Florida Neighborhood Realty
  • Sell Your Florida Home
  • Buy A Florida Home
  • Advanced Home Search
Login
407.801.3286

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Central Florida › Orlando Metro › Orange County › Winter Park › Winter Park Single Family Homes

Winter Park Single Family Homes for Sale

Winter Park offers a wide variety of single family home designs, sizes, features, locations and price ranges. Whether you are looking for a starter home, investment home, family home, luxury home or vacation home, Winter Park has a home for you! Below is a list of all currently available single family homes in Winter Park.

Winter Park Single Family Homes for Sale

40 Palmer Avenue, Winter Park image
40 Palmer Avenue, Winter Park $7,250,000 ▲

Under Construction. Opportunities like this rarely present themself, just a eight-minute walk from the iconic shops, restaurants, and cafés of Park Avenue, 40 Palmer repr...

  • 5 Beds
  • 6 Baths
  • Robert Dhu Macdonald Park SubDv.
  • 32789 Zip Code
1260 Alabama Drive, Winter Park image
1260 Alabama Drive, Winter Park $6,900,000

Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent mas...

  • 6 Beds
  • 7 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
1571 Woodland Avenue, Winter Park image
1571 Woodland Avenue, Winter Park $6,000,000

Experience timeless elegance and deliberate craftsmanship in the heart of prestigious Winter Park. This one-of- a-kind exceptional estate offers more than 7,300 square f...

  • 5 Beds
  • 8 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
2661 Via Tuscany, Winter Park image
2661 Via Tuscany, Winter Park $5,999,990

Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordina...

  • 4 Beds
  • 5 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
2228 Azalea Place, Winter Park image
2228 Azalea Place, Winter Park $5,600,000

This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated cor...

  • 5 Beds
  • 6 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
313 Sylvan Drive, Winter Park image
313 Sylvan Drive, Winter Park $5,500,000

Pre-Construction. To be built. This extraordinary lakefront residence on beautiful Lake Sylvan, set on a .37-acre (16,603± square foot) homesite, presents a rare opportun...

  • 4 Beds
  • 5 Baths
  • Sylvan Park SubDv.
  • 32789 Zip Code
231 Chelton Circle, Winter Park image
231 Chelton Circle, Winter Park $4,950,000

Residing among the treelined streets of Winter Park, this stunning, contemporary pool home, designed and built by renowned Phil Kean, truly captures the essence of luxury...

  • 4 Beds
  • 7 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
857 Brock Street, Winter Park image
857 Brock Street, Winter Park $4,650,000

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...

  • 5 Beds
  • 6 Baths
  • Park Grove SubDv.
  • 32789 Zip Code
1525 Granville Drive, Winter Park image
1525 Granville Drive, Winter Park $4,595,000 ▼

There are luxury homes, and then there are homes that redefine luxury altogether. Crafted by renowned luxury builder Vimaro Homes, this extraordinary residence is the pro...

  • 5 Beds
  • 6 Baths
  • Park Grove SubDv.
  • 32789 Zip Code
229 Alexander Place, Winter Park image
229 Alexander Place, Winter Park $4,250,000

Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winni...

  • 4 Beds
  • 6 Baths
  • Alexander Place SubDv.
  • 32789 Zip Code
1441 Cardinal Court, Winter Park image
1441 Cardinal Court, Winter Park $3,995,000 ▼

Beautifully built in 2022 by Lonnie Richardson, this custom one-story home sits on a quiet cul-de-sac in the heart of Winter Park. Designed with a modern, timeless style,...

  • 4 Beds
  • 6 Baths
  • Winflor Court Pt Rep SubDv.
  • 32789 Zip Code
620 Virginia Drive, Winter Park image
620 Virginia Drive, Winter Park $3,890,000

Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of chara...

  • 6 Beds
  • 5 Baths
  • Timberlane Shores SubDv.
  • 32789 Zip Code
2622 Lake Howell Lane, Winter Park image
2622 Lake Howell Lane, Winter Park $3,750,000

Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...

  • 4 Beds
  • 3 Baths
  • Acreage & Unrec SubDv.
  • 32792 Zip Code
207 E Kings Way, Winter Park image
207 E Kings Way, Winter Park $3,650,000

Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully craft...

  • 5 Beds
  • 5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
276 Detmar Drive, Winter Park image
276 Detmar Drive, Winter Park $3,600,000

Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with excep...

  • 4 Beds
  • 5 Baths
  • Detmar Terrace Winter Park SubDv.
  • 32789 Zip Code
2240 Venetian Way, Winter Park image
2240 Venetian Way, Winter Park $3,500,000

Virtually Staged. Positioned on a quiet canal, this exceptional property features a covered boat dock with lift, offering effortless access to the renowned Winter Park Ch...

  • 4 Beds
  • 4 Baths
  • Maitland Shores 1st Add SubDv.
  • 32789 Zip Code
160 W Rockwood Way, Winter Park image
160 W Rockwood Way, Winter Park $3,395,000

Perfectly positioned in the heart of Old Winter Park, the quaint Forrest Hills neighborhood is lined with charming cobblestone streets that wind around Lake Sue. This cus...

  • 5 Beds
  • 6 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
1627 Mizell Avenue, Winter Park image
1627 Mizell Avenue, Winter Park — Urban Perch-A Boutique Homes $3,300,000

One or more photo(s) has been virtually staged. Under Construction. Under construction. Experience approachable luxury combined with wellness-focused living in this newly...

  • 5 Beds
  • 6 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
1581 Forest Avenue, Winter Park image
1581 Forest Avenue, Winter Park $3,275,000 ▼

Virtually Staged. This exceptional Winter Park residence offers a floor plan rarely found in the area, with nearly all living spaces thoughtfully positioned on a single l...

  • 4 Beds
  • 6 Baths
  • Ellno Willo SubDv.
  • 32789 Zip Code
1761 Legion Drive, Winter Park image
1761 Legion Drive, Winter Park $3,265,000

One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, ...

  • 5 Beds
  • 6 Baths
  • Green Oaks Rep 02 SubDv.
  • 32789 Zip Code
361 E Kings Way, Winter Park image
361 E Kings Way, Winter Park $3,199,000

Under Construction. Perfectly positioned along one of Winter Park's most picturesque tree-lined cobblestone streets, this exceptional new construction residence offers a ...

  • 4 Beds
  • 5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1821 Englewood Road, Winter Park image
1821 Englewood Road, Winter Park $3,075,000 ▼

This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues t...

  • 5 Beds
  • 6 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
1836 Whitehall Drive, Winter Park image
1836 Whitehall Drive, Winter Park $2,995,000 ▼

Experience resort-style living at 1836 Whitehall Drive! Inspired by the warm breeze and seaside elegance of a tranquil island paradise, this new custom home by Urban Perc...

  • 5 Beds
  • 7 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
1773 Walnut Avenue, Winter Park image
1773 Walnut Avenue, Winter Park $2,725,000

Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined...

  • 5 Beds
  • 5 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
648 Worthington Drive, Winter Park image
648 Worthington Drive, Winter Park $2,700,000

Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable p...

  • 5 Beds
  • 5 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
1754 Taylor Avenue, Winter Park image
1754 Taylor Avenue, Winter Park $2,569,999

Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredibl...

  • 5 Beds
  • 5 Baths
  • Orange Grove Sub SubDv.
  • 32789 Zip Code
1823 Sunset Drive, Winter Park image
1823 Sunset Drive, Winter Park $2,549,000

Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of time...

  • 5 Beds
  • 5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
450 Lakewood Drive, Winter Park image
450 Lakewood Drive, Winter Park $2,500,000

Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within wal...

  • 5 Beds
  • 6 Baths
  • Osceola Shores Sec 03 SubDv.
  • 32789 Zip Code
541 W Canton Avenue, Winter Park image
541 W Canton Avenue, Winter Park $2,495,000 ▼

Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orl...

  • 4 Beds
  • 4 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
926 Enclave Place, Winter Park image
926 Enclave Place, Winter Park $2,475,000 ▲

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
946 Enclave Place, Winter Park image
946 Enclave Place, Winter Park $2,375,000 ▲

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
938 Enclave Place, Winter Park image
938 Enclave Place, Winter Park $2,300,000 ▲

Pre-Construction. To be built. Thoughtfully designed with a refined coastal-modern farmhouse aesthetic, this exceptional custom residence at 938 Enclave Place pairs timel...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
1840 Laurel Road, Winter Park image
1840 Laurel Road, Winter Park $2,299,000 ▲

Under Construction. Experience modern luxury in this exceptional new construction residence by LUIH Luxury Homes, scheduled for completion in December 2026.Offering 5 bed...

  • 5 Beds
  • 5 Baths
  • Charmont SubDv.
  • 32789 Zip Code
930 Enclave Place, Winter Park image
930 Enclave Place, Winter Park $2,275,000 ▲

Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneat...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
1885 Temple Drive, Winter Park image
1885 Temple Drive, Winter Park $2,195,000 ▼

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...

  • 5 Beds
  • 4 Baths
  • Lugano Terrace SubDv.
  • 32789 Zip Code
1133 Bella Lago Cove, Winter Park image
1133 Bella Lago Cove, Winter Park $2,100,000

A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custo...

  • 3 Beds
  • 2 Baths
  • 32792 Zip Code
914 Enclave Place, Winter Park image
914 Enclave Place, Winter Park $2,070,000 ▲

Pre-Construction. To be built. Absolutely — I would make the opening feel **more elevated, architectural, and luxury-focused**, while still keeping it MLS-friendly and in...

  • 5 Beds
  • 5 Baths
  • The Enclave Winter Park SubDv.
  • 32792 Zip Code
240 N Phelps Avenue, Winter Park image
240 N Phelps Avenue, Winter Park $2,050,000 ▼

A striking expression of modern luxury, this brand-new residence offers nearly 3,000 square feet of thoughtfully designed living space in one of Winter Park's most desira...

  • 5 Beds
  • 5 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
525 S Lakemont Avenue, Winter Park image
525 S Lakemont Avenue, Winter Park $1,999,990 ▼

Thoughtfully designed with an uncompromising commitment to quality, craftsmanship, and detail, this exceptional new construction residence is an expression of luxury livi...

  • 4 Beds
  • 4 Baths
  • Kenilworth Shores Sec 01 SubDv.
  • 32792 Zip Code
922 N Pennsylvania Avenue, Winter Park image
922 N Pennsylvania Avenue, Winter Park $1,995,000

Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated ...

  • 4 Beds
  • 4 Baths
  • Tantum Add SubDv.
  • 32789 Zip Code
751 Pansy Avenue, Winter Park image
751 Pansy Avenue, Winter Park $1,950,000

Set along one of Winter Park’s charming brick streets just steps from Park Avenue, this beautifully maintained home pairs refined design with an exceptional location. Imp...

  • 3 Beds
  • 4 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
1420 Aloma Avenue, Winter Park image
1420 Aloma Avenue, Winter Park $1,949,500 ▼

Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs...

  • 3 Beds
  • 4 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
2260 Mulbry Drive, Winter Park image
2260 Mulbry Drive, Winter Park $1,925,000

Pre-Construction. To be built. Pre-Construction. To be built. Your Dream Home Is Ready To Be Built!! Pre-Construction Opportunity! Build-to-Suit! Buyers who act now can s...

  • 5 Beds
  • 4 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1702 Arbor Park Drive, Winter Park image
1702 Arbor Park Drive, Winter Park $1,900,000

Set along a charming, tree-lined street in Winter Park, this stunning new construction home brings together modern farmhouse character, thoughtfully designed interiors, a...

  • 4 Beds
  • 4 Baths
  • Conwill Estates SubDv.
  • 32789 Zip Code
2343 Versailles Avenue, Winter Park image
2343 Versailles Avenue, Winter Park $1,865,000

Built in 2017 and thoughtfully enhanced with over $130K in recent improvements, this modern and sleek Winter Park residence is tucked along a quiet dead-end street, offer...

  • 4 Beds
  • 4 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
1550 Palm Avenue, Winter Park image
1550 Palm Avenue, Winter Park $1,829,000

Under Construction. LUXURY NEW CONSTRUCTION IN WINTER PARK'S HIGHLY SOUGHT-AFTER TREE STREETS! Welcome to 1550 Palm Avenue, a thoughtfully designed new residence by LUIH ...

  • 4 Beds
  • 4 Baths
  • Lake Knowles Terrace 2nd Add SubDv.
  • 32789 Zip Code
281 Brewer Avenue, Winter Park image
281 Brewer Avenue, Winter Park $1,800,000

Short Sale. Welcome to this luxury, home in the heart of Winter Park. Less than a mile away from Park Ave. Winter Park that offers entertainment, restaurants, farmers mar...

  • 5 Beds
  • 5 Baths
  • Osceola Shores Sec 02 SubDv.
  • 32789 Zip Code
2032 Kimbrace Place, Winter Park image
2032 Kimbrace Place, Winter Park $1,800,000 ▼

A PRIVATE BALINESE RESORT IN THE HEART OF WINTER PARK 5 Bedrooms | 4 Bathrooms | 3,400+ SF|Saltwater Pool & Spa|Minutes to Park Avenue Welcome to a rare offering where ...

  • 5 Beds
  • 4 Baths
  • Kenilworth Shores Sec 03 SubDv.
  • 32792 Zip Code
1750 Carollee Lane, Winter Park image
1750 Carollee Lane, Winter Park $1,780,000 ▼

Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom...

  • 4 Beds
  • 4 Baths
  • Green Terrace V/140 Lot 3 Blk B SubDv.
  • 32789 Zip Code
621 Huntington Avenue, Winter Park image
621 Huntington Avenue, Winter Park $1,770,000 ▼

Experience elevated living in this fully transformed luxury residence in the heart of Winter Park, where design, premium finishes, and effortless functionality come toget...

  • 3 Beds
  • 4 Baths
  • Winter Park Rev SubDv.
  • 32789 Zip Code
1840 Anzle Avenue, Winter Park image
1840 Anzle Avenue, Winter Park $1,750,000

Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everyt...

  • 4 Beds
  • 3 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
2525 Lafayette Avenue, Winter Park image
2525 Lafayette Avenue, Winter Park $1,749,000

Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brin...

  • 4 Beds
  • 4 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1840 Bryan Avenue, Winter Park image
1840 Bryan Avenue, Winter Park $1,725,000

Welcome to modern luxury in the heart of Winter Park! This custom 2014-built estate rests on an expansive double lot in the highly sought-after Lakeview Terrace community...

  • 4 Beds
  • 4 Baths
  • Lakeview Terrace SubDv.
  • 32789 Zip Code
2914 Reef Knot Place, Winter Park image
2914 Reef Knot Place, Winter Park $1,725,000

Welcome to an exceptional lakefront home in the gated community of Lake Florence Preserve, where luxury, space, and lifestyle come together in the heart of Winter Park. T...

  • 6 Beds
  • 6 Baths
  • Lake Florence Preserve SubDv.
  • 32792 Zip Code
723 Symonds Avenue, Winter Park image
723 Symonds Avenue, Winter Park $1,700,000 ▼

Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-...

  • 4 Beds
  • 4 Baths
  • Horton Aaron SubDv.
  • 32789 Zip Code
2308 Mulbry Drive, Winter Park image
2308 Mulbry Drive, Winter Park $1,699,000

Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet ...

  • 4 Beds
  • 4 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1903 N Park Avenue, Winter Park image
1903 N Park Avenue, Winter Park $1,649,000 ▼

Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park...

  • 4 Beds
  • 4 Baths
  • Twin Acres SubDv.
  • 32789 Zip Code
1570 Palmer Avenue, Winter Park image
1570 Palmer Avenue, Winter Park $1,640,000 ▼

Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functiona...

  • 4 Beds
  • 4 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
2407 Lafayette Avenue, Winter Park image
2407 Lafayette Avenue, Winter Park $1,625,000

Discover this exceptional custom-designed modern pool home, ideally situated in one of Winter Park's most sought-after neighborhoods. Located on a quiet street, this spac...

  • 5 Beds
  • 5 Baths
  • Fontainebleau SubDv.
  • 32789 Zip Code
1257 Wading Waters Circle, Winter Park image
1257 Wading Waters Circle, Winter Park $1,600,000

Welcome to luxury living in Hawks Crest, Winter Park’s only guard-gated community. This exceptional six-bedroom Del Rio floor plan sits on one of the neighborhood’s most ...

  • 6 Beds
  • 5 Baths
  • Waters Edge At Hawks Crest SubDv.
  • 32792 Zip Code
2207 Kindel Avenue, Winter Park image
2207 Kindel Avenue, Winter Park $1,600,000

WELCOME TO LAKEFRONT LUXURY ON LAKE BELL. This exceptional custom residence brings together refined craftsmanship and design, and an extraordinary waterfront setting in t...

  • 3 Beds
  • 3 Baths
  • Albert Lee Ridge Annex SubDv.
  • 32789 Zip Code
250 Killarney, Winter Park image
250 Killarney, Winter Park $1,600,000

This home is an adorable 4 Bed 3.5 Bath Home in the heart of Winter Park. You will feel right at home the moment you step in. lovely kitchen showcases gorgeous cabinets, ...

  • 4 Beds
  • 4 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
641 Northwood Circle, Winter Park image
641 Northwood Circle, Winter Park $1,599,000 ▼

Virtually Staged. 641 Northwood Circle is a rare opportunity to own newer construction in the heart of Winter Park at a newly repositioned price of $1,599,000. Tucked wit...

  • 3 Beds
  • 5 Baths
  • Winter Park Oasis SubDv.
  • 32789 Zip Code
1864 Grinnell Terrace, Winter Park image
1864 Grinnell Terrace, Winter Park $1,599,000

Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern in...

  • 5 Beds
  • 4 Baths
  • Fremar SubDv.
  • 32789 Zip Code
2430 Chantilly Avenue, Winter Park image
2430 Chantilly Avenue, Winter Park $1,598,000

Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impr...

  • 4 Beds
  • 4 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
462 W Lyman Avenue, Winter Park image
462 W Lyman Avenue, Winter Park $1,595,000

In the heart of Winter Park's vibrant Hannibal Square, this exceptional one-story residence, completed in 2022, offers the ideal blend of contemporary design, refined fin...

  • 3 Beds
  • 3 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
446 Melrose Avenue, Winter Park image
446 Melrose Avenue, Winter Park $1,595,000 ▼

A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence h...

  • 4 Beds
  • 2 Baths
  • Virginia Heights Rep SubDv.
  • 32789 Zip Code
1113 Via Del Mar, Winter Park image
1113 Via Del Mar, Winter Park $1,595,000

Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. ...

  • 3 Beds
  • 2 Baths
  • Tuscany Terrace SubDv.
  • 32789 Zip Code
708 Balmoral Road, Winter Park image
708 Balmoral Road, Winter Park $1,590,000 ▼

A rare elevated corner lot in the heart of Winter Park — walkable to Park Avenue's boutique shops and restaurants, and set on one of the area's most desirable streets. Su...

  • 4 Beds
  • 3 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
1526 Miller Avenue, Winter Park image
1526 Miller Avenue, Winter Park $1,574,900

New Construction! New photos coming soon! First photo is a rendering of the new home and the following photos are interiors of a similar model by the builder. Discover Mo...

  • 5 Beds
  • 5 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
341 E Reading Way, Winter Park image
341 E Reading Way, Winter Park $1,565,000 ▼

Virtually Staged. A rare opportunity to live on a quiet one-way street overlooking a park in the heart of Winter Park. Built in 2007 and meticulously maintained, this exc...

  • 4 Beds
  • 4 Baths
  • Charmont SubDv.
  • 32789 Zip Code
777 Halifax Avenue, Winter Park image
777 Halifax Avenue, Winter Park $1,500,000

Virtually Staged. Welcome to 777 Halifax Avenue — a 2021 David Weekley home that still feels brand new, tucked into one of Winter Park's most sought-after neighborhoods. ...

  • 5 Beds
  • 5 Baths
  • Park Manor First Add SubDv.
  • 32792 Zip Code
1841 Lake Spier Drive, Winter Park image
1841 Lake Spier Drive, Winter Park $1,498,000 ▼

Water skiers welcome. A rare opportunity to own a thoughtfully renovated lakefront residence in Winter Park. This home is perfectly situated between Winter Park, Baldwin ...

  • 3 Beds
  • 4 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
150 E Reading Way, Winter Park image
150 E Reading Way, Winter Park $1,449,000 ▼

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 cent...

  • 3 Beds
  • 3 Baths
  • Charmont SubDv.
  • 32789 Zip Code
1581 Magnolia Ave, Winter Park image
1581 Magnolia Ave, Winter Park $1,425,000 ▼

WOW! AN AMAZING NEW PRICE! SEE IT THIS WEEKEND! Perfectly situated along a picturesque brick lined street with sidewalks in the heart of Winter Park, this beautifully ref...

  • 4 Beds
  • 4 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
1546 Miller Avenue, Winter Park image
1546 Miller Avenue, Winter Park $1,419,900

Under Construction. Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community by one of the areas finest builders. This stunni...

  • 4 Beds
  • 4 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
1523 Miller Avenue, Winter Park image
1523 Miller Avenue, Winter Park $1,400,000 ▼

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 desi...

  • 5 Beds
  • 4 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
1473 Berkshire Avenue, Winter Park image
1473 Berkshire Avenue, Winter Park $1,399,000 ▼

LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 ...

  • 5 Beds
  • 4 Baths
  • Orwin Manor Westminster Sec SubDv.
  • 32789 Zip Code
1751 Goodrich Avenue, Winter Park image
1751 Goodrich Avenue, Winter Park $1,380,000 ▼

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 w...

  • 4 Beds
  • 4 Baths
  • Sylvan Heights SubDv.
  • 32789 Zip Code
1421 Chapman Circle, Winter Park image
1421 Chapman Circle, Winter Park $1,377,500 ▼

Welcome to 1421 Chapman Circle, an elegant Spanish-Mediterranean home nestled within the highly coveted Windsong community in the heart of Winter Park. From the moment yo...

  • 4 Beds
  • 4 Baths
  • Windsong Elizabeths Walk 43/81 SubDv.
  • 32789 Zip Code
1320 Orchid Avenue, Winter Park image
1320 Orchid Avenue, Winter Park $1,350,000

Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Or...

  • 4 Beds
  • 4 Baths
  • Elizabeth Heights Sub SubDv.
  • 32789 Zip Code
1445 Via Sangro Place, Winter Park image
1445 Via Sangro Place, Winter Park $1,350,000

Virtually Staged. Welcome to your dream home in the highly sought-after Lakeside Estates neighborhood in Winter Park! This elegant 6-bedroom, 5-bathroom, 2 laundry rooms ...

  • 6 Beds
  • 6 Baths
  • Lakeside Estates SubDv.
  • 32792 Zip Code
720 Pansy Avenue, Winter Park image
720 Pansy Avenue, Winter Park $1,350,000

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 residen...

  • 3 Beds
  • 4 Baths
  • Villa View Park SubDv.
  • 32789 Zip Code
1881 Lake Spier Drive, Winter Park image
1881 Lake Spier Drive, Winter Park $1,350,000

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 b...

  • 3 Beds
  • 2 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
1117 Wading Waters Circle, Winter Park image
1117 Wading Waters Circle, Winter Park $1,325,000 ▼

Welcome to an exceptional opportunity in Waters Edge at Hawks Crest, one of Winter Park's premier gated, resort-style communities. Positioned on a desirable premium lot w...

  • 6 Beds
  • 4 Baths
  • Waters Edge At Hawks Crest SubDv.
  • 32792 Zip Code
952 Moss Lane, Winter Park image
952 Moss Lane, Winter Park $1,319,950

Virtually Staged. Brand new Roof and HVAC systems in 2025 and all new windows 2026. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park t...

  • 4 Beds
  • 5 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
1922 Hammerlin Avenue, Winter Park image
1922 Hammerlin Avenue, Winter Park $1,300,000

WELCOME TO CONTEMPORARY LUXURY IN THE HEART OF WINTER PARK! This stunning two-story pool residence has been beautifully remodeled from top to bottom and offers high end d...

  • 3 Beds
  • 3 Baths
  • Edgewood Sub SubDv.
  • 32789 Zip Code
102 Bell Place, Winter Park image
102 Bell Place, Winter Park $1,299,000 ▼

Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for su...

  • 4 Beds
  • 4 Baths
  • Eastgate Sub SubDv.
  • 32792 Zip Code
240 Killarney Drive, Winter Park image
240 Killarney Drive, Winter Park $1,275,000

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 pri...

  • 3 Beds
  • 3 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
2015 Summerfield Road, Winter Park image
2015 Summerfield Road, Winter Park $1,262,500 ▼

Welcome to one of Winter Park's most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Completely reimagined and renovated,...

  • 4 Beds
  • 4 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
230 Killarney Drive, Winter Park image
230 Killarney Drive, Winter Park $1,250,000

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 pri...

  • 4 Beds
  • 1 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
120 Broadview Avenue, Winter Park image
120 Broadview Avenue, Winter Park $1,250,000 ▼

Rare lakefront opportunity on the beautiful pristine Lake Killarney in the heart of Winter Park! Build your dream home on this coveted corner lot graced by original brick...

  • 3 Beds
  • 2 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
1870 Staunton Avenue, Winter Park image
1870 Staunton Avenue, Winter Park — Deep Roots Construction $1,250,000

Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one o...

  • 4 Beds
  • 4 Baths
  • Karolina On Killarney SubDv.
  • 32789 Zip Code
Winter Park image
Winter Park $1,249,900

Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is ca...

  • 4 Beds
  • 4 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
1600 S Pennsylvania Avenue, Winter Park image
1600 S Pennsylvania Avenue, Winter Park $1,150,000 ▼

Welcome to this charming 3 bedroom, 2 bath home located in the highly desirable area of Winter Park. Situated on an oversized lot, this property offers both comfort and s...

  • 3 Beds
  • 2 Baths
  • Banks Colonial Estates SubDv.
  • 32789 Zip Code
1220 Howell Branch Road, Winter Park image
1220 Howell Branch Road, Winter Park $1,105,000 ▼

A RARE WINTER PARK RENOVATION OPPORTUNITY DIRECTLY ACROSS FROM HOWELL BRANCH PRESERVE! Situated on an approximately 0.23-acre lot, this distinctive 3-bedroom, 2-bath home...

  • 3 Beds
  • 2 Baths
  • Lake Maitland SubDv.
  • 32789 Zip Code
2227 Howard Drive, Winter Park image
2227 Howard Drive, Winter Park $1,100,000

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. ...

  • 3 Beds
  • 3 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1404 Border Drive, Winter Park image
1404 Border Drive, Winter Park $1,075,000 ▼

Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed buil...

  • 4 Beds
  • 4 Baths
  • Winter Park Village SubDv.
  • 32789 Zip Code
1448 Lake Florence Way, Winter Park image
1448 Lake Florence Way, Winter Park $1,049,900 ▼

Located in an intimate gated community of just 28 homes and minutes from Downtown Winter Park, this exceptional former K. Hovnanian model home features over $200,000 in b...

  • 5 Beds
  • 5 Baths
  • Lake Florence Preserve SubDv.
  • 32792 Zip Code
2702 Parkland Drive, Winter Park image
2702 Parkland Drive, Winter Park $1,049,000 ▼

Welcome to this beautifully updated Winter Park home, perfectly positioned on a desirable corner lot and zoned for Audubon Park K-8 and Winter Park High School. With 5 be...

  • 5 Beds
  • 3 Baths
  • Parklando SubDv.
  • 32789 Zip Code
Like or Share

Address Search

Realtor David MyersDavid Myers 407-801-3286
Your Winter Park Real Estate Expert

Popular Winter Park Searches

  • 25 Latest Winter Park Listings
  • Winter Park Commercial
  • Winter Park Condos
  • Winter Park Foreclosures
  • Winter Park Gated Homes
  • Winter Park Land
  • Winter Park Luxury Homes
  • Winter Park New Construction
  • Winter Park No HOA Homes
  • Winter Park Pool Homes
  • Winter Park Single Family Homes
  • Winter Park Townhomes
  • Winter Park Waterfront Homes

Winter Park Interactive Map Search

Winter Park Interactive Real Estate Map Search

ALL about Winter Park!

  • About Winter Park
  • Park Avenue
  • Winter Park Apartments
  • Winter Park Events
  • Winter Park Golf
  • Winter Park Grocery
  • Winter Park Hospitals
  • Winter Park Parks
  • Winter Park Restaurants
  • Winter Park Schools
  • Winter Park Shopping
  • Winter Park - Wiki Page
  • Where is Winter Park
  • Orange County Contacts
  • City of Winter Park Site

Communities Adjacent to Winter Park

  • Baldwin Park
  • College Park
  • Downtown Orlando
  • Maitland
  • UCF Area

Get Ziro-ed In

  • Sellers - Get Your Winter Park Homes Value
  • Sellers - Save Thousands on Your Listing
  • Buyers - Get Your Winter Park Market Report
  • Buyers - Get a Pre-Qualified for a Mortgage
  • Buyers - Get Get Thousands Back
  • Agents - Get Your Career Going with Ziro

About Florida Neighborhood Realty powered by Ziro Realty

  • Visit Our Other Sites:
  • NonaOrlandoProperties.com
  • MyOrlandoVacationHome.com

David Myers - Broker Associate
Florida Neighborhood Realty Team
Ziro Realty, LLC
549B Water Street
Celebration, FL 34747
Phone/Text: 407.801.3286
Web: FloridaNeighborhoodRealty.com
Stay Updated: Subscribe to Our Blog RSS Feed

Realtor, MLS, and Equal Housing Opportunity logos

© Florida Neighborhood Realty LLC - All Rights Reserved

Site Support

  • About Us
  • Facebook
  • Terms of Use
  • Contact Us
  • Instagram
  • Privacy Policy
  • Office Listings
  • Neighborhood Blog
  • AI & Data Disclaimer
IDX Real Estate Websites by
• Accessibility • Terms • Privacy