Winter Park, FL Homes

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  /32

  $469,900

  • 4 Beds
  • 2 Baths
  • 1,778 Sq Ft

  7104 Wrenwood Way, Winter Park, FL 32792

  This beautifully updated 4 bedroom, 2 bathroom, 2 car garage home offers modern style, thoughtful upgrades, and a prime location just steps from the neighborhood elementary school. From the moment you arrive, you’ll notice the curb appeal of the corner lot framed by mature trees and a newer white vinyl fence. Inside, the home features a spacious split floor plan with wood-grain laminate flooring,

  Jennah LeBruno, LLC THE WILKINS WAY LLC

  7104 Wrenwood Way, Winter Park, FL 32792
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  /16

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,585 Sq Ft
  • House for Rent

  7413 Fieldcrest Ave, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2339.90. That covers your base rent, $2195.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7413 Fieldcrest Ave, Winter Park, FL 32792
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  /2

  $1,450,000 Sold Aug 07, 2025

  • 3,784 Sq Ft
  • $383/SF
  • 93 Days On Market

  • 6 Beds
  • 5 Baths
  • Built 1951

  1299 Harding St, Winter Park, FL 32789

  Welcome to your private slice of paradise—a beautifully renovated home with a brand new 2024 pied-a-terre guest retreat, nestled just steps from the iconic Kraft Azalea Garden on the shores of Lake Maitland, and walking distance to the renowned boutiques and dining of Park Avenue. Positioned on a beautiful 0.30-acre lot, this residence is enveloped with manicured landscaping, meandering brick

  Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1299 Harding St, Winter Park, FL 32789
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  /32

  Est $588,741 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft

  1178 Wildmeadow Run, Winter Park, FL 32792

  1178 Wildmeadow Run, Winter Park, FL 32792
• 

  

  

  /22

  $155,000

  • 1 Bed
  • 1 Bath
  • 763 Sq Ft

  4960 Tangerine Ave Unit 4960, Winter Park, FL 32792

  Very well maintained cozy condo in Winter Park. This condo has one bedroom, and one bathroom. Living area has beautiful laminate flooring in the bedroom, family, room, and dining area, Kitchen and bathroom are tile. Appliances that stays are washer, dryer, fridge, oven, microwave, and ceiling fan! Basically just pack your bags, and move right in! This condo also features a storage room, and a

  Stacy Chen KELLER WILLIAMS ADVANTAGE III

  4960 Tangerine Ave Unit 4960, Winter Park, FL 32792
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  /9

  $1,650 per month

  • 2 Beds
  • 1.5 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  2710 Townley Ct, Winter Park, FL 32792

  Fantastic location without HOA. Two bedrooms and a bathroom upstairs with a balcony in one of the rooms to enjoy your morning coffee. Downstairs includes a half bath for your guests, an updated kitchen, and a laundry room. Don't miss your opportunity to see this home. Self-touring options are available.

  Stephanie Pelaez NATIONAL REAL ESTATE LLC

  2710 Townley Ct, Winter Park, FL 32792
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  /2

  $155,000 Sold Aug 06, 2025

  • 840 Sq Ft
  • $185/SF
  • 388 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  3651 N Goldenrod Rd Unit 107, Winter Park, FL 32792

  MAJOR PRICE IMPROVEMENT!!! Welcome to your new home at 3651 North Goldenrod Road, #B107, Winter Park, FL 32792! This charming FIRST FLOOR 2-bedroom, 2-bathroom condominium offers the perfect blend of comfort and convenience. Inside, you'll find a well-appointed kitchen featuring solid wood cabinets, ample eating space, and all the essential appliances, including a dishwasher, dryer, microwave,

  Veronica Figueroa EXP REALTY LLC

  3651 N Goldenrod Rd Unit 107, Winter Park, FL 32792
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  /18

  Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,813 Sq Ft

  1411 Miller Ave, Winter Park, FL 32789

  1411 Miller Ave, Winter Park, FL 32789
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  /27

  $135,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit C206, Winter Park, FL 32789

  Welcome to a delightfully bright and inviting 2-bedroom, 1-bathroom condo nestled in the peaceful Waterfall Cove community at 1695 Lee Rd, Unit C206, Winter Park, FL 32789. Thoughtfully designed, this home features a covered balcony that invites relaxing mornings or cozy evenings outdoors, while the spacious primary bedroom offers the convenience of a walk-in closet—perfectly blending comfort and

  Justin Adams EXP REALTY LLC

  1695 Lee Rd Unit C206, Winter Park, FL 32789
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  /11

  $2,390 per month

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft
  • House for Rent

  1601 Aster Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2654.90. That covers your base rent, $2390.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1601 Aster Dr, Winter Park, FL 32792
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  /2

  $185,000 Sold Aug 05, 2025

  • 987 Sq Ft
  • $187/SF
  • 7 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  200 St Andrews Blvd Unit 802, Winter Park, FL 32792

  Welcome to easy living in the heart of Winter Park! This beautiful 1st-floor condo is move-in ready and packed with value—featuring a new electrical panel, in-unit washer and dryer, fresh interior paint, and popcorn ceilings removed for a modern, clean feel. Enjoy the convenience of a covered carport and peace of mind knowing this property is Fannie Mae eligible so you won't have any issue

  Abby Greenberg COMPASS FLORIDA LLC

  200 St Andrews Blvd Unit 802, Winter Park, FL 32792
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  /2

  Est $108,676 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 549 Sq Ft

  3035 George Mason Ave Unit 18, Winter Park, FL 32792

  3035 George Mason Ave Unit 18, Winter Park, FL 32792
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  /54

  $362,000

  • 3 Beds
  • 2 Baths
  • 1,461 Sq Ft

  3490 Bougainvillea Dr, Winter Park, FL 32792

  Step into the charm and comfort of this inviting 3-bedroom, 2-bath Winter Park home, where every space is designed to blend functionality with the warmth of Florida living and the freedom of no HOA. From the moment you walk in, you’re greeted by bright and open gathering spaces including a welcoming living room, a cozy breakfast nook, and a spacious dining area that flows seamlessly into the

  EJ Jimenez KELLER WILLIAMS ADVANTAGE III

  3490 Bougainvillea Dr, Winter Park, FL 32792
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  /16

  $2,410 per month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  1729 Puritan Ave, Winter Park, FL 32792

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  1729 Puritan Ave, Winter Park, FL 32792
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  /2

  $600,000 Sold Aug 05, 2025

  • 1,464 Sq Ft
  • $410/SF
  • 26 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  2244 Brookshire Ave, Winter Park, FL 32792

  Welcome to this delightful 3-bedroom, 2-bathroom single-family home located in the highly sought-after Brookshire Heights neighborhood of Winter Park. Step inside to discover an open-concept living area, perfect for entertaining or relaxing with family. The layout flows seamlessly from the living room to the dining area and kitchen, creating a bright and airy space filled with natural light. A

  Melissa Johnson EXP REALTY LLC

  2244 Brookshire Ave, Winter Park, FL 32792
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  /18

  Est $460,744 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  1916 Erudite Way, Winter Park, FL 32792

  1916 Erudite Way, Winter Park, FL 32792
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  /9

  $195,000

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792

  *** SELLER WILL PAY SPECIAL ASSESSMENT AT CLOSING BRING MONTHLY ASSESSMENT TO $420****Sought after Winter Park Location! 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community. 1,031 sq. ft. newer roof installed in 2023. The exterior is thoughtfully landscaped, enhancing the home’s inviting curb appeal. Conveniently located just: 10 minutes to Downtown Orlando, 15

  Abranette Lopez LPT REALTY, LLC

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792
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  /9

  $2,545 per month

  • 4 Beds
  • 2.5 Baths
  • 1,792 Sq Ft
  • House for Rent

  2218 Winter Woods Blvd, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2689.90. That covers your base rent, $2545.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  2218 Winter Woods Blvd, Winter Park, FL 32792
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  /2

  $415,000 Sold Aug 05, 2025

  • 1,725 Sq Ft
  • $241/SF
  • 230 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  1820 Blaine Terrace, Winter Park, FL 32792

  Nestled in the heart of Winter Park, this stunning home offers a perfect blend of elegance and functionality. Featuring three spacious bedrooms and two and a half baths, it boasts an open layout ideal for both family living and entertaining. The bright and airy living room is flooded with natural light, creating a welcoming space for relaxation. Beautiful floors flow seamlessly throughout,

  Melissa Gonzalez LPT REALTY, LLC

  1820 Blaine Terrace, Winter Park, FL 32792
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  /39

  Est $1,534,432 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,345 Sq Ft

  1007 S Pennsylvania Ave, Winter Park, FL 32789

  1007 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  /22

  $399,900

  • 4 Beds
  • 2 Baths
  • 1,570 Sq Ft

  330 Elkhorn Ct, Winter Park, FL 32792

  One of Winter Park’s most desirable neighborhoods. Featuring Large fenced backyard — perfect for pets, play, or future landscapingExpansive family room, formal living room, and dedicated dining area2-car garage for secure parking and storage new roof (2020) and newer hot water heater, fully replumbed in 2000Located in a quiet, friendly community with tree-lined streetsThis home

  Robert D'Antuono IRIS INTERNATIONAL

  330 Elkhorn Ct, Winter Park, FL 32792
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  /23

  $1,550 per month

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

  1695 Lee Rd Unit D212, Winter Park, FL 32789

  This great second floor two-bedrooms 1 bath condo is in the quiet community of Waterfall Cove just off LeeRoad and 17-92 intersection. Conveniently located walking distance from shopping, dining, and Winter Park Village. Close to Park Avenue,Maitland 's Lake Lilly Park with the Farmer's Market and to Rollins College. Easy I-4 access. Open floor plan, walk in closet, and stack-able washer and

  giuseppina moriconi GM SUNSHINE REALTY LLC

  1695 Lee Rd Unit D212, Winter Park, FL 32789
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  /2

  $425,000 Sold Aug 04, 2025

  • 1,148 Sq Ft
  • $370/SF
  • 8 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1969

  690 Osceola Ave Unit 410, Winter Park, FL 32789

  Welcome to this newly updated 2-bedroom, 2-bath condo ideally situated just steps down from shops, dining, and cultural attractions of Park Ave and Rollins College. Freshly painted and featuring brand-new flooring throughout, this home offers a perfect blend of comfort, convenience, and modern style.The spacious open layout includes a bright living area that opens to a lovely screened-in

  Catherine Mitchell LOMBARDI LEMAY REALTY

  690 Osceola Ave Unit 410, Winter Park, FL 32789
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  /32

  Est $463,763 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  2445 Firstlight Way, Winter Park, FL 32792

  2445 Firstlight Way, Winter Park, FL 32792
• 

  

  /16

  $299,900

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  2462 Harbour Way, Winter Park, FL 32792

  Welcome to 2462 Harbour Way, a beautifully maintained single-story townhome nestled in the highly sought-after Windward Square community of Winter Park. This move-in ready 3-bedroom, 2-bathroom home offers comfort, style, and convenience—all in one of Central Florida’s most desirable areas. Step inside to discover a sunlit dinette that flows seamlessly into a spacious kitchen, featuring gleaming

  Itzel Sotorosa NONA LEGACY POWERED BY LA ROSA

  2462 Harbour Way, Winter Park, FL 32792
• 

  

  /17

  $2,290 per month

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft
  • House for Rent

  5216 N Indiana Ave, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2434.90. That covers your base rent, $2290.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  5216 N Indiana Ave, Winter Park, FL 32792
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  /2

  $200,000 Sold Aug 04, 2025

  • 1,018 Sq Ft
  • $196/SF
  • 159 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1984

  2935 Antique Oaks Cir Unit 64, Winter Park, FL 32792

  Welcome to your new home at 2935 Antique Oaks Cir Apt 64, a beautifully renovated 2-bedroom, 2-bathroom apartment in the heart of Winter Park, Florida. This second-floor unit offers a comfortable and convenient lifestyle with no upstairs neighbors, ensuring peace and privacy. Key Features:Renovated Interior: Enjoy a fresh and modern living space with stylish LVP flooring

  Chris Creegan CREEGAN GROUP

  2935 Antique Oaks Cir Unit 64, Winter Park, FL 32792
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  /62

  Est $2,040,792 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 7,762 Sq Ft

  2156 Talman Ct, Winter Park, FL 32792

  2156 Talman Ct, Winter Park, FL 32792
• 

  

  /30

  $545,000

  • 4 Beds
  • 2 Baths
  • 1,718 Sq Ft

  240 Orange Terrace Dr, Winter Park, FL 32789

  JUST REDUCED, SELLER MOTIVATED!Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and all that Winter Park has to offer.Fully renovated in 2021—including new roof, electrical, plumbing,

  Susan Pinnock A+ REALTY PROFESSIONALS, INC

  240 Orange Terrace Dr, Winter Park, FL 32789
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  /34

  $2,950 per month

  • 4 Beds
  • 2 Baths
  • 1,276 Sq Ft
  • House for Rent

  5037 Lake Howell Rd, Winter Park, FL 32792

  Single family home for rent in the desirable city of Winter Park! This beautiful home features a main house with 3 bedrooms and 1 bathroom, with an in-law suite of 1 bedroom and 1 bathroom, located in the back of the oversized backyard where you can park all your vehicles including your boat or RV as there is no HOA! Enjoy the 0.27 acre lot completely fenced backyard for yourself, friends and

  Rafael Casallas, Pa EMPIRE NETWORK REALTY

  5037 Lake Howell Rd, Winter Park, FL 32792
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  /2

  $815,000 Sold Aug 04, 2025

  • 2,533 Sq Ft
  • $322/SF
  • 316 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1926

  1310 Aloma Ave, Winter Park, FL 32789

  Elegant Spanish 4 bedroom, 2.5 bathroom home. Beautifully updated Winter Park home. Enjoy all the luxuries and upgrades this home has to offer including triple crown molding, tall baseboards, refinished original hard wood floors, recessed lighting, French doors, paver driveway and newer windows though out with new plantation shutters. Large living room has a fabulous brick wood burning

  Rhonda Chesmore KELLY PRICE & COMPANY LLC

  1310 Aloma Ave, Winter Park, FL 32789
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  /20

  Est $457,445 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  2448 Firstlight Way, Winter Park, FL 32792

  2448 Firstlight Way, Winter Park, FL 32792
• 

  

  /27

  $355,000

  • 4 Beds
  • 2 Baths
  • 1,678 Sq Ft

  3521 Balsam Dr, Winter Park, FL 32792

  NO HOA! Desirable Winter Park Neighborhood!Welcome to this beautiful 4-bedroom, 2-bathroom and 2 car garage. Home situated on a spacious corner lot. This property features an open layout, gorgeous flooring throughout, and a 2-car garage. The home has been re-plumbed, features a 2 year old roof, and the electrical system has been update to code. Conveniently located near the Airport,

  Elena Rios DALTON WADE INC

  3521 Balsam Dr, Winter Park, FL 32792
• 

  

  /15

  $2,640 per month

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • House for Rent

  7666 Glenmoor Ln, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  7666 Glenmoor Ln, Winter Park, FL 32792
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  /2

  $320,000 Sold Aug 01, 2025

  • 1,715 Sq Ft
  • $187/SF
  • 18 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  2020 Cocos Ct, Winter Park, FL 32792

  Fantastic Investment or Renovation Opportunity in Winter Park! Located in the desirable Eastbrook community, this 3-bedroom, 2-bathroom POOL home with ONLY ONE OWNER sits on an oversized .30 ACRE CORNER LOT on a quiet CUL-DE-SAC with no HOA. Offering 1715 square feet of living space, a 1-car garage, and a spacious fenced backyard, this property is a true blank canvas ready for your vision.

  Justin Core EXP REALTY LLC

  2020 Cocos Ct, Winter Park, FL 32792
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  /22

  Est $202,305 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792
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  /32

  $100,000

  • 2 Beds
  • 2 Baths
  • 1,030 Sq Ft

  3053 George Mason Ave Unit 7, Winter Park, FL 32792

  Prime Location and Smart Investment! This spacious 2-bedroom, 2-bath ground-floor condo offers easy, low-maintenance living just one mile from University Boulevard and minutes from The University of Central Florida and Full Sail University. Freshly painted and move-in ready, the updated kitchen features sleek granite countertops and new white appliances. Stylish tile flooring runs throughout the

  John Muccigrosso RE/MAX 200 REALTY

  3053 George Mason Ave Unit 7, Winter Park, FL 32792
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  /15

  $2,300 per month

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave, Winter Park, FL 32789

  Charming 3-Bedroom Home for Rent in Winter ParkThis beautiful 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. Featuring spacious living areas and modern appliances, it offers a comfortable and convenient living environment. Located in a quiet, family-friendly neighborhood, it provides easy access to local shops, restaurants,

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave, Winter Park, FL 32789
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  /2

  $1,607,160 Sold Aug 01, 2025

  • 2,840 Sq Ft
  • $566/SF
  • 2 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2018

  1541 Chestnut Ave, Winter Park, FL 32789

  An extraordinary home, built in 2018 by Lazarus, is on a quaint cobblestone street in the exclusive Tree Streets of Winter Park. Contemporary transitional design has many details and has been beautifully maintained and upgraded. A four-bedroom, three-bath pool home stretches over 2,800 square feet with natural light filling the spaces through expansive windows. The home offers open concept living

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1541 Chestnut Ave, Winter Park, FL 32789
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  /77

  Est $756,618 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7904 Pleasant Pine Cir, Winter Park, FL 32792

  7904 Pleasant Pine Cir, Winter Park, FL 32792

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