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Central Florida › Orlando Metro › Orange County › Winter Park › NO HOA Winter Park Listings

Winter Park Homes with NO HOA

Don't like some HOA board telling what you can and cannot do on your property? Winter Park has plenty of homes that do not have an HOA. Below is a list of residential home listings that have been listed as having no HOA or an optional HOA.

Winter Park No HOA Homes for Sale

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
901 Golfview Terrace, Winter Park image
901 Golfview Terrace, Winter Park $6,795,000 ▼

Gorgeous custom five-bedroom, five-and-one-half-bath residence built by Maroon Fine Homes in 2023 and ideally positioned on arguably one of the most sought after location...

  • 5 Beds
  • 6 Baths
  • Golfview Terrace SubDv.
  • 32789 Zip Code
1011 Mckean Circle, Winter Park image
1011 Mckean Circle, Winter Park — Wooten Built $6,000,000

Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabin...

  • 5 Beds
  • 7 Baths
  • Palmer Park 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
1200 Via Salerno, Winter Park image
1200 Via Salerno, Winter Park $5,995,000

Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live...

  • 5 Beds
  • 6 Baths
  • Cloister Grove Sub SubDv.
  • 32789 Zip Code
1441 Grove Terrace, Winter Park image
1441 Grove Terrace, Winter Park $5,950,000

Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park...

  • 5 Beds
  • 6 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
2228 Azalea Place, Winter Park image
2228 Azalea Place, Winter Park $5,600,000

Virtually Staged. 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 l...

  • 5 Beds
  • 6 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
1166 Palmer Avenue, Winter Park image
1166 Palmer Avenue, Winter Park $5,500,000

Pre-Construction. To be built. PRE-CONSTRUCTION: Introducing an exceptional new construction residence by Nautilus Homes, ideally positioned in the heart of Winter Park n...

  • 5 Beds
  • 7 Baths
  • Palmer Ave Lakeside Prop SubDv.
  • 32789 Zip Code
2661 Via Tuscany, Winter Park image
2661 Via Tuscany, Winter Park $5,500,000 ▼

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
825 Palmer Avenue, Winter Park image
825 Palmer Avenue, Winter Park $5,195,900 ▲

Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of L...

  • 5 Beds
  • 7 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
617 N Interlachen Avenue, Winter Park image
617 N Interlachen Avenue, Winter Park $4,695,000

Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival e...

  • 11 Beds
  • 8 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
1631 Hillcrest Avenue, Winter Park image
1631 Hillcrest Avenue, Winter Park $4,500,000

Brand new construction (2023) on a beautifully sized .29± acre lot in the heart of Winter Park. This 5BR/5.5BA estate offers an open-concept layout with high ceilings, ab...

  • 5 Beds
  • 6 Baths
  • Ellno Willo SubDv.
  • 32789 Zip Code
231 Chelton Circle, Winter Park image
231 Chelton Circle, Winter Park $4,500,000 ▼

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 $4,350,000 ▼

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
702 Via Bella, Winter Park image
702 Via Bella, Winter Park $4,090,000 ▼

Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmans...

  • 4 Beds
  • 6 Baths
  • Palmer Ave Lakeside Prop SubDv.
  • 32789 Zip Code
540 N Pennsylvania Avenue, Winter Park image
540 N Pennsylvania Avenue, Winter Park $3,950,000

Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density R...

  • 4 Beds
  • 2 Baths
  • Winter Park 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
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
1441 Cardinal Court, Winter Park image
1441 Cardinal Court, Winter Park $3,600,000 ▼

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
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
1600 Legion Drive, Winter Park image
1600 Legion Drive, Winter Park $3,495,000

Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a produc...

  • 5 Beds
  • 6 Baths
  • Green Oaks Rep SubDv.
  • 32789 Zip Code
662 Granville Drive, Winter Park image
662 Granville Drive, Winter Park $3,495,000

Timeless elegance meets effortless modern living in this exceptional five-bedroom, 5.5-bath residence in Park Grove, one of Winter Park's most coveted neighborhoods. Desi...

  • 5 Beds
  • 6 Baths
  • Park Grove SubDv.
  • 32789 Zip Code
1742 Temple Drive, Winter Park image
1742 Temple Drive, Winter Park $3,395,995 ▼

The Art of Living Well: A New Chapter at Moon Haus, Winter Park, Florida Moon Haus is a ground-up, virtually new modern luxury home in Winter Park, Florida, minutes fr...

  • 4 Beds
  • 5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
1751 Glencoe Road, Winter Park image
1751 Glencoe Road, Winter Park $3,390,000

Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rar...

  • 5 Beds
  • 7 Baths
  • Forest Hills SubDv.
  • 32789 Zip Code
1761 Legion Drive, Winter Park image
1761 Legion Drive, Winter Park $3,265,000

Nearly half an acre in the heart of Winter Park. Set on a 0.42-acre oversized corner lot in Green Oaks, this custom 5-bedroom, 5.5-bath residence offers what nearby new c...

  • 5 Beds
  • 6 Baths
  • Green Oaks Rep 02 SubDv.
  • 32789 Zip Code
2823 Parkland Circle, Winter Park image
2823 Parkland Circle, Winter Park $3,250,000

JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, thi...

  • 5 Beds
  • 6 Baths
  • Lake Forest Park SubDv.
  • 32789 Zip Code
1825 Whitehall Drive, Winter Park image
1825 Whitehall Drive, Winter Park $3,195,000

1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed stone, a stately brick entry, and striking black-framed windows define its European-inspired ar...

  • 4 Beds
  • 6 Baths
  • Kenilworth Shores Sec 06 SubDv.
  • 32789 Zip Code
2119 Howard Drive, Winter Park image
2119 Howard Drive, Winter Park $3,195,000

Pre-Construction. To be built. A striking new custom residence by FG Schaub Custom Homes, located at 2119 Howard Drive in Winter Park. This exceptional 5-bedroom, 5.5-bat...

  • 5 Beds
  • 6 Baths
  • Timberlane SubDv.
  • 32789 Zip Code
532 Langholm Drive, Winter Park image
532 Langholm Drive, Winter Park $2,990,000

Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-...

  • 5 Beds
  • 5 Baths
  • Kenilworth Shores Sec 01 SubDv.
  • 32789 Zip Code
1821 Englewood Road, Winter Park image
1821 Englewood Road, Winter Park $2,950,000 ▼

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
1663 N Park Avenue, Winter Park image
1663 N Park Avenue, Winter Park $2,750,000

An exceptional expression of contemporary luxury on Winter Park’s historic Park Avenue! This newly constructed residence presents a luxurious design and elevated craftsma...

  • 4 Beds
  • 5 Baths
  • Dixie Terrace 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
1681 Woodland Avenue, Winter Park image
1681 Woodland Avenue, Winter Park $2,629,000

Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, th...

  • 5 Beds
  • 5 Baths
  • Comstock Park SubDv.
  • 32789 Zip Code
1760 Oakhurst Avenue, Winter Park image
1760 Oakhurst Avenue, Winter Park $2,500,000

Experience the pinnacle of modern luxury in this architectural masterpiece, perfectly situated in the highly coveted City of Winter Park. Boasting five bedrooms and four-...

  • 5 Beds
  • 5 Baths
  • Jenkins Second Add 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
1441 Palm Avenue, Winter Park image
1441 Palm Avenue, Winter Park $2,449,000

Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, an...

  • 5 Beds
  • 5 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
1803 Barker Drive, Winter Park image
1803 Barker Drive, Winter Park $2,190,000

A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning pro...

  • 4 Beds
  • 3 Baths
  • South Lakemont Shores SubDv.
  • 32789 Zip Code
1271 Palmer Avenue, Winter Park image
1271 Palmer Avenue, Winter Park $2,125,000 ▼

Set on a generous corner lot, this stunning single-story pool home in Winter Park has been beautifully remodeled and offers the kind of effortless, one-level living that'...

  • 4 Beds
  • 5 Baths
  • J Kronenberger Sub SubDv.
  • 32789 Zip Code
1355 Hibiscus Avenue, Winter Park image
1355 Hibiscus Avenue, Winter Park $2,100,000

Virtually Staged. Situated along one of Winter Park's charming, tree-lined brick streets, this beautifully maintained traditional residence offers over 4,100 square feet ...

  • 5 Beds
  • 6 Baths
  • Lake Knowles Terrace Add 02 SubDv.
  • 32789 Zip Code
555 E Lake Sue Avenue, Winter Park image
555 E Lake Sue Avenue, Winter Park $2,000,000 ▼

Welcome to Timberlane Shores, one of Winter Park’s most desirable and established neighborhoods. This beautifully updated home sits on over a third of an acre with deeded...

  • 4 Beds
  • 4 Baths
  • Lake Virgina Shores SubDv.
  • 32789 Zip Code
1133 Bella Lago Cove, Winter Park image
1133 Bella Lago Cove, Winter Park $1,999,900 ▼

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

  • 3 Beds
  • 2 Baths
  • 32792 Zip Code
240 N Phelps Avenue, Winter Park image
240 N Phelps Avenue, Winter Park $1,999,900 ▼

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
2007 Edwin Boulevard, Winter Park image
2007 Edwin Boulevard, Winter Park $1,995,000

Virtually Staged. Pre-Construction. To be built. POOL + SAUNA • DOUBLE PRIMARY SUITES • 3-CAR GARAGE • CUSTOM NEW CONSTRUCTION IN WINTER PARK Pool, sauna, double prima...

  • 4 Beds
  • 4 Baths
  • Eastgate Sub SubDv.
  • 32792 Zip Code
513 Dunraven Drive, Winter Park image
513 Dunraven Drive, Winter Park $1,950,000

Under Construction. Anticipated for completion in January 2027, this new-construction luxury home in Winter Park's Kenilworth Shores neighborhood offers five bedrooms, 4....

  • 5 Beds
  • 5 Baths
  • Kenilworth Shores Sec 03 SubDv.
  • 32792 Zip Code
1398 Grove Terrace, Winter Park image
1398 Grove Terrace, Winter Park $1,949,000

Improved! Positioned on a charming brick-lined street in historic Winter Park adjacent to Windsong, this custom-built residence pairs solid architectural craftsmanship wi...

  • 4 Beds
  • 4 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
1951 Winter Park Road, Winter Park image
1951 Winter Park Road, Winter Park $1,949,000 ▼

Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts and set along the brick-paved streets of histor...

  • 4 Beds
  • 4 Baths
  • Charmont SubDv.
  • 32789 Zip Code
2614 Parkland Drive, Winter Park image
2614 Parkland Drive, Winter Park $1,890,000

PRICED BELOW APPRAISED VALUE | FULLY REMODELED WINTER PARK POOL HOME Pre-approval or proof of funds required in advance of showing. A rare opportunity to own more t...

  • 4 Beds
  • 4 Baths
  • Parklando 03 SubDv.
  • 32789 Zip Code
751 Pansy Avenue, Winter Park image
751 Pansy Avenue, Winter Park $1,875,000 ▼

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
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
922 N Pennsylvania Avenue, Winter Park image
922 N Pennsylvania Avenue, Winter Park $1,795,000 ▼

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
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
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
2613 Lafayette Avenue, Winter Park image
2613 Lafayette Avenue, Winter Park $1,699,900

Under Construction. Nearly complete... be in for the holidays!!!!! Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringin...

  • 4 Beds
  • 4 Baths
  • Charmont 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
2343 Versailles Avenue, Winter Park image
2343 Versailles Avenue, Winter Park $1,675,000 ▼

This modern and sleek Winter Park residence, with over $130K of improvements, is tucked along a quiet dead-end street, offering a functional, open floorplan in an excepti...

  • 4 Beds
  • 4 Baths
  • Fontainebleau 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
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
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
2207 Kindel Avenue, Winter Park image
2207 Kindel Avenue, Winter Park $1,575,000 ▼

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
2430 Chantilly Avenue, Winter Park image
2430 Chantilly Avenue, Winter Park $1,550,000 ▼

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
1350 Lyndale Boulevard, Winter Park image
1350 Lyndale Boulevard, Winter Park $1,499,000

Photos coming soon. Experience timeless elegance and exceptional living in the heart of Winter Park! Nestled along a charming, quiet brick-lined street just moments from ...

  • 4 Beds
  • 4 Baths
  • Dixie Terrace SubDv.
  • 32789 Zip Code
1570 Palmer Avenue, Winter Park image
1570 Palmer Avenue, Winter Park $1,485,000 ▼

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
446 Melrose Avenue, Winter Park image
446 Melrose Avenue, Winter Park $1,475,000 ▼

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
462 W Lyman Avenue, Winter Park image
462 W Lyman Avenue, Winter Park $1,450,000 ▲

Located in the downtown corridor within 2 blocks of Park Avenue, this exceptional one-story Mid-Century Modern residence completed in 2022 offers the ideal blend of conte...

  • 3 Beds
  • 3 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
777 Halifax Avenue, Winter Park image
777 Halifax Avenue, Winter Park $1,449,000 ▼

Virtually Staged. Newly priced and ready for its next owner — this 2021-built Winter Park residence in sought-after Park Manor blends modern luxury with everyday livabili...

  • 5 Beds
  • 5 Baths
  • Park Manor First Add SubDv.
  • 32792 Zip Code
1546 Miller Avenue, Winter Park image
1546 Miller Avenue, Winter Park $1,429,900 ▲

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

  • 4 Beds
  • 4 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
2237 Woodcrest Drive, Winter Park image
2237 Woodcrest Drive, Winter Park $1,425,000

Under Construction. Nestled on a quiet street on an oversized homesite in Winter Park, this stunning new construction home by David Weekley Homes blends timeless design w...

  • 4 Beds
  • 5 Baths
  • Kenilworth Estates SubDv.
  • 32792 Zip Code
641 Northwood Circle, Winter Park image
641 Northwood Circle, Winter Park $1,425,000 ▼

Virtually Staged. Now offered at $1,499,000. Attractive financing opportunities may be available to qualified buyers, including preferred lender financing incentives. Set...

  • 3 Beds
  • 5 Baths
  • Winter Park Oasis SubDv.
  • 32789 Zip Code
1737 Indiana Avenue, Winter Park image
1737 Indiana Avenue, Winter Park $1,399,900 ▲

WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an im...

  • 4 Beds
  • 4 Baths
  • Lawndale 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
1473 Berkshire Avenue, Winter Park image
1473 Berkshire Avenue, Winter Park $1,369,000 ▼

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
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
1939 Woodcrest Drive, Winter Park image
1939 Woodcrest Drive, Winter Park $1,349,000

Welcome to refined modern living in the heart of Winter Park. Meticulously crafted in 2020, this stunning two story residence showcases four bedrooms, three full baths, a...

  • 4 Beds
  • 4 Baths
  • Acreage SubDv.
  • 32792 Zip Code
150 E Reading Way, Winter Park image
150 E Reading Way, Winter Park $1,349,000 ▼

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
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
720 Pansy Avenue, Winter Park image
720 Pansy Avenue, Winter Park $1,295,000 ▼

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
120 Broadview Avenue, Winter Park image
120 Broadview Avenue, Winter Park $1,250,000

SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. ...

  • 3 Beds
  • 2 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
2015 Summerfield Road, Winter Park image
2015 Summerfield Road, Winter Park $1,250,000 ▼

Recently appraised at $1,250,000! Welcome to one of Winter Park’s most impressive move-in-ready homes, where luxury, comfort, and location come together seamlessly. Co...

  • 4 Beds
  • 4 Baths
  • Kenilworth Shores Sec 07 SubDv.
  • 32792 Zip Code
1940 Magnolia Avenue, Winter Park image
1940 Magnolia Avenue, Winter Park $1,190,000

New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This s...

  • 4 Beds
  • 4 Baths
  • Temple Terrace Annex SubDv.
  • 32792 Zip Code
1500 Harris Circle, Winter Park image
1500 Harris Circle, Winter Park $1,175,000

English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set a...

  • 3 Beds
  • 3 Baths
  • Sylvan Lake Shores SubDv.
  • 32789 Zip Code
240 Killarney Drive, Winter Park image
240 Killarney Drive, Winter Park $1,175,000 ▼

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
230 Killarney Drive, Winter Park image
230 Killarney Drive, Winter Park $1,150,000 ▼

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
1922 Hammerlin Avenue, Winter Park image
1922 Hammerlin Avenue, Winter Park $1,095,000 ▲

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
1517 Harmon Avenue, Winter Park image
1517 Harmon Avenue, Winter Park $1,049,000 ▼

Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining...

  • 4 Beds
  • 4 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
443 Broadview Avenue, Winter Park image
443 Broadview Avenue, Winter Park $999,000 ▼

A truly special property in Winter Park’s 32789 zip code, this renovated 1925 Craftsman is filled with character and charm. Set on an oversized 0.36-acre lot just one hom...

  • 4 Beds
  • 3 Baths
  • Killarney Estates SubDv.
  • 32789 Zip Code
616 Brechin Drive, Winter Park image
616 Brechin Drive, Winter Park $999,000 ▼

Welcome to your fully reimagined Florida home. Among tree-canopied streets in the desired Kenilworth Shores neighborhood, this mid-century modern ranch home was completel...

  • 4 Beds
  • 5 Baths
  • Kenilworth Shores Sec 04 SubDv.
  • 32792 Zip Code
1404 Border Drive, Winter Park image
1404 Border Drive, Winter Park $998,000 ▼

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
2330 Westminster Ct., Winter Park image
2330 Westminster Ct., Winter Park $985,000

Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigne...

  • 5 Beds
  • 3 Baths
  • Glencoe Sub SubDv.
  • 32789 Zip Code
1611 Chestnut Avenue, Winter Park image
1611 Chestnut Avenue, Winter Park $985,000

Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering near...

  • 4 Beds
  • 4 Baths
  • Lake Knowles Terrace SubDv.
  • 32789 Zip Code
1411 Devon Road, Winter Park image
1411 Devon Road, Winter Park $950,000

Experience the charm of Winter Park living in this beautifully renovated Orwin Manor residence, where more than $41,000 in luxurious upgrades complement timeless characte...

  • 2 Beds
  • 2 Baths
  • Orwin Manor Westminster SubDv.
  • 32789 Zip Code
913 Moss Lane, Winter Park image
913 Moss Lane, Winter Park $950,000

913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park...

  • 3 Beds
  • 2 Baths
  • Maitland Shores First Add SubDv.
  • 32789 Zip Code
1220 Howell Branch Road, Winter Park image
1220 Howell Branch Road, Winter Park $950,000 ▼

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
471 Holt Avenue, Winter Park image
471 Holt Avenue, Winter Park $925,000 ▼

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential. THIS HOUSE IS AVAILABLE FOR LEASING OPTION. Discover the opportunity to own a versatile prop...

  • 4 Beds
  • 3 Baths
  • Winter Park SubDv.
  • 32789 Zip Code
3006 Northwood Boulevard, Winter Park image
3006 Northwood Boulevard, Winter Park $899,000 ▼

Reinvented from the ground up for modern living while honoring its 1953 mid-century modern roots, this 4-bedroom, 3-bath Winter Park home blends authentic MCM character w...

  • 4 Beds
  • 3 Baths
  • Northwood Terrace SubDv.
  • 32789 Zip Code
2572 Fifeshire Drive, Winter Park image
2572 Fifeshire Drive, Winter Park $875,000 ▼

Welcome to this warm and inviting home in the desirable Brookshire Heights neighborhood, ideally positioned on a corner lot along a beautiful street in a sought-after com...

  • 4 Beds
  • 3 Baths
  • Brookshire Heights 2nd Add SubDv.
  • 32792 Zip Code
618 Blairshire Circle, Winter Park image
618 Blairshire Circle, Winter Park $875,000 ▼

Virtually Staged. FULLY RENOVATED 4-BEDROOM, 3-BATH POOL HOME IN THE HEART OF WINTER PARK! this beautifully updated home sits on a spacious 9,915-square-foot lot surroun...

  • 4 Beds
  • 3 Baths
  • Brookshire Heights 4th Add SubDv.
  • 32792 Zip Code
120 Longbranch Road, Winter Park image
120 Longbranch Road, Winter Park $860,000

Virtually Staged. Set on nearly an acre in Winter Park, this stately two-story home offers five bedrooms and three and a half bathrooms across more than 3,200 square feet...

  • 5 Beds
  • 4 Baths
  • Lake Ann Estates Unit 3 SubDv.
  • 32792 Zip Code
2011 Harmon Avenue, Winter Park image
2011 Harmon Avenue, Winter Park $849,900

Under Construction. Welcome to your NEW Home! This residence to-be-built is a rare single story home. This bright open floor-plan features a large great room open to the ...

  • 4 Beds
  • 3 Baths
  • Lawndale SubDv.
  • 32789 Zip Code
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