3929 Waypoint Ave

2,115 Sq. Ft.
$26 / Sq. Ft.
2,115
Sq. Ft.
$26
per Sq. Ft.

Description

ANNUAL RENTAL - Pristine Single family home in the highly sought after community of Bayside in Osprey. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins. Kitchen is complete with Gas Range, Oversized Island, Quartz Countertops and walk in pantry. Guest bedrooms each have en suite bathrooms too along with one powder bath! Outdoor...ANNUAL RENTAL - Pristine Single family home in the highly sought after community of Bayside in Osprey. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins. Kitchen is complete with Gas Range, Oversized Island, Quartz Countertops and walk in pantry. Guest bedrooms each have en suite bathrooms too along with one powder bath! Outdoor space is remarkable from the heated pool and spa with southern exposure plus a bonus outdoor kitchen with built in Gas fireplace. Tandem 3 car garage will allow for ample storage for bikes and kayaks. Bayside is a fabulous place to be with opportunity to kayak and paddle board everyday. Bayside also has sunset lovers in mind with a private dock and waterfront sitting area perfect for evening romance. Minutes away from shopping, Venice Beach, Siesta Key Beach, Nokomis Beach and Casey Key Beach. Lots of time to go biking with the new Legacy trail and Oscar Scherer Park. Unfurnished No smoking 1st, last & Security for move in!
  1. Listed by Rachel Tritschler • Brokerage DRE #1030924 • RE/MAX ALLIANCE GROUP
    P: (941)-993-5892 C: (941)-993-5892 Rachel@teamtritschler.com

Property Details for 3929 Waypoint Avenue

Subdivision Name
BAYSIDE
Garage Spaces
2
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 04/13/2026 09:31 AM

Property Details for 3929 Waypoint Avenue

StatusPending
MLS #A4686669
Days on Market26
Rental Incentives-
Costs & Fees-
Available Date06/01/2026
Lease TermLease Length: 12 Months
Furnished-
Property TypeRental
MLS TypeResidential Lease / Single Family Residence
Year Built2017
Lot Size0.22 AC / 9,667 SF
CountySarasota County

Location

Listing Courtesy of RE/MAX ALLIANCE GROUP, Rachel Tritschler
Add your commute

Building Information for 3929 Waypoint Avenue

Building/Complex3929 Waypoint AveFloor-Stories-Pet Policy-Pet Policy DetailsCats OK,Dogs OK,Pet Deposit,YesYear Built2017Building Size-Lot Size0.22 AC / 9,667 SF

Property Information for 3929 Waypoint Avenue

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 3175.0
  • Building Area Units: Square Feet
  • Community Features: Dock, Fishing, Water Access, Gated Community - No Guard, Irrigation-Reclaimed Water, Sidewalks
  • Directions: From US 41/ Tamiami Trail, south of Bay Street, across from the Super-Walmart take right diagonally onto Sarabay Rd. The Bayside Community is at the end. Enter Gate Code gate code then turn right, home is on the left, no sign.
  • Elementary School: Venice Elementary
  • Middle Or Junior School: Laurel Nokomis Middle
  • High School: Venice Senior High
  • Mls Major Change Type: Pending
  • Major Change Type: Pending
  • Long Term YN: true
  • Senior Community: No
  • SW Subdiv Community Name: Bayside
  • Unit Number: No
  • Street Number: 3929
  • Street Name: WAYPOINT
  • Street Suffix: AVENUE
  • State: FL
  • City: OSPREY
Parking
  • Attached Garage: Yes
  • Carport: No
  • Garage: Yes
Taxes and HOA Information
  • Association Fee Requirement: Required
  • Association Name: Pinnacle Community Robin Estep
  • Association: Yes
  • Pet Deposit Fee: $300
  • Pet Fee Non Refundable: $300
Virtual Tour
Property
Lot Information
  • Parcel Number: 0148150034
  • Water Access: No
  • Water Extras: No
  • Living Area: 2115
Property and Assessments
  • Year Built Numeric: 2017
  • New Construction: No
  • Owner Pays: Grounds Care, Laundry, Management
Interior and Exterior Features
Exterior Features
  • Levels: One
  • Patio And Porch Features: Enclosed, Screened
  • Pool Features: Heated
  • Pool Private: Yes
  • Pool: Private
  • Pool Private: Yes
  • Security Deposit: $4,500
  • Spa Features: Heated
  • Spa: Yes
  • Waterfront Feet Total: 0
Interior Features
  • Bedrooms Total: 3
  • Bathrooms Full: 3
  • Additional Rooms: Den/Library/Office
  • Appliances: Dishwasher, Disposal, Dryer, Range, Refrigerator, Washer
  • Cooling: Central Air
  • Fireplace Features: Outside
  • Fireplace: Yes
  • Heating: Central
  • Interior Features: Cathedral Ceiling(s), Ceiling Fan(s)
  • Laundry Features: Inside, Laundry Room
  • Living Area Units: Square Feet
  • Room Count: 0.0
  • Water View: No
  • Bathrooms Half: 1
Rental
Rental Information
  • Pets Allowed: Cats OK, Dogs OK, Pet Deposit, Yes

Property History for 3929 Waypoint Avenue

DateEvent & SourcePriceAppreciation
Apr 13, 2026

Pending

MFRMLS #A4686669

—
Mar 18, 2026

Listed (Active)

MFRMLS #A4686669

$4,500—
May 15, 2024

Rented

MFRMLS #A4593051

$4,500—
DateEvent & SourcePrice
04/13/2026

Pending

MFRMLS #A4686669

—
03/18/2026

Listed (Active)

MFRMLS #A4686669

$4,500
05/15/2024

Rented

MFRMLS #A4593051

$4,500

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Schools near 3929 Waypoint Avenue

This home is within Sarasota.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Public - 2 to 12
Charter - PK to 8
Rating
School
Distance
Laurel Nokomis School
PublicPK to 8

Venice Senior High School
Public9 to 12

Pine View School
Public2 to 12

Imagine School At Palmer Ranch
CharterPK to 8

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the owner. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of RE/MAX ALLIANCE GROUP, Rachel Tritschler

The information is being provided in part by Southwest Florida Multiple Listing Service, Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2, and MarcoMls. Information deemed reliable but not guaranteed. Information is provided for consumers' personal, non-commercial use, and may not be used for any purpose other than the identification of potential properties for purchase. Copyright 2026 Southwest Florida Multiple Listing Service and MarcoMls. All Rights Reserved. The data relating to real estate for sale displayed on this website comes in part from the Broker Reciprocity Program ("BR Program") of M.L.S. of Naples, Inc. ("Naples MLS"), under License No. NCOMPN2 and MarcoMls. Properties listed with brokerage firms other than Compass are marked with the "BR House" logo. Detailed information about such properties includes the name of the brokerage firm with which the seller has listed the property. The properties displayed may not be all the properties listed with brokerage firms participating in the Naples MLS BR Program, or contained in the database compilation of Naples MLS.