3936 WAYPOINT AVENUE, Osprey, FL 34229
SOLD
APR 27, 2026

$996,100

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 2,323 sqft

3936 WAYPOINT AVENUE, Osprey, FL 34229

Est. Refi. Payment $6,420/mo*
Refinance Your Home
Currently Off Market - Sold Apr 27, 2026 for $1,001,000 (4% below list price)

Home Value

Trulia Estimate
$996K
Since last month
Increased$2K (+0.2%)
Since last year
Decreased$62K (-5.9%)
Since last sale
Decreased$5K (-0.5%)
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 +43% in the last 10 years
MonthEstimated value
2026
September 2026$996K
August 2026$1M
July 2026$994K
June 2026$996K
May 2026$998K
April 2026$1M
March 2026$940K
February 2026$1.01M
January 2026$1.01M
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
3957 WAYPOINT AVENUE, Osprey, FL
0.04
Single-Family Home
$900,000
01/16/26
3
3
2,328
1235 YACHT HARBOR DRIVE, Osprey, FL
0.34
Single-Family Home
$1,065,000
02/20/26
3
3
2,698
204 WINDWARD DRIVE, Osprey, FL
0.30
Single-Family Home
$800,000
08/24/26
3
3
2,486
1218 YACHT HARBOR DRIVE, Osprey, FL
0.30
Single-Family Home
$1,025,000
04/24/26
3
3
3,297
216 WINDWARD DRIVE, Osprey, FL
0.29
Single-Family Home
$600,000
11/18/25
3
3
2,575
447 OAK POINT ROAD, Osprey, FL
0.16
Single-Family Home
$520,000
12/30/25
4
3
2,688
264 WOODS POINT ROAD, Osprey, FL
0.14
Single-Family Home
$425,000
10/29/25
2
3
2,837
288 WOODS POINT ROAD, Osprey, FL
0.14
Single-Family Home
$445,000
04/10/26
3
2
1,788
486 YACHT HARBOR DRIVE, Osprey, FL
0.38
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
3937 WAYPOINT AVENUE, Osprey, FL 34229
0.04
$1,133,900
3
3
2,314
Off Market
3933 WAYPOINT AVENUE, Osprey, FL 34229
0.05
$1,188,100
3
3
2,391
Off Market
3925 WAYPOINT AVENUE, Osprey, FL 34229
0.06
$1,139,800
3
3
2,323
Off Market
3957 WAYPOINT AVENUE, Osprey, FL 34229
0.04
$900,000
3
3
2,328
Recently Sold
SARABAY ROAD LOT 28, Osprey, FL 34229
0.03
$241,000
-
-
-
Recently Sold
3961 WAYPOINT AVENUE, Osprey, FL 34229
0.05
$1,127,800
3
3
2,346
Off Market
3904 WAYPOINT AVENUE, Osprey, FL 34229
0.09
$958,600
3
3
2,344
Off Market
3973 WAYPOINT AVENUE, Osprey, FL 34229
0.09
$1,099,000
3
3
2,377
Off Market
811 SARABAY ROAD, Osprey, FL 34229
0.09
$425,000
2
1
1,211
Recently Sold
304 ROAD, Osprey, FL 34229
0.14
-
2
2
1,863
Off Market
288 WOODS POINT ROAD, Osprey, FL 34229
0.14
$445,000
3
2
1,788
Recently Sold

Local Information

  • Map ViewExplore the area around 3936 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
2,323 sqft
$431/sqft
2 Car Garage
HOA $521/mo

About this House

Discover coastal-inspired living at its finest in this exquisite lakefront home nestled within **Bayside**, an exclusive Taylor Morrison-built community of just 49 meticulously landscaped, maintenance-free residences. As you step inside, your eyes are immediately drawn through the expansive great room to breathtaking water views that capture the essence of waterfront living. The great room offers generous space for both elegant entertaining and relaxed everyday enjoyment, enhanced by tray ceilings and elegant crown molding—among the many thoughtful upgrades found throughout the home. The gourmet kitchen is a standout, featuring quartz countertops, a large closet pantry, premium GE Monogram appliances, an LG refrigerator, and a spacious island with counter seating and dual sided cabinets. This space overlooks the lanai and pool, creating a seamless indoor-outdoor flow. Outside, the lanai is truly exceptional—an entertainer’s dream with a fully equipped outdoor kitchen, a cozy gas fireplace, both covered and open seating areas, and a sparkling saltwater pool and spa with gas heater. All of this is beautifully framed by a brand-new 2025 panoramic screen enclosure, offering sweeping views of the lake and abundant wildlife. The primary suite is a private retreat with stunning lake views with a luxurious bath featuring a spacious walk-in shower and a full wall vanity with dual sinks. The expansive walk-in closet includes custom built-ins for maximum storage and organization. A thoughtful split-bedroom plan ensures privacy, with Bedroom 2 offering an ensuite bath, Bedroom 3 conveniently located near the main bath, and a spacious den/office providing flexible living options. Additional practical features include a well-appointed laundry room with ample cabinetry and a garage equipped with its own split HVAC system. Bayside residents enjoy exclusive access to a private waterfront park overlooking the Intracoastal Waterway, with panoramic views of Casey Key and spectacular sunsets. This open space includes a day dock, kayak and paddleboard launch, fire pit, and generous lawn area—perfect for relaxing or gathering with friends. Located west of the trail with direct water access, this rare combination of lifestyle and location is nearly impossible to find. Homes like this don’t last long. Don’t let this one get away!
3936 WAYPOINT AVENUE, Osprey, FL 34229 is a 3 bedroom, 3 bathroom, 2,323 sqft single-family home built in 2016. It last sold for $1,001,000 on Apr 27, 2026 (4% below the $1,039,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $996,100, with a rent estimate of $5,503/month.
Last check for updates: about 2 hours ago
Listed by Larry Brzostek, (941) 993-3125
RE/MAX ALLIANCE GROUP, (941) 954-5454
Bought with: Niall Phelan, (941) 914-8589, LPT REALTY, LLC, (877) 366-2213
Originating MLS: Sarasota - Manatee
Source: Stellar MLS, MLS#A4687847
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 3936 WAYPOINT AVENUE

Interior Features

Interior Details
Number of Rooms: 12Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Primary Bathroom, Bathroom 1, Bathroom 2, Balcony Porch Lanai, Den, Dining Room, Foyer, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2323 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Phone Available, Sewer Connected, Sprinkler Recycled, Street Lights, Underground Utilities, Water ConnectedAppliances: Bar Fridge, Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range Hood, Refrigerator, Tankless Water Heater, WasherDishwasherDisposalDryerLaundry: Electric Dryer Hookup,Gas Dryer Hookup,Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Exhaust Fan,Natural GasHas CoolingAir Conditioning: Central Air,Humidity Control,DuctlessHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Gas, Masonry, Non Wood Burning, OutsideSpa: Heated, In Ground, Swim SpaHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Drapes, Rods, Window Treatments, Hurricane ShuttersDoor: Outdoor Grill, Outdoor Kitchen, Sliding DoorsFlooring: Carpet, Porcelain Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Carpet, Porcelain Tile
View
Has a ViewView: Water, Lake
Security
Security: Gated Community, Security Gate, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Front Porch, Patio, ScreenedVegetation: Mature LandscapingExterior: Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters, SidewalkFoundation: SlabHas 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: Child Safety Fence, Chlorine Free, Gunite, Heated, In Ground, Lighting, Salt Water, Screen Enclosure, TilePool
Frontage
WaterfrontWaterfront: Lake, Lake Front, Bay/Harbor Access, Fishing PierRoad Frontage: Private RoadResponsible for Road Maintenance: Private Maintained RoadRoad Surface Type: Paved, AsphaltOn Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 140

Property Information

Year Built
Year Built: 2016
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Florida
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Condition: CompletedParcel Number: 0148150058

Price & Status

Price
List Price: $1,039,000Price Per Sqft: $431/sqft
Status Change & Dates
Off Market Date: Sat Apr 04 2026Possession Timing: Close Of Escrow

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: 3248 Square Feet

Community

Community Features: Dock, Fishing, Lake, Water Access, Community Mailbox, Gated Community - No Guard, ParkNot Senior Community

HOA

HOA Fee Includes: Reserve Fund, Insurance, Maintenance Grounds, Manager, Private Road, Recreational Facilities, TrashHOA Name: Patti PressanoHOA Phone: 941-444-7090Association for this Listing: Sarasota - ManateeHas an HOAHOA Fee: $521/Monthly

Lot Information

Lot Area: 8780 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: A4687847Water ViewWater View: Water, LakeShowing Advance Notice: 24Showing AttendedShowing Requirements: 24 Hour Notice, Appointment Only, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12115-N-0148150058-R-N

Additional Information

HOA Amenities: Gated

Price and Tax history

DateEventPrice
Apr 27, 2026
Source: Stellar MLS #A4687847
Sold
$1,001,000
Apr 4, 2026
Source: Stellar MLS #A4687847
Pending
$1,039,000
Apr 1, 2026
Source: Stellar MLS #A4687847
Listed For Sale
$1,039,000
Mar 31, 2026
Source: Stellar MLS #A4670043
ListingRemoved
$1,000,000
Mar 3, 2026
Source: Stellar MLS #A4670043
PriceChange
$1,000,000
Price decreased by 8%

Market trends in Osprey

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$714K
$28.67KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
112
22MoM

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 3936 WAYPOINT AVENUE

  • What is 3936 WAYPOINT AVENUE estimated to be worth?
    Trulia's estimated value for 3936 WAYPOINT AVENUE in Osprey, FL is $996,100.
  • What is the price history for 3936 WAYPOINT AVENUE?
    3936 WAYPOINT AVENUE in Osprey, FL last sold for $1,001,000 in April 2026.
  • Is Osprey a buyer's or seller's market?
    Osprey is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Osprey?
    The median sale price in Osprey is $714K. That is up $28.67K from the prior month.
  • Does 3936 WAYPOINT AVENUE have air conditioning?
    Yes, 3936 WAYPOINT AVENUE in Osprey, FL has air conditioning.
  • Does 3936 WAYPOINT AVENUE have a pool?
    Yes, 3936 WAYPOINT AVENUE in Osprey, FL has a pool.

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