2557 Meadowview Cir, Windermere, FL 34786
OFF MARKET

2557 Meadowview Cir
Windermere, FL 34786

  • 7 Beds
  • 4.5 Baths
  • 4,497 sqft (on 0.34 acres)

$1,227,100

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $8,510/mo*
Refinance Your Home

$1,227,100

Trulia Estimate
as of Jul 14, 2026
Est. Refi. Payment $8,510/mo*
Refinance Your Home
7 Beds
4.5 Baths
4,497 sqft
(on 0.34 acres)

Local Information

  • Map ViewExplore the area around 2557 Meadowview Cir.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Indulge in your very own slice of Paradise in highly desirable Windermere Downs, where this Multi-Generational Home, featuring a Main House and sizable Semi-Attached Guest/In-Law Cottage, beckons with its seamless blend of luxury and comfort, coupled with exclusive access to the Windermere Chain of Lakes. Step into the spacious Main house, a 5-bedroom, 3-bathroom retreat presenting exquisite design elements and expansive living spaces. Admire the grandeur of the two-story living room, adorned with ample windows that flood the space with natural light, complemented by engineered hardwood floors and a captivating fireplace. Entertain with ease in the sprawling Great Room, which encompasses a dining area, generous family room, and a two-story conservatory offering panoramic views of lush tropical gardens. The chef-inspired kitchen features GE Monogram Stainless Steel appliances, granite countertops, a breakfast bar, and a built-in pantry. Step outside from the conservatory to discover your private oasis, complete with a serene Koi Pond, a new deck for ‘al fresco’ gatherings, and brick-paved walkways winding through manicured gardens. Ascend to the upper level of the main house to find the primary suite, with two walk-in closets, a handsome ensuite bath with a soaking tub and walk-in shower, and a private sitting area or home office thru glass French doors. Three additional large bedrooms and an updated full bathroom with double sinks and a walk-in shower complete the upstairs retreat. Descend to the lower level to discover a fifth bedroom and another full bathroom with jetted walk-in tub and grab bar, offering flexibility and convenience. On the other side of the house, beyond the oversized two-car garage, lies the semi-attached Guest Cottage, a private sanctuary built in 2018. Perfect for multi-generational living or discerning guests, this two-bedroom, 1.5-bathroom in-law residence features a full-sized kitchen with a large center island, a vaulted living room with a built-out bookcase, a first-floor primary suite with a walk-in closet and ensuite bath, a secondary upstairs bedroom with walk-in closet, and full-sized laundry room. Even though the two homes are connected via a hallway – the Guest Cottage is completely separate offering unparalleled privacy, with its own exterior front door, separate one-car garage, and a tranquil 600sf screen-enclosed covered lanai overlooking the gardens. Most importantly, imagine spending your days on the lake, waterskiing, fishing, or enjoying a leisurely paddleboard ride from your private, gated lakefront access complete with a boat ramp, dock, and beach park. Perfectly positioned across from one of the many lush parks and green spaces, this idyllic Florida home is yours to embrace, offering the best of lakefront living complemented by exceptional community amenities including playgrounds, tennis courts, and abundant outdoor spaces for an active lifestyle. With recent updates including a new roof (2019), A/C units (2018, 2019), water heaters (2018, 2023), exterior and interior paint (2018), and a new deck (2024), this home is move-in ready. Conveniently located near top-rated schools, world class entertainment, shopping and dining, this multi-generational home offers the ultimate in comfort, convenience, and luxury. Come experience your best life in exclusive Windermere Downs, and discover the Florida Lifestyle you’ve always dreamed of in this exceptional Multi-Generational Home.
2557 Meadowview Cir, Windermere, FL 34786 is a 7 bedroom, 5 bathroom, 4,497 sqft single-family home built in 1978. It last sold for the $1,190,000 asking price on Nov 22, 2024. It is currently off market. The Trulia Estimate is $1,227,100, with a rent estimate of $7,182/month.

Home Highlights

Parking
3 Car Garage
Outdoor
Porch, Patio, Deck
View
Park/Greenbelt
HOA
$85/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 2557 Meadowview Cir

Interior Features

Interior Details
Number of Rooms: 15Types of Rooms: Primary Bedroom 2, Primary Bedroom, Additional Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Balcony Porch Lanai, Dining Room, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 7Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4497 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Public, Sewer Connected, Sprinkler Meter, Sprinkler Recycled, Street Lights, Underground Utilities, Water ConnectedAppliances: Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Microwave, Range, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living Room, Wood BurningHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Storm Window(s), Low Emissivity Windows, Shutters, Window Treatments, Skylight(s)Door: French Doors, Outdoor Shower, Sliding DoorsFlooring: Engineered Hardwood, Porcelain Tile
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoAccessibility: Accessible Approach with Ramp, Accessible Bedroom, Accessible Closets, Accessible Common Area, Accessible Full Bath, Accessible Kitchen, Accessible Central Living Area, Grip-Accessible FeaturesFloors: Engineered Hardwood, Porcelain Tile
View
Has a ViewView: Park/Greenbelt

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Deck, Enclosed, Patio, Porch, ScreenedFencing: Vinyl, WoodVegetation: Mature LandscapingExterior: Garden, Irrigation System, Outdoor Shower, Private Mailbox, Rain Gutters, Sprinkler Metered, StorageFoundation: BlockGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Garage Door Opener,Split Garage
Frontage
Waterfront: Lake, Waterfront, Lake Privileges, Boat Ramp - Private, Skiing AllowedRoad Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: LAKE DOWN

Days on Market

Cumulative Days on Market: 129

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: BlockNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 042328933200590

Price & Status

Price
List Price: $1,190,000
Status Change & Dates
Off Market Date: Sun Oct 27 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINDERMERECommunity: WINDERMERE DOWNS
School Information
Elementary School: Thornebrooke ElemJr High / Middle School: Gotha MiddleHigh School: Olympia High

Building

Building Area
Building Area: 5724 Square Feet

Community

Community Features: Dock, Fishing, Lake, Private Boat Ramp, Water Access, Waterfront, Association Recreation - Owned, Deed Restrictions, Golf Carts OK, Park, PlaygroundNot Senior Community
Other
Playground

HOA

HOA Fee Includes: Recreational FacilitiesHOA Name: Brie Hutchinson, Trident Assn ManagementHOA Phone: 407-374-9736Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $85/Monthly

Lot Information

Lot Area: 0.34 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6213703Showing Considerations: Pet(s) on PremisesShowing Requirements: ShowingTimeUniversal Property Id: US-12095-N-042328933200590-R-N

Additional Information

HOA Amenities: Park,Playground,Recreation Facilities,Tennis Court(s)
Last check for updates: about 3 hours ago
Listed by Heather Walker, (407) 468-6237
HAMPTON WINDSOR REALTY LLC, (407) 468-6237
Timothy Walker, (407) 468-7000
HAMPTON WINDSOR REALTY LLC, (407) 468-6237
Bought with: Aidilyn Fuentes, (407) 760-2332, REALTY GROUP SPECIALISTS, LLC, (407) 342-2110
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6213703
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

Price History for 2557 Meadowview Cir

DatePriceEventSource
11/22/2024$1,190,000Sold
Stellar MLS #O6213703
10/27/2024$1,190,000PendingStellar MLS #O6213703
10/18/2024$1,190,000PriceChange
Stellar MLS #O6213703
10/04/2024$1,220,000PriceChange
Stellar MLS #O6213703
09/19/2024$1,225,000PriceChange
Stellar MLS #O6213703
08/16/2024$1,245,000PriceChange
Stellar MLS #O6213703
07/05/2024$1,250,000PriceChange
Stellar MLS #O6213703
06/14/2024$1,285,000Listed For SaleStellar MLS #O6213703
02/24/2018$528,000Sold
N/A
12/09/2017$537,000PendingAgent Provided
10/26/2017$537,000PriceChange
Agent Provided
08/28/2017$547,000PriceChange
Agent Provided
07/20/2017$557,000Listed For SaleAgent Provided
09/30/2002$285,000Sold
N/A
05/07/1998$179,000Sold
N/A
08/16/1995$62,100Sold
N/A

Market trends in Windermere

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$722K
$50KMoM
Sale-to-List Price
97.3%
0.2%MoM
Price per sq ft
$273
$11MoM
Available listings
285
6MoM
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Property Tax and Assessment

Year2024
Tax$9,876
Assessment$881,429
Home facts updated by county records

Comparable Sales for 2557 Meadowview Cir

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9439 Westover Club Cir, Windermere, FL
0.23
Single-Family Home
$1,099,995
10/24/25
6
4.5
4,445
1924 Katie Hill Way, Windermere, FL
0.26
Single-Family Home
$935,000
12/19/25
5
3
4,089
9641 Crown Prince Ln, Windermere, FL
0.19
Single-Family Home
$1,070,000
09/30/25
5
4
3,924
9792 Wildoak Dr, Windermere, FL
0.15
Single-Family Home
$700,000
02/13/26
3
3.5
3,102
9631 Hollyglen Pl, Windermere, FL
0.13
Single-Family Home
$710,000
11/25/25
4
2.5
2,854
2107 Westover Reserve Blvd, Windermere, FL
0.57
Single-Family Home
$1,060,000
03/20/26
4
4
4,676
9639 Westover Club Cir, Windermere, FL
0.40
Single-Family Home
$832,500
05/19/26
5
3
3,248
9447 Westover Club Cir, Windermere, FL
0.26
Single-Family Home
$765,000
09/10/25
4
3
2,568
9601 Ambleside Dr, Windermere, FL
0.07
Single-Family Home
$815,000
07/21/25
4
2.5
3,018
1932 Reed Hill Dr, Windermere, FL
0.28
Single-Family Home
$797,000
10/17/25
4
3
2,867

Nearby homes

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Assigned Schools

These are the assigned schools for 2557 Meadowview Cir.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 270 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 79 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
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  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
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  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
    0
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  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
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  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
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  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
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  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
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  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
    0
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  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
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  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
    0
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  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
    5
    Flag
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
    3
    Flag
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
    0
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  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
    2
    Flag
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
    0
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  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
    2
    Flag
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
    Flag
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
    Flag
  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
    Flag
  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
    0
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  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
    0
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
    1
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  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
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  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
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  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
    1
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  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
    0
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  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
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  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
    1
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
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Apartments for Rent

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Explore by feature - Pet Friendly

40 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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Homes for sale near 2557 Meadowview Cir

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Off Market Homes Near 2557 Meadowview Cir

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