Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park Avenue. Inside, rich hardwood floors run throughout the living spaces, complemented by Restoration Hardware lighting that brings a refined, cohesive feel to every room. The welcoming foyer opens to a gracious formal living room with a gas fireplace and custom built-ins, an elegant yet comfortable space for entertaining or relaxing. Just beyond, the formal dining room is well proportioned for hosting holiday gatherings and dinner parties with ease. The heart of the home is the expansive chef’s kitchen, thoughtfully designed for everyday living and effortless entertaining. An oversized island anchors the space, topped with Carrara marble counters and offering generous seating. A dual Wolf oven with six-burner range plus French cooktop, custom cabinetry, walk-in pantry, and a butler’s pantry complete with under-counter wine refrigerator provide beauty and functionality. A spacious breakfast room filled with natural light overlooks the backyard and flows seamlessly into the family room. Here, a gas fireplace, custom built-ins and three sets of French doors create a warm focal point while inviting in the outdoors. The first-floor primary suite serves as a private retreat, featuring large windows with tranquil views of the pool and direct access to the covered lanai. Dual walk-in closets provide ample storage, and the spa-like primary bath is finished in Carrara marble, offering a large soaking tub and an expansive glass-enclosed shower with dual shower heads. Two powder baths, one thoughtfully designed as a pool bath, along with one of two laundry rooms complete the main level. Upstairs, four additional bedrooms and a dedicated office provide generous space for family and guests. Two of the bedrooms feature private en-suite baths, while the remaining two share a well-appointed Jack & Jill bath. One of these rooms is arranged as a bonus lounge, offering flexibility to serve as a fifth bedroom, media room or additional gathering space if desired. The thoughtful second-floor layout easily adapts to a variety of lifestyle needs, whether accommodating guests, growing families or multi-generational living. A secondary laundry room upstairs adds an added layer of everyday convenience. Outdoor living is equally impressive. The spacious covered lanai with summer kitchen overlooks the saltwater, heated pool and spa, creating an extension of the interior living space. Brick paver flooring continues from the lanai to the open patio, offering multiple areas for lounging, dining and entertaining beneath the Florida sky. Ideally in a desirable location and zoned for sought-after Audubon Park K-8, 2040 Randall Circle offers timeless style, thoughtful design and seamless indoor-outdoor living in one of the area’s charming neighborhoods.
Sold for $3,000,000
$3,000,000
2040 Randall Cir, Winter Park, FL 32789
5beds
4,636sqft
Single Family Residence
Built in 2017
0.27 Acres Lot
$3,000,500 Zestimate®
$647/sqft
$7,494 Estimated rent
Home value
$3,000,500
$2.76M - $3.24M
$7,494/mo
Zestimate® history
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List your homeWhat's special
Gas fireplaceDetached two-car garageClassic curb appealOversized islandCustom built-insCustom cabinetryRestoration hardware lighting
Zillow last checked:
Listing updated:
Listed by:
Mick Night 407-629-4446,
PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
Bought with:
Toni Cafferty, 3348224
COMPASS FLORIDA LLC
Source: Stellar MLS,MLS#: O6386920
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 6
- Full bathrooms: 4
- 1/2 bathrooms: 2
Rooms
- Room types: Breakfast Room Separate, Den/Library/Office, Family Room, Dining Room, Living Room, Utility Room
Primary bedroom
- Features: En Suite Bathroom, Walk-In Closet(s)
- Level: First
- Area: 285 Square Feet
- Dimensions: 19x15
Bedroom 2
- Features: En Suite Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 195 Square Feet
- Dimensions: 15x13
Bedroom 3
- Features: En Suite Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 195 Square Feet
- Dimensions: 15x13
Bedroom 4
- Features: Jack & Jill Bathroom, Walk-In Closet(s)
- Level: Second
- Area: 168 Square Feet
- Dimensions: 14x12
Bedroom 5
- Features: Jack & Jill Bathroom, No Closet
- Level: Second
- Area: 221 Square Feet
- Dimensions: 17x13
Primary bathroom
- Features: Bidet, Built-In Shower Bench, Multiple Shower Heads, Split Vanities, Stone Counters, Tub with Separate Shower Stall, Water Closet/Priv Toilet
- Level: First
- Area: 240 Square Feet
- Dimensions: 16x15
Balcony porch lanai
- Level: First
- Area: 400 Square Feet
- Dimensions: 20x20
Dinette
- Level: First
- Area: 104 Square Feet
- Dimensions: 13x8
Dining room
- Features: En Suite Bathroom
- Level: First
- Area: 192 Square Feet
- Dimensions: 16x12
Family room
- Features: Built-In Shelving
- Level: First
- Area: 260 Square Feet
- Dimensions: 20x13
Kitchen
- Features: Kitchen Island, Stone Counters, Pantry
- Level: First
- Area: 285 Square Feet
- Dimensions: 19x15
Living room
- Features: Built-In Shelving
- Level: First
- Area: 209 Square Feet
- Dimensions: 19x11
Office
- Features: Built-in Closet
- Level: Second
- Area: 63 Square Feet
- Dimensions: 9x7
Heating
- Central, Zoned
Cooling
- Central Air, Zoned
Appliances
- Included: Bar Fridge, Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater
- Laundry: Inside, Laundry Room
Features
- Built-in Features, Coffered Ceiling(s), Crown Molding, Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
- Flooring: Tile, Hardwood
- Doors: French Doors, Outdoor Kitchen
- Windows: Window Treatments
- Has fireplace: Yes
- Fireplace features: Family Room, Gas, Living Room, Outside
Interior area
- Total structure area: 6,085
- Total interior livable area: 4,636 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Side
- Garage spaces: 2
- Details: Garage Dimensions: 32x24
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Rear Porch
- Exterior features: Irrigation System, Lighting, Outdoor Kitchen, Rain Gutters, Sidewalk
- Has private pool: Yes
- Pool features: Gunite, Heated, In Ground, Lighting, Pool Sweep, Salt Water
- Has spa: Yes
- Spa features: Heated, In Ground
- Fencing: Fenced
Lot
- Size: 0.27 Acres
- Features: Corner Lot, City Lot, Landscaped, Level
- Residential vegetation: Mature Landscaping, Trees/Landscaped
Details
- Parcel number: 072230125203110
- Zoning: R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 2017
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Natural Gas Connected, Public, Underground Utilities
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: CHARMONT
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $647/sqft
- Tax assessed value: $1,663,176
- Annual tax amount: $24,891
- Date on market: 3/5/2026
- Cumulative days on market: 74 days
- Ownership: Fee Simple
- Total actual rent: 0
- Road surface type: Brick
Price history
| Date | Event | Price |
|---|---|---|
| 6/29/2026 | Sold | $3,000,000-10.4%$647/sqft |
Source:  Stellar MLS #O6386920 Report a problem | ||
| 5/19/2026 | Pending sale | $3,350,000$723/sqft |
Source: Stellar MLS #O6386920 Report a problem | ||
| 3/28/2026 | Price change | $3,350,000-2.9%$723/sqft |
Source: Stellar MLS #O6386920 Report a problem | ||
| 3/5/2026 | Listed for sale | $3,450,000+708%$744/sqft |
Source: Stellar MLS #O6386920 Report a problem | ||
| 6/24/2015 | Sold | $427,000$92/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $24,891 +9.7% | $1,535,793 +10% |
| 2023 | $22,696 +14.1% | $1,396,175 +10% |
| 2022 | $19,892 +9.3% | $1,269,250 +10% |
| 2021 | $18,199 -2.2% | $1,153,864 -0.5% |
| 2020 | $18,606 -2.2% | $1,159,893 -0.5% |
| 2019 | $19,023 +1.8% | $1,165,923 +3.3% |
| 2018 | $18,681 | $1,128,261 +238.8% |
| 2017 | $18,681 +234.3% | $333,000 |
| 2016 | $5,589 -0.1% | $333,000 +32.1% |
| 2015 | $5,594 +24.4% | $252,000 -7.5% |
| 2014 | $4,496 +17.9% | $272,298 +25.1% |
| 2013 | $3,815 -8.7% | $217,657 -8% |
| 2012 | $4,179 -0.9% | $236,626 -0.6% |
| 2011 | $4,218 -6.2% | $237,943 -9.1% |
| 2010 | $4,495 | $261,676 -11.2% |
| 2009 | -- | $294,623 -12.1% |
| 2008 | $4,438 -1.2% | $335,176 -5.5% |
| 2007 | $4,492 -6.5% | $354,747 +1.9% |
| 2006 | $4,804 0% | $348,148 +22.1% |
| 2005 | $4,805 +13.3% | $285,032 +22.7% |
| 2004 | $4,242 +15.1% | $232,386 +11.3% |
| 2003 | $3,685 +19.3% | $208,788 +19.2% |
| 2002 | $3,089 +2.1% | $175,137 +3.5% |
| 2001 | $3,025 +19.3% | $169,251 +20.3% |
| 2000 | $2,536 | $140,681 |
Find assessor info on the county website
Neighborhood: 32789
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Nearby schools
GreatSchools rating
- 10/10AUDUBON PARK SCHOOLGrades: PK-8Distance: 0.8 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 1.5 mi
Schools provided by the listing agent
- Elementary: Audubon Park K8
- Middle: Audubon Park K-8
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$3,000,500
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Estimated market value
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- Florida
- Orange County
- Winter Park
- 32789
- 2040 Randall Cir
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