Off Market Jul 2024 for $925K

$1,118,349

Est. refi paymentEst. refi $4,679/mo

•

2,692

sq ft

1355 Pelham Rd, Winter Park, FL 32789

About this home

Step back in time while indulging in contemporary comforts with this exquisite historic property boasting 3 bedrooms, 3 full baths, and 1 half bath. Take a dip in the luxurious inground swimming pool featuring a lavish Jacuzzi hot tub and a beautiful travertine deck surround. Elegant hardwood floors flow throughout the main areas of this home and stylish wood work is abundant throughout. Channel your inner chef in the fully remodeled gourmet kitchen equipped with gorgeous granite countertops, large eat-in island, stainless steel appliances, gas cook top, and ample storage space. Whether preparing a casual meal or hosting a dinner party, this kitchen is sure to inspire culinary creativity. Situated just minutes from downtown Winter Park and Orlando, this property offers unparalleled access to cultural landmarks, upscale dining establishments, boutique shops, and vibrant entertainment venues. Immerse yourself in the rich tapestry of history and culture while enjoying the convenience of modern urban living. Roof, HVAC, electrical, and plumbing were all replaced in 2016 during a renovation/addition. An inground swimming pool equipped with a Pentair automation package, led lighting, deck & spa jets, added in 2020. A 600 sq-ft guest-house/pool cabana was also added in 2021. Too many other upgrades to list. The Orwin Manor development dates back to the mid-1800’ and is located at the intersection of Orlando and Winter Park, hence the name "Orwin". Along with the residents, the convenient location, variety of architecture with many historic homes, mature street tree landscape and caring neighbors are what makes Orwin Manor such a great place to live. Come see this classic Orwin Manor upgraded historic home. To learn more about the history of Orwin Manor, visit https://orwinmanor.org/history/#_

Single-familyProperty Type

1926Year Built

6,750 sq ftLot Size

$415Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Anthony Smith • SILVERLEAF REALTY GROUP

Contact: 786-348-0096

Bought with Beth Hobart • MAINFRAME REAL ESTATE

Redfin checked: 2 minutes ago

•Source:Stellar MLS as Distributed by MLS Grid #O6209454

Redfin Estimate

$1,118,349

$193K since sold in July 2024$40K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.8% higher than the average sale price ($1.03M) of 6 comparable homes.

SOLD JUL 2, 2026
$595,000
A
4 beds4 baths2,433 sq ft
2 W Steele St, Orlando, FL 32804
SOLD JUN 23, 2026
$1,125,000
B
3 beds2.5 baths2,426 sq ft
1651 Westchester Ave, Winter Park, FL 32789
SOLD SEP 4, 2026
$647,500
C
3 beds2.5 baths1,389 sq ft
913 Camellia Ave, Winter Park, FL 32789
SOLD AUG 31, 2026
$2,300,000
D
3 beds3.5 baths3,750 sq ft
3041 Westchester Ave, Orlando, FL 32803
SOLD SEP 1, 2026
$730,000
E
4 beds3 baths2,155 sq ft
950 S Kentucky Ave, Winter Park, FL 32789
SOLD OCT 23, 2025
$771,000
F
3 beds2 baths2,042 sq ft
1340 Pelham Rd, Winter Park, FL 32789

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$342,071

Est. take-home

List your home with Redfin and save $11,183

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$3,462/mo

Redfin rental estimate

List your home for rent

Market trends in 32789, FL

Last updated August 2026

Buyer's Market

Seller's Market

Balanced market

Sale-to-List Price

96.3%

+0.2% MoM

Median sale price

$1.0M

$135K MoM

Avg. days on market

46d

10 days MoM

Recently sold homes

147

6 MoM

New listings for sale

OPEN SAT, 2PM TO 4PM
$2,195,000
4 beds4.5 baths2,850 sq ft
1271 Palmer Ave, Winter Park, FL 32789
NEW 3 HRS AGO
$1,300,000
3 beds2.5 baths2,563 sq ft
504 W Swoope Ave, Winter Park, FL 32789
NEW 18 HRS AGO
$960,000
2 beds1 bath1,290 sq ft
447 N Phelps Ave, Winter Park, FL 32789
NEW 26 HRS AGO
$950,000
3 beds2 baths1,887 sq ft
913 Moss Ln, Winter Park, FL 32789
NEW 26 HRS AGO
$2,190,000
4 beds3 baths3,463 sq ft
1803 Barker Dr, Winter Park, FL 32789
$1,095,000
4 beds3 baths2,803 sq ft
443 Broadview Ave, Winter Park, FL 32789
VIDEO TOUR
$4,400,000
4 beds5.5 baths3,720 sq ft
702 Via Bella, Winter Park, FL 32789
$3,950,000
4 beds2 baths1,652 sq ft
540 N Pennsylvania Ave, Winter Park, FL 32789
3D & VIDEO TOUR
$2,475,000
3 beds3 baths2,316 sq ft
311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
COMING SOON
$965,000
3 beds2.5 baths1,957 sq ft
1256 S Pennsylvania Ave #9, Winter Park, FL 32789
See all

Provided by Redfin

Sale history for 1355 Pelham Rd

Date

Event

Price

Stellar MLS as Distributed by MLS Grid #O6209454

Jul 10, 2024

Sold

$925,000

$344/sq ft

Jun 7, 2024

Pending

—

May 29, 2024

Listed

$950,000

$353/sq ft

Stellar MLS as Distributed by MLS Grid #O5131743

Feb 4, 2013

Sold

$299,000

$111/sq ft

Nov 27, 2012

Listed

$325,000

$121/sq ft

The finest 1926 bungalow in Orwin Manor. Swing on the covered front porch, snuggle in front of fireplace, or entertain on the large back deck, this home is a charmer! All 3 bedrooms and a full bathroom with a tub are upstairs. In addition, the "sleeping porch" has been converted into an office/media/play room. Beautiful original hardwood floors and thick crown/floor/window molding are throughout the entire home. The renovated kitchen includes updated cabinets, stone counters and stainless steel appliances with a gas cooking range. Plenty of room for an island or a dinette area for an eat-in kitchen. The indoor utility room (5x8) includes additional cabinets for kitchen storage and pantry. Plus, Washer and Dryer STAY, only 3 years new. Never run out of hot water with the tankless-gas hot water heater. 2 AC units, one for upstairs and downstairs, are serviced on a regular basis. The exterior of the home was restored and repainted in 2012. The outdoor shed (16x19), once a horse carriage, includes electricity is currently used as a tool and storage room. This would be great to convert into a pool cabana for your future pool. Plenty of room to add a pool, add on 800 sqft, or convert the outdoor shed to a guest house! Come see this classic Orwin Manor bungalow.

Public Records

Jan 20, 2004

Sold

$265,000

$98/sq ft

Public Records

Jul 20, 1999

Sold

$195,000

$72/sq ft

Public Records

Oct 1, 1993

Sold

$160,000

$59/sq ft

Tax history for 1355 Pelham Rd

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

6,750 Sq. Ft.

Year renovated

1999

Sq. Ft.

2,092

Year built

1925

Style

Single Family Residential

County

Orange County

APN

292212643202060

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Aug 17, 2026.

R-1A \N

Residential District

These districts are established within the city to provide areas for single-family dwellings and necessary accessory buildings. The regulations enumerated for this district are designed to encourage and promote the construction of and the continued use of the land for single-family dwellings, to promote and encourage a suitable environment for family life, to prohibit uses of the land which would substantially interfere with development or continuation of single-family dwellings in the districts, and to prevent use of the land for purposes which would overburden the public facilities. Permitted as conditional uses within these districts will be certain structures and uses required to serve the residents such as public schools, churches and noncommercial recreational uses. Areas zoned for R-1A districts shall be those existing low-density residential areas plus certain undeveloped areas which should develop in a similar manner according to the comprehensive plan.

Permitted uses

Include but are not limited to:

Housing-Single unit

Property details

Parking

Parking Information
Parking Features: Covered, Driveway
Garage Spaces: 1
Has Carport
Carport Spaces: 1
Has Garage

Interior

Virtual Tour

Bedroom Information
# of Bedrooms: 3

Bathroom Information
# of Full Baths (Total): 3
# of Half Baths (Total): 1

Laundry Room Information
Laundry Features: Inside

Other Rooms Information
Additional Rooms: Attic,Family Room,Formal Dining Room Separate,Formal Living Room Separate,Inside Utility,Interior In-Law Suite w/Private Entry,Storage Rooms
# of Rooms: 12

Fireplace Information
Has Fireplace
Fireplace Features: Family Room, Wood Burning

Heating & Cooling
Heating Information: Central
Cooling Information: Central Air

Interior Features
Interior Features: Ceiling Fans(s), Crown Molding, Eat-in Kitchen, Open Floorplan, Skylight(s), Solid Wood Cabinets, Stone Counters, Vaulted Ceiling(s), Walk-in Closet(s)
Window Features: Blinds, ENERGY STAR Qualified Windows
Appliances: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Washer
Flooring: Wood

Exterior

Building Information
Construction Materials: Wood Frame
Roof: Shingle

Exterior Features
Patio And Porch Features: Covered, Deck, Patio, Porch
Exterior Features: French Doors, Irrigation System, Lighting, Sliding Doors

Pool Information
Pool Dimensions: 14x30
Spa Features: Heated, In Ground
Has Private Pool
Pool Features: In Ground, Lighting
Has Spa

Property Features
Universal Property Id: US-12095-N-122229643202060-R-N

Waterfront Information
Waterfront Feet Total: 0
Water View Y/N: 0
Water Access Y/N: 0
Water Extras Y/N: 0

Property Information
CDD Y/N: 0
Homestead Y/N: 1
Property Type: Residential
Property Sub Type: Single Family Residence
Other Structures: Cabana, Guest House
Zoning: R-1A

Land Information
Vegetation: Mature Landscaping, Trees/Landscaped
Future Land Use: 0100
Total Acreage: 0 to less than 1/4

Lot Information
Lot Features: City Limits, Sidewalk, Paved, Private
Lot Size Acres: 0.15
Lot Size Dimensions: 50x135
Road Surface Type: Asphalt
Lot Size Square Meters: 627
Zoning Compatible YN: 1
Other Exemptions YN: 0

Building Information
MFR_BuildingAreaTotalSrchSqM: 355.54

Financial

Tax Information
Tax Annual Amount: $5,686
Tax Year: 2023

Lease / Rent Details
Lease Restrictions YN: 0

Utilities

Utility Information
Water Source: Public
Sewer: Public Sewer
Utilities: Cable Available, Electricity Connected, Public

Location

Multi-Family Financial Information
Total Annual Fees: $35
Total Monthly Fees: $2.92

Multi-Unit Information
Unit Number YN: 0

HOA Information
Has HOA
MFR_Association2YN: 0
Association Fee Requirement: Optional
Association Approval Required Y/N: 0
Monthly HOA Amount: 2.92
Association Amenities: Playground
Association Fee: $35
Association Fee Frequency: Annually

School Information
Elementary School: Killarney Elem
Middle Or Junior High School: College Park Middle
High School: Edgewater High

Location Information
Directions: From Fairbanks or 17-92, Go WEST on Orange Ave., Then RIGHT on Westchester, then RIGHT on Pelham. Home is half way down on left.

Community Information
Community Features: Park, Playground
Pets Allowed: Yes

Public facts

Beds: 3
Baths: 2.0
Sq. Ft.: 2,092
Stories: 2.0
Lot Size: 6,750 square feet
Style: Single Family Residential
Year Built: 1925
Year Renovated: 1999
County: Orange County
APN: 292212643202060

Home facts updated by county records on Aug 17, 2026

Other

Miscellaneous Information
Third Party YN: 1

Listing Information
Attribution Contact: 786-348-0096
Previous Status: Pending
Backups Requested YN: 0
Home Warranty YN: No

Listing Date Information
Days to Contract: 8
Status Contractual Search Date: 2024-07-10

Listing Price Information
Calculated List Price By Calculated Sq Ft: 352.90

Green Information
Green Verification Count: 0
Direction Faces: East

Home Information
Living Area: 2692
Living Area Units: Square Feet
Living Area Source: Owner
Living Area Meters: 250.09
Building Area Total: 3827
Building Area Units: Square Feet
Building Area Source: Owner
Foundation Details: Crawlspace, Stem Wall
Levels: Two
Security Features: Security System Owned, Smoke Detector(s)

Around this home

Schools

Killarney Elementary School

Public PreK-5 • Assigned • 1.0mi

4/10

College Park Middle School

Public 6-8 • Assigned • 1.6mi

3/10

Edgewater High School

Public 9-12 • Assigned • 1.4mi

6/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

9/10 Heat Factor

7 days above 107° expected this year, 22 days in 30 years

9/10 Wind Factor

99% chance of strong winds in next 30 years

2/10 Air Factor

0 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

Historical weather

Winter Park, FL • 32789

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.6 hours in June and 6.7 hours in December, placing it above the U.S. average for solar exposure.

8.6 hrs

6.7 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.06M – $1.29M

Reach more buyers when you sell with Redfin. Save up to $11,183 in fees. 3 minutes to get started.

Need the cash from your home fast? Sell to .

Nearby similar homes

OPEN SUN, 12PM TO 2PMVIDEO TOUR

$1,250,000

3 beds3.5 baths2,273 sq ft

1707 Asher Ln, Orlando, FL 32803

$4,250,000

4 beds5 baths4,431 sq ft

229 Alexander Pl, Winter Park, FL 32789

$619,000

3 beds2 baths1,722 sq ft

317 W King St, Orlando, FL 32804

$1,100,000

5 beds3 baths3,000 sq ft

533 W Yale St, Orlando, FL 32804

NEW CONSTRUCTION

$2,299,000

5 beds5 baths2,868 sq ft

1840 Laurel Rd, Winter Park, FL 32789

NEW CONSTRUCTION

$3,199,000

4 beds4.5 baths3,737 sq ft

361 E Kings Way, Winter Park, FL 32789

New listings for sale in 32789

OPEN SAT, 2PM TO 4PMVIDEO TOUR

$2,195,000

4 beds4.5 baths2,850 sq ft

1271 Palmer Ave, Winter Park, FL 32789

NEW 3 HRS AGO

$1,300,000

3 beds2.5 baths2,563 sq ft

504 W Swoope Ave, Winter Park, FL 32789

NEW 18 HRS AGO

$960,000

2 beds1 bath1,290 sq ft

447 N Phelps Ave, Winter Park, FL 32789

NEW 26 HRS AGOVIDEO TOUR

$950,000

3 beds2 baths1,887 sq ft

913 Moss Ln, Winter Park, FL 32789

NEW 26 HRS AGO

$2,190,000

4 beds3 baths3,463 sq ft

1803 Barker Dr, Winter Park, FL 32789

$1,095,000

4 beds3 baths2,803 sq ft

443 Broadview Ave, Winter Park, FL 32789

VIDEO TOUR

$4,400,000

4 beds5.5 baths3,720 sq ft

702 Via Bella, Winter Park, FL 32789

$3,950,000

4 beds2 baths1,652 sq ft

540 N Pennsylvania Ave, Winter Park, FL 32789

3D & VIDEO TOUR

$2,475,000

3 beds3 baths2,316 sq ft

311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

Home values near 1355 Pelham Rd

Data from public records.

Address	Redfin Estimate
1400 Pelham Road, Winter Park, FL 2 Beds \| 2 Baths \| 1298 Sq. Ft.	$468,285
1340 Pelham Road, Winter Park, FL 3 Beds \| 2 Baths \| 2042 Sq. Ft.	$849,499

Address	Redfin Estimate
1406 Pelham Road, Winter Park, FL 2 Beds \| 1 Baths \| 1660 Sq. Ft.	$581,872
1300 Pelham Road, Winter Park, FL 3 Beds \| 1 Baths \| 1247 Sq. Ft.	$552,529

Address	Redfin Estimate
1330 Pelham Road, Winter Park, FL 2 Beds \| 1 Baths \| 1198 Sq. Ft.	$382,421
1320 Pelham Road, Winter Park, FL 2 Beds \| 2 Baths \| 1125 Sq. Ft.	$437,046

Property information provided by Stellar MLS as Distributed by MLS Grid when last listed in 2024. This data may not match . Learn more.

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Audubon Park homes for sale
College Park homes for sale
Winter Park Pines homes for sale
Baldwin Park homes for sale
Orwin Manor homes for sale

32803 homes for sale
32804 homes for sale
32789 homes for sale
32792 homes for sale
32751 homes for sale

Houses for rent in Winter Park	Agents near me	Sarasota, FL homes for sale	Winter Park Housing Market
Houses for sale near me	Orlando, FL homes for sale	Fort Lauderdale, FL homes for sale
Land for sale near me	Tampa, FL homes for sale	Boca Raton, FL homes for sale
Open Houses near me	Miami, FL homes for sale	Winter Park Property Records
Condos for sale near me	Jacksonville, FL homes for sale	FL New Listings

Orlando homes for sale
Kissimmee homes for sale
Winter Garden homes for sale

About this home

Redfin Estimate

Earn from this home

Market trends in 32789, FL

Sale history for 1355 Pelham Rd

Tax history for 1355 Pelham Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 32789

Home values near 1355 Pelham Rd

More real estate resources