516 Jennifer Lane, FL516 Jennifer Lane, FL516 Jennifer Lane, FL
Stellar MLS
1 / 71

$1,295,000

516 Jennifer Lane

Windermere, FL 34786

Listing updated: June 25, 2026 at 11:05 AM ET

Active
Stellar MLSListing courtesy of The Rosenbloom Team · Cindy Rosenbloom · MLS #O6419731 · Active · 407-376-4454
3
Beds
3
Baths
3,021
Sq Ft
1.27
Acres
1982
Built
Water viewWater accessPrivate poolFireplace1.27 acres$429/sqft360° tour
Single Family Residence

Property type

1982

Year built

55,443 sqft

Lot size

$429

Price / sq ft

$333/mo

HOA dues

0

Days on market

2

Garage spaces

X

Flood zone

About this home

OUTDOOR LIVING, ONE-STORY COMFORT & IN-TOWN WINDERMERE LIFESTYLE COME TOGETHER AT THIS RARE 1.27-ACRE WINDERMERE OAKS PROPERTY. Set within the TOWN OF WINDERMERE, this beautifully maintained one-story pool home offers privacy, space & the lifestyle buyers hope to find, with NATURAL GAS, mature landscaping, a PARTIAL BUTLER CHAIN LAKE VIEW, and exceptional outdoor living that feels like a true extension of the home. The screened pool area is the heart of the property, beautifully finished with brick pavers & designed for everyday enjoyment as well as memorable entertaining. The 35' X 20' IRREGULAR-SHAPED POOL is complemented by multiple water features, a separate step-in spa with bubbler, a custom firepit, and a highly functional summer kitchen with bar seating, grill, ice maker & refrigerator. With approximately 812 SQ FT OF OPEN FINISHED PORCH/LANAI AREA, including a main lanai approximately 62' X 12', there is room to dine, gather, relax, watch the game, host friends, or simply enjoy the peaceful setting in every season. The PRIMARY SUITE is a true highlight of the home, privately positioned and beautifully finished with a spacious bedroom, direct access to the outdoor living area, and a STUNNING PRIMARY BATH that feels calm, elegant & luxurious. Thoughtful details, generous closet space, quality finishes, and a retreat-like feel make this suite stand apart. Inside, the home offers a warm, livable floor plan with NO STAIRS & generous gathering spaces. The main living areas connect comfortably to the outdoor spaces, creating an easy flow for entertaining & everyday life. The kitchen is positioned at the center of the home with generous prep & storage space, natural gas cooking, and a connection to the main living & dining areas that keeps everyone together. Additional bedrooms & flexible rooms provide options for guests, work, hobbies, fitness, or multigenerational living. The ONE-STORY design offers long-term comfort & convenience without sacrificing space or privacy. The setting is what makes this property so special. With 1.27 ACRES inside the Town of Windermere, there is a sense of privacy & breathing room that is increasingly hard to find. Mature trees, established landscaping, and a long residential feel create a peaceful backdrop, while the partial lake view adds a lovely connection to the Butler Chain lifestyle without making the home solely about the view. Life in WINDERMERE OAKS means you are close to the charm of downtown Windermere, weekly farmers markets, community events, local parks, brick streets & the small-town character that makes this area so loved. You are also minutes from top schools, shopping, dining, major roadways & Central Florida attractions, making the location as practical as it is beautiful. This is the kind of Windermere property buyers hope to find but rarely do: 1.27 private acres, ONE-STORY LIVING, NATURAL GAS, exceptional outdoor living, a beautiful PRIMARY SUITE, a PARTIAL BUTLER CHAIN LAKE VIEW, and a setting that makes home feel like the best place to be. It invites you to slow down, gather often, celebrate outside & enjoy the lifestyle that makes the TOWN OF WINDERMERE so special.

Local Insight

At $429/sqft for a 1982 home with water views on 1.27 acres, you're paying a meaningful premium for Windermere's lakefront positioning and Butler Chain access—the location carries more value than the bones of the house itself, so your return depends heavily on either the water frontage details or future teardown/renovation potential. The $333 monthly HOA is reasonable for the area, but at 42 years old with 3 beds/3 baths across 3,000 sqft, you'll want to scrutinize the structural condition, pool equipment age, and whether the water access is deed-secured or shared—these factors can swing the value significantly in either direction.

AI-generated insight based on listing data and neighborhood context. Verify independently.

Estimated monthly payment

Principal & interest$6,548
Property taxes$521
Home insurance (est.)$594
HOA dues$333

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history0 days on market

  1. Status: Active
    Jun 25, 2026
  2. Listed$1,295,000
    Jun 25, 2026
  3. Price increased$1,295,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
0
Subdivision
Windermere Oaks
County
Orange
Year built
1982
Living area
3,021 sq ft
Price/sq ft
$429
Building area
4,498 sq ft (Public Records)
Lot size
55,443 sq ft
Lot category
1 to less than 2
Flood zone
X
Garage
2 spaces
Pool
Private pool
Annual taxes
$6,252 (2025)
Parcel #
09-23-28-9354-00-140
Zoning
WND-SFR
MLS #
O6419731

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Interior Details

Bedrooms
3
Full bathrooms
2
Half bathrooms
1
Flooring
Ceramic Tile, Tile
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Exhaust Fan, Gas Water Heater, Ice Maker, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Water Filtration System, Water Purifier, Water Softener, Wine Refrigerator
Interior features
Built-in Features, Ceiling Fans(s), Crown Molding, Eat-in Kitchen, High Ceilings, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s), Window Treatments
Laundry
Gas Dryer Hookup, Laundry Room
Stories / Levels
One
Direction faces
East
Fireplace
Yes

Heating & Cooling

Heating
Central, Electric, Heat Pump
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes
Parking features
Driveway, Garage Door Opener, Oversized

HOA & Financial

HOA fee
$4,000 / Annually
Monthly HOA
$333/mo
Total monthly fees
$333/mo
Total annual fees
$4,000
HOA name
John Prawlocki
CDD
No
Homestead exemption
Yes
Min lease term
1-2 Years
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Must follow City of Windermere guidelines

Exterior & Construction

Exterior features
Fire Pit, French Doors, Garden, Lighting, Outdoor Grill, Outdoor Kitchen, Private Yard, Rain Gutters, Storage
Construction materials
Brick, Frame, Wood Siding
Roof
Shingle
Foundation
Slab
Pool
Private pool
Water access
Yes
Water view
Yes
Road surface
Brick, Concrete

Utilities

Sewer
Septic Tank
Water source
Public, Well
Utilities
BB/HS Internet Available, Cable Available, Cable Connected, Electricity Available, Electricity Connected, Fire Hydrant, Natural Gas Available, Natural Gas Connected, Phone Available, Sprinkler Well, Underground Utilities, Water Available, Water Connected

Community

Pets allowed
Cats OK, Dogs OK, Yes

Schools

ElementaryAWindermere ElemGreatSchools ↗
MiddleCChain of Lakes MiddleGreatSchools ↗
High SchoolAOlympia HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
Great RoomFirst19x24
KitchenFirst21x16
Primary BedroomFirst22x21
Dining RoomFirst11x18
OfficeFirst11x18
Primary BathroomFirst9x20
Bedroom 2First14x14
Bedroom 3First12x18
LaundryFirst8x13

Listing Details

Listing date
2026-06-25
On market date
2026-06-25
Original list price
$1,295,000
Occupant type
Owner
MLS area
34786 - Windermere
Listing AOR
Orlando Regional
Status changed
2026-06-25
Tax legal description
WINDERMERE OAKS 10/27 LOT 14

Flood risk

Minimal riskFEMA Zone X

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

Head West on Conroy Road toward Millenia Boulevard. Continue Straight as Conroy Road transitions into Conroy Windermere Road. Stay on Conroy Windermere Road for approximately 6.5 miles, passing through the Isleworth area. Turn right onto Jennifer Lane. Arrive at 516 Jennifer Lane on your right.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of June 25, 2026 at 11:05 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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