Maitland, FL Homes for Sale with Private Pool

This beautiful home on a corner lot in Maitland features a new pool and a large backyard. Inside and out, it’s the perfect home to entertain friends and family. The home’s split floor plan and design maximize functionality. The living room, dining room and kitchen are all large spaces, and so are the three bedrooms. An extra room serves as a perfect office or nursery space. The primary suite

Beverly Dodds KELLER WILLIAMS REALTY AT THE PARKS

Fully renovated Dommerich home in Maitland on a wrapping corner lot has been completely redesigned with entertaining at the forefront. A spacious reshape of the kitchen and living spaces create a large gathering space for ease and function with windows out to backyard yard retreat. This custom kitchen features 42-inch white shaker cabinetry with quartzite counters, enjoy a generous center island

Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

Elegant pool home in iconic & coveted Bretton Woods. Discover classic charm & modern comfort in this stunning brick ranch, nestled on an expansive lot. New roof, Trane HVAC, ducts & windows ensure peace of mind & energy efficiency. A sun-dappled front yard & welcoming porch lead to a beautifully updated interior w/ engineered hardwood flooring, a gourmet kitchen w/ top-of-the-line stainless steel

Robert McGinty Legacy Real Estate Partners

Welcome to a truly special and unique home located in the exclusive Hidden Estates subdivision in Maitland. This expansive, single-story custom home offers over 4,000 square feet of beautifully designed living space, featuring four spacious bedrooms and four full bathrooms, plus a separate office, all set on an oversized three-quarter-acre lot on a cul-de-sac.The open-concept floor plan is

Paola Padovan PADOVAN REALTY CORP.

Renovated Maitland Gem with newer pool, move-In ready! Tucked away in a peaceful Maitland neighborhood, this beautifully updated one-story home offers a blend of style, comfort and convenience. With three bedrooms, two baths and 1,760 square feet of thoughtfully designed living space, this property is a hidden gem. Enjoy unbeatable curb appeal with lush landscaping, newer windows/doors, a lighted

Mick Night PREMIER SOTHEBY'S INTL. REALTY

Welcome home to a walkable lifestyle in Maitland! This second-owner well-appointed and updated home is a short 7 minute walk to Publix, trendy new Maitland Social with Foxtail, Bruno’s Pizzaria, and Wave Sushi. The home is situated on a quiet cul de sac of only 7 homes, and faces Lake Maitland and the Nina Canal. 2 minute stroll to Minnehaha Park and Maitland’s pickleball courts. The 5

Daniel Goodman CHARLES RUTENBERG REALTY ORLANDO

A rare opportunity to own a private compound spanning nearly half an acre across an oversized double lot in one of Maitland’s most coveted locations. Masterfully reimagined with unparalleled craftsmanship, this estate is a private sanctuary designed for the discerning buyer—complete with a private tennis and pickleball court, an Olympic-style lap pool, and seamless indoor-outdoor living.

Ahmad Hassan COMPASS FLORIDA LLC

For those with a vision! This rare opportunity in Maitland’s highly sought-after Oakleigh neighborhood offers the perfect canvas for renovation and redesign. Nestled among lakefront estate homes on an oversized lot, this sprawling traditional ranch spans nearly 4,200 square feet on over one-third of an acre, providing ample space to make this home your own. Natural light floods the expansive

Sara Cambron PREMIER SOTHEBY'S INTL. REALTY

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer ~ Welcome to this exceptional –FULLY UPGRADED / POOL HOME– in the highly sought-after Dommerich Estates, where timeless style meets modern design on a spacious .31 ACRE CONSERVATION LOT with serene WOODED VIEWS! Major updates set this home apart; enjoy year round outdoor living with a large

Jennifer Wemert WEMERT GROUP REALTY LLC

Welcome to your dream home in the heart of Maitland’s beloved English Estates neighborhood! This beautifully updated 4-bedroom, 2.5-bathroom home with a dedicated office offers the perfect blend of timeless mid-century design and thoughtful contemporary upgrades. With approximately 2,352 square feet of living space on a generous 16,660 square foot double lot, there’s room to relax, entertain, and

Kara Lushear COLDWELL BANKER REALTY

**NO HOA** **POOL HOME** Welcome to your dream home in one of Central Florida's most sought-after locations! This exquisite property features 3 bedrooms and 3.5 bathrooms, each meticulously designed to provide a serene living experience. The home boasts an open floorplan with 1,966 square feet of light and bright living space, highlighted by beautiful 24x24 porcelain tile that is a show

Sonia Dublis COLDWELL BANKER REALTY

Stylishly Renovated 4-Bedroom Home in Prime Maitland Location This beautifully updated 4-bedroom, 2-bathroom home combines modern convenience with timeless charm. Major upgrades include: kitchen, bathrooms, and flooring (2025), electrical system (2024), permitted roof replacement (2020), and full home re-pipe with CPVC (2014). Designed for both comfort and entertaining, the open-concept layout

Jonathan Minerick HOMECOIN.COM

This 4-bedroom, 3-bathroom home is packed with smart updates and sits in a prime Maitland location, close to shopping, dining, and quick access to the interstate for an easy commute to Orlando and beyond.Inside, you'll love the vaulted ceilings, new luxury vinyl flooring, and a clean, modern aesthetic throughout. The home has been freshly painted and features all-new lighting and fixtures, a

Kelly Althof CENTRAL FLORIDA REALTY EXPERTS

One or more photo(s) has been virtually staged. Don’t miss this beautifully updated 3-bedroom, 2-bathroom English Estates pool home with a versatile bonus room that can serve as a 4th bedroom, office, gym, or playroom—complete with its own private entrance. Priced below appraised value, this home is packed with thoughtful upgrades and modern conveniences. The exterior boasts fresh paint, updated

Nancy Bagby FANNIE HILLMAN & ASSOCIATES

Welcome to 1529 Glastonberry Rd., a beautiful 4 bedroom, 2 bath pool home in an established neighborhood in Maitland. The home is bright and airy with fantastic luxury vinyl flooring, new interior paint and modern lighting. The open concept is perfect for entertaining with a spacious kitchen, updated appliances and granite countertops. The views of the sparkling pool will encourage all to step

Tamara Rorman RE/MAX TOWN CENTRE

This unique, custom-built concrete block home is nestled on a quiet cul-de-sac in the highly sought-after Forest Brook neighborhood. Lovingly maintained, this spacious residence features a grand foyer, formal living and dining rooms, and a bright, airy family room with a cozy fireplace. The open kitchen boasts a gas oven, abundant cabinetry, and a charming eat-in area with built-in desk and

Cheryl Geluso RE/MAX ASSURED

One or more photo(s) has been virtually staged. Welcome to a private oasis in the heart of Maitland. tucked away on a quiet cul-de-sac in an exclusive gated community of just 19 custom homes. This one-owner estate offers a blend of elegance, space and serenity between picturesque Lake Sybelia and Lake Catherine. This five-bedroom, four-and-a-half-bath pool home with a three-car garage sits on an

Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

Welcome to your private retreat in the heart of Maitland! Nestled on a quiet street and backing up to a serene conservation area, this beautifully maintained 4-bedroom, 2-bathroom pool home offers the perfect blend of comfort, privacy, and Florida charm. Step inside to a spacious, light-filled layout featuring an open-concept living and dining area with views that draw you straight to the

Devin Loh COLDWELL BANKER RESIDENTIAL RE

Welcome to Maison du Lac – a breathtaking lakefront estate that epitomizes unrivaled luxury, timeless elegance, and an extraordinary lifestyle. Situated on an expansive 2.7-acre lot along the prestigious Winter Park Chain of Lakes, this extraordinary residence showcases over 120 feet of pristine lakefront with sweeping panoramic views of the longest stretch of Lake Maitland.Blending classic

Maggie Walas FORTUNE INTERNATIONAL REALTY

Tucked away at the end of a quiet cul-de-sac, this serene lakefront retreat is sited on a lush 1.21-acre lot w/ 187 feet of shoreline on tranquil Lake Nina—part of the Winter Park Chain of Lakes—this 4-bedroom, 4.5-bathroom, 4,997-square-foot estate blends Santa Barbara-style charm w/ modern sophistication in one of Central Florida’s most desirable settings. A meandering drive leads you to a

Padgett McCormick KELLY PRICE & COMPANY LLC

Welcome to this beautifully remodeled 4-BEDROOM, 3-BATH HOME, offering an expansive OPEN FLOOR PLAN and a host of luxurious features throughout. The spacious LIVING AND DINING ROOM COMBINATION is filled with NATURAL LIGHT, creating a warm and inviting atmosphere. The home boasts stunning LUXURY VINYL FLOORING and a sleek, updated interior with premium touches, including luxurious TEXTURED GRANITE

Jason Zinno RE/MAX ASSURED

Experience the blend of timeless elegance and modern luxury in this Maitland estate a block away from Lake Sybelia. Completely renovated in 2007, every detail of this home exudes sophistication. A spacious paver driveway leads to a two-car garage, framed by lush tropical landscaping, decorative stone accents, and a charming fountain, creating an inviting first impression. The grand foyer welcomes

Peter Luu REAL BROKER, LLC

Charming, Charlie Clayton built, three-bedroom, two-bath pool home with lake access in Dommerich Estates! Nestled on a corner lot, this home features stunning wood floors throughout, a beautifully renovated kitchen with stainless steel appliances, quartz countertops, solid wood cabinetry, and a spacious dining room with large windows overlooking the backyard. The bright and airy living room

Gwyn Clark FANNIE HILLMAN & ASSOCIATES

Looking for the luxurious lifestyle . . . with an air of quiet serenity? Situated on a .41-acre lot, this very unique custom-built 2-story, 5 bedroom, 4.5 bath pool home is built for the kind of lifestyle you desire. Reminiscent of Spanish/Mediterranean architectural style, this home offers a very practical and livable floor plan. 2 BEDROOMS W/ ENSUITE BATHS: –THE PRIMARY ONE IS DOWNSTAIRS,

Sandi Peery RE/MAX TOWN & COUNTRY REALTY

An Iconic English Estates Gem – 3 Beds, 2 Baths, with a private backyard OASIS. Prepare to be captivated by this beautifully FULLY RENOVATED home in the cherished English Estates Neighborhood. With a fully fenced in backyard and 1,798 square feet of meticulously designed living space, this home is an absolute showstopper. Every corner of this home has been thoughtfully restored with the finest

Shannon Chamoun KELLER WILLIAMS TAMPA CENTRAL

Exceptional Value ** New Reduced price $514,900 ** Great Style, great space, prime location. Remarkable 4-Bedroom, 3-Bathroom Two-Story Home in Maitland, Priced to Sell ! beautiful updated home combines comfort, modern designs and spacious living areas. Enjoy peace of mind with a newer roof, fresh interior

Zep Bholai-Lawrence FUSILIER REALTY GROUP

A Lakefront Masterpiece, this 3-bedroom, 2-bathroom pool home is a gem for those who demand the finest in life. Nestled in the heart of Maitland - From the moment you arrive, the all-new paver driveway and front porch make a striking first impression, setting the stage for the pristine interiors that await. Step inside to nearly 1,700 sq ft of tastefully refined living space, fully updated to

Ahmad Hassan COMPASS FLORIDA LLC

Welcome to 2148 Chippewa Trail, a charming mid-century modern gem adorned with a newer roof, nestled in the heart of Maitland’slovely Dommerich Hills neighborhood. This beautifully updated 3-bedroom, 2-bathroom home offers 1,665 square feet of living spacewith a huge, screened patio and pool area, perfectly blending modern amenities with timeless appeal. Step inside to discover aflowing,

Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

Welcome to 1521 Oxford Rd - here's your opportunity to own a move in ready corner lot property in the English Estates community of Maitland. Situated on .28 Acres. Over 1900 Sqft of living space with 4 bedrooms and 2 baths the floorplan entails an entry foyer tracing to the formal living room, formal dining room, and into the family room adjacent to the kitchen. Enjoy ample cabinetry at the

Ahmad Hassan COMPASS FLORIDA LLC

One or more photo(s) has been virtually staged. Welcome to this stunning 5-bedroom, 2.5-bathroom mid-century gem! Boasting 2,289 sq ft of living space, this home offers a unique blend of modern updates and timeless charm. The open floor plan features a cozy living room with a fireplace that separates the bonus room, providing a versatile space for a formal dining area, playroom, study, or

Kelly De Rivero FLORIDA HOMES REALTY & MTG

One or more photo(s) has been virtually staged. Welcome to this beautifully updated home. The living room welcomes you with a cozy fireplace and a neutral color paint scheme that creates a spacious feel. The kitchen is a chef's dream, featuring all stainless steel appliances. New flooring throughout the home adds to the fresh look, complementing the updated interior and exterior paint. Enjoy

GREGORY BLACKALL OPENDOOR BROKERAGE LLC

Welcome to 705 North Lake Sybelia Drive—an extraordinary custom lakefront residence completed in December 2024 by Konkol Custom Homes. Elevated on a 0.56-acre corner lot w/ approximately 112’ of private lake frontage, this nearly new home blends architectural integrity, smart technology & transitional style. Featuring a crisp white stucco exterior, black-framed impact windows & a remote-operated

Padgett McCormick KELLY PRICE & COMPANY LLC

Just Completed!! SPECIAL BUILDER INCENTIVES AVAILABLE! New Construction with Winter Park Chain of Lakes Access!! You'll be stunned by this gorgeous coastal style home on a private canal that leads to Lake Maitland. This magnificent residence features 5 bedrooms, a bonus room, pool with a relaxing spa and brand new covered boat dock. Your journey begins in the grand two-story foyer featuring

Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake AccessThis meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace.The sleek, chef-inspired kitchen

Kimberly Slinger KELLY PRICE & COMPANY LLC

**Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the pinnacle of

Christopher Soucy REALTY ONE GROUP MVP