Portland, CT Homes for Sale with Acreage

/40
$1,099,999
- 4 Beds
- 5 Baths
- 5,572 Sq Ft
279 Middle Haddam Rd, Portland, CT 06480

Set in one of Portland's most picturesque locations with sweeping Connecticut River views, this beautiful expanded Cape Cod tells a story of timeless craftsmanship, thoughtful updates, and distinctive lifestyle amenities. The custom kitchen showcases custom cabinetry with bright quartz countertops and an expansive island designed for gathering and entertaining. Warmth and character carry

Amy Rio

Better Homes and Gardens Real Estate Executive Real Estate

(860) 932-8090

279 Middle Haddam Rd, Portland, CT 06480
Explore Portland
/40
$580,000

Coming Soon
- 4 Beds
- 2.5 Baths
- 2,598 Sq Ft
89 Culver Ln, Portland, CT 06480

Meticulously maintained 4-bedroom, 2.5-bath home set on 1.29 picturesque acres offering the perfect blend of comfort, style, and country living. This inviting open-concept layout features a gorgeous eat-in kitchen with granite countertops and stainless-steel appliances, dining area, and spacious living room highlighted by hardwood floors, vaulted ceiling, and a stunning two-sided fireplace. The

Cheryl Zalewski

eXp Realty

(860) 532-1699

89 Culver Ln, Portland, CT 06480
/2
$759,900

New Construction $30K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,521 Sq Ft
62 Cornwall St, Portland, CT 06480

Come custom build the Home of your dreams. With a wide selection of plans, and possible Options and upgrades, this is something you do not want to wait for!

Amy Rio

Better Homes and Gardens Real Estate Executive Real Estate

(860) 943-4408

62 Cornwall St, Portland, CT 06480
/40
$699,000
- 3 Beds
- 4 Baths
- 2,859 Sq Ft
235 Middle Haddam Rd, Portland, CT 06480

Set on a scenic rise known as "Taylor Hill," this architect-designed home offers a rare blend of history, privacy, and natural beauty. Originally built in 1979 and expanded over time, the residence incorporates a distinctive early 20th-century guesthouse and thoughtful modern additions, creating a unique and flexible layout. Surrounded on three sides by permanently protected conservation land

Carl Guild Carl Guild & Associates

235 Middle Haddam Rd, Portland, CT 06480
/12
$124,900
- Land
- 4.15 Acres
- $30,096 per Acre
426 Cox Rd Unit 4, Portland, CT 06480

NEW PORTLAND SUBDIVISION - KELSEYS POND ESTATES. Custom Homes by Lepore and Sons LLC. New land lots with views of Kelseys Pond across the road! Short distance to Meshomasic State Forest and the walking trails. Quarry Ridge Golf Course nearby. Minutes to all the amenities in Portland, Middletown and Glastonbury. Perfectly situated near Routes 2 & 9. Other lots available. One or more of this

Steven Lepore West Wind Realty, LLC

426 Cox Rd Unit 4, Portland, CT 06480
/7
$199,900
- Land
- 12.27 Acres
- $16,292 per Acre
184 Cox Rd, Portland, CT 06480

Absolutely top-tier parcel of Land offering over 12 acres of exceptional privacy, natural beauty, and serene surroundings. Accessed at the top of your very own private road (Molly Lane), this remarkable lot sits high with lots of potential with many level areas to build- ideal for creating a truly special custom estate. This is not an ordinary piece of land; it represents a rare opportunity to

Anna Zastem Macchio William Raveis Real Estate

184 Cox Rd, Portland, CT 06480
/12
$99,900
- Land
- 1.23 Acres
- $81,220 per Acre
402 Cox Rd Unit 8, Portland, CT 06480

NEW PORTLAND SUBDIVISION - KELSEYS POND ESTATES. Custom Homes by Lepore and Sons LLC. New land lots with views of Kelseys Pond across the road! Short distance to Meshomasic State Forest and the walking trails. Quarry Ridge Golf Course nearby. Minutes to all the amenities in Portland, Middletown and Glastonbury. Perfectly situated near Routes 2 & 9. Other lots available. One or more of this

Steven Lepore West Wind Realty, LLC

402 Cox Rd Unit 8, Portland, CT 06480
/35
$499,000

$76K PRICE DROP
- 2 Beds
- 2.5 Baths
- 4,205 Sq Ft
286 Marlborough St, Portland, CT 06480

This unique property presents an exceptional opportunity for both investors and owner-occupants seeking flexibility and income potential. The upper level offers a well-appointed two-bedroom, one-bath apartment filled with natural light-perfect for immediate occupancy or reliable rental income. On the first floor, a spacious layout that previously operated as a salon provides a blank canvas for

Kris Robinson Eagle Eye Realty PLLC

286 Marlborough St, Portland, CT 06480
/12
$124,900
- Land
- 2.8 Acres
- $44,607 per Acre
432 Cox Rd Unit 3, Portland, CT 06480

NEW PORTLAND SUBDIVISION - KELSEYS POND ESTATES. Custom Homes by Lepore and Sons LLC. New land lots with views of Kelseys Pond across the road! Short distance to Meshomasic State Forest and the walking trails. Quarry Ridge Golf Course nearby. Minutes to all the amenities in Portland, Middletown and Glastonbury. Perfectly situated near Routes 2 & 9. Other lots available. One or more of this

Steven Lepore West Wind Realty, LLC

432 Cox Rd Unit 3, Portland, CT 06480
/19
$539,900
- 4 Beds
- 3.5 Baths
- 4,390 Sq Ft
57 Summer St, Portland, CT 06480

Set on a generous 1.2-acre lot in Portland, this expansive ranch offers an incredible amount of space and potential for someone ready to bring their vision to life. With over 4,300 square feet of living space, the home features 10 rooms including 4 bedrooms and 3 full baths plus a half bath, providing plenty of room for extended living, hobbies, or multi-generational needs. The layout offers the

Carl Guild Carl Guild & Associates

57 Summer St, Portland, CT 06480
/37
$585,000
- 3 Beds
- 3.5 Baths
- 2,587 Sq Ft
331 Middle Haddam Rd, Portland, CT 06480

Tucked away on 3.62 private acres and surrounded by the charm of Portland's historic district, this stunning reproduction Colonial built in 2004 offers the character of a historic New England home with the comfort and convenience of modern living. Set behind a fully fenced yard with apple, pear, cherry, and peach trees, the property backs directly to over 40 acres of protected Middlesex Land

Alan Spotlow William Raveis Real Estate

331 Middle Haddam Rd, Portland, CT 06480
/8
$125,000
- Land
- 2.82 Acres
- $44,326 per Acre
182 Cox Rd, Portland, CT 06480

Approved 2.82-acre residential building lot in Portland, zoned R-25 and ready for your build. The lot sits off Cox Road with solid frontage and a gradual rise from the street, giving the site natural elevation and privacy without fighting the topography. Established tree cover provides natural screening on the upper portions of the lot, and surrounding parcels carry single-family homes, setting

Carl Guild Carl Guild & Associates

182 Cox Rd, Portland, CT 06480
/12
$99,900
- Land
- 1.04 Acres
- $96,058 per Acre
438 Cox Rd Unit 2, Portland, CT 06480

NEW PORTLAND SUBDIVISION - KELSEYS POND ESTATES. Custom Homes by Lepore and Sons LLC. New land lots with views of Kelseys Pond across the road! Short distance to Meshomasic State Forest and the walking trails. Quarry Ridge Golf Course nearby. Minutes to all the amenities in Portland, Middletown and Glastonbury. Perfectly situated near Routes 2 & 9. Other lots available. One or more of this

Steven Lepore West Wind Realty, LLC

438 Cox Rd Unit 2, Portland, CT 06480
/12
$99,900
- Land
- 1.34 Acres
- $74,552 per Acre
444 Cox Rd Unit 1, Portland, CT 06480

NEW PORTLAND SUBDIVISION - KELSEYS POND ESTATES. Custom Homes by Lepore and Sons LLC. New land lots with views of Kelseys Pond across the road! Short distance to Meshomasic State Forest and the walking trails. Quarry Ridge Golf Course nearby. Minutes to all the amenities in Portland, Middletown and Glastonbury. Perfectly situated near Routes 2 & 9. Other lots available. One or more of this

Steven Lepore West Wind Realty, LLC

444 Cox Rd Unit 1, Portland, CT 06480
/34
$638,000
- 4 Beds
- 2.5 Baths
- 2,260 Sq Ft
31 Fox Run Rd, Portland, CT 06480

Tucked at the end of a quiet cul-de-sac on nearly 3 private acres, this meticulously maintained home is truly turn-key, and it shows in every detail. A brand new roof and brand new hardwood floors throughout the entire home completed in spring of 2026 give the home a pristine, like-new feel. The main level flows beautifully from a sun-filled kitchen with stainless steel appliances, granite

Corey Briggs William Raveis Real Estate

31 Fox Run Rd, Portland, CT 06480

Connecticut Middlesex County Portland

Home Trends in Portland, CT

On average, homes in Portland, CT sell after 36 days on the market compared to the national average of 58 days. The median sale price for homes in Portland, CT over the last 12 months is $390,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$390,000

Median Single Family Sale Price

$410,000

Median Townhouse Sale Price

$335,000

Median 2 Bedroom Sale Price

$325,000

Median 1 Bedroom Sale Price

$169,750

Average Price Per Sq Ft

$241

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

2.00

Median List Price

$384,900

Median Change From 1st List Price

-2%

Median Home Sale Price YoY Change

How to Buy a Home How to Finance a Home How to Sell a Home

In Portland, there are currently 15 homes for sale with acreage, providing ample space for homeowners to customize their living environment, whether for expansive gardens, outdoor entertaining, or enhanced privacy. Whether you're in search of a spacious family home with plenty of room to roam, a property ripe for development, or simply seeking space and tranquility, homes for sale with acreage in Portland, CT offer the flexibility to tailor your living experience to your preferences. Browse the selection of homes for sale with land in Portland and discover the potential and freedom that comes with owning your own piece of property.

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