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Rolling Hills Drive is the kind of street where homes feel settled into their surroundings, quiet and residential, with attractive homes lining the neighborhood and nature close at hand. Just moments from hiking trails, Lake Mohegan, and Smith Richardson Golf Course, it's a setting that offers both neighborhood connection and easy access to the outdoors. At 126, a classic Colonial sits gracefully on two private acres. The property evolves beautifully through the seasons: green lawns in summer, vibrant foliage in fall, and peaceful snow-covered grounds in winter, each bringing its own character to the setting. Inside, the home carries the same warmth and ease, with cozy, welcoming living spaces anchored by a bright, updated kitchen that naturally becomes the heart of the home. Four full baths add a level of comfort and convenience that makes daily life and hosting feel effortless. Outside, a bluestone front porch with river rock accents offers an inviting place to begin the day, while the backyard opens to broad lawn and a firepit gathering area tucked into the landscape. It's the kind of property where afternoons stretch into evenings, and where outdoor living becomes part of daily life. Inside and out, the home reflects the enduring appeal of a traditional Colonial: balanced, welcoming, and easy to live in. A property defined by space, natural surroundings, and the neighborhood character that makes Rolling Hills Drive one of Fairfield's most peaceful residential settings.

4 Beds ⋅ 4 Baths ⋅ 24158186 MLS

Rolling Hills Drive is the kind of street where homes feel settled into their surroundings, quiet and residential, with attractive homes lining the neighborhood and nature close at hand. Just moments from hiking trails, Lake Mohegan, and Smith Richardson Golf Course, it's a setting that offers both neighborhood connection and easy access to the outdoors. At 126, a classic Colonial sits gracefully on two private acres. The property evolves beautifully through the seasons: green lawns in summer, vibrant foliage in fall, and peaceful snow-covered grounds in winter, each bringing its own character to the setting. Inside, the home carries the same warmth and ease, with cozy, welcoming living spaces anchored by a bright, updated kitchen that naturally becomes the heart of the home. Four full baths add a level of comfort and convenience that makes daily life and hosting feel effortless. Outside, a bluestone front porch with river rock accents offers an inviting place to begin the day, while the backyard opens to broad lawn and a firepit gathering area tucked into the landscape. It's the kind of property where afternoons stretch into evenings, and where outdoor living becomes part of daily life. Inside and out, the home reflects the enduring appeal of a traditional Colonial: balanced, welcoming, and easy to live in. A property defined by space, natural surroundings, and the neighborhood character that makes Rolling Hills Drive one of Fairfield's most peaceful residential settings.

126 Rolling Hills Dr, Fairfield

$1,310,000

Located at 281 Wood House Rd in Fairfield, CT, this beautifully updated home seamlessly blends modern comfort with timeless charm. Offering four spacious bedrooms, including a primary en-suite with a walk-in closet, it provides plenty of flexibility for family, guests, or a home office. The bright and inviting living spaces include a sunlit living room and a cozy family room conveniently situated off the kitchen. The kitchen is a chef's delight, featuring new hardwood floors, a tasteful new backsplash, updated island countertops, and brand-new appliances-refrigerator, dishwasher, washer, and dryer. Hosting is effortless with a generously sized dining room adjacent to the kitchen. The finished basement offers incredible versatility-ideal as a home office, gym, playroom, or extra storage. Step outside to a large, newly fenced backyard, perfect for barbecues, playtime, or relaxing evenings. A two-car garage completes this exceptional property. Situated in a highly desirable Fairfield neighborhood on a quiet dead-end road, this home delivers the perfect blend of style, comfort, and functionality-ready to meet your every need!

4 Beds ⋅ 3 Baths ⋅ 24150329 MLS

Located at 281 Wood House Rd in Fairfield, CT, this beautifully updated home seamlessly blends modern comfort with timeless charm. Offering four spacious bedrooms, including a primary en-suite with a walk-in closet, it provides plenty of flexibility for family, guests, or a home office. The bright and inviting living spaces include a sunlit living room and a cozy family room conveniently situated off the kitchen. The kitchen is a chef's delight, featuring new hardwood floors, a tasteful new backsplash, updated island countertops, and brand-new appliances-refrigerator, dishwasher, washer, and dryer. Hosting is effortless with a generously sized dining room adjacent to the kitchen. The finished basement offers incredible versatility-ideal as a home office, gym, playroom, or extra storage. Step outside to a large, newly fenced backyard, perfect for barbecues, playtime, or relaxing evenings. A two-car garage completes this exceptional property. Situated in a highly desirable Fairfield neighborhood on a quiet dead-end road, this home delivers the perfect blend of style, comfort, and functionality-ready to meet your every need!

281 Wood House Rd, Fairfield

$1,305,000

Welcome to 947 Galloping Hill Road. This true mid-century modern home was designed by the important architect Victor Civkin in 1967. This well thought out ranch has 4 bedrooms and 3 1/2 baths and is perfectly situated on a flat, private acre. Step inside the large foyer that has curved walls and a skylight. The living room is spacious with a rounded wall of floor to ceiling windows which flood the space with light. This room overlooks the professionally landscaped yard. The kitchen has white cabinets, stainless steel appliances, Subzero, granite counters, wood floor and a slider to the deck. The dining room has beautiful built-ins and a wood floor. There is also a curved wall of windows. The primary bedroom has a wall of closets, a full bath and has many windows. The other 3 bedrooms are spacious, with one having its own ensuite. The family room has a large statement-making wood burning stone fireplace and a vaulted ceiling with beams. There is a slider that connects to the screened-in porch which wraps around the house. This porch is a perfect place to entertain or enjoy quiet relaxation. The lower level is partially finished with a playroom. This home has a full house generator. The property is located in a desirable area of Fairfield. It is convenient to highways, shopping , 2 Universities, 5 beaches and Metro-North. It is a very special property and balances family functionality with modern elements! Enjoy all that Fairfield has to offer!

4 Beds ⋅ 4 Baths ⋅ 24133099 MLS

Welcome to 947 Galloping Hill Road. This true mid-century modern home was designed by the important architect Victor Civkin in 1967. This well thought out ranch has 4 bedrooms and 3 1/2 baths and is perfectly situated on a flat, private acre. Step inside the large foyer that has curved walls and a skylight. The living room is spacious with a rounded wall of floor to ceiling windows which flood the space with light. This room overlooks the professionally landscaped yard. The kitchen has white cabinets, stainless steel appliances, Subzero, granite counters, wood floor and a slider to the deck. The dining room has beautiful built-ins and a wood floor. There is also a curved wall of windows. The primary bedroom has a wall of closets, a full bath and has many windows. The other 3 bedrooms are spacious, with one having its own ensuite. The family room has a large statement-making wood burning stone fireplace and a vaulted ceiling with beams. There is a slider that connects to the screened-in porch which wraps around the house. This porch is a perfect place to entertain or enjoy quiet relaxation. The lower level is partially finished with a playroom. This home has a full house generator. The property is located in a desirable area of Fairfield. It is convenient to highways, shopping , 2 Universities, 5 beaches and Metro-North. It is a very special property and balances family functionality with modern elements! Enjoy all that Fairfield has to offer!

947 Galloping Hill Rd, Fairfield

$1,300,000

Location, location, location! Welcome to this delightful contemporary located at the end of a quiet cul-de-sac in lovely Greenfield Hill. With 4 bedrooms, 2.5 baths and a floor plan offering numerous possibilities for today's living and work lifestyles, this home checks so many boxes. A gracious Living Rm with vaulted ceiling brings the outside in with a wall of windows along the back. Enjoy a lovely view of the trees and backyard as soon as you step in the entry. A formal Dining Rm with built-in buffet and a nice Screened Porch with bluestone floor, also open to the back. The large bright Kitchen has granite countertops, separate island with cooktop, an eat-in Breakfast area, walk-in pantry and new GE Cafe appliances added in the Fall of 2021. Upper level has a Primary Bedroom with a spacious walk-in closet. Prepared to be wowed with the fully updated en-suite bath with soaking tub and separate shower. Two additional bedrooms with a full Bath along with large hallway closets for storage complete the floor. Lower level has a Family Room with wood-burning fireplace and built-in bookshelves. Off this room is the 4th Bedroom, with an Office in back. The finished Basement below offers even more space for play and relaxation. Lovingly cared for by the same family for 25 years, other notable features include a full house generator plumbed to the gas line and a new furnace in October 2020. Ask agent for additional features - you don't want to miss seeing this one!

4 Beds ⋅ 3 Baths ⋅ 24168777 MLS

Location, location, location! Welcome to this delightful contemporary located at the end of a quiet cul-de-sac in lovely Greenfield Hill. With 4 bedrooms, 2.5 baths and a floor plan offering numerous possibilities for today's living and work lifestyles, this home checks so many boxes. A gracious Living Rm with vaulted ceiling brings the outside in with a wall of windows along the back. Enjoy a lovely view of the trees and backyard as soon as you step in the entry. A formal Dining Rm with built-in buffet and a nice Screened Porch with bluestone floor, also open to the back. The large bright Kitchen has granite countertops, separate island with cooktop, an eat-in Breakfast area, walk-in pantry and new GE Cafe appliances added in the Fall of 2021. Upper level has a Primary Bedroom with a spacious walk-in closet. Prepared to be wowed with the fully updated en-suite bath with soaking tub and separate shower. Two additional bedrooms with a full Bath along with large hallway closets for storage complete the floor. Lower level has a Family Room with wood-burning fireplace and built-in bookshelves. Off this room is the 4th Bedroom, with an Office in back. The finished Basement below offers even more space for play and relaxation. Lovingly cared for by the same family for 25 years, other notable features include a full house generator plumbed to the gas line and a new furnace in October 2020. Ask agent for additional features - you don't want to miss seeing this one!

112 Calico Ln, Fairfield

$1,300,000

Nestled in the heart of coveted Greenfield Hill, this beautiful classic New England Colonial blends timeless charm, modern comfort & exceptional privacy. Set on 3.5 picturesque acres, the property feels like a private retreat yet is just minutes from town, beaches & Fairfield's top-rated schools. Designed for everyday living & entertaining, the home offers over 4,000 sq ft of thoughtfully designed space with sun-filled rooms & hardwood floors. The heart of the home is a spacious eat-in kitchen with stainless steel appliances plus a built-in bar area flowing into the inviting living room with a fireplace & large windows overlooking the serene property, perfect for gathering with family & friends. A dramatic family room with vaulted ceilings, fireplace & sliding doors leads to a large deck for seamless indoor-outdoor living surrounded by nature. The light-filled primary suite is a true sanctuary with a walk-in closet, fireplace, a luxurious spa-like bath with Carrara marble, heated floors & a soaking tub. The finished 3rd floor offers a 4th bedroom & full bath/versatile bonus space (au pair suite, office, playroom). A walk-out lower level has flexible space for a playroom, office or gym, plus a nearby stone patio. Expansive grounds feature open lawn, gardens, full deer fencing, mature trees, a tranquil brook-perfect for relaxing or entertaining in a peaceful natural setting. This timeless, elegant Greenfield Hill home with exceptional space & privacy is a rare opportunity.

4 Beds ⋅ 4 Baths ⋅ 24161267 MLS

Nestled in the heart of coveted Greenfield Hill, this beautiful classic New England Colonial blends timeless charm, modern comfort & exceptional privacy. Set on 3.5 picturesque acres, the property feels like a private retreat yet is just minutes from town, beaches & Fairfield's top-rated schools. Designed for everyday living & entertaining, the home offers over 4,000 sq ft of thoughtfully designed space with sun-filled rooms & hardwood floors. The heart of the home is a spacious eat-in kitchen with stainless steel appliances plus a built-in bar area flowing into the inviting living room with a fireplace & large windows overlooking the serene property, perfect for gathering with family & friends. A dramatic family room with vaulted ceilings, fireplace & sliding doors leads to a large deck for seamless indoor-outdoor living surrounded by nature. The light-filled primary suite is a true sanctuary with a walk-in closet, fireplace, a luxurious spa-like bath with Carrara marble, heated floors & a soaking tub. The finished 3rd floor offers a 4th bedroom & full bath/versatile bonus space (au pair suite, office, playroom). A walk-out lower level has flexible space for a playroom, office or gym, plus a nearby stone patio. Expansive grounds feature open lawn, gardens, full deer fencing, mature trees, a tranquil brook-perfect for relaxing or entertaining in a peaceful natural setting. This timeless, elegant Greenfield Hill home with exceptional space & privacy is a rare opportunity.

3725 Redding Rd, Fairfield

$1,255,000

Welcome to 109 Buckboard Lane, a Magazine worthy renovated high ranch at the end of a serene Fairfield, CT. cul de sac in Greenfield Hill. Tucked at the back of a private back lot, this completely reimagined raised ranch isn't just renovated, it's transformed. Step inside and prepare to fall in love with a kitchen that redefines luxury at this price point. Drop dead gorgeous cabinet design and Thermador everything. The highest quality appliances, the oversized built-in refrigerator, wall oven, dual refrigerator drawers, and the most luxurious feature? The cooktop elements are built into the stone island countertop. The induction heating system is triggered when you place your pan on the stone! This isn't just where you cook, it's where you live. The magic continues outdoors on your expansive two-story entertainment area, an entertainer's dream with dedicated seating and TV area set below the deck so rain or shine, the covered lower level lounge keeps the party going while you relax in style. Downstairs, discover a warm family room anchored by the fireplace. Showcase built-ins perfect for displaying your treasures and a large private in-law suite with full bath and it's own private entrance. Ideal for an au pair, son or daughter home from college or an aging parent. There is also an attached 2-car garage. 109 Buckboard isn't just a home, it's where you belong.

4 Beds ⋅ 4 Baths ⋅ 24133849 MLS

Welcome to 109 Buckboard Lane, a Magazine worthy renovated high ranch at the end of a serene Fairfield, CT. cul de sac in Greenfield Hill. Tucked at the back of a private back lot, this completely reimagined raised ranch isn't just renovated, it's transformed. Step inside and prepare to fall in love with a kitchen that redefines luxury at this price point. Drop dead gorgeous cabinet design and Thermador everything. The highest quality appliances, the oversized built-in refrigerator, wall oven, dual refrigerator drawers, and the most luxurious feature? The cooktop elements are built into the stone island countertop. The induction heating system is triggered when you place your pan on the stone! This isn't just where you cook, it's where you live. The magic continues outdoors on your expansive two-story entertainment area, an entertainer's dream with dedicated seating and TV area set below the deck so rain or shine, the covered lower level lounge keeps the party going while you relax in style. Downstairs, discover a warm family room anchored by the fireplace. Showcase built-ins perfect for displaying your treasures and a large private in-law suite with full bath and it's own private entrance. Ideal for an au pair, son or daughter home from college or an aging parent. There is also an attached 2-car garage. 109 Buckboard isn't just a home, it's where you belong.

109 Buckboard Ln, Fairfield

$1,250,000

BASED ON STRONG INTEREST, PLEASE SUBMIT ALL OFFERS, HIGHEST & BEST, BY 5PM MONDAY MAY 18. Sitting pretty behind a charming fieldstone wall, in a sought after neighborhood, this long loved Garrison Colonial feels fresh and inviting! Recent updates include a brand new high efficiency boiler and hot water heater, new roof, new gravel driveway with Belgian Block, new Pella windows, new Bathrooms detailed with Turkish tile, interior paint in soft hues of grey, and gleaming hardwood floors throughout. The classic center hall leads to a sunny Living Room, and alternately to the Family Room, anchored by a cozy fireplace with raised hearth. The Eat in Kitchen opens to the Dining Room. The Den/Office, Laundry and Powder Room complete the main level. Upstairs, four generously scaled Bedrooms include a Primary en suite Bedroom and three other Bedrooms which share a hall Bathroom. Walk up Attic offers additional storage. Outside, the expansive deck and bluestone patio overlook an exceptionally private and flat 1.1 acre of lush lawn, specimen trees, and a distant shed that looks like a small vintage barn. Sited at the highest point of Galloping Hill, this rare panoramic vista elicits a feeling of pure serenity. Convenient to Fairfield's town center, with restaurants, shopping, library, train and beaches, this special slice of Greenfield Hill is a wonderful place to call home!

4 Beds ⋅ 3 Baths ⋅ 24173423 MLS

BASED ON STRONG INTEREST, PLEASE SUBMIT ALL OFFERS, HIGHEST & BEST, BY 5PM MONDAY MAY 18. Sitting pretty behind a charming fieldstone wall, in a sought after neighborhood, this long loved Garrison Colonial feels fresh and inviting! Recent updates include a brand new high efficiency boiler and hot water heater, new roof, new gravel driveway with Belgian Block, new Pella windows, new Bathrooms detailed with Turkish tile, interior paint in soft hues of grey, and gleaming hardwood floors throughout. The classic center hall leads to a sunny Living Room, and alternately to the Family Room, anchored by a cozy fireplace with raised hearth. The Eat in Kitchen opens to the Dining Room. The Den/Office, Laundry and Powder Room complete the main level. Upstairs, four generously scaled Bedrooms include a Primary en suite Bedroom and three other Bedrooms which share a hall Bathroom. Walk up Attic offers additional storage. Outside, the expansive deck and bluestone patio overlook an exceptionally private and flat 1.1 acre of lush lawn, specimen trees, and a distant shed that looks like a small vintage barn. Sited at the highest point of Galloping Hill, this rare panoramic vista elicits a feeling of pure serenity. Convenient to Fairfield's town center, with restaurants, shopping, library, train and beaches, this special slice of Greenfield Hill is a wonderful place to call home!

1090 Galloping Hill Rd, Fairfield

$1,180,000

Rare lower Greenfield Hill opportunity at an accessible price point. Set on 2 private acres, 209 Merwins Lane offers charm, privacy and everyday livability in one of Fairfield's most sought after locations. Enjoy easy access to Greenfield Center, a quick drive to Westport and a convenient direct route to Fairfield Train Station, just 3.5 miles away. This classic center hall Cape is warm, inviting and easy to love. The main level features a living room with fireplace, traditional dining room, functional kitchen, an oversized rear family room that creates wonderful additional living space and a full bath. In addition, there is a flexible first floor room, currently used as additional living space and a home office, adds convenience for today's lifestyle while offering options for guests, work from home or future needs. Upstairs, two generously sized bedrooms share a full bath off the center hall. One bedroom was previously two bedroom rooms, offering added flexibility within the existing footprint if desired to convert back to three bedrooms. Perfect for downsizers, first time Greenfield Hill buyers or anyone seeking privacy, land and location, this home offers immediate appeal with meaningful long term potential. Move right in, enjoy the charm and explore future possibilities at your own pace in a beloved Fairfield neighborhood.

3 Beds ⋅ 2 Baths ⋅ 24154961 MLS

Rare lower Greenfield Hill opportunity at an accessible price point. Set on 2 private acres, 209 Merwins Lane offers charm, privacy and everyday livability in one of Fairfield's most sought after locations. Enjoy easy access to Greenfield Center, a quick drive to Westport and a convenient direct route to Fairfield Train Station, just 3.5 miles away. This classic center hall Cape is warm, inviting and easy to love. The main level features a living room with fireplace, traditional dining room, functional kitchen, an oversized rear family room that creates wonderful additional living space and a full bath. In addition, there is a flexible first floor room, currently used as additional living space and a home office, adds convenience for today's lifestyle while offering options for guests, work from home or future needs. Upstairs, two generously sized bedrooms share a full bath off the center hall. One bedroom was previously two bedroom rooms, offering added flexibility within the existing footprint if desired to convert back to three bedrooms. Perfect for downsizers, first time Greenfield Hill buyers or anyone seeking privacy, land and location, this home offers immediate appeal with meaningful long term potential. Move right in, enjoy the charm and explore future possibilities at your own pace in a beloved Fairfield neighborhood.

209 Merwins Ln, Fairfield

$1,175,000

Nestled in Fairfield's coveted Greenfield Hill neighborhood, this beautifully updated 4-bedroom Colonial blends timeless character with modern functionality. The main level offers an open-concept layout anchored by a standout chef's kitchen with custom cabinetry and a striking quartz waterfall island, flowing seamlessly into the dining area and family room, while a separate living room with a cozy wood-burning fireplace provides a warm retreat for relaxing or intimate gatherings. Upstairs, you'll find four generously sized bedrooms, including a primary suite with a walk-in closet and private full bath. The remodeled 450 sq. ft. lower level delivers versatile space for a home office, media room, gym, or playroom. Extensive 2022 updates include a new HVAC system, upgraded electrical, recessed lighting, refinished hardwood floors, new garage and interior doors, fresh trim and baseboards, and fresh paint throughout. Outside, enjoy a private deck and a tranquil backyard framed by mature trees and classic New England stone walls-perfect for entertaining or unwinding-plus the added benefit of coastal charm and a welcoming community. Privacy in the woods, yet minutes drive to Blackrock Tpke, Lake Mohegan, and Smith Richards Golf Course.

4 Beds ⋅ 3 Baths ⋅ 24156324 MLS

Nestled in Fairfield's coveted Greenfield Hill neighborhood, this beautifully updated 4-bedroom Colonial blends timeless character with modern functionality. The main level offers an open-concept layout anchored by a standout chef's kitchen with custom cabinetry and a striking quartz waterfall island, flowing seamlessly into the dining area and family room, while a separate living room with a cozy wood-burning fireplace provides a warm retreat for relaxing or intimate gatherings. Upstairs, you'll find four generously sized bedrooms, including a primary suite with a walk-in closet and private full bath. The remodeled 450 sq. ft. lower level delivers versatile space for a home office, media room, gym, or playroom. Extensive 2022 updates include a new HVAC system, upgraded electrical, recessed lighting, refinished hardwood floors, new garage and interior doors, fresh trim and baseboards, and fresh paint throughout. Outside, enjoy a private deck and a tranquil backyard framed by mature trees and classic New England stone walls-perfect for entertaining or unwinding-plus the added benefit of coastal charm and a welcoming community. Privacy in the woods, yet minutes drive to Blackrock Tpke, Lake Mohegan, and Smith Richards Golf Course.

6 Buckboard Ln, Fairfield

$1,170,000

Sprawling ten room ranch style residence offering 3 acres on a prime estate street in Greenfield Hill. This stately home is discreetly positioned behind a brick wall and approached by a sweeping circular drive creating a grand sense of arrival. Inside this impressive home discover a striking Indoor Pool housed in its own sun lit pavilion. This dramatic recreation space adjoins the Kitchen and Play Rooms- ideal for effortless entertaining with seamless flow to the Pool, private Patio and an expansive brick Terrace overlooking the grounds and Tennis Court. Set a table in the formal Dining Room with built-ins and gather in the Living Room with fireplace, an adjacent Office provides for work from home duties. The heart of the home, between the Family and Play Rooms, is a spacious custom Kitchen complete with a large center island, abundant cabinetry and counter space, dining area and access to a covered patio-perfect for al fresco grilling and dining. The Primary Suite continues to impress with a vaulted ceiling, fireplace, Full Bath, walk-in closets and a second "Spa" Bath with whirlpool tub. Three additional Bedrooms and two more full Baths complete the private Bedroom wing. Additional highlights include a side entry Mudroom and Four Car Garage with ample storage for vehicles and recreational equipment. Truly a rare opportunity for one floor country living in a most desirable location just two miles from Greenfield Hill Village's shopping and dining destinations.

4 Beds ⋅ 6 Baths ⋅ 24109949 MLS

Sprawling ten room ranch style residence offering 3 acres on a prime estate street in Greenfield Hill. This stately home is discreetly positioned behind a brick wall and approached by a sweeping circular drive creating a grand sense of arrival. Inside this impressive home discover a striking Indoor Pool housed in its own sun lit pavilion. This dramatic recreation space adjoins the Kitchen and Play Rooms- ideal for effortless entertaining with seamless flow to the Pool, private Patio and an expansive brick Terrace overlooking the grounds and Tennis Court. Set a table in the formal Dining Room with built-ins and gather in the Living Room with fireplace, an adjacent Office provides for work from home duties. The heart of the home, between the Family and Play Rooms, is a spacious custom Kitchen complete with a large center island, abundant cabinetry and counter space, dining area and access to a covered patio-perfect for al fresco grilling and dining. The Primary Suite continues to impress with a vaulted ceiling, fireplace, Full Bath, walk-in closets and a second "Spa" Bath with whirlpool tub. Three additional Bedrooms and two more full Baths complete the private Bedroom wing. Additional highlights include a side entry Mudroom and Four Car Garage with ample storage for vehicles and recreational equipment. Truly a rare opportunity for one floor country living in a most desirable location just two miles from Greenfield Hill Village's shopping and dining destinations.

3853 Congress St, Fairfield

$1,140,000

ENDLESS POTENTIAL in Sought-After Greenfield Hill. Opportunity awaits to restore this once-graceful Colonial to its former grandeur. Set on a beautiful, level 2.41-acre parcel in the highly desirable Greenfield Hill neighborhood, this property offers the chance to create a truly exceptional estate. Steeped in character and nostalgia, the home features generously sized rooms, hardwood floors throughout most of the house, double staircases, and a walkout basement. With more than five bedrooms, an expansive kitchen ready to be reimagined as the heart of the home, a formal dining room designed for memorable gatherings, a spacious living room with a fireplace, and a screened porch that once welcomed quiet afternoons, the possibilities are endless. Bring back to life the tennis court that hasn't been enjoyed in years. This property requires extensive renovation and is being offered as an opportunity for buyers with vision. Whether you're looking to restore its timeless charm or create your dream home from the existing footprint, the setting and scale provide an outstanding foundation. With thoughtful planning and investment, 2514 Redding Road has the potential to become a magnificent Greenfield Hill residence once again. Buyer to do their own due diligence.

5 Beds ⋅ 4 Baths ⋅ 24189981 MLS

ENDLESS POTENTIAL in Sought-After Greenfield Hill. Opportunity awaits to restore this once-graceful Colonial to its former grandeur. Set on a beautiful, level 2.41-acre parcel in the highly desirable Greenfield Hill neighborhood, this property offers the chance to create a truly exceptional estate. Steeped in character and nostalgia, the home features generously sized rooms, hardwood floors throughout most of the house, double staircases, and a walkout basement. With more than five bedrooms, an expansive kitchen ready to be reimagined as the heart of the home, a formal dining room designed for memorable gatherings, a spacious living room with a fireplace, and a screened porch that once welcomed quiet afternoons, the possibilities are endless. Bring back to life the tennis court that hasn't been enjoyed in years. This property requires extensive renovation and is being offered as an opportunity for buyers with vision. Whether you're looking to restore its timeless charm or create your dream home from the existing footprint, the setting and scale provide an outstanding foundation. With thoughtful planning and investment, 2514 Redding Road has the potential to become a magnificent Greenfield Hill residence once again. Buyer to do their own due diligence.

2514 Redding Rd, Fairfield

$1,100,000

Welcome to the charming, historic community of Greenfield Hills! One of Connecticut's most picturesque New England communities that combines a quiet lifestyle, outdoor activities, and warm and friendly neighborhoods. A rare find! This vintage 1885 classic Federal style home features dining room with fireplace, front foyer, large living room, eat-in kitchen, three bedrooms, 1 1/2 baths and incredible addition that includes a 3 car garage and large comfortable apartment! This cozy, apartment has a private entrance with an eat-in-kitchen, living room, 2 bedrooms and full bathroom. This great space can be used as a private in-law apartment, au pair suite, artists studio, or a home office. Additional features include Hardwood floors, built-in cabinetry, and separate heating systems for main house and apartment. The home is in need of remodeling/updating and is to be sold "As Is".

5 Beds ⋅ 3 Baths ⋅ 24142608 MLS

Welcome to the charming, historic community of Greenfield Hills! One of Connecticut's most picturesque New England communities that combines a quiet lifestyle, outdoor activities, and warm and friendly neighborhoods. A rare find! This vintage 1885 classic Federal style home features dining room with fireplace, front foyer, large living room, eat-in kitchen, three bedrooms, 1 1/2 baths and incredible addition that includes a 3 car garage and large comfortable apartment! This cozy, apartment has a private entrance with an eat-in-kitchen, living room, 2 bedrooms and full bathroom. This great space can be used as a private in-law apartment, au pair suite, artists studio, or a home office. Additional features include Hardwood floors, built-in cabinetry, and separate heating systems for main house and apartment. The home is in need of remodeling/updating and is to be sold "As Is".

179 Verna Hill Rd, Fairfield

$1,085,000

Come see this well-maintained 4-bedroom, 2.5-bath ranch set on over 2 acres in Fairfield's Greenfield Hill neighborhood. The spacious corner lot offers a private fenced-in yard along with a meticulously maintained barn. Inside, the home features central air, natural gas heat, a new deck, and multiple fireplaces. The finished lower level adds plenty of additional living space with a second kitchen, bathroom, two additional rooms, and a large entertainment area-perfect for an in-law setup, guests, or extended living. It also offers direct access to the two-car garage. With over two acres, plenty of living space, and so much potential, this is a great opportunity to make this Greenfield Hill property your own.

4 Beds ⋅ 3 Baths ⋅ 24199075 MLS

Come see this well-maintained 4-bedroom, 2.5-bath ranch set on over 2 acres in Fairfield's Greenfield Hill neighborhood. The spacious corner lot offers a private fenced-in yard along with a meticulously maintained barn. Inside, the home features central air, natural gas heat, a new deck, and multiple fireplaces. The finished lower level adds plenty of additional living space with a second kitchen, bathroom, two additional rooms, and a large entertainment area-perfect for an in-law setup, guests, or extended living. It also offers direct access to the two-car garage. With over two acres, plenty of living space, and so much potential, this is a great opportunity to make this Greenfield Hill property your own.

570 Burr St, Fairfield

$1,000,000

A little slice of Vermont in Fairfield! This expanded antique is truly exceptional,offering a private country feel just minutes from all the amenities of Fairfield.Pull into the circular drive with stone wall and you are transported!The family room is a true retreat; you will be captivated by the gleaming wide plank floors,large fireplace with wood stove, beams and slider with gorgeous backyard views.Kitchen and dining room are open beautifully for entertaining with ease.There is a 1st fl full bath and office (or 5th bedrm opt) Upstairs are 3 bedrooms, plus updated hall bath w steam shower.One bedroom has a vaulted ceiling, another has a gas log fire-place,sitting area and WIC.The primary suite has a WIC, a slider to the backyard and updated bath with soaking tub and sep shower.The 4th bedroom is on the 3rd floor with plenty of windows and treehouse like views.The multicar garage is a standout:added in 2016 it is fit for an auto enthusiast, hobbyist, or craftsman.It is heated and cooled, has a roughed in bath, and offers a full second floor with endless possibilities.The 1.79 acre lot is idyllic. It offers a separate shed for equipment, a toolshed with workbenches, electricity and woodstove, and a woodshed. The home is heated by nat gas or opt for the outdoor woodburning boiler system for sustainable, eco-friendly heat! Whole house generator. A very special property and just 2 min to the Merritt and Black Rock Tpk,15 min to Fairfield Center, MetroNorth, shopping and dining

4 Beds ⋅ 3 Baths ⋅ 24136797 MLS

A little slice of Vermont in Fairfield! This expanded antique is truly exceptional,offering a private country feel just minutes from all the amenities of Fairfield.Pull into the circular drive with stone wall and you are transported!The family room is a true retreat; you will be captivated by the gleaming wide plank floors,large fireplace with wood stove, beams and slider with gorgeous backyard views.Kitchen and dining room are open beautifully for entertaining with ease.There is a 1st fl full bath and office (or 5th bedrm opt) Upstairs are 3 bedrooms, plus updated hall bath w steam shower.One bedroom has a vaulted ceiling, another has a gas log fire-place,sitting area and WIC.The primary suite has a WIC, a slider to the backyard and updated bath with soaking tub and sep shower.The 4th bedroom is on the 3rd floor with plenty of windows and treehouse like views.The multicar garage is a standout:added in 2016 it is fit for an auto enthusiast, hobbyist, or craftsman.It is heated and cooled, has a roughed in bath, and offers a full second floor with endless possibilities.The 1.79 acre lot is idyllic. It offers a separate shed for equipment, a toolshed with workbenches, electricity and woodstove, and a woodshed. The home is heated by nat gas or opt for the outdoor woodburning boiler system for sustainable, eco-friendly heat! Whole house generator. A very special property and just 2 min to the Merritt and Black Rock Tpk,15 min to Fairfield Center, MetroNorth, shopping and dining

2492 Congress St, Fairfield

$977,000

RESPECTFULLY; PLEASE SUBMIT HIGHEST AND BEST BY MONDAY 27TH @ 6 PM. Everything Retouched | 2+ Acres | Expansion Opportunity Located in desirable Greenfield Hill, this fully remodeled single-level ranch offers estate-style living with exceptional expansion potential. Set on over 2 level acres-the smallest home on a street of significantly larger residences-this property presents a rare opportunity to build equity and expand. The usable yard features stone walls, classic New England charm, and privacy, with inland wetlands toward the rear. Ample space for outdoor living or a future pool, plus a chicken coop and storage barn/shed for added versatility. Exterior features include a newer roof, gutter guards, new cedar shingles, cable railing, cedar tongue-and-groove deck ceiling, and high-end materials throughout. Take note of the incredible screened-in back deck, composite front porch, new windows, attached 2-car garage, and storage shed. Above-and-beyond mechanicals include propane heat fueled home w/ two, 100 gallon tanks, Trane HVAC central air, Takagi tankless hot water, fully fenced backyard, and Generac generator. Freshly painted interior with hardwood floors, updated kitchen with extensive cabinetry, quartz island, coffee bar, pantry, and abundant storage. Additional highlights include an ensuite primary bedroom, fireplaced living room, ceiling fans, full unfinished basement spanning the home, and smart home Lutron Caseta system. See full list of highlights and features.

3 Beds ⋅ 2 Baths ⋅ 24167637 MLS

RESPECTFULLY; PLEASE SUBMIT HIGHEST AND BEST BY MONDAY 27TH @ 6 PM. Everything Retouched | 2+ Acres | Expansion Opportunity Located in desirable Greenfield Hill, this fully remodeled single-level ranch offers estate-style living with exceptional expansion potential. Set on over 2 level acres-the smallest home on a street of significantly larger residences-this property presents a rare opportunity to build equity and expand. The usable yard features stone walls, classic New England charm, and privacy, with inland wetlands toward the rear. Ample space for outdoor living or a future pool, plus a chicken coop and storage barn/shed for added versatility. Exterior features include a newer roof, gutter guards, new cedar shingles, cable railing, cedar tongue-and-groove deck ceiling, and high-end materials throughout. Take note of the incredible screened-in back deck, composite front porch, new windows, attached 2-car garage, and storage shed. Above-and-beyond mechanicals include propane heat fueled home w/ two, 100 gallon tanks, Trane HVAC central air, Takagi tankless hot water, fully fenced backyard, and Generac generator. Freshly painted interior with hardwood floors, updated kitchen with extensive cabinetry, quartz island, coffee bar, pantry, and abundant storage. Additional highlights include an ensuite primary bedroom, fireplaced living room, ceiling fans, full unfinished basement spanning the home, and smart home Lutron Caseta system. See full list of highlights and features.

208 Wildflower Ln, Fairfield

$950,000

CHESTNUT GROVE - Wonderful opportunity to enhance an extraordinary, sweeping 2.39 acre parcel in a beautiful and bucolic Greenfield Hill location. This expansive property nestled within a Chestnut Grove, features a stately Barn providing Garage storage suitable for farming equipment and motor vehicles, and a recently constructed second story Studio Apartment enjoying a haven of privacy and seclusion. The sun-lit Great Room presents a fully equipped Kitchen with cabinetry and Breakfast Bar, Laundry with stack washer and dryer, and a beautifully tiled full bath with shower. Currently taxed under Farm Status. NEW ASSESSMENT FOR TAX YEAR 2026 - 2027 IS $611,450

1 Baths ⋅ 24166262 MLS

CHESTNUT GROVE - Wonderful opportunity to enhance an extraordinary, sweeping 2.39 acre parcel in a beautiful and bucolic Greenfield Hill location. This expansive property nestled within a Chestnut Grove, features a stately Barn providing Garage storage suitable for farming equipment and motor vehicles, and a recently constructed second story Studio Apartment enjoying a haven of privacy and seclusion. The sun-lit Great Room presents a fully equipped Kitchen with cabinetry and Breakfast Bar, Laundry with stack washer and dryer, and a beautifully tiled full bath with shower. Currently taxed under Farm Status. NEW ASSESSMENT FOR TAX YEAR 2026 - 2027 IS $611,450

3509 Redding Rd, Fairfield

$815,000

Welcome to 200 Joan Drive-a home that's more than just a place to live.It's where you can breathe, recharge, & truly feel at home.From the moment you arrive, the peaceful, tree-lined yard sets the tone:this is where memories are made. Step inside the foyer, & you'll immediately feel the warmth & comfort this home offers.Spacious living room, complete with a cozy fireplace, is perfect for chilly New England nights. The eat-in kitchen features a charming garden window, stainless steel appliances, & plenty of room for family gatherings-all while enjoying beautiful views of the trees that surround the back deck. Start your mornings with coffee in the serenity of your private outdoor setting.For more formal entertaining, the dining room flows seamlessly from the kitchen.The heart of the home, the family room, offers a second fireplace, French doors, & the ideal space to relax-whether you're playing games, enjoying a quiet evening, or cheering on your favorite team.Upstairs, the expansive primary bedroom boasts multiple closets & enough space for a reading nook/sitting area. Three additional bedrooms-each with hw floors beneath the carpeting-provide comfort and flexibility. Update the carpets, or reveal the hw to suit your style. A walk-up attic offers abundant storage.This is more than a house-it's where your next chapter begins. Located in a sought-after neighborhood, close to shopping, restaurants, Merritt Pky & Lake Mohegan. Subject to Probate Court

4 Beds ⋅ 4 Baths ⋅ 24119354 MLS

Welcome to 200 Joan Drive-a home that's more than just a place to live.It's where you can breathe, recharge, & truly feel at home.From the moment you arrive, the peaceful, tree-lined yard sets the tone:this is where memories are made. Step inside the foyer, & you'll immediately feel the warmth & comfort this home offers.Spacious living room, complete with a cozy fireplace, is perfect for chilly New England nights. The eat-in kitchen features a charming garden window, stainless steel appliances, & plenty of room for family gatherings-all while enjoying beautiful views of the trees that surround the back deck. Start your mornings with coffee in the serenity of your private outdoor setting.For more formal entertaining, the dining room flows seamlessly from the kitchen.The heart of the home, the family room, offers a second fireplace, French doors, & the ideal space to relax-whether you're playing games, enjoying a quiet evening, or cheering on your favorite team.Upstairs, the expansive primary bedroom boasts multiple closets & enough space for a reading nook/sitting area. Three additional bedrooms-each with hw floors beneath the carpeting-provide comfort and flexibility. Update the carpets, or reveal the hw to suit your style. A walk-up attic offers abundant storage.This is more than a house-it's where your next chapter begins. Located in a sought-after neighborhood, close to shopping, restaurants, Merritt Pky & Lake Mohegan. Subject to Probate Court

200 Joan Dr, Fairfield

$800,000

Through a pillared entrance sited privately from the road discover a tremendous opportunity to own a one of a kind Fairfield home with style, light & space for everyone inside & out. Reminiscent of a mid-century modern deck house, enhanced by vaulted ceilings in every main level room & newly refinished hardwood floors, you will be captivated by the open plan with abundant light throughout. Living room with architectural beams and stunning floor to ceiling fireplace. Fabulous original kitchen with updated appliances and quality cabinetry will steal your heart. Four ample bedrooms complete the main level including primary with two closets & private bath. The walk out lower level offers a cozy den or office with built in shelves plus half-bath & laundry. An amazing oversized screen porch overlooks the picturesque & peaceful low maintenance property sure to be enjoyed in every season. Walk to Brett Woods & enjoy over 180 acres of walking trails or hop in the car and get to shopping & dining in minutes. Move in and enjoy as is, or create the stylish home of your dreams. City water and gas in the street- please do your own research for connection possibilities. You can be in your new home for the holidays!

4 Beds ⋅ 3 Baths ⋅ 24136043 MLS

Through a pillared entrance sited privately from the road discover a tremendous opportunity to own a one of a kind Fairfield home with style, light & space for everyone inside & out. Reminiscent of a mid-century modern deck house, enhanced by vaulted ceilings in every main level room & newly refinished hardwood floors, you will be captivated by the open plan with abundant light throughout. Living room with architectural beams and stunning floor to ceiling fireplace. Fabulous original kitchen with updated appliances and quality cabinetry will steal your heart. Four ample bedrooms complete the main level including primary with two closets & private bath. The walk out lower level offers a cozy den or office with built in shelves plus half-bath & laundry. An amazing oversized screen porch overlooks the picturesque & peaceful low maintenance property sure to be enjoyed in every season. Walk to Brett Woods & enjoy over 180 acres of walking trails or hop in the car and get to shopping & dining in minutes. Move in and enjoy as is, or create the stylish home of your dreams. City water and gas in the street- please do your own research for connection possibilities. You can be in your new home for the holidays!

80 Gilbert Hwy, Fairfield

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