Homes For Sale In Grayson Square

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

It’s so easy to fall in love with this charming and beautifully updated home, perfectly tucked away in a secluded cul-de-sac while offering an incredibly convenient Winte...

Virtually Staged. Enjoy the best of Winter Park living from this charming 2-bedroom, 2-bath home just minutes from Park Avenue, Baldwin Park, Mills 50, Downtown Orlando, ...

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 ...

Virtually Staged. Zoned for Fantastic Winter Park Schools, this 4 bed, 2 bath recently renovated abode is waiting for you. Located on a quiet, tree-lined street, you can ...

SOVERA Realty is gifting the buyer a one-year home warranty! Discover a versatile investment opportunity in desirable Winter Park. This duplex offers a combined five bed...

Welcome home to Winter Park! This beautifully renovated 3-bedroom, 1.5-bath home offers the perfect combination of classic Florida living and extensive modern updates. Mu...

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...

Welcome to 2873 Old Castle Drive, an exceptional property located within the sought-after gated community of Bear Gully Pointe in Winter Park. Nestled along the shores o...

Bright, airy, and designed for a resort living! Welcome to a turn-key Winter Park Pine home where everyday life feels like a getaway! From the moment you enter, you will ...

Mid-century style meets modern convenience in this beautifully updated Winter Park home, offering a move in opportunity with no HOA. Extensively improved since 2022, the ...

Completely renovated and move-in ready, this beautifully updated Winter Park home offers a fresh, modern interior without the hassle of renovations. The brand-new kitchen...

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...

Great investment opportunity in Winter Park. 4 bedroom 2.5 bathroom. Large covered patio overlooks huge completely fenced back yard. New roof 2025, HVAC system 2020, w...

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

UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, a...

Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friends...

Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors f...

This exceptional homesite on Arbor Ridge sits in one of Winter Park's most prestigious and tightly held residential pockets—where elegant estates, mature canopy trees, an...

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. ...

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

Welcome to this beautifully updated 4-bedroom, 2-bath pool home located in the highly desirable Winter Woods community of Winter Park. From the moment you step inside, yo...

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...

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 ...

Exceptional Winter Park Opportunity with In-Law Suite & Income Potential Discover the opportunity to own a versatile property in one of Central Florida’s most desirabl...

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...

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

Come see this 3 bedroom 2 bath split plan home. All tile throughout home. Granite kitchen countertops. Eat in area in kitchen. Kitchen bar opens to great room. Huge cor...

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

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, ...

Welcome home to this adorable and beautifully updated 3-bedroom, 2-bathroom home in the heart of Winter Park! From the moment you arrive, the cheerful teal front door add...

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...

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...

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 ...

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...

Welcome to 2181 Linden Road, where modern updates meet the everyday convenience of Winter Park living. Thoughtfully renovated and designed with flexibility in mind, this ...

This "Investment Opportunity" duplex is centrally located on a quiet, tree lined, brick street, close to shopping, restaurants, downtown Winter Park, Rollins College & Me...

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...

Welcome to this charming 2 bedroom, 2 bath home, with light and bright open floor plan, spacious rooms and many updates and upgrades. Roof was replaced (2019), new A/C (...

An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer...

Completely Remodeled 2026 | Single-Story | Prime Location | Dual Suites | The redesigned kitchen features 42" shaker cabinetry, Calcutta quartz countertops, and new stain...

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...

Welcome to this fully renovated four-bedroom, two-bathroom pool home offering close to 2,000 square feet of beautifully updated living space on an expansive .36-acre pie-...

Welcome to 2333 Westminster Court, a stunningly reimagined residence that perfectly captures the effortless elegance of Winter Park living. A thoughtful and meticulous re...

Welcome home to 2112 Eastbrook Blvd, a fully remodeled gem tucked into the sought-after Eastbrook neighborhood of Winter Park! This 3-bedroom, 2-bathroom home has been...

Welcome to 1621 Chestnut Avenue, ideally situated in the heart of Winter Park's coveted "Tree Streets" neighborhood. Offered at $899,000, this single-story block home sit...

Welcome to this beautifully maintained four-bedroom, three-bathroom home offering over 2,000 square feet of thoughtfully designed living space in desirable Winter Park co...

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...

Updated Winter Park home with 2,047 sq ft of heated/cooled living space, a huge backyard, and NO HOA. This is an owner-updated home—not a flip—with quality improvements c...

Virtually Staged. Gated Community | Dual Primary Suites | Main-Level Living | Located in Winter Park’s gated Hawks Crest community, this two-story home pairs a spacio...

Virtually Staged. Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful ...

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...

Modern Ranch Gem on a Corner Lot | 4 Bed | 2 Bath | 2,126 Sq Ft | Screened Pool | No HOA | Winter Park, FL Welcome to this beautiful 4-bedroom, 2-bathroom ranch-style ...

Virtually Staged. Welcome to one of the most uniquely positioned homes in the highly sought-after gated community of Hawk’s Crest. This former Meritage model home sits on...

LOCATION. LIFESTYLE. TIMELESS WINTER PARK CHARM. Discover an exceptional opportunity in Lake Knowles Terrace, where classic character, effortless comfort, and an enviable...

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

Nestled in Winter Park's Lake Bell Terrace neighborhood, this 3 bedroom, 2 bathroom home is located close to everything that makes Winter Park special, Park Avenue's shop...

Welcome home to this beautifully presented 4-bedroom, 3-bath home located in Winter Park Estates. Offering a comfortable single-story layout and solid block construction...

Welcome to this beautifully updated 3-bedroom, 2-bathroom home nestled in a quiet and desirable Winter Park neighborhood. From the moment you arrive, you’ll appreciate th...

Welcome to this beautifully maintained 1960s home nestled in one of Winter Park’s desirable neighborhoods, where classic charm meets thoughtful modern updates. Set along ...

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...

Charming 1950 block bungalow in sought-after Orwin Manor! This inviting 3-bedroom, 2-bath home sits on a generous corner lot with a side-load driveway and garage, offerin...

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

Completely renovated 3bed/2bath, split floorplan, single family home in the heart of Winter Park. With brand new roof, updated kitchen and bath, brand new stainless steel...

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

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...

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...

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...

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...

Welcome to a premier opportunity in the the coveted Winter Park. This beautifully maintained 4-bedroom, 2.5-bathroom home is located in The Meadows – an alcove in the gat...

Opportunity awaits in this 3-bedroom, 2-bath concrete block home located in the established Fairview Heights area of Winter Park. Offering 1,344 square feet of living spa...

Virtually Staged. Nestled on an OVERSIZED HOMESITE of well over half an acre in the sought-after Lake Ann Estates of Winter Park, this BEAUTIFULLY UPDATED 4-bedroom, 3-ba...

MOVE IN READY! New roof, new bathrooms, new kitchen, new floors, new electrical panels and more. Located in the beautiful lake community of Lake Waunatta Woods. Large ...

Welcome to 5316 Halyard Court, a beautifully updated pool home nestled in the heart of Winter Park. This move-in-ready residence offers the perfect blend of modern finish...

Welcome home to this charming 3-bedroom, 2-bathroom residence offering comfort, functionality, and the freedom of NO HOA! This inviting home features a desirable split-be...

A MUST SEE BEAUTIFUL WELL MAINTAINED POOL HOME by ORIGINAL OWNERS in SOUGHT AFTER WINTER PARK ZIPCODE & SCHOOLS. PICTURES PROVIDE a GREAT PORTRAYAL of the FLOORPLAN b...

Tucked away on a quiet street just minutes from the heart of Winter Park, this beautifully updated bungalow offers the perfect blend of character, modern updates, and fle...

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

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...

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

Opportunity meets location at 1871 Bryan Avenue, a well-positioned Winter Park property offering an approachable entry point into the highly sought-after 32789 area. Set ...

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

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

This is an Excellent split plan pool home. Tile floors in the Family room, Living Room, and Dining room keep with the Florida syle. The bedrooms feature wood floors in al...

Discover the epitome of comfortable living in this fantastic single-family home situated on a generous and spacious corner lot. This meticulously renovated property featu...

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...

Virtually Staged. Discover this spacious 3-bedroom, 2-bathroom home offers 1,483 sq ft of comfortable living space with a functional layout and plenty of room for everyda...

Welcome to this beautifully updated 3-bedroom, 2-bath home in beautiful Winter Park! This move-in-ready property features stylish wood-look tile flooring throughout, crea...

Okay, let's talk about this one. Yes, there's green carpet. Yes, it needs your vision. I know exactly what you're thinking right now. But hear me out, because this house ...

Virtually Staged. Welcome to a residence where timeless design meets modern sophistication in the highly sought-after Winter Park Pines community—one of Winter Park's mos...

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...

Virtually Staged. Conveniently located just minutes from I-4, downtown Orlando, and Winter Park, this versatile home offers the perfect blend of comfort, flexibility, and...

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 1562 Arbor Park Drive, a beautifully maintained four-bedroom, two-and-a-half-bath residence tucked along a charming brick street in the heart of Winter Park. T...

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...

Oversized corner lot in quiet neighborhood with highly desired Seminole County schools. Well-built block on slab four bedroom home with split floor plan. Enclosed large F...

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, ...

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 ...

Nestled within the gated community of Hawks Crest, this meticulously maintained two-story residence showcases over $70,000 in luxurious builder upgrades, blending timeles...