Homes in ZIP Code 32789

/13
$1,250,000
- 4 Beds
- 1 Bath
- 1,260 Sq Ft
230 Killarney Dr, Winter Park, FL 32789

Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just

Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

230 Killarney Dr, Winter Park, FL 32789
/2
$4,500,000

Sold May 29, 2026

1521 Harris Cir, Winter Park, FL 32789
- 4 Beds
- 4.5 Baths
- 3,922 Sq Ft
- Built 2026
Last Sold Summary
- $1,147/SF
- 0 Days On Market
Current Estimated Value $3,635,666

Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

1521 Harris Cir, Winter Park, FL 32789

/2
Est $125,492

Not Listed For Sale

1695 Lee Rd Unit D206, Winter Park, FL 32789
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Built 1966
1695 Lee Rd Unit D206, Winter Park, FL 32789

Last Sold Summary
- 271 Days On Market
Last Listing Agent Justin Adams EXP REALTY LLC

/51
$1,100,000
- 3 Beds
- 2.5 Baths
- 2,196 Sq Ft
2227 Howard Dr, Winter Park, FL 32789

A rare corner lot in one of Winter Park's most established, increasingly in-demand Lake Forest Park neighborhood. This mid-century home has been meticulously maintained. With beautiful hardwood floors and updated systems throughout, there's nothing left to do but move in.The lot is the story here. A stunning mature oak anchors the front yard, and the corner position with no north-facing

Julian Correa THE SIMON SIMAAN GROUP

2227 Howard Dr, Winter Park, FL 32789
/46
$840,000

Sold Sep 15, 2026

1405 Miller Ave, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 1,884 Sq Ft
- Built 2023
Last Sold Summary
- 12% Below List Price
- $446/SF
- 67 Days On Market
Current Estimated Value $883,640

Last Listing Agent Rikhil Amin FANNIE HILLMAN & ASSOCIATES

1405 Miller Ave, Winter Park, FL 32789

/2
Est $121,163

Not Listed For Sale

1695 Lee Rd Unit D205, Winter Park, FL 32789
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Built 1966
1695 Lee Rd Unit D205, Winter Park, FL 32789

Last Sold Summary
- 11 Days On Market
Last Listing Agent Martha Grasty EXP REALTY LLC

/39
$1,595,000

$100K PRICE DROP
- 4 Beds
- 2 Baths
- 2,640 Sq Ft
446 Melrose Ave, Winter Park, FL 32789

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with

Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

446 Melrose Ave, Winter Park, FL 32789
/2
$290,000

Sold Jul 15, 2026

184 Sandlewood Trail Unit 2, Winter Park, FL 32789
- 2 Beds
- 2.5 Baths
- 1,133 Sq Ft
- Built 1985
Last Sold Summary
- 12% Below List Price
- $256/SF
- 141 Days On Market
Current Estimated Value $286,351

Last Listing Agent Tom Noelke NOELKE REALTY

184 Sandlewood Trail Unit 2, Winter Park, FL 32789

/4
Est $115,986

Not Listed For Sale

1695 Lee Rd Unit D109, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 638 Sq Ft
- Built 1966
1695 Lee Rd Unit D109, Winter Park, FL 32789

Last Sold Summary
- 0 Days On Market
Last Listing Agent Erin Baker FANNIE HILLMAN & ASSOCIATES

/11
$4,650,000

New Construction
- 5 Beds
- 5.5 Baths
- 4,827 Sq Ft
857 Brock St, Winter Park, FL 32789

Under Construction. Designed to capture the timeless character of Olde Winter Park while delivering an extraordinary level of modern luxury, this is a truly one-of-a-kind residence by Vimaro Homes. Set within the highly sought-after Park Grove neighborhood and designed by renowned architect Gary Hancock, the home makes an unforgettable first impression with a stately front façade, manicured

Julie Christensen ONE LUXURY INTERNATIONAL LLC

857 Brock St, Winter Park, FL 32789
/2
$1,129,000

Sold Dec 10, 2025

100 S Virginia Ave Unit 314, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 2,615 Sq Ft
- Built 2009
Last Sold Summary
- $432/SF
- 4 Days On Market
Current Estimated Value $1,149,771

Last Listing Agent Julieta Knapp ACCUMARK PROPERTIES

100 S Virginia Ave Unit 314, Winter Park, FL 32789

/5
Est $112,995

Not Listed For Sale

1695 Lee Rd Unit C110, Winter Park, FL 32789
- 1 Bed
- 1 Bath
- 638 Sq Ft
- Built 1966
1695 Lee Rd Unit C110, Winter Park, FL 32789

Last Sold Summary
- 0 Days On Market
Last Listing Agent Martha Grasty EXP REALTY LLC

/58
$1,295,000

$55K PRICE DROP
- 3 Beds
- 4 Baths
- 2,191 Sq Ft
720 Pansy Ave, Winter Park, FL 32789

Welcome to 720 Pansy Ave, a distinctive three-story Winter Park home thoughtfully designed for both everyday living and flexible use. Fully remodeled in 2017, the residence offers a clean, contemporary interior with LVP and tile flooring, recessed lighting, crisp finishes, and an open flow through the main living spaces. The first floor includes a spacious living room, dining area, and a separate

Nickolas McKee KELLER WILLIAMS WINTER PARK

720 Pansy Ave, Winter Park, FL 32789
/2
$1,420,000

Sold Sep 18, 2026

607 Ellen Dr, Winter Park, FL 32789
- 4 Beds
- 5 Baths
- 2,812 Sq Ft
- Built 2025
Last Sold Summary
- 13% Below List Price
- $505/SF
- 294 Days On Market
Current Estimated Value $1,166,306

Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

607 Ellen Dr, Winter Park, FL 32789

/25
Est $128,953

Not Listed For Sale

1695 Lee Rd Unit B114, Winter Park, FL 32789
- 2 Beds
- 1 Bath
- 881 Sq Ft
- Built 1966
1695 Lee Rd Unit B114, Winter Park, FL 32789

Last Sold Summary
- 68 Days On Market
Last Listing Agent Martha Grasty EXP REALTY LLC

/2
$599,999
- Land
- 10,890 Sq Ft
- $2,399,996 per Acre
822 Symonds Ave, Winter Park, FL 32789

Build in the heart of Winter Park. This cleared quarter-acre lot (approx. 10,807 sq ft, 50' x 216') sits on Symonds Avenue on the city's west side. It's just blocks from Hannibal Square, Winter Park Village and Martin Luther King Jr. Park, and minutes from the shops and restaurants of Park Avenue.The lot is ready for your plans. It's cleared, with mature shade trees, a paved street with

David Glinski NEWBERRY REALTY & DEV GRP INC.

822 Symonds Ave, Winter Park, FL 32789
/2
$2,280,000

Sold Jun 08, 2026

436 N Knowles Ave, Winter Park, FL 32789
- Land
- 11,325 Sq Ft
- $8,769,231 per Acre
Last Sold Summary
- 7% Below List Price
- 0 Days On Market
Current Estimated Value $1,779,843

Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

436 N Knowles Ave, Winter Park, FL 32789

/27
Est $179,167

Not Listed For Sale

1695 Lee Rd Unit A115, Winter Park, FL 32789
- 3 Beds
- 2 Baths
- 1,149 Sq Ft
- Built 1966
1695 Lee Rd Unit A115, Winter Park, FL 32789

Last Sold Summary
- 167 Days On Market
Last Listing Agent Justin Adams EXP REALTY LLC

/38
$2,350,000

Pending
- 3 Beds
- 3 Baths
- 2,143 Sq Ft
140 E Morse Blvd Unit J, Winter Park, FL 32789

Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining,

Mick Night PREMIER SOTHEBY'S INTL. REALTY

140 E Morse Blvd Unit J, Winter Park, FL 32789
/2
$350,000

Sold Jul 01, 2026

2002 Indiana Ave, Winter Park, FL 32789
- Land
- 6,969 Sq Ft
- $2,187,500 per Acre
Last Sold Summary
- 2% Below List Price
- 125 Days On Market
Current Estimated Value $383,333

Last Listing Agent David Nicholson DAWN REALTY

2002 Indiana Ave, Winter Park, FL 32789

/2
Est $248,568

Not Listed For Sale

1500 Gay Rd Unit 8B, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,026 Sq Ft
- Built 1972
1500 Gay Rd Unit 8B, Winter Park, FL 32789

Last Sold Summary
- 16 Days On Market
Last Listing Agent Marci Blanchard KELLER WILLIAMS ADVANTAGE REALTY

/35
$999,000

Open Sat 11AM - 2PM $51K PRICE DROP
- 3 Beds
- 3 Baths
- 2,434 Sq Ft
1138 S Pennsylvania Ave, Winter Park, FL 32789

Georgetown-style 'Brownstown' in the Heart of Winter Park, walking distance to Downtown, PLUS deeded Lake Access to Lake Virginia! FRESHLY PAINTED interior in 'Alabaster' 9/16-18/26! This spacious property has 3 bedrooms, 3 full baths, 2434 sq ft, 10' ceilings custom details throughout and natural lighting. Foyer with slate flooring, enjoy the double-sided gas fireplace in the Living & Dining

George Stringer COLDWELL BANKER REALTY

1138 S Pennsylvania Ave, Winter Park, FL 32789
/2
$1,770,000

Sold Sep 22, 2025

690 Williams Dr, Winter Park, FL 32789
- 3 Beds
- 4 Baths
- 3,121 Sq Ft
- Built 1962
Last Sold Summary
- 2% Below List Price
- $567/SF
- 0 Days On Market
Current Estimated Value $1,846,618

Last Listing Agent Tiffany Grindstaff KELLY PRICE & COMPANY LLC

690 Williams Dr, Winter Park, FL 32789

/2
Est $1,924,642

Not Listed For Sale

1764 Elizabeths Walk, Winter Park, FL 32789
- 4 Beds
- 4 Baths
- 3,989 Sq Ft
- Built 2012
1764 Elizabeths Walk, Winter Park, FL 32789

Last Sold Summary
- 159 Days On Market
Last Listing Agent Matt McKee COMPASS FLORIDA LLC

/28
$107,000

$8K PRICE DROP
- 2 Beds
- 1 Bath
- 881 Sq Ft
1695 Lee Rd Unit D211, Winter Park, FL 32789

Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

Brandy Ray LOKATION

1695 Lee Rd Unit D211, Winter Park, FL 32789
/2
$595,000

Sold Sep 10, 2026

531 W Swoope Ave, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,188 Sq Ft
- Built 2006
Last Sold Summary
- 6% Below List Price
- $501/SF
- 7 Days On Market
Current Estimated Value $623,164

Last Listing Agent Roger Soderstrom Jr. STIRLING INTERNATIONAL REAL ES

531 W Swoope Ave, Winter Park, FL 32789

/35
Est $244,073

Not Listed For Sale

215 Sandlewood Trail Unit 7, Winter Park, FL 32789
- 2 Beds
- 2.5 Baths
- 960 Sq Ft
- Built 1986
215 Sandlewood Trail Unit 7, Winter Park, FL 32789

Last Sold Summary
- 5 Days On Market
Last Listing Agent Pam Grabenhorst THE WILKINS WAY LLC

/65
$1,399,000

New Construction $151K PRICE DROP
- 5 Beds
- 4 Baths
- 3,164 Sq Ft
1523 Miller Ave, Winter Park, FL 32789

BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. 2-year builders' warranty! This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped

Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

1523 Miller Ave, Winter Park, FL 32789
/2
$1,350,000

Sold Aug 31, 2026

1560 Lakehurst Ave, Winter Park, FL 32789
- Land
- 13,503 Sq Ft
- $4,354,839 per Acre
Last Sold Summary
- 12% Above List Price
- 514 Days On Market
Current Estimated Value $1,108,859

Last Listing Agent Dawn Romance FANNIE HILLMAN & ASSOCIATES

1560 Lakehurst Ave, Winter Park, FL 32789

/2
Est $254,780

Not Listed For Sale

311 Sandlewood Trail Unit 4, Winter Park, FL 32789
- 2 Beds
- 2.5 Baths
- 980 Sq Ft
- Built 1984
311 Sandlewood Trail Unit 4, Winter Park, FL 32789

Last Sold Summary
- 5 Days On Market
Last Listing Agent Mario Zendeli COMPASS FLORIDA LLC

/30
$699,000
- 3 Beds
- 2 Baths
- 1,350 Sq Ft
250 Carolina Ave Unit 202, Winter Park, FL 32789

Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan.The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for

Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

250 Carolina Ave Unit 202, Winter Park, FL 32789
/2
$1,425,000

Sold May 19, 2026

850 Juanita Rael, Winter Park, FL 32789
- 4 Beds
- 3 Baths
- 2,306 Sq Ft
- Built 1966
Last Sold Summary
- $618/SF
- 4 Days On Market
Current Estimated Value $1,428,640

Last Listing Agent Brad Grosberg PHIL KEAN REAL ESTATE LLC

850 Juanita Rael, Winter Park, FL 32789

/2
Est $572,030

Not Listed For Sale

777 S Denning Dr Unit B, Winter Park, FL 32789
- 3 Beds
- 3 Baths
- 1,762 Sq Ft
- Built 2004
777 S Denning Dr Unit B, Winter Park, FL 32789

Last Sold Summary
- 37 Days On Market
Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK

/21
$1,449,000

$46K PRICE DROP
- Land
- 12,632 Sq Ft
- $4,996,552 per Acre
150 E Reading Way, Winter Park, FL 32789

A wonderful opportunity to build your dream home on one of Winter Park’s most idyllic streets. Situated on a quaint, one-way brick street with a charming park at its center, this exceptional 12,581-square-foot deep lot offers a rare combination of space, character, and location.Currently featuring a 3-bedroom, 2.5-baths, plus office home with 2,080 square feet, the property offers the

Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

150 E Reading Way, Winter Park, FL 32789
/2
$1,688,750

Sold Apr 01, 2026

1705 Elizabeths Walk, Winter Park, FL 32789
- 5 Beds
- 5 Baths
- 3,820 Sq Ft
- Built 2005
Last Sold Summary
- 2% Above List Price
- $442/SF
- 3 Days On Market
Current Estimated Value $1,712,545

Last Listing Agent Keith Moore HOMEVEST REALTY

1705 Elizabeths Walk, Winter Park, FL 32789

/2
Est $668,371

Not Listed For Sale

1130 Washington Ave Unit 11C, Winter Park, FL 32789
- 3 Beds
- 2.5 Baths
- 2,069 Sq Ft
- Built 1981
1130 Washington Ave Unit 11C, Winter Park, FL 32789

Last Sold Summary
- 6 Days On Market
Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

/27
$975,000

$10K PRICE INCREASE
- 4 Beds
- 3 Baths
- 2,528 Sq Ft
471 Holt Ave, Winter Park, FL 32789

Exceptional Winter Park Opportunity with In-Law Suite & Income PotentialDiscover the opportunity to own a versatile property in one of Central Florida’s most desirable locations. 471 Holt Ave. in Winter Park offers buyers something increasingly valuable: flexibility. With a private in-law suite, this property presents an exciting opportunity for multigenerational living, a guest suite,

Tina Bollet FLORIDA HOME TEAM REALTY LLC

471 Holt Ave, Winter Park, FL 32789
/81
$2,925,000

Sold Sep 16, 2026

1597 Oakhurst Ave, Winter Park, FL 32789
- 5 Beds
- 4.5 Baths
- 4,410 Sq Ft
- Built 2015
Last Sold Summary
- 8% Above List Price
- $663/SF
- 2 Days On Market
Current Estimated Value $2,538,752

Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

1597 Oakhurst Ave, Winter Park, FL 32789

/2
Est $956,029

Not Listed For Sale

627 N Interlachen Ave Unit B, Winter Park, FL 32789
- 2 Beds
- 2 Baths
- 1,610 Sq Ft
- Built 1981
627 N Interlachen Ave Unit B, Winter Park, FL 32789

Last Sold Summary
- 164 Days On Market
Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

/15
$88,999

$1K PRICE DROP Pending
- 1 Bed
- 1 Bath
- 638 Sq Ft
1695 Lee Rd Unit B108, Winter Park, FL 32789

This charming 1bedroom, 1bathroom condo is a fantastic opportunity for both homeowners and investors. Located in a desirable area close to shopping, restaurants, and everyday conveniences, it offers comfort, convenience, and excellent value.The kitchen comes fully equipped with a refrigerator, stove, dishwasher, and microwave, and the unit also includes a washer and dryer for added

Brandy Ray LOKATION

1695 Lee Rd Unit B108, Winter Park, FL 32789

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