Homes For Sale In Grayson Square

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...

Rare opportunity in Winter Park's 32789! Located on a quiet cul-de-sac in one of Central Florida's most sought-after ZIP codes, this spacious 4-bedroom, 2-bath home offer...

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...

This well-cared-for immaculate home features quality workmanship inside and out! The mature tropical oasis landscaping, cozy seating areas, and winding pathways make you ...

Virtually Staged. Opportunity Awaits in the Heart of Winter Park! Welcome to 7426 Blue Jacket Place, a 3-bedroom, 2-bathroom home that's ready for its next chapter. Nestl...

This WINTER PARK POOL HOME is set on a corner lot with entrances from both Palmer Avenue and Temple Drive. Located within Winter Park's exclusive J Kronenberger community...

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...

Virtually Staged. Imagine 7026 Hammock Way, recently enhanced with fresh interior paint throughout, establishing a bright and inviting atmosphere. The outdoor space inclu...

Don't miss this opportunity to own a beautifully updated home with a sought-after Winter Park address! Priced to sell, this move-in-ready 3-bedroom, 2-bath home offers th...

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...

Turnkey Charm in Winter Park! This beautifully remodeled 3-bedroom, 2-bathroom home offers the perfect blend of style and convenience. Step inside to find durable ceramic...

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...

Virtually Staged. 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 di...

Virtually Staged. 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 di...

Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter P...

Roof 2018 | HVAC 2020| Set on a deep, tree-canopied lot in one of Winter Park's most desirable established neighborhoods, this charming single-story concrete-block home b...

Located on one of Winter Park's picturesque brick streets in the highly desirable “Tree Streets”, this beautifully updated home offers incredible curb appeal with a circu...

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...

Welcome home to this stunningly renovated 4-bedroom, 2.5-bath with TWO additional rooms that can be used as an office space, playroom etc single-family residence located ...

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...

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...

Beautiful meticulously maintained 3-bedroom, 2-bath split floor plan home situated on a desirable corner lot in the established Glenmoor community. Move-in ready, this ho...

Virtually Staged. Welcome to 2223 Conifer Ave, recently enhanced with a new roof, fresh interior paint, and fresh exterior paint. The kitchen features all stainless steel...

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

Beautifully updated 4-bedroom, 2-bath pool home in Winter Park offering modern upgrades and flexible living space. The home features new tile flooring throughout, a fully...

LIGHTING FAST RESPONSE - FULLY RENOVATED 5-BEDROOM, 4-BATH WINTER PARK ESTATE Welcome to 724 Monmouth Way, a beautifully reimagined five-bedroom, four-bath estate design...

Virtually Staged. Built in 2021 by David Weekley Homes, this thoughtfully designed 5-bedroom, 4.5-bath residence delivers 3,109 square feet of refined, light-filled livin...

Positioned in one of Winter Park's most desirable neighborhoods, this exceptional French Mediterranean residence is just moments from Phelps Park, the Winter Park YMCA, L...

Life in Winter Park is about more than just where you live—it's about how you live. At 2803 Riddle Drive, that lifestyle comes together with an inviting open floor plan, ...

Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenienc...

Updated Winter Park home with major improvements already completed and no HOA! Located at 4965 Orange Ave., this move-in ready property offers a desirable Central Florida...

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...

Location, location, location. Wonderful home located in Winter Park besides Baldwin Park. Live in this home now - or purchase for the property and build your custom hom...

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

Handyman/Investor/Landlord special. Home is dated/all original and may need full rehab. 2 bedroom 1.5 jack and jill bath. Nice end unit on dead end street, huge culdesac...

**This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly paymen...

A pristine location in the Vias of Winter Park, this refined Santa Barbara-inspired Mediterranean estate rests on nearly half an acre — a rare double lot. A 2006 custom b...

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...

Discover the perfect place to call home! This beautiful 4-bedroom, 2-bath residence offers a spacious layout, a 2-car garage, and the freedom of no HOA. Conveniently loca...

Impeccably Renovated Turn-Key Oasis with a Resort-Style Backyard! No HOA with yard large enough for possible ADU. Welcome home to this meticulously updated 4-bedroom, 3-...

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...

Nested on a spacious, tree lined lot just steps from Lake Killarney, 2361 Roxbury Road offers a rare opportunity to create your dream home in one of Winter Park’s most co...

Motivated Seller ! First time on the market in over 60 years! Filled with decades of cherished family memories, this beloved home is ready for its next chapter. Locate...

PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the prop...

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...

Charming renovated bungalow on a brick street in the heart of Winter Park! Recently updated with new finishes and appliances throughout. Move in ready, no HOA, and just a...

Reimagined from the ground up for modern living while honoring its original mid-century modern heritage, this 1953 Winter Park residence pairs authentic MCM character wit...

Rare Waterfront Opportunity in Winter Park! Discover your own slice of Florida paradise with this waterfront gem offering 94 feet of direct canal frontage on Lake Bell fo...

Beautifully renovated three-bedroom, two-bath home in desirable Winter Park 32789. Extensively updated throughout, this move-in-ready home offers the perfect blend of mod...

MOTIVATED SELLER – QUICK CLOSE AVAILABLE! Welcome to this beautifully maintained 4-bedroom, 2-bath home in the desirable Kings Cove community of Winter Park. From the mom...

Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, ...

Discover the potential of this spacious 4-bedroom, 2.5-bath home located at 1564 Lawndale Cir in desirable Winter Park. Featuring a comfortable floor plan with generous l...

Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with NO HOA. Located conveniently to all major roads, shopping, schools and restauran...

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...

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,...

SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a...

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...

Virtually Staged. Discover space, comfort, and flexibility in this beautifully updated 4-bedroom, 2-bath home in the highly desirable Cedar Ridge community of Winter Park...

Virtually Staged. Nestled in the heart of Winter Park, just blocks from Park Avenue and Winter Park Village, this exceptional residence delivers the walkable lifestyle th...

Welcome to this stunning Taylor Morrison Boca model in the highly desirable Hawks Crest gated community. This beautifully maintained 4-bedroom, 2.5-bath home offers an ex...

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...

Welcome to 8433 Commander Cove, ideally situated on a quiet cul-de-sac in the highly sought-after Trinity Bay community. Upon entering this spacious home you're greeted b...

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...

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...

Discover this well maintained 3 bedroom, 2 bathroom home offering 1,676 sq ft of comfortable living space. The home features a spacious layout with inviting living and di...

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...

Completely reimagined and professionally renovated, this stunning Winter Park POOL home offers approximately 1,950 square feet of thoughtfully designed living space with ...

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...

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

A PRIVATE RESORT-STYLE SANCTUARY 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...

GREAT HOME & GREAT VALUE — home needs cosmetic work and some TLC - if you DIY you could have instant equity. Thoughtful floor plan with two living spaces and a screened-i...

Winter Park Luxury Awaits You! Welcome to your dream home—a stunning custom-built luxury residence offering the perfect blend of elegance, comfort, and modern design. Fe...

Just Reduced by $20,000! This is your chance to own a beautifully updated Winter Park home at an even better value. Come see it before it’s gone! Rare opportunity to o...

One or more photo(s) has been virtually staged. WINTER PARK 32789 in the highly sought-after Dommerich Elementary, Maitland Middle, and Winter Park High school district. ...

Private Lake Access & Exceptional Florida Living! Welcome to Trinity Bay, a charming community offering deeded access to Lake Burkett, a private 75-acre spring-fed ski la...

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...

Fully renovated 2 bedroom and 2 bathroom home with a bonus room, ideally located in the heart of Winter Park. Every detail has been updated, including new mechanical syst...

No-HOA home with NEW ROOF 2022 and dedicated HOME OFFICE/FLEX SPACE! This move-in-ready 3-bedroom, 2-bathroom residence offers 1,366 sq ft of smart living plus an bonus r...

Check out this private pool home in lovely Winter Park. Offers 4 bedrooms, 3 baths and a 2 car garage. Huge kitchen overlooking family room. Inside laundry room. Fenced b...

Welcome to your dream home in the highly sought-after community of Winter Park Pines! This beautifully maintained 4-bedroom, 3-bathroom residence offers 2,312 square feet...

Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. Located just minutes away from Downtown ...

Tucked away on a peaceful cut-de-sac in the heart of Winter Park, this striking modern residence offers a rare blend of privacy, walkability and refined design. A private...

**NEW CONSTRUCTION QUALITY | WALKABLE WINTER PARK | DESIGNER SMART HOME** This is not a remodel — it's a complete architectural transformation completed in September 2...

Step into this well maintained 3 bedroom 2 bath home located in a highly sought after Winter Park, Garden Lake Estates. Nestled in Seminole County, A rated school zone! T...

Step into timeless style and modern comfort in this stunning 3-bedroom, 3-bathroom Mid-Century Modern home nestled in the heart of Winter Park. Designed with character an...

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...

Been looking for a 4 bedroom home? Well, you have found it!!! This one owner home definitely shows pride of ownership! The attention to detail is obvious! Some of the upg...

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...

Perfectly situated along a picturesque brick lined street with sidewalks in the heart of Winter Park, this beautifully refined residence offers timeless elegance, excepti...

Seller is offering a generous $25,000 credit toward price or closing costs, giving the next owner an incredible opportunity to personalize this Winter Park residence to t...

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

Pre-Construction. To be built. Discover refined modern living in The Enclave, an exclusive boutique community in the heart of Winter Park featuring just 23 custom residen...

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