2068 ROBERTS POINT DRIVE, Windermere, FL 34786
Property image
Property image
FOR SALE
3D VIEW
1.04 ACRES

$2,150,000

Original price: $2,250,000
  • 5 Beds
  • 4 Baths
  • 4,876 sqft (on 1.04 acres)

2068 ROBERTS POINT DRIVE, Windermere, FL 34786

Est. Mortgage $15,383/mo*
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Home Highlights

Single-Family Home
Built in 1999
1.04 acre lot
$441/sqft
4 Car Garage
HOA $325/mo

Local Information

  • Map ViewExplore the area around 2068 ROBERTS POINT DRIVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

One or more photo(s) has been virtually staged. Private Windermere Estate in Guard-Gated Waterford Pointe with Detached Guest Casita, and Lake Access. A rare opportunity in one of Windermere’s most established guard-gated communities, this private estate offers the space, flexibility, and lifestyle today’s luxury buyers are actively seeking. Set on over an acre within Waterford Pointe, the property combines architectural presence, exceptional privacy, and resort-inspired living in a peaceful enclave known for estate-sized homes, mature landscaping, and private access to Lake Roberts. Designed around a dramatic courtyard pool, the home creates a true indoor-outdoor lifestyle experience, ideal for both grand entertaining and everyday living. The detached guest casita is a standout feature, offering exceptional flexibility for guests, private office use, wellness retreat, creative studio, or evolving lifestyle needs. Inside, soaring ceilings, polished marble tile flooring, detailed crown molding, and dramatic two-story living spaces create a sense of scale and elegance throughout. The thoughtfully updated chef’s kitchen is designed for gathering, featuring quartz countertops, an oversized island, premium KitchenAid and Bosch appliances, double ovens, wine refrigeration, and seamless connection to the expansive family room with custom built-ins and fireplace. The private first-floor primary suite serves as a true retreat, offering direct courtyard and pool access, a spacious custom walk-in closet, and a beautifully appointed bath with dual vanities, jetted soaking tub, and walk-in shower. A second first-floor suite provides ideal accommodations for guests or family. Upstairs, expansive, flexible living spaces include a large game room overlooking the courtyard, a dedicated office with custom built-ins, a private fitness room with balcony access, and additional secondary bedrooms thoughtfully arranged for privacy and functionality. Outdoor living is equally compelling, with a screened resort-style saltwater pool and heated spa with waterfall, covered summer kitchen, multiple entertaining spaces, and the privacy that only a homesite of this scale can provide. Waterford Pointe residents enjoy an exceptional lifestyle with private access to Lake Roberts, a waterfront clubhouse, tennis courts, playground, and beautifully tree-lined streets—all within one of Windermere’s most desirable gated communities. Additional highlights include a 4-car garage, a new whole-house generator, three HVAC systems, a newly painted exterior courtyard, and highly regarded local schools. For buyers seeking privacy, architectural character, flexible living, and established Windermere luxury—without the premium of direct lakefront pricing—this is a compelling opportunity. **Private tours available by appointment**
Last check for updates: about 4 hours ago
Listing Provided by: David Dorman, (407) 948-8295
CENTURY 21 CARIOTI, (407) 573-2121
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6397543
Also Listed on Stellar MLS.
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 2068 ROBERTS POINT DRIVE

Interior Features

Interior Details
Number of Rooms: 15Types of Rooms: Primary Bedroom, Bedroom 2, Primary Bathroom, Bathroom 2, Balcony Porch Lanai, Bonus Room, Dinette, Dining Room, Family Room, Foyer, Gym, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 4876 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Phone Available, Propane, Sprinkler Well, Street Lights, Underground Utilities, Water ConnectedAppliances: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Other, Range Hood, Refrigerator, Water Filtration System, Wine RefrigeratorDishwasherDisposalLaundry: Electric Dryer Hookup,Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: Electric,Heat Pump,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Electric, Family Room, Non Wood BurningSpa: Heated, In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Door: French Doors, Outdoor Grill, Outdoor KitchenFlooring: Brick/Stone, Carpet, Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Brick Stone, Carpet, Ceramic Tile, Hardwood
View
Has a ViewView: Trees/Woods
Security
Security: Gated Community, Security Gate, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Covered, Enclosed, Patio, Screened, Side PorchFencing: OtherVegetation: Mature Landscaping, Oak Trees, Trees/LandscapedOther Structures: Cabana, OtherExterior: Balcony, Courtyard, Fire Pit, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Entrance, Private Mailbox, Rain Gutters, SidewalkFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4Other Parking: Garage Dimensions: 21X44No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Boat,Circular Driveway,Driveway,Garage Door Opener,Garage Faces Side,Golf Cart Parking,Guest,Parking Pad
Pool
Pool: Child Safety Fence, Gunite, Heated, In Ground, Lighting, Other, Outside Bath Access, Salt Water, Screen Enclosure, Self CleaningPool
Frontage
Waterfront: Lake, Waterfront, Lake Privileges, Boat Ramp - Private, Skiing AllowedRoad Frontage: Private RoadResponsible for Road Maintenance: Private Maintained RoadRoad Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic TankWater Body: LAKE ROBERTS

Days on Market

Cumulative Days on Market: 137Days on Market: 146

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary,Courtyard,Custom,Florida,Other,Traditional
Building
Construction Materials: Block, Stone, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Condition: CompletedParcel Number: 012327911000560

Price & Status

Price
List Price: $2,150,000Price Per Sqft: $441

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINDERMERECommunity: WATERFORD POINTE PH 02 REP
School Information
Elementary School: Lake Whitney ElemJr High / Middle School: SunRidge MiddleHigh School: West Orange High

Agent Information

Listing Agent
Listing ID: O6397543

Building

Building Area
Building Area: 8410 Square Feet

Community

Community Features: Community Boat Ramp, Dock, Fishing, Lake, Water Access, Waterfront, Clubhouse, Deed Restrictions, Gated Community - Guard, Golf Carts OK, No Truck/RV/Motorcycle Parking, Park, Playground, Sidewalks, Tennis Court(s)Not Senior Community
Other
Playground

HOA

HOA Fee Includes: 24-Hour Guard, Private Road, Recreational FacilitiesHOA Name: Don AsherHOA Phone: 407-425-4561Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $325/Monthly

Lot Information

Lot Area: 1.0373 Acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Energy

Energy Efficiency Features: Thermostat

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6397543Showing Considerations: No Sign, See RemarksShowing Requirements: See Remarks, ShowingTimeUniversal Property Id: US-12095-N-012327911000560-R-N

Additional Information

HOA Amenities: Clubhouse,Fence Restrictions,Gated,Park,Playground,Recreation Facilities,Security,Tennis Court(s),Vehicle Restrictions

Around this home

What Locals Say about Windermere

At least 271 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

  • 80 % 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."
    0
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • 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
    Flag
  • 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. "
    0
    Flag
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • 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
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • 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
    Flag
  • 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
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  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
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  • 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
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  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • 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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Market trends in Windermere

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
296
11MoM

Home Value

Trulia Estimate
$2.03M
Since last month
Decreased$66K (-3.1%)
Since last year
Increased$460K (+29.3%)
Since last sale
Increased$1M (+170.6%)
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 +95% in the last 10 years
MonthEstimated value
2026
August 2026$2.03M
August 2026$2M
July 2026$2.1M
June 2026$2.1M
May 2026$2.2M
April 2026$2.24M
March 2026$1.63M
February 2026$1.6M
January 2026$1.56M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
12923 WATER POINT BOULEVARD, Windermere, FL
0.12
Single-Family Home
$2,500,000
03/17/26
5
4.5
5,005
2258 RICKOVER PLACE, Winter Garden, FL
0.25
Single-Family Home
$789,999
01/20/26
5
4
3,081
2217 RICKOVER PLACE, Winter Garden, FL
0.19
Single-Family Home
$1,039,000
05/29/26
5
5
4,324
2211 RICKOVER PLACE, Winter Garden, FL
0.18
Single-Family Home
$985,000
10/28/25
5
5
4,324
13123 LUNTZ POINT LANE, Windermere, FL
0.43
Single-Family Home
$1,650,000
05/15/26
5
4.5
3,765
2002 WATER KEY DRIVE, Windermere, FL
0.38
Single-Family Home
$1,365,000
07/16/26
5
5
3,695
2025 WINTERMERE POINTE DRIVE, Winter Garden, FL
0.56
Single-Family Home
$715,000
08/28/26
5
4
2,655
13044 LAKESHORE GROVE DRIVE, Winter Garden, FL
0.52
Single-Family Home
$800,000
10/30/25
6
4.5
3,775
1839 BLACKWATER COURT, Winter Garden, FL
0.57
Single-Family Home
$1,140,000
10/01/25
5
4
4,150
2006 WINTERMERE POINTE DRIVE, Winter Garden, FL
0.64
Single-Family Home
$740,000
08/17/26
5
4
3,011

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
2151 TILLMAN AVENUE, Winter Garden, FL 34787
0.05
$806,400
5
4
3,506
Off Market
2139 TILLMAN AVENUE, Winter Garden, FL 34787
0.07
$860,000
4
4
3,078
For Sale
2206 TILLMAN AVENUE, Winter Garden, FL 34787
0.08
$955,000
5
3
3,394
Off Market
2109 TILLMAN AVENUE, Winter Garden, FL 34787
0.14
$709,000
5
3
3,394
Off Market
2103 TILLMAN AVE, Winter Garden, FL 34787
0.16
$903,600
5
4
3,766
Off Market
2108 TILLMAN AVENUE, Winter Garden, FL 34787
0.15
$849,000
5
4
3,078
For Sale
12923 WATER POINT BOULEVARD, Windermere, FL 34786
0.12
$2,500,000
5
4.5
5,005
Recently Sold
13025 WATER POINT BLVD, Windermere, FL 34786
0.18
$2,617,500
4
3.5
5,764
Off Market
13003 NIMITZ COURT, Winter Garden, FL 34787
0.16
$825,300
4
3
2,703
Off Market
2211 RICKOVER PLACE, Winter Garden, FL 34787
0.18
$981,600
5
5
4,324
Off Market
2217 RICKOVER PLACE, Winter Garden, FL 34787
0.19
$1,039,000
5
5
4,324
Recently Sold

Price and Tax history

DateEventPrice
Aug 12, 2026
Source: Stellar MLS #O6397543
PriceChange
$2,150,000
Price decreased by 4%
Jun 1, 2026
Source: Stellar MLS #O6397543
PriceChange
$2,250,000
Price decreased by 4%
Apr 16, 2026
Source: Stellar MLS #O6397543
Listed For Sale
$2,350,000
Aug 8, 2022
Source: Stellar MLS #O6038267
ListingRemoved
Aug 5, 2022
Source: Stellar MLS #O6038267
PriceChange
$1,690,000
Price decreased by 6%

LGBTQ Local Legal Protections

David Dorman, CENTURY 21 CARIOTI, (407) 573-2121
Agent Phone: (407) 948-8295

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Frequently asked questions about 2068 ROBERTS POINT DRIVE

  • What is the estimated monthly payment for 2068 ROBERTS POINT DRIVE?
    Based on a $2,150,000 list price with 20% down at today's rates, the estimated monthly payment for 2068 ROBERTS POINT DRIVE in Windermere, FL is approximately $15,257 (about $11,366 principal & interest, $3,816 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 2068 ROBERTS POINT DRIVE compare to homes in Windermere?
    2068 ROBERTS POINT DRIVE in Windermere, FL is listed at $2,150,000, about 164% above the $814K median sale price in Windermere.
  • What do residents say about Windermere?
    Residents describe Windermere, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Windermere, FL.
  • What are the closest schools to 2068 ROBERTS POINT DRIVE?
    The closest schools to 2068 ROBERTS POINT DRIVE in Windermere, FL are Lake Whitney Elementary School (Pre-K, rated 10/10), SunRidge Middle School (rated 8/10), West Orange High School (rated 7/10).
  • Does 2068 ROBERTS POINT DRIVE have air conditioning?
    Yes, 2068 ROBERTS POINT DRIVE in Windermere, FL has air conditioning.
  • Does 2068 ROBERTS POINT DRIVE have a pool?
    Yes, 2068 ROBERTS POINT DRIVE in Windermere, FL has a pool.
2068 ROBERTS POINT DRIVE, Windermere, FL 34786 is a 5 bedroom, 4 bathroom, 4,876 sqft single-family home built in 1999. This property is currently available for sale and was listed by Stellar MLS on Apr 16, 2026. The MLS # for this home is MLS# O6397543.