Homes in ZIP Code 32789

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  /53

  $2,265,000 Open Tue 12PM - 2PM

  • 5 Beds
  • 3.5 Baths
  • 3,691 Sq Ft

  1885 Temple Dr, Winter Park, FL 32789

  NEW 2026 Black Steel doors windows with low e-dual pane glass ($150k value!). Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most

  Jennifer Sloan COMPASS FLORIDA LLC

  1885 Temple Dr, Winter Park, FL 32789
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  /35

  $1,750 - $2,750 per month

  Hannibal Square

  2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  433 W New England Ave, Winter Park, FL 32789
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  /2

  $580,000 Sold May 16, 2025

  1392 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2008

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 123 Days On Market

  Current Estimated Value $546,613

  Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

  1392 Indiana Ave, Winter Park, FL 32789
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  /24

  Est $782,132 Not Listed For Sale

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft
  • Built 2004

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  Last Sold Summary

  • $401/SF
  • 280 Days On Market

  Last Sold Price $785,000

  Last Listing Agent Tyler Reik KELLER WILLIAMS WINTER PARK
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  /14

  $2,289,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,334 Sq Ft

  2722 Eastern Pkwy, Winter Park, FL 32789

  Under contract-accepting backup offers. Under Construction. Masterfully designed new construction by LUIH Luxury Homes, where architectural elegance and refined livability meet an unbeatable lifestyle. Located in the Audubon Park School District just a short stroll from the iconic East End Market. From its captivating façade to its meticulously curated interiors, every element of this residence

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  2722 Eastern Pkwy, Winter Park, FL 32789
• 

  

  /13

  $2,500 per month

  • 3 Beds
  • 2 Baths
  • 1,226 Sq Ft
  • House for Rent

  2743 Sanbina St, Winter Park, FL 32789

  Welcome to this beautifully updated 3-bedroom, 2-bath home located in the heart of Winter Park. Filled with abundant natural light throughout and thoughtful upgrades, this home offers a warm and inviting atmosphere that would be perfect for your family. Highlights:-Primary suite featuring a walk-in closet and private ensuite bathroom-Classic terrazzo flooring-Recently remodeled

  Summer Hornburg BELMONT REALTY

  2743 Sanbina St, Winter Park, FL 32789
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  /2

  $4,772,500 Sold Sep 18, 2025

  765 Via Lugano, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,319 Sq Ft
  • Built 2019

  Last Sold Summary

  • $1,105/SF
  • 1 Day On Market

  Current Estimated Value $4,664,184

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

  765 Via Lugano, Winter Park, FL 32789
• 

  

  /22

  Est $5,368,342 Not Listed For Sale

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 5,430 Sq Ft
  • Built 2005

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $1,104/SF
  • 0 Days On Market

  Last Sold Price $5,995,000

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
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  /75

  $3,055,000

  • 4 Beds
  • 4.5 Baths
  • 4,129 Sq Ft

  151 Oakwood Way, Winter Park, FL 32789

  Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor

  Matthew Burks CORCORAN PREMIER REALTY

  151 Oakwood Way, Winter Park, FL 32789
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  /27

  $1,365 - $2,100 per month

  Westmount at Winter Park

  Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  1701 Lee Rd, Winter Park, FL 32789
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  /2

  $3,100,000 Sold Jun 27, 2025

  731 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,260 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 45 Days On Market

  Current Estimated Value $2,941,576

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
• 

  /2

  Est $2,754,843 Not Listed For Sale

  1737 Lookout Landing Cir, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 5,066 Sq Ft
  • Built 2013

  1737 Lookout Landing Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $533/SF
  • 232 Days On Market

  Last Sold Price $2,699,999

  Last Listing Agent Amy Wilson KELLER WILLIAMS REALTY AT THE PARKS
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  /46

  $1,695,000 New Construction

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

  629 Country Club Dr, Winter Park, FL 32789

  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 with natural light and offer water views

  Randy Lazarus CLASSIC HOMES

  629 Country Club Dr, Winter Park, FL 32789
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  /18

  $6,750 per month

  • 4 Beds
  • 3.5 Baths
  • 3,276 Sq Ft
  • House for Rent

  527 Langholm Dr, Winter Park, FL 32789

  Beautiful custom home with an open floor plan featuring 4 bedrooms, 3.5 baths, downstairs office, 2 car garage, huge loft for gaming and an additional private Bonus Room that can be utilized as a gym or flex room. Master Bedroom and office are conveniently located on the first floor. Additional features of this home include a gourmet kitchen with island, stainless steel appliances, granite

  Nancy Woodruff WOODRUFF REALTY, INC.

  527 Langholm Dr, Winter Park, FL 32789
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  /2

  $2,700,000 Sold Oct 02, 2025

  1445 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,489 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $601/SF
  • 2 Days On Market

  Current Estimated Value $2,652,725

  Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

  1445 Holts Grove Cir, Winter Park, FL 32789
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  /42

  Est $686,657 Not Listed For Sale

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $445/SF
  • 75 Days On Market

  Last Sold Price $700,000

  Last Listing Agent Scott Garstka CHARLES RUTENBERG REALTY ORLANDO
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  /46

  $1,899,500 Open Sun 2PM - 4PM

  • 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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  /27

  $1,236 - $2,425 per month

  Village Park Senior

  1 - 3 Beds

  550 W Denning Dr, Winter Park, FL 32789

  WINTER PARK VILLAGE, an established lifestyle center located just north of Orlando in the affluent community of Winter Park on 17-92 between Lee Road and Fairbanks Avenue. This is the area’s most exciting destination for upscale shopping, dining, entertainment and just an overall great place to spend time away from the mall madness.

  550 W Denning Dr, 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 $915,881

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  /30

  Est $755,652 Not Listed For Sale

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789

  Last Sold Summary

  • 18% Above List Price
  • $380/SF
  • 0 Days On Market

  Last Sold Price $640,000

  Last Listing Agent Maria Van Warner FANNIE HILLMAN & ASSOCIATES
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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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  /15

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Townhouse for Rent

  307 Sandlewood Trail, Winter Park, FL 32789

  This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  307 Sandlewood Trail, 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 $3,427,716

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

  2171 Forrest Rd, Winter Park, FL 32789
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  /30

  Est $1,365,912 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

  • 6% Below List Price
  • $530/SF
  • 3 Days On Market

  Last Sold Price $1,450,000

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC
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  /69

  $1,675,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 3,263 Sq Ft

  446 Alberta Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Charming Opportunity in Prime Winter Park – 446 Alberta Drive, Winter Park, FL! First time ever on the market and sits on a double lot that is .35 acres. Only a mile stroll to the famous Park Ave shops, dining and entertaining. Home site over looks Lake Osceola and the multi million dollar homes all around!! A neighborhood lot, a few doors down, allows

  Vonda Fields CHARLES RUTENBERG REALTY ORLANDO

  446 Alberta Dr, Winter Park, FL 32789
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  /20

  $3,995 per month

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!!PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING!This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or

  438 W Swoope Ave, Winter Park, FL 32789
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  /2

  $520,000 Sold Mar 31, 2025

  1810 Taylor Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Below List Price
  • $372/SF
  • 0 Days On Market

  Current Estimated Value $568,307

  Last Listing Agent Julia Dalessandro FANNIE HILLMAN & ASSOCIATES

  1810 Taylor Ave, Winter Park, FL 32789
• 

  /2

  Est $948,060 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

  • 13% Above List Price
  • $322/SF
  • 51 Days On Market

  Last Sold Price $840,000

  Last Listing Agent Emily Bearden COMPASS FLORIDA LLC
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  /57

  $1,970,000

  • 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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  /24

  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 118, Winter Park, FL 32789

  Investment opportunity! Discover this hidden gem—a 2-bed, 1-bath condo nestled in the heart of Winter Park. Situated in the serene Lake Killarney Condos, this property offers some of the town's most breathtaking sunsets from a sprawling lakefront lot. Enjoy extensive grassy areas and a community pool right on your doorstep. Ideally located near essentials and leisure spots including Publix,

  Adriana Montes MBA FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 118, 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 $3,843,313

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

  33 Eastwind Ln, Maitland, FL 32751
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  /2

  Est $1,541,213 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

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES
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  /57

  $1,899,900

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  1521 Chestnut Ave, Winter Park, FL 32789

  Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept

  Sue Silberbusch COMPASS FLORIDA LLC

  1521 Chestnut Ave, Winter Park, FL 32789
• 

  

  /45

  $1,940 per month

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

  1307 Formosa Ave Unit SI ID1250011P, Winter Park, FL 32789

  The advertised rate of $1,941/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 4, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  1307 Formosa Ave Unit SI ID1250011P, 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 $1,606,227

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
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  /38

  Est $3,020,668 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

  • 6% Below List Price
  • $950/SF
  • 3 Days On Market

  Last Sold Price $3,200,000

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

  $1,974,900

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

  640 Arjay Way, Winter Park, FL 32789

  Price Improvement on this amazing oversized lot! 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 character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native

  Farah Bloom KELLER WILLIAMS WINTER PARK

  640 Arjay Way, Winter Park, FL 32789
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  /89

  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • House for Rent

  1815 Barker Dr, Winter Park, FL 32789

  Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. Pricing includes utilities/wifi. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals,

  Benjamin Cole, IV SOTERA LIVING

  1815 Barker Dr, Winter Park, FL 32789
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  /2

  $3,200,000 Sold Apr 30, 2025

  1833 Loch Berry Rd, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,770 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $671/SF
  • 5 Days On Market

  Current Estimated Value $3,024,879

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1833 Loch Berry Rd, Winter Park, FL 32789
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  /30

  Est $1,462,460 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

  • 5% Below List Price
  • $749/SF
  • 0 Days On Market

  Last Sold Price $1,547,500

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

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