EasyStreet Realty
REALTOR ®
(407) 485-1814
Email Sherri
mobile navigation links

2739 Riddle Dr, Winter Park, FL 32789

PENDING $650,000
Charming single-Gathering home with a modern design and well-manicured lawn, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789

  • Bedrooms

    4

  • Baths

    3

  • Sq. Feet

    1881

  • Year Built

    2023

  • Days On Market

    61

  • $/SqFt

    $346

Message Agent
Schedule Tour

45 Photos

  • Charming single-Gathering home with a modern design and well-manicured lawn, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789
  • Charming single-Gathering home with a modern design and well-manicured lawn, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789
  • Single Gathering home with a modern design, complemented by a two-car garage, and fenced yard at 2739 Riddle Dr, Winter Park, FL 32789
  • Close up of a front door of single Gathering home with a modern design, complemented by a two-car garage at 2739 Riddle Dr, Winter Park, FL 32789
  • Bright foyer with tile floors, staircase, and modern decor offers a welcoming entrance at 2739 Riddle Dr, Winter Park, FL 32789
  • Modern kitchen with white cabinets, a central island with bar stools, and stylish pendant lighting at 2739 Riddle Dr, Winter Park, FL 32789
  • Modern kitchen featuring sleek white cabinetry, stainless steel appliances, and a large island at 2739 Riddle Dr, Winter Park, FL 32789
  • Open-concept kitchen featuring a large island, stainless steel appliances, and seamless flow to the living area at 2739 Riddle Dr, Winter Park, FL 32789
  • Bright kitchen island with modern fixtures, open to the living area and staircase at 2739 Riddle Dr, Winter Park, FL 32789
  • Stylish living room with comfortable seating, modern decor, and sliding doors to the outdoor space at 2739 Riddle Dr, Winter Park, FL 32789
  • Open-concept living room featuring a gray sectional sofa and modern decor at 2739 Riddle Dr, Winter Park, FL 32789
  • Bright living room with a gray sectional sofa and access to the backyard at 2739 Riddle Dr, Winter Park, FL 32789
  • Spacious living room with a gray sectional sofa and natural light at 2739 Riddle Dr, Winter Park, FL 32789
  • Inviting living room with a gray sectional sofa and stylish decor at 2739 Riddle Dr, Winter Park, FL 32789
  • Functional home office with a desk, storage, and natural lighting at 2739 Riddle Dr, Winter Park, FL 32789
  • Organized home office with a large desk, drawers, and a window view at 2739 Riddle Dr, Winter Park, FL 32789
  • Chic powder room featuring a modern sink and stylish mirror at 2739 Riddle Dr, Winter Park, FL 32789
  • Clean and simple toilet in the bathroom at 2739 Riddle Dr, Winter Park, FL 32789
  • Calm main bedroom with a king-size bed and neutral colors at 2739 Riddle Dr, Winter Park, FL 32789
  • Spacious main bedroom with a king-size bed and modern decor at 2739 Riddle Dr, Winter Park, FL 32789
  • Spacious walk-in closet with built-in shelving and ample storage for clothes and accessories at 2739 Riddle Dr, Winter Park, FL 32789
More Photos \/
  • Walk-in closet featuring custom shelving and storage solutions for shoes and clothing at 2739 Riddle Dr, Winter Park, FL 32789
  • Modern bathroom with double vanity, sleek fixtures, and a glass-enclosed shower at 2739 Riddle Dr, Winter Park, FL 32789
  • Powder room featuring a toilet and blue painted walls at 2739 Riddle Dr, Winter Park, FL 32789
  • Bright bedroom with colorful bed, white walls and a window at 2739 Riddle Dr, Winter Park, FL 32789
  • Bedroom featuring a bed with dinosaur-themed bedspread, a television and a closet at 2739 Riddle Dr, Winter Park, FL 32789
  • Bathroom featuring a tub with shower curtain, a toilet and vanity with modern fixtures at 2739 Riddle Dr, Winter Park, FL 32789
  • Bedroom featuring a bed with a blue bedspread and a window at 2739 Riddle Dr, Winter Park, FL 32789
  • Bedroom featuring a bed with a blue bedspread, door and ceiling fan at 2739 Riddle Dr, Winter Park, FL 32789
  • Laundry room featuring modern washer and dryer with wooden countertop and storage cabinets at 2739 Riddle Dr, Winter Park, FL 32789
  • Spacious garage featuring a home gym with exercise equipment and black rubber flooring at 2739 Riddle Dr, Winter Park, FL 32789
  • Outdoor living space with pavers, ceiling fan, patio furniture, and outdoor fireplace at 2739 Riddle Dr, Winter Park, FL 32789
  • Covered outdoor patio with ample seating, lighting, ceiling fans and backyard view at 2739 Riddle Dr, Winter Park, FL 32789
  • Extended back patio showing outdoor living space, ceiling fans, and large backyard at 2739 Riddle Dr, Winter Park, FL 32789
  • Backyard shed with painted siding, steps and white door with window panels at 2739 Riddle Dr, Winter Park, FL 32789
  • View of the shed interior featuring wood framing and storage for tools and gear at 2739 Riddle Dr, Winter Park, FL 32789
  • View of backyard with a modern home, patio, pergola, and wood fence at 2739 Riddle Dr, Winter Park, FL 32789
  • View of the backyard showcasing the patio, modern home and new landscaping at 2739 Riddle Dr, Winter Park, FL 32789
  • Wide view of the large, grassy backyard, the modern home, patio and shed at 2739 Riddle Dr, Winter Park, FL 32789
  • Aerial view of the property showcasing a home, inground pool, outdoor living and large backyard at 2739 Riddle Dr, Winter Park, FL 32789
  • An aerial view shows a fenced yard, shed, pool, and solar panels in a residential neighborhood near the city at 2739 Riddle Dr, Winter Park, FL 32789
  • This aerial view shows the property's roof, fence, shed, and surrounding yard in a residential neighborhood at 2739 Riddle Dr, Winter Park, FL 32789
  • An aerial view shows the home, driveway, and walkway in a residential neighborhood at 2739 Riddle Dr, Winter Park, FL 32789
  • An aerial view shows a residential neighborhood near a lake and highway at 2739 Riddle Dr, Winter Park, FL 32789
  • An aerial view shows a residential neighborhood near a highway at 2739 Riddle Dr, Winter Park, FL 32789
Less Photos /\

Tour This Home

Wed
30 Apr
Thu
1 May
Fri
2 May
Sat
3 May
Sun
4 May
Mon
5 May
Tue
6 May
Schedule Tour

Home Description

Under contract-accepting backup offers. Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances. $64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on sliding doors, a storage shed, privacy fencing, upgraded switches and dimmers, and custom cabinetry. The laundry room includes a butcher block folding table for added convenience. With a 2023 roof, HVAC, electrical, and plumbing systems, this home is ready for immediate occupancy. Located just minutes from Park Avenue, offering a variety of shopping, dining, and entertainment options in Winter Park. Contact us today to schedule a showing!

  • Elementary School: Killarney Elem
  • Middle School: College Park Middle
  • High School: Edgewater High
  • Private Pool: False
  • Water Feet: 0
  • Interior Features: Ceiling Fans(s),Kitchen/Family Room Combo,Open Floorplan,Primary Bedroom Main Floor,Walk-In Closet(s)
  • Appliances: Dishwasher,Disposal,Range,Range Hood,Refrigerator
  • Floor Covering: Carpet,Ceramic Tile
  • Exterior Features: Private Mailbox,Sliding Doors,Storage
  • Exterior Contruction: Block,Stucco
  • Foundation: Slab
  • Front Exposure: West
  • Roof: Shingle
  • Building Sqft: 2361

Approximate Room Sizes / Descriptions

Bathroom 311.4x11SecondCarpet
Bathroom 411.4x11SecondCarpet
Great Room19x14FirstCeramic Tile
Kitchen14x15FirstCeramic Tile
Primary Bedroom15x13FirstCarpet
Bedroom 211.7x11FirstCarpet
  • Attached Garage: True
  • Garage: True
  • Garage Spaces: 2
  • Garage Feature: Driveway
  • Carport: False
  • Carport Spaces: 0
  • Air Conditioning: Central Air
  • Heating: Electric
  • Utilities: Cable Available,Electricity Available,Water Available
  • Lot Sqft: 10347.00
  • Lot Acres: 0.2400
  • Total Acre: 0 to less than 1/4
  • Lot Num: 15
  • Senior Community: False
  • Style: Single Family Residence
  • Building Num Floors: 2
  • : 813-922-2891

Neighborhood

The average asking price of a 4 bedroom Winter Park home in this zip code is $1,884,345 (189.9% more than this home).

This home is priced at $346/sqft, which is 66.5% less than similar homes in the 32789 zip code.

Map | Street | Birds Eye

Print Map | Driving Directions

Financial

  • Approx Payment:$3,162*
  • Taxes:$6,951

Area Stats

These statistics are updated daily from the My Florida Regional MLS. For further analysis or to obtain statistics not shown below please call EasyStreet Realty at (407) 485-1814 and speak with one of our real estate consultants.

Popular Homes

City
Avg Price
Median Price
Available
Distressed
Reduced
Avg DOM
Altamonte Springs
$513,557
$440,000
139
1.4%
44.6%
82

Apopka
$537,983
$479,450
546
1.6%
45.2%
91

Belle Isle
$849,856
$649,946
24
0.0%
54.2%
78

Casselberry
$443,549
$422,500
110
1.8%
43.6%
68

Celebration
$1,292,580
$1,004,500
50
0.0%
44.0%
94

Champions Gate
$687,769
$687,500
20
0.0%
45.0%
267

Chuluota
$933,720
$704,450
30
0.0%
30.0%
42

Clermont
$580,636
$495,000
746
0.5%
48.7%
80

Gotha
$1,016,028
$637,445
16
0.0%
50.0%
63

Groveland
$483,196
$404,000
259
1.9%
55.2%
86

Harmony
$446,991
$425,990
71
0.0%
31.0%
95

Kissimmee
$515,373
$445,000
2439
1.7%
48.1%
103

Longwood
$752,032
$555,950
222
1.4%
47.3%
70

Maitland
$903,610
$599,900
85
2.4%
55.3%
84

Minneola
$557,978
$534,990
133
0.8%
41.4%
82

Montverde
$1,521,942
$1,106,062
54
0.0%
42.6%
130

Ocoee
$532,828
$489,994
180
1.7%
52.2%
80

Orlando
$688,611
$499,900
3028
1.4%
48.9%
80

Oviedo
$729,751
$649,000
197
1.0%
43.1%
71

Poinciana
$327,407
$314,990
283
1.1%
55.1%
121

Reunion
$1,870,675
$1,125,000
107
0.9%
55.1%
162

Saint Cloud
$606,686
$465,430
181
1.1%
67.4%
209

Sanford
$527,388
$415,000
387
1.0%
51.7%
96

Sorrento
$608,052
$450,920
111
0.9%
48.6%
77

Windermere
$2,091,340
$1,299,000
293
0.3%
45.4%
98

Winter Garden
$858,138
$699,999
629
0.6%
48.2%
85

Winter Springs
$660,936
$510,000
142
0.7%
47.9%
72

Listing Courtesy of BRAINARD REALTY.

2739 Riddle Dr, Winter Park FL is a single family home of 1881 sqft and is currently priced at $650,000 . This single family home has 4 bedrooms. A comparable home for sale at 770 Carver St in Winter Park is listed at $365,000. In addition to single family homes, EasyStreet also makes it easy to find Homes, Condos, New Homes and Foreclosures in Winter Park, FL. Sylvan Heights, Temple Terrace and Lawndale are nearby neighborhoods. MLS TB8355970 has been posted on this site since 3/1/2025 (today).

2025 4/30/2025.

Message Agent

Send

Schedule a tour

2739 Riddle Dr Winter Park FL 32789

Choose a day and time

You Requested

We'll be in touch shortly to confirm your tour time and other details. Please let us know how to reach you.

Schedule Tour

CLOSE

Your message has been sent!

The agent will be in touch with you in just a minute.