305 Gilbert Rd, Winter Park, FL 32792
OFF MARKET

305 Gilbert Rd
Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,031 sqft

$712,200

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $4,877/mo*
Refinance Your Home

$712,200

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $4,877/mo*
Refinance Your Home
4 Beds
2 Baths
2,031 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Nestled in the highly sought-after neighborhood of WINTER PARK PINES, you'll find this beautifully maintained and UPDATED 4-bedroom, 2-bath home. This 2031 sq ft residence has a thoughtful layout with three spacious and flexible living spaces for dining, entertaining and family time. A dedicated office space provides ample space for both relaxation and productivity. You'll appreciate the peace of mind with a BRAND-NEW ROOF installed in June 2024. Crown molding adds a touch of sophistication, enhancing the charm of the interior spaces. Step into the heart of the home where a newly remodeled kitchen awaits, featuring granite countertops and ample, sleek bottom cabinetry in warm tones, complemented by cream-toned upper wood cabinets equipped with three lazy susans, pull-outs, and plenty of pantry storage. Enjoy family meals at the breakfast bar or in the adjacent dining room, ideal for both cozy dinners and entertaining larger groups With four bedrooms, there's ample space for everyone to spread out! Retreat to your primary bedroom suite for comfort and privacy which features a modern and stylish en suite bath. All around the house, tile and luxury vinyl flooring boost style while making upkeep a breeze. This property includes a practical two-car garage and opens up to a delightful backyard with a patio, offering plenty of space for outdoor activities and entertaining. The generous yard also provides room for a pool, perfect for creating your own private retreat. Located in Winter Park Pines, known for its tranquil atmosphere and proximity to excellent schools, Park Avenue, shopping, restaurants, Cady Way Park and Trail, and numerous other parks and churches this home offers a blend of comfort, convenience, and modern elegance. Don't miss the opportunity to make this meticulously updated residence your own. Schedule your showing today and envision the possibilities of calling this house your new home.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from April 08, 2026

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio
View
No Info
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 305 Gilbert Rd

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Bedroom 3, Primary Bathroom, Bathroom 1, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2
Dimensions and Layout
Living Area: 2031 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Available, Public, Water ConnectedAppliances: Cooktop, Dishwasher, Disposal, Electric Water HeaterDishwasherDisposalLaundry: In Garage
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Luxury Vinyl, Tile
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Luxury Vinyl, Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, PatioFencing: Fenced, Vinyl, WoodVegetation: Mature Landscaping, Oak Trees, Trees/LandscapedOther Structures: Shed(s)Exterior: Lighting, Private Mailbox, Rain Gutters, Sidewalk, StorageFoundation: SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Off Street,Workshop in Garage
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 20

Property Information

Year Built
Year Built: 1964
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Florida
Building
Construction Materials: BlockNot a New ConstructionNot Attached PropertyNo Additional Parcels
Property Information
Parcel Number: 092230942705120

Price & Status

Price
List Price: $650,000
Status Change & Dates
Off Market Date: Thu Jul 18 2024

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: WINTER PARK PINES
School Information
Elementary School: Brookshire ElemJr High / Middle School: Glenridge MiddleHigh School: Winter Park High

Building

Building Area
Building Area: 2608 Square Feet

Community

Community Features: Playground, Pool, Sidewalks, Tennis Court(s)Not Senior Community
Other
Playground

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 8881 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, FHA, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6218798Showing Requirements: Appointment Only, Lockbox - Electronic, ShowingTimeUniversal Property Id: US-12095-N-092230942705120-R-N

Additional Information

PlaygroundPoolSidewalksTennis Court(s)
Last check for updates: about 7 hours ago
Listed by Jeanne McKnight, (407) 319-3751
LPT REALTY, LLC, (877) 366-2213
Bought with: Juan Ortega, DREAM LIFE REALTY, (786) 534-6877
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6218798
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 305 Gilbert Rd

DatePriceEventSource
09/04/2024$650,000Sold
Stellar MLS #O6218798
06/28/2024$650,000Listed For SaleStellar MLS #O6218798

Market trends in Winter Park

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$457K
$833MoM
Sale-to-List Price
97.0%
0.3%MoM
Price per sq ft
$284
$4MoM
Available listings
363
1MoM
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Property Tax and Assessment

Year2024
Tax$2,465
Assessment$525,764
Home facts updated by county records

Comparable Sales for 305 Gilbert Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2814 Sheriff Way, Winter Park, FL
0.10
Single-Family Home
$545,000
04/22/26
4
2
1,948
402 Saint Dunstan Way, Winter Park, FL
0.15
Single-Family Home
$656,402
09/05/25
3
2
1,779
2707 Prince John Rd, Winter Park, FL
0.10
Single-Family Home
$630,000
06/18/25
3
2
1,670
2823 Cady Way, Winter Park, FL
0.14
Single-Family Home
$439,000
07/17/25
4
2
1,688
2855 Lion Heart Rd, Winter Park, FL
0.22
Single-Family Home
$620,000
07/21/25
3
2
1,727
2833 Prince John Rd, Winter Park, FL
0.16
Single-Family Home
$400,000
02/13/26
4
2
1,605
2817 Prince John Rd, Winter Park, FL
0.13
Single-Family Home
$665,000
06/18/25
4
3.5
2,183
2708 Lion Heart Rd, Winter Park, FL
0.11
Single-Family Home
$435,000
12/11/25
3
2
1,785
2748 Lion Heart Rd, Winter Park, FL
0.11
Single-Family Home
$475,000
03/16/26
3
2
1,502
2831 Lion Heart Rd, Winter Park, FL
0.19
Single-Family Home
$460,000
12/05/25
3
2
1,978

Nearby homes

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Assigned Schools

These are the assigned schools for 305 Gilbert Rd.
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 Winter Park

At least 594 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 85 % Say car is needed

  • 84 % Say there are sidewalks

  • 79 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
    Flag
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
    Flag
  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
    Flag
  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
    Flag
  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
    Flag
  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
    Flag
  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
    Flag
  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
    Flag
  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
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  • Oviedohome
    "Need to drive to work. Can walk to local parks. Walking or biking other places does not feel so friendly even though there are restaurants and grocery stores nearby. There are two commuter train stations close by. "
    2
    Flag

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305 Gilbert Rd, Winter Park, FL 32792 is a 4 bedroom, 2 bathroom, 2,031 sqft single-family home built in 1964. This property is not currently available for sale. 305 Gilbert Rd was last sold on Sep 4, 2024 for $650,000 (0% higher than the asking price of $650,000). The current Trulia Estimate for 305 Gilbert Rd is $712,200.