1,056 houses for sale in Boston Post Road Historic District

A truly exceptional private estate, this country compound set on more than three private acres, blends timeless character, refined design, and modern luxury. Anchored by a beautifully preserved 1932 main residence and an extraordinary 2,300-square-foot poolside entertainment barn, the property is designed for both everyday living and effortless entertaining. The main residence offers five bedrooms and three full baths, including a luxurious primary suite with spa-like bath, expansive walk-in closet, and private deck overlooking the grounds. Gracious formal living and dining rooms complement a chef's kitchen opening to the family room and breakfast area. A finished lower level provides additional living and entertaining space. The poolside barn is a destination unto itself, with a dramatic Great room, wet bar and kitchenette, private gym, home office, full bath, and outdoor shower. Expansive lawns, perennial gardens, multiple outdoor fireplaces, a spectacular swimming pool, and gracious

A truly exceptional private estate, this country compound set on more than three private acres, blends timeless character, refined design, and modern luxury. Anchored by a beautifully preserved 1932 main residence and an extraordinary 2,300-square-foot poolside entertainment barn, the property is designed for both everyday living and effortless entertaining. The main residence offers five bedrooms and three full baths, including a luxurious primary suite with spa-like bath, expansive walk-in closet, and private deck overlooking the grounds. Gracious formal living and dining rooms complement a chef's kitchen opening to the family room and breakfast area. A finished lower level provides additional living and entertaining space. The poolside barn is a destination unto itself, with a dramatic Great room, wet bar and kitchenette, private gym, home office, full bath, and outdoor shower. Expansive lawns, perennial gardens, multiple outdoor fireplaces, a spectacular swimming pool, and gracious

Welcome to this beautifully renovated two-bedroom condo in one of Darien's most convenient locations. Just steps from Goodwives shopping center, the Metro-North train station, and the vibrant energy of downtown Darien, this home offers the perfect blend of modern comfort and walkable lifestyle. Pass through the private gate and be greeted by a serene personal courtyard and garden. A sliding glass door from the living area provides seamless access to this peaceful outdoor retreat-ideal for morning coffee, evening relaxation, or entertaining. The open-concept main level features a bright, updated kitchen that flows effortlessly into the dining and living areas. A cozy fireplace anchors the living room, creating a warm and inviting space for gatherings or quiet nights in. Upstairs, the primary suite impresses with dramatic vaulted ceilings and an enviable en-suite bathroom. Soak in the large soaking tub or enjoy the separate shower after a long day. A second en-suite bedroom and laundry i

Welcome to this beautifully renovated two-bedroom condo in one of Darien's most convenient locations. Just steps from Goodwives shopping center, the Metro-North train station, and the vibrant energy of downtown Darien, this home offers the perfect blend of modern comfort and walkable lifestyle. Pass through the private gate and be greeted by a serene personal courtyard and garden. A sliding glass door from the living area provides seamless access to this peaceful outdoor retreat-ideal for morning coffee, evening relaxation, or entertaining. The open-concept main level features a bright, updated kitchen that flows effortlessly into the dining and living areas. A cozy fireplace anchors the living room, creating a warm and inviting space for gatherings or quiet nights in. Upstairs, the primary suite impresses with dramatic vaulted ceilings and an enviable en-suite bathroom. Soak in the large soaking tub or enjoy the separate shower after a long day. A second en-suite bedroom and laundry i

Welcome to this beautifully renovated two-bedroom condo in one of Darien's most convenient locations. Just steps from Goodwives shopping center, the Metro-North train station, and the vibrant energy of downtown Darien, this home offers the perfect blend of modern comfort and walkable lifestyle. Pass through the private gate and be greeted by a serene personal courtyard and garden. A sliding glass door from the living area provides seamless access to this peaceful outdoor retreat-ideal for morning coffee, evening relaxation, or entertaining. The open-concept main level features a bright, updated kitchen that flows effortlessly into the dining and living areas. A cozy fireplace anchors the living room, creating a warm and inviting space for gatherings or quiet nights in. Upstairs, the primary suite impresses with dramatic vaulted ceilings and an enviable en-suite bathroom. Soak in the large soaking tub or enjoy the separate shower after a long day. A second en-suite bedroom and laundry i

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

Exceptional Four-Unit Investment Opportunity in the Heart of Norwalk! Rarely does a property like this become available. Situated on one parcel with two separate buildings. 32 Catherine Street offers an outstanding opportunity for investors, owner-occupants, or those seeking a multigenerational living arrangement with significant rental income. The front building is a spacious two-family home featuring two oversized 3-bedroom, 1-bath apartments, each offering generous living space and strong rental appeal. Tucked behind the main residence is a separate ranch-style building with two additional units, including a 1-bedroom, 1-bath apartment and a 3-bedroom, 2-bath apartment, creating an ideal mix of unit sizes to maximize occupancy and income potential. With almost 4,000 square feet of living space (buyer to verify), this unique four-unit property provides four separate income streams and the flexibility today's buyers are looking for. Whether you're expanding your real estate portfolio,

Charming bungalow-style home offering easy one-floor living, abundant natural light, high ceilings and character throughout. A welcoming front porch sets the tone, while freshly painted interiors provide a bright, fresh backdrop. The spacious great room features a striking stone fireplace, built-in bookcases and generous proportions for everyday living and entertaining. The kitchen enjoys views across the expansive, level backyard, and three bedrooms and two full baths complete the main level. The walk-out lower level adds exceptional flexibility with a family room featuring French doors opening directly to the patio, plus an additional bedroom and full bath. Turn-key and ready to enjoy today, the home also offers exciting expansion potential and flexibility to grow over time. A standout feature is the convenient location-just a short walk to Noroton Heights shopping, restaurants, amenities and train station, as well as Middlesex Middle School and Darien High School. An extensive netwo

Hidden behind Shorehaven Country Club in a gated waterfront enclave, 3 Canfield Crossing offers the rare opportunity to enjoy WATERFRONT LIVING in a NATURALLY PROTECTED WATERFRONT SETTING. Thoughtfully reimagined and extensively updated, the property combines timeless coastal design with the peace of mind of significant recent improvements, including a BRAND NEW CEDAR ROOF, new windows, several new mechanical systems, a new pool heater, and an entirely new chef's kitchen with custom cabinetry and premium appliances. Designed to embrace its waterfront setting, nearly every room captures views of the ever-changing tides. A NanaWall opens the newly renovated kitchen and living areas directly to the expansive waterfront terrace and infinity-edge pool, creating an effortless connection between indoors and out. With four finished levels connected by elevator, six ensuite bedrooms, including two separate guest or au pair opportunities, the home offers exceptional flexibility for everyday livi

Discover your own slice of heaven in this charming 3 bedroom, 2 bath Colonial, ideally situated on a beautifully landscaped 0.37 acre lot on a private cul-de-sac. Offering the perfect blend of privacy and convenience, this home has been cherished as a second residence by the same owner for more than 25 years. The main level features a spacious living room, formal dining room, and an eat-in kitchen with access to a wraparound deck. A first-floor bedroom and a full bath add convenience and versatility. Upstairs, you'll find two generously sized bedrooms and a second full bath. The walkout lower level includes a family room with a fireplace, utility room, and an attached one-car garage. Surrounded by mature perennial gardens, ornamental trees, and a tranquil koi pond, the property provides a serene setting for everyday living. Recent updates include central air conditioning and replacement windows. Cosmetic updating will make this home a real showpiece. The finished lower level family roo

Built in 2023 by noted developer Ritzzo Development and thoughtfully refreshed in 2026, this striking Contemporary Colonial offers 10,000+ square feet of elevated living on two manicured acres with a heated saltwater pool and built-in BBQ. Extensive 2026 improvements - including new paint, refinished wide-plank white oak floors, new trim, updated AV, a whole-house generator, and a fully reimagined lower level - make this feel like a brand new home in every sense. Inside, soaring ceilings, custom millwork, and luxurious finishes define every room. The open-plan chef's kitchen features a marble waterfall island and flows into a sun-filled breakfast room and dramatic great room with vaulted beamed ceiling and double-height fireplace. Stylish formal rooms, a butler's pantry, and a private office complete the main level. The primary suite is a true retreat - featuring a fireplace, private deck, and lavish bath. The reimagined lower level offers a media room, gym, sauna, and steam room. A ra

Ideally located on a private lot in close proximity to public and private schools, 25 Hillcrest Rd. is located on a low traffic street on New Canaan's lower west side within minutes of the Merritt Parkway, Talmadge Hill train station and down town New Canaan. Spanning close to 8,000 sq ft, the transitional floor plan masterfully blends open concept spaces with more intimate, private spaces. Featuring 9' ceilings throughout and a clean, contemporary design aesthetic, the gracious home is perfect for entertaining large crowds while at the same time comfortable for everyday living. Entering through the custom designed front door, you are welcomed by a grand foyer with unobstructed views through the living room to the private backyard. As you move through the home, the centrally located family room is connected to both the large formal dining room and the gourmet kitchen which is flooded with natural light through six over sized windows. Featuring a clean, white design aesthetic the kitche

Welcome to 18 Buttonball Trail. Space, comfort and a backyard made for entertaining. This home features 4 Bedrooms, 3 baths, newly refinished hardwood floors, spacious great room w/custom build-in shelving adding character, functionality with extra storage. The well-appointed galley kitchen features rich wood cabinetry, ample counter space, tiled flooring and double oven. Kitchen is open to dining room and great room that walk out to a huge deck, perfect for entertaining summer cookouts! Beyond the deck is a large, level backyard offering privacy and plenty of room for gardening and outdoor activities. A detached garage, private driveway, attractive landscaping and welcoming paver walkway complete the property. Fully finished basement provides valuable bonus space that can serve as a recreation room, studio, gym, workshop, etc. Basement also has full bathroom. This home truly has it all! Tucked away in a peaceful, private setting while still conveniently located near shops, restaurants

Welcome to 34 Nearwater Road, an exquisite home in the coveted Pine Point Assoc just steps from Crescent Beach. This turnkey gem offers year-round water views and a seamless blend of luxury and comfort. The light-filled interior boasts soaring ceilings and an open floor plan that feels both elegant and inviting. The living room, anchored by a wood-burning fireplace, exudes charm, while the formal dining room shines w/ sophisticated coffered ceilings. At the heart of the home is a chef's kitchen featuring state-of-the-art appliances - including 2 refrigerators and dishwashers, perfect for culinary adventures. Adjacent spaces include a bright office and a chic bar area, making entertaining effortless. A refined powder room completes the main level. Upstairs, the primary suite is a true retreat with a cozy gas fireplace, 2 walk-in closets, and a spa-like bath with a tub. Three additional ensuite bedrooms ensure privacy for family and guests, while the laundry room adds convenience. The 3r

This dramatic property offers 200 feet of waterfront frontage with your own private beach in the premier Long Neck Point area of Darien. Offering two separately deeded parcels ( that create this magical estate to ensure the peace and tranquility of your own private oasis. East facing views are enjoyed from most rooms in this spectacular home offering natural light throughout the day. Once owned by Christopher Plummer of The Sound of Music, the current owners have meticulously renovated and restored this cherished home with the renowned builders, Significant Homes and interior designer, Cindy Rinfret, Rinfret LLC. The architectural integrity has been preserved with comfort and quality for today's lifestyle. A world-class property. Parcel IDs 61 10 (207) and 61 10-2 (209)

FrogPond Estate is New Canaan's most striking modern Scandinavian offering-an architectural achievement set on 2.25 private acres just moments from town and train. With 11,836+ sq. ft. of sunfilled, designdriven living space, this 7 bed, 9.5bath custom residence delivers soaring 12ft ceilings, bespoke millwork, designer lighting, and walls of glass that erase the line between indoors and out. A showstopping doubleisland gourmet kitchen anchors the open main level, perfect for quiet daily living or largescale entertaining. The estate's fully independent 1,190 sq. ft. Cottage-with separate address and utilities-adds a private bedroom, office, full bath, island kitchen, laundry, and a flexible loft ideal for guests, extended family, staff, or professional use. Thoughtfully scaled yet beautifully finished, it elevates FrogPond into a true multidwelling compound. Pool is open. Landscaping complete. Showready today. A rare modern sanctuary-private, polished, and unlike anything else in the m

Turn-key, move in ready modern townhouse located in the heart of downtown New Canaan, this home offers three floors of elegant living with the feel of a single-family residence and the convenience of low-maintenance living. The renovated open floor plan features a state of the art newer chef's kitchen, a breakfast nook, island, and a light-filled living room/dining room with a fireplace. The main floor offers a study or additional bedroom with its own fireplace and large windows. On the second floor, you will find the owner suite featuring- a renovated luxury bathroom with soaking tub, shower, 2 vanities, two walk-in fitted closets-along with two additional bedrooms, a full bath, and a laundry area. The lower level provides nearly 1,000 square feet of additional walk out living space with fireplace large recreation room and a patio. Outside, the walk-out lower level leads to a private patio and yard, offering a quiet oasis which backs up to a Bristow Park Bird Sanctuary and Mead Park.

Move-in ready 3-bedroom, 2-bathroom split-level on a quiet cul-de-sac in the Cranbury neighborhood of Norwalk, Connecticut. This well-maintained home features hardwood floors, central air conditioning, sprinklers, and a layout designed for flexible living with separate living room, dining room, and family room. The updated kitchen includes granite countertops and stainless steel appliances. Three bedrooms and two full baths provide comfortable space across the split-level floor plan. There is tons of room for storage in the expansive, clean basement, as well as the pull down attic. The private backyard is fenced with mature flowering landscaping, an above-ground pool, and a deck for outdoor dining and entertaining - a ready-made retreat without leaving home. Located on a cul-de-sac in Cranbury, Norwalk, CT, with convenient access to the Merritt Parkway, I-95, and Norwalk shopping and dining. 9 Junebar, Norwalk, CT 06851

Opportunities like 37 Allview Avenue don't come around often. Whether you're a first-time buyer looking to have your mortgage supplemented by rental income or a seasoned investor searching for a high-demand property, this Norwalk multifamily home delivers on every front.The layout is designed for versatility and ease, offering bright, sun-drenched living spaces that feel both fresh and functional. Each unit provides a comfortable flow, with kitchens that serve as the heart of the home and generous living spaces that offer a quiet place to unwind. It's the kind of setup that attracts quality tenants or provides a perfect and comfortable scenario for an owner-occupant. Situated on a great neighborhood street, the property offers a sense of community while keeping you incredibly close to everything that makes Norwalk thrive. You are just minutes away from the retail hub of Connecticut Avenue and have seamless access to I-95, making daily errands and commuting a total breeze. From the invi

Welcome to Sunrise Hill! This well-loved and beautifully maintained 2-bedroom, 1.5-bath townhouse has been cared for by the same owner for 34 years. One of the first things you'll appreciate is the easy access, with just a few steps to the front door-something that sets this unit apart from many others in the complex. Inside, the main level offers a comfortable, inviting layout with plenty of natural light and a nice flow for everyday living. Upstairs are two generously sized bedrooms with ample closet space and a full hall bath. The finished lower level adds great flexibility, with two additional rooms that could work as a home office, den, exercise space or guest area, along with a half bath and laundry. Sliding doors lead directly to the private, fenced-in backyard-a wonderful extension of the living space for relaxing, gardening or entertaining. Sunrise Hill offers a pool, tennis and pickleball courts and two playgrounds, all in a convenient, commuter-friendly location close to sho