,000Listed For SaleAgent Provided
12/01/2011$3,800Listed For RentAgent Provided
12/01/2011$649,000ListingRemovedAgent Provided
07/06/2011$3,800ListingRemovedAgent Provided
07/02/2011$3,800Listed For RentAgent Provided
05/11/2011$3,800ListingRemovedAgent Provided
05/02/2011$3,800Listed For RentAgent Provided
04/05/2011$649,000PriceChange
Agent Provided
10/24/2010$679,000PriceChange
Agent Provided
09/23/2010$719,000PriceChange
Agent Provided
12/03/2009$799,000Listed For SaleAgent Provided
11/21/2002$100,000Sold
N/A
12/17/1997$258,000Sold
N/A

Market trends in Osprey

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$569K
$30.33KMoM
Sale-to-List Price
—
Price per sq ft
$269
$8MoM
Available listings
156
6MoM
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Property Tax and Assessment

Year2025
Tax$11,075
Assessment$895,300
Home facts updated by county records

Comparable Sales for 237 Harbor House Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
238 Lookout Point Dr, Osprey, FL
0.13
Single-Family Home
$800,000
05/01/26
3
2.5
2,676
219 Keel Way, Osprey, FL
0.11
Single-Family Home
$1,100,000
04/30/26
3
2.5
2,735
216 Windward Dr, Osprey, FL
0.38
Single-Family Home
$600,000
11/18/25
3
3
2,575
1235 Yacht Harbor Dr, Osprey, FL
0.33
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
1728 S Creek Dr, Osprey, FL
0.27
Single-Family Home
$730,000
10/24/25
3
2
2,320
102 Windward Dr, Osprey, FL
0.38
Single-Family Home
$565,000
06/04/26
3
2.5
2,134
1212 Windward Dr, Osprey, FL
0.34
Single-Family Home
$645,000
08/25/25
3
2
1,994
142 Dory Ln, Osprey, FL
0.30
Single-Family Home
$1,050,000
07/22/25
3
2
2,531
1486 Landview Ln, Osprey, FL
0.31
Single-Family Home
$817,000
06/30/26
3
2
1,869
114 Windward Dr, Osprey, FL
0.38
Single-Family Home
$585,000
06/02/26
3
2
2,037

Nearby homes

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Assigned Schools

These are the assigned schools for 237 Harbor House Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

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

  • 53 % Say neighbors are friendly

  • 48 % Say there are sidewalks

  • 42 % Say it's walkable to restaurants

  • 42 % Say streets are well-lit

  • 41 % Say there are community events

  • 40 % Say it's walkable to grocery stores

  • 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

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Apartments for Rent

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Explore by feature - Pet Friendly

9 pet-friendly rentals in Osprey, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

33 rentals with air conditioning in Osprey, FL

Explore by feature - Pool

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Explore by feature - Washer/dryer

33 rentals with a washer/dryer in Osprey, FL

Explore by feature - Outdoor Space

Homes for sale near 237 Harbor House Dr

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Off Market Homes Near 237 Harbor House Dr

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