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

PICTURES COMING ON MARKET 9/11/2026. Welcome to a rare East Norwalk gem on sought-after Ludlow Manor-a quiet one-way street where homes seldom become available. This spacious three-bedroom, two-full-bath home offers generously sized bedrooms, abundant living space, and a flexible layout with a bedroom and full bathroom on the main level. The location is truly special. Walk to both Calf Pasture Beach and Shady Beach and enjoy the coastal lifestyle right outside your door. Ludlow Park and its tennis courts are directly across the street. Dog owners will love being close to the expansive and popular Taylor Farm Dog Park, featuring separate off-leash areas where dogs have plenty of room to explore and play. The East Norwalk Metro-North station is also within walking distance, offering convenient service to New York City in approximately one hour. Restaurants, cafes, shopping, SoNo, Shorehaven Golf Club, and neighboring Westport are all just minutes away. At home, enjoy a main-level deck, a

Whether you're looking for your first home, a renovation project, or your next investment opportunity, this charming 2-bedroom home is full of potential. Featuring hardwood floors, a cozy fireplace, and a spacious sunroom filled with natural light, the home offers a wonderful foundation to create something truly special. Additional highlights include a full basement, large attic for storage, attached garage, fully paid-for solar panels, and a newer gas boiler for added efficiency and peace of mind. Bring your imagination and transform this home into your dream residence, or take advantage of its excellent investment potential. Ideally located in a walkable neighborhood just steps from Glenbrook's shops, restaurants, and Metro-North train station, with quick access to I-95 (Exit 9), this home combines convenience, character, and opportunity in one desirable package. *HIGHEST AND BEST OFFERS DUE THURSDAY 8/6 AT 5PM

Welcome to this terrific cape style home in a very convenient location! The entry portico leads to the bright living room with hardwood floors and adjacent open concept kitchen. There are French doors from the kitchen out to the back deck, perfect for outdoor dining! There are two bedrooms, each with hardwood floors and a full bathroom on this level as well. Upstairs is a newly carpeted primary bedroom space. The lower level offers a newly carpeted playroom area with wet bar. There is additional storage in the basement boiler room, as well as the washer and dryer. This leads to the under house, 1 car garage. Outside is a terrific level back yard! Interior freshly painted! This is an estate, home to be sold in as-is condition. A great place to make your next home!

Rare Estate Opportunity in the Rowayton Beach Association An exceptional opportunity to build your dream home in one of Rowayton's most sought-after coastal communities. Situated just steps from the water, this property offers direct access to the premier amenities of the Rowayton Beach Association. Enjoy effortless coastal living with private beach access featuring community grills and Adirondack chairs perfectly positioned to capture sweeping views of Long Island Sound. The iconic neighborhood boathouse serves as a vibrant hub for social gatherings, as well as a convenient spot to launch your kayak or paddleboard. Whether you are looking to design a custom seaside retreat or capitalize on a prime location, this estate presents a truly unmatched canvas

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

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

Wonderful large home - great for large/multi-generational family. Ideal Strawberry Hill location convenient to shopping, schools, parks, playgrounds, golf courses, houses of worship, beaches, marinas, train stations, highways and much more! Great space, Room described as office previously used as a nursery/baby room (is adjacent to Primary Bedroom and has 2nd door to hallway), 2 car attached garage, fenced backyard, deck, front patio, central A/C, gas baseboard heating, city water/city sewer. Lower Level room is a possible 5th bedroom or Possible in-law apt (described as Other room in listing). New Central A/C and updated kitchen with new cooking range, sink, dishwasher and new Washer and Dryer. Come see it today!

Timeless craftsmanship meets everyday comfort in this beautifully maintained Colonial, where rich architectural details set it apart. Exquisite millwork, custom paneling, refined wainscoting, and built-ins showcase the quality and character rarely found today. Sun-filled living and dining spaces, anchored by a wood-burning fireplace and gleaming hardwood floors, create a warm and inviting atmosphere. The thoughtfully updated kitchen blends style and function, while the finished lower level offers flexible living space. Outside, a welcoming front porch, white picket fence, and professionally landscaped grounds complete the home's exceptional curb appeal. All just moments from shopping, dining, Metro-North, and downtown Stamford

Whether you're looking for your first home, a renovation project, or your next investment opportunity, this charming 2-bedroom home is full of potential. Featuring hardwood floors, a cozy fireplace, and a spacious sunroom filled with natural light, the home offers a wonderful foundation to create something truly special. Additional highlights include a full basement, large attic for storage, attached garage, fully paid-for solar panels, and a newer gas boiler for added efficiency and peace of mind. Bring your imagination and transform this home into your dream residence, or take advantage of its excellent investment potential. Ideally located in a walkable neighborhood just steps from Glenbrook's shops, restaurants, and Metro-North train station, with quick access to I-95 (Exit 9), this home combines convenience, character, and opportunity in one desirable package. *HIGHEST AND BEST OFFERS DUE THURSDAY 8/6 AT 5PM

Turnkey living in the heart of Darien. Offering over 3,500 square feet of beautifully refreshed living space, this 5-bedroom Colonial combines generous proportions, exceptional outdoor space and one of Darien's most convenient locations, just steps from downtown's newest development and the train. Originally renovated and expanded in 2009 and thoughtfully improved ever since, the home underwent an extensive refresh in 2026 designed for effortless, move-in ready living. The expansive, open floor plan is anchored by an impressive great room and offers wonderful flexibility across four finished levels. Five bedrooms and 3.5 baths are complemented by finished third-floor bonus space and a versatile lower level currently configured as a mudroom, gym, and wine room. Outside is the home's unexpected showstopper. Set on a beautifully landscaped 0.40-acre property, the remarkably spacious and private backyard feels like its own retreat, complete with a stone patio, pool, and six-foot privacy fe

One bedroom condo in highly desirable Winnipauk Village! One of Norwalks best condo complexes with low common charges. Lower level unit opens to a spacious living room, dining area and open kitchen. One full bath with washer/dryer. Large bedroom with sliders to private deck overlooking the pool. Beautiful grounds, 2 pools, kiddie pool, clubhouse, gym and pickleball courts. Pet friendly complex

Rare Estate Opportunity in the Rowayton Beach Association An exceptional opportunity to build your dream home in one of Rowayton's most sought-after coastal communities. Situated just steps from the water, this property offers direct access to the premier amenities of the Rowayton Beach Association. Enjoy effortless coastal living with private beach access featuring community grills and Adirondack chairs perfectly positioned to capture sweeping views of Long Island Sound. The iconic neighborhood boathouse serves as a vibrant hub for social gatherings, as well as a convenient spot to launch your kayak or paddleboard. Whether you are looking to design a custom seaside retreat or capitalize on a prime location, this estate presents a truly unmatched canvas

Exceptional investment opportunity in a highly convenient Stamford location! This unique mixed use property features three residential units plus a commercial space, offering multiple streams of income and outstanding flexibility for investors and owner-occupants alike. The residential units include a spacious 2 bedroom apartment, a 1 bedroom apartment, and a studio, providing strong rental potential and a variety of occupancy options. The commercial space adds additional income producing opportunities, making this an attractive addition to any investment portfolio. Whether you're a seasoned investor looking to maximize cash flow or a buyer seeking to offset your mortgage through rental income, this property presents the perfect house hacking opportunity. Off street parking is available for all units, a valuable amenity for both residential and commercial tenants. Conveniently located near shopping, dining, transportation, and major commuter routes, this versatile property combines loc

Delightful cape style home offering effortless and modern upgrades on a private, fully fenced lot in prime Darien. Highlights include classic hardwood floors, a bright living room, a main-level bedroom, a den/office and two completely renovated full baths-one on each floor. The window lined dining room features a skylight and direct access to the deck which is perfect for entertaining. The second level boasts two flexible bedrooms with built-in storage and the second, completely renovated, full bath. The partially finished lower level offers a finished room which is currently used as a TV room, new washer and dryer, updated mechanicals, tankless hot water system and plenty of room for storage. This home is conveniently located minutes from downtown Darien, schools, restaurants and train stations

Welcome to 36 Dairy Farm Road! A picture perfect 4/5 BR, 2.5 bath colonial, situated on a level.32-acre landscaped lot in a desirable yet conveniently located neighborhood. 2966 SF of inviting, well thought-out living space make this home a perfect blend of charm and function for modern living and effortless entertaining. A commuter's delight,close to train and highways. Walk to schools and just minutes from the lovely beaches of this shoreline CT town. The foyer enters to a warm 1st floor family rm with fireplace.The open,large EIK is uniquely equipped with 2 gas ranges and sinks to handle large holiday gatherings and meal prep with ease. It also offers direct access to the outdoor deck, seamlessly blending indoor and outdoor dining. Host unforgettable gatherings in the large formal dining room, which overlooks a grand, sunken living room. This sophisticated WOW room boasts elegant crown molding and 2nd beautiful marble fireplace that serves as a stunning focal point. Gleaming hardwoo

Fantastic investment or owner-occupy opportunity in heart of Glenbrook. This versatile 2 family offers the ideal setup for buyers looking to offset their mortgage with rental income to expand their portfolio. Unit 1: 3 bed 1.5 bath, unit 2: cozy 1 bed and 1 bath. Both able to generate steady income and renovated 2023. Outdoor space boasts of private backyard grilling, gardening, and relaxing. Commuters dream, close to I-95, merritt 15, train, and minutes from downtown Stamford. Must see!

Introducing 91 Hope - an exclusive boutique collection of 26 residences in the Glenbrook area of Stamford. Designed for modern living, each home features open layouts, high ceilings, and modern finishes. Gourmet kitchens fit with quartz countertops, bespoke cabinetry, premium stainless-steel appliances and large center islands. Spacious bedrooms with ample closet space, designer baths, and private outdoor spaces complete with a two-car garage. Just a short distance from downtown Stamford, Metro-North, and premier dining and shopping, 91 Hope offers an unparalleled blend of elegance, comfort, and convenience. This project is under construction and all showing is through the listing broker with expected completion this fall. Agents and potential buyers are not permitted on the premises unaccompanied without listing agent. Professional photographs of the completed property will be added as construction progresses and the home becomes photo-ready. Images currently shown are architectural r

Situated on a charming cul-de-sac in one of Darien's most desirable coastal neighborhoods, 21 Harbor Road offers approximately 4,400 square feet of beautifully updated living space, with water views from most rooms and within walking distance of Great Island, Pear Tree Point Beach, and Weed Beach. Expertly expanded and renovated, this 5-bedroom, 3.5-bathroom 1960s Cape pairs classic New England character with sophisticated interiors. The newly created primary suite features vaulted ceilings, a luxurious bath, walk-in closet, and adjoining room ideal for an office, exercise studio, or a 5th bedroom. At the heart of the home is a stunning new kitchen with custom cabinetry, French limestone floors, soapstone countertops, and Sub-Zero and Wolf appliances. A custom bar, beverage refrigeration, and pantry add functionality. Classic french doors open to a new bluestone patio with unobstructed water views. Designer fixtures and elevated finishes complement refinished hardwood floors, paint and

Welcome to 47 Second Street, an impeccably maintained two-family Colonial in one of East Norwalk's most desirable coastal neighborhoods. Built in 1890 and situated on an oversized 0.25-acre lot, this charming property offers a fantastic opportunity for both homeowners and investors. Each unit features two spacious bedrooms and one full bathroom, providing comfortable and functional living spaces. Live in one unit while generating rental income from the other, or add this well-maintained property to your investment portfolio. The current tenant is on a month-to-month lease, offering flexibility for the new owner. Conveniently located near beaches, marinas, shopping, dining, parks, and commuter transportation, this versatile two-family home combines historic character with exceptional potential in a sought-after East Norwalk location

Spacious Colonial in the sought-after Hindley Elementary School district! Offering over 2500sf on the main and upper levels, this 5-bedroom, 3 full and 1 half bath home is designed for comfortable everyday living and entertaining. The oversized primary suite is complemented by generous living spaces, while 500sf finished lower level with wet bar provides an ideal recreation room, media room, home gym, or entertaining space. The eat-in kitchen opens to a large deck overlooking a private, fully fenced backyard-perfect for outdoor dining, children, pets, and summer gatherings. Enjoy the convenience of sidewalks leading to Darien's train station, downtown shops, restaurants, parks, beaches, and the Darien YMCA with beach view just across the street, offering competitive swimming and outstanding gymnastic programs, nursery school and activities for all ages. Public transportation is nearby, and quick access to I-95 makes commuting a breeze. Move right in and experience the exceptional conve

Fabulous opportunity along the 5 Mile River! Spacious, 4500+SF Custom Contemporary on the border of Darien and New Canaan. Situated on a highly desirable cul-de-sac, with a pillared drive, on 2+ private acres, overlooking the 5 Mile River. Offering unique architectural details and modern flexibility with over 3100+/- SF of 1st floor living and an additional 1300+/- SF on the 2nd floor. Currently configured as a 3 bdrm, 3 bath home that can easily, transform into a 4/5 bdrm, 5 bath home within the existing footprint. Highlights include: Dramatic Cathedral Ceilings, floor to ceiling field stone fireplaces, large 1st floor primary suite (that can function as private in-law quarters), multi-use loft spaces, walls of glass, abundant water and nature views, 5 fireplaces (4 fieldstone and 1 brick), an attached, oversized 2 car garage with loft and bonus outdoor carport, remarkable privacy and a central location with quick easy access to I-95, Merritt Pkwy and the NYC train. A true hidden gem.

Set on a desirable 1-acre lot in a quiet neighborhood setting on the west side of town, this property offers exceptional potential to renovate, expand or reimagine the existing home to fit your lifestyle. Ideally located with easy access to town, the Merritt Parkway, shopping, dining, and top-rated schools, the property combines convenience, privacy, and enduring neighborhood appeal. A rare opportunity to create your dream home in one of New Canaan's most desirable locations. Please do not walk property without confirmed appointment

BEST AND FINAL OFFERS BY 8/31/26. This One Checks ALL The Boxes! Fabulous location, beautifully renovated spaces, room to entertain inside and out-and a layout that simply works. This 3-bedroom, 2-bath (including one in the primary), Glenbrook home offers 2,254 square feet of bright, inviting living space with hardwood floors and thoughtful updates throughout. The beautifully renovated kitchen is a showstopper with crisp white cabinetry, quartz counters, stainless steel appliances and an island with seating, all open seamlessly to the dining and living areas. The sun-filled living room is anchored by a striking stone fireplace. Renovated baths bring a fresh, sophisticated feel. The lower-level family room with another fireplace is the place to enjoy a good movie. There is even ample space for a great office too. Love to entertain' You are covered inside and out. The walk-out basement adds even more flexible living and entertaining space, while an attached garage adds everyday convenien

Timeless craftsmanship meets everyday comfort in this beautifully maintained Colonial, where rich architectural details set it apart. Exquisite millwork, custom paneling, refined wainscoting, and built-ins showcase the quality and character rarely found today. Sun-filled living and dining spaces, anchored by a wood-burning fireplace and gleaming hardwood floors, create a warm and inviting atmosphere. The thoughtfully updated kitchen blends style and function, while the finished lower level offers flexible living space. Outside, a welcoming front porch, white picket fence, and professionally landscaped grounds complete the home's exceptional curb appeal. All just moments from shopping, dining, Metro-North, and downtown Stamford

Welcome to 57 Rowayton Ave where refined luxury meets effortless coastal living in the heart of Rowayton. Designed by Beinfield Architecture, this exceptional waterfront home offers sophisticated design, timeless craftsmanship, and an unparalleled location on the Five Mile River. Ideally situated beside the town dock and steps from Rowayton Seafood, this 3-bedroom, 5-bath home combines water views, a private 38-foot dock, and the convenience of village living. Inspired by the elegance of a luxury yacht, the home features rich mahogany throughout, from the custom kitchen countertops to the dramatic family room with its soaring arched ceiling. Walls of glass and expansive accordion doors open to a stunning waterfront terrace, creating a seamless connection between indoor and outdoor living. The open-concept floor plan is filled with natural light and designed for everyday living and entertaining. An elevator services every level, while a temperature-controlled wine cellar adds another th

Introducing 91 Hope - an exclusive boutique collection of 26 residences in the Glenbrook area of Stamford. Designed for modern living, each home features open layouts, high ceilings, and modern finishes. Gourmet kitchens fit with quartz countertops, bespoke cabinetry, premium stainless-steel appliances and large center islands. Spacious bedrooms with ample closet space, designer baths, and private outdoor spaces complete with a two-car garage. Just a short distance from downtown Stamford, Metro-North, and premier dining and shopping, 91 Hope offers an unparalleled blend of elegance, comfort, and convenience. This project is under construction and all showing is through the listing broker with expected completion this fall. Agents and potential buyers are not permitted on the premises unaccompanied without listing agent. Professional photographs of the completed property will be added as construction progresses and the home becomes photo-ready. Images currently shown are architectural r

Welcome to Sono Gardens, a gated townhouse-style condominium community in the heart of South Norwalk. This spacious townhouse offers 3 bedrooms and 1 full bath with a bright open-concept layout ideal for today's living. Hardwood floors run throughout, adding warmth and character. Enjoy the convenience of in-unit laundry and a large private basement perfect for storage, home gym, or future expansion. Property is being sold as-is and requires some renovation, presenting a great opportunity to customize and add value. The unit includes one assigned parking space and is located within a secure, well-kept complex. Ideally located minutes from SONO restaurants, shopping, Vets park, Calf Pasture Beach, Metro-North, and major highways-this is low-maintenance living with an unbeatable location. *Income Restrictions, no rentals and no pets

A rare opportunity to live in the exclusive Wilson Point Association, this stately Georgian Colonial is privately sited on 1.4 acres with sweeping views of Long Island Sound. A true secluded oasis, the home features a sophisticated open floor plan, vaulted ceilings, light-filled rooms, and exceptional custom millwork and architectural details throughout. The luxurious primary suite offers a fireplace, spa-like bath, and private terrace overlooking the water. An impressive pool house with a full kitchen extends the home's entertaining and living space, while the expansive flagstone patio, pool, and spa create an exceptional setting for relaxed outdoor living. Residents of Wilson Point enjoy access to a private beach, clubhouse, and tennis court. A truly special year-round retreat, offering privacy, resort-like amenities, and an idyllic waterfront setting-all just an hour from New York City. *$1200 additional annual dues for beach association

Welcome to 47 W Norwalk Road, a newly built 2026 home in desirable West Norwalk, directly on the Darien border-the property behind you is Darien! This 4-bedroom, 3.5-bath home features a finished basement, all-new electrical, plumbing, mechanicals, central air, recessed lighting, and luxury finishes throughout. Wide-plank white oak hardwood floors lead to a show-stopping kitchen with dramatic vaulted ceilings, extensive cabinetry, walk-in pantry, and Taj Mahal quartzite countertops, backsplash, and statement island. The main level is designed for living and entertaining with a dining room, private en-suite bedroom with full bath, dedicated office, and powder room. Upstairs are 3 additional bedrooms, 2 full baths and second-floor laundry. The primary suite features an oversized walk-in closet and spa-like walk-in shower with 3 shower heads. The finished basement provides additional flexible living and entertaining space. A brand-new rear deck overlooks a huge fenced backyard with room f

Welcome to this charming and cozy bungalow nestled in the heart of Norwalk-an ideal alternative to condo living without the fees! This delightful 2-bedroom, 2 full bath home offers the perfect blend of character, comfort, and convenience. Step inside to find beautiful hardwood floors throughout and a warm, inviting layout. A finished and heated loft provides valuable additional space-perfect for storage, a home office, or creative use. The exterior has been meticulously maintained, featuring durable Hardie board siding and a newer asphalt roof for peace of mind. Enjoy your own private backyard oasis, ideal for gardening, entertaining, or simply unwinding. The spacious deck is perfect for summer BBQs or relaxing evenings at home. Located just moments from The SoNo Collection, with easy access to I-95 and Route 7, and only minutes to the train station, restaurants, and vibrant local entertainment-this home truly offers it all. Don't miss this opportunity-schedule your private viewing tod