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

$1,823,900

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 4,054 sqft (on 0.44 acres)

21 Sugar Mill Dr, Osprey, FL 34229

Est. Refi. Payment $11,324/mo*
Refinance Your Home
Currently Off Market - Sold Feb 26, 2016 for $700,000

Home Value

Trulia Estimate
$1.82M
Since last month
Decreased$45K (-2.4%)
Since last year
Increased$289K (+18.8%)
Since last sale
Increased$1M (+161.1%)
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 +53% in the last 10 years
MonthEstimated value
2026
August 2026$1.83M
August 2026$1.82M
July 2026$1.87M
June 2026$1.92M
May 2026$1.85M
April 2026$1.88M
March 2026$1.86M
February 2026$1.89M
January 2026$1.89M
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
25 SUGAR MILL DRIVE, Osprey, FL
0.03
Single-Family Home
$1,300,000
07/22/26
3
3.5
3,066
67 SUGAR MILL DRIVE, Osprey, FL
0.15
Single-Family Home
$1,850,000
11/07/25
4
4
4,020
919 TRANQUILITY CIRCLE, Osprey, FL
0.30
Single-Family Home
$750,000
08/14/26
4
3.5
2,854
325 OSPREY POINT DRIVE, Osprey, FL
0.19
Single-Family Home
$1,500,000
12/12/25
3
4.5
3,905
76 OSPREY POINT DRIVE, Osprey, FL
0.24
Single-Family Home
$1,450,000
06/15/26
3
4.5
4,364
140 SUGAR MILL DRIVE, Osprey, FL
0.25
Single-Family Home
$1,325,000
06/16/26
4
4
3,286
133 Osprey Point Dr, Osprey, FL
0.45
Single-Family Home
$1,054,284
06/29/26
4
3
4,099
370 SUGAR MILL DRIVE, Osprey, FL
0.27
Single-Family Home
$2,189,000
02/09/26
5
5.5
4,783
903 TRANQUILITY CIRCLE, Osprey, FL
0.29
Single-Family Home
$780,000
08/25/26
3
3
2,622
449 WEBBS COVE, Osprey, FL
0.34
Single-Family Home
$2,470,000
08/27/26
4
3.5
5,287

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
25 SUGAR MILL DRIVE, Osprey, FL 34229
0.03
$1,300,000
3
3.5
3,066
Recently Sold
38 OSPREY POINT DRIVE, Osprey, FL 34229
0.07
$2,815,100
4
5.5
3,974
Off Market
49 OSPREY POINT DRIVE, Osprey, FL 34229
0.14
$2,399,000
4
3.5
3,953
For Sale
410 BLUE GARDEN LANE LOT 6, Osprey, FL 34229
0.16
$699,000
-
-
-
For Sale
601 FERNWALK LANE, Osprey, FL 34229
0.12
$3,700,300
4
5.5
5,453
Off Market
340 OSPREY POINT DR, Osprey, FL 34229
0.19
$1,900,000
5
6
6,001
Recently Sold
325 OSPREY POINT DRIVE, Osprey, FL 34229
0.19
$1,500,000
3
4.5
3,905
Recently Sold
67 SUGAR MILL DRIVE, Osprey, FL 34229
0.15
$1,850,000
4
4
4,020
Recently Sold
519 FERNWALK LANE, Osprey, FL 34229
0.19
$1,339,100
3
3
3,396
Off Market
29 BAYHEAD LANE, Osprey, FL 34229
0.25
$725,800
3
2
2,192
Off Market
37 BAYHEAD LANE, Osprey, FL 34229
0.25
$689,400
3
2
2,168
Off Market
165 SUGAR MILL DRIVE, Osprey, FL 34229
0.20
$1,853,500
4
4.5
3,912
Off Market

Local Information

  • Map ViewExplore the area around 21 Sugar Mill Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1991
0.44 acre lot
4,054 sqft
$450/sqft
Garage

About this House

AWC - Taking Backup Offers Short Sale! Charming Colonial home located in the Oaks Golf and Tennis Country Club, Bayside. This home exudes the true timeless southern elegance feel. The classic southern influences by acclaimed architect Bo McEwen are seen throughout the spaces. The home features a grand foyer with soaring ceilings and a sweeping staircase. On the lower level you will find a spacious formal living room, separate dining room and a family room with a breakfast area. There is a spacious master suite, guest bedroom or office and two fireplaces. On the second level you will find two large bedrooms with their own screened in porch. You will find throughout the house hardwood floors, marble and exquisite crown molding and wainscoting. The outside of the home features a gorgeous pool, expansive pavered lanai overlooking a preserve, perfect for entertaining. The Oaks Club community offers two 18 hole championship golf courses, 12 lighted Har-Tru tennis courts, an active croquet court and a handful of excellent dining choices and is located close to beaches, additional five-star dining and boutique shopping centers. Listing price may not be sufficient to pay the total of all liens and costs of sale at full listing price may require approval of seller's lender(s).
21 Sugar Mill Dr, Osprey, FL 34229 is a 4 bedroom, 5 bathroom, 4,054 sqft single-family home built in 1991. It last sold for $700,000 on Feb 26, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,823,900, with a rent estimate of $6,765/month.

Home Details for 21 Sugar Mill Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Interior Details
Number of Rooms: 8Types of Rooms: Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoFoundation Type: ConcretePatioPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 2Parking: Carport, Garage Attached

Property Information

Year Built
Year Built: 1991Year Updated: 2001
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 0.44 acres

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Feb 26, 2016
Source: Stellar MLS #A4105496
Sold
$700,000
Nov 18, 2015
Source: Agent Provided
Pending
$699,000
Jun 30, 2015
Source: Agent Provided
PendingToActive
$699,000
May 12, 2015
Source: Agent Provided
Pending
$699,000
Mar 27, 2015
Source: Agent Provided
PriceChange
$699,000
Price decreased by 12%

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

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

LGBTQ Local Legal Protections

Frequently asked questions about 21 Sugar Mill Dr

  • What is 21 Sugar Mill Dr estimated to be worth?
    Trulia's estimated value for 21 Sugar Mill Dr in Osprey, FL is $1,823,900.
  • What is the price history for 21 Sugar Mill Dr?
    21 Sugar Mill Dr in Osprey, FL last sold for $700,000 in February 2016.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • 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 recently sold homes in Osprey, FL.
  • Does 21 Sugar Mill Dr have air conditioning?
    Yes, 21 Sugar Mill Dr in Osprey, FL has air conditioning.
  • Does 21 Sugar Mill Dr have a pool?
    Yes, 21 Sugar Mill Dr in Osprey, FL has a pool.

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