3937 WAYPOINT AVENUE, Osprey, FL 34229
OFF MARKET

$1,138,400

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,314 sqft

3937 WAYPOINT AVENUE, Osprey, FL 34229

Est. Refi. Payment $7,181/mo*
Refinance Your Home
Currently Off Market - Sold Apr 24, 2024 for $1,200,000

Home Value

Trulia Estimate
$1.14M
Since last month
Increased$7K (+0.6%)
Since last year
Increased$63K (+5.8%)
Since last sale
Decreased$61K (-5.1%)
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 +79% in the last 10 years
MonthEstimated value
2026
August 2026$1.14M
August 2026$1.14M
July 2026$1.13M
June 2026$1.15M
May 2026$1.14M
April 2026$1.14M
March 2026$1.14M
February 2026$1.15M
January 2026$1.14M
2025
2024
2023
2022
2021
2020
2019
2018
2017

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
3936 WAYPOINT AVENUE, Osprey, FL
0.04
Single-Family Home
$1,001,000
04/27/26
3
3
2,323
3957 WAYPOINT AVENUE, Osprey, FL
0.05
Single-Family Home
$900,000
01/16/26
3
3
2,328
1235 YACHT HARBOR DRIVE, Osprey, FL
0.31
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
204 WINDWARD DRIVE, Osprey, FL
0.27
Single-Family Home
$800,000
08/24/26
3
3
2,486
1218 YACHT HARBOR DRIVE, Osprey, FL
0.26
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
447 OAK POINT ROAD, Osprey, FL
0.13
Single-Family Home
$520,000
12/30/25
4
3
2,688
264 WOODS POINT ROAD, Osprey, FL
0.11
Single-Family Home
$425,000
10/29/25
2
3
2,837
288 WOODS POINT ROAD, Osprey, FL
0.11
Single-Family Home
$445,000
04/10/26
3
2
1,788
216 WINDWARD DRIVE, Osprey, FL
0.26
Single-Family Home
$600,000
11/18/25
3
3
2,575
486 YACHT HARBOR DRIVE, Osprey, FL
0.34
Single-Family Home
$1,325,000
08/25/26
3
3.5
2,939

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
3936 WAYPOINT AVENUE, Osprey, FL 34229
0.04
$1,001,000
3
3
2,323
Recently Sold
3933 WAYPOINT AVENUE, Osprey, FL 34229
0.01
$1,188,100
3
3
2,391
Off Market
3925 WAYPOINT AVENUE, Osprey, FL 34229
0.03
$1,146,300
3
3
2,323
Off Market
3957 WAYPOINT AVENUE, Osprey, FL 34229
0.05
$900,000
3
3
2,328
Recently Sold
SARABAY ROAD LOT 28, Osprey, FL 34229
0.06
$241,000
-
-
-
Recently Sold
3961 WAYPOINT AVENUE, Osprey, FL 34229
0.06
$1,127,800
3
3
2,346
Off Market
3904 WAYPOINT AVENUE, Osprey, FL 34229
0.09
$955,500
3
3
2,344
Off Market
3973 WAYPOINT AVENUE, Osprey, FL 34229
0.10
$1,088,600
3
3
2,377
Off Market
811 SARABAY ROAD, Osprey, FL 34229
0.13
$425,000
2
1
1,211
Recently Sold
304 ROAD, Osprey, FL 34229
0.11
-
2
2
1,863
Off Market
288 WOODS POINT ROAD, Osprey, FL 34229
0.11
$445,000
3
2
1,788
Recently Sold

Local Information

  • Map ViewExplore the area around 3937 WAYPOINT AVENUE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2016
2,314 sqft
$492/sqft
2 Car Garage
HOA $448/mo

About this House

Nestled within the highly coveted haven of Bayside, a gated community of 49 homes located on Little Sarasota Bay, this gorgeous, immaculate pool home with serene preserve views enjoys the benefits of coastal living combined with mainland convenience. Maintenance-free and just steps from the community’s waterfront park, you will enjoy luxurious living in this Taylor Morrison home that offers three bedrooms, three full baths, and a den/office. The gourmet kitchen’s quartz island and countertops, along with GE Cafe appliances, presents the perfect setting for home chefs, and overlooks the spacious dining and great room. The Primary Suite features bay windows with inviting views of the lanai, pool, and lush preserve beyond. The primary bathroom, elegant with quartz countertops, double vanities, and a spacious walk-in shower with two shower heads, adjoins the oversized walk-in closet complete with luxurious custom cabinetry. Once back into the great room, step through the sliding glass doors and you will be greeted by the screened lanai, beautifully designed with ceiling fans, well-appointed outdoor kitchen, salt-water pool, and spa, and view of the three-acre tropical preserve beyond. With high ceilings, crown molding, 8 ft. doors, large laundry room with cabinets and granite countertops, this sophisticated home includes an endless array of upgrades, including ceiling fans, tankless water heater, hurricane shutters and deluxe garage flooring. Furnishings are negotiable. As a resident of Bayside, you will enjoy the community’s private waterfront park and its unique amenities, which include a kayak/paddleboat ramp, a pier with a dock, and a fire-pit complete with Adirondack chairs . . . the perfect place to relax with friends and toast the colorful sunsets overlooking Casey Key. Bayside is just minutes from Siesta Key Beach, Nokomis beach, Legacy Trail, restaurants, and shopping. Don’t miss out on this rare opportunity to experience Sarasota living at its finest!
3937 WAYPOINT AVENUE, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,314 sqft single-family home built in 2016. It last sold for $1,200,000 on Apr 24, 2024 (4% below the $1,250,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,138,400, with a rent estimate of $4,283/month.
Last check for updates: about 8 hours ago
Listed by Toni Turner, (941) 780-0191
MICHAEL SAUNDERS & COMPANY, (941) 966-8000
Bought with: Kristin O'Connor, (941) 457-9553, GULF TO BAY SOTHEBY'S INTERNAT, (941) 964-0115
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4593940
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 3937 WAYPOINT AVENUE

Interior Features

Interior Details
Number of Rooms: 9Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Primary Bathroom, Den, Dining Room, Great Room, Kitchen, Laundry
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2314 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Available, Cable Connected, Electricity Connected, Fiber Optics, Natural Gas Connected, Sewer Connected, Underground Utilities, Water ConnectedAppliances: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Filtration System, Water SoftenerDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Gas Dryer Hookup,Inside,Laundry Room,Washer HookupMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,Heat Pump,RadiantHas CoolingAir Conditioning: Central Air,Humidity ControlHas HeatingHeating Fuel: Central
Fireplace & Spa
Spa: In GroundNo FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Double Pane Windows, Insulated Windows, Rods, Shades, Shutters, Window Treatments, Hurricane Shutters, Hurricane Shutters/WindowsDoor: Outdoor Grill, Outdoor Kitchen, Sliding DoorsFlooring: Carpet, Luxury Vinyl, Travertine
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Levels: OneFloors: Carpet, Luxury Vinyl, Travertine
View
Has a ViewView: Park/Greenbelt, Pool, Trees/Woods
Security
Security: Fire Alarm, Key Card Entry, Security Gate, Security System, Security System Owned, Smoke Detector(s), Touchless Entry, Fire Resistant Exterior, Fire/Smoke Detection Integration

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Deck, Patio, ScreenedVegetation: Mature Landscaping, Trees/LandscapedExterior: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters, SidewalkFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 20x20No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Curb Parking,Garage Door Opener,Ground Level,On Street
Pool
Pool: Deck, Gunite, Heated, In Ground, Lighting, Salt Water, Screen Enclosure, TilePool
Frontage
Waterfront: Bay/Harbor Front, Waterfront, Bay/Harbor Access, Intracoastal Waterway Access, Pond Access, Fishing Pier, SeawallRoad Frontage: Private RoadResponsible for Road Maintenance: Private Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: LITTLE SARASOTA BAY

Days on Market

Cumulative Days on Market: 64

Property Information

Year Built
Year Built: 2016
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Mediterranean
Building
Construction Materials: Block, Cement Siding, StuccoNot a New ConstructionNo Additional ParcelsDoes Not Include Home Warranty
Property Information
Parcel Number: 0148150032

Price & Status

Price
List Price: $1,250,000
Status Change & Dates
Off Market Date: Sat Mar 23 2024

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: OSPREYCommunity: BAYSIDE
School Information
Elementary School: Laurel Nokomis ElementaryJr High / Middle School: Sarasota MiddleHigh School: Venice Senior High

Building

Building Details
Builder Model: LazioBuilder Name: Taylor Morrison
Building Area
Building Area: 3311 Square Feet

Community

Community Features: Bay/Harbor Front, Boat Slip, Dock, Fishing, Intracoastal Waterway, Water Access, Waterfront, Buyer Approval Required, Deed Restrictions, Gated Community - No Guard, Irrigation-Reclaimed Water, Park, SidewalksNot Senior Community

HOA

HOA Fee Includes: Common Area Taxes, Reserve Fund, Insurance, Maintenance Grounds, Maintenance Repairs, Manager, Private RoadHOA Name: Pinnacle - John BartolomeHOA Phone: 941-444-7090Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $448/Monthly

Lot Information

Lot Area: 7287 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4593940Showing AttendedShowing Considerations: No SignShowing Requirements: Appointment Only, Contact Call Center, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0148150032-R-N

Additional Information

HOA Amenities: Gated,Maintenance,Park,Recreation Facilities,Vehicle Restrictions

Price and Tax history

DateEventPrice
Apr 24, 2024
Source: Stellar MLS #A4593940
Sold
$1,200,000
Mar 25, 2024
Source: Stellar MLS #A4593940
Pending
$1,250,000
Feb 27, 2024
Source: Stellar MLS #A4593940
PriceChange
$1,250,000
Price decreased by 2%
Feb 9, 2024
Source: Stellar MLS #A4593940
PriceChange
$1,275,000
Price decreased by 3%
Jan 19, 2024
Source: Stellar MLS #A4593940
Listed For Sale
$1,310,000

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 3937 WAYPOINT AVENUE

  • What is 3937 WAYPOINT AVENUE estimated to be worth?
    Trulia's estimated value for 3937 WAYPOINT AVENUE in Osprey, FL is $1,138,400.
  • What is the price history for 3937 WAYPOINT AVENUE?
    3937 WAYPOINT AVENUE in Osprey, FL last sold for $1,200,000 in April 2024.
  • 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 3937 WAYPOINT AVENUE have air conditioning?
    Yes, 3937 WAYPOINT AVENUE in Osprey, FL has air conditioning.
  • Does 3937 WAYPOINT AVENUE have a pool?
    Yes, 3937 WAYPOINT AVENUE in Osprey, FL has a pool.

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Off Market Homes Near 3937 WAYPOINT AVENUE

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