Central Florida › Orlando Metro › Orange County › Winter Park › NO HOA Winter Park Listings
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.
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...
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...
Pre-Construction. To be built. (NOTE: Photos show features and finishes representative of the construction budget and selection allowances. All tile, colors, stone, cabin...
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...
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...
Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park...
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...
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...
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...
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...
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...
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...
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...
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...
Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmans...
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...
Under Construction. Beautifully composed from every angle, this extraordinary residence captures something increasingly rare in new construction: a genuine sense of chara...
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in ...
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...
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,...
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...
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...
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...
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...
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...
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...
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...
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...
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...
Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-...
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...
An exceptional expression of contemporary luxury on Winter Park’s historic Park Avenue! This newly constructed residence presents a luxurious design and elevated craftsma...
Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined...
Under Construction. Located in the Kenilworth Shores neighborhood, this stunning new residence brings an elevated level of new construction to an increasingly desirable p...
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...
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-...
Sophisticated Lakeside Living in the Heart of Winter Park! Experience the pinnacle of Florida luxury in this meticulously renovated estate, perfectly situated within wal...
Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, an...
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...
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'...
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 ...
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...
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 ...
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...
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...
Under Construction. Anticipated for completion in January 2027, this new-construction luxury home in Winter Park's Kenilworth Shores neighborhood offers five bedrooms, 4....
Improved! Positioned on a charming brick-lined street in historic Winter Park adjacent to Windsong, this custom-built residence pairs solid architectural craftsmanship wi...
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...
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...
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...
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...
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 ...
Under Construction. NEW CONSTRUCTION – Under Construction. Welcome to Winter Park! This stunning modern residence is meticulously designed and ideally located near everyt...
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...
Under Construction. Nearly complete... be in for the holidays!!!!! Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringin...
Under Construction. In a coveted Winter Park enclave, this masterful LUIH residence balances contemporary grandeur with effortless livability. Spanning 2,500 square feet ...
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...
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...
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, ...
Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. ...
WELCOME TO LAKEFRONT LUXURY ON LAKE BELL. This exceptional custom residence brings together refined craftsmanship and design, and an extraordinary waterfront setting in t...
Architecture, design, and function come together with remarkable intention in this custom Winter Park residence designed by renowned architect Gary Hancock. From the impr...
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 ...
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...
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...
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...
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...
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...
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...
Virtually Staged. Now offered at $1,499,000. Attractive financing opportunities may be available to qualified buyers, including preferred lender financing incentives. Set...
WELCOME to this farmhouse-inspired residence combines timeless architectural character with modern luxury and thoughtful design. ***A welcome front porch leads to an im...
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...
LOCATION LOCATION LOCATION. Discover exceptional new construction in the heart of Winter Park. Completed in 2025, this stunning Mediterranean-inspired residence offers 5 ...
Modern Winter Park living meets exceptional convenience at this beautifully designed 2023 residence, ideally positioned near Park Avenue and just minutes from Downtown Or...
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...
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...
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...
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...
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. ...
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...
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...
English cottage–inspired architecture, enchanting gardens and a setting directly across from Lake Sylvan introduce this exquisitely renovated Winter Park residence. Set a...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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...
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 ...
David Myers 407-801-3286
Your Winter Park Real Estate Expert