Homes in ZIP Code 32789

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  /29

  $1,925,000

  • 4 Beds
  • 4 Baths
  • 2,653 Sq Ft

  721 Pansy Ave, Winter Park, FL 32789

  Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  721 Pansy Ave, Winter Park, FL 32789
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  /11

  $2,350 Per Month

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft
  • House for Rent

  1931 Staunton Ave, Winter Park, FL 32789

  Available for rent! Tucked onto a desirable corner lot just steps from Lake Killarney, this beautifully updated 3 bedroom, 2 bath single-family home puts you in one of the area's most sought-after spots. Walkable, quiet, and moments from the water. Inside, the home is move-in ready with a full suite of brand-new appliances (dishwasher, range, and refrigerator) plus washer/dryer hookups ready for

  Zach Mitchell SAND DOLLAR REALTY GROUP INC

  1931 Staunton Ave, Winter Park, FL 32789
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  /2

  $916,000 Sold Jul 17, 2025

  609 Langholm Dr, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $462/SF
  • 8 Days On Market

  Current Estimated Value $904,622

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  /30

  Est $1,305,246 Not Listed For Sale

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,734 Sq Ft
  • Built 2009

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $530/SF
  • 3 Days On Market

  • Last Sold Price $1,450,000
  • May 20, 2024

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC
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  /82

  $2,395,000 New Construction

  • 4 Beds
  • 4 Baths
  • 3,111 Sq Ft

  2361 Mulbry Dr, Winter Park, FL 32789

  *** Parade of Homes Showcase This Weekend | Open House Saturday & Sunday 10 AM – 6 PM ***Casa Noir — Brand new construction custom home selected as a 2026 Parade of Homes showcase in Winter Park. 4 bedrooms. 4 full baths. Dedicated office. Loft. 2-car garage. Approximately 3,200 sq ft living space. Custom finishes done to perfection throughout. Inside, the foyer delivers on every promise made

  Ahmad Hassan COMPASS FLORIDA LLC

  2361 Mulbry Dr, Winter Park, FL 32789
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  /24

  $3,350

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Townhouse for Rent

  1886 Demetree Dr, Winter Park, FL 32789

  Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter Park Welcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals. This thoughtfully

  1886 Demetree Dr, Winter Park, FL 32789
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  /2

  $3,485,000 Sold Oct 17, 2025

  2171 Forrest Rd, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,565 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $763/SF
  • 134 Days On Market

  Current Estimated Value $3,358,092

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

  2171 Forrest Rd, Winter Park, FL 32789
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  /2

  Est $930,692 Not Listed For Sale

  1245 Wisconsin Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft
  • Built 2013

  1245 Wisconsin Ave, Winter Park, FL 32789

  Last Sold Summary

  • 11% Above List Price
  • $322/SF
  • 51 Days On Market

  • Last Sold Price $840,000
  • Sep 30, 2024

  Last Listing Agent Emily Bearden COMPASS FLORIDA LLC
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  /3

  $1,949,999 New Construction

  • 4 Beds
  • 4 Baths
  • 2,810 Sq Ft

  2501 Lafayette Ave, Winter Park, FL 32789

  Under Construction. GENEROUSLY APPOINTED LUXURY HOME at $1,875.000 with sound and water walls at $1,950,000.Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4-bedroom, 4-bath home offers over 2,800 square feet of bright, open living space, designed for both comfort and functionality. Enter through your custom pivot front door into the foyer

  Tab Bish LLC REAL BROKER, LLC

  2501 Lafayette Ave, Winter Park, FL 32789
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  /12

  $2,550 Per Month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Condo for Rent

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789

  **MOVE IN SPECIAL $500 off first months rent** Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
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  /2

  $3,950,000 Sold Jun 17, 2025

  33 Eastwind Ln, Maitland, FL 32751

  • 5 Beds
  • 4.5 Baths
  • 4,715 Sq Ft
  • Built 2024

  Last Sold Summary

  • $838/SF
  • 0 Days On Market

  Current Estimated Value $3,736,269

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

  33 Eastwind Ln, Maitland, FL 32751
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  /2

  Est $1,549,094 Not Listed For Sale

  101 S New York Ave Unit 303, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,174 Sq Ft
  • Built 2009

  101 S New York Ave Unit 303, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $496/SF
  • 129 Days On Market

  • Last Sold Price $1,575,000
  • Jan 10, 2025

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
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  /25

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  1881 Lake Spier Dr, Winter Park, FL 32789

  Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier.Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy,

  Rafael Zenke Pinhao NOVA REAL ESTATE SERVICES INC

  1881 Lake Spier Dr, Winter Park, FL 32789
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  /13

  $1,522

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 1D, Winter Park, FL 32789

  EXCELLENT LOCATION within walking distance to retail stores, restaurants, and parks. This remodeled second-floor unit offers lake access, a pool, and includes water in the rent. Flexible deposit option available—can be split over the first three months.

  1500 Gay Rd Unit 1D, Winter Park, FL 32789
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  /2

  $1,645,000 Sold May 20, 2025

  681 Balmoral Rd, Winter Park, FL 32789

  • Land
  • 1.14 Acres
  • $1,442,982 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 55 Days On Market

  Current Estimated Value $1,598,071

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
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  /38

  Est $3,053,798 Not Listed For Sale

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,367 Sq Ft
  • Built 2008

  140 E Morse Blvd Unit G, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $950/SF
  • 3 Days On Market

  • Last Sold Price $3,200,000
  • Jul 31, 2023

  Last Listing Agent Andrea Sider, PA KELLER WILLIAMS WINTER PARK
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  /46

  $1,695,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  629 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home

  Randy Lazarus CLASSIC HOMES

  629 Country Club Dr, Winter Park, FL 32789
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  /12

  $6,000 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Apartment for Rent

  301 W Comstock Ave, Winter Park, FL 32789

  Under Construction. Beautiful 2 bedroom, 2.5 bath, laundry in unit, detached two (2) car garage with private guest suite located in Hannibal Square. New Construction.

  Sydney Brownlee THE SYDGAN CORP

  301 W Comstock Ave, Winter Park, FL 32789
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  /2

  $228,000 Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $226,368

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  /30

  Est $1,429,852 Not Listed For Sale

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

  • 3 Beds
  • 2 Baths
  • 2,066 Sq Ft
  • Built 1960

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

  Last Sold Summary

  • 8% Below List Price
  • $749/SF
  • 0 Days On Market

  • Last Sold Price $1,547,500
  • Dec 16, 2023

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  /46

  $1,849,000

  • 4 Beds
  • 3.5 Baths
  • 3,727 Sq Ft

  1840 Bryan Ave, Winter Park, FL 32789

  This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1840 Bryan Ave, Winter Park, FL 32789
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  /9

  $1,850

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 9D, Winter Park, FL 32789

  Two-bedroom, two-bath walk-up condo off Lake Killarney in Winter Park, Florida. Spacious rooms, custom upgrades, quiet, and well maintained. Located in the Chateaux du Lac community at 1500 GayRoad. Within walking distance of Winter Park Village, Traders Joe's, restaurants and more. Minutes from AdventHealth Orlando, Park Avenue, Rollins College, and I-4.Pet free unit. Ideally seeking

  1500 Gay Rd Unit 9D, Winter Park, FL 32789
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  /2

  $1,905,000 Sold Apr 10, 2026

  501 Henkel Cir, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,746 Sq Ft
  • Built 2009

  Last Sold Summary

  • 4% Above List Price
  • $509/SF
  • 4 Days On Market

  Current Estimated Value $1,855,042

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  501 Henkel Cir, Winter Park, FL 32789
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  /2

  Est $366,901 Not Listed For Sale

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 864 Sq Ft
  • Built 1983

  1312 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Last Sold Summary

  • 14% Below List Price
  • $492/SF
  • 36 Days On Market

  • Last Sold Price $425,000
  • Oct 17, 2024

  Last Listing Agent Jenni Owens KELLER WILLIAMS WINTER PARK
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  /55

  $1,500,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,281 Sq Ft

  246 Palmer Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  246 Palmer Ave, Winter Park, FL 32789
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  /17

  $1,400 Per Month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit D213, Winter Park, FL 32789

  Adorable and cozy second floor condo, conveniently located off Lee Road in Orlando, minutes from SR I-4. This 2-bedroom 1 full bath condo is located in the quiet community or Waterfall Cove. Water is included with a community pool and playground for tenants to enjoy. Open floor plan with carpet and laminate in kitchen and bath. Fresh paint throughout. Balcony just outside the sliders in living

  Rachel DeCamp RLL Real Estate Group

  1695 Lee Rd Unit D213, Winter Park, FL 32789
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  /2

  $420,000 Sold Jan 15, 2026

  1847 Azalea Ave, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 1,477 Sq Ft
  • Built 1961

  Last Sold Summary

  • $284/SF
  • 1 Day On Market

  Current Estimated Value $414,739

  Last Listing Agent Trace Christian, III COLDWELL BANKER REALTY

  1847 Azalea Ave, Winter Park, FL 32789
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  /2

  Est $820,333 Not Listed For Sale

  2320 Janice Ave, Winter Park, FL 32789

  2320 Janice Ave, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • 2 Days On Market

  • Last Sold Price $799,000
  • Apr 30, 2025

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES
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  /57

  $1,870,000

  • 5 Beds
  • 4.5 Baths
  • 4,363 Sq Ft

  1177 Kenwood Ave, Winter Park, FL 32789

  Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat,

  Karen Albright OPENDOOR BROKERAGE LLC

  1177 Kenwood Ave, Winter Park, FL 32789
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  /37

  $4,195 Per Month

  • 4 Beds
  • 3 Baths
  • 2,134 Sq Ft
  • WINTER PARK POOL HOME WITH WINTER PARK SCHOOLS! (Orange County Winter Park Schools)

  1625 Tioga Trail, Winter Park, FL 32789

  AVAILABLE FOR MOVE-IN EARLY JUNE 2026.A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD.Very seldom do such nice rental homes come available in the school district of Dommerich, Maitland Middle and Winter Park High! People love The Hills of Winter Park with this home located on a cul-de-sac street.This home features 4 Bedrooms and 3 Full

  1625 Tioga Trail, Winter Park, FL 32789
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  /2

  $199,900 Sold Nov 03, 2025

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 130 Days On Market

  Current Estimated Value $189,746

  Last Listing Agent Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
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  /2

  Est $1,826,827 Not Listed For Sale

  643 Balmoral Rd, Winter Park, FL 32789

  643 Balmoral Rd, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • 17 Days On Market

  • Last Sold Price $1,767,500
  • Mar 21, 2025

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC
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  /46

  $1,890,000 Pending

  • 5 Beds
  • 5 Baths
  • 3,953 Sq Ft

  640 Arjay Way, Winter Park, FL 32789

  Under contract-accepting backup offers. Motivated Sellers! Priced at $35,000 below recent Appraisal Price on this amazing oversized lot! Walk into this home with equity from the start! Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores! This stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless

  Farah Bloom KELLER WILLIAMS WINTER PARK

  640 Arjay Way, Winter Park, FL 32789
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  /16

  $1,400 Per Month

  • 1 Bed
  • 1 Bath
  • 638 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C110, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C110, Winter Park, FL 32789
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  /19

  $172,000 Sold May 23, 2025

  700 Melrose Ave Unit E24, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 787 Sq Ft
  • Built 1964

  Last Sold Summary

  • 14% Below List Price
  • $219/SF
  • 164 Days On Market

  Current Estimated Value $180,280

  Last Listing Agent Susan Dering HOMEVEST REALTY

  700 Melrose Ave Unit E24, Winter Park, FL 32789
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  /30

  Est $631,040 Not Listed For Sale

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1983

  1086 Azalea Ln Unit 1, Winter Park, FL 32789

  Last Sold Summary

  • 7% Above List Price
  • $332/SF
  • 5 Days On Market

  • Last Sold Price $589,000
  • May 22, 2023

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  /50

  $1,425,000

  • 4 Beds
  • 3.5 Baths
  • 2,170 Sq Ft

  1751 Goodrich Ave, Winter Park, FL 32789

  Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

  Stephanie Baldner EXP REALTY LLC

  1751 Goodrich Ave, Winter Park, FL 32789
• 

  

  /21

  $1,595 Per Month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • SPACIOUS 2BR CONDO | MOVE-IN READY | LIMITED AVAILABILITY

  1695 Lee Rd, Winter Park, FL 32789

  Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community.This unit offers the perfect combination of comfort, space, and convenience — ideal for families or professionals looking for a clean and functional home ready for immediate move-in.PROPERTY HIGHLIGHTS:2 Bedrooms / 1 Full Bathroom - Second-floor unit

  1695 Lee Rd, Winter Park, FL 32789
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  /2

  $266,000 Sold Nov 19, 2025

  1500 Gay Rd Unit 9B, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 5 Days On Market

  Current Estimated Value $262,699

  Last Listing Agent Janice Erickson REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 9B, Winter Park, FL 32789
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  /2

  Est $310,744 Not Listed For Sale

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $684/SF
  • 3 Days On Market

  • Last Sold Price $329,900
  • Jan 30, 2025

  Last Listing Agent Susan Logan LOGAN LAND & HOMES, INC.

Showing Results 81 - 120, Page 3 of 18