285 Sugar Mill Dr, Osprey, FL 34229
Property image
Property image
OFF MARKET

285 Sugar Mill Dr
Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 5,578 sqft (on 1.03 acres)

$2,676,500

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $16,343/mo*
Refinance Your Home

$2,676,500

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $16,343/mo*
Refinance Your Home
5 Beds
5.5 Baths
5,578 sqft
(on 1.03 acres)

Local Information

  • Map ViewExplore the area around 285 Sugar Mill Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

This custom designed home is the must-see property in The Oaks. With space for family, working from home and for guests or multigenerational living, this private sanctuary has everything--style, luxury, and a great location, minutes from downtown and beaches and just across the street from an award-winning country club. Recently updated and impeccably maintained, its price makes it the best value on the market. This Oaks Bayside home distinguishes itself with its light airy openness with large views to its gardens, pools and lake. This remarkable floorplan offers expansive living, dining and family rooms plus an exquisite master suite opening onto a reflecting pool complete with fountain. Two spacious rooms, each with their own bathroom, offer the flexibility and the appointments to be used as offices or bedrooms. Large kitchen features solid wood cabinets fully outfitted to maximize storage, thick single- piece granite countertops, large functional island, 8 burner gas stove, double ovens, 2 dishwashers, a wine cooler and large Sub-Zero refrigerator. Unique to Florida, this home offers an exceptional amount of storage space. Huge walk-in kitchen pantry coupled with two expansive deep closets all with lacquered wood shelves, will house dishes, serving pieces, linens, candle sticks, vases, decorations and more. Another large air-conditioned storage space with shelves and cabinets is located behind the family room. Each bedroom features generous custom-designed closets. Built in solid wood, lateral file drawers and bookshelves allow for even greater organization. Both 2 car garages adjoined by a private gated motor court, include solid wood shelving and cabinetry. and hurricane-rated garage doors. Guesthouse offers 2 bedrooms with 2 baths, a kitchenette, and a large living room/ dining room opening onto a 10-foot covered porch with pool and lake views. Low maintenance gardens with mature plantings surround the home, pool and patio, offering multiple spaces for intimate or larger dining and entertainment experiences. Social or equity membership is required in this award-winning, well managed, financially secure resort club. Golf, tennis, new fitness center, award winning dining options, busy social calendar, playground, croquet, pool, pickleball & fabulous clubhouse. Convenient to Sarasota & Venice, nationally recognized Pine View School, Legacy Bike Trail and beach access!! VIRTUAL AND IN-PERSON SHOWINGS AVAILABLE. CHECK OUT THE VIDEO AND SLIDE SHOWS.
285 Sugar Mill Dr, Osprey, FL 34229 is a 5 bedroom, 6 bathroom, 5,578 sqft single-family home built in 1989. It last sold for $1,675,000 on Dec 11, 2020. It is currently off market. The Trulia Estimate is $2,676,500, with a rent estimate of $7,477/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 285 Sugar Mill Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: TileExterior: StuccoFoundation Type: ConcretePatio
Pool
Pool
Parking & Garage
GarageParking Spaces: 4Parking: Garage Attached

Property Information

Year Built
Year Built: 1989Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 1.03 acres

Price History for 285 Sugar Mill Dr

DatePriceEventSource
12/11/2020$1,675,000Sold
Stellar MLS #A4456744
10/07/2020$1,895,000PendingAgent Provided
07/18/2020$1,895,000PriceChange
Agent Provided
08/09/2019$1,695,000Listed For SaleAgent Provided
06/05/2018$1,871,000ListingRemovedAgent Provided
01/17/2018$1,871,000PriceChange
Agent Provided
04/08/2017$1,971,000PriceChange
Agent Provided
01/04/2017$2,150,000Listed For SaleAgent Provided
07/09/2016$2,100,000ListingRemovedAgent Provided
01/18/2016$2,100,000Listed For SaleAgent Provided
05/05/2015$1,850,000ListingRemovedAgent Provided
01/24/2015$1,850,000PriceChange
Agent Provided
11/20/2014$1,795,000Listed For SaleAgent Provided
08/29/2013$1,995,000ListingRemovedAgent Provided
01/09/2013$1,995,000Listed For SaleAgent Provided
12/05/2012$2,250,000ListingRemovedAgent Provided
01/28/2012$2,250,000Listed For SaleAgent Provided

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$18,422
Assessment$2,195,100
Home facts updated by county records

Comparable Sales for 285 Sugar Mill Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
370 Sugar Mill Dr, Osprey, FL
0.13
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
340 Osprey Point Dr, Osprey, FL
0.36
Single-Family Home
$1,900,000
02/10/26
5
6
6,001
67 Sugar Mill Dr, Osprey, FL
0.15
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
76 Osprey Point Dr, Osprey, FL
0.21
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
112 Osprey Point Dr, Osprey, FL
0.35
Single-Family Home
$2,315,000
10/30/25
4
5.5
8,635
140 Sugar Mill Dr, Osprey, FL
0.13
Single-Family Home
$1,325,000
06/16/26
4
4
3,286
325 Osprey Point Dr, Osprey, FL
0.34
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
282 Shell Midden Ct, Osprey, FL
0.47
Single-Family Home
$1,405,000
07/11/25
3
4.5
3,699
137 Osprey Point Dr, Osprey, FL
0.48
Single-Family Home
$1,285,000
04/08/26
4
3
3,303
402 Walls Way, Osprey, FL
0.95
Single-Family Home
$1,325,000
11/07/25
4
3.5
3,464

Nearby homes

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Assigned Schools

These are the assigned schools for 285 Sugar Mill 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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Homes for sale near 285 Sugar Mill Dr

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Off Market Homes Near 285 Sugar Mill Dr

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